Selective Oxidation of Alcohols Catalyzed by a Transition Metal-Free System of NHPI/DDQ/NaNO2

doi:10.3724/SP.J.1088.2010.00734

Chinese Journal of Catalysis ›› 2011, Vol. 32 ›› Issue (1): 118-122.DOI: 10.3724/SP.J.1088.2010.00734

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Selective Oxidation of Alcohols Catalyzed by a Transition Metal-Free System of NHPI/DDQ/NaNO₂

ZHOU Lipeng1, ZHANG Chaofeng1, FANG Tao1, ZHANG Bingbing1, WANG Ying1, YANG Xiaomei1,*, ZHANG Wei2, XU Jie2

1Department of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China; 2State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2010-07-30 Revised:2010-09-19 Online:2011-01-13 Published:2014-05-22

Abstract

Abstract: A transition metal?free catalyst composed of N-hydroxyphthalimide (NHPI), 2,3-dichloro-5,6-dicyano-benzoquinone (DDQ), and NaNO₂ was studied for the selective oxidation of alcohols using O₂ as oxidant. The reaction results showed that this catalyst system can effectively catalyze the oxidation of alcohols to the corresponding aldehydes or ketones. 99% selectivity for benzaldehyde at 65% conversion of benzyl alcohol was obtained at 80 °C for 6 h. In the process of reaction, DDQ abstracted a hydrogen atom from NHPI to generate a highly reactive PINO free radical and hydroquinone. Then, PINO abstracted a hydrogen atom from alcohols to generate aldehydes or ketones. Finally, NO from NaNO₂ decomposition in the reaction media catalyzed the oxidation of hydroquinone to quinone by O₂.

Key words: N-hydroxyphthalimide, 2,3-dichloro-5,6-dicyano benzoquinone, sodium nitrite, selective oxidation, oxygen, alcohol

ZHOU Lipeng1, ZHANG Chaofeng1, FANG Tao1, ZHANG Bingbing1, WANG Ying1, YANG Xiaomei1,*, ZHANG Wei2, XU Jie2. Selective Oxidation of Alcohols Catalyzed by a Transition Metal-Free System of NHPI/DDQ/NaNO₂[J]. Chinese Journal of Catalysis, 2011, 32(1): 118-122.

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Selective Oxidation of Alcohols Catalyzed by a Transition Metal-Free System of NHPI/DDQ/NaNO₂

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