IP Library Granted Patent US 10,233,137
Granted Patent B1
US 10,233,137 · App. 15/783,401 · Granted Mar 19, 2019

Method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf)

Inventors: Haiyou Wang (Amherst, NY); Terris Yang (East Amherst, NY)
Assignee: Honeywell International Inc.
C07C17/395
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 10,233,137
App. No.
15/783,401
Granted
Mar 19, 2019
Kind
B1
Abstract

A method for removing unsaturated halogen impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf) of the type that may otherwise be difficult to separate from HFO-1234yf due to the impurities having boiling points which are close to that of HFO-1234yf and/or the potential of one or more of the impurities to form azeotropic mixtures with HFO-1234yf. A HFO-1234yf stream including unsaturated halogenated impurities is first passed through a caustic scrubber and is then passed through an acid scrubber. In the caustic scrubber and acidic scrubber, undesirable impurities are removed, in particular, 3,3,3-trifluoropropene (1243zf), 1-chloro-1-fluoroethylene (1131a), vinyl chloride (1140), and/or 1-chloro-2-fluoroethylene (1131).

Claims (30)

1. A method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprising the steps of:

providing a stream of 1234yf containing at least one impurity selected from the group consisting of 3,3,3-trifluoropropene (1243zf), 1-chloro-1-fluoroethylene (1131a), vinyl chloride (1140), 1-chloro-2-fluoroethylene (1131), and combinations thereof; and

contacting the stream with an acidic scrubbing fluid in an acid scrubber.

2. The method of claim 1 , wherein the at least one impurity includes 1-chloro-1-fluoroethylene (1131a) and, after said contacting step, an amount of 1131a in the stream is reduced by at least 5 wt. % relative to an amount of 1131a originally present in the stream.

3. The method of claim 1 , wherein the at least one impurity includes vinyl chloride (1140) and, after said contacting step, an amount of 1140 in the stream is reduced by at least 5 wt. % relative to an amount of 1140 originally present in the stream.

4. The method of claim 1 , wherein the at least one impurity includes 1-chloro-2-fluoroethylene (1131) and, after said contacting step, an amount of 1131 in the stream is reduced by at least 5 wt. % relative to an amount of 1131 originally present in the stream.

5. The method of claim 1 , wherein the acidic scrubbing fluid is sulfuric acid having a concentration between 88 wt. % and 99 wt. %.

6. The method of claim 1 , wherein at least one of the following conditions are present within the acid scrubber:

a temperature between 0° C. and 70° C.; and

a contact time between the vapor stream and acidic scrubbing fluid of between 0.1 second and 200 seconds.

7. The method of claim 1 , further comprising the additional step, prior to said contacting step, of contacting the stream with a basic scrubbing fluid in a caustic scrubber.

8. The method of claim 7 , wherein the at least one impurity includes 3,3,3-trifluoropropene (1243zf) and, after said contacting step, an amount of 1243zf in the stream is reduced by at least 5 wt. % relative to an amount of 1243zf originally present in the stream.

9. A method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprising the steps of:

providing a stream of 1234yf containing at least one impurity selected from the group consisting of 3,3,3-trifluoropropene (1243zf), 1-chloro-1-fluoroethylene (1131a), vinyl chloride (1140), 1-chloro-2-fluoroethylene (1131), and combinations thereof;

contacting the stream with a basic scrubbing fluid in a caustic scrubber; and

thereafter, contacting the stream with an acidic scrubbing fluid in an acid scrubber.

10. The method of claim 9 , wherein the at least one impurity includes 3,3,3-trifluoropropene (1243zf) and, after said contacting step, an amount of 1243zf in the stream is reduced by at least 5 wt. % relative to an amount of 1243zf originally present in the stream.

11. The method of claim 9 , wherein the at least one impurity includes 1-chloro-1-fluoroethylene (1131a) and, after said contacting step, an amount of 1131a in the stream is reduced by at least 5 wt. % relative to an amount of 1131a originally present in the stream.

12. The method of claim 9 , wherein the at least one impurity includes vinyl chloride (1140) and, after said contacting step, an amount of 1140 in the stream is reduced by at least 5 wt. % relative to an amount of 1140 originally present in the stream.

13. The method of claim 9 , wherein the at least one impurity includes 1-chloro-2-fluoroethylene (1131) and, after said contacting step, an amount of 1131 in the stream is reduced by at least 5 wt. % relative to an amount of 1131 originally present in the stream.

14. The method of claim 9 , wherein the acidic scrubbing fluid is sulfuric acid having a concentration between 88 wt. % and 99 wt. %.

15. The method of claim 9 , wherein at least one of the following conditions are present within the acid scrubber:

a temperature between 0° C. and 70° C.; and

a contact time between the vapor stream and acidic scrubbing fluid of between 0.1 second and 200 seconds.

16. The method of claim 1 , wherein the following conditions are present within the acid scrubber:

a temperature between 20° C. and 30° C.; and

a contact time between the vapor stream and acidic scrubbing fluid of between 5 seconds and 50 seconds.

17. The method of claim 9 , wherein the following conditions are present within the acid scrubber:

a temperature between 20° C. and 30° C.; and

a contact time between the vapor stream and acidic scrubbing fluid of between 5 seconds and 50 seconds.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074343/0989 →
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 13, 2017
From: WANG, HAIYOU; YANG, TERRIS
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 043861/0475 →