Synthesis of eugenyl acetate by,enzymatic reactions in supercritical carbon dioxide

Author(s)

dos Santos, Philipe ; Zabot, Giovani L. ; Meireles, M. Angela A. ; Mazutti, Marcio A. ; Martinez, Julian

• Document type: Journal article
• Source: Biochemical Engineering Journal; v. 114, p. 1-9, OCT 15 2016.
• Web of Science Citations: 13

Abstract

Supercritical carbon dioxide (SC-CO2) as reaction medium has gained attention in the production of terpenic esters catalyzed by lipases. Therefore, this work investigated the production of eugenyl acetate by esterification of eugenol and acetic anhydride in SC-CO2 using two commercial lipases (Lipozyme 435 and Novozym 435) as catalysts. The influence of enzyme concentration (1-10% weight/weight), substrates' molar ratio (1:1 to 5:1), temperature (40-60 degrees C) and pressure of SC-CO2 (10-30 MPa) on the esterification rate (X; %) and specific productivity (SP; kg of product/kg of catalyst x hour) were evaluated. A home-made high-pressure stirred-batch reactor (100 ml) was used in the experiments. The use of Novozym 435 achieved higher conversion and specific productivity of eugenyl acetate than Lipozyme 435. An excess of acetic anhydride (5:1 M/M) and high enzyme concentration (10%) achieved higher esterification rates than the lowest conditions (1% and 1:1 M/M). The optimal temperatures and pressure for the synthesis of eugenyl acetate in SC-CO2 were 50 and 60 degrees C at 10 MPa, respectively. The phase behavior of the reaction system and the synthesis in organic medium were also studied. Kinetic experiments performed at 40, 50 and 60 degrees C indicated that the reaction follows the simple Ping-Pong Bi-Bi mechanism and the affinity of acetic anhydride to enzyme was larger than that of eugenol. (C) 2016 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 09/54137-1 - Acquisition of a particle size/distribution analyzer, a zeta potential measurement system, a spray dryer, and an ultra-high-pressure liquid chromatograph/mass spectrometer
• Grantee: Miriam Dupas Hubinger
• Support Opportunities: Multi-user Equipment Program
• FAPESP's process: 15/11932-7 - Integration of high pressure extraction to separation operations for the recovery of by-products from fruit processing
• Grantee: Julian Martínez
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/02203-6 - Development of equipments for extraction, particle formation and chemical reactions using pressurized fluids
• Grantee: Julian Martínez
• Support Opportunities: Regular Research Grants