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    • 专利摘要:
    The invention relates to a process for the production of 2,3,3,3-tetrafluoropropene carried out starting from a starting composition comprising the steps of contacting, in the presence of a catalyst, the composition of starting with HF to produce a composition A comprising 2,3,3,3-tetrafluoropropene (1234yf), intermediate products B consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,2 2-pentafluoropropane (245cb), and by-products C E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE), trans-1,3,3,3-tetrafluoro-1 propene (1234zeE) and 1,1,1,3,3-pentafluoropropane (245fa); recovering said composition A and purifying it to form and recover a first stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) ) and / or 1,1,1,2,2-pentafluoropropane (245cb); recycling in step a) said one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb), characterized in that the the content of at least one of the secondary products C in said one or more recycled streams in step a) is less than this in said composition A.
    公开号:FR3046164A1
    申请号:FR1563168
    申请日:2015-12-23
    公开日:2017-06-30
    发明作者:Dominique Deur-Bert；Joaquin Lacambra；Laurent Wendlinger；Bertrand Collier
    申请人:Arkema France SA；
    IPC主号:
    专利说明:

    The invention relates to a process for purifying 2,3,3,3-tetrafluoro-1-propene. In addition, the invention also relates to a method for producing and purifying 2,3,3,3-tetrafluoro-1-propene.
    Technological background of the invention
    Hydrofluorocarbons (HFCs) and in particular hydrofluoroolefins (HFOs), such as 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), are compounds known for their properties as refrigerants and heat-transfer fluids, extinguishers, propellants, foaming agents, blowing agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, abrasive agents, drying agents and fluids for power generation units. HFOs have been identified as desirable alternatives to HCFC because of their low ODP (Ozone Potential Depletion or Ozone Depletion Potential) and GWP (Global Warming Potential) values.
    Most of the hydrofluoroolefin manufacturing processes involve a fluorination and / or dehydrohalogenation reaction. This type of reaction is carried out in the gas phase and generates impurities which must therefore be eliminated in order to obtain the desired compound in a degree of purity sufficient for the intended applications.
    For example, in the production of 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), the presence of impurities such as 1-chloro-3,3,3-trifluoro-1 propene (1233zd), 1.3.3.3-tetrafluoro-1-propene (1234ze) and 1,1,1,3,3-pentafluoropropane (245fa) are observed. These impurities are isomers of the main compounds to be obtained by the process for producing 2,3,3,3-tetrafluoro-1-propene in addition to the latter, ie 2-chloro-3,3,3-trifluoro-1-propene ( 1233xf) and 1,1,1,2,2-pentafluoropropane (245cb). Considering the respective boiling points of 1-chloro-3,3,3-trifluoro-1-propene (1233zd), 1,3,3,3-tetrafluoro-1-propene (1234ze) and 1,1, 1,3,3-pentafluoropropane (245fa), these can accumulate in the reaction loop and thus prevent the formation of the products of interest.
    The purification of this type of reaction mixture can be carried out by various techniques known from the prior art, such as, for example, distillation. However, when the compounds to be purified have boiling points too close or when they form azeotropic or quasi-azeotropic compositions, distillation is not an effective method. Extractive distillation processes have thus been described.
    EP 0 864 554 discloses a process for purifying a mixture comprising 1.1.1.3.3-pentafluoropropane (245fa) and 1-chloro-3,3,3-trifluoro-trans-1-propene (1233zd) by distillation in presence of a solvent having a boiling point higher than that of 1-chloro-3,3,3-trifluoro-trans-1-propene.
    WO 03/068716 discloses a process for recovering pentafluoroethane from a mixture comprising pentafluoroethane and chloropentafluoroethane by distillation in the presence of hexafluoropropene.
    WO 98/19982 also discloses a process for purifying 1,1-difluoroethane by extractive distillation. The method comprises contacting an extractant with a mixture of 1,1-difluoroethane and vinyl chloride. The extraction agent is chosen from hydrocarbons, alcohols and chlorocarbons having a boiling point of between 10 ° C. and 120 ° C.
    As mentioned by WO 98/19982, the selection of the extraction agent can be complex depending on the products to be separated. There is therefore still a need for the implementation of a particular method for purifying 2,3,3,3-tetrafluoro-1-propene. Summary of the invention
    In a process for producing 2,3,3,3-tetrafluoro-1-propene, the choice of particular operating conditions may favor the presence of certain impurities or isomers thereof. The presence of impurities such as 1,3,3,3-tetrafluoro-1-propene (1234ze) can be observed just like that of 1-chloro-3,3,3-trifluoro-1-propene (1233zd), and 1,1,1,3,3-pentafluoropropane (245fa). These impurities may arise from secondary reactions induced by intermediately produced compounds during the production of 2,3,3,3-tetrafluoro-1-propene, and may have physical properties such that their removal may be complex. The present invention makes it possible in particular to produce 2,3,3,3-tetrafluoro-1-propene with improved purity.
