US3493508A - Organic compositions containing metal salts of reaction product of an alkyl phenol and an ethyleneamine - Google Patents

Organic compositions containing metal salts of reaction product of an alkyl phenol and an ethyleneamine Download PDF

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US3493508A
US3493508A US654327A US3493508DA US3493508A US 3493508 A US3493508 A US 3493508A US 654327 A US654327 A US 654327A US 3493508D A US3493508D A US 3493508DA US 3493508 A US3493508 A US 3493508A
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grams
mol
metal salts
ethyleneamine
organic compositions
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US654327A
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Harry J Andress Jr
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ExxonMobil Oil Corp
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Mobil Oil Corp
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    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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Definitions

  • This invention relates to organic compositions and, in one of its aspects, relates more particularly to improved organic compositions in the form of liquid and solid hydrocarbons which, in the form of fuel oils, normally cause screen clogging or emit smoke upon combustion or, when in the form of lubricating oils or greases, are subject to oxidative deterioration. Still more particularly, in this aspect, the invention relates to improved organic compositions in the form of petroleum distillate hydrocarbon fuels, lubricating oils or greases which, in their uninhibited state, tend to result in the above-described deleterious conditions in the course of use or storage.
  • the present invention in its preferred applications contemplates organic compositions of the abovedescribed types which contain a small amount of the aforementioned metal salts, usually from about .001 percent to about 10 percent, by weight, and preferably from about .01 percent to about 0.5 percent, by weight, of the total of such compositions.
  • the organic compositions improved in accordance with the present invention may comprise any materials that are normally susceptible to the above-described screen clogging, smoke emission or oxidative deterioration characteristics.
  • a field of specific applicability is the improvement of liquid hydrocarbons boiling from about 75 F. to about 1000 F.
  • Of particular significance is the treatment of petroleum distillate fuel oils having an initial boiling 3,493,508 Patented Feb. 3, 1970 point from about F. to about 135 F. and an end boiling point from about 250 F. to about 750 F.
  • distillate fuel oils is not intended to be restricted to straight-run distillate fractions.
  • distillate fuel oils can be straightrun distillate fuel oils, catalytically or thermally cracked (including hydrocracked) distillate fuel oils, or mixtures of straight-run distillate fuel oils, napthas and the like, with cracked distillate stocks.
  • fuel oils can be treated in accordance with well-known commercial methods, such as acid or caustic treatment, hydrogenation, solvent-refining, clay treatment and the like.
  • distillate fuel oils are characterized by their relatively low viscosity, pour point and the like.
  • the principal property which characterizes these hydrocarbons, however, is their distillation range. As hereinbefore indicated, this range will lie between about 75 F. and about 750 F. Obviously, the distillation range of each individual fuel oil will cover a narrower boiling range, falling nevertheless within the above-specified limits. Likewise, each fuel oil will boil substantially, continuously throughout its distillation range.
  • fuel oils are Nos. 1, 2, and 3 fuel oils, used in heating and as diesel fuel oils, gasoline, turbine oil, and jet combustion fuels.
  • the domestic fuel oils generally conform to the specifications set forth in ASTM Specification D396-48T.
  • Specifications for diesel fuels are defined in ASTM Specification D975 48T.
  • Typical jet fuels are defined in Military Specification MIL-F-5624B.
  • hydrocarbon lubricating oils of varying viscosity and pour points, falling both Within the aforementioned range and as high as 1000 F. or higher, may also be effectively treated through the use of the aforementioned metal salts.
  • the aforementiond metal salts of the present invention may also be incorporated as antioxidants in grease compositions.
  • Such greases may comprise a combination of a Wide variety of lubricating vehicles and thickening or gelling agents.
  • greases in which the aforementioned metal salts are particularly effective may comprise any of the conventional hydro carbon oils of lubricating viscosity, as the oil vehicle. and may include mineral or synthetic lubricating oils, aliphatic phosphates, esters and di-esters, silicates, siloxanes and oxalkyl ethers and esters.
  • Mineral lubricating oils, employed as the lubricating vehicle may be of any suitable lubricating viscosity range from about 45 SSU at 100 F.
  • oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about are preferred. The average molecular weights of these oils may range from about 250 to about 800.
  • the lubricating oil is employed in the grease composition in an amount sufficient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • the oil vehicles employed in the novel grease formulations of the present invention may comprise mineral or synthetic oils of lubricating viscosity.
  • mineral oils having a viscosity of at least 40 SSU at F., and particularly those falling Within the range from about 60 SSU to about 6,000 SSU at 100 F., may be employed.
