WO2002014459A2 - Products comprising corn oil and corn meal obtained from high oil corn - Google Patents
Products comprising corn oil and corn meal obtained from high oil corn Download PDFInfo
- Publication number
- WO2002014459A2 WO2002014459A2 PCT/US2001/025055 US0125055W WO0214459A2 WO 2002014459 A2 WO2002014459 A2 WO 2002014459A2 US 0125055 W US0125055 W US 0125055W WO 0214459 A2 WO0214459 A2 WO 0214459A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- corn
- oil
- meal
- com
- extraction
- Prior art date
Links
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/25—Shaping or working-up of animal feeding-stuffs by extrusion
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
- A23K20/147—Polymeric derivatives, e.g. peptides or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/20—Shaping or working-up of animal feeding-stuffs by moulding, e.g. making cakes or briquettes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
- Y02A40/81—Aquaculture, e.g. of fish
- Y02A40/818—Alternative feeds for fish, e.g. in aquacultures
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/80—Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
- Y02P60/87—Re-use of by-products of food processing for fodder production
Definitions
- the present invention relates to products that are derived from oil and meal extracted from corn having an oil content of about 6 wt.% or more.
- Corn Zea mays L., is grown for many reasons including its use in food and industrial applications. Corn oil and corn meal are two of many useful products derived from corn.
- a corn-based feed product known as hominy feed is obtained from the dry milling process and is a mixture of corn bran, corn germ, and endosperm, and has a minimum of about 4 wt.% oil.
- steps including cracking, grinding, sieving, and blending are required to manufacture hominy feed and the resulting particle size of hominy feed is small relative to meal made by the extraction method described herein.
- Finished products containing corn oil and/or corn meal obtained from conventional corn include, for example, cooking oil, animal feed, paper and paper products, numerous food products such as salad dressings, extruded and/or puffed snack foods, products containing corn sweeteners, cereals, chips, puddings, candies, and breads.
- One aspect of the invention provides a nutritious animal feed comprising the corn meal remaining after extraction of oil from high oil corn having an oil content of about 6 wt.% or greater.
- the animal feed can comprise other nutritious products such as vitamins, minerals, high oil seed-derived meal, meat and bone meal, salt, amino acids, feather meal, and many others used in the art of feed supplementation.
- the animal feed composition can be tailored for particular uses such as for poultry feed, swine feed, cattle feed, equine feed, aquaculture feed, pet food and can be tailored to animal growth phases.
- Particular embodiments of the animal feed include growing broiler feed, swine finishing feed, and poultry layer finishing feed. Feed products can be made with the extracted corn meal that will have a higher relative percentage of protein and lower relative percentage of oil than similar products made with conventional corn.
- Some embodiments of the invention include those wherein: 1) the corn meal has a fiber content of about 3%, a starch content of about 65%, and a protein content of about 12%, at a moisture content of about 10%; 2) the high oil corn grain has a total oil content of at least about 6 wt.%, at least about 7 wt.%, at least about 8 wt.%; at least about 10 wt.%), at least about 12 wt.%, at least about 14 wt.%, or from about 7 wt.% to about 30 wt.%; 3) the corn grain being flaked is whole corn grain or cracked corn grain; 4) the corn grain has been subjected to an oil extraction process such as solvent extraction, hydraulic pressing, or expeller pressing, aqueous and enzyme extraction; 5) the high oil corn grain has a total protein content of at least about 7 wt.%, at least about 9 wt.%, at least about 11 wt.%, or from about 7 wt.%
- a preferred embodiment provides a method of obtaining corn oil and solvent extracted corn meal (SEC) from high oil corn.
- the method provides steps of: 1) tempering the corn; 2) cracking the tempered corn; 3) conditioning the cracked corn; 4) flaking the conditioned corn; 5) extracting the flaked corn; and 6) removing the solvent from both the corn oil and solvent extracted corn meal.
- the method provides a greater overall content of corn oil and concentrates the proteins in the meal.
- solvent extractable pigments can be removed from the SEC.
- Another aspect of the invention provides a corn oil-based product comprising corn oil obtained by extraction of at least the endosperm and germ of high oil corn.
- the corn oil-based product can comprise other components such as vinegar, spices, vitamins, salt, hydrogen (for forming hydrogenated products), and water.
- the corn oil used in the products of the invention will generally contain a higher proportion of ⁇ -carotene, xanthophylls or tocotrienol than similar products made with corn oil extracted from conventional corn employing conventional methods.
- the corn oil, used in the products of the invention is generally produced by exposing the entire corn grain, the cracked corn grain or the flaked corn grain to extraction without separation of the germ from the endosperm.
- the solvent-extractable nutrients present in the endosperm are extracted into the corn oil that has been extracted from the germ and endosperm.
- Products that can be made with the oil prepared as described herein include, but are not limited to, salad dressings, cooking oils, margarines, spray-coated food or feed products, breads, crackers, snack foods, lubricants, and fuels.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A solvent-based extraction process
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an exemplary embodiment of the invention.
- FIG. 1 A block diagram illustrating an
- a third aspect of the invention provides a method of using extracted corn meal in an animal feed ration comprising the step of: 1) providing an extracted corn meal prepared by at least flaking high oil corn to form flaked corn and extracting the flaked corn to remove a portion of the corn oil therefrom; and 2) including the extracted corn meal in an animal feed ration.
- a fourth aspect of the invention provides a method of using an extracted corn oil in a food product comprising the steps of: 1) providing an extracted corn oil obtained by at least flaking high oil corn to form flaked corn and extracting the flaked corn to remove a portion of the corn oil therefrom and form the extracted corn oil; and 2) including the extracted corn oil in a food product.
- a fifth aspect of the invention provides a method of using extracted corn oil as a feedstock in an oil refining process.
- the method comprises the steps of: 1) providing an extracted crude corn oil obtained by at least flaking high oil corn to form flaked corn and extracting the flaked corn to remove a portion of the corn oil therefrom and form the extracted crude corn oil; and 2) including the extracted crude corn oil in a raw material stream of an oil refining process.
- a sixth aspect of the invention provides various methods of forming extracted blended meals.
- a first embodiment of this aspect of the invention provides a method of forming an extracted blended meal comprising an extracted meal obtained from high oil corn and one or more other oilseed meals, the method comprising the step of: 1) combining high oil corn grain and one or more other oilseed grains to form a grain mixture; and 2) subjecting the grain mixture to flaking and an extraction process to remove oil therefrom and form the extracted blended meal.
- a second embodiment provides a method comprising the steps of: 1) combining a cracked and conditioned high oil com with another cracked and conditioned oilseed to form a conditioned mixture; 2) flaking the conditioned mixture to form a flaked mixture; and 3) subjecting the flaked mixture to an extraction process to remove oil therefrom and form the extracted blended meal.
- a third embodiment provides a method comprising the steps of: 1) combining a cracked, conditioned and flaked high oil corn with a cracked, conditioned and flaked other oilseed to form a flaked mixture; and 2) subjecting the flaked mixture to an extraction process to remove oil therefrom and form the extracted blended meal.
- a fourth embodiment provides a method comprising the step of combining an extracted corn meal with one or more extracted other oilseed meals to form a blended meal, wherein the extracted corn meal has been obtained by at least flaking and extracting high oil com to form the extracted com meal.
- a fifth embodiment provides a blended extracted meal product prepared according to any one of the above-described methods.
- a seventh aspect of the invention provides a method of using extracted corn oil as an ingredient in cosmetic applications.
- the method comprises the steps of: 1) providing an extracted cmde corn oil obtained by at least flaking high oil corn to form flaked corn and extracting the flaked corn to remove a portion of the corn oil therefrom and form the extracted crude com oil; and 2) including the extracted cmde corn oil in a cosmetic product.
- types of cosmetics include but are not limited to lipstick and eye liner.
- Another aspect of the invention provides the use of a com meal in an animal feed or human food, wherein the com meal is obtained after extraction of corn oil from whole kernels of high oil corn.
- Yet another aspect of the invention provides the use of a corn oil in an animal feed or human food, wherein the corn oil is obtained by extraction from whole kernels of high oil corn.
- Other aspects of the invention provide com oil-containing and/or corn meal- containing products made by the processes described herein.
- Figure 1 illustrates the total amount of ethanol produced and dextrose consumed by yeast grown on yellow dent corn (YD), yellow dent meal (YDM), high oil corn (HOC), and high oil com meal (HOCM).
- Figure 2 illustrates the pH values of yeast cultures containing yellow dent corn (YD), yellow dent meal (YDM), high oil corn (HOC), and high oil corn meal (HOCM).
- YD yellow dent corn
- YDM yellow dent meal
- HOC high oil corn
- HOCM high oil corn meal
- corn oil can be rapidly and efficiently extracted on a commercial-scale from corn grain having increased oil content by optionally cracking and then conditioning, and flaking the corn grain and extracting a corn oil.
