INTEGRATED PROCESS FOR THE PRODUCTION OF 1-CHLORO-3,3,3-TRIFLUOROPROPENE

• US 20150148570A1
• Filed: 01/30/2015
• Published: 05/28/2015
• Est. Priority Date: 05/19/2011
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Cottrell, Stephen A., Tung, Hsueh Sung, Pokrovski, Konstantin A.
• Granted Patent: US 9,682,905 B2
• Time in Patent Office: Days
• US Class Current: 570/135
• 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. The compound 1233zd, produced by the process steps of:

(a) reacting 240fa and HF in a reactor operating at high pressure to produce a product stream comprising 1233zd, HCl, HF, and other byproducts;

(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 purified 1233zd;

wherein 1233zd has a purity of 99.5% or greater, as measured using gas chromatography.

2. The compound of claim 1, containing less than 100 ppm of byproduct compounds selected from the group consisting of 241fa, 242fa, 243fa, and mixtures thereof.

3. The compound of claim 1, containing less than 100 ppm of unsaturated byproduct compounds selected from the group consisting of 1233xf, 1224 isomers, 1234 isomers and mixtures thereof.