WO2019030527A1 - Compositions comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (hcfo-1233xf) et leurs utilisations - Google Patents

Compositions comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (hcfo-1233xf) et leurs utilisations Download PDF

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Publication number
WO2019030527A1
WO2019030527A1 PCT/GB2018/052267 GB2018052267W WO2019030527A1 WO 2019030527 A1 WO2019030527 A1 WO 2019030527A1 GB 2018052267 W GB2018052267 W GB 2018052267W WO 2019030527 A1 WO2019030527 A1 WO 2019030527A1
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composition
process according
oligomers
catalyst
carried out
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PCT/GB2018/052267
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English (en)
Inventor
Andrew P Sharratt
John Smith
John Mccarthy
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Mexichem Fluor S.A. De C.V.
Mexichem Uk Limited
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Publication of WO2019030527A1 publication Critical patent/WO2019030527A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • 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
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

Definitions

  • 1233xf 3 , 3, 3-trif luoro-2-chioro-prop- 1 -ene will be referred to as 1233xf.
  • 1233xf is known to have utility as, for example, an intermediate in the manufacture of hydrofluoroolefins (HFOs).
  • HFOs hydrofluoroolefins
  • 1233xf is a key intermediate in the manufacture of 2,3,3,3-tetrafluoropropene, which is also known as HFO-1234yf, HFC-1234yf or simply 1234yf.
  • 2,3,3,3-tetrafluoropropene will be referred to as 1234yf.
  • 1233xf oligomers in an amount of less than about 0.5 wt.%.
  • 1233xf readily oligomerises and that it is these oligomers which have been found to lead to a large amount of fouling as detailed above. 1233xf containing significant amounts of 1233xf oligomers is undesirable for contacting with catalysts and HF in order to prepare HFOs unless steps are taken to control the levels of oligomeric products in it.
  • the 1233xf oligomers typically are compounds according to formula I:
  • n 2 to 50.
  • the 1233xf oligomers have a molecular weight of from about 250 to about 2700 g/mol, such as from about 250 to about 2100 g/mol, for example from about 250 or 290 to about 1400 g/mol. It will be appreciated that these oligomers are formed through uncontrolled processes and so the oligomers formed can vary widely in structure.
  • the term 1233xf oligomer then should be understood to include the meaning of oligomers formed from 1233xf repeating units with a variety of end group functionalisation and branching.
  • the 1233xf oligomers typically have a boiling point higher than non-polymerised 1233xf.
  • the oligomers of the composition may have a boiling point of from about 100 D C to about 600°C, such as from about 110°C to about 500°C, for example from about 120°C to about 400°C.
  • the compositions of the invention contain 1233xf oligomers in an amount of less than about 0.45 wt.% or 0.4 wt.%, such as less than about 0.3 wt.%, 0.2 wt.%, 0.1 wt.% or 0.05 wt.%, for example less than about 0.01 wt.%.
  • compositions of the invention typically contain 1233xf oligomers in an amount of at least about 0.0001 wt.% or 0.0002 wt.%, such as at least about 0.0005 wt.%, 0.001 wt.%, 0.002 wt.% or 0.005 wt.%, for example at least about 0.01 wt.%.
  • the upper and lower limits on the amount of 1233xf oligomers in the compositions of the invention referred to in the preceding two paragraphs can be combined in any way.
  • the compositions of the invention contain 1233xf oligomers in an amount of from about 0.0001 wt.% to about 0.5 wt.% or from about 0.0002 wt.% to about 0.45 wt.%, such as from about 0.0005 wt.% to about 0.4 wt.% or from about 0.001 wt.% to about 0.3 wt.%, for example from about 0.002 wt.% to about 0.2 wt.%.
  • compositions of the invention can be obtained by removing some 1233xf oligomers from the compositions, for example by fractional distillation.
  • fractional distillation is currently preferred to other possible methods of removing 1233xf oligomers.
  • adsorbents might be contemplated to separate 1233xf from its oligomers.
  • adsorbents might catalyse the oligomerisation of 1233xf.
  • the distillation can be carried out by any suitable method bearing in mind the boiling point of 1233xf (12-13 °C) and the boiling point of the 1233xf oligomers as described herein.
  • the Examples described hereinafter provide one such method of separating 1233xf from 1233xf oligomers.
  • the content of the 1233xf oligomers in the compositions of the invention can be kept to the low amounts defined herein by the presence of a polymerisation inhibitor.
  • a polymerisation inhibitor is selected from the group consisting of 4-t- butylpyrocatechol, p-methoxyphenol, t-amylphenol, 2,6-di-t-butyl-p-cresol, 2,6-di-t- butylphenol, phenothiazine, 1 , 1 -dipheyl-2-picrylhydrazyl free radical, limonene, quinones (e.g. 1 ,4-benzoquinone), hydroquinones (e.g. t-butylhydroquinone), epoxides, terpenes, amines and mixtures thereof.
  • compositions of the invention contain a polymerisation inhibitor