- Useful com grain for the novel flaking oil processing method has a total oil content greater than about 6 wt.%. Increases in the oil content of com grain may increase flaking efficiency during processing.
- Suitable flaking equipment and methods include conventional flaking equipment and methods used for flaking soybean and other similar oilseed types.
- Suitable extracting equipment and methods may include conventional methods used for extracting oil from soybean flakes and other similar oilseed types.
- High oil corn seed or "grain" harvested from any of several different types of corn plants is useful in the invention.
- corn plants are, for example, hybrids, inbreds, transgenic plants, genetically modified plants or a specific population of plants.
- Enhanced extracted meals can be made by subjecting enhanced high oil corn to the extraction process described herein.
- Useful corn grain types include, for example, flint com, popcorn, flour corn, dent corn, white corn, and sweet corn.
- the high oil com grain can be in any form including whole com, cracked corn, or other processed com or parts thereof that are amenable to flaking but different from the standard methods of germ separation employed in dry and wet milling for subsequent recovery of oil from the germ.
- the terms "whole kernel” or “whole corn” mean a kernel that has not been separated into its constituent parts, e.g. the hull, endosperm, tipcap, pericarp, and germ have not been purposefully separated from each other.
- the whole com may or may not have been ground, crushed, cracked, flaked, or abraded.
- Purposeful separation of one corn constituent from another does not include random separation that may occur during storage, handling, transport, crushing, flaking, cracking, grinding or abrading.
- a purposeful separation of the constituent part is one wherein at least 50% of one constituent, e.g., germ, has been separated from the remaining constituents.
- high oil corn refers to com grain comprising at least about 6 wt.% or greater, preferably at least about 7 wt.% or greater, and preferably at least about 8 wt.% or greater oil.
- a high oil com has an elevated level of oil as compared to conventional yellow dent corn, which has an oil content of about 3 wt.% to about 5 wt.%.
- the total oil content of com grain suitable for the invention can be, for example, grain having an oil content at least about 9 wt.%, at least about 11 wt.%, at least about 12 wt.%, at least about 15 wt.%, at least about 18 wt.%, at least about 20 wt.%, from about 8 wt.% to about 20 wt.% oil, from about 10 wt.% to about 30 wt.%) oil, or from about 14 wt.% to about 30 wt.%, and values within those ranges.
- the oil content can be determined at any moisture content, it is acceptable to normalize the oil content to a moisture content of about 15.5%.
- High oil com useful in making the oil and meal described herein are available from Cargill, Incorporated (Minneapolis, MN) or Pfister Hybrid Corn Co. (El Paso, IL).
- Other suitable high oil corn includes the com populations known as Illinois High Oil (IHO) and Alexander High Oil (Alexo), samples ofwhich are available from the University of Illinois Maize Genetics Cooperative - Stock Center (Urbana, IL).
- Corn grain having an elevated total oil content is identified by any of a number of methods known to those of ordinary skill in the art.
- the oil content of grain including the fat content of a meal extracted from the grain, can be determined using American Oil and Chemical Society Official Method, 5 th edition, March 1998, ("AOCS method Ba 3-38").
- AOCS method Ba 3-38 quantifies substances that are extracted by petroleum ether under conditions of the test.
- the oil content or concentration is the weight percentage of the oil with respect to the total weight of the seed sample. Oil content may be normalized and reported at any desired moisture basis.
- corn ears are selected using a near infrared (NIR) oil detector to select corn ears having com kernels with elevated oil levels.
- NIR near infrared
- an NIR detector can also be used to select individual com kernels having elevated levels of corn oil.
- selecting individual ears and/or kernels having elevated oil content may not be cost effective in identifying high oil kernels suitable for processing using methods described herein.
- corn seed producing corn plants that yield grain having elevated total oil concentrations is planted and harvested using known farming methods.
- One of the suitable high oil corns used as a raw material for preparing the com oil and com meal used in the invention has a nutrient profile as shown in Table 1. Amounts are expressed on an "as is" or "as fed” moisture level. Protein, oil, and starch levels can vary in a number of possible combinations in the high oil com used as a raw material for meal and oil used in the invention. Acceptable amounts of moisture, oil, protein, starch, lysine, and tryptophan are illustrated in Table 1. However, additional combinations, such as 12 wt.% protein and 12 wt.% oil, not shown as indicated amounts in the table are within the scope and range of corn grain to be used to produce oil and meal used in the invention.
- Another suitable high oil com used as a raw material for preparing the com oil and corn meal used in the invention has a nutrient profile as shown in Table 2. Amounts are expressed on an "as is" or "as fed” moisture level. The amounts shown in Table 2 are exemplary for a com grain having 12 wt.% oil and 9 wt.% protein.
- Table 3 shows amino acid levels (based on a com grain moisture content of about 10%) of two high oil com grain samples and normal yellow com grain.
- the oil and protein levels of high oil com sample 1 (HOC 1) were 13.3 wt.% and 10.7 wt.% respectively, expressed on a dry matter basis.
- the oil and protein levels of high oil com sample 2 (HOC 2) were 13.0 wt.% and 11.2 wt.% respectively, expressed on a dry matter basis.
- normal yellow corn grain has about 4.2 wt.% oil and about 9.2 wt.% protein on a dry matter basis.
- High oil com is generally subjected to an extraction process as described herein to provide the enhanced corn oil and com meal to be included in the finished products of the invention.
- finished product or “product” refers to an article or manufacture made by combining the com oil and/or corn meal of the invention with a variety of other ingredients. The specific ingredients included in a product will be determined according to the ultimate use of the product.
- Exemplary products include animal feed, raw material for chemical modification, biodegradable plastic, blended food product, edible oil, cooking oil, lubricant, biodiesel, snack food, cosmetics, and fermentation process raw material.
- Products incorporating the meal described herein also include complete or partially complete swine, poultry, and cattle feeds, pet foods, and human food products such as extruded snack foods, breads, as a food binding agent, aquaculture feeds, fermentable mixtures, food supplements, sport drinks, nutritional food bars, multi- vitamin supplements, diet drinks, and cereal foods.
- more than one corn meal type can be made to meet certain nutritional requirements.
- the significance of this flexibility relates to the nutrient density within feed products and to dietary requirements of animals.
- One significant advantage of the use of this type of high oil com and extraction process is that an extracted com meal can be made to have a specific oil level depending on the extent of oil extraction.
- the remaining com meal has a nutrient density for protein, amino acids, and other nutrients not removed by the process, greater or different than normal com grain and greater than that of the starting corn, e.g., 12 wt.% oil, 9 wt.% protein.
- whole grain high oil corn is optionally tempered, optionally cracked, and then conditioned and flaked. After flaking, the flaked corn is extracted as described herein.
- Whole grain corn is optionally tempered before the extraction process.
- tempering is used interchangeably with the terms “heat soaking” or “steaming” and is a means to uniformly distribute the added moisture through the entire com kernel. Any tempering method known in the art is acceptable.
- the corn is steeped in an appropriate amount of water for any suitable length of time, such as at least 20 minutes, preferably at least 4 hours, preferably at least 6 hours, more preferably at least 12 hours, or most preferably at least 24 hours. After the corn has steeped for the desired length of time, its moisture content is retested.
- the com may be stored for short periods of time, but is preferably processed within 24 hours and most preferably processed immediately.
- Whole grain com is also optionally cracked.
- the whole high oil corn is cracked after tempering yet before conditioning.
- the high oil corn may be cracked by passing the whole grain corn between two rollers with corrugated teeth spinning toward each other spaced by a defined gap, and/or passing through a grind mill where a rotating toothed disk spins at an adjustable distance from a stationary disk, and/or the use of a hammermill where two rotating metal "hammer” like devices spinning next to one another.
- Methods for cracking com or high oil seeds are described in Watson, S.A. & P.E. Ramstad, ed. (1987, Com: Chemistry and Technology, Chapter 11, American Association of Cereal Chemist, Inc., St. Paul, MN), the disclosure ofwhich is hereby incorporated by reference in its entirety.
- a "cracked” corn is a corn that has undergone the above-described cracking process.
- conditioning refers to a process by which the com kernel is softened or plasticized to render it more pliable and amenable to the flaking and extraction processes. Conditioning may include the addition of steam (saturated and/or non-saturated steam) and/or water to the high oil corn. This is done by the use of a rotary conditioner. During the steam addition process, both the temperature and the moisture levels are elevated. The temperature ranges between about 140 °F and about 210 °F and the moisture is increased by about 1% to about 15%.
- the high oil corn grain is then flaked to any useful size.
- flaking refers to a process by which corn grain is passed one or more times through flaking rollers to produce flakes.
