IP Library Granted Patent US 10,035,743
Granted Patent B1
US 10,035,743 · App. 15/797,015 · Granted Jul 31, 2018

Method for conversion of 1, 3, 3, 3-tetrafluoropropene (HFO-1234ze) to 1-chloro-3, 3, 3-trifluoropropene (HCFO-1233zd)

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Quick Facts
Patent No.
US 10,035,743
App. No.
15/797,015
Granted
Jul 31, 2018
Kind
B1
Abstract

A method for converting 1, 3, 3, 3-tetrafluoropropene (HFO-1234ze) to 1-chloro-3, 3, 3-trifluoropropene (HCFC-1233zd) with high selectivity and without significant formation of 1, 1, 1, 3, 3-pentafluoropropane (HFC-245fa), by reacting 1234ze and hydrogen chloride (HCl) in a gas phase using a ferric chloride (FeCl 3 ) catalyst or a ruthenium chloride (RuCl 3 ) catalyst.

Claims (23)

1. A method for converting 1,3,3,3-tetrafluoropropene (HFO-1234ze) to 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd), comprising the step of:

reacting HFO-1234ze with hydrogen chloride (HCl) in a gas phase in the presence of a catalyst selected from the group consisting of ferric chloride (FeCl 3 ) and ruthenium chloride (RuCl 3 ) to form a product composition comprising HCFC-1233zd, the product composition including less than 0.05 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition as determined by gas chromatography (GC).

2. The method of claim 1 , wherein the catalyst is ferric chloride (FeCl 3 ).

3. The method of claim 2 , wherein the product composition includes less than 0.001 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

4. The method of claim 2 , wherein the product composition includes no detectable amount of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

5. The method of claim 1 , wherein the catalyst is ruthenium chloride (RuCl 3 ).

6. The method of claim 5 , wherein the product composition includes less than 0.025 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

7. The method of claim 5 , wherein the product composition includes less than 0.001 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

8. The method of claim 5 , wherein the product composition includes no detectable amount of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition as determined by gas chromatography (GC).

9. The method of claim 1 , wherein the reacting step is carried out at a temperature between 250° C. and 400° C.

10. The method of claim 1 , wherein the reacting step is carried out at a temperature between 275° C. and 350° C.

11. The method of claim 1 , wherein the reacting step is carried out at a contact time of the HFO-1234ze and HCl to the catalyst of between 2 seconds and 30 seconds.

12. The method of claim 1 , wherein the reacting step is carried out at a contact time of the HFO-1234ze and HCl to the catalyst of between 5 seconds and 20 seconds.

13. The method of claim 1 , wherein the reacting step is conducted in a continuous manner.

14. The method of claim 1 , wherein the reacting step achieves a selectivity to HCFC-1233zd in the product composition of at least 95%.

15. A method for converting 1,3,3,3-tetrafluoropropene (HFO-1234ze) to 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd), comprising the step of:

reacting HFO-1234ze with hydrogen chloride (HCl) in a gas phase in the presence of a ferric chloride (FeCl 3 ) catalyst at a temperature between 250° C. and 400° C. to form a product composition comprising HCFC-1233zd, the product composition including less than 0.05 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition as determined by gas chromatography (GC).

16. The method of claim 15 , wherein the product composition includes less than 0.001 area percent of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

17. The method of claim 15 , wherein the product composition includes no detectable amount of 1,1,1,3,3-pentafluoropropane (HFC-245fa), based on the total area percent of the product composition, as determined by gas chromatography (GC).

18. The method of claim 15 , wherein the reacting step is carried out at a contact time of the HFO-1234ze and HCl to the catalyst of between 2 seconds and 30 seconds.

19. The method of claim 15 , wherein the reacting step achieves a selectivity to HCFC-1233zd in the product composition of at least 95%.

20. A method for converting 1,3,3,3-tetrafluoropropene (HFO-1234ze) to 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd), comprising the step of:

reacting HFO-1234ze with hydrogen chloride (HCl) in a gas phase in the presence of a catalyst selected from the group consisting of ferric chloride (FeCl 3 ) and ruthenium chloride (RuCl 3 ) to form a product composition comprising HCFC-1233zd, the product composition not including 1,1,1,3,3-pentafluoropropane (HFC-245fa).

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2017
From: NAIR, HARIDASAN K.; SINGH, RAJIV RATNA
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 043979/0541 →