An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
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Shiyu Tan
,
Yang Yang
Abstract
p-Aminobenzene sulfonamide (sulfanilamide, SN) is the simplest and most-used sulfonamide medicine. The key step of SN production via the commonly used chlorosulfonic acid routine is the synthesis of p-acetaminobenzenesulfonyl chloride (P-ASC). A large amount of HSO3Cl has to be used in the traditional process, which results in serious environmental problems. In this study, an alternative chlorosulfonic acid process to synthesize P-ASC was investigated by partially substituting HSO3Cl by PCl5 as the chlorination agent. Compared with the traditional process, the molar ratio of HSO3Cl to acetanilide (the main raw material) can be decreased from 4.96 to 2.1 using CCl4 as the diluent; also, addition of a small amount of NH4Cl was found to significantly increase the P-ASC yield. Operating conditions of the reaction were studied first by single-factor experiments and later by orthogonal experiments to obtain optimum operating conditions under which the P-ASC yield can reach as high as 86.3 %.
[1] Boekman, F., Bohman, O., & Siegbahn, H. O. G. (1992). ESCA studies of phase transfer catalysts in solution. 2. Surface ion pairing and salting-out effects. The Journal of Physical Chemistry, 96, 2278–2283. DOI: 10.1021/j100184a047. http://dx.doi.org/10.1021/j100184a04710.1021/j100184a047Suche in Google Scholar
[2] Castaner, J., Riera, J., Carilla=., J., Robert, A, Molins, E., & Miravitlles, C. (1991). A new trifluoromethylating agent: synthesis of polychlorinated (trifluoromethyl)benzenes and 1,3-bis(trifluoromethyl)benzenes and conversion into their trichloromethyl counterparts and molecular structure of highly strained polychloro-m-xylenes. The Journal of the Organic Chemistry, 56, 103–110. DOI: 10.1021/jo00001a022. http://dx.doi.org/10.1021/jo00001a02210.1021/jo00001a022Suche in Google Scholar
[3] Emerson, D. W., & Ifalade, S. O. (2005). Improved preparation of macroporous, chlorosulfonated poly(styrene-codivinylbenzene) and conversion to sulfonamides and sulfonylhydrazines. Industrial & Engineering Chemistry Research, 44, 7045–7048. DOI: 10.1021/ie050371u. http://dx.doi.org/10.1021/ie050371u10.1021/ie050371uSuche in Google Scholar
[4] Fan, X., Wang, J. G., & Wang, J. P. (2005). Optimum semimicro synthesis of P-aminobenzene sulfonamide. Journal of Luoyang Normal Univiversity, 2, 133–135. Suche in Google Scholar
[5] Fidock, D. A., Rosenthal, P. J., Croft, S. L., Brun, R., & Nwaka, S. (2004). Antimalarial drug discovery: efficacy models for compound screening. Nature Reviews Drug Discovery, 3, 509–520. DOI: 10.1038/nrd1416. http://dx.doi.org/10.1038/nrd141610.1038/nrd1416Suche in Google Scholar
[6] Galat, A. (1944). New processes for sulfanilamide. Industrial & Engineering Chemistry, 36, 192. DOI: 10.1021/ie50410a023. http://dx.doi.org/10.1021/ie50410a02310.1021/ie50410a023Suche in Google Scholar
[7] Gao, F., Wang, Y., & Zeng, Y. (2002). New process study on sulfanilamide synthesis by chlorobenzene. Chemical Production and Technology, 9, 4–6. Suche in Google Scholar
[8] Huang, Z., Lin, Z., & Huang, J. (2001). A novel kind of antitumour drugs using sulfonamide as parent compound. European Journal of Medicinal Chemistry, 36, 863–872. DOI: 10.1016/S0223-5234(01)80002-7. http://dx.doi.org/10.1016/S0223-5234(01)01285-510.1016/S0223-5234(01)80002-7Suche in Google Scholar
[9] Kealey, D., & Haines, P. J. (2002). BIOS instant notes in analytical chemistry. New York, NY, USA: Taylor & Francis. 10.4324/9780203645444Suche in Google Scholar
[10] Kong, X., Teng, Y., & Zhang, T. (1998). Synthesis of pacetamidobenzene sulfone chloride. Journal of Shenyang Institute of Chemical Technology, 12, 117–121. Suche in Google Scholar
[11] Li, G., Liu, J., & Li, J. (2007). Improved synthetic technology for the organic dye intermediate: p-acetamidobenzene sulfonyl chloride. Journal of Henan Normal University (Natural Science), 35, 182–184. Suche in Google Scholar
[12] Li, P. (2002). Treatment of waste acid in chlorosulfonic acid production process. Chemical Intermediates, 17, 15–16. Suche in Google Scholar
[13] Li, Y., & Hu, C. (2005). Experimental design and data analysis. Beijing, China: Chemical Industry Press. Suche in Google Scholar
