CN103145544A - Method for synthesis of pentafluoropropionyl fluoride - Google Patents
Method for synthesis of pentafluoropropionyl fluoride Download PDFInfo
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- CN103145544A CN103145544A CN2011104000596A CN201110400059A CN103145544A CN 103145544 A CN103145544 A CN 103145544A CN 2011104000596 A CN2011104000596 A CN 2011104000596A CN 201110400059 A CN201110400059 A CN 201110400059A CN 103145544 A CN103145544 A CN 103145544A
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- propylene oxide
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- 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
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Abstract
The invention discloses a method for synthesis of pentafluoropropionyl fluoride by using hexafluoropropylene oxide as a raw materisl. Under the effect of a catalyst, hexafluoropropylene oxide is subjected to isomerization reaction to synthesize pentafluoropropionyl fluoride. The catalyst comprises a main catalyst and a co-catalyst, wherein the main catalyst is organic amine compounds, five-or six-membered nitrogen-containing heterocycles or six-membered fused ring aromatic compounds; the co-catalyst is an alkali metal fluoride; and the quality ratio of the main catalyst to the co-catalyst is 100:1 to 5:1. The method provided by the invention has the advantages of mild preparation process, simple operations and high yield of synthesized pentafluoropropionyl fluoride. The prepared pentafluoropropionyl fluoride is suitable for preparing fluorine alkyl group-containing vinyl ethers and perfluoro-propionyl peroxides.
Description
Technical field
The present invention relates to a kind of synthetic method of five fluorine propionyl fluorides, especially relate to a kind of method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material.
Background technology
Five fluorine propionyl fluorides (Pentafluoropropionyl Fluoride), molecular formula: CF
3CF
2COF; No. Cas: 422-61-7; Molecular weight 166.02; Boiling point :-28 ℃; Be colourless gas under normal temperature, be acid, be easy to alcohol esterification occurs, meet water and generate HF gas and perfluorinated acid.
Five fluorine propionyl fluorides are as raw material and the intermediate of special functional fluoropolymer material, it is very important compound, as preparing a series of fluorine-containing alkyl vinyl ethers, this compound is the modified monomer of fluoroelastomer, can effectively destroy the degree of crystallinity of interpolymer, C-O key in molecule is given the flexibility of molecule, improving some performance of fluoroelastomer, as: resistance to low temperature, toughness, tear-resistant performance, with the adhesive property of base material etc.; Can be widely used in synthetic fluoroelastomer material.Five fluorine propionyl fluorides can also prepare the perfluoro propionyl superoxide; this compound is the necessary class initiator of high-purity grade of fluoropolymer of processability excellence; high-purity grade of fluoropolymer compared with common fluoropolymer; has lower metal impurities ion degree of separating out; better physics, chemical stability; can not pollute the chemical substance that contacts, be widely used in the material of the equipment such as manufacturing, storage, the container that transports high-purity chemicals, ultrapure chemical, pipe, pump, valve.Five fluorine propionyl fluorides can also prepare perfluor ketone, and perfluor ketone is the fire-fighting medium of a class environment, extinguishing property excellence, its ODP=0, and GWP=1, extinguishing property is suitable with Kazakhstan dragon 1211,1301.Five fluorine propionyl fluorides also can be hydrolyzed five fluorine propionic acid of system, and five fluorine propionic acid can prepare five fluorine methyl propionate or ethyl esters, can prepare PFPA, and these fluorochemicalss are raw materials of synthetic fluorine-containing medicines and agricultural chemicals.
In prior art, the preparation method of five fluorine propionyl fluorides mainly contains three kinds of raw material routes:
(1) Propylene oxide hexafluoride is raw material
US Patent No. 4729856 has been described and has been adopted platinotron and the Carious pipe of sealing to make reactor, under certain temperature of reaction, makees solvent with DMF or ethers etc., at raw material self pressure or add and depress, uses basic catalyst KHF
2, Na
2CO
3, dimethyl amine, vulkacit H make catalyzer, Propylene oxide hexafluoride is isomerizated into perfluoro-propionyl fluoride.This reactor product selectivity is lower, and reactor design is complicated, and reaction pressure is higher, and long reaction time is unfavorable for suitability for industrialized production.
