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Title: Transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst

Abstract

The transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst, leading to the formation of 2-butanone and 2-butanol, was studied in hydrogen and deuterium atmosphere. The effect of hydrogen and deuterium atmosphere. The effect of hydrogen pressure (1.3-100 kPa) and temperature (323-423 K) on the reaction rate was also measured. The transformation of the two stereoisomers involves different mechanisms. In the case of the cis-isomer, hydrogen participates in the cleavage of the C-O bond and different surface species belong to the two products. In the case of the trans-isomer, ring opening by hydrogen (the formation of 2-butanol) is less significant and the main reaction is intramolecular migration leading to the formation of 2-butanone. Considering the geometry of the adsorbed species, cis-2,3-dimethyloxirane is most probably adsorbed on the surface of the Pd catalyst in a planar manner, while the adsorption of the trans-isomer is intermediate between edgewise and planar adsorption model. 18 refs., 3 figs., 3 tabs.

Authors:
; ;  [1]
  1. Attila Univ., Szeged (Hungary)
Publication Date:
OSTI Identifier:
563515
Resource Type:
Journal Article
Journal Name:
Journal of Catalysis
Additional Journal Information:
Journal Volume: 167; Journal Issue: 1; Other Information: PBD: 1 Apr 1997
Country of Publication:
United States
Language:
English
Subject:
40 CHEMISTRY; EPOXIDES; HYDROGENATION; PALLADIUM; CATALYTIC EFFECTS; SILICA; HETEROGENEOUS CATALYSIS; CATALYST SUPPORTS; DEUTERIUM; TEMPERATURE DEPENDENCE; TEMPERATURE RANGE 0273-0400 K; TEMPERATURE RANGE 0400-1000 K

Citation Formats

Fasi, A, Notheisz, F, and Bartok, M. Transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst. United States: N. p., 1997. Web. doi:10.1006/jcat.1997.1543.
Fasi, A, Notheisz, F, & Bartok, M. Transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst. United States. https://doi.org/10.1006/jcat.1997.1543
Fasi, A, Notheisz, F, and Bartok, M. 1997. "Transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst". United States. https://doi.org/10.1006/jcat.1997.1543.
@article{osti_563515,
title = {Transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst},
author = {Fasi, A and Notheisz, F and Bartok, M},
abstractNote = {The transformation of cis- and trans-2,3-dimethyloxiranes on a Pd/SiO{sub 2} catalyst, leading to the formation of 2-butanone and 2-butanol, was studied in hydrogen and deuterium atmosphere. The effect of hydrogen and deuterium atmosphere. The effect of hydrogen pressure (1.3-100 kPa) and temperature (323-423 K) on the reaction rate was also measured. The transformation of the two stereoisomers involves different mechanisms. In the case of the cis-isomer, hydrogen participates in the cleavage of the C-O bond and different surface species belong to the two products. In the case of the trans-isomer, ring opening by hydrogen (the formation of 2-butanol) is less significant and the main reaction is intramolecular migration leading to the formation of 2-butanone. Considering the geometry of the adsorbed species, cis-2,3-dimethyloxirane is most probably adsorbed on the surface of the Pd catalyst in a planar manner, while the adsorption of the trans-isomer is intermediate between edgewise and planar adsorption model. 18 refs., 3 figs., 3 tabs.},
doi = {10.1006/jcat.1997.1543},
url = {https://www.osti.gov/biblio/563515}, journal = {Journal of Catalysis},
number = 1,
volume = 167,
place = {United States},
year = {Tue Apr 01 00:00:00 EST 1997},
month = {Tue Apr 01 00:00:00 EST 1997}
}