Synthesis of 2-Nitro-4-methylsulfonylbenzoic Acid

Chunsheng Cheng; Zhenyun Wei; Xiaohua Ma

doi:10.14233/ajchem.2015.18833

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Issue Published : June 22, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of 2-Nitro-4-methylsulfonylbenzoic Acid

https://doi.org/10.14233/ajchem.2015.18833

Chunsheng Cheng

Technical Development Department, Shenyang Sciencreat Chemicals Co. Ltd., Shenyang, Liaoning, P.R. China

Zhenyun Wei

Technical Development Department, Shenyang Sciencreat Chemicals Co. Ltd., Shenyang, Liaoning, P.R. China

Xiaohua Ma

Technical Development Department, Shenyang Sciencreat Chemicals Co. Ltd., Shenyang, Liaoning, P.R. China

Corresponding Author(s) : Chunsheng Cheng

chengchunsheng@sinochem.com; tomorrow88166@163.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10
Article Published : June 22, 2015

Abstract

2-Nitro-4-methylsulfonylbenzoic acid was synthesized by the oxidation of 2-nitro-4-methylsulfonyl toluene with hydrogen peroxide in the presence of CuO/Al₂O₃, which was first used in strong acid system. Furthermore, the process of the reaction was thoroughly investigated by varying reactant molar ratio, reaction temperature and the amount of catalyst to obtain the optimum process. Meanwhile, unreacted 2-nitro-4-methylsulfonyl toluene can be recycled after simple treatment. The yield can reach 78.3 %. The method demonstrated the following advantages. Firstly, the oxidant dosage of sulfuric acid and hydrogen peroxide will be reduced greatly. Secondly, unreacted 2-nitro-4-methylsulfonyl toluene can be recycled. Thirdly, this process had good performance on safety. It will be a high-efficiency, energy-saving and environment-friendly technology to produce 2-nitro-4-methylsulfonylbenzoic acid.

Keywords

2-Nitro-4-methylsulfonylbenzoic acid CuO/Al2O3 catalyst Hydrogen peroxide Yield

Cheng, C., Wei, Z., & Ma, X. (2015). Synthesis of 2-Nitro-4-methylsulfonylbenzoic Acid. Asian Journal of Chemistry, 27(10), 3559–3563. https://doi.org/10.14233/ajchem.2015.18833

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References

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R.W. Brown, Preparation of 2-(Chloro, bromo or nitro)-4-(alkyl-sulfonyl)benzoic acids and Intermediates, Patent WO9006301 A1 (1990).
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G. Sheng, Y. Fumin and Z. Lin, Agrochemicals, 40, 20 (2001).
P.K. Wehrenberg, Method for preparation of Herbicide Intermediates, US Patent 5648525 (1997).
S. Patai, The Chemistry of Carboxylic Acids and Esters, J. Wiley & Sons, New York (1969).
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W.J. Michaely and G.W. Kraatz, Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as Herbicides, US Patent 4780127 (1988).
P.G. Legras, Process for the Preparation of 2-Nitro substituted benzoic acids, Patent WO2007099450 (2007).
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J.Y. Wu and H.L. Wang, The Synthesis of Adjacent Nitro of Thiamphenicol benzoic acid, Chinese Patent CN101503383 (2009).
P.G. Legras, Process for the Preparation of 2-Nitro substituted benzoic acids, Patent WO2007099450 (2007).
V. Kavitha and K. Palanivelu, Chemosphere, 55, 1235 (2004); doi:10.1016/j.chemosphere.2003.12.022.
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References

K. Evans, M. Cichy-Knight, F.T. Coppo, K.A. Dwornik, J.P. Gale, D.M. Garrido, Y.H. Li, M.P. Patel, F.X. Tavares, S.A. Thomson, S.H. Dickerson, A.J. Peat, S.M. Sparks, P. Banker and J.P. Cooper, Glycogen Phosphorylase Inhibitor Compounds and Pharmaceutical Compositions Thereof, Patent WO2006052722 (2006).

D.A. Jackson, A. Edmunds, M.C. Bowden and B. Brockbank, Process for the Production of Cyclic Ditketones, Patent WO2005105745 (2005).

R. Beaudegnies, A. Edmunds, C. Luethy, J. Schaetzer and S. Wendeborn, Substituted Bicylooctenes and their Use as Herbicides, Patent WO2005123667 (2005).

