Competitive lipase-catalyzed ester hydrolysis and ammoniolysis in organic solvents; equilibrium model of a solid-liquid-vapor system.
Enzymatic ester hydrolysis and ammoniolysis were performed as competitive reactions in methyl isobutyl ketone without a separate aqueous phase. The reaction system contained solid ammonium bicarbonate, which dissolved as water, ammonia, and carbon dioxide. During the reaction an organic liquid phase, a vapor phase, and at least one solid phase are present. The overall equilibrium composition of this multiphase system is a complex function of the reaction equilibria and several phase equilibria. To gain a quantitative understanding of this system a mathematical model was developed and evaluated. The model is based on the mass balances for a closed batch system and straightforward relations for the reaction equilibria and the solubility equilibria of ammonium bicarbonate, the fatty acid ammonium salt, water, ammonia, and carbon dioxide. For butyl butyrate as a model ester and Candida antarctica lipase B as the biocatalyst this equilibrium model describes the experiments satisfactorily. The model predicts that high equilibrium yields of butyric acid can be achieved only in the absence of ammoniolysis or in the presence of a separate water phase. However, high yields of butyramide should be possible if the water concentration is fixed at a low level and a more suited source of ammonia is applied.
Litjens
M J
MJ
Kluyver Laboratory for Biotechnology, Delft University of Technology, Julianalaan 67, NL-2628 BC Delft, The Netherlands.
Sha
M
M
Straathof
A J
AJ
Jongejan
J A
JA
Heijnen
J J
JJ
D000641:Ammonia / Q000737:chemistry*; D004952:Esters; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D008956:Models, Chemical; D009930:Organic Chemicals / Q000737:chemistry*; D012995:Solubility; D012997:Solvents / Q000737:chemistry*
D004952:Esters; D009930:Organic Chemicals; D012997:Solvents; D000641:Ammonia; D008049:Lipase