  • synthetic vehicles are employed rather than mineral oils, or in combination therewith, as the lubricating vehicle, various compounds of this type may be successfully utilized.
  • Typical synthetic vehicles include: polypropylene, polypropylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethyl hexyl) sebacate, di(2-ethyl hexyl) adipate, di-butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (poly-siloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (p-phenoxy phenyl) ether, phenoxy phenyl ethers, etc.
  • the lubricating vehicles of the aforementioned improved greases of the present invention containing the above-described metal salts as additives are combined with a grease-forming quantity of a thickening agent.
  • a thickening agent may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in such degree as to impart to the resulting grease composition the desired consistency.
  • Other thickening agents that may be employed in the grease formulation may comprise the non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
  • grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other respects, any material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease can be used in preparing the aforementioned improved grease in accordance with the present invention.
  • the metal salts of the present invention may be prepared, in general, by reacting an alkyl phenol, an ethyleneamine and a metal oxide at a temperature from about 50 C. to about 250 C., and preferably at a temperature from about 150 C. to about 250 C., to produce a reaction product which is incorporated as an improving agent in the aforementioned organic compositions.
  • the mechanism of the reaction or the structure of the reaction product produced is not known. During the reaction, it is found that water is evolved. It is theorized that the metal may possibly be present in a chelate form in the final product.
  • the alkyl phenol reactant may be of any type or chain length, either substituted or unsubstituted.
  • the alkyl phenol may include such compounds as didodecylphenol, monododecylphenol, monopolybutylene alkylated phenol and monononylphenol.
  • the ethyleneamine reactant may be of any type or chain length, either substituted or unsubstituted.
  • the ethyleneamine may include such compounds as ethylenediamine, N-hydroxyethylethylene diamine, triethylene tetramine, tetraethylene pentamine, tetrahydroxyethyl ethylene diamine and N-dodecyldiethylene triamine.
  • the metal oxide reactant may be employed in the form of a monoxide, dioxide and higher oxides, hydroxides, hydroxide monohydrates and other oxides.
  • the term metal oxide is intended to denote not only the oxide, per se, but other forms of oxygen-containing compounds of the type described.
  • the metal of these oxides may include a wide variety of metallic elements, and preferably those selected from the group consisting of calcium, zinc, barium, lithium and potassium.
  • EXAMPLE 1 215 grams (0.5 mol) of didodecylphenol, 215 grams of a diluent comprising a 100" refined pale paraffin oil, 18.5 grams (0.25 mol) calcium hydroxide and 15 grams (0.25 mol) of ethylene diamine were stirred at a temperature of approximately -80" C. for a period of about two hours, and then slowly heated to a temperature of about 250 C. to produce a hydrocarbon soluble product which contained, by Weight, 1.7% nitrogen and 1.0% calcium.
  • EXAMPLE 2 131 grams (0.5 mol) of monododecylphenol, 131 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide and 27 grams (0.25 mol) of N-hydroxyethylethylene diamine were slowly heated with stirring to a temperature of about 175 C. over a period of about six hours. Upon analysis, the resulting product was found to contain, by weight, 2.0% nitrogen and 3.64% calcium.
  • EXAMPLE 3 262 grams (1 mol) of monododecylphenol, 200 grams of the diluent employed in Example 1, 37 grams (0.5 mol) of calcium hydroxide, 36.5 grams (0.25 mol) of triethylene tetramine and 4 grams of water were stirred at a temperature of about C. for a period of about ten hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 2.8% nitrogen and 2.5% calcium.
  • EXAMPLE 4 131 grams (0.5 mol) of monododecylphenol, 135 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide, 18.9 grams (0.1 mol) of tetramethylene pentamine and 2 grams of water were slowly heated with stirring to a temperature of about 250 C. over a period of about six hours. Upon analysis, the resulting product was found to contain, by weight, 2.5 nitrogen and 3.22% calcium.
  • EXAMPLE 5 131 grams (0.5 mol) of monododecylphenol, 131 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide and 60 grams (0.25 mol) of tetrahydroxyethyl ethylene diamine were slowly heated with stirring to a temperature of about 250 C. Upon analysis, the resulting product was found to contain, by weight, 2.0% nitrogen and 2.93% calcium.
  • EXAMPLE 7 210 grams (0.8 mol) of monododecylphenol, 32 grams (0.43 mol) of calcium hydroxide, 230 grams (0.85 mol) of N-dodecyldiethylene triamine and 20 grams of water were stirred at a temperature of 90 C. for a period of about four hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 8% nitrogen and 2.86% calcium.
