EP0295385A1 - Process for preparing fatty acid diesters of a trialcanolamine and their use - Google Patents

Process for preparing fatty acid diesters of a trialcanolamine and their use Download PDF

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Publication number
EP0295385A1
EP0295385A1 EP88106112A EP88106112A EP0295385A1 EP 0295385 A1 EP0295385 A1 EP 0295385A1 EP 88106112 A EP88106112 A EP 88106112A EP 88106112 A EP88106112 A EP 88106112A EP 0295385 A1 EP0295385 A1 EP 0295385A1
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Prior art keywords
fatty acid
trialkanolamine
acid esters
esters
acid
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German (de)
French (fr)
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EP0295385B1 (en
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Wulf Dr. Ruback
Jan Dr. Schut
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Huels AG
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Huels AG
Chemische Werke Huels AG
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    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • esterification catalysts i.a. Alkali hydroxides, mineral acids, Lewis acids etc. are used.
  • the quaternized trialkanolamine difatty acid esters are used as fabric softener components.
  • the main component due to the thermodynamic equilibrium is also portions of the corresponding mono- and triesters.
  • This thermodynamic mixture is hereinafter to be understood as trialkanolamine difatty acid ester.
  • esterification of the trialkanolamines is carried out with about two equivalents of fatty acid in the presence of the known esterification catalysts mentioned above, then after the customary quaternization, e.g. B. with dimethyl sulfate, quaternary ammonium compounds obtained, such as. B. N-methyl-triethanolammonium ditallow fatty acid methyl sulfate, properties which are undesirable in a raw material for fabric softeners.
  • the products adjusted to a content of 85 to 90 percent by weight with water and lower alcohols, such as isopropyl alcohol, are not flowable, that is, they are too solid, and they also tend to form strong crystals.
  • the 85% by weight end product consists of a relatively thin melt with crystallites in it. These settle out within a very short time when left standing. This affects the processability and even quality fluctuations can occur in the fabric softening agents made from it.
  • the task thus arises to find a method of producing trialkanolamine difatty acid esters which can be operated at comparatively low cost and leads to products which are flowable in a highly concentrated setting (85 to 90 percent by weight) and do not tend to settle.
  • the fatty acids of the fatty acid esters expediently contain 4 to 24, preferably 8 to 22, in particular 10 to 20, carbon atoms.
  • the alcohols of the fatty acid esters advantageously contain 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms.
  • the alcohols of the fatty acid esters should be 1 to 6 alcohols, preferably 1 to 3 alcohols.
  • trialkanolamine fatty acid diesters produced according to the process of the invention are - after the usual quaternization with z.
  • Suitable trialkanolamines which are to be implemented according to the invention are those which have the formula suffice in which R, R1 and R2 can be different and are hydrogen or alkyl radicals having 1 to 6, preferably 1 to 4, in particular having one carbon atom (s). R, R1 and R2 are particularly preferably hydrogen.
  • trialkanolamines are triethanolamine, triisopropanolamine, triisobutanolamine, triisopentanolamine, triisohexanolamine, diethanol-monoisopropanolamine, monoethanol-diisopropanolamine, monoethanol-diisobutanolamine and analogues.
  • the fatty acids which are reacted with the trialkanolamines are expediently those having 8 to 24, preferably 12 to 22, in particular having 16 to 20, carbon atoms in the linear or branched alkyl chain or the alkene chain.
  • carpyl acid For example, carpyl acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid and their branched or unsaturated homologs, such as. B. oleic acid.
  • the fatty acid esters present in the reaction of the fatty acids with the trialkanolamines are to be used in amounts of 0.05 to 5.0 percent by weight, preferably 0.1 to 2.0 percent by weight, in particular 0.2 to 1.0 percent by weight, based on the total mixture .
  • fatty acid esters are derived, for. B. from fatty acids with 4 to 24 carbon atoms, preferably 8 to 22, in particular 10 to 20 carbon atoms.
  • B. there are z. B. in question: butyric acid, valeric acid, capronic, caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic and lignoceric acid and their branched isomers, such as. B. isovaleric acid, or its unsaturated isomers, such as. B. oleic acid.
  • Suitable alcohols from which the fatty acid esters can be derived, have 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms. They can be 1- to 6-valent, preferably 1- to 3-valent.
  • Examples include: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, isohexanol, heptanol, octanol, 2-ethylhexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, butylene glycol 1,2, 1,4-butanediol, pentanediols, hexanediols, heptanediols, octanediols, glycerol, butanetriol, pentanetriols, hexanetriols, octanetriols, erythritol, pentaerythritol, pentites, hexites, such as sorbitol, mannitol, dulci
  • fatty acid esters for example: the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl esters of the above.
  • Fatty acids with 4 to 24 carbon atoms preferably the esters of the naturally occurring fatty acid mixtures, such as tallow fatty acid methyl ester, ethyl ester, coconut fatty acid methyl ester, ethyl ester, palm oil fatty acid methyl ester, ethyl ester, with particular preference the naturally occurring glycerol esters of fatty acids or fatty acid mixtures, such as.
  • partial esters of polyhydric alcohols is also possible.
  • fatty acid esters used in the esterification reaction have the same C number in the acyl part as the fatty acids intended for the esterification.
  • the pressure and temperature conditions are the same as those used when using known esterification catalysts, namely e.g. B. 30 to 300 ° C, preferably 170 to 220 ° C and 3 to 3,000, preferably 700 to 1 100 mbar. Higher temperatures and pressures are also possible, but generally not necessary.
  • the mixture is then cooled to 90 ° C. and quaternized with 124.7 g (0.99 mol) of dimethyl sulfate within 30 minutes.
  • the product is then adjusted to a solids content of 85% with 140.6 g of isopropyl alcohol and bleached with 20 g (2.5%) of 30% hydrogen peroxide solution.
  • the product is just as flowable as that produced according to Example 1.
  • Example 1 The procedure is as described in Example 1. Instead of the tallow fatty acid methyl ester, 5 g of oleic acid ethyl ester are used. A product is obtained which is comparable in its properties to that prepared according to Example 1.

