• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to a process for producing 2-chloro-3,3,3-trifluoropropene comprising the steps of: a) providing a stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro 1,1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene; b) in a reactor, contacting said stream A with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene; characterized in that the electrical conductivity of said stream A supplied in step a) is less than 15 mS / cm.
    公开号:FR3078698A1
    申请号:FR1851955
    申请日:2018-03-07
    公开日:2019-09-13
    发明作者:Laurent Wendlinger；Dominique Deur-Bert；Anne Pigamo
    申请人:Arkema France SA；
    IPC主号:
    专利说明:

    Process for the production of 2-chloro-3,3,3-trifluoropropene
    Technical field of the invention
    The present invention relates to the production of hydrofluoroolefins. More particularly, the present invention relates to the production of 2-chloro-3,3,3trifluoropropene.
    Technological background of the invention
    Halogenated hydrocarbons, in particular fluorinated hydrocarbons such as hydrofluoroolefins, are compounds which have a useful structure as functional materials, solvents, refrigerants, blowing agents and monomers for functional polymers or starting materials for such monomers. Hydrofluoroolefins such as 2,3,3,3-tetrafluoropropene (HFO-1234yf) attract attention because they offer promising behavior as refrigerants with low global warming potential.
    The processes for producing fluoroolefins are usually carried out in the presence of a starting material such as an alkane containing chlorine or an alkene containing chlorine, and in the presence of a fluorinating agent such as hydrogen fluoride. These processes can be carried out in the gas phase or in the liquid phase, with or without the catalyst.
    2-chloro-3,3,3-trifluopropene is known as an intermediate for the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) and as a monomer component for various types of polymers. 2-chloro-3,3,3-trifluopropene can be obtained from a compound such as
    1.1.2.3- tetrachloropropene, 2,3,3,3-tetrachloropropene or 1,1,1,2,3-pentachloropropane.
    WO 2007/079431 a process for the production of 2-chloro-3,3,3trifluopropene in the gas phase in the presence of hydrofluoric acid and a chromium-based catalyst is not known. WO 2012/052797 also discloses a process for producing 2-chloro-
    3.3.3- trifluopropene in the gas phase from 1,1,1,2,3-pentachloropropane and in the presence of HF and a mixed Ni-Cr catalyst.
    There is always a need for processes for producing more efficient 2-chloro-3,3,3trifluopropene.
    Summary of the invention
    The present invention relates to a process for the production of 2-chloro-3,3,3trifluoropropene comprising the steps of:
    a) supply of a stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane,
    1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene;
    b) in a reactor, bringing said stream A into contact with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene; characterized in that the electrical conductivity of said current A supplied in step a) is less than 15 mS / cm.
    The present process makes it possible to optimize and improve the production of 2-chloro-3,3,3trifluoropropene. An electrical conductivity value of less than 15 mS / cm of the current A before the implementation of the fluorination step makes it possible to guarantee optimum efficiency of the reaction in terms of conversion and selectivity. If a catalyst is present, such a value also ensures optimum efficiency of the catalyst.
    According to a preferred embodiment, step b) is carried out in the gas phase in the presence or absence of a catalyst.
    According to a preferred embodiment, step b) is carried out in the liquid phase in the presence of a catalyst.
    According to a preferred embodiment, the electrical conductivity of said current A is less than 10 mS / cm.
    According to a preferred embodiment, step b) is carried out in the presence of a chromium-based catalyst, in particular said catalyst comprises a chromium oxyfluoride or a chromium oxide or a chromium fluoride or a mixture of them.
    According to a preferred embodiment, the catalyst is based on chromium and also comprises a cocatalyst selected from the group consisting of Ni, Zn, Co, Mn or Mg, preferably the cocatalyst content is between 0, 01% and 10% based on the total weight of the catalyst.
