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Oxidative Cleavage of Vicinal Diols with the Combination of Platinum and Vanadium Catalysts and Molecular Oxygen
Author(s) -
Obara Naoyuki,
Hirasawa Shota,
Tamura Masazumi,
Nakagawa Yoshinao,
Tomishige Keiichi
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600153
Subject(s) - adipic acid , chemistry , catalysis , vicinal , yield (engineering) , vanadium , turnover number , bond cleavage , medicinal chemistry , cleavage (geology) , oxidative cleavage , organic chemistry , materials science , fracture (geology) , geotechnical engineering , engineering , metallurgy
The combination of Pt/C and V 2 O 5 catalysts gave good performance for the oxidative cleavage of trans ‐1,2‐cyclohexanediol into adipic acid via 2‐hydroxycyclohexanone. The yield of adipic acid reached 90 % in the one‐pot oxidative cleavage of trans ‐1,2‐cyclohexanediol. The yield was higher than that obtained in the oxidation of 2‐hydroxycyclohexanone with V catalyst, and the higher yield was due to the low 2‐hydroxycyclohexanone concentration during the one‐pot oxidation of trans ‐1,2‐cyclohexanediol. Cyclic vicinal diols having a six‐membered ring and linear vicinal diols having two secondary OH groups were converted into dicarboxylic acids and two carboxylic acids, respectively. The activity of the Pt catalyst decreased during the reaction, and the activity was partially restored by treating the used catalyst with H 2 at 573 K. Even without regeneration, the turnover number based on total Pt could reach ≈1000 in a long reaction with an increased amount of trans ‐1,2‐cyclohexanediol.