- the flaked corn may have a final flake thickness of about 5/1000 to 100/1000 of an inch ( ⁇ 0.12 mm to 2.0 mm) or preferably about 0.01 inches (0.25 mm), although other thicknesses may also be used.
- Useful flake thickness may depend on external limiting parameters such as the oil content of the com, the moisture content, the com type, e.g., dent or flint, and the oil extractor type.
- Suitable methods for flaking high oil corn are detailed herein and in D.R. Erickson, Practical Handbook of Soybean Processing Utilization (1995, AOCS Press), the entire disclosure ofwhich is hereby incorporated by reference. Suitable flaking methods also include those known to those of ordinary skill in the art of oilseed processing.
- the flaked corn is subjected to an extraction process to extract oil to form an extracted corn meal (ECM).
- ECM extracted corn meal
- Com oil is extracted from flaked grain by one or more extraction steps using any extraction method. Generally, substantially, or about all of the oil is extracted in a single extraction process.
- Useful extraction methods include solvent extraction, continuous solvent extraction, hydraulic pressing, expeller pressing, aqueous and/or enzyme extraction.
- Useful solvents for solvent extraction include, for example, all forms of commercially available pentane, hexanes, isopropyl alcohol, ethanol, supercritical carbon dioxide, combinations thereof, and other similar solvents.
- corn oil can be extracted from flaked grain using a hexane-based solvent extractor.
- Solvent extractors can include both percolation and immersion type extractors.
- a continuous solvent extraction process allows the flaked com to remain in contact with the solvent for at least 10 minutes, preferably at least 30 minutes, more preferably at least 60 minutes, and most preferably at least 90 minutes.
- Materials removed from solvent-based extractors include wet flakes and miscella.
- a miscella is a mixture of extracted oil and solvent.
- the wet flakes are the materials that remain after some or all of the solvent-soluble material has been extracted.
- Wet flakes also contain a quantity of solvent.
- Solvent is reclaimed from both the miscella and wet flakes using methods such as rising film evaporation, or drying, and raising the temperature using equipment such as flash tanks and/or de- solventiser/toasters. For example, heat is applied to the wet flakes or miscella under atmospheric pressure, under elevated pressure, or under vacuum to evaporate the solvent. The evaporated solvent is then condensed in a separate recovery system, and optionally dewatered and recycled to the extractor.
- cmde oil Desolventized miscella is commonly termed cmde oil, which can be stored and/or undergo further processing. Cmde oil can be refined to produce a final oil product. Methods for refining crude oil to obtain a final oil are known to those of ordinary skill in the art. Hui (1996) provides a thorough review of oils and oilseeds (Bailey's Industrial Oil and Fat Products, Fifth Ed., Vol. 2, Wiley and Sons, Inc., New York, 1996). Chapter three of Hui (pp. 125-158), the disclosure ofwhich is hereby incorporated by reference, specifically describes corn oil composition and processing methods. Crude oil isolated using the flaking methods described herein is of a high quality but can be further purified as needed using conventional oil refining methods.
- the present invention relates to a method of recovering lighter particles, such as fines, during the processing of high oil com.
- fines means any particle of the corn process that passes through a #18 sieve having a 1.00 mm opening as defined in ASTM E-l 1 specifications.
- the recovery of the particles may occur before, after, or during any step in the process, such as during the moisture removal step, during the cracking step or before or after the flaking process.
- fines are recovered by passing a current of gas (e.g., air, nitrogen, argon) over the corn at a suitable velocity and direction such that smaller and lighter particles are carried away in the stream, leaving behind larger and heavier particles.
- a current of gas e.g., air, nitrogen, argon
- lighter particles can be separated from heavier particles using a liquid spray (e.g., water, process water).
- the liquid is applied broadly enough so as to physically eliminate the lighter, airborne particles.
- the liquid spray can include components that add value to the end product, such as vitamins, minerals, enzymes, and combinations thereof.
- the liquid spray can further comprise a caustic liquid.
- these fine particles can be captured or recovered by any method known in the art such as using a baghouse.
- the recovered lighter particles can be reintroduced into starch-containing product streams for the recovery of starch. Additionally the fines may be sold as an animal feed.
- Com endosperm includes some valuable components such as carotenoids, lutein, and zeaxanthin.
- Carotenoids in grains are classified into two general groups, the carotenes and the xanthophylls.
- the carotenes are important because they are vitamin A precursors. Blessin et al. ⁇ Cereal Chemistry, 40, 582-586(1963)) found that over 90% of the carotenoids, ofwhich beta-carotene is predominant, are located in the endosperm of yellow dent com and less than 5% are located in the germ. Vitamin A is derived primarily from beta-carotene.
- tocotrienols Another group of valuable components found in the endosperm includes the tocotrienols. Grams et al. (1970) discovered that in com, tocotrienols were found only in the endosperm, whereas the germ contained most of the tocopherols. Tocotrienols can be extracted from plant material using various solvents. Processes for recovering tocotrienols from plant material are described by Lane et al. in U.S. Patent No. 5,908,940, the entire disclosure ofwhich is incorporated by reference.
- the process described herein provides a nutritionally enhanced corn oil enriched with lutein, zeaxanthin, and/or beta-carotene and optionally one or more other nutritional components.
- Oil-based products made with corn oil obtained by the extraction method described herein can contain higher levels of important nutrients than similar products made with corn oil produced by conventional methods.
- the corn oil obtained by the extraction methods described herein will include the corn oil from the germ and endosperm, and one or more other components extracted from the rest of the kernel.
- the one or more other components can be oil from the endosperm, tocotrienols, tocopherols, carotenoids, carotenes, xanthophylls, and sterols.
- Tocopherols (vitamin E) and vitamin A are antioxidants and fat-soluble vitamins. When included in the diet, both have demonstrated health benefits. Blending of oil of the present invention with other oils or substances to achieve an appropriate level of beta-carotene, vitamin E, and tocotrienols is deemed within the scope of the present invention.
- extracted corn oil prepared as described herein comprises about 0.1 wt.% to about 0.5 wt.% of tocopherol.
- Oil produced in accordance with the present invention also may include approximately a 200% to 300% increase in tocotrienol content over conventionally- produced crude corn oil.
- the corn oil was extracted and was then analyzed for tocotrienol content. The actual minimum and maximum values for tocotrienol content will depend upon the particular high oil corn used.
- the oxidative stability index (OSI), measured in hours, is a measure of an oil's relative stability toward oxidation. Generally, the greater the OSI, the less susceptible the oil is toward oxidation and the longer it takes to oxidize the oil under test or use conditions. In addition, the greater the content of unsaturated fatty acids present in the oil, the lower the OSI. Exemplary oils prepared according to the extraction method described herein generally possess OSI values ranging from about 10-22 hours.
- Exemplary embodiments of the crude oil obtained according to the extraction method described herein generally possess the partial composition profile featured in Table 4.
- Fatty acids generally found in the corn oil generally include palmitic, stearic, oleic, linoleic and linolenic acids.
- the crude oil prepared according to the methods described herein can be subsequently partially or completely hydrogenated. Suitable methods for partially or completely hydrogenating oil are described in D.R. Erickson, Practical Handbook of Soybean Processing Utilization (1995, AOCS Press), the entire disclosure ofwhich is hereby incorporated by reference.
- oils-based products can include conventional corn oil, soy oil, canola oil, olive oil, palm oil, sunflower oil, safflower oil, antioxidant, flavoring, hydrogenated oil, partially hydrogenated oil and/or animal fat.
- soy oil canola oil
- olive oil palm oil
- sunflower oil canola oil
- safflower oil antioxidant
- flavoring hydrogenated oil
- partially hydrogenated oil and/or animal fat By mixing the com oil herein with one or more other oils, blended oil products are made.
- the corn oil-based products can also include materials such as food additives, salt, fat, food colors, ⁇ -carotene, annatto extract, curcumin or tumeric, ⁇ -apo- 8'-carotenal and methyl and ethyl esters thereof, natural or synthetic flavors, antioxidants, propyl gallate, butylated hydroxytoluene, butylated hydroxyanisole, natural or synthetic tocopherols, ascorbyl palmitate, ascorbyl stearate, dilauryl thiodiproprionate, antioxidant synergists, citric acid, sodium citrate, isopropyl citrate, phosphoric acid, monoglyceride citrate, anti-foaming agent, dimethyl polysiloxane, crystallization inhibitor, oxystearin, amino acids, vitamin, minerals, carbohydrates, sugars, herbs, spices, acidity regulators, firming agents, enzyme preparations, flour treatment agents, viscosity control agents, enzymes, lipid
- An exemplary food product such as a breakfast cereal could include ingredients such as meal of the invention, wheat and oat flour, sugar, salt, corn syrup, milled corn, dried fruit, vitamin C, B vitamins, folic acid, baking soda, and flavorings.
