WO1994002439A1 - Purification of pentafluoroethane - Google Patents
Purification of pentafluoroethane Download PDFInfo
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- WO1994002439A1 WO1994002439A1 PCT/GB1993/001518 GB9301518W WO9402439A1 WO 1994002439 A1 WO1994002439 A1 WO 1994002439A1 GB 9301518 W GB9301518 W GB 9301518W WO 9402439 A1 WO9402439 A1 WO 9402439A1
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- Prior art keywords
- pentafluoroethane
- impurities
- catalyst
- hydrofluoroalkane
- hydrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
Definitions
- This invention relates to a process for the purification of pentafluoroethane and in particular to a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from compositions containing pentafluoroethane .
- a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature in the presence of a hydrogenation catalyst to convert the impurity or impurities to a hydrofluoroalkane and/or a hydrocarbon.
- the process may be operated so as to remove chlorine-containing impurities from the pentafluoroethane to the extent that the composition recovered after the process contains less than 1Z by volume of chlorine-containing impurities, preferably less than 0.5Z, more preferably less than 0.1 and especially less than 0.01Z of chlorine-containing impurities.
- the process may be operated to remove hyrofluoroethane impurities to below the level of 1Z by volume .
- the chlorine-containing impurity present in the pentafluoroethane will typically be a hydrochlorocarbon, chlorofluorocarbon or hydrochlorofluorocarbon. Under suitable conditions of temperature and pressure, these impurities may be converted to pentafluoroethane and/or another hydrofluoroalkane and/or hydrocarbons, for example methane and ethane which are readily separated from pentafluoroethane by conventional processes, for example distillation. Hydrofluoroalkane impurities in the pentafluoroethane will typically be converted to hydrocarbons .
- the product of hydrogenation of the impurity is itself a hydrofluoroalkane
- the product of hydrogenation of the impurity is itself a hydrofluoroalkane
- 1-chloro-l , 2 , 2 , 2-tetrafluoroethane which is hydrogenated to 1 , 1 , 1 , 2-tetrafluoroethane
- the final product may itself be a desirable mixture of hydrofluoroalkanes .
- chloropentafluoroethane may be hydrogenated to pentafluoroethane itself.
- the product of hydrogenation of the impurity may be desirable to separate the product of hydrogenation of the impurity from the pentafluoroethane, as for example where the product of hydrogenation is a hydrocarbon or where the product of hydrogenation is a hydrofluoroalkane which is not desired as a mixture with pentafluoroethane, for example fluoromethane and fluoroethane which are the hydrogenation products of trichlorofluoromethane and dichlorofluoroethane respectively.
- a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from compositions comprising pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature in the presence of a hydrogenation catalyst to convert the impurities to a hydrofluoroalkane and/or a hydrocarbon and separating the hydrocarbon and/or hydrofluoroalkane from the pentafluoroethane.
- pentafluoroethane compositions which are treated according to the invention typically comprise major proportions of pentafluoroethane and minor proportions of chlorine-containing compounds and other hydrofluoroalkanes although compositions comprising major proportions of hydrofluoroalkanes other than pentafluoroethane may be treated according _ A -
- composition treated according to the invention will comprise at least 102 by volume of pentafluoroethane and usually it will comprise at least 30Z of pentafluoroethane.
- composition treated according to the invention may also comprise hydrofluoroalkanes other than pentafluoroethane.
- hydrofluoroalkanes other than pentafluoroethane.
- these hydrofluoroalkanes may be converted to hydrocarbons or to other hydrofluoroalkanes or the hydrofluoroalkanes may pass unconverted through the process of the invention.
- Hydrogenation catalysts are well known in the art and a variety have been proposed, for example as described in the aforementioned Japanese patent applications.
- Such catalysts typically comprise a Group Villa metal, for example nickel, rhodium, iridium, ruthenium, palladium or platinum or a salt, for example halide or oxide, of the metal.
- the preferred catalyst depends to some extent upon the particular impurities present and upon the conditions of temperature and pressure employed, but in general a preferred catalyst comprises palladium, platinum and/or nickel.
