Synthesis of geranyl acetate by transesterification of geraniol with ethyl acetate over Candida antarctica lipase as catalyst in solvent‐free system

Abstract

Increasing environmental awareness has forced researchers to minimize the use of organic solvents in chemical synthesis. Modern biocatalysis is a way to develop clean catalytic technologies. A process operating in solvent‐free condition using reusable biocatalyst, will be useful for the fragrance and flavour industry, which requires stringent specifications on impurities. A direct transesterification reaction of geraniol with ethyl acetate was carried out to produce geranyl acetate in a batch reactor using different immobilized enzymes. Among these, Novozyme 435 was the best catalyst for the synthesis of geranyl acetate in a solvent‐free medium. Parametric studies were conducted to optimize the conversion and yield. Overall, 83% conversion of geraniol with 100% selectivity to geranyl acetate was obtained at a mole ratio of 1:7 of geraniol to ethyl acetate, using 12.7 g L−1 Novozyme 435 at 60 °C for 2 h. At higher concentrations of acyl donor, it was noticed that the conversion of geranyl acetate was increased. The Lineweaver–Burk plots suggested a ternary complex with inhibition by ethyl acetate. The process is green, clean, and useful to the perfume and flavour industries.

RETRACTED: Study on the quality formation mechanism of Zao chili with enhanced fermentation by Lactipllantbacillus plantarum 5-1

“…Bornyl acetate has cool pine aroma and camphor like smell, which does not changed significantly with fermentation time. Geranyl acetate can be synthesized from geraniol and ethyl acetate by transesterification under the catalysis of Candida antarctica lipase ( Bhavsar & Yadav, 2019 ). The changes of geranyl acetate during fermentation were consistent with those of geraniol and Candida .…”

Enzyme Biocatalysis for Sustainability Applications in Reactors: A Systematic Review

“…68 The synthesis of the flavoring ester is conducted at 60 °C at 2 h with a yield of 83% and can be reused up to three cycles. 20 The agitation method of the reactor system is also found to affect the residence time and the product yield of the reaction. In the review conducted, there are two distinct methods of agitation in a batch reactor, namely, magnetic stirrer and orbital shaker.…”

Optimization of Enzymatic Synthesis of Neryl Acetate in a Solvent Free System

“…The lipase catalyzed synthesis of flavour and fragrance compounds involved interactions among several variables, therefore traditional methods were inefficient for optimization of the reaction. Single factor method, such as the molar ratio, enzyme loading and temperature, was found as significant parameter affecting transesterification conversion of geraniol-isomers of nerol [11]. Response surface methodology was further selected here.…”

“…The conversion was increased with the enzyme loading from 1.0% to 3.0%. However, further increase of enzyme loading would reduce the conversion rate of nerol to pases, so an increase in ethyl acetate amount would inhibit the enzyme activity and decrease the conversion rate of nerol [11]. Figure 5 showed the combined effect of temperature and molar ratio on the conversion rate in 120 min.…”