DE19513391A1 - End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s) - Google Patents
End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s)Info
- Publication number
- DE19513391A1 DE19513391A1 DE19513391A DE19513391A DE19513391A1 DE 19513391 A1 DE19513391 A1 DE 19513391A1 DE 19513391 A DE19513391 A DE 19513391A DE 19513391 A DE19513391 A DE 19513391A DE 19513391 A1 DE19513391 A1 DE 19513391A1
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- trimer
- dimer
- indicates
- alkoxylates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000000539 dimer Substances 0.000 title claims abstract description 27
- 239000013638 trimer Substances 0.000 title claims abstract description 26
- -1 benzyl halides Chemical class 0.000 claims abstract description 8
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 6
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 6
- 239000002168 alkylating agent Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 3
- 235000021317 phosphate Nutrition 0.000 claims abstract description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 238000005187 foaming Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004265 EU approved glazing agent Substances 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
- C11D1/721—End blocked ethers
Abstract
Description
Die vorliegende Erfindung betrifft endgruppenverschlossene Di meralkohol- und Trimeralkoholalkoxylate sowie ein Verfahren zu ihrer Herstellung und ihre Verwendung als schaumarme Tenside.The present invention relates to end group capped di mineral alcohol and trimer alcohol alkoxylates and a process their production and their use as low-foaming surfactants.
Im Hinblick auf die zur Verfügung stehenden oberflächenaktiven Stoffe ist es ausgesprochen schwierig, bei der Auswahl der Substanzen für Wasch- und Reinigungsmittel allen Kriterien, wie Netzeigenschaften, Schaumarmut, Alkalibeständigkeit und biologischer Abbaubarkeit in gleicher Weise gerecht zu werden. Nichtionische Tenside, wie beispielsweise Fettalkohol, Poly glykolether, sind zwar praktisch schaumfrei, die Benetzung insbesondere von festen Oberflächen ist jedoch unzureichend. Auf der anderen Seite zeichnen sich die anionischen Tenside, wie beispielsweise Alkylbenzolsulfonate, zwar häufig durch gute Netzeigenschaften aus, jedoch entwickeln sie zu viel Schaum, insbesondere dann, wenn sie als wäßrige Lösungen durch Düsen verspritzt werden. Hinzukommt, daß die anionischen Ten side ökologisch nicht unbedenklich sind. With regard to the available surface active It is extremely difficult to choose fabrics Substances for detergents and cleaning agents all criteria, such as wetting properties, low foam, alkali resistance and biodegradability in the same way. Nonionic surfactants, such as fatty alcohol, poly glycol ethers are practically foam-free, the wetting however, in particular of solid surfaces is insufficient. On the other hand, the anionic surfactants such as alkylbenzenesulfonates, often by good network properties, but they develop too much Foam, especially when through as aqueous solutions Nozzles are sprayed. In addition, the anionic Ten side are not ecologically harmless.
Aus der DE-A-37 44 525 sind endgruppenverschlossene Fettalko holpolyglykolether, sogenannte "Mischether" bekannt, die durch Veretherung von Fettalkoholpolyglycolethern mit Alkylhalogeni den in Gegenwart von Alkalihydroxiden erhalten werden. Diese Produkte erfüllen zwar die Anforderungen an Schaumarmut, Alka libeständigkeit und biologische Abbaubarkeit, jedoch ist ihr Netzvermögen nicht zufriedenstellend.From DE-A-37 44 525 are end group capped fatty alcohols holpolyglycol ether, so-called "mixed ether" known by Etherification of fatty alcohol polyglycol ethers with alkyl halides which are obtained in the presence of alkali metal hydroxides. These Products meet the requirements for low foam, Alka Resistance and biodegradability, however, is yours Network assets not satisfactory.
Die Aufgabe der vorliegenden Erfindung bestand somit darin, neue schaumarme nichtionische Tenside zu entwickeln, die sich durch gute Netzeigenschaften auszeichnen.The object of the present invention was therefore to to develop new low-foaming nonionic surfactants that characterized by good network properties.
Gegenstand der vorliegenden Erfindung sind endgruppenver schlossene Dimeralkohol- und Trimeralkoholalkoxylate, die da durch erhältlich sind, daß man Dimeralkohol- und Trimeralko holalkoxylate in an sich bekannter Weise mit einem Alky lierungsmittel ausgewählt aus der Gruppe, die von Alkylhaloge niden, Benzylhalogeniden, Dialkylsulfaten und Dialkylphospha ten gebildet wird, umsetzt.The present invention relates to end groups included dimer alcohol and trimer alcohol alkoxylates are available through that one Dimeralkohol- and Trimeralko holalkoxylates in a manner known per se with an alky selected from the group that of alkyl halogens nidene, benzyl halides, dialkyl sulfates and dialkylphospha ten is implemented.
