Heterogeneous catalysis: The horiuti-polanyi mechanism and alkene hydrogenation

Bruce M. Mattson, Wendy Foster, Jaclyn Greimann, Trisha Hoette, Nhu Le, Anne Mirich, Shanna Wankum, Ann Cabri, Claire Reichenbacher, Erika Schwanke

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The hydrogenation of alkenes by heterogeneous catalysts has been studied for 80 years. The foundational mechanism was proposed by Horiuti and Polanyi in 1934 and consists of three steps: (i) alkene adsorption on the surface of the hydrogenated metal catalyst, (ii) hydrogen migration to the β-carbon of the alkene with formation of a σ-bond between the metal and α-C, and finally (iii) reductive elimination of the free alkane. Hundreds of papers have appeared on the topic, along with a number of variations on the Horiuti-Polanyi mechanism. The second step is highly reversible, leading to extensive deuterium-hydrogen exchange when D2(g) is used. This paper describes the investigation of gas-phase reactions between deuterium and 1-butene using a supported palladium catalyst under ambient laboratory conditions and how the results are consistent with the Horiuti-Polanyi mechanism. An Excel spreadsheet for modeling the extent and distribution of deuteration within butane-d x is described. Interested readers could develop a laboratory or research experience based on results presented here. The results are also suitable for inclusion in an upper-division chemistry course in which organometallic chemistry or reaction mechanisms involving heterogeneous catalysts are discussed. The catalyst tubes are inexpensive and easy to construct. Analysis of the butane produced by 1H NMR and GC-MS leads to numerous conclusions in support of the Horiuti-Polanyi mechanism.

Original languageEnglish
Pages (from-to)613-619
Number of pages7
JournalJournal of Chemical Education
Volume90
Issue number5
DOIs
StatePublished - May 14 2013

Fingerprint

Alkenes
Catalysis
Hydrogenation
chemistry
Catalysts
Deuterium
inclusion
migration
Hydrogen
Metals
Alkanes
Spreadsheets
Palladium
Organometallics
experience
Carbon
Gases
Nuclear magnetic resonance
Adsorption
butane

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Education

Cite this

Mattson, B. M., Foster, W., Greimann, J., Hoette, T., Le, N., Mirich, A., ... Schwanke, E. (2013). Heterogeneous catalysis: The horiuti-polanyi mechanism and alkene hydrogenation. Journal of Chemical Education, 90(5), 613-619. https://doi.org/10.1021/ed300437k

Heterogeneous catalysis : The horiuti-polanyi mechanism and alkene hydrogenation. / Mattson, Bruce M.; Foster, Wendy; Greimann, Jaclyn; Hoette, Trisha; Le, Nhu; Mirich, Anne; Wankum, Shanna; Cabri, Ann; Reichenbacher, Claire; Schwanke, Erika.

In: Journal of Chemical Education, Vol. 90, No. 5, 14.05.2013, p. 613-619.

Research output: Contribution to journalArticle

Mattson, BM, Foster, W, Greimann, J, Hoette, T, Le, N, Mirich, A, Wankum, S, Cabri, A, Reichenbacher, C & Schwanke, E 2013, 'Heterogeneous catalysis: The horiuti-polanyi mechanism and alkene hydrogenation', Journal of Chemical Education, vol. 90, no. 5, pp. 613-619. https://doi.org/10.1021/ed300437k
Mattson, Bruce M. ; Foster, Wendy ; Greimann, Jaclyn ; Hoette, Trisha ; Le, Nhu ; Mirich, Anne ; Wankum, Shanna ; Cabri, Ann ; Reichenbacher, Claire ; Schwanke, Erika. / Heterogeneous catalysis : The horiuti-polanyi mechanism and alkene hydrogenation. In: Journal of Chemical Education. 2013 ; Vol. 90, No. 5. pp. 613-619.
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