E-1-chloro-3,3,3-trifluoropropene production process from 1,1,3,3-tetrachloropropene

Patent metadata

Field	Value
Publication number	US-9834499-B2
Application number	US-201614987347-A
Country	US
Kind code	B2
Filing date	Jan 4, 2016
Priority date	Jan 13, 2014
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

A production process for the production of E-1-chloro-3,3,3-trifluoropropene, the process including at least one stage during which 1,3,3,3-tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase, in the absence of a catalyst, with an HF/1,1,3,3-tetrachloropropene molar ratio between 3 and 20 inclusive, at a temperature between 50° C. and 150° C. inclusive and an absolute pressure of between 1 and 20 bar inclusive.

First claim

The invention claimed is:

1. A production process for the production of E-1-chloro-3,3,3-trifluoropropene, the process comprising:
(i) at least one stage during which 1,1,3,3-tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase in a reactor equipped with a drain and an effluent outlet; wherein HF and recoverable organic compounds are collected in the reactor drain, treated by at least one of decantation and azeotropic distillation, and recycled back to the same reactor;
(ii) at least one stage for treating the effluent from the reactor in order to provide a flow A that comprises E-1-chloro-3,3,3-trifluoropropene, HCl, HF and Z-1-chloro-3,3,3-trifluoropropene and a flow B that comprises at least 50% HF in weight;
(iii) at least one stage for recovering the hydrochloric acid from flow A, the hydrochloric acid being in flow C and flow D that includes E-1-chloro-3,3,3-trifluoropropene, HCl, HF and Z-1-chloro-3,3,3-trifluoropropene;
(iv) at least one stage for purifying flow D from stage (iii) in order to purify the E-1233zd to a level higher than or equal to 98% in weight.

2. The production process of claim 1 , wherein before the purification stage (iv), the flow D from stage (iii) is subjected to at least one separation phase in order to provide a flow E that comprises at least 50% HF in weight that can be recycled to the reactor and a flow F that comprises E-1-chloro-3,3,3-trifluoropropene, HCl, HF and Z-1-chloro-3,3,3-trifluoropropene.

3. The production process of claim 2 , wherein the separation stage is by decantation, initiated at a temperature between −50° C. and 50° C.

4. The production process of claim 1 , wherein the treatment stage (ii) involves a reflux column, initiated at a temperature between 30° C. and 120° C. in order to provide the flow B which is recycled to the reactor.

5. The production process of claim 1 , wherein the recovery of HCl in stage (iii) is obtained using a distillation column equipped with a reboiler at the bottom and a reflux system at the top.

6. The production process of claim 5 , wherein the temperature at the bottom is between 20° C. and 110° C. and the temperature at the top is between −50 and 0° C.

7. The production process of claim 1 , wherein the purification stage (iv) comprises at least one distillation stage.

8. The production process of claim 1 , wherein, in the reactor, the HF/1,1,3,3-tetrachloropropene molar ratio is between 5 and 15.

9. The production process of claim 1 , wherein reaction temperature is between 80° C. and 120° C.

10. The production process of claim 1 , wherein the fluorination reaction is initiated at a pressure between 5 and 15 bar.

11. The production process of claim 1 , wherein the fluorination reaction is initiated in an unstirred reactor.

12. The production process of claim 1 , wherein 1,1,3,3-tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase in a single reactor equipped with a drain and an effluent outlet.

Assignees

• Arkema France

Inventors

• Pigamo Anne
• Wismer John
• Collier Bertrand
• Bonnet Philippe

Classifications

• C07C17/383

  by distillation · CPC title

• C07C17/206 Primary

  the other compound being HX · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07B2200/09

  Geometrical isomers · CPC title

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title