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

• US 9,682,905 B2
• Filed: 01/30/2015
• Issued: 06/20/2017
• Est. Priority Date: 05/19/2011
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Tung, Hsueh Sung, Pokrovski, Konstantin A., Cottrell, Stephen A.
• Primary Examiner(s): BAHTA, MEDHANIT W
• Application Number:
  US14/609,471
• Publication Number:
  US 20150148570A1
• Time in Patent Office: 872 Days
• CPC Class Codes: C07C 17/206 the other compound being HX
• CPC Class Codes: C07C 17/25 by splitting-off hydrogen halides from halogenated hydrocarbons
• CPC Class Codes: C07C 17/38 Separation; Purification; Stabilisation; Use of additives
• CPC Class Codes: C07C 17/383 by distillation
• CPC Class Codes: C07C 21/18 containing fluorine
• CPC Class Codes: Y02P 20/10 Process efficiency

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.

Claims

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.