US5616819A
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Process for preparing fluorinated aliphatic compounds
Assignee: LaRoche Industries Inc
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Filing: 1995-08-28
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Granted: 1997-04-01
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Expires: 2015-08-28
Abstract
Abstract A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formula CH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-b wherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3. In the first step of the process, a chlorinated olefinic hydrocarbon of the formula CH.sub.c Cl.sub.2-c ═CH--CH.sub.d Cl.sub.3-d wherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formula CH.sub.e Cl.sub.2-e ═CH--CH.sub.f F.sub.3-f wherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2. The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used. The metallic part of such compound is arsenic, antimony, tin, boron or is selected from a metal in Group IVb, Vb. VIb. VIIb or VIIIb of the Periodic Table of the Elements. The desired fluorinated aliphatic hydrocarbon is subsequently separated and recovered. The process is particularly suitable for the preparation of 1,1,1,3,3-pentafluoropropane.
Inventors
- 👤 C. Bradford Boyce
- 👤 Randolph K. Belter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 19:58
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/38; C07C17/07; C07C17/08; C07C17/093; C07C17/20; C07C17/202; C07C17/206; C07C17/21; C07C19/00; C07C19/08
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
198 words
A process for preparing a fluorinated aliphatic hydrocarbon of the formula CH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-b wherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3, comprising i.) reacting a chlorinated olefinic-hydrocarbon of the formula CH.sub.c Cl.sub.2-c ═CH--CH.sub.d Cl.sub.3-d wherein c is 0 or the integer 1 or 2, and d is 0 or the integer 1 or 2 with anhydrous hydrogen fluoride at a temperature and for a time sufficient to form a chlorofluoro olefin of the formula CH.sub.e Cl.sub.2-e ═CH--CH.sub.f F.sub.3-f wherein e is 0 or the integer 1 or 2, and f is 0 or the integer 1 or 2 wherein said reacting is not catalyzed; ii.) reacting said chlorofluoro olefin with anhydrous hydrogen fluoride and in the presence of a catalytically effective amount of at least one of a metal oxide or at least one of a metal halide or mixtures of said at least one metal oxide with at least one metal halide for a time and at a temperature sufficient to form a reaction mixture containing said fluorinated aliphatic hydrocarbon; and iii.) separating said fluorinated aliphatic hydrocarbon from said reaction mixture.
Claim 2
Dependent Claim
198 words
A process for preparing a fluorinated aliphatic hydrocarbon of the formula CH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-b wherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3, comprising i.) reacting a chlorinated olefinic-hydrocarbon of the formula CH.sub.c Cl.sub.2-c ═CH--CH.sub.d Cl.sub.3-d wherein c is 0 or the integer 1 or 2, and d is 0 or the integer 1 or 2 with anhydrous hydrogen fluoride at a temperature and for a time sufficient to form a chlorofluoro olefin of the formula CH.sub.e Cl.sub.2-e ═CH--CH.sub.f F.sub.3-f wherein e is 0 or the integer 1 or 2, and f is 0 or the integer 1 or 2 wherein said reacting is not catalyzed; ii.) reacting said chlorofluoro olefin with anhydrous hydrogen fluoride and in the presence of a catalytically effective amount of at least one of a metal oxide or at least one of a metal halide or mixtures of said at least one metal oxide with at least one metal halide for a time and at a temperature sufficient to form a reaction mixture containing said fluorinated aliphatic hydrocarbon; and iii.) separating said fluorinated aliphatic hydrocarbon from said reaction mixture.
Claim 3
Dependent Claim
24 words
The process according to claim 1 wherein a, c and e are the integer 1 and b, d and f are the integer 0.
Claim 4
Dependent Claim
24 words
The process according to claim 1 wherein a, d and e are the integer 1 and b, c and f are the integer 0.
Claim 5
Dependent Claim
20 words
The process according to claim 1 wherein a and c are 0 and b and d are the integer 0.
