Method for producing fluorine-containing olefin

Patent metadata

Field	Value
Publication number	US-9796647-B2
Application number	US-201615385576-A
Country	US
Kind code	B2
Filing date	Dec 20, 2016
Priority date	Sep 6, 2013
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

A method for producing at least one compound selected from the group consisting of a compound represented by the following formula (10), a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13), which the method containing reacting a compound represented by the following formula (2) with a compound represented by the following formula (7), in the presence of at least one compound selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (3), a compound represented by the following formula (4), a compound represented by the following formula (8), and a compound represented by the following formula (9).

First claim

The invention claimed is:

1. A method comprising:
reacting a compound of formula (2) with a compound of formula (7), in the presence of at least one compound selected from the group consisting of a compound of formula (1), a compound of formula (3), a compound of formula (4), a compound of formula (8), and a compound of formula (9) to produce at least one compound selected from the group consisting of a compound of formula (10), a compound of formula (11), a compound of formula (12), and a compound of formula (13):

wherein:
[L] is a ligand;
A 1 to A 6 each independently is 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, in the case where one of A 1 and 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 and 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 A 5 and 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);
X 1 and X 2 each independently is a functional group selected from the group consisting of the functional group (i), the functional group (ii), the functional group (v), the functional group (vi) and the functional group (vii), wherein at least one of X 1 and X 2 is a halogen atom or a (per)halogenated alkyl group:
the functional group (i) is a hydrogen atom;
the functional group (ii) is a halogen atom;
the functional group (iii) is a monovalent hydrocarbon group having a carbon number of from 1 to 20;
the functional group (iv) is a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising 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;
the functional group (v) is 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 aryl group having a carbon number of from 5 to 20, an aryloxy group having a carbon number of from 5 to 20;
the functional group (vi) is a functional group (v) comprising 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; and
the functional group (vii) is a functional group selected from 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 number of from 5 to 20, and a (per)halogenated aryloxy group having a carbon number of from 5 to 20.

2. The method according to claim 1 , wherein the reacting is carried out with the compound of the formula (1) which is a ruthenium-carbene complex.

3. The method according to claim 1 , wherein one of A 1 and A 2 is a hydrogen atom, and the other is a functional group selected from the group consisting of the functional group (iii) and the functional group (iv).

4. The method according to claim 1 , wherein the compound of the formula (3) and the compound of the formula (4) are reaction products of the compound of the formula (1) with the compound of the formula (2).

5. The method according to claim 1 , wherein the compound of the formula (8) and the compound of the formula (9) are reaction products of the compound of the formula (3) or the compound of the formula (4) with the compound of the formula (7).

6. The method according to claim 1 , wherein, in the formula (2), X 1 is a fluorine atom and X 2 is a hydrogen atom, a fluorine atom, a chlorine atom, or a trifluoromethyl group.

7. The method according to claim 6 , wherein the compound of the formula (2) is tetrafluoroethylene.

8. The method according to claim 1 , wherein the compound of the formula (7) is at least one compound selected from the group consisting of ethylene, a monosubstituted olefin and a 1,2-disubstituted olefin.

9. The method according to claim 8 , wherein the compound of formula (7) is at least one compound selected from the group consisting of a monosubstituted olefin and a 1,2-disubstituted olefin selected from the group consisting of the functional group (iii) and the functional group (iv).

10. The method according to claim 1 , wherein the compound of the formula (7) is a compound comprising a hetero atom at the vinyl position thereof.

11. The method according to claim 1 , comprising bringing the compound of the formula (1) into contact with the compound of the formula (2) to thereby convert into at least one of the compound of the formula (3) and the compound of the formula (4), and then bringing the converted compound into contact with the compound of the formula (7).

12. The method according to claim 1 , comprising bringing at least one of the compound of the formula (3) and the compound of the formula (4) into contact with the compound of the formula (7) to thereby convert into at least one of the compound of the formula ( 8 ) and the compound of the formula (9), and then bringing the converted compound into contact with the compound of the formula (2).

13. The method according to claim 1 , comprising bringing at least one of the compound of the formula (8) and the compound of the formula (9) into contact with the compound of the formula (2) to thereby convert into at least one of the compound of the formula (3) and the compound of the formula (4), and then bringing the converted compound into contact with the compound of the formula (7).

14. The method according to claim 1 , wherein the compound of the formula (2) and the compound of the formula (7) are brought into contact with the compound of the formula (1) simultaneously.

15. The method according to claim 1 , wherein the reaction of the compound represented by formula (2) with the compound represented by formula (7) is a 1,1-difluoro-2-substituted olefin.

16. The method according to claim 1 , wherein the reacting is carried out in a solvent.

17. The method according to claim 1 , wherein at least one of A 1 and A 2 is a fluoroalkoxy group.

18. The method according to claim 1 , wherein at least one of A 1 and A 2 is of formula —CF—O—CF 2 CF(CF 3 )—O—CF 2 CF 2 CF 3 .

19. The method according to claim 1 , wherein the compound of formula (7) is and an alkyl vinyl ether.

20. The method according to claim 1 , wherein the compound of formula (7) is an alkoxy styrene.

21. The method according to claim 1 , wherein the compound of formula (7) is an alkyl vinyl ether having an alkyl group with from 4 to 12 carbon atoms.

22. The method according to claim 1 , wherein the compound of formula (2) is at least one selected from the group consisting of tetrafluoroethylene, trifluorochloroethylene, trifluorotrimethylfluoroethylene and trifluor

Assignees

• Asahi Glass Co Ltd

Inventors

• Takahira Yusuke

Classifications

• C07F15/0046

  Ruthenium compounds · CPC title

• C07C41/22

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

• C07C43/176

  having unsaturation outside the aromatic rings · CPC title

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• B01J31/2404

  Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring · CPC title