Method for producing olefin containing chlorine and fluorine

Patent metadata

Field	Value
Publication number	US-10358400-B2
Application number	US-201715633435-A
Country	US
Kind code	B2
Filing date	Jun 26, 2017
Priority date	Dec 26, 2014
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method including reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15).

First claim

The invention claimed is:

1. A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method comprising:
reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15):

wherein [L] is a ligand;
M is molybdenum or tungsten and the metal catalyst has an imide ligand and a ligand including two coordinating oxygen atoms as the ligand [L];
A 1 to A 6 are each independently a functional group selected from the group consisting of functional group (i), functional group (ii), functional group (iii), and functional group (iv);
A 1 and A 2 may bond to each other to form a ring;
A 3 and A 4 may bond to each other to form a ring;
A 5 and A 6 may bond to each other to form a ring;
provided that in the case where one of A 1 or A 2 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv);
in the case where one of A 3 or A 4 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv); and
in the case where one of the A 5 or A 6 is a halogen atom, the other is a functional group selected from the group consisting of the functional group (i), the functional group (iii) and the functional group (iv); and
X 1 is a fluorine atom, and
X 2 is independently a functional group selected from the group consisting of the functional group (i), the functional group (ii), the functional group (v), and the functional group (vi);
provided that in the case where one of X 1 or X 2 is a fluorine atom, the other is a functional group selected from the group consisting of the functional group (i), a halogen atom except for a fluorine atom, the functional group (v) and the functional group (vi):
functional group (i): a hydrogen atom;
functional group (ii): a halogen atom;
functional group (iii): a monovalent hydrocarbon group having a carbon number of from 1 to 20;
functional group (iv): a monovalent hydrocarbon group having a carbon number of from 1 to 20 and containing one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom;
functional group (v): a functional group selected from the group consisting of an alkyl group having a carbon number of from 1 to 12, an alkoxy group having a carbon number of from 1 to 12, an acyl group having a carbon number of from 5 to 20, an aryloxy group having a carbon number of from 5 to 20, a (per)halogenated alkyl group having a carbon number of from 1 to 12, a (per)halogenated alkoxy group having a carbon number of from 1 to 12, a (per)halogenated aryl group having a carbon n her of from 5 to 20, and a (per)halogenated aryloxy group having a carbon number of from 5 to 20; and
functional group (vi): the functional group (v) containing one or more atoms selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom.

2. The production method according to claim 1 , comprising reacting at least one compound selected from the group consisting of 1,2-dichloro-1,2-difluoroethylene, and 1,3,3-trichloro-1,2,3-trifluoropropene with the olefin compound of formula (31).

3. The production method according to claim 1 , wherein the olefin compound of formula (31) is ethylene, a monosubstituted olefin, or a 1,2-disubstituted olefin.

4. The production method according to claim 1 , wherein in the olefin compound of formula (31), A 3 is a hydrogen atom and A 4 is a hydrogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and containing one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom.

5. The production method according to claim 1 , wherein the olefin compound of formula (31) is at least one olefin compound selected from olefin compounds represented by the following formulae:

wherein R is an alkyl group having a carbon number of from 1 to 12 or an alkyl group having a carbon number of from 1 to 12 and having an etheric oxygen atom between a carbon atom and a carbon atom, and Ar is an aryl group having a carbon number of from 5 to 12.

6. The production method according to claim 1 , wherein the olefin compound of formula (31) is an olefin compound having a heteroatom existing adjacent to a carbon atom of the olefin.

7. The production method according to claim 6 , wherein the heteroatom is an oxygen atom or a nitrogen atom.

8. The production method according to claim 1 , wherein the reacting forms at least one olefin compound selected from olefin compounds represented by the following formulae as the compound of formula (51) and the compound of formula (52):

wherein R is an alkyl group having a carbon number of from 1 to 12 or an alkyl group having a carbon number of from 1 to 12 and having an etheric oxygen atom between a carbon atom and a carbon atom, and Ar is an aryl group having a carbon number of from 5 to 12.

9. The production method according to claim 1 , wherein a temperature during the reacting is from 0 to 150° C.

10. The production method according to claim 1 , wherein the reacting is carried out in the absence of a solvent.

11. The production method according to claim 1 , wherein the compound of formula (31) is an alkyl vinyl ether.

12. The production method according to claim 1 , wherein the compound of formula (31) is at least one selected from the group consisting of dodecyl vinyl ether and butyl vinyl ether.

13. The production method according to claim 1 , wherein the compound of formula (31) is selected from the group consisting

14. The method according to claim 1 , wherein the compound of formula (21) is 1,2-dichloro-1,2-difluoroethylene.

15. The production method according to claim 1 , wherein the metal catalyst is

Assignees

• Agc Inc

Inventors

• Takahira Yusuke
• Jomuta Daisuke

Classifications

• C07D207/27

  with substituted hydrocarbon radicals directly attached to the ring nitrogen atom · CPC title

• B01J31/1805

  the ligands containing nitrogen · CPC title

• C07C17/361

  by reactions involving a decrease in the number of carbon atoms · CPC title

• C07C67/287 Primary

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

• C07B61/00

  Other general methods · CPC title