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Abstract

A process for the preparation of trialkanolamine di(fatty acid) esters in which a trialkanolamine is reacted with a fatty acid in the presence of small amounts of a fatty acid ester. The trialkanolamine fatty acid diesters obtained can be converted into the quaternary ammonium salt by means of standard quaternizing agents, and the resulting products can be employed as fabric conditioners.

Description

Die Herstellung von Fettsäurestern, wie auch Trialkanolaminfettsäure­estern, ist wohlbekannt. Als Veresterungskatalysatoren werden i.a. Alkalihydroxide, Mineralsäuren, Lewissäuren etc. eingesetzt.The production of fatty acid esters, as well as trialkanolamine fatty acid esters, is well known. As esterification catalysts i.a. Alkali hydroxides, mineral acids, Lewis acids etc. are used.

Als Wäscheweichspülkomponenten werden die quaternierten Trialkanol­amindifettsäureester eingesetzt. Bei der Reaktion von ca. zwei Äqui­valenten Fettsäure mit Trialkanolamin erhält man neben diesem Trial­kanolamindifettsäureester als Hauptkomponente aufgrund des thermody­namischen Gleichgewichtes auch Anteile der entsprechenden Mono- und Triester. Dieses thermodynamische Gemisch ist im weiteren unter der Bezeichnung Trialkanolamindifettsäureester zu verstehen.The quaternized trialkanolamine difatty acid esters are used as fabric softener components. In the reaction of approximately two equivalents of fatty acid with trialkanolamine, in addition to this trialkanolamine difatty acid ester, the main component due to the thermodynamic equilibrium is also portions of the corresponding mono- and triesters. This thermodynamic mixture is hereinafter to be understood as trialkanolamine difatty acid ester.

Führt man die Veresterung der Trialkanolamine mit ca. zwei Äquiva­lenten Fettsäure in Gegenwart der oben genannten bekannten Veresterungskatalysatoren durch, so zeigen die nach der üblichen Quarternisierung, z. B. mit Dimethylsulfat, erhaltenen quarternären Ammoniumverbindungen, wie z. B. N-Methyl-triethanolammonium-di­talgfettsäureester-methylsulfat, Eigenschaften, die bei einem Rohstoff für Wäscheweichspülmittel unerwünscht sind. Die mit Wasser und niederen Alkoholen, wie Isopropylalkohol, auf einen Gehalt von 85 bis 90 Gewichtsprozent eingestellten Produkte sind nicht fließfähig, also zu fest, und außerdem neigen sie zu starker Kristallbildung.If the esterification of the trialkanolamines is carried out with about two equivalents of fatty acid in the presence of the known esterification catalysts mentioned above, then after the customary quaternization, e.g. B. with dimethyl sulfate, quaternary ammonium compounds obtained, such as. B. N-methyl-triethanolammonium ditallow fatty acid methyl sulfate, properties which are undesirable in a raw material for fabric softeners. The products adjusted to a content of 85 to 90 percent by weight with water and lower alcohols, such as isopropyl alcohol, are not flowable, that is, they are too solid, and they also tend to form strong crystals.