    According to a first aspect, the invention provides a process for the production and purification of 2,3,3,3-tetrafluoropropene (1234yf) carried out starting from a starting composition comprising at least one compound of formula CX (Y 2-CX (Y) m-CHmXY (I) wherein X and Y are independently H, F, or Cl and m = 0 or 1; and / or fluorinating in the presence of a catalyst of a compound of the formula (CXnY3-n) CHpXi-pCHmX2-m (II) wherein X is independently of each other Cl, F, I or Br; Y is independently of each other H, Cl, F, I or Br; n is 1, 2 or 3; and m is 0, 1 or 2; and p is 0 or 1; said process comprising the steps of: a) contacting, in the presence of a catalyst, the starting composition with HF to produce a composition A comprising 2,3,3,3-tetrafluoropropene (1234yf), intermediate products B consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,2,2-pentafluoropropane (245cb), and by-products C consisting of 1-chloro-3,3,3-trifluoro 1-propene (1233zdE), trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) and 1,1,1,3,3-pentafluoropropane (245fa); b) recovering said composition A and purifying it to form and recover a first stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb); c) recycling in step a) said one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb), characterized in that the content of at least one of the secondary products C in said one or more recycled streams in step a) is less than this in said composition A.
    Preferably, according to the process of the present invention: composition A also comprises HCl, a part of the unreacted HF; and purifying said composition A carried out in step b) comprising the distillation of said composition A to recover at the top of the distillation column a gaseous stream G1 comprising HCl and 2,3,3,3-tetrafluoropropene (1234yf); and at the bottom of the distillation column a liquid stream L1 comprising said part of unreacted HF; all or part of the intermediate products B and all or part of the secondary products C being contained in said gas stream G1 and / or in said liquid stream L1.
    According to a preferred embodiment, said gaseous stream G1 comprises part of the intermediate products B and a portion of the by-products C, and said gaseous stream G1 is purified by the following steps: b1) distillation of the gaseous stream G1 to recover a current G1 comprising HCl, advantageously at the top of the distillation column, and a stream Glb comprising 2,3,3,3-tetrafluoropropene (1234yf), said part of the intermediate products B and said part of the byproducts C, advantageously at the bottom of distillation column; b2) distilling said current Glb obtained in step b1) to form a current Glc comprising 2,3,3,3-tetrafluoropropene (1234yf), a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the top of the distillation column, and a stream Gld comprising a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the bottom of the distillation column.
    Preferably, the current Glc formed in step b2) may comprise 2,3,3,3-tetrafluoropropene (1234yf), 1,1,1,2,2-pentafluoropropane (245cb) andtrans-1, 3,3, 3-tetrafluoro-1-propene (1234zeE). Preferably, the stream G1 1 formed in step b2) may comprise 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE), 2 chloro-3,3,3-trifluoropropene (1233xf). In particular, the content of 1,1,1,2,2-pentafluoropropane (245cb) is greater in the Gld current than in the Glc current.
    According to a preferred embodiment, the process comprises a step b3), subsequent to step b2), wherein the current Glc obtained in step b2) comprises 2,3,3,3-tetrafluoropropene (1234yf), 1 1,1,2,2-pentafluoropropane (245cb) and trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE); and said Glc stream is distilled to form a Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and a Gif stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and a trans-1,3,3,3-tetrafluoropropene stream. tetrafluoro-1-propene (1234zeE). Preferably, the Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) may be subjected to subsequent purification steps to obtain a degree of purity sufficient for marketing.
    According to a preferred embodiment, the current Gif obtained in step b3) is separated by extractive distillation.
    According to a particular embodiment, the current Gif obtained in step b3) is separated by extractive distillation according to the steps: b4) contacting said Gif stream obtained in step b3) with an organic extraction agent to form a current Glg, and b5) extractive distillation of the current Glg to form a flux Glh comprising 1,1,1,2,2-pentafluoropropane (245cb), advantageously at the top of the distillation column, and a stream Gli comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE) and said organic extraction agent, advantageously at the bottom of the distillation column.
    Preferably, the Gli stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) and said organic extractant is separated by distillation to form a stream G1 comprising said organic extractant and a Glk stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE). The current Glj comprising said organic extraction agent can be recycled in step b4). The Glk stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) can be either purified or destroyed by incineration.
    Preferably, the Glh flux comprising 1,1,1,2,2-pentafluoropropane (245cb), preferably free of trans-1,3,3,3-tetrafluoro-1-propene (1234zeE), is recycled to the step a).
