Fluorolactone and method for producing same

Patent metadata

Field	Value
Publication number	US-12043606-B2
Application number	US-202117521155-A
Country	US
Kind code	B2
Filing date	Nov 8, 2021
Priority date	May 13, 2019
Publication date	Jul 23, 2024
Grant date	Jul 23, 2024

Abstract

The present disclosure provides, for example, a method that can produce a fluorolactone compound from hexafluoropropylene oxide or the like in a single step. The present disclosure relates to a method for producing a compound represented by formula (1):

wherein two R 1 are the same and each is a fluorine atom or a fluoroalkyl group,
the method comprising step A of reacting a compound represented by formula (2):

wherein R 1 is as defined above, with a compound represented by formula (3):

wherein R 31 , R 32 , and R 33 are the same or different and each is a hydrogen atom or an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents, and
a compound represented by formula (4-1) or the like:

wherein R 41 , R 42 , R 43 , and R 44 are the same or different and each is a hydrogen atom ox an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents.

First claim

The invention claimed is:

1. A method for producing a compound represented by formula (1):

wherein two R 1 are the same and each is a fluorine atom or a fluoroalkyl group,
the method comprising step A of reacting a compound represented by formula (2):

wherein R 1 is as defined above, with a compound represented by formula (3):

wherein R 31 , R 32 , and R 33 are the same or different and each is a hydrogen atom or an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents; and
a compound represented by formula (4-1):

wherein R 41 , R 42 , R 43 , and R 44 are the same or different and each is a hydrogen atom or an alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents.

2. The production method according to claim 1 , wherein step A is performed in the presence of an organic solvent, provided that the compounds represented by formulas (3) and (4-1) are excluded from the organic solvent.

3. The production method according to claim 1 , wherein step A is a step of generating an upper liquid layer and a lower liquid layer, and the method further comprises step B of separating these layers.

4. The production method according to claim 1 , wherein R 41 , R 42 , R 43 , and R 44 are the same or different and each is a hydrogen atom or a C 1-10 alkyl group, or two of them are optionally linked to each other to form a ring optionally having one or more substituents.

5. The production method according to claim 1 , wherein R 41 and R 42 are the same or different and each is a C 1-5 alkyl group, and R 43 and R 44 are the same or different and each is a C 1-5 alkyl group, or are linked to each other to form a ring optionally having one or more substituents.

6. The production method according to claim 1 , wherein the compound represented by formula (4-1) is at least one compound selected from the group consisting of N,N′-dimethylpropylene urea, N,N′-dimethylethylene urea, and tetramethyl urea.

7. The production method according to claim 1 , wherein in step A, the compound represented by formula (2) is supplied as gas, the amount of the compound represented by formula (2) is 70 mass % to 99.8 mass % based on the weight of the gas, and the amount of the compound represented by formula (4-1) is 0.001 to 0.3 mol per mol of the compound represented by formula (2).

8. The production method according to claim 1 , wherein step A does not include CsF.

9. A method for producing a compound represented by formula (5):

wherein R 1 is a fluorine atom or a fluoroalkyl group,
the method comprising:
step of producing a compound represented by formula (1) by step A according to claim 1 , optionally wherein step A is a step of generating an upper liquid layer and a lower liquid layer, and the method further comprises separating these layers:

wherein two R 1 are the same and each is a fluorine atom or a fluoroalkyl group; and
steps C of heating the compound represented by formula (1) produced in above step in the presence of at least one fluorine compound (9) selected from the group consisting of:
a compound represented by formula (9-1):
MH n F m   (9-1)

wherein M is a metal atom, n is 0 or 1, and the sum of the valence number of M and n is m;
a compound represented by formula (9-2):
LR 91 4 F  (9-2)

wherein L is a nitrogen atom or a phosphorus atom, and R 91 are the same or different and each is a C 1-5 alkyl group; and
hydrofluoric acid or a salt thereof,

to produce a compound represented by formula (6):

wherein R 1 are as defined above;
step D of reacting the compound represented by formula (6) with a base to produce a compound represented by formula (8):

wherein R 71 is a group corresponding to the base, and R 1 are as defined above; and
step E of heating the compound represented by formula (8) to produce the compound represented by formula (5).

10. The production method according to claim 9 , comprising, in place of step D:
step D1 of reacting the compound represented by formula (6) with water or alkyl alcohol to produce a compound represented by formula (7):

wherein R 71 is a hydrogen atom or an alkyl group, and R 1 are as defined above; and
step D2 of reacting the compound represented by formula (7) with a base to produce the compound represented by formula (8).

11. The production method according to claim 10 , further comprising step D1a of purifying a product of step D1 to obtain the compound represented by formula (7).

12. The production method according to claim 9 , comprising, in place of steps D and E, step F of heating the compound represented by formula (6) in the presence of a base to produce the compound represented by formula (5).

Assignees

• Daikin Ind Ltd

Inventors

• Hosokawa Moe
• Hayashi Koutarou
• Yamamoto Yoshihiro
• Yamauchi Akiyoshi
• Matsuura Makoto
• Kishikawa Yosuke

Classifications

• C07D317/42

  Halogen atoms or nitro radicals · CPC title

• C07D319/12 Primary

  not condensed with other rings · CPC title