WO2007077174A1 - Preparation of compounds having a perfluoroalkylcarbonyl group - Google Patents

Preparation of compounds having a perfluoroalkylcarbonyl group Download PDF

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Publication number
WO2007077174A1
WO2007077174A1 PCT/EP2006/070192 EP2006070192W WO2007077174A1 WO 2007077174 A1 WO2007077174 A1 WO 2007077174A1 EP 2006070192 W EP2006070192 W EP 2006070192W WO 2007077174 A1 WO2007077174 A1 WO 2007077174A1
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Prior art keywords
process according
carboxylic acid
acid fluorides
perfluorinated
reaction
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PCT/EP2006/070192
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French (fr)
Inventor
Wolfgang Wiesenhöfer
Eckhard Hausmann
Wolfgang Kalbreyer
Uta Claassen
Kerstin Eichholz
Johannes Eicher
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Solvay Fluor Gmbh
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Priority to EP06830825A priority Critical patent/EP1973864A1/en
Publication of WO2007077174A1 publication Critical patent/WO2007077174A1/en

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    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides

Definitions

  • the invention relates to a process for preparing compounds having a perfluoroalkylcarbonyl group by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluoroalkenes.
  • Fluorinated carbonyl compounds are intermediates in chemical synthesis.
  • Perfluoroalkyl ketones and perfluoroalkyl alkyl ketones can be used, for example, as fire extinguishing media, see WO 01/05468.
  • Fluorinated carboxylic acid fluorides are likewise intermediates in chemical synthesis, for example in the preparation of ketones, carboxylic acids or carboxylic acid derivatives such as esters or amides.
  • carbonyl fluoride or fluorinated carboxylic acid fluorides such as trifluoroacetyl fluoride, n- perfluoropropionyl fluoride, i-perfluoropropionyl fluoride or ⁇ -H- octafluorobutyryl fluoride onto tetrafluoroethylene, hexafluoropropene or octafluorobutene.
  • Caesium fluoride, potassium fluoride or potassium bifluoride are mentioned as catalysts.
  • the reaction is carried out under autogenous pressure.
  • the process of the invention provides for perfluorinated carboxylic acid fluorides and fluorinated ketones having a perfluoroalkyl group to be prepared by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluorinated alkenes, wherein the addition step is carried pressureless in an aprotic solvent. Hence, the reaction is performed in the liquid phase.
  • the addition of carboxylic acid fluorides onto perfiuorinated alkenes gives ketones.
  • appropriate choice of the molar ratio of alkene to carbonyl fluoride allows the carbonyl fluoride to be added onto two molecules of the alkene to form ketones.
  • the ideal stoichiometry according to the reaction equation for this reaction is 2:1. At an appropriate molar ratio, carbonyl fluoride and alkene form carboxylic acid fluorides. The ideal stoichiometry according to the reaction equation for this reaction is 1:1. The preparation of ketones from alkene and carboxylic acid fluoride is preferred for the purposes of the present invention.
  • alkenes and acid fluorides with a boiling point of 80 0 C or less at a pressure of 1 bar (abs.), preferably less than 50 0 C at a pressesure of 1 bar (abs.) are applied. Very preferably, they have a boiling point of less than 26°C at 1 bar (abs.).
  • R 1 and R 2 are identical or different and are each perfiuorinated Cl-C4-alkyl or fluorine.
