Sulfochlorination sulfuryl chloride

The free-radical-induced reaction of alkanes with sulfuryl chloride characteristically results in the chlorination of hydrocarbons. However, when pyridine is added to the irradiated reactants, sulfochlorination occurs in quite satisfactory yield. For example, the irradiated reaction of cyclohexane and sulfuryl chloride in the presence of pyridine resulted in a 54.8% yield of cyclohexanesulfonyl chloride and only 9.4% of chlorocyclohexane.161... 

Sulfuryl fluoride is not especially reactive, whereas sulfuryl chloride is extensively used in industry. It readily dissociates into SO2 and chlorine, and is widely used for chlorination (particularly selective side-chain chlorination of aromatics) and sulfochlorination (introduction of SO2CI) in organic chemical manufacture for dyes, disinfectants, herbicides, and so on. 

Application Sulfuryl chloride is used as a chlorination and sulfochlorination agent in the organic chemical industry, in particular for selective chlorination (e.g. for the side chains of aromatic compounds) and in the manufacture of organic intermediates for dyes, pharmaceuticals, pesticides and disinfectants. 

An alternative process to classical sulfochlorination with the gas mixture uses liquid sulfuryl chloride the reaction is operated under UV or visible light (X = 300-500 nm). 

Kharasch et al. [48] had proposed a mechanism for the sulfochlorination with sulfuryl chloride in the presence of pyridine, simply assuming the dissociation of SOjClj into chlorine and sulfur dioxide, but the different secondary/primary selectivity with respect to that of the SOj—Clj mixture [41] suggests three more possible steps [42] ... 

A variation of sulfochlorination with sulfuryl chloride involves a highly selective porphyrin catalyst that is active in the absence of light, but giving favorable results only in benzene as a solvent [49]. 

Azira, H., Assassi, N. and Tazerouti, A., Synthesis of long-chain alkanesulfonates by sulfochlorination using sulfuryl chloride, 7. Surf. Det., 6(1), 55, 2003. 

Dimethylformamide-sulfuryl chloride-sulfur trioxide HC0N(CH )2-S02Cl2-S0 Sulfochlorination H SO2GI... 

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