Method for producing alkane compound

Patent metadata

Field	Value
Publication number	US-12404223-B2
Application number	US-202217825504-A
Country	US
Kind code	B2
Filing date	May 26, 2022
Priority date	Nov 27, 2019
Publication date	Sep 2, 2025
Grant date	Sep 2, 2025

Abstract

In the presence of a catalyst and a cycloalkane compound represented by formula (3):

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are the same or different and each is a halogen atom, an alkyl group, or a fluoroalkyl group; an alkene compound represented by formula (2):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above; is reacted with a hydrogen-containing gas to hydrogenate the alkene compound represented by formula ( 2 ), whereby an alkane compound represented by R 1 CHX 1 CHX 2 R 2 , wherein X 1 and X 2 are the same or different and each is a halogen atom, and R 1 and R 2 are the same or different and each is an alkyl group or a fluoroalkyl group; can be synthesized in such a manner that (S),(R)-isomer, (R),(R)-isomer, and (S),(S)-isomer are co-produced.

First claim

The invention claimed is:

1. A method for producing an alkane compound represented by formula (1):
R 1 CHX 1 CHX 2 R 2   (1)

wherein X 1 and X 2 are the same or different and each is a fluorine atom, and R 1 and R 2 are the same or different and each is an alkyl group or a fluoroalkyl group; the method comprising:
(IIA) reacting, in the presence of a catalyst and a cycloalkane compound, an alkene compound and a hydrogen-containing gas to hydrogenate the alkene compound,
wherein the cycloalkane compound is represented by formula (3):

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are the same and each is a fluorine atom, or a fluoroalkyl group, and

wherein the alkene compound is represented by formula (2):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above.

2. The production method according to claim 1 , wherein the amount of the cycloalkane compound represented by formula (3) used in the hydrogenation step is 0.5 to 20 mol per mol of the alkene compound represented by formula (2).

3. The production method according to claim 1 , wherein the method comprises, before the hydrogenation step:
(IA) reacting a cycloalkane compound represented by formula (3):

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are as defined above; and an alkene compound represented by formula (4):

wherein X 1 and X 2 are as defined above, and X 3 and X 4 are the same or different and each is a fluorine atom; to obtain an alkene compound represented by formula (2):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above.

4. A method for producing an alkane compound represented by formula (1):
R 1 CHX 1 CHX 2 R 2   (1)

wherein X 1 and X 2 are the same or different and each is a fluorine atom, and R 1 and R 2 are the same or different and each is an alkyl group or a fluoroalkyl group; the method comprising:
(IB) reacting a cycloalkane compound represented by formula (3):

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are the same and each is a fluorine atom, or a fluoroalkyl group; and an alkene compound represented by formula (4):

wherein X 1 and X 2 are as defined above, and X 3 and X 4 are the same or different and each is a fluorine atom; to obtain a mixture comprising an alkene compound represented by formula (2):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above; and the cycloalkane compound represented by formula (3); and
(IIB) reacting the mixture obtained in step (IB) and a hydrogen-containing gas in the presence of a catalyst to hydrogenate the alkene compound represented by formula (2).

5. The production method according to claim 4 , wherein in the hydrogenation step, the cycloalkane compound represented by formula (3) used as a raw material in the mixture is contained in an amount of 0.5 to 20 mol per mol of the alkene compound represented by formula (2).

6. The production method according to claim 1 , wherein the hydrogenation step is performed in a gas phase.

7. The production method according to claim 1 , wherein the alkane compound represented by formula (1) to be produced comprises 3 alkane compounds represented by formulas (1A), (1B), and (1C):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above.

8. The production method according to claim 7 , wherein 20 to 80 mol % of the alkane compound represented by formula (1A), 10 to 40 mol % of the alkane compound represented by formula (1B), and 10 to 40 mol % of the alkane compound represented by formula (1C) are obtained based on the total amount of a product obtained by the hydrogenation step, which is taken as 100 mol %.

9. The production method according to claim 4 , wherein the hydrogenation step is performed in a gas phase.

10. The production method according to claim 4 , wherein the alkane compound represented by formula (1) to be produced comprises 3 alkane compounds represented by formulas (1A), (1B), and (1C):

wherein X 1 , X 2 , R 1 , and R 2 are as defined above.

11. The production method according to claim 10 , wherein 20 to 80 mol % of the alkane compound represented by formula (1A), 10 to 40 mol % of the alkane compound represented by formula (1B), and 10 to 40 mol % of the alkane compound represented by formula (1C) are obtained based on the total amount of a product obtained by the hydrogenation step, which is taken as 100 mol %.

Assignees

• Daikin Ind Ltd

Inventors

• Etou Yuusuke
• Nakamura Shingo

Classifications

• C07C19/08

  containing fluorine · CPC title

• C07C17/281

  of only one compound · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07C17/354 Primary

  by hydrogenation · CPC title

• C07B35/02 Primary

  Reduction · CPC title