- oil-based products that can comprise the oil prepared herein include food oil, cooking oil, edible oil and blended oil.
- Equipment used for the extraction of oil from oilseeds can be used to prepare the corn oil and extracted com meal described herein.
- Useful commercial-scale oilseed flakers can be obtained from French Oil Mill Machinery Company, Piqua, OH; Roskamp Champion, Waterloo, IA; Buhler, based in Switzerland with offices in Madison, MN; Bauermeister, Inc., Germany; Consolidated Process Machinery Roskamp Company, on the world wide web at http://www.cpmroskamp.com, and Crown Iron Works, Minneapolis, MN.
- commercial-scale methods and equipment are sufficient for extracting com oil from at least about 1 ton of com per day.
- the capacity of commercial-scale operations ranges from about 100 tons of com per day to about 3000 tons of corn per day, or the capacity ranges from about 700 tons of corn per day to about 1700 tons of corn per day.
- Commercial-scale operations that process greater than about 3000 tons of corn per day are also sufficient.
- Corn oil or com meal quality is determined by evaluating one or more quality parameters such as the oil yield, phosphorus content, free fatty acid percentage, the neutral starch percentage, protein content, and moisture content. Any method can be used to calculate one or more of the quality parameters for evaluating the oil or meal quality.
- the phosphorus concentration of cmde oil can be determined using AOCS method Ca 12-55.
- AOCS method Ca 12-55 identifies the phosphorus or the equivalent phosphatide zinc oxide, followed by the spectrophotometric measurement of phosphorus as a blue phosphomolybdic acid complex.
- AOCS method Ca 12-55 is applicable to cmde, degummed, and refined vegetable oils.
- the phosphoms concentration is converted to phospholipid concentration, i.e., gum concentration, by multiplying the phosphorus concentration by 30.
- com oil produced according to the invention includes about 100-400 ppm of phosphorus.
- the free fatty acid percentage of oil can be determined using AOCS method Ca 5a-40.
- AOCS method Ca 5a-40 identifies the free fatty acids existing in the oils sample.
- AOCS method Ca 5a-40 is applicable to all crude and refined vegetable oils, marine oils, and animal fats.
- the neutral oil loss during processing is determined by adding the gum percentage and the free fatty acid percentage together.
- the amount of free fatty acid obtained in the extracted corn oil will depend upon the amount of fatty acids found within the high oil com from which the oil was extracted. In some embodiments, the free fatty acid content of the extracted oil ranges from about 0.70 wt.% to 3.00 wt.%
- Oil color can be determined using AOCS method Cc 13b-45.
- AOCS method Cc 13b-45 identifies the color of an oil sample by comparing the oil sample with known color characteristics.
- AOCS method Cc 13b-45 is applicable to fats and oils provided no turbidity is present in the sample.
- Color values are evaluated qualitatively by visual inspection of the oil. Generally, visual inspection results in an oil being classified as a light oil or a dark oil compared to a known oil color. Color values are quantitated by determining a red color value and a yellow color value using the AOCS method Cc 13b- 45.
- cmde com oil isolated using conventional dry milling methods has a red color value ranging from about 7 to about 10 and a yellow color value ranging from about 60 to about 70.
- Com oils isolated using flaking methods described herein have oil colors that qualitatively are considered light and generally are lighter than cmde corn oil derived from wet or dry milling techniques.
- the yellow color values may range from about 60 to about 70 and red color values may range from about 7 to about 10, as determined by AOCS Method Cc 13b-93.
- the extracted corn oil can be used as a raw material for chemical modification, a component of biodegradable plastic, a component of a blended food product, a component of an edible oil or cooking oil, lubricant or a component thereof, biodiesel or a component thereof, a component of a snack food, a fermentation process raw material, and a component of cosmetics. Since the oil obtained by the extraction process herein has one or more components obtained from non-germ parts of the corn kernel, the oil is enhanced. In some embodiments, the oil will have an oleic range from about 20%) to 80%), or preferably 25% to 50%, whereas normal com has about 25% to 40% oleic acid in the oil. When making blended oils with the extracted oil, the blending can be done before, during or after the extraction process.
- Biodiesel can be produced using the extracted corn oil of the invention.
- Biodiesel is a general term used for a variety of ester-based oxygenated fuels.
- Biodiesel produced today is a mixture of fatty acid methyl esters produced by methylating refined vegetable oil. Refined oil is preferable to cmde oil or spent fryer oil due primarily to the quality of the glycerol by-product.
- the main drawbacks with previous biodiesel products and related vegetable oil lubricants are low temperature properties and reactivity toward oxidation and polymerization.
- a preferred biodiesel product comprises a low cloud point, reduced stearic and polyunsaturated fatty acid content, and high oleic acid content. Pour point correlates with low temperature properties and is influenced by the saturated fatty acid content of the oil. Polyunsaturated fatty acids are more susceptible to oxidation and polymerization reactions.
- Solvent-extracted corn (SEC) oil exhibits improved cloud point performance over soy while exhibiting similar chemical stability.
- SEC oil com can be further processed to form lubricants such as by published procedures practiced currently in the industry (see, e.g., U.S. Patent No. 6,174,501, incorporated herein).
- Meal produced from the flaking and oil extraction process described herein is used to produce unique feed products.
- the corn meal used herein has been obtained after extraction of oil from whole kernels of high oil com, wherein the kernel has not been separated into its constituent part, although the kernel may or may not have been ground, flaked, cracked, chipped, or abraded.
- the process of removing the oil from corn via extraction serves to concentrate the remaining nutrients such as protein and essential amino acids.
- Feed products containing predominantly corn meal produced by extraction require less supplementation with protein from other sources such as soybeans than feed products containing predominantly normal com grain.
- the meal by virtue of the composition arising from the processing method, offers feed manufacturers flexibility to produce feeds that could otherwise not be made.
- Animal feed rations having unique physical properties such as bulk density, texture, pelletability, and moisture holding capacity and/or unique nutritional properties are created by including the extracted com meal of the present invention as a component of said rations.
- the extracted corn meal isolated using flaking and extraction methods as described herein can, on its own, be a low- fat corn meal. Alternatively, it can be used in combination with other corn meals or nutritional components to make feed rations and food products.
- the extracted corn meal can also be combined with meals made from crops such as soybeans, canola, sunflower, oilseed rape, cotton, and other crops.
- the extracted corn meal can also be made from genetically modified corn and/or combined with meals made from transgenic oilseed grains to form an enhanced meal or enhanced product.
- the extracted corn meal can be provided as a loose product or a pelleted product, optionally in combination with other components.
- a pelleted product could include the extracted corn meal (by itself or in combination with other components) that has been pelleted and subsequently coated with zein protein.
- the corn meal can be included in blended meal products which can be provided in loose or pelleted form.
- the feed rations prepared with the extracted corn meal will generally meet the dietary and quality standards set forth in the CODEX ALIMENTARIUS or by the National Research Council.
- the com meal of the invention will generally comprise the components in the approximate amounts indicated in Table 6 below. Table 6
- the corn meals above may also further comprise unspecified amounts of the components for which no amounts have been indicated.
- Feed rations comprising different levels of nutrients are made by subjecting the high oil corn to different degrees of extraction, i.e., more oil is removed from the corn by subjecting it to extraction to a greater degree. Therefore, feed rations comprising the extracted corn meal of the invention can be made to include different amounts of fat, protein, and carbohydrates by controlling the extent to which the high oil corn is extracted.
- Table 7 details the amounts in which the indicated ingredients are present in animal feed rations comprising the extracted com meal, the specific inclusion range being indicative of exemplary rations in which extracted com meal is a main ingredient and the general inclusion range being indicative of rations in which one or more other ingredients, for example, carbohydrate-based energy sources such as sorghum, wheat, and/or other cereal grains or their by-products, or other non- cereal grain ingredients, may be included.
- carbohydrate-based energy sources such as sorghum, wheat, and/or other cereal grains or their by-products, or other non- cereal grain ingredients
- Meat and bone meal is obtained from suppliers such as Darling International, Inc. (Irving, TX).
- Oilseed meal is obtained from suppliers such as Cargill Oilseeds (Cedar Rapids, IA).
- Feather meal is obtained from suppliers such as Agri Trading Corp., (Hetchinson, MN).
- Amino acids are obtained from suppliers such as DuCoa, (Highland, IL).
- Feed rations are made by mixing various materials such as grains, seed meals, vitamins, and/or purified amino acids together to form a composite material that meets dietary requirements for protein, energy, fat, vitamins, minerals, and other nutrients.
- the mixing process can include grinding and blending the components to produce a relatively homogeneous mixture of nutrients. Physical ' properties of the feed raw materials and of the compounded feed affect the nutritional quality, storability, and overall value of the products. Suitable processes for manufacturing feed rations are disclosed in Feed Manufacturing Technology IV (1994, American Feed Industry Association) and incorporated herein in its entirety.
