Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1998-09-28
1999-12-28
Carr, Deborah D
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554148, C07C 5100
Patent
active
060083921
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to a process for the alkoxylation of fatty acid alkyl esters in the presence of double-layer mixed oxides and selected co-catalysts.
DISCUSSION OF RELATED ART
Alkoxylated alkyl esters, preferably so-called methyl ester ethoxylates, are known nonionic surfactants which have recently acquired considerable interest by virtue of their excellent washing performance. Relevant reviews can be found, for example, in J. Am. Oil Chem. Soc. 56, 873 (1979) and in J. Am. Oil Chem. Soc. 72, 781 (1995).
The addition of alkylene oxides onto compounds containing acidic hydrogen atoms, preferably onto primary alcohols, can be carried out in the presence of various, generally alkaline catalysts. Typical examples are potassium hydroxide or sodium methylate, which are added in the form of alcoholic solutions, or heterogeneous layer compounds of the hydrotalcite type which are introduced into the reaction mixture in the form of solids. By contrast, the insertion of alkylene oxides into the carbonyl ester bond is far more difficult and can only be achieved using special catalysts.
The use of calcined or fatty-acid-modified hydrotalcites for the alkoxylation of fatty acid esters is known from EP-B1 0 339 425 and EP-B1 0 523 089 (Henkel). According to DE-A1 44 46 064 (Lion), the ethoxylation of methyl esters is carried out in the presence of mixed metal oxides which have been surface-modified with metal hydroxides or metal alkoxides. However, these processes are unsatisfactory for operation on an industrial scale because, where methyl esters are used, a significant proportion of the starting material always remains unreacted and small amounts of methyl monoglycol esters, from which methyl glycol can be released by hydrolysis, are formed. In many cases, the homolog distribution is also unsatisfactory because it does not have a pronounced maximum and comprises excessive proportions of species with relatively low and relatively high degrees of ethoxylation.
Accordingly, the problem addressed by the present invention was to provide new catalysts for the production of alkoxylated alkyl esters with a narrow homolog distribution which would be free from unreacted alkyl esters and alkyl monoglycol esters.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of alkoxylated fatty acid alkyl esters corresponding to formula (I): ##STR1## where R.sup.1 CO is a linear or branched acyl group containing 6 to 22 carbon atoms and 0 and/or 1, 2 or 3 double bonds, R.sup.2 is hydrogen or a methyl group, R.sup.3 is a linear or branched alkyl group containing 1 to 22 carbon atoms and n is a number of--on average--1 to 20, in which fatty acid esters are reacted with ethylene and/or alkylene oxides in the presence of double-layer mixed-oxide catalysts, characterized in that co-catalysts selected from the group consisting of lithium hydroxide, alkaline earth metal salts and tin salts are used.
It has surprisingly been found that, by adding the co-catalysts mentioned to the known double-layer mixed-oxide catalysts, more particularly of the hydrotalcite type, the proportion both of unreacted alkyl esters and of alkyl monoglycol esters is significantly reduced. At the same time, a particularly narrow homolog distribution is obtained.
The fatty acid alkyl esters used as starting materials correspond to formula (II): from saturated and/or unsaturated fatty acids containing 6 to 22 and preferably 12 to 18 carbon atoms and alcohols containing 1 to 22 and preferably 1 to 4 carbon atoms. Typical examples are methyl, ethyl, propyl, butyl and/or stearyl esters of caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and the technical mixtures thereof obtained, for example, in the pressure hydrolysis of na
REFERENCES:
patent: 5292910 (1994-03-01), Raths et al.
Weil, et al., J. Am. Oil. Chem. Soc., Sep., 1979, vol. 56, pp. 873-877.
Hama, et al., J. Am. Oil. Chem. Soc. AOCS Press (1995), vol. 72, No. 7, pp. 781-784.
Behler Ansgar
Folge Almud
Carr Deborah D
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Szoke Ernest G.
Trzaska Steven J.
LandOfFree
Process for preparing alkoxylated fatty acid alkyl esters does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for preparing alkoxylated fatty acid alkyl esters, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing alkoxylated fatty acid alkyl esters will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2383442