US Patent No. 5684193 has been described with the tubular reactor or the autoclave pressure reactor that are lined with FEP, make catalyzer with the hydrogen fluoride amine complex, at a certain temperature Propylene oxide hexafluoride is isomerizated into perfluoro-propionyl fluoride, patent recommendation tubular type bubbling reactor, feed stock conversion and the product selectivity of reaction are more satisfactory, but the design of this technology reactor is more complicated, and the preparation of catalyzer is also more complicated, can use the stronger HF of corrodibility, be unfavorable for suitability for industrialized production.
Japanese Patent JP58038231 has described with KF or CsF and has made catalyzer, do raw material isomerization perfluoro-propionyl fluoride with Propylene oxide hexafluoride, 0 ℃～200 ℃ of temperature of reaction, under reaction pressure 1～10atm, KF take gac as carrier or CsF catalyzer, product perfluoro-propionyl fluoride yield reaches 71%, and raw material enters reactor with the gas phase form.
Japanese Patent JP4134046 has described with amines such as triethylamine, lutidine, toluquinolines and has made solvent, do raw material isomerization perfluoro-propionyl fluoride with Propylene oxide hexafluoride, under 40 ℃ of temperature of reaction, reacted 4 hours, product perfluoro-propionyl fluoride yield 61.9%, this technical products yield is not high, has the unfavorable factor of raw material Propylene oxide hexafluoride and product five fluorine propionyl fluoride separation difficulty.
(2) perfluoro methyl vinyl ether is raw material
Zompatori and V.Tortelli are at Journal of Fluorine Chemistry.125 (2) 199-204; reported on 2004 and prepared five fluorine propionyl fluorides take perfluoro methyl vinyl ether as the raw material isomerization; this route exists raw material expensive; the shortcoming of reaction product poor selectivity is unfavorable for that mass-producing prepares five fluorine propionyl fluorides.
(3) tetrafluoroethylene is raw material
US Patent No. 5259938 has been described take tetrafluoroethylene as raw material and fluorophosgene telomerizes synthetic five fluorine propionyl fluorides, and product yield reaches 68%, and this technological line exists raw material to be difficult to obtain equally, and product yield is low, is unfavorable for that mass-producing prepares the shortcoming of five fluorine propionyl fluorides.
All there is the shortcoming that product yield is low, suitability for industrialized production is difficult in above-mentioned five fluorine propionyl fluoride synthetic methods, needs to seek a kind of five fluorine propionyl fluoride synthetic methods of high yield.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of five fluorine propionyl fluorides, have preparation technology's gentleness, five fluorine propionyl fluoride yield advantages of higher simple to operate, synthetic.
For reaching goal of the invention the technical solution used in the present invention be:
Take Propylene oxide hexafluoride as raw material, the synthetic five fluorine propionyl fluorides of isomerization under catalyst action, this technological line is expressed as follows with reaction equation:
The raw materials used Propylene oxide hexafluoride of present technique is mainly to be prepared by the R 1216 oxidation style.
Catalyzer of the present invention comprises Primary Catalysts and promotor, and Primary Catalysts is organic amine compound, five yuan or hexa-atomic nitrogenous heterocyclic compounds or hexa-atomic condensed ring class aryl compound, and promotor is for providing F
-The basic metal villiaumite of negatively charged ion.
The organic amine catalyzer steric hindrance of alkalescence is less, can well the open loop effect.The condensed ring compounds, the nitrogen heterocyclic ring compounds, it is very large that cloud density on C becomes, make C be with a certain amount of negative charge, based on repulsive interaction between identical charges, just cause it to push away electronic action, attack raw material Propylene oxide hexafluoride carbon-oxygen bond end, make the epoxy bond fracture, form the C=O carbonyl.Simultaneously, because the electronegativity of oxygen is larger, and hale under electronic action at large C group, the C atom at β seat has to get characteristic electron, and the materials such as the Sodium Fluoride of alkaline inorganic fluoride, Potassium monofluoride, cesium fluoride provide F
-Negatively charged ion forms CF
3CF
2COF
2 -The negative ionization compound.At last, the F of a position
-Ion just is transferred on the inorganic positive ion groups such as sodium, potassium, caesium, forms CF
3CF
2COF and inorganic fluoride.
Organic amine compound is one or more combinations in triethylamine, quadrol, dipropyl amine, tripropyl amine, dimethyl formamide or Tetramethyl Ethylene Diamine preferably.Preferably one or more combinations in quinoline, isoquinoline 99.9, alkyl quinoline of hexa-atomic condensed ring class aryl compound.Described alkyl quinoline is preferably toluquinoline.
