A highly efficient transformation from cumene to cumyl hydroperoxide via catalytic aerobic oxidation at room temperature and investigations into solvent effects, reaction networks and mechanisms

异丙苯 过氧化氢异丙苯 化学 催化作用 激进的 丙酮 选择性 溶剂 光化学 有机化学
作者
Qiuting Lu,Gaoquan Shi,Hongyu Zhou,Enxian Yuan,Chong Chen,Lijun Ji
出处
期刊:Applied Catalysis A-general [Elsevier]
卷期号:630: 118441-118441 被引量:15
标识
DOI:10.1016/j.apcata.2021.118441
摘要

Cumyl hydroperoxide (CHP) is an important intermediate for the production of phenol/acetone, but suffers from severe reaction conditions and a low yield industrially. Here, an efficient transformation from cumene to CHP was developed. Different solvents were modulated for cumene oxidation catalyzed by NHPI/Co, and reaction network and mechanisms were investigated methodically. Hexafluoroisopropanol (HFIP) markedly promoted the transformation from cumene to CHP compared to other solvents at room temperature. A cumene conversion high up to 64.3% were observed with a selectivity to CHP of 71.7%. The solvent HFIP exhibited a significant promotion on cumene oxidation due to its contribution to the enhancement of the concentration of PINO radicals. Moreover, cumyl, cumyl oxyl and methyl radicals were captured by TEMPO and analyzed by HRMS, and the reaction paths and mechanisms from cumene to products were inferred. The preparation method discovered in this work may open an access to the production of CHP.
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