In der US-A-3 915 867 wird die Herstellung von Triethanolaminfettsäu­rediestern durch Umsetzung von Triethanolamin mit Fettsäuremethyl­estern beschrieben. Die daraus durch Quarternisierung hergestellten quarternären Ammoniumverbindungen zeigen zwar nach der üblichen Ein­stellung mit Wasser und Isopropanol auf 85 bis 90 Gewichtsprozent die gewünschte fließfähige Beschaffenheit, jedoch ergeben sich in diesem Falle andere Probleme.US Pat. No. 3,915,867 describes the preparation of triethanolamine fatty acid diesters by reacting triethanolamine with fatty acid methyl esters. The quaternary ammonium compounds produced therefrom by quaternization show the desired flowability after the usual adjustment with water and isopropanol to 85 to 90 percent by weight, but in this case there are other problems.

Das 85gewichtsprozentige Endprodukt besteht aus einer relativ dünnen Schmelze, in der sich Kristallite befinden. Diese setzen sich beim Stehenlassen innerhalb recht kurzer Zeit ab. Dadurch wird die Verar­beitbarkeit beeinträchtigt, und es können sogar Qualitätsschwankungen bei den daraus hergestellten Wäscheweichspülmitteln auftreten.The 85% by weight end product consists of a relatively thin melt with crystallites in it. These settle out within a very short time when left standing. This affects the processability and even quality fluctuations can occur in the fabric softening agents made from it.

Außerdem ist zu bedenken, daß die als Reaktanten eingesetzten Methyl­ester gegenüber den unveresterten Fettsäuren eine veredelte Verarbei­tungsstufe darstellen und daß deren Einsatz somit erheblich kostenauf­wendiger ist.It should also be borne in mind that the methyl esters used as reactants represent a refined processing stage compared to the unesterified fatty acids and that their use is therefore considerably more expensive.

Es ergibt sich somit die Aufgabenstellung, eine Methode der Herstel­lung von Trialkanolamindifettsäureestern zu finden, welche mit ver­gleichsweise geringem Kostenaufwand betrieben werden kann und zu Pro­dukten führt, die in hochkonzentrierter Einstellung (85 bis 90 Ge­wichtsprozent) fließfähig sind und nicht zum Absetzen neigen.The task thus arises to find a method of producing trialkanolamine difatty acid esters which can be operated at comparatively low cost and leads to products which are flowable in a highly concentrated setting (85 to 90 percent by weight) and do not tend to settle.

Diese Aufgaben wurden gelöst durch ein Verfahren zur Herstellung von Trialkanolamindifettsäureestern durch Umsetzen von Trialkanolamin mit 1,5 bis 2,5, bevorzugt 1,8 bis 2,2, insbesondere 1,9 bis 2,1 Äquivalenten Fettsäure, das dadurch gekennzeichnet ist, daß man die Umsetzung in Gegenwart von 0,05 bis 5,0, vorzugsweise 0,1 bis 2,0, insbesondere von 0,2 bis 1,0 Gewichtsprozent, bezogen auf die Gesamtmischung, eines Fettsäureesters vornimmt.These objects were achieved by a process for the preparation of trialkanolamine difatty acid esters by reacting trialkanolamine with 1.5 to 2.5, preferably 1.8 to 2.2, in particular 1.9 to 2.1 equivalents of fatty acid, which is characterized in that the reaction is carried out in the presence of 0.05 to 5.0, preferably 0.1 to 2.0, in particular 0.2 to 1.0 percent by weight, based on the mixture as a whole, of a fatty acid ester.

Zweckmäßigerweise enthalten die Fettsäuren der Fettsäureester 4 bis 24, vorzugsweise 8 bis 22, insbesondere 10 bis 20 Kohlenstoffatome.The fatty acids of the fatty acid esters expediently contain 4 to 24, preferably 8 to 22, in particular 10 to 20, carbon atoms.

Die Alkohole der Fettsäureester enthalten zweckmäßigerweise 1 bis 8, vorzugsweise 1 bis 6, insbesondere 1 bis 3 Kohlenstoffatome.The alcohols of the fatty acid esters advantageously contain 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms.

Die Alkohole der Fettsäureester sollten 1- bis 6wertige Alkohole, vor­zugsweise 1- bis 3wertige Alkohole, sein.The alcohols of the fatty acid esters should be 1 to 6 alcohols, preferably 1 to 3 alcohols.

Die gemäß dem Verfahren der Erfindung hergestellten Trialkanolamin­fettsäurediester sind - nach der üblichen Quarternisierung mit z. B. Dimethylsulfat - als Wäscheweichspülmittel zu verwenden.The trialkanolamine fatty acid diesters produced according to the process of the invention are - after the usual quaternization with z. B. Dimethyl sulfate - to use as fabric softener.