Five yuan or preferably one or more combinations in piperidines, Alkylpiperidine, pyridine, tetrahydropyridine, morpholine, alkyl morpholine or alkyl pyrrolidone of hexa-atomic nitrogenous heterocyclic compounds.Described Alkylpiperidine is preferably methyl piperidine, and alkyl morpholine is preferably methylmorpholine, and alkyl pyrrolidone is preferably N-Methyl pyrrolidone.
The present invention's promotor used is the basic metal villiaumite, is preferably Sodium Fluoride, Potassium monofluoride or cesium fluoride, and the quality proportioning of Primary Catalysts and promotor is 100: 1～5: 1, and more suitable proportioning is 30: 1～10: 1.
The temperature of reaction is larger on the speed of response impact, we wish the reaction carry out faster, this just needs to improve temperature of reaction, this reaction simultaneously is heat release, in order to make temperature of reaction within can span of control, the suitable reactions temperature is preferably 20 ℃～150 ℃, and further more excellent is 70 ℃～100 ℃.
The present invention's reaction is reaction with same mole, and reaction pressure is on not impact of speed of response, and higher pressure can increase the residence time of reactant, can make to react carry out more complete, but too high pressure is had relatively high expectations to equipment and reactive system, is not suitable for operation.Therefore, suitable reactions pressure is preferably normal pressure to 1.0Mpa, and further more excellent is 0.2Mpa-0.6Mpa.
Reaction of the present invention both can periodical operation, also can carry out continuously, preferred successive reaction.The present invention's reaction can be carried out in the tank reactor of pressure, also can carry out in the tubular reactor of pressure.More preferably reactor is tubular reactor with pressure, be convenient to like this successive reaction, but require so accurate Controlling System.
The reactor material that the present invention uses need to have erosion resistance preferably, adapt to raw material, catalyst system and product five fluorine propionyl fluoride threes' acting in conjunction, the general erosion resistance fluorine resin preferably of selecting is as tetrafluoroethylene, polyhexafluoropropylene, the contour performance materials of polyvinylidene difluoride (PVDF).Carry out degree in order to increase reaction, improve product yield, should improve reaction pressure, this just need to become reactor design certain requirement of withstand voltage, technical requirements based on top two aspects, reactor design can be become the Steel Pressure Vessels of lining fluorine resin, so both can be corrosion-resistant, again can carrying capacity.
Embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated, but do not limit the invention to these embodiments.One skilled in the art would recognize that the present invention contained all alternativess, improvement project and the equivalents that may comprise in claims scope.
Embodiment 1
Be 0.5L at volume, inner liner polytetrafluoroethylene, in the pressure reaction still of belt stirrer, add 150g quadrol and 10gNaF, then reactor closes, open stirring reaction, stirring velocity is opened heating rising temperature of reaction kettle at 300 rev/mins, and temperature is controlled at 90 ℃, in batches pass into reactor in from liquid-phase tube 200g raw material Propylene oxide hexafluoride after temperature reaches, reaction pressure maintains 0.6MPa, from the gas phase pipe, reaction mass is emitted, and condensation is collected and obtained crude product material 175g, gas phase analysis content in crude product, wherein CF
3CF
2COF content is 92%, product yield 80.5%.
Embodiment 2
Be 0.5L at volume, inner liner polytetrafluoroethylene, in the pressure reaction still of belt stirrer, add 180g quinoline and 10gKF, then reactor closes, open stirring reaction, stirring velocity is opened reactor heating rising temperature of reaction kettle at 300 rev/mins, and temperature is controlled at 100 ℃, in batches pass into reactor in from liquid-phase tube 200g raw material Propylene oxide hexafluoride after temperature reaches, reaction pressure maintains 0.65MPa, from the gas phase pipe, reaction mass is emitted, and condensation is collected and obtained crude product material 186g, gas phase analysis content in crude product, wherein CF
3CF
2COF content is 91%, product yield 84.6%.
Embodiment 3
Be 0.5L at volume, inner liner polytetrafluoroethylene, in the pressure reaction still of belt stirrer, add 160g piperidines and 6gCsF, then reactor closes, open stirring reaction, stirring velocity is opened reactor heating rising temperature of reaction kettle at 300 rev/mins, and temperature is controlled at 90 ℃, in batches pass into reactor in from liquid-phase tube 210g raw material Propylene oxide hexafluoride after temperature reaches, reaction pressure maintains the 0.5MPa left and right, from the gas phase pipe, reaction mass is emitted, and condensation is collected and obtained crude product material 181g, gas phase analysis content in crude product, wherein CF
3CF
2COF content is 93.5%, product yield 81%.
