IP Library Granted Patent US 11,286,221
Granted Patent B2
US 11,286,221 · App. 17/251,328 · Granted Mar 29, 2022

Method for producing 1-chloro-3,3,3-trifluoropropene

Inventors: Kevin Hisler (Pierre-Benite, FR); Anne Pigamo (Pierre-Benite, FR); Laurent Wendlinger (Pierre-Benite, FR); Emmanuel Boussarie (Pierre-Benite, FR)
Assignee: ARKEMA FRANCE
C07C17/206C07C21/18
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Quick Facts
Patent No.
US 11,286,221
App. No.
17/251,328
Granted
Mar 29, 2022
Kind
B2
Abstract

The present invention relates to a process for producing 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), comprising: i) providing a stream A1 comprising HF, a stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene, and a reactor containing a liquid phase, ii) in said reactor, contacting, in said liquid phase, said stream A1 comprising HF with said stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene under conditions which are sufficient to produce a stream C comprising 1-chloro-3,3,3-trifluoropropene, HF and HCl, iii) recovering said stream C, characterized in that said reactor is provided with means for stirring said liquid phase so as to keep the temperature of said liquid phase substantially constant during step ii).

Claims (29)

1. A process for producing 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), comprising the steps of:

i) providing:

a stream A1 comprising HF,

a stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene, and

a reactor containing a liquid phase,

ii) in said reactor, contacting, in said liquid phase, said stream A1 comprising HF with said stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene under conditions which are sufficient to produce a stream C comprising 1-chloro-3,3,3-trifluoropropene, HF and HCl,

iii) recovering said stream C,

wherein said reactor is provided with means for stirring said liquid phase so as to keep the temperature of said liquid phase substantially constant during step ii) and

wherein said liquid phase in step ii) comprises less than 15% by weight of HF.

2. The process as claimed in claim 1 , wherein during the implementation of step ii), the temperature of said liquid phase varies by a maximum of 2° C.

3. The process as claimed in claim 1 , wherein said stirring means comprise a static mixer, a device for injecting an inert gas into said liquid phase, a device for recirculating the liquid phase, or a device for returning a flow of HF into said liquid phase.

4. The process as claimed in claim 1 , wherein the stirring means comprises a static mixer and the process comprises the steps of:

i) providing:

the stream A1 comprising HF,

the stream A2 comprising 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene, and

the reactor containing the liquid phase and comprising the static mixer,

i′) contacting said stream A1 with said stream A2 in said static mixer to form a mixture B comprising HF, 1,1,3,3-tetrachloropropene and/or 1,3,3,3-tetrachloropropene,

ii′) diffusing said mixture B into said liquid phase in order to carry out step ii) proceeding from this.

5. The process as claimed in claim 1 , wherein said stream A1 and said stream A2 are preheated before carrying out step ii).

6. The process as claimed in claim 1 , wherein step ii) is carried out at a temperature of between 20° C. and 150° C.

7. The process as claimed in claim 1 , wherein step ii) is carried out at a pressure of between 1 and 20 bara.

8. The process as claimed in claim 1 , wherein it is carried out in continuous mode in a single reactor.

9. The process as claimed in claim 1 , wherein step ii) is carried out in the absence of catalyst.

10. The process as claimed in claim 1 , wherein stream C is purified—to form a stream C1 comprising HCl and a stream C2 comprising 1-chloro-3,3,3-trifluoropropene and HF, said stream C2 itself being separated into a stream C3 comprising 1-chloro-3,3,3-trifluoropropene and a stream C4 predominantly comprising the HF recycled to step i′) or ii).

11. The process as claimed in claim 1 , wherein said liquid phase in step ii) comprises less than 10% by weight of HF.

12. The process as claimed in claim 1 , wherein stream C is a gaseous stream.

13. The process as claimed in claim 1 , wherein said liquid phase in step ii) comprises less than 6% by weight of HF.

14. The process as claimed in claim 1 , wherein said liquid phase in step ii) comprises less than 8% by weight of HF.

15. The process as claimed in claim 4 , wherein said stream A1 and said stream A2 are preheated before carrying out step i′).

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2020
From: HISLER, KEVIN; PIGAMO, ANNE; WENDLINGER, LAURENT; BOUSSARIE, EMMANUEL
To: ARKEMA FRANCE
Reel/Frame 054614/0718 →
Cited By (1)
US 12,391,634