  • EXAMPLE 8 410 grams (0.4 mol) of a monopolybutylene alkylated phenol, 28 grams (0.5 mol) of calcium hydroxide, 30 grams (0.5 mol) of ethylenediamine and grams of water were stirred at a temperature of 90 C. for a period of about three hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 3.0% nitrogen and 0.6% calcium.
  • EXAMPLE 9 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine, 21 grams (0.25 mol) of zinc oxide and 220 grams of xylene as a diluent were stirred at a temperature of 100 C. for a period of about four hours and then at 140 C. for a period of about three hours. Upon analysis, the resulting product was found to contain, by weight, 5.0% nitrogen and 3.2% zinc.
  • EXAMPLE 10 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine, 42 grams (0.25 mol) of barium dioxide and grams of water were stirred at a temperature of 105 C. for a period of about siX hours and then slowly heated to a temperature of about 175 C. 220 grams of xylene as a diluent were added. Upon analysis, the resulting product was found to contain, by weight, 5.1% nitrogen and 6.7% barium.
  • EXAMPLE 11 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine and grams (0.5 mol) of lithium hydroxide monohydrate were stirred at a temperature of about 105-110 C. for a period of about four hours. Upon analysis, the resulting product was found to contain, by weight, 9.0% nitrogen and 0.63% lithium.
  • EXAMPLE 14 An attempt was made to react a cyclic ethyleneamine, viz piperazine, with dodecylphenol and calcium hydroxide. No reaction was found to occur.
  • EXAMPLE 15 An attempt was made to react 1,3-propanediamine with dodecylphenol and calcium hydroxide. No reaction was found to occur.
  • the anti-screen clogging characteristics of organic compositions in the form, for example, of fuel oils having incorporated therein the novel metal salts of the present invention were determined from a standard screen clogging test, as described in US. Patent 3,296,130, issued Jan. 3, 1967. In general, this test is conducted using a Sundstrand V3 or S1 home fuel oil burner pump with a self-contained 100-mesh Monel metal screen. About 0.05 percent, by weight, of naturally-formed fuel oil sediment, composed of fuel oil, water, dirt, rust and organic sludge is mixed with 10 liters of the fuel oil. This mixture is circulated by the pump through the screen for 6 hours.
  • the sludge deposit on the screen is washed off with normal pentane and filtered through a tared Gooch crucible. After drying, the material in the Gooch crucible is washed with a 5050 (volume) acetone-methanol mixture. The total organic sediment is obtained by evaporating the pentane and the acetone-methanol filtrates. Drying and weighing the Gooch crucible yields the amount of inorganic sediment. The sum of the organic and inorganic deposits on the screen can be reported in milligrams recovered or converted into percent screen clogging.
  • test fuel oils comprising a blend of 60 percent distillate stock obtained from continuous catalytic cracking and 40 percent straight-run distillate stock, having a boiling range of between about 320 F. and about 640 F., and typical of No. 2 fuel oils.
  • Each blend was subjected to the above-described screen clogging test. The test results obtained are set forth in the following Table I.
  • the metal salts of the present invention are effective as improving agents in various types of organic compositions
  • these additives are effective as improving agents with respect to other specific types of organic compounds, such as fuel oils in the form of gasolines, and more specifically, to the treatment of such hydrocarbons as petroleum distillate fuels. They are also effective as stabilizers for hydrocarbon and synthetic lubricants of various types.
  • An organic composition present in major proportion and selected from the group consisting of liquid hydrocarbon fuels and hydrocarbon lubricants, containing, in an amount suflicient to act as an improving agent, a metal salt of the reaction product of an alkyl phenol and at least one member selected from the group consisting of ethylene polyarnines and their hydrocarbon and hydroxy substituted derivatives wherein the metal of said metal salt is selected from the group consisting of calcium, zinc, barium, lithium and potassium and the reactant components of said improving agent are employed in stoichiometric proportions.
  • composition as defined in claim 1 wherein said composition is a liquid hydrocarbon having a boiling range from about 75 F. to about 1000 F.
  • composition as defined in claim 1 wherein said composition is a liquid hydrocarbon comprising a petroleum distillate fuel oil having an initial boiling point 8 from about F to about F. and an end boiling point from about 250 F. to about 750 F.
  • alkyl phenol is selected from the group consisting of didodecylphenol, monododecylphenol, monopolybutylene alkylated phenol and monononylphenol.

