Microwave assisted enzymatic kinetic resolution of (±)-1-phenyl-2-propyn-1-ol in nonaqueous media.
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.
Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
Saravanan
S
Devendran
Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
Ganapati D
GD
Yadav
D000438:Alcohols / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D004800:Enzymes, Immobilized; D004951:Esterification; D005656:Fungal Proteins / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D008872:Microwaves; D020005:Propanols / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000438:Alcohols; D000480:Alkynes; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D006586:Hexanes; D020005:Propanols; D012997:Solvents; D014753:Vinyl Compounds; C026385:n-hexane; C028255:propargyl alcohol; C093667:Novozyme 435; D008049:Lipase; C431349:lipase B, Candida antarctica; C011566:vinyl acetate