- Such preferred catalysts may comprise only these metals or may comprise one or more of these metals and other metals which may be present as alloys with nickel, platinum and/or palladium or as mixtures of metals.
- the metal catalyst is typically carried on a suitable support, for example alumina, fluorinated alumina or an active carbon.
- any of these proposed hydrogenation catalysts may be employed in the process of the invention.
- Suitable conditions of temperatures and pressure under which the impurities are converted to hydrofluoroalkanes and/or hydrocarbons will depend to some extent upon the nature and amount of impurities present and the particular catalyst employed. Generally however, the temperature will be at least 350°C and preferably at least 400°C. The temperature is usually not higher than 600°C and preferably will not be higher than about 500°C. More preferred temperatures are in the range from about 420°C to about 520°C.
- the process may be carried out under atmospheric pressure, although we prefer to employ superatmospheric pressures, say up to about 30 bar, and preferably superatmospheric pressures in the range from about 5 bar to about 25 bar.
- the amount of hydrogen employed in the process may vary within wide limits and is dependent to some extent upon the amount and nature of the chlorine-containing impurities and/or hydrofluoroalkane impurities which may be hydrogenated in the process of the invention. Generally we prefer to use at least a stoichiometric excess of hydrogen based on the impurity or impurities to be hydrogenated and more preferably a stoichiometric excess in the range of from 1:1 to about 10:1, more preferably from about 2:1 to about 8:1.
- 87 ml of a catalyst comprising 16.02 nickel oxide supported on alumina was charged to a one inch diameter Monel reactor tube, the tube was placed in an oven and the catalyst was dried by heating to 250°C in a stream of nitrogen (100 ml/minute) for 16 hours .
- the nitrogen flow rate was increased to 3000 ml/minute and a stream of hydrogen was passed over the catalyst at a flow rate of 120 ml/minute.
- a mixed organic feed stream comprising 1 , 1 , 1-trifluoroethane , pentafluoroethane, 1 , 1 , 1 , 2-tetrafluoroethane and chloropentafluoroethane in the proportions shown in Table 1 was passed over the catalyst at atmospheric pressure and 400°C.
- the off gases were analysed by gas chromatography and the results are shown in Table 1.
- Example 3 The procedure of Example 1 was followed except that the catalyst comprised 0.5Z platinum supported on alumina and the mixed organic feed comprised 1,1,1-trifluoroethane, pentafluoroethane , 1 , 1 ,1,2-tetrafluoroethane and chlorotetrafluoroethane in the proportions shown in Table 3. The results are shown in Table 3.
- Example 4 The procedure of Example 4 was repeated except that the catalyst comprised 0.52 platinum supported on alumina and the mixed organic feed comprised 1,1,1-trifluoroethane, pentafluoroethane, 1, 1 , 1 ,2-tetrafluoroethane and chloropentafluoroethane in the proportions shown in Table 5. The results are also shown in Table 5.
- Example 5 The procedure of Example 5 was repeated except that the catalyst comprised 16.02 nickel supported on alumina, the ratio of hydrogen to organic feed, and the temperature were varied, the off gases were sampled and analysed by gas chromatography and the results are shown in Table 6.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Process for the removal of chlorine-containing impurities, for example chloropentafluoroethane, and/or hydrofluoroalkane impurities, for example 1,1,1,2-tetrafluoroethane, from pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature, for example 350-600 °C, in the presence of a hydrogenation catalyst, for example palladium-on-carbon, to convert the impurity or impurities to a hydrofluoroalkane and/or a hydrocarbon.
Description
PURIFICATION OF PENTAFLUOROETHANE
This invention relates to a process for the purification of pentafluoroethane and in particular to a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from compositions containing pentafluoroethane .
Recently, processes have been proposed for the production of pentafluoroethane which has been proposed, together with other hydrofluoroalkanes such as 1 , 1 , 1 , 2-tetrafluoroethane , difluoromethane and 1 , 1, 1-trifluoroethane , and blends thereof as a suitable replacement for chlorofluorocarbons due to the zero ozone depleting potential of hydrofluoroalkanes .
