Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1999-06-03
2000-03-07
Carr, Deborah
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 68, 554 70, C07C23100
Patent
active
060342579
DESCRIPTION:
BRIEF SUMMARY
The invention relates to alkoxylated amides, processes for preparing such tertiary amides, their use, especially in detergents, cleaning products and bodycare compositions, and compositions comprising them.
The invention relates also to processes for separating glycerol from reaction mixtures containing glycerol and fatty acid amides, the reaction mixture preferably originating from the above reaction of fatty acid glycerides with amines to produce tertiary amides.
A large number of fatty acid amides and their ethoxylates are known, as is their suitability as surface-active substances. J. H. Weil, N. Pares, W. R. Nobel, F. D. Smith, A. J. Stirton in J. Am. Oil Chem. Soc., 1971, pages 674 to 677 describe fatty acid alkanolamides. Those described in particular are N-methylethanolamides of pelargonic, lauric, palmitic, stearic and oleic acid. Also described are ethylene oxide and propylene oxide adducts of diethanolamides of palmitic, stearic and pelargonic acid. The compounds can be used as constituents of detergent formulations and cosmetics. The compounds were prepared from the methyl esters of the corresponding acids. Ethylene oxide adducts of N-methylethanolamides are not described.
DE-A1-42 16 316 describes tertiary amides and their use as low-foaming wetting agents in the textile industry. The tertiary amides are derived from fatty acids and N-alkylethanolamines having C.sub.3-6 -alkyl radicals. Mention is made in particular of amides of isononanoic acid and N-butylethanolamine, N-hexylethanolamine, N-hexylisopropanolamine and N-(2-ethylhexyl)ethanolamine, which are ethoxylated.
The compounds are used as low-foaming wetting agents in the preparation and finishing of textiles, especially in the dyeshop in the preparation, pretreatment and dyeing of raw product. Tertiary amides of N-methylamines or N-ethylamines are not described. To prepare the tertiary amides, the carboxylic acids are reacted with the amines and are then ethoxylated.
A number of process for preparing fatty acid amides are known. The reaction of fatty acid glycerides with amines to give fatty acid amides and glycerol is known. In many cases the glycerol formed then remains in the product mixture. Processes for separating glycerol from the reaction mixture are also known. JP-A-7332081 describes a process for preparing fatty acid amides in which a natural oil and an amine compound are reacted. For example, linseed oil is reacted with cyclohexylamine, and the resulting solution is poured into ice-cold hydrochloric acid and subjected to extraction with ether. The etherial extract is washed with 5% HCl, 5% Na.sub.2 CO.sub.3 and H.sub.2 O, dried over Na.sub.2 SO.sub.4 and concentrated under reduced pressure. The residue is subjected to fractional distillation in order to give the desired fatty acid amide.
JP-A-7326921 describes a process for the aminolysis of glyceride fats and oils with amines. Glycerol is removed from the equilibrium by forming borate esters of boric acid or boric anhydride. Polymerized glycerol borates settle at the bottom of the reaction mixture.
DE-C-40 19 089 describes a process for direct recovery of fatty acid amides from crude fats and oils, wherein the latter are reacted with diaminoethane or diaminohexane. The reaction product is recrystallized from methanol.
DE-A42 18 837 describes a process for preparing N,N'-bisacylalkylenediamines with pure C chains. In this process, oils and ethylenediamine are reacted in the presence of p-toluenesulfonic acid as catalyst. The yellowish waxlike crude product obtained is then dispersed in hot water and filtered through a suction filter. The filtrate is a virtually nitrogen-free glycerol concentrate.
WO 96/18608 describes the synthesis of fatty acid N-alkylamides. The amides are prepared by reacting oils with amines. The crystalline fatty acid N-alkylamides are isolated either by filtration or by addition of hexane, in which case a hexane phase containing the fatty acid N-alkylamide is separated by decantation from a glycerol-containing phase.
In the above processes glycerol is
REFERENCES:
J.K. Weil, et al., Journal of the American Oil Chemists' Society, pp. 674-677, "Tallow Alkanolamides: Preparation and Effect on Surfactant Solutions.sup.1," 1971.
Chemical Abstract, AN 48459U-DE, JP 7326921, Aug. 17, 1973.
Chemical Abstract, AN 61525U-B, JP 7332081, Oct. 04, 1973.
Chemical Abstract, AN 93-406545/51, DE 4218837, Dec. 16, 1993.
Chemical Abstract, AN 96-300543/30, WO 96/18608-A1, Jun. 20, 1996.
aus dem Kahmen Martin
Baur Richard
Borzyk Oliver
Burkhart Bernd
Oetter Gunter
BASF - Aktiengesellschaft
Carr Deborah
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