US6548719B1
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US
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Process for producing fluoroolefins
Assignee: Honeywell International Inc
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Filing: 2001-09-25
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Granted: 2003-04-15
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Expires: 2021-09-25
Abstract
Abstract A process for producing a fluoroolefin of the formula: CF 3 CY═CX n H p wherein Y is a hydrogen atom or a halogen atom (i.e., fluorine, chlorine, bromine or iodine); X is a hydrogen atom or a halogen atom (i.e., fluorine, chlorine, bromine or iodine); n and p are integers independently equal to 0, 1 or 2, provided that (n+p)=2; comprising contacting, in the presence of a phase transfer catalyst, a compound of the formula: CF 3 C(R 1 a R 2 b )C(R 3 c R 4 d ), wherein R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom or a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, provided that at least one of R 1 , R 2 , R 3 , and R 4 is halogen and there is at least one hydrogen and one halogen on adjacent carbon atoms; a and b are independently=0, 1 or 2 and (a+b)=2; and c and d are independently=0, 1, 2 or 3 and (c+d)=3; and at least one alkali metal hydroxide. The alkali metal hydroxide can be, for example, potassium or sodium hydroxide and the phase transfer catalyst can be, for example, at least one: crown ether such as 18-crown-6 and 15-crown-5; or onium salt such as, quaternary phosphonium salt and quaternary ammonium salt. The olef in is useful, for example, as an intermediate for producing other industrial chemicals and as a monomer for producing oligomers and polymers.
Inventors
- 👤 Haridasan K. Nair
- 👤 Michael Van Der Puy
- 👤 David Nalewajek
- 👤 Timothy R. Demmin
- 👤 Andrew J. Poss
- 👤 David E. Bradley
- 👤 Ian R. Shankland
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 17:50
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/013; C07C17/04; C07C17/25
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
225 words
Process for the preparation of fluorine-containing olefins of the formula CF 3 CY═CX n H p wherein Y is a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine or iodine; X is a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine or iodine; n and p are integers independently equal to 0, 1 or 2, provided that (n+p)=2 comprising contacting, in the presence of a phase transfer catalyst: (A) a compound of the formula CF 3 C(R 1 a R 2 b )C(R 3 c R 4 d ), wherein R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that at least one of R 1 , R 2 , R 3 , and R 4 is halogen and there is at least one hydrogen and one halogen on adjacent carbon atoms; a and b are independently=0, 1 or 2 and (a+b)=2; and c and d are independently=0, 1, 2 or 3 and (c+d)=3; (B) at least one alkali metal hydroxide; (C) wherein said process is conducted at from about −5° C. to about 40° C.; and (D) wherein said process is conducted without added solvent or diluent.
Claim 2
Dependent Claim
225 words
Process for the preparation of fluorine-containing olefins of the formula CF 3 CY═CX n H p wherein Y is a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine or iodine; X is a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine or iodine; n and p are integers independently equal to 0, 1 or 2, provided that (n+p)=2 comprising contacting, in the presence of a phase transfer catalyst: (A) a compound of the formula CF 3 C(R 1 a R 2 b )C(R 3 c R 4 d ), wherein R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom or a halogen selected from the group consisting of fluorine; chlorine, bromine and iodine, provided that at least one of R 1 , R 2 , R 3 , and R 4 is halogen and there is at least one hydrogen and one halogen on adjacent carbon atoms; a and b are independently=0, 1 or 2 and (a+b)=2; and c and d are independently=0, 1, 2 or 3 and (c+d)=3; (B) at least one alkali metal hydroxide; (C) wherein said process is conducted at from about −5° C. to about 40° C.; and (D) wherein said process is conducted without added solvent or diluent.
Claim 3
Dependent Claim
27 words
Process of claim 1 wherein R 1 and R 2 are hydrogen, R 3 is F and c is 2, and R 4 is hydrogen or chlorine.
Claim 4
Dependent Claim
23 words
Process of claim 2 wherein said phase transfer catalyst is selected from: crown ethers; cryptates; polyalkylene glycols or derivatives thereof; and onium salts.
Claim 5
Dependent Claim
14 words
Process of claim 3 wherein said crown ether is selected from 18-crown-6 and 15-crown-5.
Claim 6
Dependent Claim
15 words
Process of claim 3 wherein said polyalkylene glycol is selected from polyethylene glycol and polypropylene.
Claim 7
Dependent Claim
14 words
Process of claim 3 wherein said onium salt is selected from ammonium and phosphonium-salts.
Claim 8
Dependent Claim
30 words
Process of claim 6 wherein said onium salt is selected from the group consisting of benzyltriethylammonium chloride, methyltrioctylammonium chloride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylphosphonium chloride, bis[tris(dimethylamino)phosphine]iminium chloride and tetratris[tris(dimethylamino)phosphinimino]phosphonium chloride.
Claim 9
Dependent Claim
20 words
Process of claim 3 wherein said alkali metal is selected from Group 1 of the Periodic Table of the Elements.
Claim 10
Dependent Claim
15 words
Process of claim 3 wherein said alkali metal is selected from lithium, sodium and potassium.
Claim 11
Dependent Claim
18 words
Process of claim 9 wherein said alkali metal is sodium and said phase transfer catalyst is 15-crown-5 ether.
Claim 12
Dependent Claim
18 words
Process of claim 9 wherein said alkali metal is potassium and said phase transfer catalyst is 18-crown-6 ether.
Claim 13
Dependent Claim
12 words
Process of claim 10 wherein said phase transfer catalyst is benzyltriethylammonium chloride.
Claim 14
Dependent Claim
35 words
Process of claim 2 wherein the molar ratio of alkali metal hydroxide to CF 3 C(R 1 a R 2 b )C(R 3 c R 4 d ) is from about 1 to about 10.
Claim 15
Dependent Claim
39 words
Process of claim 2 wherein the molar ratio of phase transfer catalyst to CF 3 C(R 1 a R 2 b )C(R 3 c R 4 d ) is from about 0.001 mol % to abpout 10 mol %.
Claim 16
Dependent Claim
9 words
Process of claim 2 wherein R 4 is hydrogen.
Claim 17
Dependent Claim
27 words
Process of claim 1 wherein R 1 is hydrogen and R 2 is bromine, R 3 is F and c is 2, and R 4 is bromine.
Claim 18
Dependent Claim
9 words
Process of claim 1 conducted in a continuous manner.
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