IP Library Granted Patent US 8,680,345
Granted Patent B2
US 8,680,345 · App. 13/313,085 · Granted Mar 25, 2014

Low temperature production of 2-chloro-3,3,3-trifluoropropene

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Quick Facts
Patent No.
US 8,680,345
App. No.
13/313,085
Granted
Mar 25, 2014
Kind
B2
Abstract

Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.

Claims (20)

1. A method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst;

wherein the low temperature of the liquid phase reaction is a temperature range of 65° C. to 175° C.; and

wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.

2. The method of claim 1 , wherein the low temperature of the liquid phase reaction is a temperature range of 85° C. to 155° C.

3. The method of claim 1 , wherein the low temperature of the liquid phase reaction is a temperature range of 95° C. to 150° C.

4. A method for producing 1233xf comprising the steps of:

(a) providing a liquid reaction admixture comprising hydrogen fluoride and 1,1,1,2,3-pentachloropropane, wherein said hydrogen fluoride and 1,1,1,2,3-pentachloropropane are present in a molar ratio of greater than about 3:1 and

(b) reacting said hydrogen fluoride and 1,1,1,2,3-pentachloropropane in a liquid phase and at a reaction temperature of from about 65° C. to about 175° C. using one or more reactors in series to produce reaction product streams comprising 2-chloro-3,3,3-trifluoropropene, hydrogen chloride, unreacted hydrogen fluoride, and optionally unreacted 1,1,1,2,3-pentachloropropane.

5. The method of claim 4 , wherein the reaction temperature range is from 85° C. to 155° C.

6. The method of claim 4 , wherein the reaction temperature range is from 95° C. to 150° C.

7. The method of claim 4 , further comprising the steps;

(c) contacting said combined reaction product streams with a heat exchanger to produce:

(i) a first crude product stream comprising a majority of said hydrogen chloride, a majority of said 2-chloro-3,3,3-trifluoropropene, and at least a portion of said unreacted hydrogen fluoride, wherein said portion is an amount sufficient to at least form an azeotrope with one or more of said 2-chloro-3,3,3-trifluoropropene, and

(ii) a reflux component comprising a majority of said unreacted hydrogen fluoride and under-fluorinated intermediates; and

(d) returning said reflux component to said reaction admixture.

8. The method of claim 7 , further comprising one or more of the following steps:

(e) separating unreacted reactants, including unreacted 1,1,1,2,3-pentachloropropane and/or under-fluorinated intermediates via distillation and recycling these unreacted reactants and under-fluorinated intermediates back to the reactor;

(f) removing at least a portion, and preferably a majority, of hydrochloric acid by-product;

(g) separating and recycling unreacted HF in a crude product stream via a sulfuric acid adsorption or a phase separation; and

(h) distillation of the crude product stream to separate 1233xf from reaction by-products.

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 Dec 7, 2011
From: MERKEL, DANIEL C.; TUNG, HSUEH SUNG; POKROVSKI, KONSTANTIN A.; WANG, HAIYOU; BEKTESVIC, SELMA
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 027341/0921 →