Industrial methods for producing arylsulfur pentafluorides
View Patent ↗Industrial methods for producing arylsulfur pentafluorides are disclosed. Methods include reacting arylsulfur halotetrafluoride with hydrogen fluoride in the absence or presence of one or more additives selected from a group of fluoride salts, non-fluoride salts, and unsaturated organic compounds to form arylsulfur pentafluorides.
1. A method for preparing an arylsulfur pentafluoride having a formula (I) as follows:
the process comprising:
reacting an arylsulfur halotetrafluoride having a formula (II):
with hydrogen fluoride in the presence of a fluoride salt of formula, M + F − (HF) n , to form the arylsulfur pentafluoride; wherein the mol ratio of an arylsulfur halotetrafluoride to a fluoride salt is in a range of about 1:0.1 to about 1:5 and the mol ratio of an arylsulfur halotetrafluoride to hydrogen fluoride is in a range of about 1:10 to about 1:150;
in which: R 1 , R 2 , R 3 , R 4 , and R 5 each is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or unsubstituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted acyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted alkanesulfonyloxy group having from 1 to 18 carbon atoms, a substituted or unsubstituted arenesulfonyloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, or a SF 5 group;
X is a chlorine atom, bromine atom, or iodine atom;
M is a metal atom, an ammonium moiety, or a phosphonium moiety; and
n is 0 or a mixed number greater than 0.
2. The method of claim 1 wherein X is Cl.
3. The method of claim 1 wherein the fluoride salt is an alkali metal fluoride which is selected from the group consisting of LiF(HF) n , NaF(HF) n , KF(HF) n , RbF(HF) n , and CsF(HF) n in which n is 0 or a mixed number which is greater than 0.