CA2081813C - Process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane (r 227) - Google Patents
Process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane (r 227) Download PDFInfo
- Publication number
- CA2081813C CA2081813C CA002081813A CA2081813A CA2081813C CA 2081813 C CA2081813 C CA 2081813C CA 002081813 A CA002081813 A CA 002081813A CA 2081813 A CA2081813 A CA 2081813A CA 2081813 C CA2081813 C CA 2081813C
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- hydrogen
- heptafluoropropane
- supported catalyst
- chloroheptafluoropropane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
Abstract
The invention relates to a process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane, which comprises react-ing 2-chloroheptafluoropropane with hydrogen in a molar ratio of from 1:1 to 1:10 in the gas phase on a pal-ladium-, platinum-, ruthenium-, rhodium-, nickel- or copper-containing supported catalyst at temperatures of from 100 to 400°C and pressures of from 1 to 50 bar.
Description
HOECHST ARTIENGESELLSCHAFT HOE 91/F 344 Dr.~
Description Process for the preparation of 1,1,1,2,3,3,3-heptafluoro-propane (R 227) The invention relates to a process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane (R 227) by hydrodechlor-ination of 2-chloroheptafluoropropane on a catalyst.
R 227 can be employed as a propellant gas and in air-conditioning equipment.
The preparation of R 227 from hexafluoropropene and hydrogen fluoride with the aid of an activated charcoal catalyst has already been disclosed (British Patent 902,590). However, the product contains unsaturated, toxic compounds, for example unreacted hexafluoropropene.
The present invention relates to a process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane, which comprises reacting 2-chloroheptafluoropropane with hydrogen in a molar ratio of from lsl to 1:10 in the gas phase on a palladium-, platinum-, ruthenium-, rhodium-, nickel- or copper-containing supported catalyst at temperatures of from 100 to 400°C and pressures of from 1 to 50 bar.
Examples of suitable support materials are activated charcoal, lithium-aluminum-spinal and aluminum oxide;
activated charcoal is preferred.
The Pd, Pt, Ru, Rh, Ni or Cu content of the supported catalyst is generally from 0.2 to 5 % by weight, based on the total weight of the catalyst. Palladium is preferred.
The reaction temperature is preferably from 200 to 300°C;
the preferred pressure range is from 1 to 5 bar.
From 1 to 10 mol of hydrogen, preferably from 1 to 3 mol of hydrogen, axe employed per mole of 2-chlorohepta-fluoropropane.
~~18~~~.3 Since the process according to the invention is a hydro dechlorination under hydrogenation conditions, no un saturated compounds, in particular no toxic compounds, are formed, in contrast to the known process of British Patent 902,530.
The preparation of the 2-chloroheptafluoropropane employ-ed as starting material is described in Chemical Abstracts (C91-081033).
The gas mixture produced is washed with water, deacidi fied and condensed. GC analysis shows the composition of the crude gas obtained in this way.
Example A vertical, electrically heated, tubular steel reactor (length - 100 cm, diameter - 2 cm) was charged with 200 ml of activated charcoal doped with 0.7 % by weight of palladium.
The catalyst was conditioned for 6 hours at 250°C while 5 I of hydrogen were passed through the catalyst per hour. 0.4 mol/h of CF3-CC1F-CF3 and 1 mol/h of hydrogen were then metered in at 250°C at atmospheric pressure.
The reaction gases leaving the reactor passed through a water scrubber with subsequent drying and condensation at -15°C.
Conversion: 89 %
Selectivity: 85 %
Description Process for the preparation of 1,1,1,2,3,3,3-heptafluoro-propane (R 227) The invention relates to a process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane (R 227) by hydrodechlor-ination of 2-chloroheptafluoropropane on a catalyst.
R 227 can be employed as a propellant gas and in air-conditioning equipment.
The preparation of R 227 from hexafluoropropene and hydrogen fluoride with the aid of an activated charcoal catalyst has already been disclosed (British Patent 902,590). However, the product contains unsaturated, toxic compounds, for example unreacted hexafluoropropene.
The present invention relates to a process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane, which comprises reacting 2-chloroheptafluoropropane with hydrogen in a molar ratio of from lsl to 1:10 in the gas phase on a palladium-, platinum-, ruthenium-, rhodium-, nickel- or copper-containing supported catalyst at temperatures of from 100 to 400°C and pressures of from 1 to 50 bar.