  • R 1 is preferably fluorine, perfluoromethyl or perfluoroethyl and R 2 is preferably fluorine, perfluoromethyl or perfluoroethyl.
  • the perfiuorinated alkene is very particularly preferably hexafluoropropene.
  • Preferred carboxylic acid fluorides are those of the formula R 3 -C(O)F (II), where R 3 is a Cl-C5-alkyl radical which may, if desired, be substituted by at least one halogen atom.
  • R 3 is preferably Cl -C3-alkyl which is substituted by at least one fluorine atom.
  • R 3 is very particularly preferably CF 3 , CHF 2 or CF 2 Cl.
  • the process of the invention is outstandingly suitable for preparing trifluoromethyl perfluoroisopropyl ketone from trifluoroacetyl fluoride and hexafluoropropene.
  • the reaction is carried out in a polar aprotic solvent.
  • a high dielectric constant is advantageous.
  • Such solvents also have the ability to dissolve inorganic salts.
  • Preferred solvents have a boiling point which is at least 50 0 C, preferably at least 70 0 C.
  • Dialkylamides of the lower carboxylic or fatty acids e.g. dimethylformamide, dialkyl ethers, alkylene or polyalkylene glycols, liquid nitriles such as acetonitrile, propionitrile, butyronitrile, valeronitrile, benzonitrile, dinitriles, e.g. adiponitril, sulpholane and ionic liquids are very well suited.
  • solvents with a boiling point of lower than 250 0 C are applied.
  • the process of the invention is preferably carried out at a temperature of at least 50 0 C, particularly preferably of at least 70 0 C.
  • the upper limit is variable and determined by the boiling point of the solvent.
  • An upper limit of 170 0 C is preferred.
  • the upper limit is 150 0 C, still more preferably, 120 0 C.
  • the reactants can be introduced in very finely divided form into the solvent or the reaction mixture. This can, for example, be effected by introducing the reactants, particularly if they are gaseous, through a frit. Alternatively, a reactor with Raschig or Pall rings can be applied. In such a reactor, gas bubbles are diminuted, thus providing a higher surface for reaction.
  • pressureless means that, apart from the pressure for conveying the compounds introduced, no pressure acts on the reaction mixture, including no autogenous pressure.
  • the pressure is thus at least 0.9 bar (abs.).
  • the pressure lies in the range from atmospheric pressure (about 1 bar abs.) to a maximum of 1.5 bar (abs.).
  • catalyst use can be made of any catalyst known for that process.
  • a fluoride preferably a quaternary ammonium fluoride or an alkali metal fluoride such as KF or CsF.
  • the catalyst can be supported by a carrier.
  • it is carrier- free (bulk).
  • An advantage of this reaction system is, inter alia, a low corrosivity, i.e. the reaction can be carried out in glass despite the presence of a high fluoride concentration without visible etching of the glass occurring.
  • the process is preferably carried out continuously.
  • An advantage of the process of the invention is that it can be carried out continuously and no pressure apparatuses are required. Large amounts can therefore be prepared in standard apparatuses, as a result of which high capital costs are avoided.
  • the continuous mode of operation increases the space-time yield significantly (compared to the examples from US3185734, by a factor of 7). Yield and selectivity are very good.
  • Example 1 Preparation of trifluoromethyl perfluoroisopropyl ketone
  • Example 3 Preparation of trifiuoromethyl perfluoroisopropyl ketone
  • the total crude yield is 71 %.
  • the example demonstrates that relatively large amounts of ketone can be prepared in standard apparatuses and high capital costs for special reactors can thus be avoided.