[14] Lin, X., Wei, R.-Q., Liu, X.-N., & Zhou, R. (2009). Study on the function group uniformity of polystyrol sulfonyl chloride resins by infrared spectra. Spectroscopy and Spectral Analysis, 29, 1801–1804. DOI: 10.3964/j.issn.1000-0593(2009)07-1801-04. Suche in Google Scholar
[15] Martin, H., Gysin, H., Neracher, O., & Hirt, R. (1943). U.S. Patent No. 243,5974. Washington, D.C.: U.S. Patent and Trademark Office. Suche in Google Scholar
[16] Martin. H., & Hirt, R. (1947). U.S. Patent No. 242,9207. Washington, D.C.: U.S. Patent and Trademark Office. Suche in Google Scholar
[17] Meier, M., & Tronich, W. (1992). U.S. Patent No. 513,6043. Washington, D.C.: U.S. Patent and Trademark Office. Suche in Google Scholar
[18] Meng, G. (1995). Improvement for the synthesis and purification of p-acetate-amino-benzene-sulfonyl chloride. Jounal of Henan Normal University (Medical Science), 14, 179–180. Suche in Google Scholar
[19] Montgomery, D. C. (2004). Design and analysis of experiments (6th Ed.). New York, NY, USA: Wiley. Suche in Google Scholar
[20] Moore, R. M., Jr. (2003). A convenient synthesis of high-purity 1-chloro-2,6-difluorobenzene. Organic Process Research & Development, 7, 921–924. DOI: 10.1021/op0340816. http://dx.doi.org/10.1021/op034081610.1021/op0340816Suche in Google Scholar
[21] Pence, L. H., & Winter, H. C. (1939). Purification of pacetaminobenzenesulfonyl chloride. Journal of the American Chemical Society, 61, 2977–2978. DOI: 10.1021/ja01265a509. http://dx.doi.org/10.1021/ja01265a50910.1021/ja01265a509Suche in Google Scholar
[22] Pouchert, C. J. (1970). The Aldrich library of infrared spectra. Milwaukee, WI, USA: Aldrich Chemical Co Inc. Suche in Google Scholar
[23] Smiles, S., & Stewart, J. (1925). p-Acetaminobenzenesulfonyl chloride. Organic Syntheses, 5, 1. Suche in Google Scholar
[24] Song, B. (1990). New process for acetanilide chlorosulfonation. Tianjin Chemical Industry, 2, 24–29. Suche in Google Scholar
[25] Su, Y., & Hao, Y. (2005). Improved technology for synthesis of p-acetylsulfanilamide. Journal Hebei Normal University (Natural Science Edition), 29, 58–60. Suche in Google Scholar
[26] Su, Y., & Yang, J. (2002). Improved technology for synthesis of p-acetamidobenzenesulfonyl chloride. Journal Hebei Normal University (Natural Science Edition), 26, 162–164. Suche in Google Scholar
[27] Xin, J.-F., Ma, J.-H., Zhang, S.-F., Chen, S.-R., & Li, H.-Y. (2006). Review of the methods of preparing acyl chlorides. Hebei Chemical Engineering Industry, 29, 16–18. Suche in Google Scholar
[28] Zeng, Z. (1981). Organic chemical experiments. Beijing, China: People’s Education Press. Suche in Google Scholar
[29] Zhang, S. (1991). Handbook of fine organic chemical technology. Beijing, China: Science Press. Suche in Google Scholar
[30] Zhao, Z., Wolkenberg, S. E., Lu, M., Munshi, V., Moyer, G., Feng, M., Carella, A. V., Ecto, L. T., Gabryelski, L. J., Lai, M.-T., Prasad, S. G., Yan, Y., McGaughey, G. B., Miller, M. D., Lindsley, C. W., Hartman, G. D., Vacca, J. P., & Williams, T. M. (2008). Novel indole-3-sulfonamides as potent HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs). Bioorganic & Medicinal Chemistry Letters, 18, 554–559. DOI: 10.1016/j.bmcl.2007.11.085. http://dx.doi.org/10.1016/j.bmcl.2007.11.08510.1016/j.bmcl.2007.11.085Suche in Google Scholar PubMed
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- Determination of curcuminoids in substances and dosage forms by cyclodextrin-mediated capillary electrophoresis with diode array detection
- Interaction of Moringa oleifera seed lectin with humic acid
- Hybrid process scheme for the synthesis of ethyl lactate: conceptual design and analysis
- Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
- Denitrification of simulated nitrate-rich wastewater using sulfamic acid and zinc scrap
- Anaerobic treatment of biodiesel by-products in a pilot scale reactor
- Preparation of magnesium hydroxide from nitrate aqueous solution
- Impact of the type of anodic film formed and deposition time on the characteristics of porous anodic aluminium oxide films containing Ni metal
- Synthesis and crystal and molecular structures of N,N′-methylenedipyridinium tetrachlorozincate(II) and N,N′-methylenedipyridinium tetrachlorocadmate(II)
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