CA2157315A1 - Process for the preparation of fluoroketones - Google Patents
Process for the preparation of fluoroketonesInfo
- Publication number
- CA2157315A1 CA2157315A1 CA002157315A CA2157315A CA2157315A1 CA 2157315 A1 CA2157315 A1 CA 2157315A1 CA 002157315 A CA002157315 A CA 002157315A CA 2157315 A CA2157315 A CA 2157315A CA 2157315 A1 CA2157315 A1 CA 2157315A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- carried out
- preparation
- reaction
- fluoroketones
- 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.)
- Abandoned
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
- C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/167—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This invention concerns a process for the preparation of fluoroketones by the isomerization of corresponding epoxides, in the presence of an aluminum chlorofluoride catalyst. Fluorinated ketones are useful intermediates for the synthesis of various fluorinated compounds.
Description
TITT~F~
PROCESS FOR THE PREPARATION OF FLUOROKETONES
FTFTn OF T~F INVTNTION
This invention concerns a process for the preparation of fluoroketones by the isomerization of the corresponding epoxides in the presence of a Lewis acid catalyst. Fluorinated ketones, such as hexafluoro-acetone, are useful intermediates for the synthesis of a variety of fluorinated compounds.
T~ T R~K~RouNn U.S. Pat. 4,302,608 discloses a continuous process for isomerisation of hexafloropropylene oxide (HFPO) to hexafluoroacetone in the presence of an antimony pentafluoride (SbFs) catalyst.
U.S. Pat. 3,213,134 discloses the isomerization of epoxide of perfluoroheptene-l into perfluoroheptanone-2.
U.S. Pat. 3,321,515 teaches that HFPO can be converted into hexafluoroacetone (HFA) by reaction with alumina at 100C (yield 47%) or by reaction with AlC13.
I. L. Knunyants, V. V. Shokina and E. I. Mysov in Izv. AN SSSR. Ser. Khim. 2725 (1973) CA 80, 95151 (1974) disclose the reaction of HFPO with SbCl5 at 170C to give a mixture of 15% of chloropentafluoroacetone and 80% of HFA.
A. Ya. Zapevalov, I. P. Kolenko, V. S. Plashkin Zh. Org. Khim. 11,1622 (1975), CA 83, 192954 (1975), and A. Ya. Zapevalov, T. I. Filyakova, M. I. Kodess, I. P. Kolenko Zh. Org. Khim. 22 (1), 93-9 (1986), CA
106, 4771 disclose the use of SbFs as catalyst for the isomerization of a number of higher epoxides of polyfluoroolefines but all their examples are limited to fluoroolefins without functional groups because or incompatability of SbF5 with such groups, for example as -C(O)F. See: T. I. Filyakova, R. E. Ilatovskii, A. Ya.
Zapevalov Zh. Org. Khim. 27, NolO, 2055-60 (1991).
21~7315 Aluminum chloride has limited use in ring-opening reaction of fluoroepoxides because of extensive formation of by-products. See L. A. Saloutina, A. Ya.
Zapevalov, M. I. Kodess, I. P. Kolenko and L. S. German Izv. AN SSSR. Ser. Khim. 1434 (1983), CA 99, 157790 z, 1983.
Use of the present process with its aluminum chlorofluoride Lewis acid catalysts improves upon the processes and catalysts dislosed in the art by allowing for better yields with less by-product formation under generally milder temperature and pressure conditions.
SU~MA~Y OF TE~F. INVF:~TTON
This invention provides a process for the preparation of fluoroketones of the structure:
RfCF2C(O)CFXY
wherein X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or C1-C5 fluoroalkyl, said Cl-Cs fluoroalkyl optionally cont.aining in-chain oxygen and terminal functional groups; by isomerization of fluorinated epoxides of terminal and internal olefins in the presence of an aluminum chlorofluoride Lewis acid catalyst selected from aluminum chlorofluoride AlFnC13_n, wherein n is from 0.05-2.95.
The process can be carried out in the optional presence of one or a mixture of inert solvents.
Use of a solid aluminum mixed halide catalyst avoids the handling problems experienced with, for example, SbF5, which is a viscous, corrosive liquid.
