Fluorocarbon perfluoroalkanesulfonates

摘要

1,143,481. Fluorinated alkane sulphonates. MINNESOTA MINING & MFG. CO. 21 Feb., 1966 [5 March, 1965], No. 7597/66. Heading C2C. The invention comprises sulphonate esters of the formula (R # SO 2 OCH 2 ) m Q1, where Rf is a fluorinated C 1-8 acyclic or cyclic alkyl group containing at least 2 fluorine atoms and not more than 1 hydrogen atom, Q1 is a highly fluorinated alkyl group of valence m containing at least 44% by wt. fluorine selected from (a) C 2-17 perfluoroalkyl groups, (b) C 4-11 perfluorocycloalkyl groups, (c) C 2-18 -#-hydroperfluoroalkyl groups having an even number of carbon atoms, (d) C 3-11 -2-hydroperfluoroalkyl groups, (e) a chlorodifluoromethyl group, (f) a 2,2-dichloroperfluoroethyl group, (g) C 3-6 -3-oxa-perfluoroalkyl groups, (h) C 4-6 -perfluoro-oxa-cycloalkyl groups, (i) C 1-10 perfluoroalkylene groups and (j) C 6-12 perfluorocycloalkylene groups, and m is 1 or 2. Compounds of the general formula (RfSO 2 OCH 2 )mQ, where Q is the same as Q1 and may also be a trifluoromethyl group, are prepared by reacting substantially stoichiometric amounts of an alkane sulphonyl halide R f SO 2 X, where X is Cl or F, and a carbinol Q(CR 2 OH)m in the presence of an aliphatic tertiary amine, preferably triethylamine. The esters of the formula (RfSO 2 OCR 2 ) m Q1 are fluoroalkylating agents and react with nucleophilic reagents to give products containing the group Q1-CH 2 -. Thus the esters react with primary and secondary amines to give fluoroalkylated amines, with thiols to give fluoroalkyl sulphides, with hydroxy compounds to give fluoroalkyl ethers, with eneamines of ketones and aldehydes to give fluoroalkylated carbonyl compounds, with diesters of orthophosphorous acid to give fluorinated alkanephosphonates, with alkali metal halides and thiocyanates to give fluoralkyl halides and thiocyanates, with arene sulphonic acid alkali metal salts to give fluoroalkyl arene sulphonates and with hydrazines to give fluoroalkylated hydrazines.