Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1996-09-16
1999-02-09
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554103, 554107, 564281, 564291, 564296, C07C22700
Patent
active
058697160
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP 95/00861 filed May 9, 1995.
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for the production of esterquats, in which fatty acid glycerol esters are directly transesterified with tertiary hydroxyamines and then quaternized, and to the use of the products for the production of surface-active formulations.
2. Statement of Related Art
In recent years, quaternized fatty acid triethanolamine ester salts, socalled "esterquats", have acquired increasing significance as in C.R. CED Congress, Barcelona, 167 (1992) and R. Puchta in C.R. CED Congress, Sitges, 59 (1993)!.
According to the teaching of International patent application WO 91/01295 (Henkel), esterquats are normally produced from triethanolamine or adducts of ethylene oxide with triethanolamine which, in a first step, are partly esterified with linear C.sub.16/18 fatty acids in the presence of hypophosphorous acid and subsequently treated with air. The fatty acid triethanolamine esters are then quaternized, for example with alkyl halides or, preferably, dialkyl sulfates.
Instead of fatty acids themselves, it is desirable for economic reasons directly to use natural fats and oils, from which the fatty acids are obtained, as starting materials for the production of esterquats. However, according to studies conducted by applicants, application of this principle on an industrial scale has hitherto been prevented by the fact that transesterification in the presence of the alkaline catalysts typically used for this type of reaction, namely potassium hydroxide or sodium methylate, generally involves overly long reactor possession times and, in general, leads to discolored products which have to be bleached in an additional, expensive process step.
Accordingly, the problem addressed by the present invention was to provide a process for the production of esterquats based on fats and oils as starting materials which would not have any of the disadvantages mentioned above.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of esterquats in which fatty acid glycerol esters are subjected to transesterification with hydroxyfunctionalized tertiary amines in the presence of alkali metal and/or alkaline earth metal borohydrides and hypophosphorous acid or alkali metal and/or alkaline earth metal salts thereof and, optionally, free fatty acid and the resulting products are quaternized in known manner.
It has surprisingly been found that the use of borohydrides as opposed to other conventional transesterification catalysts leads to a quick and complete reaction which, in addition, gives reaction products that are distinguished by particularly high color quality. In addition, the process according to the invention affords the advantage that fats and oils can be directly used instead of fatty acids which increases the economy of the process.
Esterquats are generally understood to be quaternized fatty acid triethanolamine ester salts. These are known substances which may be obtained by the relevant methods of preparative organic chemistry, cf. International patent application WO 91/01295 (Henkel). According to this document, triethanolamine is partly esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and the fatty acid triethanolamine esters are subsequently quaternized with dimethyl sulfate or ethylene oxide. U.S. Pat. No. 3,915,867, U.S. Pat. No. 4,370,272, EP-A2 0 239 910, EP-A2 0 293 955, EP-A2 0 295 739 and EP-A2 0 309 052 are cited at this juncture as representative of the extensive prior art on this subject.
The quaternized fatty acid triethanolamine ester salts correspond to formula (I): ##STR1## in which R.sup.1 CO is an acyl radical containing 6 to 22 carbon atoms, R.sup.2 and R.sup.3 independently of one another represent hydrogen or have the same meaning as R.sup.1 CO, R.sup.4 is an alkyl radical containing 1 to 4 carbon atoms or a (CH.sub.2 --CH.sub.2 O).sub.q H group, m, n and p have a combined value o
REFERENCES:
patent: 3915867 (1975-10-01), Kang et al.
patent: 4370272 (1983-01-01), Wechsler et al.
patent: 5437801 (1995-08-01), Luders et al.
O. Ponsati, C.R.CED Congress, Barcelona, 1992, p. 167.
R. Puchta, et al.,C.R. CED Congress, Sitges, 1993, p. 59.
Bigorra Llosas Joaquim
Pi Subirana Rafael
Trius Oliva Antonio
Carr Deborah D.
Drach John E.
Geist Gary
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
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