Enzymatic synthesis of cinnamyl propionate from cinnamyl alcohol and propionic acid in a solvent free condition
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Enzymatic synthesis of cinnamyl propionate from cinnamyl alcohol and propionic acid in a solvent free condition Meera T. Sose1 · Sarita D. Gawas1 · Virendra K. Rathod1 Received: 31 December 2019 / Accepted: 26 March 2020 © Springer Nature Switzerland AG 2020
Abstract This work illustrates the synthesis of cinnamyl propionate in the presence of lipase biocatalyst. The esterification reaction was performed in a solvent free condition with cinnamyl alcohol and propionic acid using fermase CALB™ 10000, a commercial lipase. Experiments were conducted to study different operating parameters such as enzyme loading, temperature, mole ratio, speed of agitation, and reusability of enzyme. Various kinetic parameters affecting esterification reaction were evaluated to synthesize cinnamyl propionate. It has been observed that the data obtained follows random bi-bi mechanism with inhibition by both acid and alcohol substrate. The highest conversion of cinnamyl propionate obtained is 87.89% after 7 h at optimum parameters: enzyme loading 2% (w/v), temperature 60 °C, acid to alcohol ratio 1:3, molecular sieves 6% (w/v) and agitation speed 200 rpm. Limitation of diffusion mass transfer between the enzyme surface and substrate does not show a significant effect on reaction kinetics. The study of repeated use of enzyme shows that it maintains 90% of its catalytic activity after six successive batches. Keywords Esterification · Cinnamyl propionate · Enzymatic catalysis · Lipase · Kinetics · Ping-pong bi-bi mechanism
1 Introduction The sweet aroma esters are short-chain compounds usually used in food products like squashes, beverages, jams, candies, jellies, syrup, chocolates, ice-creams, and dairy products as a flavoring agent [1]. Similarly, the fatty acids derived long-chain esters are generally used in pharmaceuticals, cosmetics, surfactants [2], and also in lubricants, plasticizers, water-resistant agents, diesel additives, hydraulic fluids as reaction medium [3, 4]. Likewise, several esters of short-chain fatty acid, demonstrate fruity odor characteristic, which include ethyl butyrate (strawberry or pineapple flavor) [5], 1-methyl butyrate (apple or pineapple flavor) [6], butyl butyrate [7], ethyl hexanoate (pineapple flavor) [8], isoamyl isovalerate (apple flavor) [9], isoamyl acetate [10] and (banana flavor) isoamyl butyrate [10, 11]. The several cinnamyl esters having aroma characteristics
are used in personal care products. In previous literature, cinnamyl acetate is synthesized by trans-esterification of vinyl acetate and cinnamyl alcohol. This reaction can be carried out by either chemical or biochemical, with the enzyme as a bio-catalyst [12, 13]. Lipases are well-known as catalyst for esterification, transesterification, and hydrolysis [8]. Cinnamyl propionate is a vital ingredient used for formulation in perfume mostly in oriental fragrance type as a modifier for the more pronounced, spicy items. It blends with Oak moss into a very pleasant composition, particularly in the presence of clove bud, bay leaf oil, etc. an
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