Method for producing fluorine-containing substituted compound and fluorine-containing substituted compound

Patent metadata

Field	Value
Publication number	US-9255114-B2
Application number	US-201314021049-A
Country	US
Kind code	B2
Filing date	Sep 9, 2013
Priority date	Mar 10, 2011
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

A method for producing a fluorine-containing substituted compound, the method including: introducing an organofluorine compound and an organolithium compound into a microreactor provided with a flow path capable of mixing a plurality of liquids, to thereby obtain a reaction product; and introducing, into the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.

First claim

What is claimed is:

1. A method for producing a fluorine-containing substituted compound, the method comprising: introducing a fluoroalkylhalide and an organolithium compound into a first flow path in a microreactor provided with a plurality of flow paths capable of mixing a plurality of liquids, to thereby obtain a reaction product; and
introducing, into a second flow path in the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.

2. The method according to claim 1 , wherein the fluoroalkylhalide is a fluoroalkyl halide having 6 carbon atoms, and
wherein a temperature T (° C.) inside the first flow path of the microreactor into which the fluoroalkylhalide and the organolithium compound have been introduced and a residence time t (sec) thereof in the first flow path of the microreactor satisfy the following relation: T≦−3.8t−48.

3. The method according to claim 1 , wherein the fluoroalkylhalide is a fluoroalkyl halide having 2 carbon atoms, and
wherein a temperature T (° C.) inside the first flow path of the microreactor into which the fluoroalkylhalide and the organolithium compound have been introduced and a residence time t (sec) thereof in the first flow path of the microreactor satisfy the relations −100≦T≦0 and 0.15≦t≦8.4, respectively.

4. The method according to claim 1 , wherein the fluoroalkylhalide is a fluoroalkyl halide having 3 carbon atoms, and
wherein a temperature T (° C.) inside the first flow path of the microreactor into which the fluoroalkylhalide and the organolithium compound have been introduced and a residence time t (sec) thereof in the first flow path of the microreactor satisfy the following relation: T≦−3.2t−45.

5. The method according to claim 1 , wherein the fluoroalkylhalide is a fluoroalkyl halide having 4 carbon atoms, and
wherein a temperature T (° C.) inside the first flow path of the microreactor into which the fluoroalkylhalide and the organolithium compound have been introduced and a residence time t (sec) thereof in the first flow path of the microreactor satisfy the following relation: T≦−5.1t−47.

6. The method according to claim 1 , wherein the fluoroalkylhalide is a fluoroalkyl halide having 5 carbon atoms, and
wherein a temperature T (° C.) inside the first flow path of the microreactor into which the fluoroalkylhalide and the organolithium compound have been introduced and a residence time t (sec) thereof in the first flow path of the microreactor satisfy the following relation: T≦−7.1t−47.

7. The method according to claim 1 , further comprising continuously introducing, into a third flow of the microreactor, the fluorine-containing substituted compound and methanol.

8. The method according to claim 1 , wherein the fluoroalkylhalide, the organolithium compound and the electrophile are dissolved in diethyl ether and introduced into the second path of the microreactor.

9. The method according to claim 1 , wherein the fluoroalkylhalide is a perfluoroalkyl halide.

10. The method according to claim 1 , wherein the organolithium compound is butyllithium.

11. The method according to claim 1 , wherein the electrophile is an aldehyde, a ketone or an isocyanate, or any combination thereof.

12. A method for producing a fluorine-containing substituted compound, the method comprising: introducing, into a microreactor provided with a flow path capable of mixing a plurality of liquids, an organofluorine compound, an organolithium compound, and an electrophile exhibiting electrophilic effect on a reaction product between the organofluorine compound and the organolithium compound, under conditions of temperature being −55° C. or higher.

13. The method according to claim 12 , wherein the temperature is −20° C. or higher.

14. The method according to claim 12 , wherein the temperature is 0° C. or higher.

15. The method according to claim 12 , further comprising continuously introducing, into the microreactor, the fluorine-containing substituted compound and methanol.

16. The method according to claim 12 , wherein the organofluorine compound, the organolithium compound and the electrophile are dissolved in diethyl ether and introduced into the microreactor.

17. The method according to claim 12 , wherein the organofluorine compound is a perfluoroalkyl halide.

18. The method according to claim 12 , wherein the organolithium compound is butyllithium.

19. The method according to claim 12 , wherein the electrophile is an aldehyde, a ketone or an isocyanate, or any combination thereof.

Assignees

• Univ Kyoto
• Taiyo Nippon Sanso Corp

Inventors

• Yoshida Junichi
• Nagaki Aiichiro

Classifications

• C07F7/2208 Primary

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C07F7/0805

  comprising only Si, C or H atoms · CPC title

• C07F9/28 Primary

  with one or more P—C bonds · CPC title

• C07C49/80

  containing halogen · CPC title

• C07C29/62

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title