Description

United States Patent ORGANIC COMPOSITIONS CONTAINING METAL SALTS OF REACTION PRODUCT OF AN ALKYL PHENOL AND AN ETHYLENEAMINE Harry J. Andress, Jr., Pitman, N.J., assignor to Mobil Oil Corporation, a corporation of New York No Drawing. Filed July 19, 1967, Ser. No. 654,327 Int. Cl. Cm 7/52, 3/48, l/54 US. Cl. 25242.7 13 Claims ABSTRACT OF THE DISCLOSURE Organic compositions are provided containing as improving agents metal salts of the reaction product of an alkyl phenol and an ethyleneamine. These metal salts act as anti-screen clogging agents and smoke suppressants for fuel oils and as stabilizers for lubricating oils and greases. The metal of these metal salts is selected from the group consisting of calcium, zinc, barium, lithium and potassium.
BACKGROUND OF THE INVENTION Field of the invention This invention relates to organic compositions and, in one of its aspects, relates more particularly to improved organic compositions in the form of liquid and solid hydrocarbons which, in the form of fuel oils, normally cause screen clogging or emit smoke upon combustion or, when in the form of lubricating oils or greases, are subject to oxidative deterioration. Still more particularly, in this aspect, the invention relates to improved organic compositions in the form of petroleum distillate hydrocarbon fuels, lubricating oils or greases which, in their uninhibited state, tend to result in the above-described deleterious conditions in the course of use or storage.
Description of the prior art It is well known that certain types of organic compositions in the form of liquid hydrocarbon fuels normally cause screen clogging or can emit smoke upon combustion. Furthermore, it is also known that organic compositions, when employed in the form of lubricating oils or greases containing such oils as vehicles, are subject to oxidative deterioration in the course of their functional environments, thus clearly indicating the necessity for incorporating into such organic compositions effective im proving agents.
SUMMARY OF THE INVENTION It has now been found that the aforementioned screen clogging, smoke emission or oxidative deterioration properties of organic compositions, particularly in the form of fuels and lubricants, can be effectively overcome by incorporating therein small amounts of a metal salt of the reaction product of an alkyl phenol and an ethyleneamine.
In general, the present invention in its preferred applications contemplates organic compositions of the abovedescribed types which contain a small amount of the aforementioned metal salts, usually from about .001 percent to about 10 percent, by weight, and preferably from about .01 percent to about 0.5 percent, by weight, of the total of such compositions.
The organic compositions improved in accordance with the present invention may comprise any materials that are normally susceptible to the above-described screen clogging, smoke emission or oxidative deterioration characteristics. A field of specific applicability is the improvement of liquid hydrocarbons boiling from about 75 F. to about 1000 F. Of particular significance is the treatment of petroleum distillate fuel oils having an initial boiling 3,493,508 Patented Feb. 3, 1970 point from about F. to about 135 F. and an end boiling point from about 250 F. to about 750 F. It should be noted, in this respect, that the term distillate fuel oils is not intended to be restricted to straight-run distillate fractions. These distillate fuel oils can be straightrun distillate fuel oils, catalytically or thermally cracked (including hydrocracked) distillate fuel oils, or mixtures of straight-run distillate fuel oils, napthas and the like, with cracked distillate stocks. Moreover, such fuel oils can be treated in accordance with well-known commercial methods, such as acid or caustic treatment, hydrogenation, solvent-refining, clay treatment and the like.
The distillate fuel oils are characterized by their relatively low viscosity, pour point and the like. The principal property which characterizes these hydrocarbons, however, is their distillation range. As hereinbefore indicated, this range will lie between about 75 F. and about 750 F. Obviously, the distillation range of each individual fuel oil will cover a narrower boiling range, falling nevertheless within the above-specified limits. Likewise, each fuel oil will boil substantially, continuously throughout its distillation range.
Particularly contemplated among the fuel oils are Nos. 1, 2, and 3 fuel oils, used in heating and as diesel fuel oils, gasoline, turbine oil, and jet combustion fuels. The domestic fuel oils generally conform to the specifications set forth in ASTM Specification D396-48T. Specifications for diesel fuels are defined in ASTM Specification D975 48T. Typical jet fuels are defined in Military Specification MIL-F-5624B. In addition, as previously indicated, hydrocarbon lubricating oils of varying viscosity and pour points, falling both Within the aforementioned range and as high as 1000 F. or higher, may also be effectively treated through the use of the aforementioned metal salts.
