Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition Full article
| Journal |
ACS Catalysis
ISSN: 2155-5435 |
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| Output data | Year: 2014, Volume: 4, Number: 6, Pages: 2022-2028 Pages count : 7 DOI: 10.1021/cs500426a | ||||||
| Tags | heterogeneous hydrogenation, pairwise hydrogen addition, parahydrogen-induced polarization (PHIP), reaction mechanism, α,β-unsaturated carbonyl compounds | ||||||
| Authors |
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| Affiliations |
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Funding (7)
| 1 | Russian Foundation for Basic Research | 12-03-00403 |
| 2 | Russian Foundation for Basic Research | 14-03-00374 |
| 3 | Russian Foundation for Basic Research | 14-03-31239 (01201450183) |
| 4 | Президиум РАН | 5.1.1 |
| 5 | Council for Grants of the President of the Russian Federation | МК-4391.2013.3 |
| 6 | Siberian Branch of the Russian Academy of Sciences | 60 |
| 7 | Siberian Branch of the Russian Academy of Sciences | 61 |
Abstract:
Heterogeneous hydrogenation of α,β-unsaturated carbonyl compounds was addressed using the parahydrogen-induced polarization (PHIP) technique. PHIP effects were observed in hydrogenation of C═C bond of acrolein and crotonaldehyde over different supported metal catalysts, demonstrating the existence of a pairwise route of hydrogen addition to the substrate. Hydrogenation of acrolein over Pd–Sn/Al2O3, Pd–Sn/TiO2, Pd–Zn/TiO2, and Pd/TiO2 catalysts with parahydrogen also led to the polarization of the proton of CHO group of propanal. This was explained by C(O)–H bond dissociation which represents a side process on the catalyst surface. Formation of polarized cis- and trans-2-butenes was detected in hydrogenation of acrolein with parahydrogen over several Rh-based catalysts. This observation is made possible only due to the high NMR signal enhancement provided by PHIP. It was also found that hydrogenation of acetone and propanal with parahydrogen leads to polarized propane formation as a result of C–O bond hydrogenolysis.
Cite:
Salnikov O.G.
, Kovtunov K.V.
, Barskiy D.A.
, Khudorozhkov A.K.
, Inozemtseva E.A.
, Prosvirin I.P.
, Bukhtiyarov V.I.
, Koptyug I.V.
Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition
ACS Catalysis. 2014. V.4. N6. P.2022-2028. DOI: 10.1021/cs500426a WOS Scopus РИНЦ ANCAN OpenAlex
Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition
ACS Catalysis. 2014. V.4. N6. P.2022-2028. DOI: 10.1021/cs500426a WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Mar 31, 2014 |
| Accepted: | May 13, 2014 |
| Published online: | May 21, 2014 |
| Published print: | Jun 6, 2014 |
Identifiers:
| Web of science: | WOS:000337074700043 |
| Scopus: | 2-s2.0-84902197018 |
| Elibrary: | 24054751 |
| Chemical Abstracts: | 2014:802281 |
| Chemical Abstracts (print): | 160:708263 |
| OpenAlex: | W2313630911 |