# US 8,541,634 B2 · Azeotrope-like compositions of (Z)-1-chloro-3,3,3-trifluoropropene and hydrogen fluoride

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- Number: US 8,541,634 B2
- Document ID: US8541634B2
- Status: Granted
- Kind: B2
- Application number: 13/740,972
- Filed: 2013-01-14
- Published: 2013-05-23
- Granted: 2013-09-24
- Earliest claimed: 2010-12-03
- Assignees: Honeywell International Inc.
- Applicants: Honeywell International Inc.
- Inventors: Ryan Hulse; Hang T Pham
- Web page: https://patentgrep.com/patent/US8541634B2

## CPC

- C07C 17/38: Separation; Purification; Stabilisation; Use of additives
- A62D 1/0057: {Polyhaloalkanes (A62D1/005 takes precedence)}
- B01D 3/36: Azeotropic distillation
- C01B 7/191: {Hydrogen fluoride}
- C07C 21/18: containing fluorine
- C09K 3/30: for aerosols (aerosol containers B65D83/14)
- C09K 5/044: {comprising halogenated compounds}
- C11D 7/5045: {Mixtures of (hydro)chlorofluorocarbons}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A62D: CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.

## Claims

### Claim 1

A method of separating 1233zd(Z) from an azeotropic or azeotrope-like mixture, said mixture consists essentially of hydrogen fluoride and (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)), said mixture has a boiling point of from about 0° C. to about 60° C. at a pressure of from about 3 psia to about 73 psia, wherein the hydrogen fluoride is present in an amount of from about 20 to about 35 weight percent, said method comprising the step of extracting the HF from the mixture.

### Claim 2 (depends on 1)

The method of claim 1, wherein the extraction of HF is accomplished using an aqueous solution.

### Claim 3 (depends on 2)

The method of claim 2, wherein the aqueous solution is water.

### Claim 4 (depends on 1)

The method of claim 1, wherein the extraction of HF is accomplished using sulfuric acid.

### Claim 5 (depends on 1)

The method of claim 1, wherein the extraction of HF is accomplished by distillation.

### Claim 6 (depends on 5)

The method of claim 5, wherein the distillation comprises extractive distillation.

### Claim 7 (depends on 5)

The method of claim 5, wherein the distillation comprises pressure swing distillation.

### Claim 8 (depends on 1)

The method of claim 1, wherein the mixture comprises hydrogen fluoride in an amount of about 26±3 weight percent.