US 12,139,445 B2
Method of producing hydrofluoroolefin
Takayuki Komatsu, Meguro-ku (JP); Tomoaki Takayama, Meguro-ku (JP); Satoshi Ariyama, Meguro-ku (JP); and Taku Yamada, Chiyoda-ku (JP)
Assigned to AGC Inc., Tokyo (JP)
Filed by AGC Inc., Tokyo (JP)
Filed on Mar. 1, 2022, as Appl. No. 17/652,954.
Application 17/652,954 is a continuation of application No. PCT/JP2020/032710, filed on Aug. 28, 2020.
Claims priority of application No. 2019-163339 (JP), filed on Sep. 6, 2019.
Prior Publication US 2022/0267236 A1, Aug. 25, 2022
Int. Cl. C07C 17/23 (2006.01); B01J 21/08 (2006.01); B01J 23/62 (2006.01); B01J 23/644 (2006.01)
CPC C07C 17/23 (2013.01) [B01J 21/08 (2013.01); B01J 23/62 (2013.01); B01J 23/626 (2013.01); B01J 23/628 (2013.01); B01J 23/6447 (2013.01)] 11 Claims
 
1. A method of producing a hydrofluoroolefin, comprising:
reacting a chlorofluoroolefin that is represented by following Formula (I) or following Formula (II) and that has 8 or less carbon atoms with a hydrogen molecule, in the presence of an intermetallic compound containing at least one first metal that is selected from the group consisting of palladium, platinum, rhodium, copper and iridium, and containing a second metal that is different from the first metal, to obtain a hydrofluoroolefin in which a hydrogen atom is substituted for at least a chlorine atom represented by Cl among chlorine atoms contained in Formula (I) or Formula (II):

OG Complex Work Unit Chemistry
wherein, in Formula (I), each of R1 to R3 independently represents a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl group that may be substituted with a fluorine atom or a chlorine atom, and at least one fluorine atom is included in Formula (I);

OG Complex Work Unit Chemistry
wherein, in Formula (II), each of R4 to R10 independently represents a hydrogen atom, a fluorine atom, a chlorine atom or an alkyl group that may be substituted with a fluorine atom or a chlorine atom, at least one fluorine atom is included in Formula (II), and n is an integer from 0 to 5.