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Sulfonyl chlorination of sulfonate-containing
naphthol azo compounds
- CUI Zhihua1, YANG Jinzong2, TANG Lijun3
Author information
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1.Key Laboratory of Advanced Textile Materials and Manufacturing Technology, Ministry of Education, Zhejiang Sci-Tech University; 2.State Key Laboratory of Fine Chemicals, Dalian University of Technology; 3.Department of Chemistry, Bohai University
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History
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Published |
05 Dec 2008 |
Issue Date |
05 Dec 2008 |
Chlorosulfonyl-containing naphthol azo compounds were prepared by reaction of the corresponding sulfonate-containing naphthol azo dyes with thionyl chloride in the presence of a catalytic quantity of N,N-dimethylformamide and various solvents. The yields and reaction selectivity of chlorosulfonyl-containing naphthol azo compounds were discussed according to the properties of solvents. It was demonstrated that high chemical selectivity and high yield were achieved by using benzene, toluene or thionyl chloride as solvent. Additionally, on account of unstable properties of sulfonyl chloride compounds in MS and 1H-NMR analyses, a new analytical method using stable sulfonamide is put forward to verify the chemical structures of the corresponding sulfonyl chloride compounds indirectly.
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References
1. Fujita S . Anovel and chemoseletive preparation of chlorosulfonyl-containing azodyes with phosphoryl chloride-N,N-dimethylacetamide. J Chem Soc Perkin Trans 1, 1982, 7: 1519–1522. doi:10.1039/p19820001519
2. Tang L J, Zhang S F, Cui Z H, Yang J Z, Gao W T . Synthesis of chlorosulfonyl-containingpyrazolone azo compounds with thionyl chloride-DMF system. Chinese Journal of Chemical Engineering, 2004, 12(5): 719–722
3. Hunger K . IndustrialDyes: Chemistry, Properties, Applications. Weinheim: WILEY-VCH Verlag GmbH &Co. KgaA, 2003, 30–31
4. Jolanta S G, Freeman H S . The synthesis of disperseand cationic dyes from acid dye structures. Dyes and Pigments, 1990, 14(1): 35–48. doi:10.1016/0143-7208(90)87004-M
5. Paquette L A . Encyclopedia of Reagents for Organic Synthesis. Chichester: John Wiley & Sons, 1995, 4873–4876
6. Cheng N L . Handbook of Solvents. Beijing: Chemical Industry Press, 1994 (in Chinese)
7. Tian Y Z, Wu Z W, Zhang S F, Wang G J . Azo-hydrazonetautomerism of 1-phenylazonaphthalene derivatives. Journal of Chemical Industry and Engineering (China), 1995, 46(2): 152–157 (in Chinese)