Method of producing hydrochlorofluoroolefin and method of producing 2,3,3,3-tetrafluoropropene
There is provided an industrially advantageous and efficient method of producing a Z-isomer of HCFO-1224yd or HCFO-1223xd by isomerizing an E-isomer thereof. The method produces HCFO (Z-isomer) by causing specific HCFO (E-isomer) contained in a raw material composition to undergo an isomerization reaction under a condition where the HCFO (E-isomer) is isomerized.
1. A method for producing a hydrochlorofluoroolefin, the method comprising isomerizing a compound of formula (1) contained in a raw material composition, to obtain a compound of formula (2):
wherein:
X represents a fluorine atom; and
the isomerizing comprises contacting the compound of formula (1) with a metal catalyst at a contact temperature of not lower than 150° C. and not higher than 350° C.
2. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the metal catalyst is at least one selected from a group consisting of a metal simple substance, a metal oxide, and a metal halide.
3. The method of producing hydrochlorofluoroolefin according to claim 1 , wherein the metal catalyst comprises at least one metal element selected from a group consisting of a group 4 metal element, a group 6 metal element, a group 8 metal element, a group 9 metal element, a group 10 metal element, a group 11 metal element, a group 12 metal element, and a group 13 metal element.
4. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the metal catalyst is a metal oxide.
5. The method of producing hydrochlorofluoroolefin according to claim 1 , wherein the metal catalyst is at least one selected from a group consisting of aluminum oxide and chromium oxide.
6. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein:
the raw material composition comprises the compound of formula (1) and the compound of formula (2); and
a molar ratio of the compound of formula (1) to the compound of formula (2) in the raw material composition is 5/95 or more.
7. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the isomerizing occurs in a vapor phase.
8. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the contact temperature of the compound of formula (1) and the metal catalyst ranges from 150° C. to 250° C.
9. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein a contact time of the compound of formula (1) with the metal catalyst ranges from 0.1 seconds to 1000 seconds.
10. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein, after the isomerizing, a product composition comprises the compound of formula (1) and the compound of formula (2).
11. The method of producing the hydrochlorofluoroolefin according to claim 10 , wherein, before the isomerizing, the raw material composition comprises the compound of formula (2).
12. A method of producing 2,3,3,3-tetrafluoropropene, the method comprising hydrogen-reducing the compound of formula (2) obtained in the method of claim 1 , to obtain the 2,3,3,3-tetrafluoropropene.
13. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the isomerizing comprises contacting the compound of formula (1) with a metal catalyst at a contact temperature of not lower than 150° C. and less than 250° C.
14. The method of producing the hydrochlorofluoroolefin according to claim 9 , wherein the contact time ranges from 24.7 seconds to 1000 seconds.
15. The method of producing the hydrochlorofluoroolefin according to claim 1 , wherein the metal catalyst comprises at least one metal element selected from a group consisting of a group 4 metal element, a group 6 metal element, a group 8 metal element, a group 9 metal element, a group 10 metal element, a group 12 metal element, and a group 13 metal element.