Abstract

Carbonyl fluoride and carboxylic acid fluorides can be added onto perfluoroalkenes, for example hexafiuoropropene, under unpressurized conditions. Perfiuoroalkylcarboxylic acid fluorides or ketones having a perfluoroalkyl group can thus be prepared in a simple way.

Description

Preparation of compounds having a perfluoroalkylcarbonyl group
The invention relates to a process for preparing compounds having a perfluoroalkylcarbonyl group by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluoroalkenes.
Fluorinated carbonyl compounds are intermediates in chemical synthesis. Perfluoroalkyl ketones and perfluoroalkyl alkyl ketones can be used, for example, as fire extinguishing media, see WO 01/05468. Fluorinated carboxylic acid fluorides are likewise intermediates in chemical synthesis, for example in the preparation of ketones, carboxylic acids or carboxylic acid derivatives such as esters or amides.
The preparation of fluorinated ketones and carboxylic acid fluorides by addition of carbonyl fluoride (COF2) or carboxylic acid fluorides onto perfluorinated alkenes is known from the publications by F. S. Fawcett, CW. Tullock and D.D. Coffman in J. Am. Chem. Soc. 84 (1962), pages 4275 to 4285, and R.D. Smith, F.S. Fawcett and D.D. Coffman in J. Am. Chem. Soc. 84 (1962), pages 4285 to 4288. Here, carbonyl fluoride or fluorinated carboxylic acid fluorides such as trifluoroacetyl fluoride, n- perfluoropropionyl fluoride, i-perfluoropropionyl fluoride or ω-H- octafluorobutyryl fluoride onto tetrafluoroethylene, hexafluoropropene or octafluorobutene. Caesium fluoride, potassium fluoride or potassium bifluoride are mentioned as catalysts. The reaction is carried out under autogenous pressure. US patent 3185734, too, describes such a reaction carried out under autogenous pressure. Special pressure vessels are necessary for this.
It is an object of the present invention to provide a simplified process for preparing carboxylic acid fluorides and fluorinated ketones by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluoroalkenes. This object is achieved by the process of the present invention.
The process of the invention provides for perfluorinated carboxylic acid fluorides and fluorinated ketones having a perfluoroalkyl group to be prepared by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluorinated alkenes, wherein the addition step is carried pressureless in an aprotic solvent. Hence, the reaction is performed in the liquid phase. The addition of carboxylic acid fluorides onto perfiuorinated alkenes gives ketones. In the reaction of carbonyl fluoride, appropriate choice of the molar ratio of alkene to carbonyl fluoride allows the carbonyl fluoride to be added onto two molecules of the alkene to form ketones. The ideal stoichiometry according to the reaction equation for this reaction is 2:1. At an appropriate molar ratio, carbonyl fluoride and alkene form carboxylic acid fluorides. The ideal stoichiometry according to the reaction equation for this reaction is 1:1. The preparation of ketones from alkene and carboxylic acid fluoride is preferred for the purposes of the present invention.
In the process of the present invention, alkenes and acid fluorides with a boiling point of 800C or less at a pressure of 1 bar (abs.), preferably less than 500C at a pressesure of 1 bar (abs.) are applied. Very preferably, they have a boiling point of less than 26°C at 1 bar (abs.).
For the purposes of the present invention, perfiuorinated alkenes preferably correspond to the formula (I), R^CF=CFR2. R1 and R2 are identical or different and are each perfiuorinated Cl-C4-alkyl or fluorine. R1 is preferably fluorine, perfluoromethyl or perfluoroethyl and R2 is preferably fluorine, perfluoromethyl or perfluoroethyl. The perfiuorinated alkene is very particularly preferably hexafluoropropene.
Preferred carboxylic acid fluorides are those of the formula R3-C(O)F (II), where R3 is a Cl-C5-alkyl radical which may, if desired, be substituted by at least one halogen atom. R3 is preferably Cl -C3-alkyl which is substituted by at least one fluorine atom. R3 is very particularly preferably CF3, CHF2 or CF2Cl.
The process of the invention is outstandingly suitable for preparing trifluoromethyl perfluoroisopropyl ketone from trifluoroacetyl fluoride and hexafluoropropene.
The reaction is carried out in a polar aprotic solvent. A high dielectric constant is advantageous. Such solvents also have the ability to dissolve inorganic salts. Preferred solvents have a boiling point which is at least 500C, preferably at least 700C. Dialkylamides of the lower carboxylic or fatty acids, e.g. dimethylformamide, dialkyl ethers, alkylene or polyalkylene glycols, liquid nitriles such as acetonitrile, propionitrile, butyronitrile, valeronitrile, benzonitrile, dinitriles, e.g. adiponitril, sulpholane and ionic liquids are very well suited. Preferably, solvents with a boiling point of lower than 2500C are applied. The process of the invention is preferably carried out at a temperature of at least 500C, particularly preferably of at least 700C. The upper limit is variable and determined by the boiling point of the solvent. An upper limit of 1700C is preferred. Especially, the upper limit is 1500C, still more preferably, 1200C.
