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

• US 9,556,091 B2
• Filed: 11/23/2015
• Issued: 01/31/2017
• 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.
• Primary Examiner(s): Parsa, Jafar
• Assistant Examiner(s): BAHTA, MEDHANIT W
• Application Number:
  US14/948,756
• Publication Number:
  US 20160083316A1
• Time in Patent Office: 435 Days
• US Class Current: 1/1
• 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 process for making highly purified 1-chloro- 3,3,3-trifluoropropene (HCFC-1233zd) by the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF in a reactor at a reactor pressure of from 150 psig to 600 psig wherein the purification of the HCFC-1233zd comprises the sequential steps of:

(a) distilling the resulting product stream comprising 1233zd, HCl, HF, and other byproducts are distilled and wherein the bottoms product, rich in HF, is recycled to the reactor;

(b) distilling the overhead product from the step (a) distillation column in is fed to a second distillation column to remove the HCl;

(c) scrubbing the HCI in the overhead stream of the step (b) distillation with water and recovering as an aqueous solution;

(d) phase separating the bottom stream from the step (b) distillation column to recover HF;

(e) recycling the HF rich top layer of the phase separation back to the reactor; and

(f) scrubbing, drying and distilling the phase separation bottom layer from step (d) to obtain the desired 1233zd at a purity of 99.5% or greater, as measured using gas chromatography.