Examples of suitable support materials are activated charcoal, lithium-aluminum-spinal and aluminum oxide;
activated charcoal is preferred.
The Pd, Pt, Ru, Rh, Ni or Cu content of the supported catalyst is generally from 0.2 to 5 % by weight, based on the total weight of the catalyst. Palladium is preferred.
The reaction temperature is preferably from 200 to 300°C;
the preferred pressure range is from 1 to 5 bar.
From 1 to 10 mol of hydrogen, preferably from 1 to 3 mol of hydrogen, axe employed per mole of 2-chlorohepta-fluoropropane.
~~18~~~.3 Since the process according to the invention is a hydro dechlorination under hydrogenation conditions, no un saturated compounds, in particular no toxic compounds, are formed, in contrast to the known process of British Patent 902,530.
The preparation of the 2-chloroheptafluoropropane employ-ed as starting material is described in Chemical Abstracts (C91-081033).
The gas mixture produced is washed with water, deacidi fied and condensed. GC analysis shows the composition of the crude gas obtained in this way.
Example A vertical, electrically heated, tubular steel reactor (length - 100 cm, diameter - 2 cm) was charged with 200 ml of activated charcoal doped with 0.7 % by weight of palladium.
The catalyst was conditioned for 6 hours at 250°C while 5 I of hydrogen were passed through the catalyst per hour. 0.4 mol/h of CF3-CC1F-CF3 and 1 mol/h of hydrogen were then metered in at 250°C at atmospheric pressure.
The reaction gases leaving the reactor passed through a water scrubber with subsequent drying and condensation at -15°C.
Conversion: 89 %
Selectivity: 85 %
Claims (6)
1. A process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane, which comprise reacting 2-chloroheptafluoropropane with hydrogen in a molar ratio of from 1:1 to 1:10 in the gas phase on a palladium-, platinum-, ruthenium-, rhodium- or copper-containing supported catalyst at temperatures of from 100 to 400°C and pressures of from 1 to 50 bar.
2. The process as claimed in claim 1, wherein the Pd, Pt, Ru, Rh or Cu content of the supported catalyst is from 0.2 to 5% by weight.
3. The process as claimed in claim 1 or 2, wherein a palladium-containing supported catalyst is employed.
4. The process as claimed in any one of claims 1 to 3, wherein from 1 to 3 mol of hydrogen are employed per mole of 2-chloroheptafluoropropane.
5. The process as claimed in any one of claims 1 to 4, wherein the pressure is from 1 to 5 bar.
6. The process as claimed in any one of claims 1 to 5, wherein the temperature is from 100 to 300°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4136054 | 1991-11-01 | ||
| DEP4136054.0 | 1991-11-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2081813A1 CA2081813A1 (en) | 1993-05-02 |
| CA2081813C true CA2081813C (en) | 2004-01-13 |
Family
ID=6443903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002081813A Expired - Fee Related CA2081813C (en) | 1991-11-01 | 1992-10-30 | Process for the preparation of 1,1,1,2,3,3,3-heptafluoropropane (r 227) |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0539989B1 (en) |
| JP (1) | JP3249202B2 (en) |
| CA (1) | CA2081813C (en) |
| DE (1) | DE59208629D1 (en) |
| ES (1) | ES2104790T3 (en) |
| SG (1) | SG44743A1 (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024433A1 (en) * | 1992-06-03 | 1993-12-09 | Allied-Signal Inc. | Process producing a hydrofluorocarbon having at least one trifluoro group |
| CN1128016A (en) * | 1993-07-29 | 1996-07-31 | 联合讯号公司 | Process for the preparation of 1,1,1,3,3-pentafluoropropane |