As previously indicated, the aforementiond metal salts of the present invention may also be incorporated as antioxidants in grease compositions. Such greases may comprise a combination of a Wide variety of lubricating vehicles and thickening or gelling agents. Thus, greases in which the aforementioned metal salts are particularly effective, may comprise any of the conventional hydro carbon oils of lubricating viscosity, as the oil vehicle. and may include mineral or synthetic lubricating oils, aliphatic phosphates, esters and di-esters, silicates, siloxanes and oxalkyl ethers and esters. Mineral lubricating oils, employed as the lubricating vehicle, may be of any suitable lubricating viscosity range from about 45 SSU at 100 F. to about 6,000 SSU at 100 F., and, preferably, from about 50 to about 250 SS=U at 210 F. These oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about are preferred. The average molecular weights of these oils may range from about 250 to about 800. The lubricating oil is employed in the grease composition in an amount sufficient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
As previously indicated, the oil vehicles employed in the novel grease formulations of the present invention, in which the aforementioned metal salts are incorporated as anti-oxidative or anti-corrosive agents, may comprise mineral or synthetic oils of lubricating viscosity. When high temperature stability is not a requirement of the finished grease, mineral oils having a viscosity of at least 40 SSU at F., and particularly those falling Within the range from about 60 SSU to about 6,000 SSU at 100 F., may be employed. In instances where synthetic vehicles are employed rather than mineral oils, or in combination therewith, as the lubricating vehicle, various compounds of this type may be successfully utilized. Typical synthetic vehicles include: polypropylene, polypropylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethyl hexyl) sebacate, di(2-ethyl hexyl) adipate, di-butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (poly-siloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (p-phenoxy phenyl) ether, phenoxy phenyl ethers, etc.
The lubricating vehicles of the aforementioned improved greases of the present invention containing the above-described metal salts as additives are combined with a grease-forming quantity of a thickening agent. For this purpose, a wide variety of materials may be employed. These thickening or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in such degree as to impart to the resulting grease composition the desired consistency. Other thickening agents that may be employed in the grease formulation may comprise the non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials. In general, grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other respects, any material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease can be used in preparing the aforementioned improved grease in accordance with the present invention.
The metal salts of the present invention may be prepared, in general, by reacting an alkyl phenol, an ethyleneamine and a metal oxide at a temperature from about 50 C. to about 250 C., and preferably at a temperature from about 150 C. to about 250 C., to produce a reaction product which is incorporated as an improving agent in the aforementioned organic compositions. The mechanism of the reaction or the structure of the reaction product produced is not known. During the reaction, it is found that water is evolved. It is theorized that the metal may possibly be present in a chelate form in the final product.
The alkyl phenol reactant may be of any type or chain length, either substituted or unsubstituted. Thus, the alkyl phenol may include such compounds as didodecylphenol, monododecylphenol, monopolybutylene alkylated phenol and monononylphenol.
The ethyleneamine reactant may be of any type or chain length, either substituted or unsubstituted. Thus, the ethyleneamine may include such compounds as ethylenediamine, N-hydroxyethylethylene diamine, triethylene tetramine, tetraethylene pentamine, tetrahydroxyethyl ethylene diamine and N-dodecyldiethylene triamine.
The metal oxide reactant may be employed in the form of a monoxide, dioxide and higher oxides, hydroxides, hydroxide monohydrates and other oxides. The term metal oxide is intended to denote not only the oxide, per se, but other forms of oxygen-containing compounds of the type described. The metal of these oxides may include a wide variety of metallic elements, and preferably those selected from the group consisting of calcium, zinc, barium, lithium and potassium.
DESCRIPTION OF SPECIFIC EMBODIMENTS The following data and examples will serve to illustrate the preparation of the novel metal salts of the present invention and their efiicacy as improving agents in organic compositions. It will be understood, however, that it is not intended the invention be limited to the particular metal salts or the particular organic compositions containing these salts, as described. Various modifications of these metallic salts and organic compositions, as previously indicated, can be employed and will be readily apparent to those skilled in the art.
EXAMPLE 1 215 grams (0.5 mol) of didodecylphenol, 215 grams of a diluent comprising a 100" refined pale paraffin oil, 18.5 grams (0.25 mol) calcium hydroxide and 15 grams (0.25 mol) of ethylene diamine were stirred at a temperature of approximately -80" C. for a period of about two hours, and then slowly heated to a temperature of about 250 C. to produce a hydrocarbon soluble product which contained, by Weight, 1.7% nitrogen and 1.0% calcium.
EXAMPLE 2 131 grams (0.5 mol) of monododecylphenol, 131 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide and 27 grams (0.25 mol) of N-hydroxyethylethylene diamine were slowly heated with stirring to a temperature of about 175 C. over a period of about six hours. Upon analysis, the resulting product was found to contain, by weight, 2.0% nitrogen and 3.64% calcium.
