Method of preparing sulfonimide or its salt

• US 5,723,664 A
• Filed: 09/07/1995
• Issued: 03/03/1998
• Est. Priority Date: 09/12/1994
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: Central Glass Company Limited
• Inventors: Fujii, Kenji, Kobayashi, Yoshiyuki, Sakaguchi, Hiroaki, Kita, Yasushi, Sakai, Shigenori
• Primary Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US08/525,439
• Time in Patent Office: 908 Days
• Field of Search: 564/82
• US Class Current: 564/82
• CPC Class Codes: C07C 303/38 by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
• CPC Class Codes: C07C 311/09 the carbon skeleton being further substituted by at least two halogen atoms
• CPC Class Codes: C07D 213/20 Quaternary compounds thereof

Abstract

The invention relates to a method of preparing a sulfonimide, a first salt thereof, or a second salt thereof. The method includes the step of: (a) reacting one or two sulfonyl fluorides with nonhydrous ammonia and an amine component which is one of a tertiary amine and a heterocyclic amine, so as to prepare the first salt. Alternatively, the method includes the step of: (a) reacting the sulfonyl fluoride with the amine component and a sulfonamide, so as to prepare the first salt. The method further optionally includes, after the step (a), the step of: (b) reacting, in an aqueous solution, the first salt with a metal compound, so as to prepare the second salt. The method still further optionally includes, after the step (a), the step of: (c) reacting the first salt with a strong acid so as to prepare the sulfonimide. Alternatively, the method further optionally includes, after the step (b), the step of: (d) reacting the second salt with a strong acid so as to prepare the sulfonimide. The sulfonimide, the first salt or the second salt is easily economically prepared in an industrial scale production with high purity and high yield.

Claims

1. A method of preparing a sulfonimide represented by the general formula (1), a first salt thereof represented by the general formula (2), or a second salt thereof represented by the general formula (3), the method comprising the step of:

(a) reacting one or two sulfonyl fluorides represented by the general formula (4) with nonhydrous ammonia and an amine component which is one of a tertiary amine represented by the general formula (5) and a heterocyclic amine, so as to prepare said first salt,

space="preserve" listing-type="equation">H Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 ! (1)

wherein "Rf¹ " and "Rf² " represent the same or different groups each of which has a carbon atom number from 1 to 12 and is straight-chain or branched-chain and one selected from the group consisting of perfluoroalkyl groups, fluoroalkyl groups, fluoroalkenyl groups and fluoroallyl groups,

space="preserve" listing-type="equation">M.sup.1 Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 !.sub.n1 (

     2)

wherein "Rf¹ " and "Rf² " are defined as above;

"M¹ " represents a positive ion having a first valence; and

"n1" represents an integer that is the same as said first valence,

space="preserve" listing-type="equation">M.sup.2 Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 !.sub.n2 (

     3)

wherein "Rf¹ " and "Rf² " are defined as above;

"M² " represents an alkali or alkali earth metal atom having a second valence; and

"n2" represents an integer that is the same as said second valence,

space="preserve" listing-type="equation">RfSO.sub.2 F (4)

wherein "Rf" represents the same or different groups which are identical with said "Rf¹ " and said "Rf² ",

space="preserve" listing-type="equation">(R.sub.1).sub.3 N (5)

wherein "R¹ " represents the same or different alkyl groups each having a carbon atom number from 1 to 5.

2. A method according to claim 1, wherein, after the step (a), the method further comprises the step of:

(b) reacting, in an aqueous solution, said first salt with a metal compound selected from the group consisting of hydroxides, oxides and carbonates, said metal compound containing said alkali or alkali earth metal atom, so as to prepare said second salt.

3. A method according to claim 1, wherein, after the step (a), the method further comprises the step of:

(c) reacting the first salt with a strong acid so as to prepare said sulfonimide.

4. A method according to claim 2, wherein, after the step (b), the method further comprises the step of:

(d) reacting the second salt with a strong acid so as to prepare said sulfonimide.

9. A method according to claim 1, wherein each of said "Rf¹ " and said "Rf² " is a perfluoroalkyl group.

11. A method according to claim 9, wherein each said perfluoroalkyl group is a member selected from the group consisting of trifluoromethyl group, perfluorobutyl group, perfluorooctyl group, and pentafluorobenzene group.

12. A method according to claim 11, wherein each said perfluoroalkyl group is a member selected from the group consisting of said trifluoromethyl group and said perfluorobutyl group.

5. A method of preparing a sulfonimide represented by the general formula (1), a first salt thereof represented by the general formula (2), or a second salt thereof represented by the general formula (3), the method comprising the step of:

(a) reacting a sulfonyl fluoride represented by the general formula (4) with an amine component which is one of a tertiary amine represented by the general formula (5) and a heterocyclic amine and a sulfonamide represented by the general formula (6),

space="preserve" listing-type="equation">H Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 ! (1)

wherein "Rf¹ " and "Rf² " represent the same or different groups each of which has a carbon atom number from 1 to 12 and is straight-chain or branched-chain and one selected from the group consisting of perfluoroalkyl groups, fluoroalkyl groups, fluoroalkenyl groups and fluoroallyl groups,

space="preserve" listing-type="equation">M.sup.1 Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 !.sub.n1 (

     2)

wherein "Rf¹ " and "Rf² " are defined as above;

"M¹ " represents a positive ion having a first valence; and

"n1" represents an integer that is the same as said first valence,

space="preserve" listing-type="equation">M.sup.2 Rf.sup.1 SO.sub.2 --N--SO.sub.2 Rf.sup.2 !.sub.n2 (

     3)

wherein "Rf¹ " and "Rf² " are defined as above;

"M² " represents an alkali or alkali earth metal atom having a second valence; and

"n2" represents an integer that is the same as said second valence,

space="preserve" listing-type="equation">RfSO.sub.2 F (4)

wherein "Rf" represents the same or different groups which are identical with said "Rf¹ " and said "Rf² ",

space="preserve" listing-type="equation">(R.sup.1).sub.3 N (5)

wherein "R¹ " represents the same or different alkyl groups each having a carbon atom number from 1 to 5,

space="preserve" listing-type="equation">RfSO.sub.2 NH.sub.2 (

     6)

wherein "Rf" is defined as above.

6. A method according to claim 5, wherein, after the step (a), the method further comprises the step of:

(b) reacting, in an aqueous solution, said first salt with a metal compound selected from the group consisting of hydroxides, oxides and carbonates, said metal compound containing said alkali or alkali earth metal atom, so as to prepare said second salt.

7. A method according to claim 5, wherein, after the step (a), the method further comprises the step of:

(c) reacting the first salt with a strong acid so as to prepare said sulfonimide.

8. A method according to claim 6, wherein, after the step (b), the method further comprises the step of:

(d) reacting the second salt with a strong acid so as to prepare said sulfonimide.

10. A method according to claim 5, wherein each of said "Rf¹ " and said "Rf² " is a perfluoroalkyl group.

13. A method according to claim 10, wherein said perfluoroalkyl group is a member selected from the group consisting of trifluoromethyl group, perfluorobutyl group, perfluorooctyl group, and pentafluorobenzene group.

14. A method according to claim 13, wherein said perfluoroalkyl group is a member selected from the group consisting of said trifluoromethyl group and said perfluorobutyl group.