15484-44-3Relevant articles and documents
Preparation of sodium sulfonates using by copper as catalyst
Bai, Ruijiao,Zhang, Richeng,Qi, Haofei,Yan, Xilong,Chen, Ligong
, p. 7226 - 7228 (2014)
The sodium alkyl sulfonates were prepared by Strecker reaction. The synthesis of sodium chloroethyl sulfonate from dichloroethane and sodium sulfite with different catalysts, it was found that copper was an efficient catalyst with a yield (81%). The reaction conditions were also optimized to make the route more competitive and suitable for large-scale industrial production. Besides, some more sulfonates were also obtained with copper as catalyst via Strecker reaction.
Organic sulfur mechanisms. 24. Preparation and reaction of 2-hydroxyethanesulfonyl chloride, the first hydroxyalkanesulfonyl chloride
King, James Frederick,Hillhouse, John Henry
, p. 1583 - 1593 (2007/10/02)
2-Hydroxyethanesulfonyl chloride (1a) is readily made by reaction of an aqeous solution of 2-mercaptoethanol (4a) with chlorine.This is the first clearly proved preparation of a compound which is both an alcohol and a sulfonyl chloride.Reactions of 1a with water and alcohols evidently proceed largely by intramolecular cyclization to the transient β-sultone (2a), which then undergoes nucleophilic ring opening to form the products.In the presence of tertiary amines a minor but significant part of the reaction is shown by deuterium labelling to proceed via hydroxymethylsulfene (14), the principal reaction of which is simply to add the alcohol or water; only a small part, if any, of the sulfene (14) loses the hydroxyl group to give the ethenesulfonate derivatives (13 or 22).Aqueous chlorination of 3-mercapto-1-propanol gave 3-chloro-1-propanesulfonyl chloride (5a) and 1,3-propane sultone (2b) with no sign of any 3-hydroxy-1-propanesulfonyl chloride (1b).A mechanism for the aqueous chlorination process invoking a cyclic chlorooxasulfoxonium ion (27) is discussed.