It is advantageous for the reactants to be introduced in very finely divided form into the solvent or the reaction mixture. This can, for example, be effected by introducing the reactants, particularly if they are gaseous, through a frit. Alternatively, a reactor with Raschig or Pall rings can be applied. In such a reactor, gas bubbles are diminuted, thus providing a higher surface for reaction.
The expression "pressureless" means that, apart from the pressure for conveying the compounds introduced, no pressure acts on the reaction mixture, including no autogenous pressure. The pressure is thus at least 0.9 bar (abs.). Preferably, the pressure lies in the range from atmospheric pressure (about 1 bar abs.) to a maximum of 1.5 bar (abs.).
As catalyst, use can be made of any catalyst known for that process. Preferably, use is made of a fluoride, preferably a quaternary ammonium fluoride or an alkali metal fluoride such as KF or CsF. The catalyst can be supported by a carrier. Preferably, it is carrier- free (bulk). An advantage of this reaction system is, inter alia, a low corrosivity, i.e. the reaction can be carried out in glass despite the presence of a high fluoride concentration without visible etching of the glass occurring.
The process is preferably carried out continuously.
An advantage of the process of the invention is that it can be carried out continuously and no pressure apparatuses are required. Large amounts can therefore be prepared in standard apparatuses, as a result of which high capital costs are avoided. The continuous mode of operation increases the space-time yield significantly (compared to the examples from US3185734, by a factor of 7). Yield and selectivity are very good.
The following examples illustrate the invention without restricting its scope. Examples : Example 1 : Preparation of trifluoromethyl perfluoroisopropyl ketone
In a cylindrical 200 ml glass vessel provided with a magnetic stirrer bar, 2.8 g of KF (0.05 mol) were slurried in 108.2 g of DMF (dimethylformamide). The mixture was heated to about 800C on a water bath and 18.3 g of trifluoroacetyl fluoride (TFAF; 0.16 mol) and 18.7 g of hexafluoropropene (0.12 mol) were introduced through a 1/8" FEP tube (FEP = fluorinated ethylene -propylene) at a feed rate of 5.23 g of TFAF/h and 5.34 g ofHFP/h. The distillation head was operated at -100C. The condensate was collected in an ice-cooled receiver. The offgas was passed through a stainless steel cylinder in a dry ice cooling bath.
Condensate in the receiver : 18.4 g (GC 81.9 % by area) ~ 0.06 mol ~ 47.2 % of theory
Condensate in the cold trap : 2.8 g (GC : 45.5 % by area) ~ 0.005 mol
The total yield of trifiuoromethyl perfluoroisopropyl ketone was thus 54 %. Example 2 : Preparation of trifiuoromethyl perfluoroisopropyl ketone
The experiment was repeated using the mixture of KF and DMF used in Example 1. However, the gases were passed through a frit. 43.2 g of TFAF (0.37 mol) were reacted in this way with 19.2 g of HFP (0.13 mol) at a feed rate of 24.7 g of TFAF/h and 11.0 g of HFP/h.
Condensate in the receiver : 23.3 g (GC : 86.9 % by area) ~ 0.08 mol ~ 58.5 % of theory
Condensate in the cold trap : 13.1 g (GC : 67.1 % by area) ~ 0.03 mol ~ 25.4 % of theory
The total yield here was thus 84 % of theory.
The example demonstrates that, despite the much simpler and time- saving mode of operation, it is possible to achieve a yield which is at least equal to that of the prior art, e.g. according to Example II of US-A 3185734. The space-time yield is significantly increased (by a factor of about 7) for the novel process. Example 3 : Preparation of trifiuoromethyl perfluoroisopropyl ketone
0.58 kg of potassium fluoride (KF) and 36.5 kg of dimethylformamide (DMF) were placed in a pilot plant apparatus (100 1 enamelled heatable steel vessel provided with superposed column, stirrer and pumped circuit) and the mixture was heated to 800C while stirring. The pumped circuit was then switched on and the starting materials hexafluoropropene (HFP) and trifluoroacetyl fluoride (TFAF) were introduced into this. The product was distilled from the reactor and collected in cooled receivers. Three experiments were carried out using the same DMF-KF batch and these are described in the following table :
Figure imgf000006_0001
a only sample taken; weight of product from this experiment is included in Experiment 2
The total crude yield is 71 %.
The example demonstrates that relatively large amounts of ketone can be prepared in standard apparatuses and high capital costs for special reactors can thus be avoided.