    According to a preferred embodiment, stream B comprises, in addition to 2-chloro-3,3,3trifluoropropene, HCl, HF, 2,3,3,3-tetrafluoropropene, and optionally 2,3-dichloro-3,3difluoropropene, 2 , 3,3-trichloro-3-fluoropropene and / or 1,1,1,2,2-pentafluoropropane.
    According to a preferred embodiment, step b) is carried out at a temperature between 320 ° C and 440 ° C.
    According to a preferred embodiment, step b) is carried out in the presence of hydrofluoric acid having an electrical conductivity of less than 10 mS / cm.
    Detailed description of the present invention
    The present invention relates to a process for the production of 2-chloro-3,3,3trifluoropropene comprising the steps:
    a) supply of a stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane,
    1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene;
    b) in a reactor, bringing said stream A into contact with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene.
    According to a preferred embodiment, the electrical conductivity of said current A supplied in step a) is less than 15 mS / cm. Advantageously, the electrical conductivity of said current A supplied in step a) is less than 14 mS / cm, preferably less than 13 mS / cm, more preferably less than 12 mS / cm, in particular less than 11 mS / cm, more particularly less than 10 mS / cm, preferably less than 9 mS / cm, advantageously less than 8 mS / cm, preferably less than 7 mS / cm, more preferably less than 6 mS / cm, particularly preferably less than 5 mS / cm. The electrical conductivity is measured using an inductive conductivity measuring cell and according to the practice known to those skilled in the art. Preferably, the measuring cell is coated with a material resistant to a corrosive medium, in particular resistant to hydrofluoric acid.
    The electrical conductivity of said current A is measured before step b). Preferably, the electrical conductivity of said current A is measured when the latter is in liquid form. Said method according to the present invention may therefore comprise a step of heating and vaporizing said stream A prior to the implementation of step b) to supply said stream A in gaseous form. Preferably, said current A used in step b) is in gaseous form when it is brought into contact with HF.
    According to a preferred embodiment, step b) is carried out in the gas phase in the presence of a catalyst, preferably a catalyst based on chromium. Preferably, the chromium-based catalyst can be a chromium oxide (for example CrCh, CrO3 or C ^ Ch), a chromium oxyfluoride or a chromium fluoride (for example CrFa) or a mixture of these. The chromium oxyfluoride may contain a fluorine content of between 1 and 60% by weight based on the total weight of the chromium oxyfluoride, advantageously between 5 and 55% by weight, preferably between 10 and 52% by weight, more preferably between 15 and 52% by weight, in particular between 20 and 50% by weight, more particularly between 25 and 45% by weight, preferably between 30 and 45% by weight, more preferably between 35 and 45% by weight of fluorine based on the total weight of chromium oxyfluoride. The catalyst can also comprise a co-catalyst chosen from the group consisting of Ni, Co, Zn, Mg, Mn, Fe, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, Sb; preferably Ni, Co, Zn, Mg, Mn; in particular Ni, Co, Zn. The content by weight of the cocatalyst is between 1 and 10% by weight based on the total weight of the catalyst. The catalyst can be supported or not. A support such as alumina, activated alumina, aluminum halides (AIF3 for example), aluminum oxyhalides, activated carbon, magnesium fluoride or graphite can be used.
    Preferably, the catalyst can have a specific surface between 1 and 100 m 2 / g, preferably between 5 and 80 m 2 / g, more preferably between 5 and 70 m 2 / g, ideally between 5 and 50 m 2 / g , in particular between 10 and 50 m 2 / g, more particularly between 15 and 45 m 2 / g.
    According to another preferred embodiment, step b) is carried out in the gas phase in the absence of catalyst.
    When step b) is carried out in the gas phase, in the absence or in the presence of a catalyst, the pressure at which step b) is carried out may be atmospheric pressure or a pressure higher than this. , advantageously the pressure at which step b) is implemented may be greater than 1.5 bara, preferably greater than 2.0 bara, in particular greater than 2.5 bara, more particularly greater than 3.0 bara . Preferably, step b) can be implemented at a pressure between atmospheric pressure and 20 bara, preferably between 2 and 18 bara, more preferably between 3 and 15 bara.
