IP Library Granted Patent US 10,005,704
Granted Patent B2
US 10,005,704 · App. 14/604,867 · Granted Jun 26, 2018

Method for prolonging a catalyst's life during hydrofluorination

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Quick Facts
Patent No.
US 10,005,704
App. No.
14/604,867
Granted
Jun 26, 2018
Kind
B2
Abstract

The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3, -trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).

Claims (13)

1. A process for the production of 2,3,3,3-tetrafluoropropene comprising:

(i) fluorination of a starting material comprising 1,1,2,3-tetrachloropropene and/or 1,1,1,2,3-pentachloropropane with hydrogen fluoride to produce an intermediate stream comprising 2-chloro-3,3,3-trifluoropropene and 2,3-dichloro-3,3-difluoropropene;

(ii) purifying the intermediate stream comprising 2-chloro-3,3,3-trifluoropropene to produce a feed stream comprising at least 99% by weight of 2-chloro-3,3,3-trifluoropropene based on the organics in the feed stream;

(iii) reacting the feed stream comprising at least 99% by weight of 2-chloro-3,3,3-trifluoropropene based on the organics in the feed stream with hydrogen fluoride and a fluorination catalyst in the absence of an oxidizing agent to produce 2-chloro-1,1,1,2-tetrafluoropropane; and

(iv) dehydrohalogenating the 2-chloro-1,1,1,2-tetrafluoropropane under conditions effective to produce 2,3,3,3-tetrafluoropropene.

2. The process of claim 1 wherein the feed stream is produced by a process comprising fluorinating 1,1,2,3,-tetrachloropropene and/or 1,1,1,2,3-tetrachloropropane and separating 2-chloro-3,3,3-trifluoropropene from an intermediate stream comprising 2-chloro-3,3,3-trifluoropropene and one or more impurities.

3. The process of claim 2 wherein said at least one impurity is 2,3-dichloro-3,3-trifluoropropene.

4. The process of claim 2 wherein the step of separating 2-chloro-3,3,3-trifluoropropene from one or more impurities is performed by distillation.

5. A process for producing 2,3,3,3-tetrafluoropropene comprising

(i) fluorinating 1,1,2,3,-tetrachloropropene and/or 1,1,1,2,3-tetrachloropropane to produce an intermediate stream comprising 2-chloro-3,3,3-trifluoropropene and 2,3-dichloro-3,3-difluoropropene;

(ii) separating 2-chloro-3,3,3-trifluoropropene from the intermediate stream by distillation to form a feed stream comprising at least about 99% by weight of organics of 2-chloro-3,3,3-trifluoropropene;

(iii) reacting said feed stream with hydrogen fluoride and a fluorination catalyst in the absence of an oxidizing agent to produce 2-chloro-1,1,1,2-tetrafluoropropane; and

(iv) dehydrohalogenating the 2-chloro-1,1,1,2-tetrafluoropropane under conditions effective to produce 2,3,3,3-tetrafluoropropene.

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 Mar 14, 2025
From: JOHNSON, ROBERT C.; MERKEL, DANIEL C.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070510/0976 →