Als Trialkanolamine, welche erfindungsgemäß umzusetzen sind, kommen zweckmäßigerweise solche infrage, die der Formel

Figure imgb0001
genügen, in der R, R¹ und R² verschieden sein können und Wasserstoff oder Alkylreste mit 1 bis 6, vorzugsweise 1 bis 4, insbesondere mit einem Kohlenstoffatom(en) bedeuten. In besonders bevorzugter Weise be­deuten R, R¹ und R² Wasserstoff.Suitable trialkanolamines which are to be implemented according to the invention are those which have the formula
Figure imgb0001
 suffice in which R, R¹ and R² can be different and are hydrogen or alkyl radicals having 1 to 6, preferably 1 to 4, in particular having one carbon atom (s). R, R¹ and R² are particularly preferably hydrogen.

Beispiele für Trialkanolamine sind Triethanolamin, Triisopropanolamin, Triisobutanolamin, Triisopentanolamin, Triisohexanolamin, Diethanol-­monoisopropanolamin, Monoethanol-diisopropanolamin, Monoethanol-diiso­butanolamin und Analoge.Examples of trialkanolamines are triethanolamine, triisopropanolamine, triisobutanolamine, triisopentanolamine, triisohexanolamine, diethanol-monoisopropanolamine, monoethanol-diisopropanolamine, monoethanol-diisobutanolamine and analogues.

Die Fettsäuren, welche mit den Trialkanolaminen zur Umsetzung kommen, sind zweckmäßigerweise solche mit 8 bis 24, vorzugsweise 12 bis 22, insbesondere mit 16 bis 20 Kohlenstoffatomen in der linearen oder verzweigten Alkylkette oder der Alkenkette.The fatty acids which are reacted with the trialkanolamines are expediently those having 8 to 24, preferably 12 to 22, in particular having 16 to 20, carbon atoms in the linear or branched alkyl chain or the alkene chain.

Es kommen beispielsweise infrage: Carpylsäure, Caprinsäure, Laurinsäu­re, Myristinsäure, Palmitinsäure, Stearinsäure, Arachinsäure, Behen­säure sowie deren verzweigte oder deren ungesättigte Homologe, wie z. B. Ölsäure.For example, carpyl acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid and their branched or unsaturated homologs, such as. B. oleic acid.

Die bei der Umsetzung der Fettsäuren mit den Trialkanolaminen anwesen­den Fettsäureester sind in Mengen von 0,05 bis 5,0 Gewichtsprozent, vorzugsweise 0,1 bis 2,0 Gewichtsprozent, insbesondere 0,2 bis 1,0 Ge­wichtsprozent, bezogen auf die Gesamtmischung, einzusetzen.The fatty acid esters present in the reaction of the fatty acids with the trialkanolamines are to be used in amounts of 0.05 to 5.0 percent by weight, preferably 0.1 to 2.0 percent by weight, in particular 0.2 to 1.0 percent by weight, based on the total mixture .

Diese Fettsäureester leiten sich z. B. von Fettsäuren mit 4 bis 24 Kohlenstoffatomen, vorzugsweise 8 bis 22, insbesondere 10 bis 20 Kohlenstoffatomen ab.These fatty acid esters are derived, for. B. from fatty acids with 4 to 24 carbon atoms, preferably 8 to 22, in particular 10 to 20 carbon atoms.

Es kommen z. B. infrage: Buttersäure, Valeriansäure, Capron-, Capryl-, Caprin-, Laurin-, Myristin-, Palmitin-, Stearin-, Arachin-, Behen- und Lignocerinsäure sowie deren verzweigte Isomere, wie z. B. Isovalerian­säure, oder deren ungesättigte Isomere, wie z. B. Ölsäure.There are z. B. in question: butyric acid, valeric acid, capronic, caprylic, capric, lauric, myristic, palmitic, stearic, arachic, behenic and lignoceric acid and their branched isomers, such as. B. isovaleric acid, or its unsaturated isomers, such as. B. oleic acid.

Geeignete Alkohole, von denen sich die Fettsäureester ableiten können, haben 1 bis 8, vorzugsweise 1 bis 6, insbesondere 1 bis 3 Kohlenstoff­atome. Sie können 1- bis 6wertig, vorzugsweise 1- bis 3wertig, sein.Suitable alcohols, from which the fatty acid esters can be derived, have 1 to 8, preferably 1 to 6, in particular 1 to 3 carbon atoms. They can be 1- to 6-valent, preferably 1- to 3-valent.

