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