Microwave Assisted Enzymatic Kinetic Resolution of (±)‎-1-Phenyl-2-propyn-1-ol in Nonaqueous Media

Abstract EN

Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis.

Lipases from different microbial origins were employed for the kinetic resolution of (R/S)-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n-hexane as solvent.

Vinyl acetate was the most effective among different acyl esters studied.

The effect of various parameters was studied in a systematic manner.

Definite synergism between microwave and enzyme was observed.

The initial rate was improved around 1.28 times under microwave irradiation than conventional heating.

Under optimum conditions, maximum conversion (48.78%) and high enantiomeric excess (93.25%) were obtained in 2 h.

From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition.

Kinetic parameters were obtained by using nonlinear regression.

This process is green, clean, and easily scalable as compared to the chemical process.