IP Library Granted Patent US 8,716,538
Granted Patent B2
US 8,716,538 · App. 13/957,560 · Granted May 6, 2014

Process for separating hydrogen fluoride from organic feedstocks

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Quick Facts
Patent No.
US 8,716,538
App. No.
13/957,560
Granted
May 6, 2014
Kind
B2
Abstract

Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.

Claims (14)

1. A process for producing 2,3,3,3-tetrafluoropropene comprising:

a. reacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride to produce a crude product stream comprising 2-chloro-1,1,1,2-tetrafluoropropane, hydrogen fluoride, and 2-chloro-3,3,3-trifluoropropene;

b. distilling said crude product stream to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride;

c. cooling said distillate stream to produce a first intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride;

d. distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a second intermediate composition rich in 2-chloro-1,1,1,2-tetrafluoropropane and substantially free of hydrogen fluoride; and

e. dehydrochlorinating at least a portion of 2-chloro-1,1,1,2-tetrafluoropropane in said second intermediate composition to produce a final product comprising 2,3,3,3-tetrafluoropropene.

2. The process of claim 1 wherein said cooling produces a first distillate stream having a temperature of about −30° C. to about +10° C.

3. The process of claim 2 wherein said second bottoms stream comprises at least about 80 weight percent of the combined mass of said 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene in said crude product stream.

4. The process of claim 1 wherein said crude product stream comprises about 60 to about 70 weight percent hydrogen fluoride.

5. The process of claim 1 wherein said first distillate stream comprises about 20 to about 30 weight percent hydrogen fluoride.

6. The process of claim 1 wherein said cooling produces a first distillate stream having a temperature of about −30° C. to about −10° C.

7. The process of claim 1 wherein said organic layer comprises less than about 5 weight percent hydrogen fluoride.

8. The process of claim 1 wherein said organic layer is separated from said acid layer prior to step (d).

9. The process of claim 1 wherein said second bottoms stream comprises at least about 80 weight percent of the combined mass of said 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene in said raw organic feedstock.

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 Aug 2, 2013
From: MERKEL, DANIEL C.; POKROVSKI, KONSTANTIN A.; TUNG, HSUEH SUNG
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 030930/0553 →