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The N-Hydroxyphthalimide Catalyzed Oxidation of Cyclohexene to Cyclohexenyl Hydroperoxide: Reasons for Deactivation and Stability of the Catalyst Full article

Общее Language: Английский, Genre: Full article,
Status: Published, Source type: Original
Journal Catalysis Communications
ISSN: 1566-7367 , E-ISSN: 1873-3905
Output data Year: 2018, Volume: 114, Pages: 84-88 Pages count : 5 DOI: 10.1016/j.catcom.2018.06.010
Tags Oxidation N-Hydroxyphthalimide Cyclohexene Oxygen Hydroperoxide
Authors Kuznetsova N.I. 1 , Kuznetsova L.I. 1 , Yakovina O.A. 1 , Babushkin D.E. 1 , Bal'zhinimaev B.S. 1
Affiliations
1 Boreskov Institute of Catalysis SB RAS, Russia

Funding (1)

1 Ministry of Science and Higher Education of the Russian Federation ГЗ-2017-2020

Abstract: Selective oxidation of cyclohexene to cyclohexenyl hydroperoxide catalyzed by N-hydroxyphthalimide (NHPI) was studied. Kinetic observations and 13C and 1H NMR spectroscopy showed that accumulation of cyclohexenyl hydroperoxide was accompanied by deactivation of the catalyst. A mechanism of the deactivation through phthalimido N-oxyl radical (PINO) addition to vinyl position of olefin was suggested. Responsible for the deactivation, PINO-C6H10-OOH hydroperoxide adducts were detected in the reaction conditions, and their molecular structure was elucidated by DFT technique. The mechanism explained an unexpected experimental effect, that is, lowering the oxygen partial pressure improved the stability of NHPI without decrease in production of cyclohexenyl hydroperoxide.
Cite: Kuznetsova N.I. , Kuznetsova L.I. , Yakovina O.A. , Babushkin D.E. , Bal'zhinimaev B.S.
The N-Hydroxyphthalimide Catalyzed Oxidation of Cyclohexene to Cyclohexenyl Hydroperoxide: Reasons for Deactivation and Stability of the Catalyst
Catalysis Communications. 2018. V.114. P.84-88. DOI: 10.1016/j.catcom.2018.06.010 publication_identifier_short.wos_identifier_type publication_identifier_short.scopus_identifier_type publication_identifier_short.rinz_identifier_type
Dates:
Submitted: Apr 12, 2018
Accepted: Jun 13, 2018
Published online: Jun 15, 2018
Published print: Aug 1, 2018
Identifiers:
publication_identifier.wos_identifier_type WOS:000440771300019
publication_identifier.scopus_identifier_type 2-s2.0-85048853573
publication_identifier.rinz_identifier_type 35750035
publication_identifier.accession_number_identifier_type 2018:1199916
publication_identifier.chemical_accession_number_identifier_type 169:178113
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