Claim 6
Dependent Claim
18 words
The process according to claim 1 wherein steps i.) and ii.) are carried out in the liquid phase.
Claim 7
Dependent Claim
21 words
The process according to claim 1 wherein said temperature of step i.) is from about 50° C. to about 150° C.
Claim 8
Dependent Claim
21 words
The process according to claim 1 wherein said temperature of step ii.) is from about 25° C. to about 150° C.
Claim 9
Dependent Claim
27 words
The process according to claim 1 wherein said reacting of step ii.) is carried out in the presence of a metal oxide or of a metal halide.
Claim 10
Dependent Claim
44 words
The process according to claim 8 wherein the metal in said metal halide or oxide is selected from the group consisting of arsenic, antimony, tin, boron and a metal from Group IVb, Vb, VIb, VIIb, or VIIIb of the Periodic Table of the Elements.
Claim 11
Dependent Claim
41 words
The process according to claim 9 wherein the metal in said metal halide or oxide is antimony, arsenic, tin, bismuth or is one selected from the group of metals in Group IVb and VIIIb of the Periodic Table of the Elements.
Claim 12
Dependent Claim
28 words
The process according to claim 1 wherein the separation of step iii.) includes adding to said reaction mixture containing said fluorinated aliphatic hydrocarbon an organic or inorganic salt.
Claim 13
Dependent Claim
156 words
A process for preparing 1,1,1,3,3-pentafluoropropane which comprises i.) reacting a chloro olefin of the formula CH.sub.c Cl.sub.2-c ═CH--CH.sub.d Cl.sub.3-d wherein c and d are different and are 0 or the integer 1 with anhydrous hydrogen fluoride in the liquid phase and under autogenous pressure for a time and at a temperature sufficient to form a chlorofluoro olefin of the formula CH.sub.e Cl.sub.2-e ═CH--CH.sub.f F.sub.3-f wherein e is 1 and f is 0 wherein said reacting is not catalyzed; ii.) reacting said chlorofluoro olefin with anhydrous hydrogen fluoride and a catalytically effective amount of a halide or oxide of pentavalent antimony or a mixture of pentavalent antimony and tetravalent titanium for a time and at a temperature sufficient to form a reaction mixture containing said 1,1,1,3,3-pentafluoropropane; and iii.) separating said 1,1,1,3,3-pentafluoropropane from said reaction mixture by adding thereto a separation-causing amount of a compound selected from the group consisting of ammonium fluoride, sodium fluoride and potassium fluoride.
Claim 14
Dependent Claim
156 words
A process for preparing 1,1,1,3,3-pentafluoropropane which comprises i.) reacting a chloro olefin of the formula CH.sub.c Cl.sub.2-c ═CH--CH.sub.d Cl.sub.3-d wherein c and d are different and are 0 or the integer 1 with anhydrous hydrogen fluoride in the liquid phase and under autogenous pressure for a time and at a temperature sufficient to form a chlorofluoro olefin of the formula CH.sub.e Cl.sub.2-e ═CH--CH.sub.f F.sub.3-f wherein e is 1 and f is 0 wherein said reacting is not catalyzed; ii.) reacting said chlorofluoro olefin with anhydrous hydrogen fluoride and a catalytically effective amount of a halide or oxide of pentavalent antimony or a mixture of pentavalent antimony and tetravalent titanium for a time and at a temperature sufficient to form a reaction mixture containing said 1,1,1,3,3-pentafluoropropane; and iii.) separating said 1,1,1,3,3-pentafluoropropane from said reaction mixture by adding thereto a separation-causing amount of a compound selected from the group consisting of ammonium fluoride, sodium fluoride and potassium fluoride.
Claim 15
Dependent Claim
20 words
The process according to claim 12 wherein said mixture has a ratio of 4 parts antimony to 1 part titanium.
References Cited (Backward Citations)
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