Thus it has been proposed in Japanese Patent Application Nos Kokai 3099026, 1258632 and 4029941 to produce pentafluoroethane by contacting pentafluorochloroethane with hydrogen in the presence of a hydrogenation catalyst. Suitable conditions of temperature and pressure and suitable catalysts are described in the aforementioned Japanese patent applications. However, these and other processes for the production of pentafluoroethane result in a product comprising pentafluoroethane together with impurities such as unconverted starting material and by-products .
Many of these impurities may be difficult to separate from pentafluoroethane by conventional processes, for example distillation, due to the similarity in boiling point between the impurity and pentafluoroethane , and/or the formation of pentafluoroethane/impurity azeotropes .
We have now found a simple process for the removal of such impurities from pentafluoroethane, by converting the impurities to a hydrofluoroalkane
and/or hydrocarbon which is easily separable from pentafluoroethane .
According to the present invention there is provided a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature in the presence of a hydrogenation catalyst to convert the impurity or impurities to a hydrofluoroalkane and/or a hydrocarbon.
The process may be operated so as to remove chlorine-containing impurities from the pentafluoroethane to the extent that the composition recovered after the process contains less than 1Z by volume of chlorine-containing impurities, preferably less than 0.5Z, more preferably less than 0.1 and especially less than 0.01Z of chlorine-containing impurities. Similarly the process may be operated to remove hyrofluoroethane impurities to below the level of 1Z by volume .
The chlorine-containing impurity present in the pentafluoroethane will typically be a hydrochlorocarbon, chlorofluorocarbon or hydrochlorofluorocarbon. Under suitable conditions of temperature and pressure, these impurities may be converted to pentafluoroethane and/or another hydrofluoroalkane and/or hydrocarbons, for example methane and ethane which are readily separated from pentafluoroethane by conventional processes, for example distillation. Hydrofluoroalkane impurities in the pentafluoroethane will typically be converted to hydrocarbons .
In certain circumstances, and in particular where the product of hydrogenation of the impurity is
itself a hydrofluoroalkane , for example 1-chloro-l , 2 , 2 , 2-tetrafluoroethane which is hydrogenated to 1 , 1 , 1 , 2-tetrafluoroethane , the final product may itself be a desirable mixture of hydrofluoroalkanes . Furthermore the chlorine-containing impurity, chloropentafluoroethane may be hydrogenated to pentafluoroethane itself. Alternatively, it may be desirable to separate the product of hydrogenation of the impurity from the pentafluoroethane, as for example where the product of hydrogenation is a hydrocarbon or where the product of hydrogenation is a hydrofluoroalkane which is not desired as a mixture with pentafluoroethane, for example fluoromethane and fluoroethane which are the hydrogenation products of trichlorofluoromethane and dichlorofluoroethane respectively.
According to a preferred embodiment of the invention there is provided a process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from compositions comprising pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature in the presence of a hydrogenation catalyst to convert the impurities to a hydrofluoroalkane and/or a hydrocarbon and separating the hydrocarbon and/or hydrofluoroalkane from the pentafluoroethane.
The pentafluoroethane compositions which are treated according to the invention typically comprise major proportions of pentafluoroethane and minor proportions of chlorine-containing compounds and other hydrofluoroalkanes although compositions comprising major proportions of hydrofluoroalkanes other than pentafluoroethane may be treated according
_ A -
to the invention. Generally the composition treated according to the invention will comprise at least 102 by volume of pentafluoroethane and usually it will comprise at least 30Z of pentafluoroethane.
The composition treated according to the invention may also comprise hydrofluoroalkanes other than pentafluoroethane. Depending upon the particular hydrofluoroalkane , the particular catalyst employed and the conditions under which the process is carried out, these hydrofluoroalkanes may be converted to hydrocarbons or to other hydrofluoroalkanes or the hydrofluoroalkanes may pass unconverted through the process of the invention.
