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The Cu(I)- and HNO3-catalyzed oxidation of substituted toluenes to the benzoic acid based on NO x recycling

Mengyi Wei, Chao Qian, and Xinzhi Chen

Zhejiang University, Zhejiang, China

 

E-mail: qianchao@zju.edu.cn

Abstract: Based on the recycling of NO x , the Cu(I)- and HNO3-catalyzed oxidation of 2-chloro-4-(methylsulfonyl)toluene to 2-chloro-4-(methylsulfonyl)benzoic acid has been developed with an excellent yield of 84.2% and a purity of 99.7%. The optimized reaction conditions (160 °C, oxygen pressure 1.5 MPa, HNO3 concentration 25 wt%, HNO3: substrate 0.5:1) use 1.0 mol% CuI as catalyst. The dosage of HNO3 in the new process is only 25% of the stoichiometric amount and 12.5% of the amount of the traditional process. The NO x emission is 5% amount of the traditional process. The oxidation of several additional toluene derivatives with comparable yields demonstrates the generality to these reaction conditions.

Keywords: HNO3-catalyzed oxidation ; NOx recycling ; Benzylic oxidation ; 2-Chloro-4-(methylsulfonyl)benzoic acid 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0256-y

 

Chemical Papers 72 (1) 51–56 (2018)

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