Embodiment 4
Be 1L at volume, liner perfluoroethylene-propylene (being called for short " F46 "), in the pressure reaction still of belt stirrer, add 300gN-methyl-2-pyrrolidone and 20gKF mixed catalyst, then reactor closes, open stirring, stirring velocity is at 250 rev/mins, open heating rising temperature of reaction kettle, temperature is controlled at 95 ℃, in batches passes into reactor in from liquid-phase tube 420g raw material Propylene oxide hexafluoride after temperature reaches, reaction pressure maintains the 0.6MPa left and right, from the gas phase pipe, reaction mass is emitted, condensation is collected and is obtained crude product material 365g, wherein CF
3CF
2COF content is 90.5%, product yield 78.6%.
Embodiment 5
Be 1L at volume, liner F46 is in the pressure reaction still of belt stirrer, add 320g Tetramethyl Ethylene Diamine and 20gNaF mixed catalyst, the reactor that then closes is opened stirring, stirring velocity is at 250 rev/mins, open heating rising temperature of reaction kettle, temperature is controlled at 100 ℃, in batches passes into reactor in from liquid-phase tube 400g raw material Propylene oxide hexafluoride after temperature reaches, reaction pressure maintains the 0.6MPa left and right, from the gas phase pipe, reaction mass is emitted, condensation is collected and is obtained crude product material 360g, wherein CF
3CF
2COF content is 89.7%, product yield 80.7%.
Embodiment 6
With constant-temperature heating sleeve, inner liner polytetrafluoroethylene, diameter are 32mm, be highly in the 1m tubular reactor, add 100g toluquinoline and 5gNaF, reactor then closes, open heating jacket rising temperature of reaction, stop heating up when temperature of reaction to 70 ℃, keep this temperature of reaction.Then the raw material Propylene oxide hexafluoride is at the uniform velocity passed into reactor bottom with 20ml/min, the following reaction product enters into the product-collecting device from reactor head, reaction pressure maintains 0.3MPa, come the detection reaction effect by gas-chromatography, feed stock conversion 96%, product five fluorine propionyl fluoride content are more than 92%, analytical data such as following table.
Embodiment 7
With constant-temperature heating sleeve, inner liner polytetrafluoroethylene, diameter is 32mm, highly in the tubular reactor of 1m, add 110g pyridine and 8gKF, then reactor closes, open heating jacket rising temperature of reaction, when temperature of reaction is raised to 80 ℃, then constant temperature of reaction at the uniform velocity passes into reactor bottom with the raw material Propylene oxide hexafluoride with 30ml/min, reaction product enters into the product-collecting device from reactor head, reaction pressure maintains 0.2MPa, comes the detection reaction effect by gas-chromatography, analytical data such as following table; Feed stock conversion is near 92%, and product five fluorine propionyl fluoride content are more than 90%.
Embodiment 8
with constant-temperature heating sleeve, inner liner polytetrafluoroethylene, diameter is 32mm, highly in the tubular reactor of 1m, add 100g methylmorpholine and 6gNaF, then reactor closes, open heating jacket rising temperature of reactor, constant this temperature during question response temperature to 70 ℃, then the raw material Propylene oxide hexafluoride is at the uniform velocity passed into reactor bottom with 25ml/min, reaction product enters into the product-collecting device from reactor head, reaction pressure maintains 0.2MPa, come the detection reaction effect by gas-chromatography, show that reaction raw materials has not almost had, transformation efficiency is greater than 99%, product five fluorine propionyl fluoride content are more than 94%.
Embodiment 9
with constant-temperature heating sleeve, inner liner polytetrafluoroethylene, diameter is 32mm, highly in the tubular reactor of 1m, add 90g tripropyl amine and 4gCsF, then reactor closes, open heating jacket rising temperature of reactor, the question response temperature is constant temperature after 85 ℃, then the raw material Propylene oxide hexafluoride is at the uniform velocity passed into reactor bottom with 20ml/min, reaction product enters into the product-collecting device from reactor head, reaction pressure maintains 0.3MPa, come detection reaction to collect product by gas-chromatography, analytical data shows that reaction raw materials content is lower, transformation efficiency is greater than 99%, product five fluorine propionyl fluoride content are more than 93%.