    Preferably, in the gas phase, in the absence or in the presence of a catalyst, step b) of the present process is carried out with a contact time between 1 and 100 s, preferably between 2 and 75 s, in particular between 3 and 50 s. Preferably, the HF molar ratio and said at least one of the compounds of said stream A, ie 2,3-dichloro-l, l, l-trifluoropropane, 1,1,1,2,3pentachloropropane, 1,1,2,3 -tetrachloropropene and 2,3,3,3-tetrachloropropene, can vary between 1: 1 and 150: 1, preferably between 2: 1 and 125: 1, more preferably between 3: 1 and 100: 1. An oxidant, such as oxygen or chlorine, can be added during step b). The molar ratio of the oxidant to the hydrocarbon compound can be between 0.005 and 2, preferably between 0.01 and 1.5. The oxidant can be pure oxygen, air or a mixture of oxygen and nitrogen.
    According to a preferred embodiment, in the gas phase, in the absence or in the presence of a catalyst, step b) is carried out at a temperature between 320 ° C and 440 ° C, advantageously between 320 ° C and 420 ° C, preferably between 330 ° C and 400 ° C, more preferably between 330 ° C and 390 ° C, in particular between 340 ° C and 380 ° C.
    According to a preferred embodiment, step b) can be implemented in the liquid phase. Preferably, step b) is carried out in the liquid phase and in the presence of a catalyst. The catalyst can be a Lewis acid, a catalyst containing a halide of a metal, in particular an halide of antimony, tin, tantalum, titanium, of a transition metal such as molybdenum, niobium, iron, cesium, transition metal oxides, group IVb metal halides, group Vb metal halides, chromium fluoride, fluorinated chromium oxides or a mixture thereof. For example, the catalyst can be SbCI 5 , SbCL, TiCL, SnCL, TaCI 5 , NbCI 5 , TiCL, FeCL, MoCk, CsCI, and the corresponding fluorinated compounds. The catalyst can contain an ionic liquid as described for example in applications WO2008 / 149011 (in particular from page 4, line 1 to page 6 line 15, included by reference) and WOOl / 81353, as well as the reference "liquid -phase HF Fluorination, Multiphase Homogeneous Catalysis, Ed. Wiley-VCH, (2002), 535.
    In the liquid phase, step b) can be carried out at a temperature between 30 and 200 ° C, advantageously between 40 ° C and 170 ° C, preferably between 50 and 150 ° C. Preferably, the HF / starting materials molar ratio can be from 0.5: 1 to 50: 1, advantageously from 3: 1 to 20: 1 and preferably from 5: 1 to 15: 1. The term “starting materials” refers to said at least one of the compounds selected from the group consisting of 2,3-dichloro-l, l, ltrifluoropropane, 1,1,1,2,3-pentachloropropane, 1,1,2 , 3-tetrachloropropene and 2,3,3,3tetrachloropropene.
    According to a preferred embodiment, the stream A can be mixed with hydrofluoric acid before step b). Thus, step a) of the present method can comprise the steps:
    al) supply of a gas stream comprising hydrofluoric acid;
    a2) supply of said stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3pentachloropropane, 1,1,2,3- tetrachloropropene and 2,3,3,3-tetrachloropropene and having an electrical conductivity less than 15 mS / cm;
    a3) spraying said stream A to form droplets with an average diameter of less than 500 μm;
    a4) vaporization of said droplets produced in step a3) by mixing with said gas flow supplied in step a1), the resulting mixture being a gaseous mixture.
    The gas mixture thus produced in step a4) is used in step b) of the present process to allow the production of 2-chloro-3,3,3-trifluoropropene.
