Mechanistic investigations of the reaction network in chemo-bio catalyzed synthesis of R-1-phenylethyl acetate

A. Kirilin*, S. Sahin, A. Tokareva, P. Mäki-Arvela, K. Kordas, A. R. Leino, A. Shchukarev, J. P. Mikkola, L. M. Kustov, T. Salmi, D. Yu Murzin

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

The kinetics and reaction network of the one-pot synthesis of R-1-phenylethyl acetate was inves-tigated at 70°C in toluene over a combination of three different catalysts: PdZn/Al2O3 as a catalyst for acetophenone hydrogenation, lipase as an enzymatic catalyst for R-1-phenylethanol acylation with ethyl acetate and Ru/Al2O 3 as a racemization catalyst for S-1-phenylethanol. In addition to the desired reactions, other reactions, namely hydrogenolysis and dehydration of (R, S)-1-phenylethanol and debenzylation of (R, S)-1- phenylethyl acetate also occurred. The kinetic results revealed that ethylbenzene formation was enhanced with higher amounts of PdZn/Al2O3, whereas lipase did not catalyze ethylbenzene formation. Furthermore, ethylbenzene was formed in the hydrogenolysis of (R, S)-phenylethanol and in the debenzylation of (R, S)- 1-phenyl-ethylacetate over Pd/Al2O3 catalyst. The presence of Ru/Al2O3 catalyst, in which Ru was in the oxi- dation state of 3+, enhanced the formation of R-1-phenylethyl acetate, although no clear racemization of S-1-phenylethanol during the one-pot synthesis of R-1-phenylethyl acetate was observed. Dynamic kinetic resolution of (R, S)-1-phenylethanol in toluene, was, however, demonstrated over Ru/Al 2O3 and lipase.

Original languageEnglish
Pages (from-to)809-815
Number of pages7
JournalKinetics and Catalysis
Volume51
Issue number6
DOIs
Publication statusPublished - Dec 2010
MoE publication typeA1 Journal article-refereed

Fingerprint Dive into the research topics of 'Mechanistic investigations of the reaction network in chemo-bio catalyzed synthesis of R-1-phenylethyl acetate'. Together they form a unique fingerprint.

Cite this