EXAMPLE 3 262 grams (1 mol) of monododecylphenol, 200 grams of the diluent employed in Example 1, 37 grams (0.5 mol) of calcium hydroxide, 36.5 grams (0.25 mol) of triethylene tetramine and 4 grams of water were stirred at a temperature of about C. for a period of about ten hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 2.8% nitrogen and 2.5% calcium.
EXAMPLE 4 131 grams (0.5 mol) of monododecylphenol, 135 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide, 18.9 grams (0.1 mol) of tetramethylene pentamine and 2 grams of water were slowly heated with stirring to a temperature of about 250 C. over a period of about six hours. Upon analysis, the resulting product was found to contain, by weight, 2.5 nitrogen and 3.22% calcium.
EXAMPLE 5 131 grams (0.5 mol) of monododecylphenol, 131 grams of the diluent employed in Example 1, 18.5 grams (0.25 mol) of calcium hydroxide and 60 grams (0.25 mol) of tetrahydroxyethyl ethylene diamine were slowly heated with stirring to a temperature of about 250 C. Upon analysis, the resulting product was found to contain, by weight, 2.0% nitrogen and 2.93% calcium.
EXAMPLE 7 210 grams (0.8 mol) of monododecylphenol, 32 grams (0.43 mol) of calcium hydroxide, 230 grams (0.85 mol) of N-dodecyldiethylene triamine and 20 grams of water were stirred at a temperature of 90 C. for a period of about four hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 8% nitrogen and 2.86% calcium.
EXAMPLE 8 410 grams (0.4 mol) of a monopolybutylene alkylated phenol, 28 grams (0.5 mol) of calcium hydroxide, 30 grams (0.5 mol) of ethylenediamine and grams of water were stirred at a temperature of 90 C. for a period of about three hours and then slowly heated to a temperature of about 225 C. Upon analysis, the resulting product was found to contain, by weight, 3.0% nitrogen and 0.6% calcium.
EXAMPLE 9 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine, 21 grams (0.25 mol) of zinc oxide and 220 grams of xylene as a diluent were stirred at a temperature of 100 C. for a period of about four hours and then at 140 C. for a period of about three hours. Upon analysis, the resulting product was found to contain, by weight, 5.0% nitrogen and 3.2% zinc.
EXAMPLE 10 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine, 42 grams (0.25 mol) of barium dioxide and grams of water were stirred at a temperature of 105 C. for a period of about siX hours and then slowly heated to a temperature of about 175 C. 220 grams of xylene as a diluent were added. Upon analysis, the resulting product was found to contain, by weight, 5.1% nitrogen and 6.7% barium.
EXAMPLE 11 220 grams (1 mol) of monononylphenol, 73 grams (0.5 mol) of triethylene tetramine and grams (0.5 mol) of lithium hydroxide monohydrate were stirred at a temperature of about 105-110 C. for a period of about four hours. Upon analysis, the resulting product was found to contain, by weight, 9.0% nitrogen and 0.63% lithium.
Comparative examples In order to illustrate the specific criticality of the ethyleneamine component in the reaction mixture for producing the novel metal salts of the present invention, the following comparative data was obtained.
EXAMPLE l2 1 mol of monododecylphenol, 0.33 mol of dipropylene triamine (iminobispropylamine) and 0.5 mol of calcium hydroxide were stirred to a temperature of about 200 C. It was found that no reaction product was formed and the calcium hydroxide remained unreacted.
EXAMPLE 13 An attempt was made to react calcium hydroxide in varying amounts with alkyl phenols in the absence of ethyleneamine compounds. No reaction was found to occur.
EXAMPLE 14 An attempt was made to react a cyclic ethyleneamine, viz piperazine, with dodecylphenol and calcium hydroxide. No reaction was found to occur.
EXAMPLE 15 An attempt was made to react 1,3-propanediamine with dodecylphenol and calcium hydroxide. No reaction was found to occur.
