IP Library Granted Patent US 11,472,757
Granted Patent B2
US 11,472,757 · App. 16/757,825 · Granted Oct 18, 2022

Process for catalytic conversion of mixtures of HCFO-1233zd(Z) and HCFC-244fa into HCFO-1233zd(E)

Inventors: Christian Jungong (Morris Plains, NJ); Daniel C. Merkel (Morris Plains, NJ)
Assignee: Honeywell International Inc.
C07C17/358C07C17/25C07C17/383C07B2200/09
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,472,757
App. No.
16/757,825
Granted
Oct 18, 2022
Kind
B2
Abstract

A method for conversion of a composition containing HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E) by reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E). The catalyst may be a chromium-based catalyst such as chromium trifluoride, chromium oxyfluoride, or chromium oxide, for example.

Claims (28)

1. A method for simultaneous conversion of a mixture of HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E), comprising the steps of:

providing a mixture including HCFO-1233zd(Z) and HCFC-244fa; and

reacting the HCFO-1233zd(Z) and HCFC-244fa mixture in a vapor phase in the presence of a chromium oxyfluoride catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCF-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E), wherein said reacting step is conducted at a temperature between 200° C. and 250° C.

2. The method of claim 1 , wherein said reacting step is conducted at a temperature between 200° C. and 230° C.

3. The method of claim 1 , wherein a contact time between the composition and the catalyst is between 1 second and 150 seconds.

4. The method of claim 1 , wherein a pressure in the reactor is between 0 psig and 100 psig.

5. The method of claim 1 , wherein during the reacting step, the reactor includes less than 50 ppm water.

6. The method of claim 1 , wherein in the providing step, total impurities are present in an amount less than 10 wt. %, based on the total weight of the composition.

7. The method of claim 1 , wherein in the providing step, any compounds other than HCFO-1233zd(Z) and HCFC-244fa are present in an amount less than 6 wt. %, based on the total weight of the composition.

8. The method of claim 1 , wherein in the providing step, any compounds other than HCFO-1233zd(Z) and HCFC-244fa are present in an amount less than 1.5 wt. %, based on the total weight of the composition.

9. The method of claim 1 , wherein said reacting step achieves a conversion of HCFO-1233zd(Z) to HCFO-1233zd(E) between 88% and 96%.

10. The method of claim 1 , wherein said reacting step achieves a selectivity to HCFO-1233zd(E) between 90% and 97%.

11. The method of claim 1 , further comprising, after the reacting step, the additional steps of:

distilling the composition in a distillation column;

removing an overhead stream from the distillation column, the overhead stream concentrated in HCFO-1233zd(E); and

removing a bottoms stream from the distillation column, the bottoms stream concentrated in HCFO-1233zd(Z) and HCFC-244fa.

12. The method of claim 1 , further comprising, after the reacting step, the additional steps of:

distilling the composition in a distillation column;

removing an overhead stream from the distillation column, the overhead stream concentrated in HCFO-1233zd(E);

removing a bottoms stream from the distillation column, the bottoms stream concentrated in HCFO-1233zd(Z) and HCFC-244fa, and

recycling the bottoms stream back to the reactor.

13. A method for simultaneous conversion of a mixture of HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E), comprising the steps of:

providing a mixture including HCFO-1233zd(Z) and HCFC-244fa; and

reacting the HCFO-1233zd(Z) and HCFC-244fa mixture in a vapor phase in the presence of a catalyst selected from the group consisting of chromium trifluoride (CrF 3 ), chromium oxide (Cr 2 O 3 ), and chromium oxyfluoride, and combinations thereof, to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E); wherein said reacting step achieves a selectivity to HCFO-1233zd(E) between 90% and 97%, and wherein said reacting step is conducted at a temperature between 100° C. and 275° C.

14. The method of claim 13 , wherein said reacting step is conducted at a temperature between 200° C. and 250° C.

15. The method of claim 13 , wherein said reacting step is conducted at a temperature between 200° C. and 230° C.

16. The method of claim 13 , wherein said reacting step achieves a selectivity to HCFO-1233zd(E) between 92% and 97%.

17. The method of claim 1 , wherein said reacting step achieves a conversion of HCFC-244fa to HCFO-1233zd(E) between 90% and 99%.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074344/0054 →
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 Aug 4, 2021
From: JUNGONG, CHRISTIAN; MERKEL, DANIEL C.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 057078/0533 →