萘酚磺酸类偶氮化合物酰氯化研究

以萘酚磺酸类偶氮化合物酸性橙7为原料,氯化亚砜为酰氯化试剂,N,N-二甲基甲酰胺(DMF)为催化剂,合成重要的染料中间体磺酰氯化合物.选择不同极性试剂作为酰氯化反应的溶剂,考查了不同溶剂对酰氯化收率和选择性的影响.并探讨了DMF在反应体系中的作用以及酰氯化反应的机理;其中以苯、甲苯和氯化亚砜作溶剂,反应选择性好,收率均高于89%.此外,鉴于磺酰氯在质谱与核磁分析中的不稳定性,以稳定的磺酰胺分析代替直接的磺酰氯分析,间接地证明了磺酰氯的分子结构.

Research on sulfonyl chlorination of sulfonate-containing naphthol azo compounds

Chlorosulfonyl-containing naphthol azo compounds were prepared by reaction of the corresponding sodium sulfonate (C.I. Acid Orange 7) with thionyl chloride in the presence of a catalytic quantity of N,N-dimethylformamide and some different solvents. The yield and chemical selectivity of chlorosulfonyl-containing naphthol azo compounds are discussed according to the properties of different solvents. It was demonstrated that high selectivity and high yield(>89%) were achieved by using benzene, toluene or thionyl chloride as solvent. Additionally, on account of unstable properties of sulfonyl chlorides in MS and 1H NMR analyses, a new analytical method using stable sulfonamide is put forward to testify the molecular structures of sulfonyl chlorides indirectly.