- the extracted corn meal may be somewhat analogous to steam- flaked corn in terms of digestibility of the starch fraction, but may have better digestibility in mminants by virtue of the processing conditions.
- specific oil levels can be achieved in the extracted meal by altering processing conditions.
- the protein, amino acid, and oil levels of the present extracted meal cannot be achieved in steam- flaked normal corn, and steam-flaked high oil corn may have too much oil, which could adversely affect mminant animal health.
- Extracted corn meal of the present invention has several advantages over normal com grain when used as an ingredient in aquaculture feed products.
- pigments such as carotenoids in feed are often deposited in fatty tissue when consumed resulting in an undesirable color.
- consumer preference is for very light colored tissue.
- consumer preference is for a pink or red tissue.
- An advantage of extracted com meal in aquaculture diets is that some undesired pigments will be reduced by virtue of the process to produce extracted corn meal; the solvent-soluble pigment compounds (such as carotenoids) are removed from the meal and concentrated in the oil.
- a second advantage of extracted corn meal over com dry-milled or wet-milled corn products is the improved protein content and quality, since the oil has been substantially removed from the kernel resulting in a meal product in which the protein has been concentrated. Because the meal is obtained from all portions of the kernel, including most or all of the embryo, the proteins are generally of higher quality and quantity than would be found in extracted corn grits. By including extracted corn meal in aquaculture feeds, it will be possible to raise animals with fewer undesirable pigment compounds in the tissue.
- Solvent extracted corn meal is also useful for fermentation-based production of compounds, such as, for example, ethanol, lactic acid, and vitamins.
- Solvent extracted corn meal from high oil corn can be hydrolyzed to provide soluble sugars.
- the meal serves as a carbon and nitrogen source for bacterial, fungal, or yeast cultures.
- Biotin and other vitamins can be produced through the cultivation of microorganisms.
- Organisms can include Pseudomonas mutabilis (ATCC 31014), Corymb acterium primorioxydans (ATCC 31015), Arthrobacter species, Gibberella species, Penicillium species, or combinations thereof.
- Nutrients used in the cultivation of these and other microorganisms include, for example, starch, glucose, alcohols, ketones, and as a nitrogen source, peptone, corn steep liquor, soybean powder, ammonium chloride, ammonium sulfate, ammonium nitrate, extracted corn meal, or urea.
- Various salts and trace elements may also be included in media for the culture of microorganisms.
- the pH of the culture medium is about 4 to about 9, preferably about 6 to about 8 and most preferably about 7 for bacterial species.
- the pH is about 5 to about 7 for mold or yeast.
- temperatures are kept between 10 °C to 100 °C, preferably between 20 °C to 80 °C, more preferably between about 20 °C to 40 °C, and most preferably about 25 °C.
- Biotin production is described in U.S. Patent No. 3,859,167, incorporated herein by reference.
- Cis-tetrahydro-2-oxo-4-n-pentyl-thieno[3,4-d]imidazoline is added to a culture medium containing solvent extracted corn meal and other appropriate identified ingredients in combination with a microbial species capable of forming biotin.
- the microorganism is cultivated for 1 to 10 days, preferably 1 to 8 days, and more preferably 2 to 7 days, after which time biotin is separated and purified.
- to purify biotin cells are removed from the culture medium, the filtrate is absorbed on activated charcoal, and purified with an ion exchange column.
- Alternative methods of purification are also used such as crystallization by adjusting the pH of the biotin-contained solution to near its isoelectric point.
- Solvent extracted corn meal can also be further processed to produce biodegradable materials.
- the meal of the present invention may be incorporated as a thermoplasticising agent.
- the meal of the invention may be included in the methods described in U.S. Patent No. 5,320,669, which is incorporated herein by reference.
- the thermoplastic material is prepared using solvent extracted com meal, as obtained from the process described herein.
- the biodegradable thermoplastic composition prepared using the meal of the present invention is treated with an organic solvent, and optionally a cross-linking agent, to link together the starch and protein of the extracted com grain.
- the cross-linking agent referred to herein may be any compound capable of linking the starch and the protein, such as, for example, an aldehyde, an acid anhydride or an epoxide.
- the compositions so formed using the meal of the present invention can be used to make extruded or molded articles that are biodegradable, water-resistant, and/or have a high level of physical strength.
- Blended products comprising the extracted com meal and one or more other oilseed meals are made by one or more of the following ways: 1) combining the high oil corn and the other oilseed prior to cracking and/or flaking and subjecting the entire seed mixture to the flaking and extraction process described herein to form a blended meal; 2) combining the high oil corn and the other oilseed after cracking and conditioning, but prior to flaking and subjecting the entire seed mixture to an extraction process as described herein to form a blended meal; 3) combining the high oil corn and the other oilseed after flaking and subjecting the entire seed mixture to the extraction process described herein to form a blended meal; 4) combining the extracted corn meal with extracted or non-extracted other oilseed meal to form a blended meal; or 5) combinations thereof to form a blended meal.
- additional components can be. added to the blended meals to form a blended product.
- the extracted corn meal can also be used in foodstuffs such as snack food, blended food products, breads, fermentation feedstock, breakfast cereals, thickened food products such canned fruit fillings, puffed or extruded foods, and porridge.
- foodstuffs such as snack food, blended food products, breads, fermentation feedstock, breakfast cereals, thickened food products such canned fruit fillings, puffed or extruded foods, and porridge.
- the extracted com meal can be combined with other components such as other meal, other oilseed meal, grain, other com, sorghum, wheat, wheat milled byproducts, barley, tapioca, corn gluten meal, com gluten feed, bakery byproduct, full fat rice bran, and rice hull.
- the extracted com meal can also be used as a raw material for production of com protein isolates, for fermentation, for further chemical processing, in addition enzymes, such as amylases and proteases, can be added to the meal to help facilitate the breakdown of starch and proteins.
- the extracted corn meal is optionally subjected to conventional methods of separating the starch and protein components.
- Such methods include, for example, dry milling, wet milling, high pressure pumping or cryogenic processes. These and other suitable processes are disclosed in Watson, S.A. & P.E. Ramstad, ed. (1987, Corn: Chemistry and Technology, Ch. 11 and 12, American Association of Cereal Chemist, Inc., St. Paul, MN), the disclosure ofwhich is hereby incorporated by reference. Due to the prior removal of oil from the com meal, the starch and protein components of the extracted com meal are separated from other components more easily than they would be if the com oil were not extracted.
- the moisture content of the grain can affect the flaking process. It may be necessary for the moisture of the corn grain to be increased by about 1% to about 15% before flaking the seed. Optimizing the grain moisture content to facilitate efficient processing is within the knowledge of those of ordinary skill in the art.
- Corn meals derived using different methods or isolated at different times are compared by normalizing the meals to a common moisture content.
- the moisture content of an oilseed protein concentrate such as a corn meal or whole corn, is determined using AOCS method Ba 2b-82.
- the crude fiber content of corn meal is determined using AOCS method Ba 6-84.
- AOCS method Ba 6-84 is useful for grains, meals, flours, feeds and all fiber bearing material from which the fat can be extracted leaving a workable residue.
- Cmde protein content of com meal is determined using AOCS method Ba 4e-93.
- the starch content of corn meal is determined using AOCS method Ba 4e-93.
- the starch content of com meal is determined using the Standard Analytical Methods of the Member Companies of the Corn Refiners Association Incorporated, 2d Edition, April 15, 1986, method A-20 ("Com Refiner's method A- 20").
- This example describes the process of obtaining corn oil and corn meal from high oil corn.
- a 45-pound sample of high oil corn was cracked using a Roskamp 6.5 Series (9" two sets) set at a roll gap of 0.27 inches.
- a sample was taken for analysis and the remaining sample split into 4 sub-samples.
- Each of the four sub-samples was then conditioned independently to different temperatures (120 °F, 150 °F, 180 °F, 200 °F).
- the samples were heated in a CrownTM 18 inch De-solventiser/Toaster. After each sample reached its conditioning temperature, the samples were passed through flaking rolls.
- the flaking rolls used were a Ross 10-inch set to a gap of 0.007 inches.
- a sample of the flakes was taken and about a 500 gram sample was extracted.
- the flaked sample was washed for four 20-minute periods with 1200 ml of hexanes each period for a total of 4800 ml of solvent over 80 minutes.
- the solvent temperature was about 120 °F.
- the miscella was collected and filtered through #4 qualitative circles each having a diameter of 185 mm. The filtered miscella was roto-evaporated to estimate the percent oil recovery.
- the meal was air dried at room temperature. Samples of the oil and meal were taken and analyzed for fatty acid profile, starch, protein and fiber. During the extraction a sieve analysis was performed and flake thickness was measured.