Hydrogenation catalysts are well known in the art and a variety have been proposed, for example as described in the aforementioned Japanese patent applications. Such catalysts typically comprise a Group Villa metal, for example nickel, rhodium, iridium, ruthenium, palladium or platinum or a salt, for example halide or oxide, of the metal. The preferred catalyst depends to some extent upon the particular impurities present and upon the conditions of temperature and pressure employed, but in general a preferred catalyst comprises palladium, platinum and/or nickel. Such preferred catalysts may comprise only these metals or may comprise one or more of these metals and other metals which may be present as alloys with nickel, platinum and/or palladium or as mixtures of metals. The metal catalyst is typically carried on a suitable support, for example alumina, fluorinated alumina or an active carbon.
Any of these proposed hydrogenation catalysts may be employed in the process of the invention.
Suitable conditions of temperatures and pressure under which the impurities are converted to hydrofluoroalkanes and/or hydrocarbons will depend to some extent upon the nature and amount of impurities present and the particular catalyst employed. Generally however, the temperature will be at least 350°C and preferably at least 400°C. The temperature is usually not higher than 600°C and preferably will not be higher than about 500°C. More preferred temperatures are in the range from about 420°C to about 520°C.
The process may be carried out under atmospheric pressure, although we prefer to employ superatmospheric pressures, say up to about 30 bar, and preferably superatmospheric pressures in the range from about 5 bar to about 25 bar.
The amount of hydrogen employed in the process may vary within wide limits and is dependent to some extent upon the amount and nature of the chlorine-containing impurities and/or hydrofluoroalkane impurities which may be hydrogenated in the process of the invention. Generally we prefer to use at least a stoichiometric excess of hydrogen based on the impurity or impurities to be hydrogenated and more preferably a stoichiometric excess in the range of from 1:1 to about 10:1, more preferably from about 2:1 to about 8:1.
The invention is illustrated but not limited by the following examples. EXAMPLE 1
87 ml of a catalyst comprising 16.02 nickel oxide supported on alumina was charged to a one inch diameter Monel reactor tube, the tube was placed in an oven and the catalyst was dried by heating to
250°C in a stream of nitrogen (100 ml/minute) for 16 hours .
The nitrogen flow rate was increased to 3000 ml/minute and a stream of hydrogen was passed over the catalyst at a flow rate of 120 ml/minute. A mixed organic feed stream comprising 1 , 1 , 1-trifluoroethane , pentafluoroethane, 1 , 1 , 1 , 2-tetrafluoroethane and chloropentafluoroethane in the proportions shown in Table 1 was passed over the catalyst at atmospheric pressure and 400°C. The off gases were analysed by gas chromatography and the results are shown in Table 1.
Table 1
SAMPLE TEMP H2/0rg COMPOSITION
(°C) Ratio (gc area 2)
143a 125 134a 115 ethane/ methane
Feed 57.6 8.8 33.2 0.1 0.0
Off Gas 400 8:1 0.0 11.5 25.7 0.0 57.3
EXAMPLE 2
31g of a catalyst comprising 16Z nickel oxide supported on alumina was charged to a 3/4" Inconel reactor tube and the reactor tube was placed in an oven. Hydrogen ( 0.057g/minute ) and a mixed organic stream comprising 1 , 1 , 1-tetrafluoroethane , pentafluoroethane. 1 , 1 , 1 , 2-tetrafluoroethane and chlorotetrafluoroethane in the proportions shown in Table 2 were fed over the catalyst at a pressure of 12 barg and 380°C. The temperature was steadily increased to 500°C, off gas samples were taken and
analysed by Gas Chromatography. The results are shown in Table 2.
Table 2
SAMPLE TEMP Org. Feed COMPOSITION (°C) (g/min) (gc area Z)
143a 125 134a 124 ethane
Feed 20.3 9.0 66.9 3.7 0.0
Off Gas 380 0.35 16.1 6.8 71.2 2.3 3.6
Off Gas 450 0.40 8.4 7.4 58.5 0.9 24.8
Off Gas 500 0.21 1.7 6.6 24.0 0.0 67.7
EXAMPLE 3 The procedure of Example 1 was followed except that the catalyst comprised 0.5Z platinum supported on alumina and the mixed organic feed comprised 1,1,1-trifluoroethane, pentafluoroethane , 1 , 1 ,1,2-tetrafluoroethane and chlorotetrafluoroethane in the proportions shown in Table 3. The results are shown in Table 3.