| JP3500617B2 (en) * | 1993-08-27 | 2004-02-23 | ダイキン工業株式会社 | Method for producing hexafluorocyclobutane |
| US5315048A (en) * | 1993-09-30 | 1994-05-24 | Alliedsignal Inc. | Preparation of 1,1,1,2,3-pentafluoropropane by reduction of 1,2,3-trichloropentafluropropane |
| US5880317A (en) * | 1993-09-30 | 1999-03-09 | Alliedsignal Inc. | Preparation of 1,1,2,3,3-pentafluoropropane |
| BE1007822A5 (en) * | 1993-12-10 | 1995-10-31 | Solvay | SUPPORT FOR CATALYST hydrogenate ION SYSTEM INCLUDING THE CATALYST SUPPORT AND METHOD OF hydrodechlorination chlorofluorocarbons. |
| US6291729B1 (en) * | 1994-12-08 | 2001-09-18 | E. I. Du Pont De Nemours And Company | Halofluorocarbon hydrogenolysis |
| US5780691A (en) * | 1996-12-23 | 1998-07-14 | Allied Signal Inc. | Process for producing 1,1,1,2,3,3,3,-heptafluoroprane |
| FR2764883B1 (en) * | 1997-06-18 | 1999-07-16 | Atochem Elf Sa | PROCESS FOR THE MANUFACTURE OF HYDROFLUOROALCANES |
| DE69911186T2 (en) * | 1998-04-03 | 2004-07-15 | E.I. Du Pont De Nemours And Co., Wilmington | METHOD FOR PURIFYING AND USE OF 2-CHLORO-1,1,1,2,3,3,3-HEPTAFLUORPROPANE AND ITS AZEOTROPE WITH HF |
| WO1999051553A1 (en) * | 1998-04-03 | 1999-10-14 | E.I. Du Pont De Nemours And Company | Process for the production of fluorocarbons |
| US6281395B1 (en) | 1998-04-03 | 2001-08-28 | E. I. Du Pont De Nemours And Company | 1,1,1,2,3,3,3-heptafluoropropane manufacturing process |
| IT1301758B1 (en) | 1998-06-19 | 2000-07-07 | Ausimont Spa | 227 PREPARATION PROCESS |
| DE69928778T2 (en) | 1999-06-08 | 2006-07-06 | Gentium S.P.A., Villa Guardia | Application of complexes of cationic liposomes and polydeoxyribonucleotides such as drugs |
| US6235950B1 (en) | 1999-12-22 | 2001-05-22 | Honeywell International | Method of making hydrofluorocarbons |
| US7375728B2 (en) | 2001-10-01 | 2008-05-20 | University Of Minnesota | Virtual mirror |
| US7329786B2 (en) | 2001-09-28 | 2008-02-12 | Great Lakes Chemical Corporation | Processes for producing CF3CFHCF3 |
| US7223351B2 (en) | 2003-04-17 | 2007-05-29 | Great Lakes Chemical Corporation | Fire extinguishing mixtures, methods and systems |
| US20050020863A1 (en) * | 2003-07-25 | 2005-01-27 | Honeywell International Inc. | Method of making fluorinated propanes |
| US20050038302A1 (en) | 2003-08-13 | 2005-02-17 | Hedrick Vicki E. | Systems and methods for producing fluorocarbons |
| GB0721991D0 (en) | 2007-11-09 | 2007-12-19 | Ineos Fluor Holdings Ltd | Preparation method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE571509A (en) | 1957-09-26 | 1900-01-01 | ||
| GB902590A (en) | 1960-03-22 | 1962-08-01 | Allied Chem | Production of heptafluoropropane |
| GB8828544D0 (en) * | 1988-12-07 | 1989-01-11 | Ici Plc | Chemical process |
| ZA908087B (en) * | 1989-10-10 | 1992-06-24 | Du Pont | Halocarbon hydrogenolysis |
-
1992
- 1992-10-29 EP EP92118515A patent/EP0539989B1/en not_active Expired - Lifetime
- 1992-10-29 SG SG1996006724A patent/SG44743A1/en unknown
- 1992-10-29 ES ES92118515T patent/ES2104790T3/en not_active Expired - Lifetime
- 1992-10-29 DE DE59208629T patent/DE59208629D1/en not_active Expired - Fee Related
- 1992-10-30 CA CA002081813A patent/CA2081813C/en not_active Expired - Fee Related
- 1992-10-30 JP JP29338392A patent/JP3249202B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0539989A1 (en) | 1993-05-05 |
| CA2081813A1 (en) | 1993-05-02 |
| EP0539989B1 (en) | 1997-06-18 |
| ES2104790T3 (en) | 1997-10-16 |
| JPH05221894A (en) | 1993-08-31 |
| DE59208629D1 (en) | 1997-07-24 |
| JP3249202B2 (en) | 2002-01-21 |
| SG44743A1 (en) | 1997-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |