Method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze) from 1-chloro-3,3,3-trifluoropopene (HCFO-1233zd)

Patent metadata

Field	Value
Publication number	US-10450248-B2
Application number	US-201816177707-A
Country	US
Kind code	B2
Filing date	Nov 1, 2018
Priority date	Nov 22, 2017
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100° C. and 450° C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.

First claim

What is claimed is:

1. A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze), comprising the steps of:
providing a reactant composition including 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), wherein the reactant composition includes only HCFO-1233zd as a single reactant, the HCFO-1233zd having a purity of greater than 90 area % as determined by gas chromatography (GC); and
reacting the reactant composition in the presence of at least one catalyst selected from the group consisting of chromium oxyfluoride, chromium oxide, metal fluoride, and combinations thereof at catalyst in the vapor phase at an elevated temperature to produce a product composition including HFO-1234ze.

2. The method of claim 1 , the HCFO-1233zd has a purity of greater than 95 area % as determined by gas chromatography (GC).

3. The method of claim 1 , wherein the product composition also includes 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc).

4. The method of claim 1 , wherein the catalyst is chromium oxyfluoride, the chromium oxyfluoride selected from the group consisting of amorphous chromium oxyfluoride, crystalline chromium oxyfluoride, and combinations of the foregoing.

5. The method of claim 1 , wherein the reactant composition includes less than 0.5 wt. % hydrogen fluoride (HF).

6. The method of claim 1 , wherein the product composition includes less than 0.1 wt. % hydrogen fluoride (HF).

7. The method of claim 1 , wherein the elevated temperature is between 100° C. and 450° C.

8. A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze), comprising the steps of:
providing a reactant composition including 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), wherein the reactant composition includes no other source of fluorine; and
reacting the reactant composition in the presence of a chromium oxyfluoride catalyst in the vapor phase at a temperature between 100° C. and 450° C. to produce a product composition including HFO-1234ze, the product composition additionally including 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc).

9. The method of claim 8 , wherein the HCFO-1233zd has a purity of greater than 90 area % as determined by gas chromatography (GC).

10. The method of claim 8 , wherein the reactant composition includes less than 0.5 wt. % hydrogen fluoride (HF).

11. The method of claim 8 , wherein the product composition includes less than 0.1 wt. % hydrogen fluoride (HF).

12. A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze), comprising the steps of:
providing a reactant composition including (Z)1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(Z)) to a first reactor;
isomerizing the reactant composition in the first reactor in the presence of a chromium oxyfluoride catalyst in the vapor phase at a temperature between 100° C. and 450° C. to produce a first product composition including (E)1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E));
providing the first product composition to a second reactor; and
reacting the first product composition in the second reactor in the presence of a chromium oxyfluoride catalyst in the vapor phase at a temperature between 100° C. and 450° C. to produce a second product composition including HFO-1234ze.

13. The method of claim 12 , wherein the second product composition also includes 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc).

14. The method of claim 12 , wherein the reactant composition includes less than 0.5 wt. % hydrogen fluoride (HF).

15. The method of claim 12 , wherein each of the first and second product compositions include less than 0.1 wt. % hydrogen fluoride (HF).

Assignees

• Honeywell Int Inc

Inventors

• Jungong Christian
• Merkel Daniel C
• Wang Haiyou

Classifications

• C07C17/37

  by disproportionation of halogenated hydrocarbons · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/20 Primary

  of halogen atoms by other halogen atoms · CPC title

• C07C17/206

  the other compound being HX · CPC title

• C07C17/358

  by isomerisation · CPC title