Table 3
SAMPLE TEMP COMPOSITION (°C) ( c area Z )
143a 125 134a 115 ethane/ methane
Feed 59.5 9.1 30.7 0.1 0.0
Off Gas 400 2.0 7.2 10.1 0.0 80.7
EXAMPLE 4
87 ml of a catalyst comprising 1.0Z palladium supported on alumina was charged to a one inch diameter Monel reactor tube, the tube was placed in an oven and the catalyst was dried by heating to 250°C in a stream of nitrogen (100 ml/minute) for 16 hours . The nitrogen flow rate was increased to 300 ml/minute and a stream of hydrogen was passed over the catalyst at a flow rate of 120 ml/minute. A mixed organic feed stream comprising 1,1,1-trifluoroethane and pentafluoroethane in the proportions shown in Table 4 was passed over the catalyst with a flow rate of 30 ml/minute at a temperature of 370°C and atmospheric pressure. The temperature was varied, the off gases were sampled analysed by gas chromatography and the results are shown in Table 4.
Table 4
SAMPLE TEMP COMPOSITION (°C) ( gc area )
143a 125 ethane/ methane
Feed 67.2 32.7 0.0
Off Gas 370 0.92 36.9 62.1
Off Gas 388 0.22 36.9 62.8
Off Gas 404 0.01 37.1 62.9
EXAMPLE 5
The procedure of Example 4 was repeated except that the catalyst comprised 0.52 platinum supported on alumina and the mixed organic feed comprised 1,1,1-trifluoroethane, pentafluoroethane, 1, 1 , 1 ,2-tetrafluoroethane and chloropentafluoroethane in the proportions shown in Table 5. The results are also shown in Table 5.
Ta bl e 5
SAMPLE TEMP COMPOSITION (°C) (gc area 2)
143a 125 134a 115 ethane/ methane
Feed 59.5 9.1 30.7 0.1 0.0
Off Gas 380 2.0 7.2 10.1 0.0 80.7
Off Gas 450 0.0 4.3 0.0 0.0 95.7
EXAMPLE 6
The procedure of Example 5 was repeated except that the catalyst comprised 16.02 nickel supported on alumina, the ratio of hydrogen to organic feed, and the temperature were varied, the off gases were sampled and analysed by gas chromatography and the results are shown in Table 6.
Table 6
SAMPLE TEMP H2/0rg COMPOSITION (°C) Ratio (gc area 2)
143a 125 134a 115 ethane/ methane
Feed - - 57.6 8.8 33.2 0.1 0.0
Off Gas 450 5:1 0.0 11.5 5.4 0.0 62.7
Off Gas 400 8:1 0.0 11.5 25.7 0.0 57.3
Off Gas 450 8:1 0.0 7.4 0.0 0.0 92.6
EXAMPLE 7
57g of a catalyst comprising 162 nickel oxide supported on alumina was charged to 3/4" diameter Inconel reactor pipe and the reactor was placed in an oven. Hydrogen was passed over the catalyst, and a mixed organic feed stream comprising 1 , 1 , 1 , -trifluoroethane , pentafluoroethane and 1 , 1 , 1 , 2-tetrafluoroethane in the proportion shown in Table 4 was passed over the catalyst at 12 Barg pressure and at increasing elevated temperatures. The off gases from the reactor were periodically sampled and analysed by gas chromatography. The results are shown in Table 7.
Tabl e 7
SAMPLE TEMP FLOW RATE COMPOSITION (°C) (g/min) (gc/area Z)
Organics H2 143a 125 134a ethane/ methane
Feed 14.3 6.2 79.4
Off Gas 298 0.65 0.42 10.4 6.1 83.4 0.0
Off Gas 477 0.73 0.57 0.0 6.9 8.3 84.8
Off Gas 511 0.40 0.71 0.0 7.2 3.1 89.7
143a - 1,1,1-trifluoroethane
125 - pentafluoroethane
134a - 1,1,1,2-tetrafluoroethane
124 - chlorotetrafluoroethane
115 >- chloropentafluoroethane
Claims
1. A process for the removal of chlorine-containing impurities and/or hydrofluoroalkane impurities from pentafluoroethane which comprises contacting the impure pentafluoroethane with hydrogen at elevated temperature in the presence of a hydrogenation catalyst to convert the impurity or impurities to a hydrofluoroalkane and/or a hydrocarbon.