Claims

C L A I M S
1. Process for preparing perfluorinated carboxylic acid fluorides and fluorinated ketones having a perfluoroalkyl group by addition of carbonyl fluoride or carboxylic acid fluorides onto perfluorinated alkenes, wherein the addition step is carried out pressureless in an aprotic solvent.
2. Process according to Claim 1, characterized in that carboxylic acid fluorides are reacted with a perfluorinated alkene and a fluorinated ketone having a perfluoroalkyl group is prepared.
3. Process according to Claim 1, characterized in that carbonyl fluoride is reacted with a perfluorinated alkene and carboxylic acid fluorides or ketones are prepared as a function of the molar ratio.
4. Process according to Claim 1, characterized in that the perfluorinated alkene is a compound of the formula (I), R^CF=CFR2, where R1 and R2 are identical or different and are each perfluorinated Cl-C4-alkyl or fluorine.
5. Process according to Claim 4, characterized in that R1 is perfluoromethyl or perfluoroethyl and R is fluorine, perfluoromethyl or perfluoroethyl.
6. Process according to Claim 5, characterized in that the perfluorinated alkene is hexafluoropropene.
7. Process according to Claim 1, characterized in that carboxylic acid fluorides of the formula R3-C(O)F (II) where R3 is a Cl-C5-alkyl radical which may, if desired, be substituted by at least one halogen atom, are used.
8. Process according to Claim 7, characterized in that R3 is Cl-C3-alkyl which is substituted by at least one fluorine atom.
9. Process according to Claim 8, characterized in that R3 is CF3, CHF2 or CF2Cl.
10. Process according to Claim 1, characterized in that the reaction is carried out in a solvent having a boiling point of at least 500C, preferably at least 700C, at 1 bar (abs.), preferably in dimethylformamide.
11. Process according to Claim 1 , characterized in that the reaction is carried out at a temperature of at least 500C, preferably at least 700C, and not more than 1700C.
12. Process according to Claim 1, characterized in that the reaction is carried out continuously.
PCT/EP2006/070192 2005-12-30 2006-12-22 Preparation of compounds having a perfluoroalkylcarbonyl group WO2007077174A1 (en)

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EP05113084A EP1803702A1 (en) 2005-12-30 2005-12-30 Pressureless addition of acylfluorides to perfluoroalkenes
EP05113084.7 2005-12-30

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CN111233653A (en) * 2020-03-31 2020-06-05 国网陕西省电力公司电力科学研究院 Economical and efficient perfluoronitrile and perfluoroketone co-production process and device

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CN106946669B (en) * 2017-03-21 2020-09-15 国家电网公司 Environment-friendly insulating gas co-production process and industrial production device
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CN109704935B (en) * 2017-10-26 2022-04-05 浙江蓝天环保高科技股份有限公司 Method for preparing perfluoro-3-methyl-2-butanone
CN109896936A (en) * 2019-03-27 2019-06-18 广东电网有限责任公司 A kind of perfluor pentanone and preparation method thereof
CN110433743A (en) * 2019-06-30 2019-11-12 天津市长芦化工新材料有限公司 The preparation facilities of perfluor isobutyl acyl fluorides

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US3185734A (en) * 1960-10-25 1965-05-25 Du Pont Novel polyfluoro-substituted ketones and their preparation from polyfluoro acid fluorides
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US3185734A (en) * 1960-10-25 1965-05-25 Du Pont Novel polyfluoro-substituted ketones and their preparation from polyfluoro acid fluorides
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DATABASE CASREACT [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1981, IGUMNOV, S. M.; DELYAGINA, N. I.; KNUNYANTS, I. L.: ".alpha.- Fluoroalkylamines as a new source of unhydrated fluoride ion. 4. Acylation of perfluoroaliphatic carbanions by carboxylic acid fluorides", XP002381706, retrieved from STN Database accession no. 96:85015 *
DATABASE CASREACT [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1982, KNUNYANTS, I. L.; IGUMNOV, S. M.: ".beta.-Diketones containing perfluoroisopropyl and perfluoro-tert-butyl groups", XP002381705, retrieved from STN Database accession no. 96:142218 *
F. S. FAWCETT ET AL.: "The Chemistry of Carbonyl Fluoride II. Synthesis of Perfluoroisopropyl Ketones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 84, 1962, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 4275 - 4285, XP002380939 *
IGUMNOV, S. M.; DELYAGINA, N. I.; KNUNYANTS, I. L.: ".alpha.- Fluoroalkylamines as a new source of unhydrated fluoride ion. 4. Acylation of perfluoroaliphatic carbanions by carboxylic acid fluorides", IZVESTIA AKADEMII NAUK SSSR. SERIA HIMICESKAA, 1981, RUMOSCOW, pages 2339 - 2342, XP008064235 *
KNUNYANTS, I. L.; IGUMNOV, S. M.: ".beta.-Diketones containing perfluoroisopropyl and perfluoro-tert-butyl groups", IZVESTIA AKADEMII NAUK SSSR. SERIA HIMICESKAA, 1982, RUMOSCOW, pages 204 - 206, XP008064234 *

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Publication number Priority date Publication date Assignee Title
CN111233653A (en) * 2020-03-31 2020-06-05 国网陕西省电力公司电力科学研究院 Economical and efficient perfluoronitrile and perfluoroketone co-production process and device

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