P.W. Wojtkowski, Method for Acylating Cyclic Compounds, US Patent 20030232984 (2003).

P.W. Wojtkowski, Method for Acylating Cyclic Compounds, US Patent 20020049317 (2002).

S.M. Brown, T.W. Bentley and R.O. Jones, Process for the Preparation of Acylated Cyclic 1,3-Dicarbonyl Compounds, Patent WO9928282A1 (1999).

J.L. Bonnet, F. Bonnemoy, M. Dusser and J. Bohatier, Arch. Environ. Contam. Toxicol., 55, 576 (2008); doi:10.1007/s00244-008-9145-2.

L. Katz, L.S. Karger, W. Schroeder and M.S. Cohen, J. Org. Chem., 18, 1380 (1953); doi:10.1021/jo50016a019.

R.A. Wichert, J.K. Townson, D.W. Bartlett and G.A. Foxon, Technical Review of Mesotrione, A New Maize Herbicide, The 1999 Brighton Conference-Weeds, pp. 105-110 (1999).

R.C. Le Roquesn and M. Peyronneau, Use of Gallium Salts as Lewis acid-Type Catalysts and Sulfonylation Composition Comprising these Salts, Patent 2827194 (2003).

B.M. Choudary, N.S. Chowdari and M.L. Kantam, J. Chem. Soc. Perkin Trans. I, 2689 (2000); doi:10.1039/B002931I.

Egami and T. Katsuki, J. Am. Chem. Soc., 129, 8940 (2007); doi:10.1021/ja071916+.

M. Carraro, L. Sandei, A. Sartorel, G. Scorrano and M. Bonchio, Org. Lett., 8, 3671 (2006); doi:10.1021/ol061197o.

K. Bahrami, Tetrahedron Lett., 47, 2009 (2006); doi:10.1016/j.tetlet.2006.01.051.

M.G. Voronkov, E.N. Deryagina and E.N. Sukhomazova, Zh. Org. Khim., 22, 846 (1986).

H. Hagen, Preparation of Methylsulfonylbenzoic acids, US Patent 5424481 (1995).

R.W. Brown, Preparation of 2-(Chloro, bromo or nitro)-4-(alkyl-sulfonyl)benzoic acids and Intermediates, Patent WO9006301 A1 (1990).

R.W. Brown, J. Org. Chem., 56, 4974 (1991); doi:10.1021/jo00016a032.

G. Sheng, Y. Fumin and Z. Lin, Agrochemicals, 40, 20 (2001).

P.K. Wehrenberg, Method for preparation of Herbicide Intermediates, US Patent 5648525 (1997).

S. Patai, The Chemistry of Carboxylic Acids and Esters, J. Wiley & Sons, New York (1969).

C.A. Buehler and D.F. Perason, Survey of Organic Synthesis, J. Wiley & Sons (1970).

W.J. Michaely and G.W. Kraatz, Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as Herbicides, US Patent 4780127 (1988).

P.G. Legras, Process for the Preparation of 2-Nitro substituted benzoic acids, Patent WO2007099450 (2007).

W. Jary, M. Lassnig and P. Poechlauer, Oxidation Method for Producing Optionally Substituted Benzoic Acids from the Corresponding Toluenes, Patent WO2004058698A1 (2004).

J.Y. Wu and H.L. Wang, The Synthesis of Adjacent Nitro of Thiamphenicol benzoic acid, Chinese Patent CN101503383 (2009).

P.G. Legras, Process for the Preparation of 2-Nitro substituted benzoic acids, Patent WO2007099450 (2007).

V. Kavitha and K. Palanivelu, Chemosphere, 55, 1235 (2004); doi:10.1016/j.chemosphere.2003.12.022.

S.H. Bossmann, E. Oliveros, S. Göb, S. Siegwart, E.P. Dahlen, L. Payawan, M. Straub, M. Wörner and A.M. Braun, Phys. Chem. A, 102, 5542 (1998); doi:10.1021/jp980129j.

R. Chen and J.J. Pignatello, Environ. Sci. Technol., 31, 2399 (1997); doi:10.1021/es9610646.

C.S. Cheng, Z.Y. Wei and P. Yu, The Synthesis of 2-Nitro-4-methylsulfonylbenzoic acid, Chinese Patent CN102584650 (2014).

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Synthesis of 2-Nitro-4-methylsulfonylbenzoic Acid

Corresponding Author(s) : Chunsheng Cheng

Abstract

Keywords

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