  • the polymerisation inhibitor is present in an amount of from about 0.005 to about 2 t.%, such as from about 0.01 to about 1 wt.%, for example from about 0.01 to about 0.5 wt.%.
  • the composition of the invention is used relatively quickly following lowering of the concentration of 1233xf oligomers in the composition to acceptable levels (e.g. by fractional distillation).
  • the composition is essentially free of polymerisation inhibitors.
  • composition contains less than about 0.01 wt.% polymerisation inhibitors, such as less than about 0.005 wt.%, for example less than about 0.002 wt.% or 0.001 wt.%, preferably less than about 0.0001 wt.%.
  • compositions of the invention in processes for the manufacture of HFOs can significantly improve the efficiency and economy of such processes.
  • fouling of equipment surfaces such as heat transfer surfaces and column packings typically is reduced when using the compositions of the invention (compared to 1233xf compositions that contain greater quantities of 1233xf oligomers). This reduces the need to shut equipment down for regular cleaning.
  • compositions of the invention in processes for the manufacture of HFOs can also significantly reduce fouling of equipment surfaces, catalysts and/or adsorbents (compared to 1233xf compositions that contain greater quantities of 1233xf oligomers). Replacement of these components is therefore less frequent when using the compositions of the invention, leading to a more economic process and, typically, an increase in the overall yield of the processes.
  • composition in step (a) of the above process of the invention is a composition of the invention as described herein.
  • Providing step (a) may include the removal of 1233xf oligomers from a composition containing 1233xf so as bring the concentration of 1233xf oligomers in the composition to the levels defined herein. Such removal may be achieved by, for example, fractional distillation.
  • any suitable fluorinating agent may be used in step (b), including any suitable source of nucleophilic fluoride, optionally in a polar aprotic solvent.
  • suitable fluorinating agents include HF, NaF, KF and amine:HF complexes such as Olah's reagent.
  • HF is a preferred fluorinating agent.
  • the fluorination product stream comprises HF, HCI and a compound having the formula CF3CFXCH3, wherein X is F or CI.
  • step (b) at least a portion of 1233xf in the provided composition is converted to 1 ,1 ,1 ,2,2-pentafluoropropane (CF3CF2CH3, 245cb), 2-chloro-1 ,1 ,1 ,2-tetrafluoropropane (CF3CFCICH3, 244bb) or mixtures thereof in the fluorination product stream.
  • CF3CF2CH3, 245cb 2-chloro-1 ,1 ,1 ,2-tetrafluoropropane
  • the fluorination product stream may also comprise unreacted 1233xf.
  • step (b) is carried out at a temperature of from about 0 to about 450 °C and a pressure of from 0 to about 30 bara, preferably at a temperature of from about 200 to about 400 °C and a pressure of from about 1 to about 20 bara, more preferably at a temperature of from about 300 to about 380 °C and a pressure of from about 2 to about 20 bara.
  • Steps (b) may be carried out in the liquid phase or the gas phase.
  • step (b) is carried out in the vapour phase.
  • Steps (b) may be carried out batch-wise, semi-continuously or continuously, preferably semi- continuously or continuously.
  • the on-stream time for the process of the invention may vary over a wide range.
  • cleaning of equipment surfaces and/or replacement of components such as catalysts and/or adsorbents typically is less frequent with the process of the invention compared to corresponding processes in which there are higher amounts of 1233xf oligomers present.
  • the on- stream time for the process of the invention typically will range from about 1 to about 1000 hours, such as from about 2 to about 3000 hours, for example from about 5 to about 5000 hours.
  • the catalyst used in step (b) may be any suitable catalyst that is effective to fluorinate 1233xf.
  • Preferred catalysts are those comprising activated carbon, a zero-valent metal, a metal oxide, a metal oxyhalide, a metal halide, or mixtures of the foregoing.
  • a further group of preferred catalysts are transition metals, alkaline earth metals or aluminium.
  • metals e.g. transition metals
  • activated carbon we include any carbon with a relatively high surface area such as from about 50 to about 3000 m 2 or from about 100 to about 2000 m 2 (e.g. from about 200 to about 1500 m 2 or about 300 to about 1000 m 2 ).
  • the activated carbon may be derived from any carbonaceous material, such as coal (e.g. charcoal), nutshells (e.g. coconut) and wood. Any form of activated carbon may be used, such as powdered, granulated and pelleted activated carbon.
  • the chromium or compound of chromium present in the chromia-based catalysts of the invention is an oxide, oxyfluoride and/or fluoride of chromium such as chromium (III) oxide.
  • a preferred chromia-based catalyst is a zinc/chromia catalyst.
  • zinc/chromia catalyst we mean any catalyst comprising chromium or a compound of chromium and zinc or a compound of zinc. Such catalysts are known in the art, see for example EP-A-0502605, EP-A-0773061 , EP-A-0957074 and WO 98/10862.