2 A process as claimed in claim 1 wherein the impure pentafluoroethane comprises a major proportion of pentafluoroethane.
3. A process as claimed in claim 1 or claim 2 wherein the catalyst comprises a Group Villa metal.
4. A process as claimed in claim 3 wherein the catalyst is carried on a support comprising alumina or carbon.
5. A process as claimed in any one of the preceding claims wherein the elevated temperature is at least 350°C.
6. A process as claimed in any one of the preceding claims wherein the elevated temperature is up to 600°C.
7. A process as claimed in any one of the preceding claims wherein the impure pentafluoroethane is contacted with hydrogen under superatmospheric pressure .
8. A process as claimed in any one of the preceding claims wherein the hydrogen is present in stoichiometric excess based on the impurity or impurities to be hydrogenated.
9. A process as claimed in any one of the preceding claims wherein the products of hydrogenation of the impurity or impurities are separated from the pentafluoroethane .
10. A process as claimed in any one of the preceding claims wherein the impure pentafluoroethane contains chloropentafluoroethane and is the product of hydrogenation of chloropentafluoroethane.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/374,669 US6340781B1 (en) | 1992-07-22 | 1993-07-20 | Purification of pentafluoroethane |
| EP93917873A EP0651733A1 (en) | 1992-07-22 | 1993-07-20 | Purification of pentafluoroethane |
| JP6504276A JPH07509238A (en) | 1992-07-22 | 1993-07-20 | Purification of pentafluoroethane |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9215562.1 | 1992-07-22 | ||
| GB9215563.9 | 1992-07-22 | ||
| GB929215562A GB9215562D0 (en) | 1992-07-22 | 1992-07-22 | Purification of pentafluoroethane |
| GB929215563A GB9215563D0 (en) | 1992-07-22 | 1992-07-22 | Purification of pentafluoroethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994002439A1 true WO1994002439A1 (en) | 1994-02-03 |
Family
ID=26301299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1993/001518 Ceased WO1994002439A1 (en) | 1992-07-22 | 1993-07-20 | Purification of pentafluoroethane |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6340781B1 (en) |
| EP (1) | EP0651733A1 (en) |
| JP (1) | JPH07509238A (en) |
| CA (1) | CA2140670A1 (en) |
| WO (1) | WO1994002439A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0732315A1 (en) * | 1995-03-17 | 1996-09-18 | Elf Atochem S.A. | Process for the hydrogenolysis of chlorofluorocarbons and hydrochlorofluorocarbons |
| EP0742192A1 (en) * | 1995-05-10 | 1996-11-13 | Elf Atochem S.A. | Purification of pentafluoroethane |
| EP0773207A4 (en) * | 1994-07-29 | 1997-06-18 | ||
| FR2752836A1 (en) * | 1996-08-30 | 1998-03-06 | Atochem Elf Sa | PURIFICATION OF PENTAFLUOROETHANE |
| EP0844226A1 (en) * | 1993-03-05 | 1998-05-27 | Daikin Industries, Limited | Method of producing 1,1,1,2,2-pentafluoroethane |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003014047A1 (en) * | 2001-08-06 | 2003-02-20 | Showa Denko K. K. | Production and use of hexafluoroethane |
| US7238314B2 (en) * | 2003-03-13 | 2007-07-03 | 3M Innovative Properties Company | Polymer transfer apparatus, methods, and composite webs |
| EP1601515A2 (en) * | 2003-03-13 | 2005-12-07 | 3M Innovative Properties Company | Composite webs and closure systems |
