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- Title
Mechanistic investigations of the reaction network in chemo-bio catalyzed synthesis of R-1-phenylethyl acetate.
- Authors
Kirilin, A.; Sahin, S.; Tokarev, A.; Mäki-Arvela, P.; Kordas, K.; Leino, A.; Shchukarev, A.; Mikkola, J.; Kustov, L.; Salmi, T.; Murzin, D.
- Abstract
The kinetics and reaction network of the one-pot synthesis of R-1-phenylethyl acetate was investigated at 70°C in toluene over a combination of three different catalysts: PdZn/AlO as a catalyst for acetophenone hydrogenation, lipase as an enzymatic catalyst for R-1-phenylethanol acylation with ethyl acetate and Ru/AlO 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/AlO, 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/AlO catalyst. The presence of Ru/AlO catalyst, in which Ru was in the oxidation 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/AlO and lipase.
- Subjects
ACETATES; ORGANIC synthesis; STYRENE; HYDROGENATION; CHEMICAL kinetics; HYDROGENOLYSIS; LIPASES
- Publication
Kinetics & Catalysis, 2010, Vol 51, Issue 6, p809
- ISSN
0023-1584
- Publication type
Article
- DOI
10.1134/S0023158410060054