- the color of the crude oil was visually evaluated and determined to be a light yellow color compared to cmde oil isolated using conventional wet milling methods, which was a dark brown color.
- the desolventized corn meal was characterized using AOCS methods Ba 3- 38, Ba 2b-82, Ba 6-84, and Ba 4e-93, and Corn Refiner's Method A-20.
- the corn meal had about 3.2% fiber content, about 65% starch content, and about 14% protein content.
- Meal fat was determined to be about 1.07% using AOCS method 3-38.
- corn gluten feed created using conventional wet milling methods and normalized to a 10% moisture content can be expected to contain an oil content of about 4%, a protein content of about 20%, and a fiber and other carbohydrate content of about 60%.
- corn gluten meal created using conventional wet milling methods and normalized to a 10% moisture content can be expected to contain an oil content of about 3%, a protein content of about 60%, and a fiber and other carbohydrate content of about 22%.
- the extracted com meal described herein provides a greater amount of key nutritional components such as vitamins, folic acid, pantothenic acid, lysine, tryptophan, and/or niacin.
- Meal Samples 1 and 2 of extracted corn meal that are prepared above include the nutritional components in the amounts shown in Table 9. Amounts for the same components, to the extent they are found in yellow com that has not been processed as described herein, are included for comparison. Table 9
- the extracted corn meal prepared as described herein advantageously can be made to contain specific levels of oil and, in particular, specific ratios of oil to protein, of oil to carbohydrate or of oil to protein to carbohydrate.
- oil to protein for example, normal corn with 8 wt.% protein and 4 wt.% oil has a protei oil ratio of 2.0, and high oil corn with 9 wt.% protein and 12 wt.% oil has a protei oil ratio of 0.75.
- Meal produced by extraction to have 10.5 wt.% protein and 1.5 wt.% oil has a proteimoil ratio of 7.0. This higher ratio makes this meal type and products made from it desirable for certain applications, one example being a swine-finishing ration.
- the present invention provides an extracted corn oil with greater amounts of lutein, zeaxanthin and beta-carotene than commercially available crude oil obtained from commodity normal yellow #2 dent corn.
- Conventional crude oil can be obtained from suppliers such as Cargill, Incorporated (Minneapolis, MN).
- a corn oil prepared as described above comprised the ingredients shown in Table 10 in the amounts indicated as compared to commercially available cmde oil.
- This example details a comparison of two different feed rations: a first feed ration containing normal corn that has not been solvent extracted and a second feed ration containing extracted com meal.
- the feed ration containing extracted com meal is used when lean pork meat is a desired end product.
- a hog finishing feed ration comprising an extracted com meal containing less than or about 1.5 wt.% oil is prepared by providing the following ingredients in the amounts indicated in Table 11.
- the feed ration is generally produced by blending, mixing, and pelletting the ingredients to produce a feed product; however, one or more of these steps can be omitted in the process of preparing the feed ration.
- Table 11 shows a comparison of swine feed rations made using normal corn (not high oil com) and extracted corn meal obtained from high oil corn comprising 12 wt.% oil, 9 wt.% protein, wherein the extracted corn meal has about 1.5 wt.% or less of oil (fat). Amounts are expressed on an "as is" or "as fed” moisture level.
- Some advantages of the new feed ration are that a user of the meal would not need to grind the corn, thus saving an energy intensive step, less soybean or other oilseed meal is required to meet desired protein levels, and the meal may have better digestibility than corn grain.
- the feed ration of this example is used to fulfill the high-energy requirements of growing birds such as broilers.
- a poultry broiler finishing feed ration comprising an extracted corn meal containing less than or about 4 wt.% oil (fat) is prepared by providing the following ingredients in the amounts indicated in Table 12.
- the feed ration is generally produced by blending, mixing, and pelletting the ingredients to produce a feed product; however, one or more of these steps can be omitted in the process of preparing the feed ration.
- Table 12 shows the comparison of poultry feed rations made using normal com (not high oil corn) and extracted com meal obtained from high oil com comprising 12 wt.% oil, 9 wt.% protein, wherein the extracted corn meal has about 4 wt.% or less of oil (fat). Amounts are expressed on an "as is" or "as fed” moisture level and absolute values for ingredient percentages are given, however, in practice, the ingredients may be included using the inclusion rates shown in other tables herein.
- the tocotrienol content of extracted whole kernel oil (EWKO) samples from two different high oil corn samples that were extracted with solvent at temperatures ranging from 120 to 200 °F was found to be approximately two to three times higher than in the conventional crude oil sample.
- the tocotrienol content of the EWKO samples ranged from about 26 ppm to about 33 ppm of ⁇ -tocotrienol and from about 48 ppm to about 84 ppm of ⁇ -tocotrienol.
- increasing the extraction temperature results in an increase in the tocotrienol content of the extracted corn oil.
- the actual minimum and maximum values for tocotrienol content will depend upon the particular high oil corn used.
- Example 1 Accordingly, the process of Example 1 is used to make an extracted com oil comprising elevated levels of tocotrienols.
- This example illustrates a novel feed ingredient comprised of a blend of a com meal produced by the flaking and oil extraction method and another plant-based meal such as an oilseed meal.
- This blended material could be in the form of simply a loose aggregate mixture of both meal types or a pelletted product. Because the method for producing the com and oilseed meals would be similar, i.e., cracking, conditioning, flaking and solvent extraction, it is possible to produce both meals in proximity and blend them prior to shipment to a customer.
- An advantage of this approach is that varying protein and energy levels can be created in a single meal. Additional ingredients are optionally added either at the meal blending stage or at a later time. For example, an energy-intensive step in feed manufacturing involves grinding corn grain and blending it with other ingredients at a feed mill.
- the present blended meal generally requires less energy to produce a finished feed product than does a conventional blended meal.
- Table 14 shows nutrient profiles of soybean meal (SBM), extracted corn meal (ECM), a blend of 20% SBM and 80% ECM (S20-C80), a blend of 10% SBM and 90% ECM (S10-C90), and nutrient requirements for poultry and swine diets.
- SBM soybean meal
- ECM extracted corn meal
- S20-C80 a blend of 20% SBM and 80% ECM
- S10-C90 a blend of 10% SBM and 90% ECM
- Example 6 Processing High Oil Corn Using Flaking Method Shelled kernels of individual ears of yellow dent com were screened for a total oil content greater than about 7 wt.% oil using a PertenTM bulk near infrared (NIR) seed tester (model 9100-H.F) Perten Instruments (Reno, NV). Kernels from the ears having at least a 7 wt.% oil content were screened further for individual kernels having an oil content of at least 13 wt.% oil in a BrimroseTM seedmeister single kernel NIR tester (Brimrose Corp., Baltimore, MD). The kernels were stored at a moisture content of about 13.5%. At the time of processing, the moisture content of the seed was about 10%.
- NIR near infrared
- a bench scale flaking apparatus containing a two-inch stainless steel rod and plate was used to flake the whole com grain.
- the whole com grain sample was passed through the rollers four times to obtain a final flake thickness of about 0.01 inches.
- a miscella was extracted from the flaked corn grain using hot (60 °C to 65 °C) n-hexane and a KimbleTM model 585050 Soxhlet extractor.
- the resulting miscella and com meal were desolventized.
- the miscella was desolventized by heating the miscella to 70EC under a vacuum of 25 inches of mercury.
- the com meal was desolventized according to AOCS method Ba 2a-38.
- the total recovered oil was determined to be 14.74 wt.% of the whole corn grain sample.
- the phosphorus content of the desolventized crude oil was determined to be 365 ppm using AOCS method Ca 12-55.
- the phospholipid concentration was determined to be 1.095%) (0.0365% * 30).
- the free fatty acid content was determined to be 0.2% using AOCS method Ca 5a-40.
- the neutral oil loss during processing was determined to be 1.3% (1.095% + 0.2%).
- crude oil extracted from normal, i.e., 3-4 wt.% total oil content corn grain using conventional wet milling methods can be expected to have a phosphorus content from about 600 ppm to about 800 ppm, a free fatty acid concentration from about 0.5% to about 1.0% and a neutral oil loss during processing ranging from about 3% to about 4%.
- the color of the cmde oil was visually evaluated and determined to be a light yellow color compared to a cmde oil isolated using conventional wet milling methods, which was a dark brown color.
- corn meal had a 3.2%> fiber content, a 65% starch content, and a 14% protein content.
- Meal fat was determined to be 1.07% using AOCS method 3-38.
- corn gluten feed created using conventional wet milling methods and normalized to a 10% moisture content can be expected to contain an oil content of about 4%, a protein content of about 20%>, and a fiber and other carbohydrate content of about 60%.
- corn gluten meal created using conventional wet milling methods and normalized to a 10% moisture content can be expected to contain an oil content of about 3%, a protein content of about 60%, and a fiber and other carbohydrate content of about 22%.
