Method for producing olefin

1. A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51), a compound of formula (52), a compound of formula (53), and a compound of formula (54), 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;

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), functional group (iv) 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;

at least one of A 3 to A 6 is independently a functional group (viii);

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 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):

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): an optionally halogenated monovalent hydrocarbon group having a carbon number of from 1 to 20 and 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, wherein the heteroatom is optionally adjacent to a carbon atom of the olefin group of the olefin compound of formula (31);

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 aryl 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 number 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 , wherein in the olefin compound of formula (21) X 2 is a hydrogen atom, a halogen atom, an alkyl group having a carbon number of from 1 to 12 and containing one or more fluorine atoms, a (per)halogenated alkoxy group having a carbon number of from 1 to 12, or a (per)halogenated alkoxy group having a carbon number of from 1 to 12 and having an etheric oxygen atom between a carbon atom and a carbon atom.

3. The production method according to claim 1 , wherein the olefin compound of formula (21) is at least one olefin compound selected from olefin compounds of the following formulae:

wherein R F is a (per)halogenated alkyl group having a carbon number of from 1 to 12 or a (per)halogenated 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.

4. The production method according to claim 1 , wherein the metal catalyst has an imide ligand and a ligand including two coordinating oxygen atoms as a ligand [L].

5. The production method according to claim 1 , wherein the metal catalyst at the start of the reacting is at least one compound selected from compounds of the following formulae:

wherein [L] is a ligand and M is molybdenum or tungsten.

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

7. The production method according to claim 1 , wherein A 3 of the olefin compound of formula (31) 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.

8. The production method according to claim 1 , wherein the olefin compound of formula (31) is at least one olefin compound selected from olefin compounds of 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.

9. 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.

10. The production method according to claim 9 , wherein the heteroatom is an oxygen atom or a nitrogen atom.

11. The production method according to claim 1 , wherein the reacting forms at least one olefin compound of the formula (51), the formula (52), the formula (53), and the formula (54) of the following formula:

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.

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

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

14. The method according to claim 1 , wherein at least one of A 3 to A 6 is an alkoxy group.

15. The method according to claim 1 , wherein the compound of formula (31) is butylvinylether.

16. The method according to claim 1 , wherein the compound of formula (21) is tetrafluoroethylene.

17. The method according to claim 1 , wherein the at least one metal catalyst has at least one metal-alkoxy group.

18. The method according to claim 1 , wherein the at least one catalyst contains a metal-imide group.

19. The production method according to claim 1 , wherein the compound of formula (21) is at least one selected from the group consisting of chlorotrifluoroethylene, trifluoroethylene, and trifluoromethyl trifluoroethylene.

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