Method of producing hydrochlorofluoroolefin and method of producing 2,3,3,3-tetrafluoropropene

Patent metadata

Field	Value
Publication number	US-10442744-B2
Application number	US-201715856999-A
Country	US
Kind code	B2
Filing date	Dec 28, 2017
Priority date	Jun 30, 2015
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Agc Inc

Inventors

• Takeuchi Yu
• Okamoto Hidekazu

Classifications

• C07B61/00

  Other general methods · CPC title

• B01J23/26

  Chromium · CPC title

• B01J23/44

  Palladium · CPC title

• C07C17/358 Primary

  by isomerisation · CPC title

• B01J21/06

  Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof · CPC title