IP Library › Granted Patent US 10,125,066
Granted Patent B1
US 10,125,066 · App. 15/825,334 · Granted Nov 13, 2018

Process for making high purity 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb)

Inventors: Christian Jungong (Depew, NY); Daniel C. Merkel (Orchard Park, NY)
Assignee: Honeywell International Inc.
C07C17/087B01J21/02B01J23/44C07C17/25C07C17/38C07C19/10C07C21/04C07C21/18
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Quick Facts
Patent No.
US 10,125,066
App. No.
15/825,334
Granted
Nov 13, 2018
Kind
B1
Abstract

A method for producing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from a reaction composition including a mixture of HCFC-244bb and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) by selectively hydrogenating the HCFO-1233xf component of the mixture in a vapor phase in the presence of hydrogen gas and a catalyst to generate a product composition including unreacted HCFC-244bb and hydrogenation products of HCFO-1233xf, such as 2-chloro-1,1,1-trifluoropropane (HCFC-253db), which may be separated from the HCFC-244bb by distillation. The separated HCFC-244bb may then be purified by subsequent acid neutralization and drying steps.

Claims (31)

1. A method for producing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), comprising the steps of:

providing a reactant stream including a mixture of HCFC-244bb and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), the amount of HCFO-1233xf between 5 wt. % and 25 wt. % based on a total weight of the reactant stream; and

hydrogenating the HCFO-1233xf of the reactant stream in a vapor phase in the presence of hydrogen gas and a palladium catalyst diluted in an alpha aluminum support to a palladium loading between 0.3 wt. % and 0.5 wt. %, based on the total weight of the palladium catalyst and the alpha aluminum support, to generate a product composition including unreacted HCFC-244bb and 2-chloro-1,1,1-trifluoropropane (HCFC-253db).

2. The method of claim 1 , wherein the reactant stream includes between 75 wt. % and 98 wt. % HCFC-244bb, based on the total weight of the reactant stream.

3. The method of claim 1 , wherein the hydrogenation step further comprises hydrogenating at a temperature between 100° C. and 250° C.

4. The method of claim 1 , wherein the hydrogenation step further comprises hydrogenating at a pressure between 5 psig and 100 psig.

5. The method of claim 1 , further comprising the additional step of separating the HCFC-244bb and the HCFC-253db.

6. The method of claim 5 , further comprising the additional steps of:

subjecting the separated HCFC-244bb to an acid neutralization step; and

drying the acid neutralized HCFC-244bb.

7. The method of claim 6 , wherein, following the drying step, the HCFC-244bb has at least one of:

a purity greater than 95 wt. %;

a water content less than 10 ppm; and

an acid content less than 1 ppm.

8. The method of claim 1 , wherein, in the hydrogenating step, conversion of HCFO-1233xf exceeds 98%.

9. The method of claim 1 , wherein, in the hydrogenating step, selectivity of HCFO-1233xf to HCFC-253db exceeds 60%.

10. A method for producing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), comprising the steps of:

providing a reactant stream including a mixture of HCFC-244bb and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), the amount of HCFO-1233xf between 5 wt. % and 25 wt. % based on a total weight of the reactant stream;

hydrogenating the HCFO-1233xf of the reactant stream in a vapor phase in the presence of hydrogen gas and a palladium metal catalyst diluted in an alpha aluminum support to a palladium loading between 0.3 wt. % and 0.5 wt. %, based on the total weight of the palladium catalyst and the alpha aluminum support, at a temperature between 100° C. and 250° C. to generate a product composition including unreacted HCFC-244bb and 2-chloro-1,1,1-trifluoropropane (HCFC-253db); and

separating the HCFC-244bb and the HCFC-253db.

11. The method of claim 10 , further comprising the additional steps of:

subjecting the separated HCFC-244bb to an acid neutralization step; and

drying the acid neutralized HCFC-244bb.

12. The method of claim 11 , wherein, following the drying step, the HCFC-244bb has a purity greater than 95 wt. %, a water content less than 10 ppm, and an acid content less than 1 ppm.

13. The method of claim 10 , wherein the reactant stream includes between 75 wt. % and 98 wt. % HCFC-244bb, based on the total weight of the reactant stream.

14. The method of claim 10 , wherein the hydrogenation step further comprises hydrogenating at a pressure between 5 psig and 100 psig.

15. The method of claim 10 , wherein, in the hydrogenating step, conversion of HCFO-1233xf exceeds 98%.

16. The method of claim 1 , wherein, in the providing step, the reactant stream is diluted by an inert diluent, the inert diluent present in the reactant stream in an amount between 2 wt. % and 25 wt. %, based on the total weight of the HCFO-1233xf and the HCFC-244bb in the reactant stream.

17. The method of claim 1 , wherein, in the hydrogenating step, the hydrogen gas is diluted by an inert diluent, the inert diluent present in the hydrogen gas in an amount between 2 wt. % and 40 wt. %, based on a total weight of the hydrogen gas.

18. The method of claim 10 , wherein, in the providing step, the reactant stream is diluted by an inert diluent, the inert diluent present in the reactant stream in an amount between 2 wt. % and 25 wt. %, based on the total weight of the HCFO-1233xf and the HCFC-244bb in the reactant stream.

19. The method of claim 10 , wherein, in the hydrogenating step, the hydrogen gas is diluted by an inert diluent, the inert diluent present in the hydrogen gas in an amount between 2 wt. % and 40 wt. %, based on a total weight of the hydrogen gas.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2017
From: JUNGONG, CHRISTIAN; MERKEL, DANIEL C.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 044246/0389 →
Cited By (2)
US 50,875 US 12,606,728