IP Library Granted Patent US 8,067,585
Granted Patent B2
US 8,067,585 · App. 11/865,267 · Granted Nov 29, 2011

Method for producing disulfonyl fluoride compound

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Quick Facts
Patent No.
US 8,067,585
App. No.
11/865,267
Granted
Nov 29, 2011
Kind
B2
Abstract

The present invention relates to producing a disulfonyl fluoride compound easily and efficiently by utilizing coupling reaction where a compound (2) is obtained by subjecting a compound (1) wherein Y is a fluorine atom to photocoupling reaction, or subjecting a compound (1) wherein Y is a hydroxyl group, —OM a wherein M a is an alkali metal atom, or —O(M b ) 1/2 wherein M b is an alkaline earth metal atom to electrolytic coupling reaction, and derivatives such as the following compound (7A) are obtained from the compound (2): FSO 2 -E-CX 2 —COY  (1) FSO 2 -E-CX 2 —CX 2 -E-SO 2 F  (2) wherein E is a single bond, —O—, a C 1-20 alkylene group which may contain an etheric oxygen atom, or the like, X is a fluorine atom or the like, and Y is a fluorine atom, a hydroxyl group, or the like.

Claims (30)

1. A method for producing a compound represented by the following formula (2), which comprises subjecting a compound represented by the following formula (1) in which Y is a fluorine atom to photocoupling reaction or the compound in which Y is a hydroxyl group, —OMa or —O(M b ) 1/2 to electrolytic coupling reaction, to obtain the compound represented by the following formula (2):

FSO 2 -E-CX 2 —COY  (1)

FSO 2 -E-CX 2 —CX 2 -E-SO 2 F  (2)

wherein E is a single bond, an etheric oxygen atom, a

C 1-20 alkylene group which may contain an etheric oxygen atom, or a group having at least one hydrogen atom in such an alkylene group substituted by a fluorine atom and/or a chlorine atom; X each independently is a hydrogen atom, a chlorine atom or a fluorine atom; and Y is a fluorine atom, a hydroxyl group, —OM a (wherein M a is an alkali metal atom) or —O(M b ) 1/2 (wherein M b is an alkaline earth metal atom).

2. A method for producing a compound represented by the following formula (3), which comprises reacting the compound represented by the formula (2) obtained by the production method as defined in claim 1 with ammonia:

wherein symbols are as defined above.

3. A method for producing a compound represented by the following formula (4), which comprises heating the compound represented by the formula (3) obtained by the production method as defined in claim 2 in the presence of a protic acid:

wherein symbols are as defined above.

4. A method for producing a compound represented by the following formula (5), which comprises reacting the compound represented by the formula (3) obtained by the production method as defined in claim 2 with a metal salt containing a n-valent metal represented by the formula M:

wherein E and X are as defined above, n is an integer of from 1 to 4, M is a n-valent metal, and (M) n+ is a n-valent metal cation.

5. A method for producing a compound represented by the following formula (5), which comprises reacting the compound represented by the formula (4) obtained by the production method as defined in claim 3 with a metal salt containing a n-valent metal represented by the formula M:

wherein E and X are as defined above, n is an integer of from 1 to 4, M is a n-valent metal, and (M) n+ is a n-valent metal cation.

6. A method for producing a compound represented by the following formula (6), which comprises reacting the compound represented by the formula (4) obtained by the production method as defined in claim 3 with fluorine:

wherein symbols are as defined above.

7. A method for producing a compound represented by the following formula (6), which comprises reacting the compound represented by the formula (5) obtained by the production method as defined in claim 4 with fluorine:

wherein symbols are as defined above.

8. A method for producing a compound represented by the formula (7), which comprises reacting the compound represented by the formula (4) obtained by the production method as defined in claim 3 with an alkylating agent having a group represented by the formula R:

wherein E and X are as defined above, and R is a C 1-10 alkyl group which may contain an etheric oxygen atom or a nitrogen atom.

9. A method for producing a compound represented by the following formula (9), which comprises reacting the compound represented by the formula (4) obtained by the production method as defined in claim 3 with a compound represented by the following formula (8):

[(Z 1 ) + (R 1 )(R 2 )(R 3 )(R 4 )] k (L) k−   (8)

wherein E and X are as defined above; Z 1 is a nitrogen atom or a phosphorus atom; each of R 1 , R 2 , R 3 and R 4 which are independent of one another, is a C 1-10 monovalent hydrocarbon group which may contain at least one atom selected from the group consisting of an etheric oxygen atom, a nitrogen atom and a phosphorus atom, or a hydrogen atom; or two to four groups selected from R 1 , R 2 , R 3 and R 4 are bonded to form a cyclic structure, and when there is a remaining group not forming a cyclic structure, the remaining group is a C 1-10 monovalent hydrocarbon group which may contain at least one atom selected from the group consisting of an etheric oxygen atom, a nitrogen atom and a phosphorus atom, or a hydrogen atom; (L) k− is a k-valent anion; and k is 1 or 2.

10. A method for producing a compound represented by the following formula (11), which comprises reacting the compound represented by the formula (7) obtained by the production method as defined in claim 8 with a compound represented by the following formula (10):

Z 2 (R 5 )(R 6 )(R 7 )  (10)

wherein E and X are as defined above; Z 2 is a nitrogen atom or a phosphorus atom; and each of R 5 , R 6 and R 7 which are independent of one another, is a C 1-10 aliphatic hydrocarbon group which may contain at least one atom selected from the group consisting of an etheric oxygen atom, a nitrogen atom and a phosphorus atom, or a hydrogen atom or an aryl group; or two or three groups selected from R 5 , R 6 and R 7 are bonded to form a cyclic structure, and when there is a remaining group not forming a cyclic structure, the remaining group is a C 1-10 aliphatic hydrocarbon group which may contain at least one atom selected from the group consisting of an etheric oxygen atom, a nitrogen atom and a phosphorus atom, or a hydrogen atom or an aryl group.

11. The production method according to claim 1 , wherein E is a single bond, a C 1-20 alkylene group, or a group having at least one hydrogen atom in the C 1-20 alkylene group substituted by a fluorine atom and/or a chlorine atom.

12. The production method according to claim 1 , wherein E is a single bond.

13. The production method according to claim 1 , wherein Y is a hydroxyl group, —OM a (wherein M a is an alkali metal atom) or —O(M b ) 1/2 (wherein M b is an alkaline earth metal atom).

14. The production method according to claim 1 , wherein Y is a hydroxyl group or —OM a (wherein M a is an alkali metal atom).

15. The production method as defined in claim 1 , herein X is a fluorine atom.

Assignments (4)
CHANGE OF NAME Recorded Aug 7, 2018
From: ASAHI GLASS COMPANY, LIMITED
To: AGC INC.
Reel/Frame 046730/0786 →
CORPORATE ADDRESS CHANGE Recorded Nov 9, 2011
From: ASAHI GLASS COMPANY, LIMITED
To: ASAHI GLASS COMPANY, LIMITED
Reel/Frame 027197/0541 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S NAME PREVIOUSLY RECORDED ON REEL 019905 FRAME 0836. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 16, 2008
From: IWAYA, MASAO; OHARU, KAZUYA; OKAMOTO, HIDEKAZU
To: ASAHI GLASS COMPANY, LIMITED
Reel/Frame 021241/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 2, 2007
From: IWAYA, MASAO; OHARU, KAZUYA; OKAMOTO, HIDEKAZU
To: ASAHI GLASS COMPANY, LTD.
Reel/Frame 019905/0836 →