Embodiment 10
with constant-temperature heating sleeve, inner liner polytetrafluoroethylene, diameter is 32mm, highly in the tubular reactor of 1m, add 105g methyl piperidine and 6gKF, then reactor closes, open heating jacket rising temperature of reactor, the question response temperature is constant temperature after 85 ℃, then the raw material Propylene oxide hexafluoride is at the uniform velocity passed into reactor bottom with 30ml/min, reaction product enters into the product-collecting device from reactor head, reaction pressure maintains 0.3MPa, come detection reaction to collect product by gas-chromatography, analytical data shows that reaction raw materials content is lower, transformation efficiency is greater than 99%, product five fluorine propionyl fluoride content are more than 92%.
Claims (14)
1. a method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material, is characterized in that, Propylene oxide hexafluoride generation isomerization reaction generates five fluorine propionyl fluorides under catalyst action, and described catalyzer comprises Primary Catalysts and promotor, wherein:
Primary Catalysts is organic amine compound, five yuan or hexa-atomic nitrogenous heterocyclic compounds or hexa-atomic condensed ring class aryl compound;
Promotor is the basic metal villiaumite;
The quality proportioning of Primary Catalysts and promotor is 100: 1～5: 1.
2. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that described organic amine compound is selected from one or more combinations in triethylamine, quadrol, dipropyl amine, tripropyl amine, dimethyl formamide or Tetramethyl Ethylene Diamine.
3. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that described hexa-atomic condensed ring class aryl compound is selected from one or more combinations in quinoline, isoquinoline 99.9, alkyl quinoline.
4. according to the described method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material of claim 3, it is characterized in that described alkyl quinoline is toluquinoline.
According to claimed in claim 1 take Propylene oxide hexafluoride as raw material the method for synthetic five fluorine propionyl fluorides, it is characterized in that described five yuan or hexa-atomic nitrogenous heterocyclic compounds are selected from one or more combinations in piperidines, Alkylpiperidine, pyridine, tetrahydropyridine, morpholine, alkyl morpholine or alkyl pyrrolidone.
6. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 5, it is characterized in that described Alkylpiperidine is methyl piperidine, alkyl morpholine is methylmorpholine, and alkyl pyrrolidone is N-Methyl pyrrolidone.
7. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that described basic metal villiaumite is Sodium Fluoride, Potassium monofluoride or cesium fluoride.
8. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, the quality proportioning that it is characterized in that described Propylene oxide hexafluoride and catalyzer is 1: 1～100: 1.
9. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, the proportioning that it is characterized in that described Primary Catalysts and promotor is 30: 1～10: 1.
10. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that temperature of reaction is 20 ℃～150 ℃, reaction pressure is that normal pressure is to 1.0Mpa.
11. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 8, it is characterized in that temperature of reaction is 70 ℃～100 ℃, reaction pressure is 0.2Mpa～0.6Mpa.
12. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that reactor is tank reactor or the tubular reactor with pressure, liner fluorine resin, described fluorine resin are tetrafluoroethylene, polyhexafluoropropylene or polyvinylidene difluoride (PVDF).
13. according to method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material claimed in claim 1, it is characterized in that reacting and carry out continuously, reaction pressure is 0.1Mpa～0.5Mpa, temperature of reaction is 70 ℃～90 ℃.
14. according to the described method of synthesizing five fluorine propionyl fluorides take Propylene oxide hexafluoride as raw material of claim 13, it is characterized in that reacting in the tubular reactor of pressure and carry out, described tubular reactor liner fluorine resin with pressure, described fluorine resin is tetrafluoroethylene, polyhexafluoropropylene or polyvinylidene difluoride (PVDF).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104000596A CN103145544A (en) | 2011-12-06 | 2011-12-06 | Method for synthesis of pentafluoropropionyl fluoride |
