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Research of Professor Masahito Kodera (Faculty of Science and Engineering) et al. Published in Angewandte Chemie International Edition

Updated Jun. 22, 2017
The research group of Professor Kodera succeeded in selective phenol synthesis by direct oxidation of benzene with hydrogen peroxide as an oxidant using dinuclear copper complex as a catalyst originally developed in their laboratory. In this reaction, the catalyst rotation speed per hour was 1,010 times and exceeded 12,000 after 40 hours, with the benzene conversion rate at more than 22 percent and phenol selectivity at more than 95 percent. Phenol is an important raw material used in house building, as well as for making casting molds for car engine components and electronic parts, fire protection panels, thermal insulation materials, and medicines and pesticides. Its annual domestic production is over one million tons. The conventional industrial manufacturing method of phenol is the Cumene Process, in which phenol is produced from benzene in three stages via the production of cumene hydroperoxide. As cumene hydroperoxide is an explosive intermediate, its concentration must be kept low. As a result, the amount of phenol produced is only about 5 percent of the amount of benzene used. In addition, the three reaction steps have a high environmental impact, such as low energetic efficiency, using concentrated sulfuric acid as the catalyst, and create an undesirable by-product. In the past fifty years, however, there has been no better catalyst in the phenol synthesis by direct oxidation of benzene using molecular oxygen as an oxidizing agent that has achieved a benzene conversion rate greater than 22 percent and phenol selectivity greater than 50 percent.
Therefore, it is a major goal for those working in the chemical industry to develop an effective production method of phenol by direct oxidation of benzene. The research group is continuing its efforts to achieve a breakthrough in the development of phenol synthesis with high efficiency and selectivity.

This research project has been supported and funded by JST (Japan Science and Technology Agency) Strategic Basic Research Programs, ‘CREST’ (Core Research for Evolutionary Science and Technology): ‘Development of bio-inspired binuclear metal for methane oxidation catalyst’ (2016-2021, representative: Masahito Kodera)

Published in:
‘Angewandte Chemie International Edition’ (DOI:10.1002/anie.201702291)

Title of Article: ‘Specific Enhancement of Catalytic Activity by a Dicopper Core:
Selective Hydroxylation of Benzene to Phenol with Hydrogen Peroxide’

Authors:
Tomokazu Tsuji (third year, Doctoral Program in Applied Chemistry, Graduate
School of Science and Engineering)
Antonius Andre Zaoputra (second year, Master’s Program in Applied Chemistry,
Graduate School of Science and Engineering)
Yutaka Hitomi (Professor, Faculty of Science and Engineering)
Kaoru Mieda (Researcher, School of Science, University of Hyogo)
Takashi Ogura (Professor, School of Science, University of Hyogo)
Yoshihito Shiota (Associate Professor, Institute for Materials Chemistry and
Engineering, Kyushu University)
Kazunari Yoshizawa (Professor, Institute for Materials Chemistry and Engineering,
Kyushu University)
Hiroyasu Sato (Chief Researcher, Center for Applied Technology, Rigaku Corporation)
Masahito Kodera (Professor, Faculty of Science and Engineering)
.