Process for producing fluorinated sulfonyl fluoride compound
It is an object of the present invention to solve difficulty in production and to provide a process to obtain fluorinated sulfonyl fluoride compound having various molecular structures efficiently at a low cost. That is, the present invention provides a process which comprises reacting (FSO 2 —) n R A (-E-R B ) m (1F) with fluorine in a liquid phase to form (FSO 2 —) n R AF (-E F -R BF ) m (2), and decomposing this compound to obtain (FSO 2 —) n R AF (-E F1 ) m (3), provided that R A is a (n+m) valent organic group having at least two carbon atoms, R AF is a group having R A fluorinated, or the like, each of R B and R BF is a fluorinated monovalent organic group, or the like, E is —COOCH 2 — or the like, E F is —COOCF 2 — or the like, E F1 is —COF or the like, n is an integer of at least 2, and m is an integer of at least 1.
1. A process for producing a compound represented by the following formula (3a-1), which comprises oxidizing a compound represented by the formula (7-a) by reacting it with chlorine in a solvent comprising water to obtain a compound represented by the following formula (1-a), fluorinating the compound represented by the formula (1-a) to obtain a compound represented by the following formula (1F-a), reacting the compound represented by the formula (1F-a) with fluorine in a liquid phase to obtain a compound represented by the following formula (2-a), and carrying out a decomposition reaction of an ester bond in the compound represented by the formula (2-a):
(Y-S) p R C (—CH 2 OCOR—R BF ) q (7-a)
(ClSO 2 —) p R C (—CH 2 OCO—R BF ) q (1-a)
(FSO 2 —) p R C (—CH 2 OCO—R BF ) q (1F-a)
(FSO 2 —) p R CF (—CF 2 OCO—R BF ) q (2-a)
(FSO 2 —) p R CF (—COF)) q (3a-1)
wherein Y is a hydrogen atom, a monovalent organic group or a —SO 3 − M + group (wherein M is an alkali metal atom), R C is a (p+q)valent organic group having at least two carbon atoms and containing no fluorine atom, R CF is a group having R C perfluorinated and represents a perfluorinated (p+q)valent organic group having at least two carbon atoms, R BF is a perfluorinated monovalent organic group, p is 2 or 3, and q is 1 or 2.
2. A compound represented by the following formula (3a-1):
(FSO 2 —) p R CF (—COF)) q (3a-1)
wherein R CF is a perfluorinated (p+q)valent organic group having at least two carbon atoms, p is 2 or 3, and q is 1 or 2.
3. A compound represented by the following formula (3a-11):
wherein a is an integer of from 1 to 3, b is an integer of from 1 to 3, and Q F is a single bond or a C 1-4 perfluoroalkylene group which may contain an etheric oxygen atom.
4. A process for producing a compound represented by the following formula (12a), which comprises adding hexafluoropropylene oxide to a compound represented by the following formula (3a):
(FSO 2 —) n R AF (—COF) m (3a)
(FSO 2 —) n R AF (—CF 2 OCF(CF 3 )COF) m (12a)
wherein R AF is the same group as R A or a (n+m)valent organic group having R A fluorinated, n is an integer of 2 or more, and m is an integer of 1 or more.
5. A compound represented by the following formula (12a-1):
(FSO 2 ) p R CF (—CF 2 OCF(CF 3 )COF)) q (12a- 1)
wherein R CF is a perfluorinated (p+q)valent organic group having at least two carbon atoms, p is 2or 3, and q is 1 or 2.
6. A compound represented by the following formula (12a-11):
wherein a is an integer of from 1 to 3, b is an integer of from 1 to 3, Q F is a single bond or a C 1-6 perfluoroalkylene group which may contain an etheric oxygen atom.
7. The process according to claim 1 , wherein said solvent further comprises acetic acid.
8. The process according to claim 1 , wherein said solvent further comprises acetonitrile.
9. The compound according to claim 2 , wherein R CF is a perfluorinated (p+q)valent organic group having at least three carbon atoms.
10. The compound according to claim 2 , wherein R CF is a perfluorinated (p+q)valent organic group having from three to sixteen carbon atoms.
11. The compound according to claim 2 , wherein R CF is a perfluorinated (p+q)valent organic group having from four to sixteen carbon atoms.
12. The compound according to claim 2 , wherein R CF is a perfluorinated (p+q)valent organic group having from five to sixteen carbon atoms.
13. The compound according to claim 3 , wherein said compound is represented by the following formula:
(FSO 2 —CF 2 ) 2 CF—COF
wherein a is 1, b is 1, and Q F is a single bond.
14. The compound according to claim 3 , wherein Q F is a C 1-6 perfluoroalkylene group having a terminal etheric oxygen bonded to CF, which is a perfluorinated trivalent organic group.
15. The compound according to claim 13 , wherein said compound is represented by the following formula:
(FSO 2 —CF 2 ) 2 CFOCF 2 CF 2 COF
wherein a is 1, b is 1, and Q F is a C 2 perfluoro(oxyethylene) group.