Fluorosulfonyl group-containing compound, fluorosulfonyl group-containing monomer, and their production methods

Patent metadata

Field	Value
Publication number	US-11242420-B2
Application number	US-202016801222-A
Country	US
Kind code	B2
Filing date	Feb 26, 2020
Priority date	Sep 1, 2017
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

A method for producing a fluorosulfonyl group-containing compound to obtain a compound represented by the following formula 5 from a compound represented by the following formula 1 as a starting material and a method for producing a fluorosulfonyl group-containing monomer in which the fluorosulfonyl group-containing compound is used:

wherein R 1 and R 2 are a C 1-3 alkylene group, and R F1 and R F2 are a C 1-3 perfluoroalkylene group.

First claim

The invention claimed is:

1. A method for producing a fluorosulfonyl group-containing compound, which comprises:
reacting a compound represented by the following formula 1 with a sulfonating agent to obtain a compound represented by the following formula 2,
reacting the compound represented by the following formula 2 with a chlorinating agent to obtain a compound represented by the following formula 3,
reacting the compound represented by the following formula 3 with a fluorinating agent to obtain a compound represented by the following formula 4, and
subjecting the compound represented by the following formula 4 to fluorination treatment to obtain a compound represented by the following formula 5:

wherein R 1 and R 2 are a C 1-3 alkylene group, and R F1 and R F2 are a C 1-3 perfluoroalkylene group.

2. A method for producing a fluorosulfonyl group-containing monomer, which comprises:
obtaining the compound represented by the formula 5 by the method for producing a fluorosulfonyl group-containing compound as defined in claim 1 , and
reacting the compound represented by the formula 5 with a perfluoroallylating agent to obtain a compound represented by the following formula 7:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

3. A method for producing a fluorosulfonyl group-containing monomer, which comprises:
obtaining the compound represented by the formula 5 by the method for producing a fluorosulfonyl group-containing compound as defined in claim 1 ,
adding 2 moles of hexafluoropropylene oxide to 1 mole of the compound represented by the formula 5 in the presence of a metal fluoride to obtain a compound represented by the following formula 8a, and thermally decomposing the compound represented by the following formula 8a to obtain a compound represented by the following formula 9a:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

4. A method for producing a fluorosulfonyl group-containing monomer, which comprises
obtaining the compound represented by the formula 5 by the method for producing a fluorosulfonyl group-containing compound as defined in claim 1 ,
adding 1 mole of hexafluoropropylene oxide to 1 mole of the compound represented by the formula 5 in the presence of a metal fluoride to obtain a compound represented by the following formula 8b, and thermally decomposing the compound represented by the following formula 8b to obtain a compound represented by the following formula 10:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

5. A method for producing a fluorosulfonyl group-containing monomer, which comprises reacting a compound represented by the following formula 5 with a perfluoroallylating agent to obtain a compound represented by the following formula 7:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

6. A method for producing a fluorosulfonyl group-containing monomer, which comprises adding 2 moles of hexafluoropropylene oxide to 1 mole of a compound represented by the following formula 5 in the presence of a metal fluoride to obtain a compound represented by the following formula 8a, and thermally decomposing the compound represented by the following formula 8a to obtain a compound represented by the following formula 9a:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

7. A method for producing a fluorosulfonyl group-containing monomer, which comprises adding 1 mole of hexafluoropropylene oxide to 1 mole of a compound represented by the following formula 5 in the presence of a metal fluoride to obtain a compound represented by the following formula 8b, and thermally decomposing the compound represented by the following formula 8b to obtain a compound represented by the following formula 10:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

8. A fluorosulfonyl group-containing compound, which is either one or both of a compound represented by the following formula 5 and a compound represented by the following formula 5′:

wherein R F1 and R F2 are a CF 2 group.

9. A fluorosulfonyl group-containing monomer, which is a compound represented by the following formula 7:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

10. A fluorosulfonyl group-containing monomer, which is a compound represented by the following formula 10:

wherein R F1 and R F2 are a C 1-3 perfluoroalkylene group.

Assignees

• Agc Inc

Inventors

• Hirai Takeshi
• Jomuta Daisuke
• Tamitsuji Chikaya

Classifications

• C08F214/262

  with fluorinated vinyl ethers · CPC title

• C25B9/23

  comprising ion-exchange membranes in or on which electrode material is embedded · CPC title

• C25B1/04

  by electrolysis of water · CPC title

• H01M8/1007

  with both reactants being gaseous or vaporised (H01M8/12 takes precedence) · CPC title

• H01M4/8663

  Selection of inactive substances as ingredients for catalytic active masses, e.g. binders, fillers · CPC title