Überraschenderweise wurde festgestellt, daß die erfindungsge mäßen endgruppenverschlossenen Dimeralkohol- und Trimeralko holalkoxylate über ausgezeichnete Netz- und Reinigungseigen schaften verfügen, gut wasserlöslich, schaumarm, alkalibestän dig und leicht biologisch abbaubar sind.Surprisingly, it was found that the fiction end-capped dimeral alcohol and trimeralko holalkoxylate through excellent wetting and cleaning properties have good water-soluble, low-foaming, alkali-resistant dig and easily biodegradable.
Ein weiterer Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von endgruppenverschlossenen Dimer alkohol- und Trimeralkoholalkoxylaten, dadurch gekennzeichnet, daß man Dimeralkohol- und Trimeralkoholalkoxylate in an sich bekannter Weise mit einem Alkylierungsmittel ausgewählt aus der Gruppe, die von Alkylhalogeniden, Benzylhalogeniden, Dialkyl sulfaten und Dialkylphosphaten gebildet wird, umsetzt.Another object of the present invention is a Process for the preparation of end group capped dimers alcohol and trimer alcohol alkoxylates, characterized in that that you have dimer alcohol and trimer alcohol alkoxylates in themselves known manner with an alkylating agent selected from the Group consisting of alkyl halides, benzyl halides, dialkyl sulfates and dialkyl phosphates is formed.
Dimer- und Trimeralkohole sind im Handel erhältliche Verbin dungen und können beispielsweise durch Reduktion von Dimer- und Trimerfettsäureestern gewonnen werden. Die Dimer- und Tri merfettsäuren selbst können z. B. durch Oligomerisierung von ungesättigten Fettsäuren erhalten werden. Die Dimer- und Tri merfettsäuren sind in der Regel Gemische aus acyclischen und cyclischen Dicarbonsäuren mit durchschnittlich 36 bis 44 Koh lenstoffatomen [vgl. A. Hinze in Fette & Öle, 26 (1994)].Dimer and trimer alcohols are commercially available verbs and can be reduced, for example, by reducing dimer and trimer fatty acid esters. The dimer and tri Mer fatty acids themselves can e.g. B. by oligomerization of unsaturated fatty acids can be obtained. The dimer and tri Mer fatty acids are usually mixtures of acyclic and cyclic dicarboxylic acids with an average of 36 to 44 Koh lenstoffatomen [cf. A. Hinze in Fette & Öle, 26 (1994)].
Aus den Dimer- und Trimeralkoholen können die Dimer- und Tri meralkoholalkoxylate in an sich bekannter Weise durch Alkoxy lierung der Dimer- und Trimeralkohole erhalten werden. Die Alkoxylate können 1 bis 30 Alkoxygruppen pro OH-Gruppe ent halten. Zu den bevorzugt eingesetzten Alkoxylaten gehören bei spielsweise die Ethoxylate und die Propoxylate oder Addukte die sowohl Ethoxy- als auch Propoxygruppen im Molekül enthal ten. Besonders bevorzugt werden Addukte mit durchschnittlich 1 bis 20 Mol Ethylenoxid pro OH-Gruppe eingesetzt, die gegebe nenfalls auch durchschnittlich 1 bis 5 Mol Propylenoxid pro Mol Alkohol enthalten können. Die angegebenen Alkoxylierungs grade stellen statistische Mittelwerte dar, die für ein spe zielles Produkt eine ganze oder eine gebrochene Zahl sein kön nen.From the dimer and trimer alcohols, the dimer and tri mineral alcohol alkoxylates in a manner known per se by alkoxy tion of the dimer and trimer alcohols can be obtained. The Alkoxylates can contain 1 to 30 alkoxy groups per OH group hold. The preferred alkoxylates include for example the ethoxylates and the propoxylates or adducts which contain both ethoxy and propoxy groups in the molecule Adducts with an average of 1 used up to 20 moles of ethylene oxide per OH group also an average of 1 to 5 moles of propylene oxide per May contain moles of alcohol. The specified alkoxylation just represent statistical averages that are necessary for a specific target product can be an integer or a fractional number nen.
Typische Beispiele für Alkylierungsmittel, die im Sinne der Erfindung Verwendung finden können, sind Methylchlorid, Dime thylsulfat, Diethylsulfat, Diethylphosphat, Benzylchlorid und vorzugsweise Butylchlorid.Typical examples of alkylating agents which are used in the sense of Invention can be used are methyl chloride, dime ethyl sulfate, diethyl sulfate, diethyl phosphate, benzyl chloride and preferably butyl chloride.