- Example 7 Process of Refining High Oil Corn [0114] This example describes a continuous solvent extraction process in the context of the present invention. The extraction process consisted fundamentally of four parts: pre-extraction, extraction, meal desolventization, and oil desolventization. These various stages are described in further detail below.
- the tempered corn was cracked at ambient temperature using a RoskampTM (Waterloo, IA) model number 6.5 series double stand cracking roll having rolls with 9" diameters and 12" lengths. Both top and bottom rolls were set such that one roll rotated faster than the other. The fast rolls rotated at 1065 revolutions per minute (rpm) with 6 spiral RBV cut corrugations per inch. The slow rolls were cut identically but rotated at 708 rpm. Crack moistures were 13.3% to 15.7%.
- RoskampTM Waterloo, IA model number 6.5 series double stand cracking roll having rolls with 9" diameters and 12" lengths. Both top and bottom rolls were set such that one roll rotated faster than the other. The fast rolls rotated at 1065 revolutions per minute (rpm) with 6 spiral RBV cut corrugations per inch. The slow rolls were cut identically but rotated at 708 rpm. Crack moistures were 13.3% to 15.7%.
- the cracked com was then conditioned in a two-deck nominal 100- kilogram capacity conditioner (Simon-Rosedowns, currently owned by De Smet; Prins Boudewijnlaan 265; B-2650 EDEGEM; Antwerp) with sweep arm agitation (36 inches in diameter, 20 inches high per deck).
- the bottom deck was run full.
- Residence time in the sparged steam section was 55 minutes.
- the top deck crack depth was varied to achieve a residence time in the indirect heating section averaging 39 minutes and for a total residence time was 94 minutes.
- Sparge steam addition was a rate from 0 to 5 kg/hr.
- Conditioning exit moistures were in the range of 12.1% to 14.5%. Exit temperatures were in the range from 75 °C to 85 °C.
- a continuous 150 kg/hr CrownTM (Roseville, MN) model II pilot extractor was used to process the flaked corn.
- This pilot scale extractor utilized mixed hexanes as a solvent with 5 counter-current miscella wash zones and a tail wash section.
- Six-miscella recirculation pumps were utilized with fresh hexanes at 50 °C to 60 °C fed in the upper portion of the extractor.
- the dimensions of the extractor were 29 feet long, 7.8 inches wide, and 4.5 inches deep. Twenty-three of the 29-foot extractor feet was wetted, ofwhich 19.5 feet was subjected to washing.
- the average feed rate was approximately 75 kg/hr.
- the residence time was approximately 60 min.
- the solvent-to- meal ratios were adjusted between 0.75:1 and 1.33:1. Full miscella was sent to the oil desolventization system at 27 °C to 34 °C.
- C Meal Desolventization
- SchneckenTM Crown Iron Works, Roseville, MN steam jacketed conveyor
- SJC steam jacketed conveyor
- the SJC consisted of a hollow flight screw inside of a steam jacket (12 feet long, 10 inches in diameter). The open flight screw created a tumbling action as it conveyed the extracted material through the conveyor, thus ensuring that all material was exposed to the heated wall.
- a pneumatic controller regulated the amount of steam supplied to the jacket. The temperature at the outlet of the conveyor was monitored and used as the basis for the control of steam supplied to the jacket. Vapors from the conveyor were collected in the low vacuum condenser by the slight negative pressure developed by the system fan.
- a double-deck nominal 100 kg-capacity desolventizer and toaster (DT) with sweep arm agitation was utilized (36 inches in diameter, 20 inches high per deck). Steam sparge was piped through the top sweep arm only. Meal exit moistures ranged from 9.4% to 17.7%, and exit temperatures ranged from 57 °C to 104 °C. Hexanes recovered from the SJC and extractor were condensed, dewatered, and recycled to the extractor.
- Oil desolventization was executed using a rising film evaporator (RFE).
- RFE rising film evaporator
- This unit consisted of sixteen 1.5 cm diameter tubes inside a large jacket.
- the jacket was filled with steam, heating the tubes.
- the extract-laden liquid (normally oil in hexanes called miscella) was pumped into the bottom of the tubes. As it traveled up the inside of the tubes, steam heat caused the liquid to boil. The vapors held the liquid against the wall of the tube in a thin, rising film. At the top, the liquid and vapor were allowed to separate.
- the oil flowed into an overflow pipe to the oil stripper (OS), while the vapors were carried over to a condenser.
- the tubes were under vacuum so that the liquid boiled at a low temperature.
- the oil stripper was a disc and donut style distillation column.
- the liquid was spread out in a thin film over a disc and dripped down onto a donut back onto a disc allowing the oil to cascade down the column.
- steam was injected into the bottom of the stripper, which passed over the liquid film thereby removing the solvent remaining in the liquid.
- a steam jacket to keep the liquid and steam hot surrounded the disc and donut column.
- the oil stripper was also operated under vacuum. Hexanes recovered from the rising film evaporator and the OS were condensed, dewatered, and recycled to the extractor.
- Free fatty acids were analyzed by gas chromatography (GC) using a CP88 cyanopropyl column (100m X 0.265mm, 0.5mm film thickness) and a flame ionization detector as described in American Oil Chemist Society (AOCS) methods Ce lc-82, Ce 2-65, Cd 3a-94 and Cd lc-85.
- GC gas chromatography
- AOCS American Oil Chemist Society
- Tocopherols and tocotrienols were analyzed by high performance liquid chromatography (HPLC, Waters model number 2590) using a normal phase silica column with hexane-isopropanol as the mobile phase and detected using fluorescence detection (Waters model number 2690), according to the procedure described in AOCS Ce 8-89.
- Lutein was analyzed by HPLC using a C30 reverse phase column with water- acetonitrile mobile phase and detected with a UV detector.
- Table 15 presents a comparison of the oil composition obtained from high oil corn and yellow #2 corn. For comparison, the composition of oil from yellow #2 corn extracted in a corn wet milling process is also given. Table 15
- This example sets forth one method of recovering lighter particles, such as fines, generated during the moisture removal step from the processing of high oil corn.
- High oil com is cracked and flaked as described in Example 7.
- the whole flaked corn from the flaking process is heated to remove moisture using standard processing equipment such as Kice SSI zig-zag classifier model A2612, (Kice Inc., Wichita, KS).
- a controlled air stream is regulated such that the smaller and lighter particles are carried away, hence separating them from the heavier flakes.
- One such example of the controlled air stream is provided by a CrownTM multi-stage aspirating system operated at 2600 cubic feet per minute.
- the lighter particles are recovered by standard process equipment such as a baghouse.
- the recovered lighter particles are introduced into starch-containing product streams for the recovery of starch.
- Example 9 Method Of Recovering Lighter Particles During Cracking Step With Air
- This example sets forth one method of recovering lighter particles such as fines, generated during the cracking step from the processing of high oil corn.
- Whole kernels from a high oil corn are cracked using a standard cracking mill roller such as Roskamp 6.5 Series, (Waterloo, IA).
- a controlled air stream is directed to pass across the cracking mill roller, and the velocity of the air stream is regulated such that the smaller and lighter particles are carried away in the air stream, hence separating them from the heavier particles.
- One such example of the controlled air stream is provided by a CrownTM multi-stage aspirating system operated at 2600 cubic feet per minute.
- the lighter particles are recovered by standard process equipment such as a baghouse.
- the recovered lighter particles are introduced into starch-containing product streams for the recovery of starch.
- Example 10 Method Of Recovering Lighter Particles With Liquid Spray
- High oil com is processed as described in Example 7.
- the cracked corn prior to flaking and the corn flakes after the flaking process are sprayed or misted with a source of liquid providing broad enough coverage to physically eliminate the lighter, airborne particles.
- Water is used as the liquid.
- the liquid spray can be a substance that adds value to the resulting meal as well as recovers the value from the fines.
- the liquid spray is typically pure water, process water or water that has been supplemented with nutritional additives such as vitamins, enzymes or minerals.
- the liquid stream containing the particulates is carried away from the heavier particles in each case and is collected.
- the particulates are separated from the liquid using standard process equipment including a hydrocyclone or centrifuge.
- the recovered fines may be dried before further use.
- the recovered lighter particles are then introduced into starch-containing product streams for the recovery of starch.
- Com meal of the present invention is suspended in hexanes in a sealed container, at a 2:3 com meal: solvent weight ratio. The mixture is allowed to stand at room temperature without mixing for about 18 hours. The organic solvent is removed from the extracted corn meal, and the extracted corn meal residue is washed during filtering with an aliquot of hexanes in a 1:1 residue: solvent weight ratio. The residue is dried in a convection oven at 50 °C for 16 hours. The dried residue is sprayed with water with mixing until the moisture content of the residue is 10.7% to 11.3%.