  • the chromium or compound of chromium present in the zinc/chromia catalysts of the invention is an oxide, oxyfluoride or fluoride of chromium such as chromium oxide.
  • the total amount of the zinc or a compound of zinc present in the zinc/chromia catalysts of the invention is typically from about 0.01% to about 25%, preferably 0.1 % to about 25%, conveniently 0.01 % to 6% zinc, and in some embodiments preferably 0.5% by weight to about 25 % by weight of the catalyst, preferably from about 1 to 10 % by weight of the catalyst, more preferably from about 2 to 8 % by weight of the catalyst, for example about 4 to 6 % by weight of the catalyst.
  • the catalyst conveniently comprises 0.01% to 1%, more preferably 0.05% to 0.5% zinc.
  • the preferred amount depends upon a number of factors such as the nature of the chromium or a compound of chromium and/or zinc or a compound of zinc and/or the way in which the catalyst is made. These factors are described in more detail hereinafter.
  • the amount of zinc or a compound of zinc quoted herein refers to the amount of elemental zinc, whether present as elemental zinc or as a compound of zinc.
  • the zinc/chromia catalysts used in the invention may include an additional metal or compound thereof.
  • the additional metal is a divalent or trivalent metal, preferably selected from nickel, magnesium, aluminium and mixtures thereof.
  • the additional metal is present in an amount of from 0.01 % by weight to about 25 % by weight of the catalyst, preferably from about 0.01 to 10 % by weight of the catalyst.
  • Other embodiments may comprise at least about 0.5 % by weight or at least about 1 % weight of additional metal.
  • the zinc/chromia catalysts used In the present invention may be amorphous. By this we mean that the catalyst does not demonstrate substantial crystalline characteristics when analysed by, for example, X-ray diffraction.
  • the catalysts may be partially crystalline.
  • the catalyst preferably contains from 0.2 to 25 % by weight, more preferably from 0.3 to 10 % by weight, still more preferably from 0.4 to 5 % by weight of the catalyst in the form of one or more crystalline compounds of chromium and/or one or more crystalline compounds of zinc.
  • a catalyst of the invention that has a degree of crystallinity as defined above before use in a fluorination/dehydrohalogenation reaction and will have a degree of crystallinity outside these ranges during or after use in a fluorination/dehydrohalogenation reaction.
  • the percentage of crystalline material in the catalysts of the invention can be determined by any suitable method known in the art. Suitable methods include X-ray diffraction (XRD) techniques. When XRD is used the amount of crystalline material such as the amount of crystalline chromium oxide can be determined with reference to a known amount of graphite present in the catalyst (e.g., the graphite used in producing catalyst pellets) or more preferably by comparison of the intensity of the XRD patterns of the sample materials with reference materials prepared from suitable internationally recognised standards, for example NIST (National Institute of Standards and Technology) reference materials.
  • XRD X-ray diffraction
  • the zinc/chromia catalysts of the invention typically have a surface area of at least 50 m 2 /g and preferably from 70 to 250 m 2 /g and most preferably from 100 to 200 m 2 /g before it is subjected to pre-treatment with a fluoride containing species such as hydrogen fluoride or a fluorinated hydrocarbon. During this pre-treatment, which is described in more detail hereinafter, at least some of the oxygen atoms in the catalyst are replaced by fluorine atoms.
  • Step (c) may be carried out in the liquid phase or the gas phase.
  • step (c) is carried out in the vapour phase.
  • Step (c) may be carried out batch-wise, semi-continuously or continuously, preferably semi- continuously or continuously.
  • Step (c) of the process of the invention may be carried out under any suitable reactions conditions effective to dehydrohalogenate the compound of formula CF3CFXCH3 to produce 1234yf .
  • the dehydrohalogenation may be carried out in the vapour and/or liquid phase and typically is carried out at a temperature of from about -70 to about 1000 °C (e.g. 0 to 400 °C).
  • Step (c) may be carried out at atmospheric sub- or super atmospheric pressure, preferably from about 0 to about 30 bara.
  • step (c) is carried out at a temperature of from about 0 to about 400 °C and a pressure of from 0.01 to about 25 bara, preferably from about 200 to about 360 °C and from about 1 to about 10 bara.
  • Suitable catalysts for step (c) include metal and carbon based catalysts such as those comprising activated carbon, main group (e.g. alumina-based catalysts) and transition metals, such as chromia-based catalysts (e.g. zinc/chromia) or nickel-based catalysts (e.g. nickel mesh).
  • metal and carbon based catalysts such as those comprising activated carbon, main group (e.g. alumina-based catalysts) and transition metals, such as chromia-based catalysts (e.g. zinc/chromia) or nickel-based catalysts (e.g. nickel mesh).