The anti-screen clogging characteristics of organic compositions in the form, for example, of fuel oils having incorporated therein the novel metal salts of the present invention were determined from a standard screen clogging test, as described in US. Patent 3,296,130, issued Jan. 3, 1967. In general, this test is conducted using a Sundstrand V3 or S1 home fuel oil burner pump with a self-contained 100-mesh Monel metal screen. About 0.05 percent, by weight, of naturally-formed fuel oil sediment, composed of fuel oil, water, dirt, rust and organic sludge is mixed with 10 liters of the fuel oil. This mixture is circulated by the pump through the screen for 6 hours. Then, the sludge deposit on the screen is washed off with normal pentane and filtered through a tared Gooch crucible. After drying, the material in the Gooch crucible is washed with a 5050 (volume) acetone-methanol mixture. The total organic sediment is obtained by evaporating the pentane and the acetone-methanol filtrates. Drying and weighing the Gooch crucible yields the amount of inorganic sediment. The sum of the organic and inorganic deposits on the screen can be reported in milligrams recovered or converted into percent screen clogging.
The metal salts prepared in accordance with the foregoing Examples 1 through 10 were individually blended in test fuel oils comprising a blend of 60 percent distillate stock obtained from continuous catalytic cracking and 40 percent straight-run distillate stock, having a boiling range of between about 320 F. and about 640 F., and typical of No. 2 fuel oils. Each blend was subjected to the above-described screen clogging test. The test results obtained are set forth in the following Table I.
TABLE I.SC'REEN CLOGGING TEST In order to evaluate the metal salts of the present invention as stabilizers for lubricating oils, and for subsequent incorporation of the latter into grease formulations, these metal salts were subjected to a Catalytic Oxidation Test. This test determines the effectiveness of an additive in preventing the catalytic oxidation of the oil sample under oxidizing conditions. The test procedure is conducted as follows in a 200 mm. X 25 mm. test tube is placed a 25 gram sample of the test oil having immersed therein (a) 15.6 sq. in. of sand-blasted iron wire, (b) 0.78 sq. in. of polished copper wire, (c) 0.87 sq. in. of polished aluminum wire and (d) 0.167 sq. in. of a polished lead specimen. The oil sample is heated to a temperature of 325 F. and maintained at this temperature while dry air is placed therethrough at the rate of 5 liters per hour for a period of 40 hours. The change in neutralization number and kinematic viscosity before and after the oxidation are recorded, and the weight loss of the lead specimen is obtained. In the following Table II are shown the effects of the additives of some of the foregoing examples of the present invention compared with the uninhibited lubricant which comprises a furfural refined neutral mineral oil SUS 130" at 100 F.
TABLE IL-CATALY'IIC OXIDATION TEST Cone, Viscosity Lead weight, increase, loss, Additive percent AN.N percent mg. Sludge Uninliibited oil 19.3 460 220 Medium. Ex.1 4 0.53 60 55 Nil. 4 4.28 83 Nil. 4 3.4 67 82 Ni]. 2 0.5 4.5 4.0 Ni]. 4 1.7 79 71 Nil. 4 2.1 73 52 Nil. 4 9.0 02 54 Ni]. 4 0.9 12 26 Nil. 4 2.7 37 56 Nil. 4 2.7 44 51 Nil. 4 8.1 52 60 Nil.
As is apparent from the data of Tables I and II, the metal salts of the present invention are effective as improving agents in various types of organic compositions,
such as exemplified by their use as anti-screen clogging' agents in fuel oils, or as stabilizers for lubricating oils,
or lubricating oils employed as vehicles in grease formulations. In this respect, it Will also be seen that these additives are effective as improving agents with respect to other specific types of organic compounds, such as fuel oils in the form of gasolines, and more specifically, to the treatment of such hydrocarbons as petroleum distillate fuels. They are also effective as stabilizers for hydrocarbon and synthetic lubricants of various types.
Although the present invention has been described with preferred embodiments, it will be understood that modifications and variations thereof may be resorted to without departing from the spirit and scope of the invention as those skilled in the art will readily appreciate.
I claim:
1. An organic composition, present in major proportion and selected from the group consisting of liquid hydrocarbon fuels and hydrocarbon lubricants, containing, in an amount suflicient to act as an improving agent, a metal salt of the reaction product of an alkyl phenol and at least one member selected from the group consisting of ethylene polyarnines and their hydrocarbon and hydroxy substituted derivatives wherein the metal of said metal salt is selected from the group consisting of calcium, zinc, barium, lithium and potassium and the reactant components of said improving agent are employed in stoichiometric proportions.
2. A composition as defined in claim 1 wherein said metal salt is present in an amount from about .001 percent to about 10 percent, by weight.
3. A composition as defined in claim 1 wherein said metal salt is present in an amount from about .01 percent to about 0.5 percent, by "weight.
4. A composition as defined in claim 1 wherein said composition is a liquid hydrocarbon having a boiling range from about 75 F. to about 1000 F.
5. A composition as defined in claim 1 wherein said composition is a liquid hydrocarbon comprising a petroleum distillate fuel oil having an initial boiling point 8 from about F to about F. and an end boiling point from about 250 F. to about 750 F.