    The present process can thus include the steps of:
    al) supply of a gas stream comprising hydrofluoric acid;
    a2) supply of said stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3pentachloropropane, 1,1,2,3- tetrachloropropene and 2,3,3,3-tetrachloropropene and having an electrical conductivity less than 15 mS / cm;
    a3) spraying said stream A to form droplets with an average diameter of less than 500 μm;
    a4) vaporization of said droplets produced in step a3) by mixing with said gas flow supplied in step a1), the resulting mixture being a gaseous mixture;
    b) in a reactor, bringing said gas mixture from step a4) into contact with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-
    3,3,3-trifluoropropene.
    According to a preferred embodiment, stream B comprises, in addition to 2-chloro-3,3,3trifluoropropene, HCl, HF, 2,3,3,3-tetrafluoropropene. Stream B can optionally include 2,3-dichloro-3,3-difluoropropene, 2,3,3-trichloro-3-fluoropropene and / or 1,1,1,2,2pentafluoropropane.
    According to a preferred embodiment, stream B is purified, preferably by distillation, to form a first stream comprising 2,3,3,3-tetrafluoropropene, HCl and optionally 1,1,1,2,2-pentafluoropropane, and a second stream comprising HF and 2-chloro-3,3,3-trifluoropropene and optionally 2,3-dichloro-3,3-difluoropropene and 2,3,3 trichloro-3-fluoropropene. In particular, the distillation can be carried out at a pressure of 2 to 6 bara, more particularly at a pressure of 3 to 5 bara. In particular, the temperature at the top of the distillation column is from -35 ° C to 10 ° C, preferably from -20 ° C to 0 ° C.
    According to a preferred embodiment, said stream B obtained in step b) is cooled before the purification mentioned above. In particular, said stream B obtained in step b) is cooled to a temperature below 100 ° C., then distilled to form said first stream comprising 2,3,3,3-tetrafluoropropene, HCl and optionally 1,1,1 , 2,2pentafluoropropane, and said second stream comprising HF and 2-chloro-3,3,3-trifluoropropene and optionally 2,3-dichloro-3,3-difluoropropene and 2,3,3-trichloro-3-fluoropropene; the temperature at the top of the distillation column is from -35 ° C to 10 ° C and the distillation is carried out at a pressure of 2 to 6 bara.
    Said stream B can be cooled, before distillation, to a temperature below 95 ° C, advantageously below 90 ° C, preferably below 85 ° C, more preferably below 80 ° C, in particular below 70 ° C, more particularly less than 60 ° C, preferably less than 55 ° C, advantageously less than 50 ° C, preferably less than 40 ° C, more preferably less than 30 ° C, so particularly preferred less than 25 ° C, more particularly preferred less than 20 ° C. Cooling the product stream obtained to such temperatures can facilitate subsequent distillation.
    The cooling of said stream B can be carried out by means of one or a plurality of heat exchangers. The cooling of said stream B can be carried out by passing it through one, two, three, four, five, six, seven, eight, nine or ten heat exchangers, preferably the number of heat exchangers is between 2 and 8, in particular between 3 and 7.
    Said second stream comprising HF and 2-chloro-3,3,3-trifluoropropene and optionally 2,3-dichloro-3,3-difluoropropene and 2,3,3-trichloro-3-fluoropropene can be purified, preferably by distillation , to form a third stream comprising hydrofluoric acid and optionally 2,3-dichloro-3,3-difluoropropene and 2,3,3-trichloro-3fluoropropene, and a fourth stream comprising at least 95% by weight of 2-chloro -3,3,3trifluoropropene, preferably at least 98% by weight of 2-chloro-3,3,3-trifluoropropene based on the total weight of said fourth stream.
    The third stream comprising hydrofluoric acid and optionally 2,3-dichloro-
    3,3-difluoropropene and 2,3,3-trichloro-3-fluoropropene can be recycled in step b) or in step al) of the present process. In this case, said third stream is mixed with hydrofluoric acid before being used in step b) or in step al) of the present process.