DF.TATT.F.n DF.SCRIPTION OF T~F~ INVI;'.NTION
Polyfluorinated ketones RfCF2C(O)CFXY are prepared by the isomerization of epoxides in the presence of a Lewis acid catalyst, such as AlFnC13_n~ wherein n is from 2I5731~
0.05 to 2.95, preferably 2.0 to 2.95. Epoxides useful herein are of the formula f I
R,CFOCFCFXY
where X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or Cl-Cs 5 fluoroalkyl, said C1-Cs fluoroalkyl optionally containing in-chain oxygen and terminal functional groups such as -CN, -OC6F5, -C(O)R' (wherein R' is Cl-Cs alkyl), -SO2F, -C(O)F. The most preferred epoxide herein is hexafluoropropylene oxide (HFPO).
The reaction is carried out in the presence of an aluminum halide Lewis acid catalyst, wherein the aluminum halide is a mixed halide containing F and at least one of Cl, Br or I. Preferred catalysts are of the structure AlFnC13_n wherein n is from 0.05 to 2.95, preferably 2.0 to 2.95. Fluorinated aluminum chloride catalysts can be prepared by the reaction of AlC13 and CFC13, according to the method described in U.S.
5,162,594, column 4, lines 35-57, which is incorporated herein by reference. Catalyst may be preformed or may be generated in situ. Reactants and catalysts should be free of moisture.
The proportion of catalyst to epoxide is 0.05 to 0.2 mol catalyst per mole of epoxide.
Reaction temperature is about 0-200C, preferably about 20C to 100C. Reaction times can vary from several seconds to about twenty four hours, depending upon temperature, catalyst activity and starting materials.
Solvents are generally not required for the reaction but may, optionally, be used if the solvents are relatively inert to the reaction conditions. By "relatively inert" herein is meant substantially 21~7315 unreactive toward the catalyst at reaction temperatures.
Materials suitable for solvents herein are perfluoro-alkanes, perfluorocycloalkanes, and perfluoroethers. In some cases, the ketone product of the process can be advantageously used as the solvent.
The process can be carried out in a batch or continuous mode. The reaction can be carried out in the gas phase, in a flow system over a fixed bed catalyst, such as the aluminum chlorofluoride catalyst.
10The products of the process are useful inter-mediates for the synthesis of various fluorinated compounds. For example, HFA is used in the synthesis of bisphenol AF.
F:x~ p T~F~ s Catalyst preparation, AlC13 + CFC13 500 g (3.75 mol) of AlC13 (Aldrich-99% pure) was stirred mechanically under N2 in a round bottom flask fitted with a -80C condenser while 1750 mL (about 2625 g, 19 mol) of CFC13 was added over a 1.5 hr period.
Reaction is very exothermic in the early stages, so addition of CFC13 was slow at first in order to keep the temperature below 65C, then rapid. The resulting suspension was stirred an additional 3 hrs while volatiles (CF2C12) were allowed to escape through the condenser. The condenser was then replaced with a simple stillhead, and most of the CC14 was distilled under reduced pressure [mainly bp 38C (200 mm)].
Finally, the last traces of volatiles were removed by warming the residual solid to 30-35C at 0.05 mm Hg pressure.
The sealed round bottom flask was transferred to a dry box and unloaded into a Teflon~F~P bottle; 340 g of rather finely divided yellow-green solid was obtained.
Portions of the catalyst were weighed out in the dry box 21~7315 s as needed and taken out in plastic bottles with pressure-seal caps.
Analysis for fluorine of the products from preparation of this type indicated the composition to be 5 AlF2 . sclo . 1, AlFncl ~3-n); n = 2.9. The aluminum chlorofluoride catalyst is abbreviated ACF herein.
F:XA~PT.F. 1 Two g of ACF and 20 mmol of HFPO were loaded into an evacuated cylinder through a vacuum line at -196C.
The cylinder was warmed up to 25C. After 2 h at this temperature, gas-phase IR confirmed that all HFPO ~as converted into HFA. The yield was quantitative.
F.X~PT.F. ?
Inside of a dry box, 0.3 g of ACF was placed in a 5 mL glass sample tube equipped with Teflon stopcock;
1 g of oxide CNCF2CF2OCF2-CFOCF2 was added in one portion. The tube was closed. Exothermic reaction was observed. After 2 h only the corresponding ketone CNCF2CF2OCF2C(O)CF3 was found in the sample tube according to 19F NMR, IR and GC. IR (neat): 2273 (CN), 1807 (C=O) cm~1. The yield was quantitative.
F.XA~PT.F. 3 As in Example 2, 0.3 g of ACF was used for quantitat ve isomerization of 1 g of oxide C6FsocF2cFocF2 into ketone C6FsOCF2 C(O) CF3. IR: 1802 (C=O) cm~1, on the 19F NMR spectrum corresponds to the proposed structure.
