Synthesis of fatty alcohol esters of alpha-hydroxy...

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound

Reexamination Certificate

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C435S135000, C554S174000

Reexamination Certificate

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07863025

ABSTRACT:
The present invention provides a novel approach for the preparation of fatty alcohol esters of α-hydroxy carboxylic acids. In one form of the invention, the target fatty alcohol ester of α-hydroxy carboxylic acid is produced by converting a lower alkyl ester of α-hydroxy carboxylic acid into a fatty alcohol ester of α-hydroxy carboxylic acid via alcoholysis (i.e., transesterification). The transesterification process is an equilibrium reaction, catalyzed chemically (i.e., with acids or bases) or enzymatically, that is shifted in the desired direction to produce the desired product. One preferred way of shifting the reaction in the direction of the desired product is by reducing the concentration of one of the products (e.g., distillation of a lower-boiling alcohol as soon as it is formed). Another preferred way of shifting the reaction in the direction of the desired product is by increasing the concentration of one of the reactants (e.q., adding more of the starting ester).

REFERENCES:
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patent: 2002/0055650 (2002-05-01), Hidaka et al.
patent: 2143940 (2000-05-01), None
patent: 2006044926 (2006-04-01), None
Ramalinga et al., “A mild and efficient method for esterficiaton and transesterification catalyzed by iodine.”. Tetrahedron Letters. vol. 43, pp. 879-882, 2002.
Torres et al., “Part I. Enzymatic synthesis of lactate and glycolate esters of fatty alcohols”, Enzyme and Microbial Techonlogy vol. 25, pp. 745-752, 2002.
Morrison & oyd, 4thEd. 1983, pp. 837-838.
Kayer et al., Journal of Organic Chemistry (1999), 64(18), 6603-6608.
International Search Report dated Aug. 8, 2006 from International Application No. PCT/US05/37504.

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