Es lassen sich beispielsweise nennen: Methanol, Ethanol, Propanol, Isopropanol, Butanol, Isobutanol, Pentanol, Isopentanol, Hexanol, Iso­hexanol, Heptanol, Octanol, 2-Ethylhexanol, Ethylenglykol, Propandiol-­1,2, Propandiol-1,3, Butylenglykol-1,2, Butandiol-1,4, Pentandiole, Hexandiole, Heptandiole, Octandiole, Glycerin, Butantriol, Pentantri­ole, Hexantriole, Octantriole, Erythrit, Pentaerythrit, Pentite, Hexi­te, wie Sorbit, Mannit, Dulcit, vorzugsweise Methanol, Ethanol und Glycerin.Examples include: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, isohexanol, heptanol, octanol, 2-ethylhexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, butylene glycol 1,2, 1,4-butanediol, pentanediols, hexanediols, heptanediols, octanediols, glycerol, butanetriol, pentanetriols, hexanetriols, octanetriols, erythritol, pentaerythritol, pentites, hexites, such as sorbitol, mannitol, dulcitol, preferably methanol, ethanol and glycerol.

Als Fettsäureester lassen sich somit beispielsweise einsetzen: die Me­thyl-, Ethyl-, Propyl-, Isopropyl-, Butyl-, Pentyl-, Hexylester der o. a. Fettsäuren mit 4 bis 24 C-Atomen, mit Vorzug die Ester der na­türlich vorkommenden Fettsäuregemische, wie Talgfettsäuremethylester, -ethylester, Kokosfettsäuremethylester, -ethylester, Palmölfettsäu­remethylester, -ethylester, mit besonderem Vorzug die natürlich vor­kommenden Glycerinester der Fettsäuren bzw. Fettsäuregemische, wie z. B. Tripalmitin, Tristearin, Talgfett, Kokosfett, Palmölfett. Auch der Einsatz von Teilestern mehrwertiger Alkohole ist möglich, also z. B. Glycerinmonostearat, Glycerindistearat, Sorbitmonolaurat, Sor­bitdistearat, etc.The following can thus be used as fatty acid esters, for example: the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl esters of the above. Fatty acids with 4 to 24 carbon atoms, preferably the esters of the naturally occurring fatty acid mixtures, such as tallow fatty acid methyl ester, ethyl ester, coconut fatty acid methyl ester, ethyl ester, palm oil fatty acid methyl ester, ethyl ester, with particular preference the naturally occurring glycerol esters of fatty acids or fatty acid mixtures, such as. B. tripalmitin, tristearin, tallow fat, coconut fat, palm oil fat. The use of partial esters of polyhydric alcohols is also possible. B. glycerol monostearate, glycerol distearate, sorbitol monolaurate, sorbitol distearate, etc.

Es ist nicht notwendig, daß die bei der Veresterungsreaktion einge­setzten Fettsäureester im Acylteil dieselbe C-Zahl aufweisen wie die für die Veresterung bestimmten Fettsäuren.It is not necessary that the fatty acid esters used in the esterification reaction have the same C number in the acyl part as the fatty acids intended for the esterification.

Die Druck- und Temperaturbedingungen sind die gleichen, wie sie auch bei Einsatz bekannter Veresterungskatalysatoren angewendet werden, nämlich z. B. 30 bis 300 °C, vorzugsweise 170 bis 220 °C und 3 bis 3 000, vorzugsweise 700 bis 1 100 mbar. Es sind auch höhere Tempera­turen und Drücke möglich, aber i. a. nicht notwendig.The pressure and temperature conditions are the same as those used when using known esterification catalysts, namely e.g. B. 30 to 300 ° C, preferably 170 to 220 ° C and 3 to 3,000, preferably 700 to 1 100 mbar. Higher temperatures and pressures are also possible, but generally not necessary.

Die nun folgenden Beispiele dienen der weiteren Erläuterung der Erfin­dung.The following examples serve to further explain the invention.

Beispiel 1example 1

552 g (2 Mol) Talgfettsäure (z. B. EDENOR(R) Ti der Fa. Henkel) werden aufgeschmolzen vorgelegt, auf 90 °C erwärmt und mit 4 g (= 0,56 % des gesamten Veresterungsgemisches) Talgfettsäuremethylester (z. B. EDENOR ME/Ti der Fa. Henkel) versetzt. Nachdem 15 Minuten gerührt wurde, werden 156 g (1,05 Mol) Triethanolamin hinzugegeben, das Reaktionsgemisch anschließend auf 195 °C erwärmt und bei dieser Temperatur weitergerührt, bis eine Säurezahl von ≦ 1mg KOH/G erreicht ist. Dies ist nach ca. 3 Stunden der Fall, wobei 36 g Wasser abdestillieren.552 g (2 mol) of tallow fatty acid ( e.g. EDENOR (R) Ti from Henkel) are melted, heated to 90 ° C. and mixed with 4 g (= 0.56% of the total esterification mixture) of tallow fatty acid methyl ester (e.g. EDENOR ME / Ti from Henkel). After stirring for 15 minutes, 156 g (1.05 mol) of triethanolamine are added, the reaction mixture is then heated to 195 ° C. and stirring is continued at this temperature until an acid number of ≦ 1 mg KOH / G is reached. This is the case after about 3 hours, with 36 g of water distilling off.