~;:XA~PT.F. 4 As in Example 1, a mixture of 0.5 g ACF and 5 g of perfluoro-2,3-epoxypentane (85% purity, the rest perfluoropentene-2) was kept at 150C for 18 h.
According to GC and 19F NMR data, the reaction mixture contained 37% perfluoro-2-pentanone, 26% perfluoro-3-pentanone, 22% of starting oxide and 15% of perfluoro-2ls73l5 pentene-2. Conversion of oxide was 74%, yield of ketones >95%.
F.XA~PT.~;: 5 Hexafluoropropylene oxide (13.8 g) was bubbled S through a suspension of 2 g of ACF suspended in 50 mL of the cyclic dimer of hexafluoropropene at the rate of 0.04 g/min at 25C and atmospheric pressure. The outcoming gases (19.3 g) were collected in a cold (-78C) trap protected against atmospheric moisture.
The product, according to 19F NMR data, was a mixture of 68% of hexafluoroacetone and 32% of solvent, no starting material was found. The yield of HFA was 94%, conversion of hexafluoropropylene oxide was 100%.
PROCESS FOR THE PREPARATION OF FLUOROKETONES
FTFTn OF T~F INVTNTION
This invention concerns a process for the preparation of fluoroketones by the isomerization of the corresponding epoxides in the presence of a Lewis acid catalyst. Fluorinated ketones, such as hexafluoro-acetone, are useful intermediates for the synthesis of a variety of fluorinated compounds.
T~ T R~K~RouNn U.S. Pat. 4,302,608 discloses a continuous process for isomerisation of hexafloropropylene oxide (HFPO) to hexafluoroacetone in the presence of an antimony pentafluoride (SbFs) catalyst.
U.S. Pat. 3,213,134 discloses the isomerization of epoxide of perfluoroheptene-l into perfluoroheptanone-2.
U.S. Pat. 3,321,515 teaches that HFPO can be converted into hexafluoroacetone (HFA) by reaction with alumina at 100C (yield 47%) or by reaction with AlC13.
I. L. Knunyants, V. V. Shokina and E. I. Mysov in Izv. AN SSSR. Ser. Khim. 2725 (1973) CA 80, 95151 (1974) disclose the reaction of HFPO with SbCl5 at 170C to give a mixture of 15% of chloropentafluoroacetone and 80% of HFA.
A. Ya. Zapevalov, I. P. Kolenko, V. S. Plashkin Zh. Org. Khim. 11,1622 (1975), CA 83, 192954 (1975), and A. Ya. Zapevalov, T. I. Filyakova, M. I. Kodess, I. P. Kolenko Zh. Org. Khim. 22 (1), 93-9 (1986), CA
106, 4771 disclose the use of SbFs as catalyst for the isomerization of a number of higher epoxides of polyfluoroolefines but all their examples are limited to fluoroolefins without functional groups because or incompatability of SbF5 with such groups, for example as -C(O)F. See: T. I. Filyakova, R. E. Ilatovskii, A. Ya.
Zapevalov Zh. Org. Khim. 27, NolO, 2055-60 (1991).
21~7315 Aluminum chloride has limited use in ring-opening reaction of fluoroepoxides because of extensive formation of by-products. See L. A. Saloutina, A. Ya.
Zapevalov, M. I. Kodess, I. P. Kolenko and L. S. German Izv. AN SSSR. Ser. Khim. 1434 (1983), CA 99, 157790 z, 1983.
Use of the present process with its aluminum chlorofluoride Lewis acid catalysts improves upon the processes and catalysts dislosed in the art by allowing for better yields with less by-product formation under generally milder temperature and pressure conditions.
SU~MA~Y OF TE~F. INVF:~TTON
This invention provides a process for the preparation of fluoroketones of the structure:
RfCF2C(O)CFXY
wherein X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or C1-C5 fluoroalkyl, said Cl-Cs fluoroalkyl optionally cont.aining in-chain oxygen and terminal functional groups; by isomerization of fluorinated epoxides of terminal and internal olefins in the presence of an aluminum chlorofluoride Lewis acid catalyst selected from aluminum chlorofluoride AlFnC13_n, wherein n is from 0.05-2.95.
The process can be carried out in the optional presence of one or a mixture of inert solvents.
Use of a solid aluminum mixed halide catalyst avoids the handling problems experienced with, for example, SbF5, which is a viscous, corrosive liquid.