- the solvent-treated extracted corn meal composition is molded into an ASTM standard dogbone article using a compression molding press (Wabash Metal Products, Inc. Wabash, IN) at 5000 psi, 140 °C to 160 °C for 10 minutes.
- the untreated corn meal composition is likewise combined with water to a 10.7% to 11.3% water content and molded into an ASTM standard dogbone article.
- the articles produced with the solvent- treated extracted com meal will exhibit significantly improved tensile properties as compared to non-solvent treated extracted com meal.
- corn meal of the present invention is separately suspended in aqueous ethanol (95%) at 1 :3 weight-ratio of meal to oil, and boiled for 2 hours with reflux and mechanical stirring.
- the meal is filtered and the residues are washed with ethanol (1 :1 residue: ethanol).
- the residues are dried, remoistened, and molded according to the procedure above.
- Tensile properties and water- absorption of the meal treated with ethanol at boiling temperature for a short 2 hour period would be similar to the meals treated at room temperature for an extended 18 hour period.
- Solvent extracted com meal of the present invention prepared as described herein is a rich source of starch for fermentation.
- One method to provide soluble sugars suitable for fermentation is to hydrolyze starch molecules, which are included in the solvent extracted corn meal.
- About 300 g of corn meal prepared according to the present invention was passed through a 1 mm screen and combined with 700 ml of 99 °C to 100 °C water and 0.5 ml ⁇ -amylase in a sealed container. The pH was adjusted to 5.9 with base. The mixture was stirred for 45 minutes and additional ⁇ -amylase enzyme was added. After an additional 45 minutes of incubation, the pH of the mixture is adjusted to 4.5 with acid.
- Free amino nitrogen was determined by the AOAC method (15 th ED. 1990. pg. 735). For comparison, cracked com grain was prepared and fermented in a manner similar to the extracted corn meal. The amount of dextrose liberated from starch by the milling process and the amount of available nitrogen in the corn samples are outlined in Table 16. YDM displayed the highest dextrose content and HOC the lowest.
- HOC high oil corn
- HOCM high oil corn meal
- YD, YDM, and HOCM cultures displayed similar dextrose utilization curves.
- HOC and HOCM cultures reached over 80 g/L ethanol, but stopped production after 19 hours, possibly due to the limitation of a necessary nutrient. None of the cultures reached the maximum theoretical ethanol yield of 50%, however YD cultures did achieve 45% yield followed by YDM at 43%, HOC at 41%) and HOCM at 38% (Table 17). The maximum ethanol yields are relatively close and perhaps minor growth condition adjustments account for the differences.
- Example 13 Aquaculture Feed Comprised Of Corn Meal Derived From High Oil Corn [0143] This example sets forth the use of extracted corn meal in an aquaculture feed product.
- Two feeding programs are used for two species of fish: tillapia and catfish.
- One feeding program utilizes a feed including corn grits produced from dry- milled yellow corn grain.
- the other feeding program utilizes a feed including ECM derived from high oil corn. Feeds are produced with the following ingredients (Table 18): Table 18.
- extracted com meal can be substituted for some or all of the com, some or all of the wheat middlings, and/or some of the soybean meal at various levels to produce a desired nutrient profile that can vary depending on the fish species to be fed.
- tillapia is fed feed containing extracted corn meal.
- a second group of tillapia is fed feed containing com grits.
- one group of catfish is fed feed containing extracted corn meal, and one group of catfish is fed feed- containing com grits.
- the experimental design included four ponds per treatment of one hundred fish per pond, for a total of sixteen ponds and 1,600 fish. Fish within species and ponds are of similar size and weight. Within each species and treatment, fish are fed amounts of feed necessary to support growth rates typical in commercial aquaculture production. Fish are raised from fingerling size to a suitable size reflective of typical market weights, for example, to about one and a half pounds.
- Example 14 Biodiesel Comprised Of Corn Oil Derived From High Oil Corn [0150] This example sets forth the use of oil from high oil corn as a source of an improved biodiesel fuel.
- the two phases of the reaction mixture are allowed to stand and separate to provide methyl esters in the upper phase, and a mixture of glycerol and approximately 10-15 wt.% residual methyl esters, methanol, and base in the lower phase.
- Approximately 6.4 kg/hr (14 lbs/hr) of the glycerol phase is neutralized, present methanol flashed off, and the remainder is sent to a continuously stirred reaction unit, operated at 80 °C and 320 psig.
- the reaction unit also contains approximately 4 wt.%) Amberlyst-15 catalyst with a residence time of 2 hours and approximately 7.9 kg/hr (17.5 lbs/hr) iso-butylene is fed to the reaction unit.
- the biodiesel fuel is produced at approximately 66 kg/hr (145 lbs/hr) and has a kinematic viscosity and cloud-point that is greater than biodiesel without glycerol ethers present.
Abstract
Description
Claims
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MXPA03001236A MXPA03001236A (en) | 2000-08-10 | 2001-08-10 | Products comprising corn oil and corn meal obtained from high oil corn. |
EP01962041A EP1307110A2 (en) | 2000-08-10 | 2001-08-10 | Products comprising corn oil and corn meal obtained from high oil corn |
JP2002519587A JP2004508816A (en) | 2000-08-10 | 2001-08-10 | Products containing corn oil and corn meal obtained from high oil corn |
BR0113214-8A BR0113214A (en) | 2000-08-10 | 2001-08-10 | Products comprising corn oil and cornmeal obtained from highly oily corn |
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US6703227B2 (en) | 1999-02-11 | 2004-03-09 | Renessen Llc | Method for producing fermentation-based products from high oil corn |
US6723370B2 (en) | 1999-02-11 | 2004-04-20 | Cargill, Incorporated | Products comprising corn oil and corn meal obtained from corn |
US6740508B2 (en) | 1999-02-11 | 2004-05-25 | Renessen Llc | Fermentation-based products from corn and method |
US7083954B2 (en) | 1999-02-11 | 2006-08-01 | Renessen Llc | Method of producing fermentation-based products from corn |
WO2008080495A1 (en) * | 2006-12-29 | 2008-07-10 | Ab Enzymes Gmbh | Improved method for recovering oil from plant seeds |
US9226515B2 (en) | 2004-02-03 | 2016-01-05 | Cargill, Incorporated | Protein concentrate and an aqueous stream containing water-soluble carbohydrates |
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US7083954B2 (en) | 1999-02-11 | 2006-08-01 | Renessen Llc | Method of producing fermentation-based products from corn |
US6648930B2 (en) | 1999-02-11 | 2003-11-18 | Renessen Llc | Products comprising corn oil and corn meal obtained from high oil corn |
US6703227B2 (en) | 1999-02-11 | 2004-03-09 | Renessen Llc | Method for producing fermentation-based products from high oil corn |
US6723370B2 (en) | 1999-02-11 | 2004-04-20 | Cargill, Incorporated | Products comprising corn oil and corn meal obtained from corn |
US6740508B2 (en) | 1999-02-11 | 2004-05-25 | Renessen Llc | Fermentation-based products from corn and method |
WO2003015535A1 (en) * | 2001-08-10 | 2003-02-27 | Renessen Llc | Products comprising corn oil and corn meal obtained from corn |
WO2003016441A1 (en) * | 2001-08-10 | 2003-02-27 | Renessen Llc | Corn oil processing and products comprising corn oil and corn meal obtained from corn |
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WO2008080495A1 (en) * | 2006-12-29 | 2008-07-10 | Ab Enzymes Gmbh | Improved method for recovering oil from plant seeds |
US8822201B2 (en) | 2006-12-29 | 2014-09-02 | Ab Enzymes Gmbh | Method for recovering oil from plant seeds |
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CN1468063A (en) | 2004-01-14 |
WO2002013624A8 (en) | 2003-09-12 |
AU2001283255A1 (en) | 2002-02-25 |
BR0017314A (en) | 2003-07-08 |
EP1307110A2 (en) | 2003-05-07 |
WO2002014459A3 (en) | 2002-08-22 |
AU2000266391A8 (en) | 2002-05-23 |
WO2002013624A1 (en) | 2002-02-21 |
BR0113214A (en) | 2003-07-15 |
EP1307111A1 (en) | 2003-05-07 |
CN1454056A (en) | 2003-11-05 |
AU2000266391A1 (en) | 2002-02-25 |
MXPA03001236A (en) | 2004-09-10 |
AR054147A2 (en) | 2007-06-06 |
SA00210496B1 (en) | 2007-02-03 |
MXPA03001240A (en) | 2004-09-10 |
PE20020306A1 (en) | 2002-04-27 |
EP1307111A4 (en) | 2005-06-15 |
JP2004508816A (en) | 2004-03-25 |
JP2004505645A (en) | 2004-02-26 |
UY26299A1 (en) | 2000-10-31 |
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