    According to a preferred embodiment, step b) is carried out in the presence of hydrofluoric acid having an electrical conductivity of less than 10 mS / cm, preferably less than 5 mS / cm. The electrical conductivity of hydrofluoric acid can be measured prior to its use in step b) or step al) of the present process. Preferably, the electrical conductivity of hydrofluoric acid is measured prior to step b) or step a1) and the hydrofluoric acid is in liquid form during the measurement. The method can also include a step of heating and vaporizing hydrofluoric acid prior to the implementation of step b) to provide hydrofluoric acid in gaseous form. Preferably, the hydrofluoric acid is in gaseous form when it is brought into contact with said stream A.
    According to a particular embodiment, the method can include the steps of:
    al) supply of a gas stream comprising hydrofluoric acid having an electrical conductivity of less than 10 mS / cm;
    a2) supply of said stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3pentachloropropane, 1,1,2,3- tetrachloropropene and 2,3,3,3-tetrachloropropene and having an electrical conductivity less than 15 mS / cm;
    a3) spraying said stream A to form droplets with an average diameter of less than 500 μm;
    a4) vaporization of said droplets produced in step a3) by mixing with said gas flow supplied in step a1), the resulting mixture being a gaseous mixture;
    b) in a reactor, bringing said gas mixture from step a4) into contact with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-3,3,3trifluoropropene.
    Preferably, the method according to the present invention is implemented continuously. Preferably, the method according to the present invention is implemented in the gas phase.
    Example
    The fluorination of HCC-240db (1,1,1,2,3-pentachloropropane) to HCFO-1233xf (2-chloro-
    3,3,3-trifluoropropene) is produced in a multitubular reactor. The reactor contains a mass catalyst based on chromium oxide. The catalyst is activated by a series of stages including drying, fluorination, treatment in air and fluorination with recycling. This treatment in several stages makes the catalytic solid active and selective.
    The fluorination process is carried out according to the following operating conditions: An absolute pressure in the fluorination reactor of 5.5 bar absolute
    A molar ratio between HF and the sum of the organics supplied by the recycling loop of between 12 and 15
    Contact time between 11 and 13 seconds
    A constant temperature in the reactor of 350 ° C.
    The method is implemented with a current of HCC-240db having two values of different electrical conductivity: 6 and 25 mS / cm. The run is stopped when the conversion to
    1,1,1,2,3-pentachloropropane is less than 50%. Table 1 below shows the values obtained. The electrical conductivity of the HCC-240db current is measured using a cell marketed by Endress + Hauser and referenced under the term InduMax P CLS 50 coated with a polymer coating of perfluoroalkoxy type (PFA) resistant to a corrosive medium. containing HF.
    Table 1
    Example Electrical conductivity (mS / cm) Duration of the run to reach a conversion <50% (h) 1 (inv.) 6 460 2 (comp.) 25 100
    The results detailed in Table 1 demonstrate that a current comprising HCC240db and having an electrical conductivity of less than 15 mS / cm makes it possible to maintain a sufficiently high conversion for a long period of time. In fact, a conversion greater than 50% can be maintained for more than 460 h (example 1). Conversely, the conversion to HCC-240db drops sharply when the electrical conductivity is too high (example 2).
    权利要求:
    Claims (9)
    [1" id="c-fr-0001]
    claims
    1. Process for the production of 2-chloro-3,3,3-trifluoropropene comprising the steps of:
    a) supply of a stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane,
    1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene;
    b) in a reactor, bringing said stream A into contact with HF in the presence or absence of a catalyst to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene; characterized in that the electrical conductivity of said current A supplied in step a) is less than 15 mS / cm.
    [2" id="c-fr-0002]
    2. Method according to claim 1 characterized in that step b) is implemented in the gas phase in the presence or not of a catalyst.