Die Herstellung der erfindungsgemäßen endgruppenverschlossenen Dimeralkohol- und Trimeralkoholalkoxylate kann in an sich be kannter Weise durch Umsetzung der Dimeralkohol- und Trimeral koholalkoxylate mit dem Alkylierungsmittel erfolgen. Die Alky lierungsmittel können in einer Menge von 0,8 bis 2 Mol pro freier OH-Gruppe eingesetzt werden. Die Umsetzung erfolgt be vorzugt in Gegenwart einer starken Base, insbesondere Alkali hydroxiden, wie z. B. NaOH und KOH, eingesetzt. Die Base und das Alkylhalogenid können in einem molaren Verhältnis von 0,5 bis 2 eingesetzt werden, wobei äquimolare Menge besonders be vorzugt sind. Die Base kann in Form ihrer konzentrierten wäß rigen Lösungen zugefügt werden oder, wie es in der deutschen Patentschrift DE-PS 37 44 525 beschrieben ist, in fester Form zugegeben werden. Die Reaktionstemperatur liegt üblicherweise zwischen 60 und 140°C.The production of the end group capped according to the invention Dimer alcohol and trimer alcohol alkoxylates can be in itself known way by implementing the dimer alcohol and trimeral alcohol alkoxylates with the alkylating agent. The alky Glazing agents can be used in an amount of 0.8 to 2 moles per free OH group can be used. The implementation takes place preferably in the presence of a strong base, especially alkali hydroxides, such as. B. NaOH and KOH used. The base and the alkyl halide can be used in a molar ratio of 0.5 to 2 are used, equimolar amount being particularly are preferred. The base can in the form of its concentrated aq solutions or, as is the case in German Patent specification DE-PS 37 44 525 is described in solid form be added. The reaction temperature is usually between 60 and 140 ° C.
Die Aufarbeitung des Reaktionsproduktes erfolgt in an sich be kannter Weise. Zum Abtrennen des gebildeten Alkalimetallhalo genids oder -sulfats kann das Rohprodukt mit Wasser versetzt werden. Das Produkt befindet sich dann in der organischen Phase, während das Halogenid oder Sulfat im Wasser gelöst vorliegt. Noch vorhandene Ausgangsmaterialien wie Al kylierungsmittel und Wasser können durch Destillation des Rohproduktes entfernt werden. The reaction product is worked up in itself known way. For separating the alkali metal halo formed genids or sulfates can be added to the raw product with water will. The product is then in the organic Phase while the halide or sulfate is dissolved in the water is present. Existing raw materials such as Al Kylierungsmittel and water can by distillation of the Raw product are removed.
Die erfindungsgemäßen endgruppenverschlossenen Dimeralkohol- und Trimeralkoholalkoxylate sind gut wasserlöslich, schaumarm, alkalibeständig, leicht biologisch abbaubar und verfügen über ein ausgezeichnetes Netz- und Reinigungsvermögen. Ein weiterer Gegenstand der Erfindung betrifft daher die Verwendung der er findungsgemäßen Verbindungen als schaumarme Tenside, die ins besondere in Allzweckreinigern, Geschirrspülmitteln und in gewerblichen Reinigungsmitteln, die zur Spritz- oder Sprühreinigung eingesetzt werden, verwendet werden können, sowie zur Herstellung von oberflächenaktiven Mitteln, die die erfindungsgemäßen Verbindungen in Mengen von 1-100, vorzugsweise 15-95 Gew.-%. - bezogen auf die Mittel, enthalten können.The end group capped dimer alcohol and Trimer alcohol alkoxylates are readily water-soluble, low-foaming, alkali-resistant, easily biodegradable and have excellent wetting and cleaning properties. Another The invention therefore relates to the use of the Compounds according to the invention as low-foam surfactants, which ins especially in all - purpose cleaners, dishwashing detergents and in commercial cleaning agents for spraying or Spray cleaning can be used can be used as well as for the production of surfactants that the compounds according to the invention in amounts of 1-100, preferably 15-95% by weight. - Based on the funds included can.
Die folgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn darauf einzuschränken.The following examples are intended to be the subject of the invention explain in more detail without restricting it.
520 g (0,38 Mol) C₃₆-Dimeralkohol mit 10 Ethylenoxideinheiten
(MG = 1368,5) und 100,3 g 85%ige KOH (1,52 Mol) wurden unter
Stickstoff im Reaktionsgefäß vorgelegt und auf 100°C erhitzt.