6. A composition as defined in claim 4 wherein said liquid hydrocarbon comprises a gasoline.
7. A composition as defined in claim 4 wherein said liquid hydrocarbon comprises a jet fuel.
8. A composition as defined in claim 4 wherein said liquid hydrocarbon comprises a diesel fuel.
9. A composition as defined in claim 4 wherein said liquid hydrocarbon comprises a turbine oil.
10. A composition as defined in claim 1 wherein said composition comprises a lubricating oil.
11. A composition as defined in claim 1 wherein said composition comprises a grease.
12. A composition as defined in claim 1 wherein said alkyl phenol is selected from the group consisting of didodecylphenol, monododecylphenol, monopolybutylene alkylated phenol and monononylphenol.
13. A composition as defined in claim 1 wherein said ethyleneamine is selected from the group consisting of ethylene diamine, N-hydroxyethylethylene diamine, triethylene tetramine, tetraethylene pentamine, tetrahydroxyethyl ethylene diamine and N-dodecyldiethylene triamine.
References Cited UNITED STATES PATENTS 2,545,113 3/1951 Smith et al. 25242.7 2,971,014 2/1961 Mastin 252-427 X 3,340,190 9/1967 Deluga et al 25242.7 X 3,398,170 8/1968 Cyba 25242.7 X 3,410,670 11/1963 Le Seur 4468 X DANIEL E. WYMAN, Primary Examiner W, CANNON, Assistant Examiner U .S. C]. X.R.
US654327A 1967-07-19 1967-07-19 Organic compositions containing metal salts of reaction product of an alkyl phenol and an ethyleneamine Expired - Lifetime US3493508A (en)

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US4011167A (en) * 1975-07-09 1977-03-08 Mobil Oil Corporation Lubricant compositions containing metal complexes as detergents
US4266945A (en) * 1979-11-23 1981-05-12 The Lubrizol Corporation Molybdenum-containing compositions and lubricants and fuels containing them
US4626283A (en) * 1985-03-21 1986-12-02 Engelhard Corporation Corrosion and marine growth inhibiting compositions
US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
US4774345A (en) * 1985-03-21 1988-09-27 Engelhard Corporation Amine-complexed zinc salts of organic diacids
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes

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US4205960A (en) * 1974-04-09 1980-06-03 The Lubrizol Corporation Hydroxyalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4285824A (en) * 1979-01-22 1981-08-25 The Lubrizol Corporation Hydroxyalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4343740A (en) * 1980-02-22 1982-08-10 The Lubrizol Corporation Hydroxylalkyl hydroxy-aromatic condensation products as fuel and lubricant additives

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US2545113A (en) * 1947-12-08 1951-03-13 Gulf Oil Corp Addition agents for mineral oil lubricants
US2971014A (en) * 1958-09-26 1961-02-07 Lubrizol Corp Oil soluble metal containing compositions and process for making same
US3340190A (en) * 1965-06-01 1967-09-05 Standard Oil Co Railway diesel oil
US3398170A (en) * 1964-05-21 1968-08-20 Universal Oil Prod Co Mixed chelates of a schiff base, an amine, and a transition series metal
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US2545113A (en) * 1947-12-08 1951-03-13 Gulf Oil Corp Addition agents for mineral oil lubricants
US2971014A (en) * 1958-09-26 1961-02-07 Lubrizol Corp Oil soluble metal containing compositions and process for making same
US3410670A (en) * 1964-04-06 1968-11-12 Lubrizol Corp Fuel compositions
US3398170A (en) * 1964-05-21 1968-08-20 Universal Oil Prod Co Mixed chelates of a schiff base, an amine, and a transition series metal
US3340190A (en) * 1965-06-01 1967-09-05 Standard Oil Co Railway diesel oil

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011167A (en) * 1975-07-09 1977-03-08 Mobil Oil Corporation Lubricant compositions containing metal complexes as detergents
US4266945A (en) * 1979-11-23 1981-05-12 The Lubrizol Corporation Molybdenum-containing compositions and lubricants and fuels containing them
US4626283A (en) * 1985-03-21 1986-12-02 Engelhard Corporation Corrosion and marine growth inhibiting compositions
US4774345A (en) * 1985-03-21 1988-09-27 Engelhard Corporation Amine-complexed zinc salts of organic diacids
US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes
US5534039A (en) * 1991-05-13 1996-07-09 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5562742A (en) * 1991-05-13 1996-10-08 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same

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