Carbon-carbon double bonds can be catalytically hydrogenated on hydrated alumina

Article abstract of DOI:10.1063/1.441546

We use inelastic electron tunneling spectroscopy to study catalytically induced hydrogenation of several unsaturated dicarboxylates chemisorbed on undried, hydrated alumina.Using isotope substitution we establish that hydroxyl groups on the alumina are the source of hydrogen.Fumarate and maleate hydrogenate completely at room temperature forming a succinate species.Gutaconate, hydromuconate, and muconate hydrogenate in a way that is exponentially temperature dependent, only slightly pressure dependent, and time independent in the range of a few minutes to an hour.Wehave investigated the temperature dependence over the range 25-400 deg C, and we believe it is related to the thermal dehydration mechanism in alumina.From the variation in temperature dependence among the surface species we develop an index of the relative ease of hydrogenation that correlates well with double bond distance from the surface and with bond resonance stabilization.Species whose double bonds are constrained to be closer to the surface hydrogenate more easily, and conjugated double bonds stabilize a species against hydrogenation.The alumina surface can be regenerated with water vapor and used for further hydrogenation.

Full text of DOI:10.1063/1.441546

Carbon–carbon double bonds can be catalytically hydrogenated on hydrated alumina
James T. Hall and Duncan E. McBride
Citation: The Journal of Chemical Physics 74, 4164 (1981); doi: 10.1063/1.441546
View online: http://dx.doi.org/10.1063/1.441546
View Table of Contents: http://scitation.aip.org/content/aip/journal/jcp/74/7?ver=pdfcov
Published by the AIP Publishing
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This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
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This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08

This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08

This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08

This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08

This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08

This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP:
84.120.188.133 On: Tue, 06 May 2014 07:19:08