Anschließend wird auf 90 °C abgekühlt und mit 124,7 g (0,99 Mol) Dime­thylsulfat innerhalb 30 Minuten quarterniert. Danach wird das Produkt mit 140,6 g Isopropylalkohol auf einen Feststoffgehalt von 85 % einge­stellt und mit 20 g (2,5 %) 30 %iger Wasserstoffperoxidlösung ge­bleicht.The mixture is then cooled to 90 ° C. and quaternized with 124.7 g (0.99 mol) of dimethyl sulfate within 30 minutes. The product is then adjusted to a solids content of 85% with 140.6 g of isopropyl alcohol and bleached with 20 g (2.5%) of 30% hydrogen peroxide solution.

Man erhält ein fast farbloses fließfähiges Produkt, das sich durch ei­ne gute Verarbeitbarkeit auszeichnet. Um diese helle Farbe zu errei­chen, sollte während der gesamten Reaktionsdauer Sauerstoff aus dem Reaktionsgefäß ausgeschlossen sein. Es bietet sich ein Durchleiten von ca. 30 l/h Stickstoff an.
Nach sechsmonatigem Stehen bei Raumtemperatur konnten keine Separa­tionserscheinungen beobachtet werden. Das Produkt war gleichbleibend fließfähig.An almost colorless, flowable product is obtained which is characterized by good processability. In order to achieve this bright color, oxygen should be excluded from the reaction vessel during the entire reaction period. A flow of approx. 30 l / h nitrogen is recommended.
After standing for six months at room temperature, no signs of separation were observed. The product was consistently flowable.

Beispiel 2Example 2

Man verfährt wie unter Beispiel 1 beschrieben, nur werden anstelle des Talgfettsäuremethylesters 6 g Kokosfett (= Glycerintrikokosfettsäure­ester) eingesetzt. Das Produkt ist ebenso fließfähig wie das nach Bei­spiel 1 hergestellte.The procedure is as described in Example 1, except that 6 g of coconut fat (= glycerol tricoconut fatty acid ester) are used instead of the tallow fatty acid methyl ester. The product is just as flowable as that produced according to Example 1.

Beispiel 3Example 3

Man verfährt wie unter Beispiel 1 beschrieben. Anstelle des Talgfett­säuremethylesters werden 5 g Ölsäureethylester eingesetzt. Man erhält ein Produkt, daß in seinen Eigenschaften dem nach Beispiel 1 herge­stellten vergleichbar ist.The procedure is as described in Example 1. Instead of the tallow fatty acid methyl ester, 5 g of oleic acid ethyl ester are used. A product is obtained which is comparable in its properties to that prepared according to Example 1.

Claims (4)

1. Verfahren zur Herstellung von Trialkanolamindifettsäureestern durch Umsetzung von Triethanolamin mit 1,5 bis 2,5 Äquivalenten Fett­säure,
dadurch gekennzeichnet,
daß man die Umsetzung in Gegenwart von 0,05 bis 5,0 Gewichtspro­zent, bezogen auf die Gesamtmischung, eines Fettsäureesters vornimmt.1. Process for the preparation of trialkanolamine difatty acid esters by reacting triethanolamine with 1.5 to 2.5 equivalents of fatty acid,
characterized,
that one carries out the reaction in the presence of 0.05 to 5.0 percent by weight, based on the total mixture, of a fatty acid ester. 2. Verfahren zur Herstellung von Trialkanolamindifettsäureestern nach Anspruch 1,
dadurch gekennzeichnet,
daß die Fettsäuren der Fettsäureester 4 bis 24 Kohlenstoffatome enthalten.2. A process for the preparation of trialkanolamine difatty acid esters according to claim 1,
characterized,
that the fatty acids of the fatty acid esters contain 4 to 24 carbon atoms. 3. Verfahren zur Herstellung von Trialkanolamindifettsäureestern nach Anspruch 1 oder 2,
dadurch gekennzeichnet,
daß die Alkohole der Fettsäureester 1- bis 6wertige Alkohole mit 1 bis 8 Kohlenstoffatomen sind.3. A process for the preparation of trialkanolamine difatty acid esters according to claim 1 or 2,
characterized,
that the alcohols of the fatty acid esters are 1- to 6-valent alcohols with 1 to 8 carbon atoms. 4. Verwendung der aus den Triethanolamindifettsäureestern der Ansprüche 1 bis 3 durch übliche Quarternisierung erhaltenen quarternären Ammoniumverbindungen als Wäscheweichspülmittel.4. Use of the quaternary ammonium compounds obtained from the triethanolamine difatty acid esters of claims 1 to 3 by conventional quaternization as fabric softener.
EP88106112A 1987-06-19 1988-04-16 Process for preparing fatty acid diesters of a trialcanolamine and their use Expired - Lifetime EP0295385B1 (en)

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AT88106112T ATE61565T1 (en) 1987-06-19 1988-04-16 PROCESS FOR THE PREPARATION OF TRIALKANOLAMINE DIFATTY ESTERS AND THEIR USE.

