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Large‐scale preparation of ( Z )‐3‐hexen‐1‐yl acetate using Candida antarctica ‐immobilized lipase in hexane
Author(s) -
BourgGarros S.,
Razafindramboa N.,
Pavia A. A.
Publication year - 1998
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(19980820)59:4<495::aid-bit12>3.0.co;2-9
Subject(s) - candida antarctica , lipase , chemistry , yield (engineering) , decantation , chromatography , acetic acid , hexane , triacylglycerol lipase , immobilized enzyme , nuclear chemistry , enzyme , organic chemistry , materials science , metallurgy
A kilogram‐scale synthesis of ( Z )‐3‐hexen‐1‐yl acetate, in hexane, on direct esterification of ( Z )‐3‐hexen‐1‐ol with acetic acid in the presence of 2% (w/w reactants) of an immobilized lipase from Candida antarctica (Novozym 435) is reported. Conversion yields ranging from 92 to 96% were obtained after optimization of various parameters. In that respect, elimination of the water proved crucial. Using at both the laboratory large scale (preparation of 200–400 g of ester) and the pilot scale (1–5 kg) a “reflux” rotary evaporator equipped with a graduated decantation flask, we were able to trap the water evolved during esterification while at the same time monitor the time course of the reaction. As a consequence of both an efficient water trapping and of a gentle dispersion of the immobilized lipase into the reaction medium, the lifetime of the enzyme was significantly prolonged. At the laboratory large scale (LLS), the yield was still ⩾90% after seven consecutive utilizations whereas at the pilot scale (PS), it reached 93% after reusing the enzyme four times. In those conditions, the amount of immobilized enzyme necessary to produce 1 kg of ( Z )‐3‐hexen‐1‐yl acetate was 18 g (1.8%) and 60 g (6%) at the LLS and the PS, respectively. © 1998 John Wiley & Sons, Inc. Biotechnol Bioeng 59: 495–500, 1998.