One-pot chemo-biocatalytic synthesis of R-1-phenylethyl acetate from acetophenone hydrogenation over Pd/Al2O3 catalyst

Päivi Mäki-Arvela; Serap Sahin; Narendra Kumar; Teemu Heikkilä; Vesa-Pekka Lehto; Tapio Salmi; Dmitry Yu. Murzin

doi:10.1016/j.apcata.2008.07.039

One-pot chemo-biocatalytic synthesis of R-1-phenylethyl acetate from acetophenone hydrogenation over Pd/Al₂O₃ catalyst

Päivi Mäki-Arvela, Serap Sahin, Narendra Kumar, Teemu Heikkilä, Vesa-Pekka Lehto, Tapio Salmi, Dmitry Yu. Murzin^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

10 Citations (Scopus)

Abstract

The kinetics in the one-pot synthesis of R-1-phenyl ethylacetate starting from acetophenone have been systematically investigated by using different amounts of hydrogenation catalyst and an immobilized enzyme simultaneously. The kinetic results revealed that there is interference between their catalytic performance indicating that these catalysts were not acting independently but in concert. The reaction mechanism was very complex, since besides the consecutive reactions, hydrogen-acylation, also dehydration of an intermediate product, (R,S)-1-phenylethanol occurred leading to styrene and its instantaneous hydrogenation to ethyl benzene. This work presents the kinetic regularities, quantitative understanding of which remains a challenge.

Original language	English
Pages (from-to)	24-29
Number of pages	6
Journal	Applied Catalysis A: General
Volume	350
Issue number	1
DOIs	https://doi.org/10.1016/j.apcata.2008.07.039
Publication status	Published - 15 Nov 2008
MoE publication type	A1 Journal article-refereed

Funding

This work is part of the activities at the Åbo Akademi Process Chemistry Centre (ÅA-PCC) within the Finnish Centre of Excellence Programme (2000–2011) appointed by the Academy of Finland. The authors are grateful to Prof. Liisa Kanerva from University of Turku from the helpful discussions.

Keywords

Acetophenone
Acylation
Chemo-biocatalysis
Hydrogenation
R-1-phenyl ethylacetate

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Cite this

@article{e6607e67ea7e42ed9a3f516fc90029ba,

title = "One-pot chemo-biocatalytic synthesis of R-1-phenylethyl acetate from acetophenone hydrogenation over Pd/Al2O3 catalyst",

abstract = "The kinetics in the one-pot synthesis of R-1-phenyl ethylacetate starting from acetophenone have been systematically investigated by using different amounts of hydrogenation catalyst and an immobilized enzyme simultaneously. The kinetic results revealed that there is interference between their catalytic performance indicating that these catalysts were not acting independently but in concert. The reaction mechanism was very complex, since besides the consecutive reactions, hydrogen-acylation, also dehydration of an intermediate product, (R,S)-1-phenylethanol occurred leading to styrene and its instantaneous hydrogenation to ethyl benzene. This work presents the kinetic regularities, quantitative understanding of which remains a challenge.",

keywords = "Acetophenone, Acylation, Chemo-biocatalysis, Hydrogenation, R-1-phenyl ethylacetate",

author = "P{\"a}ivi M{\"a}ki-Arvela and Serap Sahin and Narendra Kumar and Teemu Heikkil{\"a} and Vesa-Pekka Lehto and Tapio Salmi and Murzin, \{Dmitry Yu.\}",

note = "Funding Information: This work is part of the activities at the {\AA}bo Akademi Process Chemistry Centre ({\AA}A-PCC) within the Finnish Centre of Excellence Programme (2000–2011) appointed by the Academy of Finland. The authors are grateful to Prof. Liisa Kanerva from University of Turku from the helpful discussions. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2008",

month = nov,

day = "15",

doi = "10.1016/j.apcata.2008.07.039",

language = "English",

volume = "350",

pages = "24--29",

journal = "Applied Catalysis A: General",

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T1 - One-pot chemo-biocatalytic synthesis of R-1-phenylethyl acetate from acetophenone hydrogenation over Pd/Al2O3 catalyst

AU - Mäki-Arvela, Päivi

AU - Sahin, Serap

AU - Kumar, Narendra

AU - Heikkilä, Teemu

AU - Lehto, Vesa-Pekka

AU - Salmi, Tapio

AU - Murzin, Dmitry Yu.

N1 - Funding Information: This work is part of the activities at the Åbo Akademi Process Chemistry Centre (ÅA-PCC) within the Finnish Centre of Excellence Programme (2000–2011) appointed by the Academy of Finland. The authors are grateful to Prof. Liisa Kanerva from University of Turku from the helpful discussions. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2008/11/15

Y1 - 2008/11/15

N2 - The kinetics in the one-pot synthesis of R-1-phenyl ethylacetate starting from acetophenone have been systematically investigated by using different amounts of hydrogenation catalyst and an immobilized enzyme simultaneously. The kinetic results revealed that there is interference between their catalytic performance indicating that these catalysts were not acting independently but in concert. The reaction mechanism was very complex, since besides the consecutive reactions, hydrogen-acylation, also dehydration of an intermediate product, (R,S)-1-phenylethanol occurred leading to styrene and its instantaneous hydrogenation to ethyl benzene. This work presents the kinetic regularities, quantitative understanding of which remains a challenge.

AB - The kinetics in the one-pot synthesis of R-1-phenyl ethylacetate starting from acetophenone have been systematically investigated by using different amounts of hydrogenation catalyst and an immobilized enzyme simultaneously. The kinetic results revealed that there is interference between their catalytic performance indicating that these catalysts were not acting independently but in concert. The reaction mechanism was very complex, since besides the consecutive reactions, hydrogen-acylation, also dehydration of an intermediate product, (R,S)-1-phenylethanol occurred leading to styrene and its instantaneous hydrogenation to ethyl benzene. This work presents the kinetic regularities, quantitative understanding of which remains a challenge.

KW - Acetophenone

KW - Acylation

KW - Chemo-biocatalysis

KW - Hydrogenation

KW - R-1-phenyl ethylacetate

UR - https://www.scopus.com/pages/publications/52949140178

U2 - 10.1016/j.apcata.2008.07.039

DO - 10.1016/j.apcata.2008.07.039

M3 - Article

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SN - 0926-860X

VL - 350

SP - 24

EP - 29

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

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