Integrated process for the production of 1-chloro-3,3,3-trifluoropropene

Patent metadata

Field	Value
Publication number	US-9682905-B2
Application number	US-201514609471-A
Country	US
Kind code	B2
Filing date	Jan 30, 2015
Priority date	May 19, 2011
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.

First claim

What is claimed is:

1. A mixture comprising the compound 1-chloro-3,3,3-trifluoropropene (1233zd), and further comprising one or more saturated byproduct compounds selected from the group consisting of 1,1,3,3-tetrachloro-1-fluoropropane (241fa), 1,3,3-trichloro-1,1-difluoropropane (242fa), 1,1,1-trifluoro-3,3-dichloropropane (243fa), and mixtures thereof, said byproducts being present in the mixture at an amount that is under 100 ppm;
wherein the 1233zd mixture is produced by the process steps of:
(a) reacting 1,1,1,3,3-pentachloropropane (240fa) and HF in a reactor operating at a pressure of from 150 psig to 600 psig to produce a product stream comprising 1233zd, HCl and HF;
(b) distilling the product stream from step (a) into a first overhead product and a first bottoms product rich in HF;
(c) distilling the first overhead product from step (b) to form a second overhead product containing HCl and a second bottoms product containing organic components and HF;
(d) phase separating the second bottoms product from step (c) to separate the HF from the organic components; and
(e) caustic scrubbing, drying, and distilling the organic components from step (d) to provide the mixture including byproducts and 1233zd; and
wherein the compound 1233zd in the mixture has a purity of 99.5% or greater, as measured using gas chromatography.

2. The mixture of claim 1 , wherein the byproduct compound comprises 241fa.

3. The mixture of claim 1 , wherein the byproduct compound comprises 242fa.

4. The mixture of claim 1 , wherein the byproduct compound comprises 243fa.

5. A mixture comprising the compound 1-chloro-3,3,3-trifluoropropene (1233zd), and further comprising one or more unsaturated byproduct compounds selected from the group consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoropropene (1224) isomers, tetrafluoropropene (1234) isomers and mixtures thereof, said byproducts being present in the mixture at an amount that is no greater than 100 ppm;
wherein the 1233zd mixture is produced by the process steps of:
(a) reacting 1,1,1,3,3-pentachloropropane (240fa) and HF in a reactor operating at a pressure of from 150 psig to 600 psig to produce a product stream comprising 1233zd, HCl and HF;
(b) distilling the product stream from step (a) into a first overhead product and a first bottoms product rich in HF;
(c) distilling the first overhead product from step (b) to form a second overhead product containing HCl and a second bottoms product containing organic components and HF;
(d) phase separating the second bottoms product from step (c) to separate the HF from the organic components; and
(e) caustic scrubbing, drying, and distilling the organic components from step (d) to provide the mixture of byproducts and 1233zd; and
wherein the compound 1233zd in the mixture has a purity of 99.5% or greater, as measured using gas chromatography.

6. The mixture of claim 5 , wherein the byproduct compound comprises 1233xf.

7. The mixture of claim 5 , wherein the byproduct compound comprises 1224 isomers.

8. The mixture of claim 5 , wherein the byproduct compound comprises 1234 isomers.

Assignees

• Honeywell Int Inc

Inventors

• Cottrell Stephen A
• Tung Hsueh Sung
• Pokrovski Konstantin A

Classifications

• Y02P20/125

  Cross-Sectional Technologies · mapped topic

• C07C21/18

  containing fluorine · CPC title

• C07C17/38

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

• C07C17/25

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

• C07C17/206

  the other compound being HX · CPC title