    Alternatively, said current Glc is distilled by extractive distillation to form a Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb); a Gif stream comprising trans-1,1,3,3-tetrafluoro-1-propene (1234zeE). Preferably, the Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb) may be subjected to subsequent purification steps. Thus, 2,3,3,3-tetrafluoropropene (1234yf) can be separated from 1,1,1,2,2-pentafluoropropane (245cb), the latter being recycled in step a). 2,3,3,3-Tetrafluoropropene (1234yf) can be further subjected to purification steps in order to obtain a degree of purity sufficient for marketing.
    According to another preferred embodiment, said liquid stream L1 comprises, in addition to the unreacted HF, all or part of the intermediate products B and all or part of the secondary products C; and all or part of this stream L1 is heated at low temperature, advantageously between -50 ° C. and 15 ° C., preferably between -30 ° C. and 0 ° C., to form a first phase Lia comprising part of the HF n ' unreacted and a second phase Llb comprising said intermediate products B and said secondary products C; optionally or not, said current G11 formed in step b2) is mixed with the liquid stream L1 before the latter is heated to a low temperature.
    Preferably, said first phase Lia is recycled in step a).
    According to a preferred embodiment, said second phase Llb is distilled to recover a Lie stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene ( 1234zeE), advantageously at the top of the distillation column, and a stream Lld comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), 1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa); advantageously at the bottom of the distillation column, advantageously said Lie stream is recycled in step a).
    According to a preferred embodiment, said Lld stream is separated to form a stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and a stream comprising E1-chloro-3.3.3-trifluoro-1. propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa).
    According to a preferred embodiment, the separation of said Lld current is carried out by extractive distillation.
    According to a particular embodiment, the extractive distillation of said stream Lld comprises the steps of: contacting said stream Lld with an organic extraction agent to form a composition Lie, and extractive distillation of the composition Lie to form a stream Llf comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), advantageously at the top of the distillation column, and a stream Llg comprising E1-chloro-3,3,3-trifluoro-1-propene ( 1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) and said organic extraction agent, advantageously at the bottom of the distillation column.
    Preferably, the stream L1 is then separated by distillation to form a stream L1 comprising said organic extraction agent and a stream L1 comprising E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1 3,3-pentafluoropropane (245fa). The current Llh can be recycled to be contacted with a current Lld to form a composition Lie. Lli stream comprising E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) can be either purified or destroyed by incineration.
    Preferably, the Llf stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), preferably free of 1,1,1,3,3-pentafluoropropane (245fa) and chlorobenzene 3,3,3-trifluoro-1-propene (1233zdE) is recycled in step a).
    According to a preferred embodiment, the present invention thus allows the recycling in step a) of one or more streams devoid of one or more secondary products C.
    Brief description of the drawings
    FIG. 1 schematically represents a device implementing a process for producing 2,3,3,3-tetrafluoro-1-propene according to one particular embodiment of the present invention.
    Figures 2 and 3 show schematically a device implementing the purification of 2-3,3,3-tetrafluoro-1-propene according to a particular embodiment of the present invention.
    Detailed description of the invention
    The present invention allows the production and purification of 2,3,3,3-tetrafluoropropene (1234yf). According to a first aspect of the present invention, a process for producing and purifying 2,3,3,3-tetrafluoropropene (1234yf) is provided. Said process is carried out starting from a starting composition comprising at least one compound of formula CX (Y) 2-CX (Y) m-CHmXY (I) in which X and Y independently represent H, F, or Cl and m = 0 or 1; and / or fluorinating in the presence of a catalyst of a compound of the formula (CXnY3-n) CHpXi-pCHmX2-m (II) wherein X is independently of each other Cl, F, I or Br; Y is independently of each other H, Cl, F, I or Br; n is 1, 2 or 3; and m is 0.1 or 2; and p is 0 or 1.
    Preferably, said process comprises the steps of: a) contacting, in the presence of a catalyst, the starting composition with HF to produce a composition A comprising 2,3,3,3-tetrafluoropropene (1234yf), intermediate products B consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,2,2-pentafluoropropane (245cb), and by-products C consisting of 1-chloro-3,3, 3-trifluoro-1-propene (1233zd), 1,3,3,3-tetrafluoro-1-propene (1234ze) and 1,1,1,3,3-pentafluoropropane (245fa); b) recovering said composition A and purifying it to form and recover a first stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb); c) recycling in step a) of said one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb).
    Preferably, the content of at least one of the secondary products C in said one or more recycled streams in step a) may be less than this in said composition A.
