Comparison of C═C bond hydrogenation in C-4 unsaturated nitriles over Pt/alumina

Akram, H., Monaghan, A. and Jackson, S. D. (2016) Comparison of C═C bond hydrogenation in C-4 unsaturated nitriles over Pt/alumina. Industrial and Engineering Chemistry Research, 55(7), pp. 1843-1848. (doi: 10.1021/acs.iecr.5b04047)

Abstract

The hydrogenation of allyl cyanide (but-1-ene-4-nitrile, AC), trans- and cis-crotononitrile (E- and Z-but-2-ene nitrile, TCN and CCN), and methacrylonitrile (2-cyano-1-propene, MCN) were studied, both singly and competitively, over a Pt/alumina catalyst in the liquid phase. Each unsaturated nitrile only underwent C═C bond hydrogenation: no evidence was found for the formation of the saturated or unsaturated amine. The nonconjugated allyl cyanide was found to be the most reactive unsaturated nitrile. Activation energies for the hydrogenation of the C═C bond in AC and MCN were determined giving values of 64 ± 7 kJ mol–1 for AC and 37 ± 4 kJ mol–1 for MCN. The reaction was zero order for both nitriles. Competitive hydrogenations revealed that not only does allyl cyanide react preferentially over the other isomers but also it inhibits the hydrogenation of the other isomers. When all four nitriles were simultaneously hydrogenated, inhibition effects were easily seen suggesting that in terms of strength of bonding to the surface an order of AC > CCN > TCN ∼ MN can be generated.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Jackson, Professor David and Monaghan, Mr Andrew
• Authors: Akram, H., Monaghan, A., and Jackson, S. D.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Industrial and Engineering Chemistry Research
• Publisher: American Chemical Society
• ISSN: 0888-5885
• Published Online: 16 February 2016
• Copyright Holders: Copyright © 2016 American Chemical Society
• First Published: First published in Industrial and Engineering Chemistry Research 55(7): 1843-1848
• Publisher Policy: Reproduced in accordance with the publisher copyright policy