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

*Korresponderande författare för detta arbete

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

Sammanfattning

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.

OriginalspråkEngelska
Sidor (från-till)809-815
Antal sidor7
TidskriftKinetics and Catalysis
Volym51
Utgåva6
DOI
StatusPublicerad - dec 2010
MoE-publikationstypA1 Tidskriftsartikel-refererad

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