140,7 g Butylchlorid (1,52 Mol) wurden innerhalb von 15 Min.
zugetropft. Anschließend wurde das Reaktionsgemisch bis zum
schwachen Rückfluß erhitzt und 8 Stunden bei dieser Temperatur
gehalten. Zur Aufarbeitung des Rohproduktes wurden etwa 450 ml
Wasser zugesetzt, der pH-Wert wurde mit Salzsäure auf ca. 7
eingestellt. Die Phasentrennung dieses Gemisches erfolgte in
einem Heißdampfschütteltrichter bei etwa 70 bis 80°C. Die
Produktphase wurde anschließend noch zweimal mit je 500 ml bei
dieser Temperatur gewaschen. Die organische Phase wurde dann
im Wasserstrahlvakuum destilliert, um überschüssiges BuCl und
Wasser zu entfernen. Beim Abkühlen ausgefallenes Salz wurde
abfiltriert. Man erhielt eine hellgelbe viskose Flüssigkeit
mit einer OH-Zahl von 4,4.
Ausbeute: 524 g (93% d. Th.)520 g (0.38 mol) of C₃₆ dimer alcohol with 10 ethylene oxide units (MW = 1368.5) and 100.3 g of 85% KOH (1.52 mol) were placed under nitrogen in the reaction vessel and heated to 100 ° C. 140.7 g of butyl chloride (1.52 mol) were added dropwise within 15 minutes. The reaction mixture was then heated to a gentle reflux and held at this temperature for 8 hours. About 450 ml of water were added to work up the crude product, and the pH was adjusted to about 7 using hydrochloric acid. The phase separation of this mixture was carried out in a superheated steam shaker at about 70 to 80 ° C. The product phase was then washed twice with 500 ml each at this temperature. The organic phase was then distilled in a water jet vacuum to remove excess BuCl and water. Salt which precipitated on cooling was filtered off. A light yellow viscous liquid with an OH number of 4.4 was obtained.
Yield: 524 g (93% of theory)
Wie im Beispiel 1 wurden 520 g (0,256 Mol) C₅₄-Trimertriol mit
10 Ethylenoxideinheiten (MG = 2028) mit 101,65 g 85%iger KOH
(1,54 Mol) und 142,6 g BuCl (1,54 Mol) umgesetzt und aufgear
beitet. Es wurde ein hellgelbes Produkt mit einer restlichen
OH-Zahl von 3,4 erhalten.
Ausbeute: 526,0 g (93% d. Th.)As in Example 1, 520 g (0.256 mol) of C₅₄-trimer triol with 10 ethylene oxide units (MW = 2028) were reacted with 101.65 g of 85% KOH (1.54 mol) and 142.6 g BuCl (1.54 mol) and processed. A light yellow product with a residual OH number of 3.4 was obtained.
Yield: 526.0 g (93% of theory)
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19513391A DE19513391A1 (en) | 1995-04-08 | 1995-04-08 | End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19513391A DE19513391A1 (en) | 1995-04-08 | 1995-04-08 | End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19513391A1 true DE19513391A1 (en) | 1996-10-10 |
Family
ID=7759267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19513391A Withdrawn DE19513391A1 (en) | 1995-04-08 | 1995-04-08 | End gp.-capped dimer alcohol- and trimer alcohol alkoxylate(s) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19513391A1 (en) |
Cited By (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6380147B1 (en) | 1998-06-03 | 2002-04-30 | Henkel Kommanditgesellschaft Auf Aktien | Detergents containing amylase and protease |
| US6391838B1 (en) | 1999-03-31 | 2002-05-21 | Henkel Kommanditgesellschaft Auf Aktien | Detergents containing enzymes and bleach activators |
| EP1254947A1 (en) * | 2001-05-04 | 2002-11-06 | Cognis Deutschland GmbH & Co. KG | Gemini surfactants |
| EP1254949A1 (en) * | 2001-05-04 | 2002-11-06 | Cognis Deutschland GmbH & Co. KG | Gemini surfactants for rinse aids |
| EP1254948A1 (en) * | 2001-05-04 | 2002-11-06 | Cognis Deutschland GmbH & Co. KG | Gemini surfactants |
| US6528474B1 (en) | 1999-08-04 | 2003-03-04 | Henkel Kommanditgesellschaft Auf Aktien | Method of manufacturing a detergent with soluble builder |
| DE102007016391A1 (en) | 2007-04-03 | 2008-10-09 | Henkel Ag & Co. Kgaa | Detergent or cleaning agent for preventing transfer of textile color of colored textiles from uncolored or different colored textiles in laundry, particularly in tenside containing aqueous solution, has color transfer inhibitor |
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-
1995
- 1995-04-08 DE DE19513391A patent/DE19513391A1/en not_active Withdrawn
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