DF.TATT.F.n DF.SCRIPTION OF T~F~ INVI;'.NTION
Polyfluorinated ketones RfCF2C(O)CFXY are prepared by the isomerization of epoxides in the presence of a Lewis acid catalyst, such as AlFnC13_n~ wherein n is from 2I5731~
0.05 to 2.95, preferably 2.0 to 2.95. Epoxides useful herein are of the formula f I
R,CFOCFCFXY
where X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or Cl-Cs 5 fluoroalkyl, said C1-Cs fluoroalkyl optionally containing in-chain oxygen and terminal functional groups such as -CN, -OC6F5, -C(O)R' (wherein R' is Cl-Cs alkyl), -SO2F, -C(O)F. The most preferred epoxide herein is hexafluoropropylene oxide (HFPO).
The reaction is carried out in the presence of an aluminum halide Lewis acid catalyst, wherein the aluminum halide is a mixed halide containing F and at least one of Cl, Br or I. Preferred catalysts are of the structure AlFnC13_n wherein n is from 0.05 to 2.95, preferably 2.0 to 2.95. Fluorinated aluminum chloride catalysts can be prepared by the reaction of AlC13 and CFC13, according to the method described in U.S.
5,162,594, column 4, lines 35-57, which is incorporated herein by reference. Catalyst may be preformed or may be generated in situ. Reactants and catalysts should be free of moisture.
The proportion of catalyst to epoxide is 0.05 to 0.2 mol catalyst per mole of epoxide.
Reaction temperature is about 0-200C, preferably about 20C to 100C. Reaction times can vary from several seconds to about twenty four hours, depending upon temperature, catalyst activity and starting materials.
Solvents are generally not required for the reaction but may, optionally, be used if the solvents are relatively inert to the reaction conditions. By "relatively inert" herein is meant substantially 21~7315 unreactive toward the catalyst at reaction temperatures.
Materials suitable for solvents herein are perfluoro-alkanes, perfluorocycloalkanes, and perfluoroethers. In some cases, the ketone product of the process can be advantageously used as the solvent.
The process can be carried out in a batch or continuous mode. The reaction can be carried out in the gas phase, in a flow system over a fixed bed catalyst, such as the aluminum chlorofluoride catalyst.
10The products of the process are useful inter-mediates for the synthesis of various fluorinated compounds. For example, HFA is used in the synthesis of bisphenol AF.
F:x~ p T~F~ s Catalyst preparation, AlC13 + CFC13 500 g (3.75 mol) of AlC13 (Aldrich-99% pure) was stirred mechanically under N2 in a round bottom flask fitted with a -80C condenser while 1750 mL (about 2625 g, 19 mol) of CFC13 was added over a 1.5 hr period.
Reaction is very exothermic in the early stages, so addition of CFC13 was slow at first in order to keep the temperature below 65C, then rapid. The resulting suspension was stirred an additional 3 hrs while volatiles (CF2C12) were allowed to escape through the condenser. The condenser was then replaced with a simple stillhead, and most of the CC14 was distilled under reduced pressure [mainly bp 38C (200 mm)].
Finally, the last traces of volatiles were removed by warming the residual solid to 30-35C at 0.05 mm Hg pressure.
The sealed round bottom flask was transferred to a dry box and unloaded into a Teflon~F~P bottle; 340 g of rather finely divided yellow-green solid was obtained.
Portions of the catalyst were weighed out in the dry box 21~7315 s as needed and taken out in plastic bottles with pressure-seal caps.
Analysis for fluorine of the products from preparation of this type indicated the composition to be 5 AlF2 . sclo . 1, AlFncl ~3-n); n = 2.9. The aluminum chlorofluoride catalyst is abbreviated ACF herein.
F:XA~PT.F. 1 Two g of ACF and 20 mmol of HFPO were loaded into an evacuated cylinder through a vacuum line at -196C.
The cylinder was warmed up to 25C. After 2 h at this temperature, gas-phase IR confirmed that all HFPO ~as converted into HFA. The yield was quantitative.
F.X~PT.F. ?
Inside of a dry box, 0.3 g of ACF was placed in a 5 mL glass sample tube equipped with Teflon stopcock;
1 g of oxide CNCF2CF2OCF2-CFOCF2 was added in one portion. The tube was closed. Exothermic reaction was observed. After 2 h only the corresponding ketone CNCF2CF2OCF2C(O)CF3 was found in the sample tube according to 19F NMR, IR and GC. IR (neat): 2273 (CN), 1807 (C=O) cm~1. The yield was quantitative.
