Vinylsulfonic anhydride, method for producing same, and method for producing vinylsulfonyl fluoride

Patent metadata

Field	Value
Publication number	US-11649205-B2
Application number	US-201917055124-A
Country	US
Kind code	B2
Filing date	Jun 20, 2019
Priority date	Jul 9, 2018
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

The present disclosure is directed to provide a vinylsulfonic anhydride which is useful as a synthetic intermediate for synthesis of a fluorinated monomer. It is also directed to efficiently produce the vinylsulfonic anhydride. It is further directed to efficiently produce a fluorinated monomer using the vinylsulfonic anhydride. A vinylsulfonic anhydride of the present disclosure is expressed by the general formula (1). Further, a process for producing a vinylsulfonic anhydride of the present disclosure includes making a vinylsulfonic acid compound represented by the general formula (2) come in contact and be mixed with an anhydridization agent. Further, a process for producing a vinylsulfonyl fluoride of the present disclosure includes a step (b) of making a vinylsulfonic anhydride represented by the general formula (1) come in contact and be mixed with a fluorinating agent to prepare a reaction mixture including a vinylsulfonyl fluoride represented by the general formula (3) and a vinylsulfonic acid compound represented by the general formula (2).

First claim

The invention claimed is:

1. A vinylsulfonic anhydride of general formula (1):

where m is an integer from 0 to 3, and n is an integer from 1 to 6.

2. A process for producing a vinylsulfonic anhydride of general formula (1):

where m is an integer from 0 to 3, and n is an integer from 1 to 6,
the process comprising:
a step (a) of mixing a vinylsulfonic acid compound of general formula (2) with an anhydridization agent:

where m represents an integer from 0 to 3, n represents an integer from 1 to 6, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, Ag, a quaternary ammonium salt, or a quaternary phosphonium salt,
wherein the step (a) comprising a step of separating the vinylsulfonic anhydride of general formula (1).

3. A process for producing a vinylsulfonyl fluoride comprising:
a step (b) of mixing a vinylsulfonic anhydride of general formula (1) with a fluorinating agent:

where m is an integer from 0 to 3, and n is an integer from 1 to 6,
to prepare a reaction mixture comprising a vinylsulfonyl fluoride of general formula (3):

where m is an integer from 0 to 3, and n is an integer from 1 to 6; and
a vinylsulfonic acid compound of general formula (2):

where m represents an integer from 0 to 3, n represents an integer from 1 to 6, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, Ag, a quaternary ammonium salt, or a quaternary phosphonium salt, and
a step (c) of separating the vinylsulfonyl fluoride of general formula (3) and the vinylsulfonic acid compound of general formula (2), from the reaction mixture prepared in the step (b).

4. The process for producing a vinylsulfonyl fluoride according to claim 3 , wherein the vinylsulfonic anhydride is produced by the process for producing a vinylsulfonic anhydride of general formula (1):

where m is an integer from 0 to 3, and n is an integer from 1 to 6,
the process comprising:
a step (a) of mixing a vinylsulfonic acid compound of general formula (2) with an anhydridization agent:

where m represents an integer from 0 to 3, n represents an integer from 1 to 6, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, Ag, a quaternary ammonium salt, or a quaternary phosphonium salt.

5. The process for producing a vinylsulfonic anhydride according to claim 2 , wherein the step (a) comprises mixing the anhydridization agent with the vinylsulfonic acid compound of general formula (2) obtained in the step (c) of separating the vinylsulfonyl fluoride of the general formula (3) and the vinylsulfonic acid compound of general formula (2), from the reaction mixture prepared in the step (b) of mixing a vinylsulfonic anhydride of general formula (1) with a fluorinating agent:

where m is an integer from 0 to 3, and n is an integer from 1 to 6
to prepare a reaction mixture comprising a vinylsulfonyl fluoride of general formula (3):

where m is an integer from 0 to 3, and n is an integer from 1 to 6; and
a vinylsulfonic acid compound of general formula (2):

where m represents an integer from 0 to 3, n represents an integer from 1 to 6, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, Ag, a quaternary ammonium salt, or a quaternary phosphonium salt.

6. The process for producing a vinylsulfonic anhydride according to claim 2 , further comprising a step (d) of mixing an acidic substance with a vinylsulfonic acid compound of general formula:

where m represents an integer from 0 to 3, n represents an integer from 1 to 6, and M represents an alkali metal, an alkaline earth metal, Ag, a quaternary ammonium salt, or a quaternary phosphonium salt,
to prepare the vinylsulfonic acid compound of general formula (4):

that is used in the step (a).

7. The process for producing a vinylsulfonyl fluoride according to claim 3 , wherein the fluorinating agent is one or more selected from the group consisting of hydrogen fluoride, a metal fluoride, a quaternary ammonium fluoride, and a quaternary phosphonium fluoride.

8. The process for producing a vinylsulfonic anhydride according to claim 2 , wherein the anhydridization agent is one or more selected from the group consisting of phosphorus pentoxide, acetic anhydride, trifluoroacetic anhydride, methanesulfonic anhydride, trifluoromethanesulfonic anhydride, p-toluenesulfonic anhydride, thionyl chloride, dicyclohexylcarbodiimide, cyanuric chloride, titanium tetrachloride, and benzenesulfonyl chloride.

9. The process for producing a vinylsulfonic anhydride according to claim 2 , further comprising a step of, after separating the vinylsulfonic anhydride of general formula (1), collecting the vinylsulfonic acid compound of general formula (2) from a resultant residue.

10. The process for producing a vinylsulfonyl fluoride according to claim 2 , wherein m is 0, and n is 2.

Assignees

• Asahi Chemical Ind

Inventors

• Uematsu Nobuyuki
• Date Hideki
• Nagato Yasuhiro
• Nakamura Akitake
• YAKIGAYA Kenichi

Classifications

• C07C309/07 Primary

  containing oxygen atoms bound to the carbon skeleton · CPC title

• C07C309/78

  Halides of sulfonic acids · CPC title

• Y02E60/50

  Fuel cells · CPC title

• C07C303/32

  of salts of sulfonic acids · CPC title

• C07C309/82

  of a carbon skeleton substituted by singly-bound oxygen atoms · CPC title