TY - JOUR
T1 - Mechanistic investigations of the reaction network in chemo-bio catalyzed synthesis of R-1-phenylethyl acetate
AU - Kirilin, A.
AU - Sahin, S.
AU - Tokareva, A.
AU - Mäki-Arvela, P.
AU - Kordas, K.
AU - Leino, A.-R.
AU - Shchukarev, A.
AU - Mikkola, J.-P.
AU - Kustov, L. M.
AU - Salmi, T.
AU - Murzin, D. Yu
N1 - Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2010/12
Y1 - 2010/12
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=78650798702&partnerID=8YFLogxK
U2 - 10.1134/S0023158410060054
DO - 10.1134/S0023158410060054
M3 - Article
AN - SCOPUS:78650798702
SN - 0023-1584
VL - 51
SP - 809
EP - 815
JO - Kinetics and Catalysis
JF - Kinetics and Catalysis
IS - 6
ER -