    [3" id="c-fr-0003]
    3. Method according to any one of the preceding claims, characterized in that step b) is carried out in the liquid phase in the presence of a catalyst.
    [4" id="c-fr-0004]
    4. Method according to any one of the preceding claims, characterized in that the electrical conductivity of said current A is less than 10 mS / cm.
    [5" id="c-fr-0005]
    5. Method according to any one of the preceding claims, characterized in that step b) is carried out in the presence of a chromium-based catalyst, in particular said catalyst comprises a chromium oxyfluoride or a chromium oxide or a chromium fluoride or a mixture thereof.
    [6" id="c-fr-0006]
    6. Method according to the preceding claim characterized in that the catalyst is based on chromium and also comprises a co-catalyst selected from the group consisting of Ni, Zn, Co, Mn or Mg, preferably the content of co-catalyst is between 0.01% and 10% based on the total weight of the catalyst.
    [7" id="c-fr-0007]
    7. Method according to any one of the preceding claims, characterized in that the stream B comprises, in addition to 2-chloro-3,3,3-trifluoropropene, HCl, HF, 2,3,3,3 tetrafluoropropene, and optionally 2, 3-dichloro-3,3-difluoropropene, 2,3,3-trichloro-3fluoropropene and / or 1,1,1,2,2-pentafluoropropane.
    [8" id="c-fr-0008]
    8. Method according to any one of the preceding claims, characterized in that step 5 b) is carried out at a temperature between 320 ° C and 440 ° C.
    [9" id="c-fr-0009]
    9. Method according to any one of the preceding claims, characterized in that step b) is carried out in the presence of hydrofluoric acid having an electrical conductivity of less than 10 mS / cm.
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    同族专利:
    公开号 | 公开日
    US11028027B2|2021-06-08|
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    WO2019170990A1|2019-09-12|
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    FR3023286B1|2014-07-02|2018-02-16|Arkema France|PROCESS FOR THE PRODUCTION OF TETRAFLUOROPROPENE|
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    FR3078699B1|2018-03-07|2020-02-21|Arkema France|PROCESS FOR PRODUCING 2,3,3,3-TETRAFLUOROPROPENE|FR3078700B1|2018-03-07|2020-07-10|Arkema France|PROCESS FOR PRODUCING 2,3,3,3-TETRAFLUOROPROPENE|
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    FR3081158B1|2018-05-16|2020-07-31|Arkema France|PROCESS FOR THE PRODUCTION OF 1-CHLORO-3,3,3-TRIFLUOROPROPENE.|
    法律状态:
    2019-02-13| PLFP| Fee payment|Year of fee payment: 2 |
    2019-09-13| PLSC| Publication of the preliminary search report|Effective date: 20190913 |
    2020-02-14| PLFP| Fee payment|Year of fee payment: 3 |
    2021-02-10| PLFP| Fee payment|Year of fee payment: 4 |
    2022-02-09| PLFP| Fee payment|Year of fee payment: 5 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1851955|2018-03-07|
    FR1851955A|FR3078698B1|2018-03-07|2018-03-07|PROCESS FOR PRODUCTION OF 2-CHLORO-3,3,3-TRIFLUOROPROPENE|FR1851955A| FR3078698B1|2018-03-07|2018-03-07|PROCESS FOR PRODUCTION OF 2-CHLORO-3,3,3-TRIFLUOROPROPENE|
    CN201980015035.3A| CN111757863A|2018-03-07|2019-03-04|Production process of 2-chloro-3, 3, 3-trifluoropropene|
    US16/976,520| US11028027B2|2018-03-07|2019-03-04|Process for producing 2-chloro-3,3,3-trifluoropropene|
    EP19715970.0A| EP3762354A1|2018-03-07|2019-03-04|Process for producing 2-chloro-3,3,3-trifluoropropene|
    PCT/FR2019/050478| WO2019170990A1|2018-03-07|2019-03-04|Process for producing 2-chloro-3,3,3-trifluoropropene|
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