| US7989694B2 (en) * | 2004-12-06 | 2011-08-02 | Semiconductor Energy Laboratory Co., Ltd. | Photoelectric conversion element, solar battery, and photo sensor |
| US7534481B2 (en) * | 2006-08-08 | 2009-05-19 | 3M Innovative Properties Company | Shaped elastic tab laminates |
| JP2013058562A (en) | 2011-09-07 | 2013-03-28 | Semiconductor Energy Lab Co Ltd | Photoelectric conversion device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990008750A1 (en) * | 1989-02-02 | 1990-08-09 | E.I. Du Pont De Nemours And Company | Purification of saturated halocarbons |
-
1993
- 1993-07-20 US US08/374,669 patent/US6340781B1/en not_active Expired - Fee Related
- 1993-07-20 CA CA002140670A patent/CA2140670A1/en not_active Abandoned
- 1993-07-20 JP JP6504276A patent/JPH07509238A/en active Pending
- 1993-07-20 WO PCT/GB1993/001518 patent/WO1994002439A1/en not_active Ceased
- 1993-07-20 EP EP93917873A patent/EP0651733A1/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990008750A1 (en) * | 1989-02-02 | 1990-08-09 | E.I. Du Pont De Nemours And Company | Purification of saturated halocarbons |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 116, no. 25, 22 June 1992, Columbus, Ohio, US; abstract no. 255164n, SHINSUKE MORIKAWA ET AL. 'Preparation of pentafluoroethane' page 745 ;column 1 ; * |
| CHEMICAL ABSTRACTS, vol. 117, no. 11, 14 September 1992, Columbus, Ohio, US; abstract no. 111124x, HIROMO ONO ET AL. 'Purification of 1,1,1,2-tetrafluoroethane' page 815 ;column 2 ; * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0844226A1 (en) * | 1993-03-05 | 1998-05-27 | Daikin Industries, Limited | Method of producing 1,1,1,2,2-pentafluoroethane |
| JP3491702B2 (en) | 1994-07-29 | 2004-01-26 | ダイキン工業株式会社 | Method for purifying pentafluoroethane |
| EP0773207A4 (en) * | 1994-07-29 | 1997-06-18 | ||
| FR2731702A1 (en) * | 1995-03-17 | 1996-09-20 | Atochem Elf Sa | PROCESS FOR HYDROGENOLYSIS OF CHLOROFLUOROCARBONS AND HYDROCHLOROFLUOROCARBONS |
| KR100433081B1 (en) * | 1995-03-17 | 2004-09-04 | 아토피나 | Process for the hydrogenolysis of chlorofluorocarbons and of chlorofluorohydrocarbons |
| US5672790A (en) * | 1995-03-17 | 1997-09-30 | Elf Atochem S.A. | Process for the hydrogenolysis of chlorofluorocarbons and of chlorofluorohydrocarbons |
| EP0732315A1 (en) * | 1995-03-17 | 1996-09-18 | Elf Atochem S.A. | Process for the hydrogenolysis of chlorofluorocarbons and hydrochlorofluorocarbons |
| CN1063418C (en) * | 1995-03-17 | 2001-03-21 | 埃尔夫阿托化学有限公司 | HYdrogenolysis method for full substituted hydrocarbon containing Cl-F and hydrocarbon containing Cl-F |
| US5679876A (en) * | 1995-05-10 | 1997-10-21 | Elf Atochem S.A. | Purification of pentafluoroethane |
| FR2733976A1 (en) * | 1995-05-10 | 1996-11-15 | Atochem Elf Sa | PURIFICATION OF PENTAFLUOROETHANE |
| EP0742192A1 (en) * | 1995-05-10 | 1996-11-13 | Elf Atochem S.A. | Purification of pentafluoroethane |
| US5990364A (en) * | 1996-08-30 | 1999-11-23 | Schirmann; Jean-Pierre | Purification of pentafluoroethane |
| FR2752836A1 (en) * | 1996-08-30 | 1998-03-06 | Atochem Elf Sa | PURIFICATION OF PENTAFLUOROETHANE |
| DE19730588B4 (en) * | 1996-08-30 | 2005-12-22 | Elf Atochem S.A., Puteaux | Purification of pentafluoroethane |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2140670A1 (en) | 1994-02-03 |
| JPH07509238A (en) | 1995-10-12 |
| US6340781B1 (en) | 2002-01-22 |
| EP0651733A1 (en) | 1995-05-10 |
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