  • chromia-based catalysts e.g. zinc/chromia
  • nickel-based catalysts e.g. nickel mesh.
  • One preferred method of effecting the dehydrohalogenation of the compound of formula CF3CFXCH3 to produce 1234yf is by contacting CF3CFXCH3 with a metal catalyst, such as a chromia
  • step (b) is carried out in a first reactor and step (c) is carried out in a second reactor. It is believed that there are advantages associated with the use of separate reactors for these two steps, including modifying the conditions in each reactor to facilitate the reactions in steps (b) and (c) respectively.
  • step (b) can be carried out in the gas phase and step (c) in the liquid phase.
  • a higher temperature can be used in step (b) compared to step (c).
  • a higher pressure can be used in step (b) compared to step (c).
  • steps (b) and (c) may be carried out in a "one-pot" manner, i.e. simultaneously.
  • steps (b) and (c) are carried out in the presence of different catalysts, the fluorination and dehydrohalogenation reactions may be carried out in two discrete steps, for example using two or more discrete reaction zones or reactors.
  • Any suitable apparatus may be used as a reactor for steps (b) and (c), such as a static mixer, a stirred tank reactor or a stirred vapour-liquid disengagement vessel.
  • the apparatus is made from one or more materials that are resistant to corrosion, e.g. Hastelloy® or Inconel®.
  • the fluorination product stream is subjected to a purification step to remove at least some of the HCI before step (c).
  • a purification step to remove at least some of the HCI before step (c).
  • distillation is used to remove at least some of the HCI.
  • Dehydrohalogenation step (c) may be carried out in the vapour or liquid phase, preferably the vapour phase.
  • a metal catalyst such as a chromia-based (e.g. zinc/chromia) catalyst
  • step (c) preferably is conducted at a temperature of from about 200 to about 360 °C, such as from about 240 to about 340 °C.
  • step (c) preferably is carried out from about 0.01 to about 25 bara or about 0.1 to about 20 bara, such as from about 1 to about 10 bara (e.g. 1 to 5 bara).
  • Fluorination step (b) of the invention preferably is carried out by contacting 1233xf with HF.
  • Step (c) of the invention may be carried out in the presence of HF.
  • HF residual HF from step (b) may be present, and/or HF from a separate feed.
  • step (c) may be carried out in the absence of HF, for example following separation of the compound of formula CF3CFXCH3 from HF prior to step (c), and with no additional co-feed of HF.
  • the fluorination product stream is subjected to a purification step to remove at least some of the HF before step (c).
  • a purification step to remove at least some of the HF before step (c).
  • Techniques that may be used to remove at least some of the HF include distillation, phase separation and scrubbing.
  • step (c) Another way of decreasing the concentration of HF in step (c) relative to step (b) (thereby facilitating the fluorination/dehydrohalogenation reactions in these steps) is by adding a diluent gas (e.g. nitrogen) to step (c).
  • a diluent gas e.g. nitrogen
  • a process for preparing 2,3,3,3-tetrafluoropropene 1234yf comprising the step of fluorination of a composition of the invention as described herein. Such a process can include any of the steps outlined above.
  • This process produced a light fraction comprising 1233xf and a heavy fraction comprising 1233xf oligomers.
  • the level of oligomeric impurities in the crude 1233xf was found to be in the region of 0.5 wt.% to 1.0 wt.%.
  • the heavy oligomeric fraction was analysed by XRF, 1 NMR spectroscopy and TGA-DSC, which confirmed that the heavy fraction was composition of 1233xf oligomers with a boiling range of 130°C to 390°C.
  • Liquid 1233xf (at a rate equivalent to 5 ml/min vapour at room temperature and pressure), either the crude or purified samples described above, and HF (at a rate equivalent to 125 ml/min vapour at room temperature and pressure) were fed to a heated evaporator where they were co-vapourised before the combined vapour stream was fed to a reactor containing fluorinated chromia catalyst (6 g) at 350°C and 5 bara pressure. The products exiting the reactor were periodically sampled and analysed by GC. Great difficulty was encountered when feeding the 1233xf containing high levels of 1233xf oligomers and it was found that the feed evaporator became blocked and had to be cleaned every 24 hours.
  • catalyst performance was very stable when 1233xf with highly reduced levels of 1233xf oligomers was used and a very low reduction in rate of conversion loss was observed as detailed in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne une composition comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (CF3CCI=CH2, 1233xf) et des oligomères 1233xf en une quantité inférieure à environ 0,5 % en poids.L'invention concerne également l'utilisation d'une telle composition dans un procédé de fluoration.
PCT/GB2018/052267 2017-08-09 2018-08-09 Compositions comprenant du 3,3,3-trifluoro-2-chloro-prop-1-ène (hcfo-1233xf) et leurs utilisations WO2019030527A1 (fr)

