# US 11,440,860 B2 · Dehydrohalogenation of hydrochlorofluorocarbons

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- Number: US 11,440,860 B2
- Document ID: US11440860B2
- Status: Granted
- Kind: B2
- Application number: 17/155,796
- Filed: 2021-01-22
- Published: 2021-05-13
- Granted: 2022-09-13
- Earliest claimed: 2015-09-11
- Assignees: The Chemours Company Fc, LLC
- Applicants: The Chemours Company Fc, LLC
- Inventors: Xuehui Sun; Karl Krause
- Web page: https://patentgrep.com/patent/US11440860B2

## CPC

- C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons
- C07C 21/18: containing fluorine
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A dehydrohalogenation product includes a hydrochlorofluorocarbon mixture of a fluoroolefin of formula RCX═CZQ and a halofluoroalkane of formula RCXYCZQT. R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen. One of Y and T is H and the other is Cl, Br, or I. About 80% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin. The dehydrohalogenation product also includes a caustic agent and a solvent. In some embodiments, the dehydrohalogenation product is free of any catalyst, including any phase transfer catalyst.

## Claims

### Claim 1

A composition comprising:
a hydrochlorofluorocarbon mixture comprising:
a fluoroolefin of formula RCX═CZQ, wherein R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen; and
a halofluoroalkane of formula RCXYCZQT, wherein one of Y and T is H and the other is Cl, Br, or I;
wherein about 80% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin;
a caustic agent; and
a solvent.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the composition is free of any catalyst, including any phase transfer catalyst.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the caustic agent is selected from the group consisting of NaOH, KOH, LiOH, CsOH, Ca(OH)2, Zn(OH)2, Na2CO3, K2CO3, K3PO4, Na3PO4, KF, and CsF.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the solvent is an aqueous solvent.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the aqueous solvent is water.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the halofluoroalkane is CF3CHClCH2Cl and the fluoroalkene is CF3CCl═CH2 or wherein the halofluoroalkane is CF3CH2CHCl2 and the fluoroalkene is CF3CH═CHCl or wherein the halofluoroalkane is CF3CCl2CH3 and the fluoroalkene is CF3CCl═CH2 or wherein the halofluoroalkane is CF3CHFCH2Cl and the fluoroalkene is CF3CF═CH2 or wherein the halofluoroalkane is CF3CClFCH3 and the fluoroalkene is CF3CF═CH2.

### Claim 7 (depends on 1)

The composition of claim 1, wherein one of Y and T is hydrogen and the other is chlorine.

### Claim 8 (depends on 1)

The composition of claim 1 further comprising an amine.

### Claim 9 (depends on 8)

The composition of claim 8, wherein the amine is present at a molar ratio in the range of about 0.05 to about 3 with respect to the caustic agent.

### Claim 10 (depends on 8)

The composition of claim 8, wherein the amine has the formula NR1R2R3 wherein R1, R2 and R3 are independently hydrogen, alkyl group, aryl, arylalkyl group, heterocyclic, heterocyclicalkyl, or N(R4)(R5)N(R6)(R7), wherein R4, R5, R6 and R7 are independently hydrogen, alkyl group, aryl, arylalkyl group, heterocyclic, or heterocyclicalkyl.

### Claim 11 (depends on 8)

The composition of claim 8, wherein the amine is triethylamine.

### Claim 12 (depends on 1)

The composition of claim 1 further comprising ammonia.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the halofluoroalkane is CF3CHClCH2Cl (243db) and the fluoroolefin is CF3CCl═CH2 (1233xf).

### Claim 14 (depends on 13)

The composition of claim 13 further comprising trans-CF3CH═CHCl (1233zd) and CF3CH═CH2 (1243zf).

### Claim 15 (depends on 1)

The composition of claim 1, wherein the caustic agent is present at a molar ratio in the range of about 0.01 to about 5 with respect to the hydrochlorofluorocarbon mixture.

### Claim 16 (depends on 1)

The composition of claim 1, wherein about 97% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin.

### Claim 17 (depends on 1)

The composition of claim 1, wherein the composition is a product of a dehydrohalogenation process.

### Claim 18 (depends on 1)

The composition of claim 1, wherein the perfluorinated alkyl group is selected from the group consisting of —CF3 and —CF2CF3.

### Claim 19 (depends on 1)

The composition of claim 1, wherein the solvent comprises water and at least one additional solvent selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 1,3-butandiol, 1,2-butanediol, acetonitrile, acetaldehyde, acetone, ethylene glycol, propylene glycol, tetrahydrofuran, triethylene glycol, 1,3-propanediol, glycerol, and 1,4 dioxane.

### Claim 20 (depends on 1)

The composition of claim 1, wherein the caustic agent is selected from the group consisting of an alkali metal oxide, an alkali metal hydroxide, an alkali metal amide, an alkaline earth metal oxide, an alkaline earth metal hydroxide, an alkaline earth metal amide, an alkali metal carbonate, an alkali metal phosphate, and an alkali metal carboxylate.

### Claim 21 (depends on 8)

The composition of claim 8, wherein the amine is selected from the group consisting of a polyamine, a heterocyclic amine, hydrazine, a hydrazine derivative, and an aromatic amine.

### Claim 22 (depends on 1)

The composition of claim 1, wherein the composition is free of any dehydrohalogenation catalyst, including any phase transfer catalyst.

### Claim 23 (depends on 15)

The composition of claim 15, wherein the molar ratio is in the range of about 0.05 to about 1.5.