Production methods for 1,3-dioxolane compound and perfluoro(2,2-dimethyl-1,3-dioxole)

Patent metadata

Field	Value
Publication number	US-10975053-B2
Application number	US-202016936512-A
Country	US
Kind code	B2
Filing date	Jul 23, 2020
Priority date	Feb 1, 2018
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

The present invention relates to a method for producing a 1,3-dioxolane compound represented by formula 1, the method containing step (a), in which hexafluoroacetone monohydrate is brought into contact with a metal fluoride, step (b), in which fluorine gas is brought into contact, and step (c), in which an olefin compound represented by formula 2 is brought into contact. In formulae 1 and 2, X 1 to X 4 each independently represent a hydrogen atom, fluorine atom, chlorine atom, or trifluoromethyl group.

First claim

The invention claimed is:

1. A method for producing a 1,3-dioxolane compound represented by the following formula 1, containing the following step (a) to step (c):
step (a): a step of bringing hexafluoroacetone monohydrate into contact with a metal fluoride,
step (b): a step of bringing a fluorine gas into contact, and
step (c): a step of bringing an olefin compound represented by the following formula 2 into contact,

in the formulas 1 and 2, X 1 to X 4 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, or a trifluoromethyl group.

2. The method for producing a 1,3-dioxolane compound according to claim 1 , comprising using cesium fluoride, potassium fluoride or sodium fluoride as the metal fluoride in the step (a).

3. The method for producing a 1,3-dioxolane compound according to claim 1 , comprising setting a reaction temperature in the step (b) to −196 to 0° C.

4. The method for producing a 1,3-dioxolane compound according to claim 1 , comprising using a fluorine gas diluted to 0.1 to 50% by volume as the fluorine gas in the step (b).

5. The method for producing a 1,3-dioxolane compound according to claim 1 , wherein at least one of X 1 and X 2 and at least one of X 3 and X 4 of the olefin compound represented by the formula 2 are both fluorine atoms.

6. The method for producing a 1,3-dioxolane compound according to claim 1 , wherein the olefin compound represented by the formula 2 is one or more selected from the group consisting of 1,2-dichloro-1,2-difluoroethylene, 1, 1,2-trifluoroethylene, tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, and 1,2-difluoroethylene.

7. The method for producing a 1,3-dioxolane compound according to claim 1 , wherein the steps (a), (b) and (c) are performed in this order.

8. A method for producing perfluoro(2,2-dimethyl-1,3-dioxole) represented by the following formula 3, comprising the following steps (a), (b), (c)′, and (d):
step (a): a step of bringing hexafluoroacetone monohydrate into contact with a metal fluoride,
step (b): a step of bringing a fluorine gas into contact,
step (c)′: a step of bringing an olefin compound represented by the following formula 2′ into contact, and
step (d): a step of eliminating X 1 and X 3 in the following formula 2′,

in the formulas 1′ and 2′, X 1 and X 3 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, or a trifluoromethyl group.

9. The method for producing perfluoro(2,2-dimethyl-1,3-dioxole) according to claim 8 , wherein the olefin compound represented by the formula 2′ is one or more selected from the group consisting of 1,2-dichloro-1,2-difluoroethylene, 1, 1,2-trifluoroethylene, tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, and 1,2-difluoroethylene.

10. The method for producing perfluoro (2,2-dimethyl-1,3-dioxole) according to claim 8 , wherein the steps (a), (b), (c)′, and (d) are performed in this order.

Assignees

• Agc Inc

Inventors

• Jomuta Daisuke
• Takahira Yusuke
• Otozawa Nobuyuki
• Tamitsuji Chikaya

Classifications

• C07D317/42 Primary

  Halogen atoms or nitro radicals · CPC title

• C07B61/00

  Other general methods · CPC title