| PCT/CN2012/085604 WO2013083015A1 (en) | 2011-12-06 | 2012-11-30 | Process for synthesizing pentafluoropropionyl fluoride |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011104000596A CN103145544A (en) | 2011-12-06 | 2011-12-06 | Method for synthesis of pentafluoropropionyl fluoride |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016848A (en) * | 2014-06-30 | 2014-09-03 | 黄辉 | Preparation method of pentafluoropropionyl fluoride |
| CN105315150A (en) * | 2014-08-04 | 2016-02-10 | 天津市长芦盐业总公司化工新材料工程技术中心 | Method for preparing perfluoropropionyl fluoride from hexafluoropropylene oxide oligomer |
| CN105541606A (en) * | 2015-12-29 | 2016-05-04 | 天津市长芦化工新材料有限公司 | Synthetic method of perfluoropropanoyl fluoride and preparation method of catalyst applied to reaction |
| CN106631770A (en) * | 2016-12-14 | 2017-05-10 | 天津市长芦化工新材料有限公司 | Method for synthesizing beta-halogen tetrafluoroacyl fluoride |
| CN114014782A (en) * | 2021-10-20 | 2022-02-08 | 化学与精细化工广东省实验室 | Method for continuously preparing heptafluoroisobutyronitrile through amination-dehydration one-pot gas phase |
| CN114773239A (en) * | 2022-05-09 | 2022-07-22 | 浙江巨化技术中心有限公司 | Perfluoro (4-methyl-3, 6-dioxa-7-octene) sulfonyl fluoride and preparation method thereof |
| CN115368232A (en) * | 2022-08-02 | 2022-11-22 | 浙江诺亚氟化工有限公司 | Synthetic method of perfluoro-acyl fluoride |
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| JPS5838231A (en) * | 1981-08-31 | 1983-03-05 | Daikin Ind Ltd | Preparation of pentafluoropropionyl fluoride |
| JPH04134046A (en) * | 1990-09-21 | 1992-05-07 | Nippon Mektron Ltd | Production of perfluoropropionic acid fluoride |
| US5684193A (en) * | 1995-11-13 | 1997-11-04 | Hoechst Aktiengesellschaft | Process for the preparation of perfluoropropionyl fluoride |
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2011
- 2011-12-06 CN CN2011104000596A patent/CN103145544A/en active Pending
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2012
- 2012-11-30 WO PCT/CN2012/085604 patent/WO2013083015A1/en active Application Filing
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| JPS5838231A (en) * | 1981-08-31 | 1983-03-05 | Daikin Ind Ltd | Preparation of pentafluoropropionyl fluoride |
| JPH04134046A (en) * | 1990-09-21 | 1992-05-07 | Nippon Mektron Ltd | Production of perfluoropropionic acid fluoride |
| US5684193A (en) * | 1995-11-13 | 1997-11-04 | Hoechst Aktiengesellschaft | Process for the preparation of perfluoropropionyl fluoride |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016848A (en) * | 2014-06-30 | 2014-09-03 | 黄辉 | Preparation method of pentafluoropropionyl fluoride |
| CN104016848B (en) * | 2014-06-30 | 2016-06-01 | 黄辉 | The preparation method of a kind of five fluorine propionyl fluorides |
| CN105315150A (en) * | 2014-08-04 | 2016-02-10 | 天津市长芦盐业总公司化工新材料工程技术中心 | Method for preparing perfluoropropionyl fluoride from hexafluoropropylene oxide oligomer |
| CN105541606A (en) * | 2015-12-29 | 2016-05-04 | 天津市长芦化工新材料有限公司 | Synthetic method of perfluoropropanoyl fluoride and preparation method of catalyst applied to reaction |
| CN106631770A (en) * | 2016-12-14 | 2017-05-10 | 天津市长芦化工新材料有限公司 | Method for synthesizing beta-halogen tetrafluoroacyl fluoride |
| CN106631770B (en) * | 2016-12-14 | 2019-11-22 | 天津市长芦化工新材料有限公司 | A kind of synthetic method of beta-halogen tetrafluoro propionyl fluoride |
| CN114014782A (en) * | 2021-10-20 | 2022-02-08 | 化学与精细化工广东省实验室 | Method for continuously preparing heptafluoroisobutyronitrile through amination-dehydration one-pot gas phase |
| CN114014782B (en) * | 2021-10-20 | 2023-10-27 | 化学与精细化工广东省实验室 | Method for preparing heptafluoroisobutyronitrile by amination-dehydration one-pot method in gas phase continuous mode |
| CN114773239A (en) * | 2022-05-09 | 2022-07-22 | 浙江巨化技术中心有限公司 | Perfluoro (4-methyl-3, 6-dioxa-7-octene) sulfonyl fluoride and preparation method thereof |
| CN114773239B (en) * | 2022-05-09 | 2024-02-27 | 浙江巨化技术中心有限公司 | Perfluoro (4-methyl-3, 6-dioxa-7-octene) sulfonyl fluoride and preparation method thereof |
| CN115368232A (en) * | 2022-08-02 | 2022-11-22 | 浙江诺亚氟化工有限公司 | Synthetic method of perfluoro-acyl fluoride |
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|---|---|
| WO2013083015A1 (en) | 2013-06-13 |
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Application publication date: 20130612 |