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GBGB1712775.4A GB201712775D0 (en) 2017-08-09 2017-08-09 Compositions and uses thereof

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WO2019030527A1 true WO2019030527A1 (fr) 2019-02-14

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Citations (3)

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Publication number Priority date Publication date Assignee Title
WO2010095764A1 (fr) * 2009-02-23 2010-08-26 Daikin Industries, Ltd. Procede de preparation de compose alcyne contenant du fluor
WO2012009114A2 (fr) * 2010-06-28 2012-01-19 Honeywell International Inc. Procédé destiné à prolonger la durée de vie d'un catalyseur durant l'hydrofluoration
WO2012066375A1 (fr) * 2010-11-15 2012-05-24 Arkema France Procédé de fabrication de 2-chloro-3,3,3-trifluoropropène (hcfo 1233xf) par fluoration en phase liquide du pentachloropropane

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EP2546224B2 (fr) * 2006-01-03 2023-06-14 Honeywell International Inc. Procédé de production de composés organiques fluorés
GB0806422D0 (en) * 2008-04-09 2008-05-14 Ineos Fluor Holdings Ltd Process
WO2009003084A1 (fr) * 2007-06-27 2008-12-31 Arkema Inc. Procédé pour la fabrication d'hydrofluorooléfines
GB0806419D0 (en) * 2008-04-09 2008-05-14 Ineos Fluor Holdings Ltd Process
WO2011102538A2 (fr) * 2010-02-19 2011-08-25 Daikin Industries, Ltd. Procédé pour la production de 2-chloro-3,3,3-trifluoropropène
WO2011135416A1 (fr) * 2010-04-26 2011-11-03 Arkema France Procédé de fabrication de 2-chloro-3, 3, 3-trifluoropropène (hcfo 1233xf) par fluoration en phase liquide de pentachloropropane
JP6648039B2 (ja) * 2014-02-10 2020-02-14 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． 液相フッ素化反応のための反応器
GB2540427B (en) * 2015-07-17 2017-07-19 Mexichem Fluor Sa De Cv Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf)

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010095764A1 (fr) * 2009-02-23 2010-08-26 Daikin Industries, Ltd. Procede de preparation de compose alcyne contenant du fluor
WO2012009114A2 (fr) * 2010-06-28 2012-01-19 Honeywell International Inc. Procédé destiné à prolonger la durée de vie d'un catalyseur durant l'hydrofluoration
WO2012066375A1 (fr) * 2010-11-15 2012-05-24 Arkema France Procédé de fabrication de 2-chloro-3,3,3-trifluoropropène (hcfo 1233xf) par fluoration en phase liquide du pentachloropropane

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