Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1996-08-15
1997-10-28
Wax, Robert A.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435 18, 435134, 435 72, 435195, 435197, 435198, 435921, C12P 1944, C07H 1504
Patent
active
056817274
DESCRIPTION:
BRIEF SUMMARY
This application claims benefit of international application PCT/EP95/00555 filed Feb. 15, 1996.
The present invention relates to a process of enzymatically preparing fatty acid esters of alkyl glycosides.
Such a process is known from International Patent Application WO-A-8901480 (Novo Industri) in which alkyl glycosides having an alkyl group with 2-6 carbon atoms are reacted with a C4-C24 (preferably C6-C22) fatty acid or a lower alkyl ester thereof in the presence of a hydrolase, which preferably is a lipase, which is producable by species of Rhizomucor, Humicola, Pseudomonas or Candida. The enzymes may be applied in a soluble state or in immobilized form. It has been stated that preferably no solvent is used, but that if an organic solvent is used, it should have no deleterious effect on the enzyme. Suggested solvents are ketones (like 2-butanone), hydrocarbons (like pentane, hexane or heptane) and ethers. In two examples 2-butanone is used as a solvent in a large excess compared to the total weight of the reactants. A problem in the technical realisation of the process on an industrial scale is the high viscosity of the alkyl glycoside, which needs to be mixed with the molten fatty acid, which is very difficult, if at all possible. If the amount of fatty acid is increased relative to the alkyl glycoside to increase the reaction efficiency, side-products, such as di-ester, tend to be formed in appreciable amounts.
It has therefore been proposed in International Patent Application WO-A-941575 (Unilever) to first convert the reactants alkyl glycoside and fatty acid into a stable micro-emulsion by means of surface-active agent, which is preferably an anionic or nonionic surface-active agent. In a preferred embodiment, part of the alkyl glycoside fatty acid ester formed is recycled into the reaction to act as the surfactant in the formation of the micro-emulsion. This micro-emulsion is then subjected to the enzymatic esterification reaction, using a lipase, particularly an immobilized lipase.
It has been found, however, that even such micro-emulsions may still exhibit viscosities which are too high to pass them over a fixed bed enzyme catalyst. The convenience of working with micro-emulsions can be retained, however, if a series of interlocking process steps is applied in the enzymatic manufacture of the alkyl glycoside fatty acid esters. Thus it has been found that the viscosity of the micro-emulsions can effectively be reduced by combining the micro-emulsion with an effective amount of a specific viscosity reduction agent, after which the micro-emulsion is passed over a fixed bed hydrolase catalyst under pressure and the final reaction product obtained is subjected to pervaporation. In this way a convenient process is obtained which enables the working with normally high viscosity mixtures and which leads to high yields of the ester in an economically attractive way.
Therefore, the present invention relates to a process of enzymatically preparing fatty acid esters of alkyl glycoside in which a micro-emulsion is formed from a saturated or unsaturated, straight or branched chain fatty acid having from 6 to 22 carbon atoms, a nonionic or anionic surface active agent and an alkyl glycoside in which the alkyl group is a saturated, straight or branched chain alkyl group having from 1 to 8 carbon atoms, which is characterized in that viscosity reducing agent, selected from the group consisting of tertiary butanol, 2-methyl-2-butanol, acetone, 2-butanone, and mixtures thereof, time with a lipase at a temperature of 35.degree. C. to 85.degree. C. and a pressure of up to 20 bar, and at a temperature of 65.degree. C. to 100.degree. C. and a pressure of at least 1 bar.
Preferably the fatty acid is a saturated or unsaturated, straight or branched chain fatty acid, having from 8 to 20 carbon atoms. Also mixtures of fatty acids may be used and the fatty acids may be of a technical grade. The fatty acids may also comprise functional groups, such as hydroxyl groups, amino groups and the like other groups.
The alkyl group
REFERENCES:
Mutua et al. (1993). JAOCS, vol. 70(1): 43-46.
Macrae Alasdair Robin
Poulina Ramires Rolando
Saidha Tekchand
Unichema Chemie B.V.
Wax Robert A.
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