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Chemically and enzymatically catalyzed synthesis of C 6 –C 10 alkyl benzoates
Author(s) -
Krause Przemyslaw,
Hilterhaus Lutz,
Fieg Georg,
Liese Andreas,
Bornscheuer Uwe
Publication year - 2009
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.200800135
Subject(s) - catalysis , chemistry , benzoic acid , organic chemistry , kinetics , chemical kinetics , benzoates , alkyl , esterase , chemical synthesis , chemical reaction , chemical stability , reaction rate , enzyme , biochemistry , physics , quantum mechanics , in vitro
The esterification of benzoic acid with n ‐hexanol, n ‐octanol, 2‐ethyl hexanol and n ‐decanol was investigated in detail. An analysis of the reaction kinetics of esterification in the presence of different commercially available chemical catalysts was carried out. The effects of catalyst type and loading on the reaction rate were studied. Although the considered reaction is bimolecular, it showed a first‐order behavior, and a linear dependence with respect to the catalyst concentration was observed. Hence, a new approach is presented to describe the reaction kinetics accurately over a wide range. The application of biotechnological synthesis applying different enzymes as catalysts offers an interesting alternative besides chemical synthesis. Especially an esterase from Bacillus subtilis immobilized on Sepabeads EC‐EP showed high stability and was applied for 2 days in the synthesis of hexyl benzoate. Nevertheless, the chemical reaction route remains superior with respect to the catalyst activities under the applied conditions, which were 25 kU/g for the chemical reaction and 0.7 kU/g for the best enzymatic conversion.