F.XA~PT.F. 3 As in Example 2, 0.3 g of ACF was used for quantitat ve isomerization of 1 g of oxide C6FsocF2cFocF2 into ketone C6FsOCF2 C(O) CF3. IR: 1802 (C=O) cm~1, on the 19F NMR spectrum corresponds to the proposed structure.
~;:XA~PT.F. 4 As in Example 1, a mixture of 0.5 g ACF and 5 g of perfluoro-2,3-epoxypentane (85% purity, the rest perfluoropentene-2) was kept at 150C for 18 h.
According to GC and 19F NMR data, the reaction mixture contained 37% perfluoro-2-pentanone, 26% perfluoro-3-pentanone, 22% of starting oxide and 15% of perfluoro-2ls73l5 pentene-2. Conversion of oxide was 74%, yield of ketones >95%.
F.XA~PT.~;: 5 Hexafluoropropylene oxide (13.8 g) was bubbled S through a suspension of 2 g of ACF suspended in 50 mL of the cyclic dimer of hexafluoropropene at the rate of 0.04 g/min at 25C and atmospheric pressure. The outcoming gases (19.3 g) were collected in a cold (-78C) trap protected against atmospheric moisture.
The product, according to 19F NMR data, was a mixture of 68% of hexafluoroacetone and 32% of solvent, no starting material was found. The yield of HFA was 94%, conversion of hexafluoropropylene oxide was 100%.
Claims (10)
1. A process for the preparation of fluoroketones of the structure:
RfCF2C(O)CFXY
wherein X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or C1-C5 fluoroalkyl, said C1-C5 fluoroalkyl optionally containing in-chain oxygen and terminal functional groups comprising:
isomerization of fluorinated epoxides of terminal and internal olefins of the structure:
where X, Y and Rf are as defined above, in the presence of a Lewis acid catalyst selected from the group consisting of aluminum chlorofluoride AlFnCl3-n, wherein n is from 0.05 to 2.95.
RfCF2C(O)CFXY
wherein X is F or Cl and Y is selected from the group consisting of F, Cl, and Rf, wherein Rf is F or C1-C5 fluoroalkyl, said C1-C5 fluoroalkyl optionally containing in-chain oxygen and terminal functional groups comprising:
isomerization of fluorinated epoxides of terminal and internal olefins of the structure:
where X, Y and Rf are as defined above, in the presence of a Lewis acid catalyst selected from the group consisting of aluminum chlorofluoride AlFnCl3-n, wherein n is from 0.05 to 2.95.
2. The process of Claim 1 wherein n is 2.0 to 2.95.
3. The process of Claim 1 carried out in the presence of an inert solvent.
4. The process of Claim 3 wherein the solvent is selected from the group consisting of perfluoroalkanes, perfluorocycloalkanes, and perfluoroethers.
5. The process of Claim 3 carried out in the fluoroketone product of Claim 1.
6. The process of Claim 1 carried out at a temperature of 0°C to 200°C.
7. The process of Claim 7 carried out at a temperature of 20°C to 100°C.
8. The process of Claim 1 wherein the proportion of catalyst to epoxide is 0.05 to 0.2 mole of catalyst per mole of epoxide.
9. The process of Claim 1 carried out over a bed of solid catalyst.
10. The process of Claim 1 wherein the starting material is HFPO and the product is HFA.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002157315A CA2157315A1 (en) | 1995-08-31 | 1995-08-31 | Process for the preparation of fluoroketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002157315A CA2157315A1 (en) | 1995-08-31 | 1995-08-31 | Process for the preparation of fluoroketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2157315A1 true CA2157315A1 (en) | 1997-03-01 |
Family
ID=4156519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002157315A Abandoned CA2157315A1 (en) | 1995-08-31 | 1995-08-31 | Process for the preparation of fluoroketones |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2157315A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115805087A (en) * | 2022-12-26 | 2023-03-17 | 上海华谊三爱富新材料有限公司 | Catalyst system, method for the production and use thereof |
-
1995
- 1995-08-31 CA CA002157315A patent/CA2157315A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115805087A (en) * | 2022-12-26 | 2023-03-17 | 上海华谊三爱富新材料有限公司 | Catalyst system, method for the production and use thereof |
| CN115805087B (en) * | 2022-12-26 | 2024-02-09 | 上海华谊三爱富新材料有限公司 | Catalyst system, method for the production and use thereof |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20010831 |