IP Library Granted Patent US 12,180,132
Granted Patent B2
US 12,180,132 · App. 17/619,388 · Granted Dec 31, 2024

Compositions and methods for synthesis of 2,3-dichloro-1,1,1,2-tetrafluoropropane and 2,3,3,3-tetrafluoropropene

Inventor: Xuehui Sun (Kennett Square, PA)
Assignee: THE CHEMOURS COMPANY FC, LLC
C07C17/04C07C17/204C07C17/389C07C21/18C07C17/23
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Quick Facts
Patent No.
US 12,180,132
App. No.
17/619,388
Granted
Dec 31, 2024
Kind
B2
Abstract

A method of synthesizing 2,3,3,3-tetrafluoropropene (1234yf) from 2-chloro-3,3,3-trifluoropropene (1233xf). The 2-chloro-3,3,3-trifluoropropene (1233xf) is reacted in the vapor phase, in the presence of a catalyst, at a temperature and pressure sufficient to selectively convert the 2-chloro-3,3,3-trifluoropropene (1233xf) to 2,3,3,3-tetrafluoropropene (1234yf) without the use of antimony-based catalysts.

Claims (18)

1. A composition comprising:

(a) -1-chloro-2,3,3,3-tetrafluoropropene (1224 yd),

(b) at least one of 2,3,3,3-tetrafluoropropene (1234yf) and 1-chloro-trifluoropropyne,

(c) optionally 1,2-dichloro-3,3,3-trifluoropropene (1223xd), and

(d) at least one additional compound selected from 2-chloro-3,3,3-trifluoropropene (1233xf), 3,3,3-trifluoropropene (1243zf), 2-chloro-1,1,1,2 tetrafluoropropane (244bb), 2-bromo-3,3,3-trifluoropropene (1233xfB), 2,3-dichloro-1,1,1-trifluoropropane (243 db), 3,3,3-trifluoropropyne, 1-chloro-1,2,3,3,3-pentafluoropropene (1215yb), 2-chloro-1,3,3,3-tetrafluoropropene (1224xe), 3-chloro-1,1,1-trifluoropropane (253fb), 1,1,1,2-tetrafluoropropane (254eb), 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene (1214ya), 2,2-dichloro-1,1,1-trifluoroethane (123), and 2-chloro-1,1,1,2-tetrafluoroethane (124),

wherein the amount of 1-chloro-2,3,3,3-tetrafluoropropene (1224 yd) is greater than the amount of the at least 2,3,3,3-tetrafluoropropene (1234yf) and 1-chloro-trifluoropropyne, optional 1,2-dichloro-3,3,3-trifluoropropene (1223xd), and the at least one additional compound.

2. The composition of claim 1 wherein the amount of the at least one of 2,3,3,3-tetrafluoropropene (1234yf) and 1-chloro-trifluoropropyne, optional 1,2-dichloro-3,3,3-trifluoropropene (1223xd), and the at least one additional compound ranges from greater than 0 to about 8% by weight based on the total amount of the composition.

3. The composition of claim 1 wherein 1-chloro-trifluoropropyne is present.

4. The composition of claim 1 , comprising between greater than 0 and about 10 wt % 1,2-dichloro-3,3,3-trifluoropropene (1223xd) based on the total amount of the composition.

5. The composition of claim 1 wherein 2,3,3,3-tetrafluoropropene (1234yf) is present in an amount of between >0 and less than about 0.02% by weight, based on the total amount of the composition.

6. The composition of claim 1 wherein 2,3-dichloro-1,1,1-trifluoropropane (243 db) is present.

7. A composition comprising 1-chloro-2,3,3,3-tetrafluoropropene (1224 yd), 1-chloro-trifluoropropyne, and at least one additional compound selected from the group consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 2,3,3,3-tetrafluoropropene (1234yf), 3,3,3-trifluoropropene (1243zf), 2-chloro-1,1,1,2 tetrafluoropropane (244bb), (2-bromo-3,3,3-trifluoropropene (1233xfB), 2,3-dichloro-1,1,1-trifluoropropane (243 db), 3,3,3-trifluoropropyne, 1-chloro-1,2,3,3,3-pentafluoropropene (1215yb), 1,2-dichloro-3,3,3-trifluoropropene (1223xd), 2-chloro-1,3,3,3-tetrafluoropropene (1224xe), 3-chloro-1,1,1-trifluoropropane (253fb), 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene (1214ya), 2,2-dichloro-1,1,1-trifluoroethane (123), and 2-chloro-1,1,1,2-tetrafluoroethane (124).

8. A composition comprising 1-chloro-2,3,3,3-tetrafluoropropene (1224 yd),

(i) one of 1-chloro-trifluoropropyne and 1,2-dichloro-3,3,3-trifluoropropene (1223xd),

(ii) one of 2,3,3,3-tetrafluoropropene (1234yf) and 2-chloro-3,3,3-trifluoropropene (1233xf), and

(iii) at least one additional compound selected 2-bromo-3,3,3-trifluoropropene (1233xfB), 2,3-dichloro-1,1,1-trifluoropropane (243 db), 1-chloro-1,2,3,3,3-pentafluoropropene (1215yb), 2-chloro-1,3,3,3-tetrafluoropropene (1224xe), 3-chloro-1,1,1-trifluoropropane (253fb), 1,1,1,2 tetrafluoroprop-1-ene (254eb), 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene (1214ya), 2,2-dichloro-1,1,1-trifluoroethane (123), and 2-chloro-1,1,1,2-tetrafluoroethane (124).

9. The composition of claim 8 wherein 2,3-dichloro-1,1,1-trifluoropropane (243 db) is present.

10. The composition of claim 8 wherein at least two of 2-bromo-3,3,3-trifluoropropene (1233xfB), 2,3-dichloro-1,1,1-trifluoropropane (243 db), 1-chloro-1,2,3,3,3-pentafluoropropene (1215yb), 2-chloro-1,3,3,3-tetrafluoropropene (1224xe), 3-chloro-1,1,1-trifluoropropane (253fb), 1,1,1,2-tetrafluoropropane (254eb), 1,1-dichloro-2,3,3,3-tetrafluoroprop-1-ene (1214ya), 2,2-dichloro-1,1,1-trifluoroethane (123), and 2-chloro-[1,1,1,2-tetrafluoroethane (124) are present.

Assignments (2)
SECURITY INTEREST Recorded Mar 2, 2022
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 059552/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2021
From: SUN, XUEHUI
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 058398/0242 →