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DE3720332 1987-06-19
DE19873720332 DE3720332A1 (en) 1987-06-19 1987-06-19 METHOD FOR PRODUCING TRIALKANOLAMINE DIFETIC ACID ESTERS AND THE USE THEREOF

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AT (1) ATE61565T1 (en)
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DE (2) DE3720332A1 (en)
ES (1) ES2019855B3 (en)

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WO1991001295A1 (en) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Process for preparing quaternary ammonium compounds
EP0420465A2 (en) * 1989-09-19 1991-04-03 Unilever Plc Softening agent for fabrics
EP0498050A2 (en) * 1991-01-17 1992-08-12 Hüls Aktiengesellschaft Aqueous emulsions comprising fatty acid esters of N-methyl-N,N,N-trihydroxyethyl-ammonium-methyl-sulfate
WO1994002575A1 (en) * 1992-07-27 1994-02-03 Henkel Kommanditgesellschaft Auf Aktien Foaming detergent mixtures
WO1994007978A1 (en) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Process for producing powdered or granular detergent mixtures
EP0604726A1 (en) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Process for the quaternisation of fatty acid esters of triethanolamine and imidazolinamides in alkoxylated fats or oils as the reaction medium and the use of the reaction mixture as a fabric conditioner component
EP0718275A1 (en) * 1994-12-23 1996-06-26 Hüls Aktiengesellschaft Quaternary fatty-acid triethanolamine esters
WO1998052907A1 (en) * 1997-05-19 1998-11-26 The Procter & Gamble Company Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners
WO1999035120A1 (en) * 1998-01-09 1999-07-15 Witco Corporation Novel quaternary ammonium compounds, compositions containing them, and uses thereof
WO1999058492A1 (en) * 1998-05-13 1999-11-18 Cognis Deutschland Gmbh Ethoxylated quaternary ester compounds
EP1006103A1 (en) * 1998-12-04 2000-06-07 Cognis Deutschland GmbH Process for preparing esterquat compositions having low viscosity
US6759383B2 (en) 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
WO2015015211A1 (en) * 2013-08-01 2015-02-05 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
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US5516438A (en) * 1989-09-19 1996-05-14 Lever Brothers Company, Division Of Conopco, Inc. Fabric softening
ES2094893T3 (en) * 1991-12-31 1997-02-01 Stepan Europe SURFACES BASED ON QUATERNARY AMMONIUM COMPOUNDS, PREPARATION PROCEDURES, BASES, AND DERIVED SOFTENING COMPOSITIONS.
ZA936280B (en) * 1992-09-16 1995-05-26 Colgate Palmolive Co Fabric softening composition based on higher fatty acid ester and dispersant for such ester
DE4334365A1 (en) * 1993-10-08 1995-04-13 Henkel Kgaa Quaternized fatty acid triethanolamine ester salts with improved water solubility
DE4405702A1 (en) * 1994-02-23 1995-08-24 Witco Surfactants Gmbh Highly concentrated aqueous fabric softener with improved storage stability
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
DE4430721A1 (en) * 1994-08-30 1996-03-07 Hoechst Ag Car gloss desiccant
US5503756A (en) * 1994-09-20 1996-04-02 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
US5916863A (en) 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
JP2000512287A (en) * 1996-06-12 2000-09-19 アクゾ ノーベル ナムローゼ フェンノートシャップ Method for producing ester quartz
DE19855366A1 (en) 1998-12-01 2000-06-08 Witco Surfactants Gmbh Low-concentration, highly viscous aqueous fabric softener
US6271185B1 (en) 1999-10-29 2001-08-07 Cargill, Incorporated Water soluble vegetable oil esters for industrial applications
US7211556B2 (en) * 2004-04-15 2007-05-01 Colgate-Palmolive Company Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient
ATE468320T1 (en) 2005-03-14 2010-06-15 Akzo Nobel Nv REMOVAL OF SULFUR DIOXIDE RESIDUE FROM DIMETHYL SULFATE
US8231864B2 (en) 2005-06-29 2012-07-31 Colgate-Palmolive Company Oligomeric amidoamines or amidoquats for fabric or hair treatment compositions
CN102336675A (en) * 2010-07-21 2012-02-01 博兴华润油脂化学有限公司 Production method of esterquats
EP3181667A1 (en) 2015-12-18 2017-06-21 Kao Corporation, S.A. Fabric softener active compositions
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EP3418354B1 (en) * 2017-06-20 2020-06-03 Kao Corporation, S.A. Fabric softener active compositions
PT3418355T (en) 2017-06-20 2020-07-27 Kao Corp Sa Fabric softener active compositions
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US11434193B2 (en) 2018-06-26 2022-09-06 Evonik Operations Gmbh Preparation method for esterquats based on oil
WO2023014694A1 (en) 2021-08-02 2023-02-09 The Procter & Gamble Company Water insoluble fibrous articles comprising active agents

