Journal of Chemical Sciences

, Volume 129, Issue 10, pp 1587–1594 | Cite as

Iron(II) and copper(II) phthalocyanine-catalyzed synthesis of 2-nitro-4-methylsulfonylbenzoic acid under mild conditions

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Abstract

Abstract

A novel method was developed to produce 2-nitro-4-methylsulfonylbenzoic acid (NMSBA) from the oxidation of 2-nitro-4-methylsulfonyltoluene (NMST) by oxygen catalyzed by iron(II) phthalocyanine (FePc) and copper(II) phthalocyanine (CuPc). The order of activity for oxidation of NMST was found to be: FePc > CuPc. Meanwhile, major reaction parameters such as concentrations of catalyst and NaOH, reaction temperature and oxygen pressure have been investigated. Through optimization of the reaction parameters, the highest yield of NMSBA and conversion of NMST (up to 53%, 89.3%, respectively) were achieved with oxygen (2.0 MPa), FePc (\(1.0\times 10^{-4}\,\hbox {mol } \hbox {L}^{-1}\)), NaOH (\(0.6\,\hbox {mol } \hbox {L}^{-1}\)), in methanol at 55\(^{\circ }\hbox {C}\) for 8 h. A plausible mechanism for this catalytic process is proposed which involved deprotonation and radical pathways.

Graphical Abstract

A novel method to produce 2-nitro-4-methylsulfonylbenzoic acid (NMSBA) from the oxidation of 2-nitro-4-methylsulfonyltoluene (NMST) by oxygen catalyzed by iron(II) phthalocyanine (FePc) and copper(II) phthalocyanine (CuPc) has been developed. The reaction parameters and mechanism were studied. The catalytic system will be readily applicable to large-scale production of NMSBA.

Keywords

2-Nitro-4-methylsulfonyltoluene 2-nitro-4-methylsulfonylbenzoic acid aero oxidation metal phthalocyanines 

Notes

Acknowledgements

We greatly acknowledge the financial support in part by the National Key Research and Development Program of China (2016YFB0301703), National Natural Science Foundation of China (21602106), Natural Science Foundation of Jiangsu Province-Outstanding Youth Foundation (BK20170104) and Industry-Academy-Research Prospective Joint Project of Jiangsu Province (BY2016005-06).

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Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  1. 1.Department of Applied Chemistry, College of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjingChina

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