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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001295A1 (en) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Process for preparing quaternary ammonium compounds
EP0420465A2 (en) * 1989-09-19 1991-04-03 Unilever Plc Softening agent for fabrics
EP0420465A3 (en) * 1989-09-19 1993-02-24 Unilever Plc Softening agent for fabrics
EP0498050A2 (en) * 1991-01-17 1992-08-12 Hüls Aktiengesellschaft Aqueous emulsions comprising fatty acid esters of N-methyl-N,N,N-trihydroxyethyl-ammonium-methyl-sulfate
EP0498050A3 (en) * 1991-01-17 1992-08-26 Huels Aktiengesellschaft Aqueous emulsions comprising fatty acid esters of n-methyl-n,n,n-trihydroxyethyl-ammonium-methyl-sulfate
US5437801A (en) * 1991-01-17 1995-08-01 Huels Aktiengesellschaft Aqueous emulsions containing fatty acid esters of N-methyl-N,N,N-trihydroxyethyl ammonium methyl sulfate
US5580850A (en) * 1992-07-27 1996-12-03 Henkel Kommanditgesellschaft Auf Aktien Foaming detergent mixtures
WO1994002575A1 (en) * 1992-07-27 1994-02-03 Henkel Kommanditgesellschaft Auf Aktien Foaming detergent mixtures
WO1994007978A1 (en) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Process for producing powdered or granular detergent mixtures
EP0604726A1 (en) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Process for the quaternisation of fatty acid esters of triethanolamine and imidazolinamides in alkoxylated fats or oils as the reaction medium and the use of the reaction mixture as a fabric conditioner component
US5443631A (en) * 1992-12-23 1995-08-22 Huels Aktiengesellschaft Process for the quaternization of triethanolamine fatty acid esters and imidazolinamides and the use of the reaction mixtures in laundry softener compositions
US5705663A (en) * 1994-12-23 1998-01-06 Servo Delden B.V. Quaternized triethanolamine difatty acid esters
EP0718275A1 (en) * 1994-12-23 1996-06-26 Hüls Aktiengesellschaft Quaternary fatty-acid triethanolamine esters
WO1998052907A1 (en) * 1997-05-19 1998-11-26 The Procter & Gamble Company Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners
US7015187B2 (en) 1997-05-19 2006-03-21 The Procter & Gamble Company Fabric softening compound
US6521589B2 (en) 1997-05-19 2003-02-18 The Procter & Gamble Company Quaternary fatty acid triethanolamine ester salts and their use as fabric softeners
EP1045891A4 (en) * 1998-01-09 2003-01-22 Goldschmidt Chemical Corp Novel quaternary ammonium compounds, compositions containing them, and uses thereof
EP1045891A1 (en) * 1998-01-09 2000-10-25 Goldschmidt Chemical Corporation Novel quaternary ammonium compounds, compositions containing them, and uses thereof
WO1999035120A1 (en) * 1998-01-09 1999-07-15 Witco Corporation Novel quaternary ammonium compounds, compositions containing them, and uses thereof
WO1999058492A1 (en) * 1998-05-13 1999-11-18 Cognis Deutschland Gmbh Ethoxylated quaternary ester compounds
EP1006103A1 (en) * 1998-12-04 2000-06-07 Cognis Deutschland GmbH Process for preparing esterquat compositions having low viscosity
US6759383B2 (en) 1999-12-22 2004-07-06 The Procter & Gamble Company Fabric softening compound
US8618316B1 (en) 2004-03-05 2013-12-31 Stepan Company Low temperature ramp rate ester quat formation process
WO2015015211A1 (en) * 2013-08-01 2015-02-05 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
US10550304B2 (en) 2013-08-01 2020-02-04 M-I Drilling Fluids Uk Limited Quaternary ammonium compounds and gas hydrate inhibitor compositions
EP4282854A1 (en) 2022-05-25 2023-11-29 Unión Deriván, S.A. Process for the production of esterquats

Also Published As

Publication number Publication date
ES2019855B3 (en) 1991-12-01
ATE61565T1 (en) 1991-03-15
US4830771A (en) 1989-05-16
ES2019855A4 (en) 1991-07-16
DE3720332A1 (en) 1988-12-29
EP0295385B1 (en) 1991-03-13
AU1813188A (en) 1988-12-22
DE3861985D1 (en) 1991-04-18

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