    The content of any of the by-products C can be decreased in one or more or all of said one or more recycle streams in step a). Preferably, said content of at least one of the secondary products C in said one or more recycled streams in step a) can be decreased by 20%, 30%, 40%, 50%, 60%, 70%, 80% , 90%, 95% or 98% with respect to said content of the same at least one of the by-products C in said composition A. Thus, the content of E-chloro-3,3,3-trifluoro-1-propene (1233zdE ) in said one or more recycled streams in step a) can be decreased by 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95% or 98% with respect to the content of E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) in said composition A. According to another embodiment, the content of trans-1, 3,3,3-tetrafluoro-1- propene (1234zeE) in said one or more recycled streams in step a) can be decreased by 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95% or 98% relative to the content of trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) in said composition A. According to another embodiment, the content of 1,1,1,3 , 3-pentafluoropropane (245fa) in said one or more recycled streams in step a) can be decreased by 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95% or 98% relative to the content of 1,1,1,3,3-pentafluoropropane (245fa) in said composition A. The contents are expressed by weight.
    Said one or more recycled streams in step a) may be devoid of one or more of the side products C. The term "lacking" means that the current under consideration comprises less than 50 ppm, preferably less than 20 ppm, preferably less 10 ppm of the title compound based on the total weight of said stream.
    According to a preferred embodiment, composition A also comprises HCl, part of HF. Preferably, the purification of said composition A carried out in step b) comprises the distillation of said composition A to recover at the top of the column. distilling a gaseous stream G1 comprising HCl and 2,3,3,3-tetrafluoropropene (1234yf); and at the bottom of the distillation column a liquid stream L1 comprising said part of the HF. All or part of the intermediates B and all or part of the secondary products C may be contained in said gaseous stream G1 and / or in said liquid stream L1.
    Preferably, all or part of 1,1,1,2,2-pentafluoropropane (245cb) may be contained in said gas stream G1. All or part of 1,1,1,2,2-pentafluoropropane (245cb) may also be contained in said liquid stream L1.
    Preferably, all or part of trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) may be contained in said gas stream G1. All or part of trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE) can also be contained in said liquid stream L1.
    Preferably, all or part of 2-chloro-3,3,3-trifluoropropene (1233xf) may be contained in said gas stream G1. All or part of the 2-chloro-3,3,3-trifluoropropene (1233xf) may also be contained in said liquid stream L1. In a preferred manner, 2-chloro-3,3,3-trifluoropropene (1233xf) is contained in said liquid stream L1, advantageously 70%, 75%, 80%, 85% or 90% of the 2-chloro-3,3 , 3-trifluoropropene (1233xf) is contained in said liquid stream L1 with respect to said gas stream G1.
    Preferably, all or part of E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) may be contained in said gas stream G1. All or part of E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) can also be contained in said liquid stream L1. In a preferred manner, the E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) is contained in said liquid stream L1, advantageously 70%, 75%, 80%, 85%, 90% or 95% of the 1-chloro-3,3,3-trifluoro-1-propene (1233zd) is contained in said liquid stream L1 with respect to said gas stream G1.
    Preferably, all or part of 1,1,1,3,3-pentafluoropropane (245fa) may be contained in said gas stream G1. All or part of 1,1,1,3,3-pentafluoropropane (245fa) may also be contained in said liquid stream L1. In a preferred manner, 1,1,1,3,3-pentafluoropropane (245fa) is contained in said liquid stream L1, advantageously 70%, 75%, 80%, 85%, 90% or 95% of 1,1, 1,3,3-pentafluoropropane (245fa) is contained in said liquid stream L1 with respect to said gas stream G1.
    According to a preferred embodiment, said gas stream G1 comprises part of the intermediate products B and a portion of the by-products C, and said g gas stream is purified by the following steps: b1) distillation of the gas stream G1 to recover a current Gla comprising HCl, advantageously at the top of the distillation column, and a stream Glb comprising 2,3,3,3-tetrafluoropropene (1234yf), said part of the intermediate products B and said part of the byproducts C, advantageously at the bottom of distillation column; b2) distilling said current Glb obtained in step b1) to form a current Glc comprising 2,3,3,3-tetrafluoropropene (1234yf), a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the top of the distillation column, and a stream Gld comprising a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the bottom of the distillation column.
    Preferably, the current Glc formed in step b2) may comprise 2,3,3,3-tetrafluoropropene (1234yf), 1,1,1,2,2-pentafluoropropane (245cb) and 1,3,3,3 -tetrafluoro-1-propene (1234ze). Preferably, the stream G1 1 formed in step b2) may comprise 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE), 2 Chloro-3,3,3-trifluoropropene (1233xf) and optionally El-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) . In particular, the content of 1,1,1,2,2-pentafluoropropane (245cb) is greater in the Gld current than in the Glc current. The Gld stream can contain 55%, 60%, 65%, 70%, 75%, 78% or 80% of the 1,1,1,2,2-pentafluoropropane (245cb) based on the total content of 1,1,1,2,2-pentafluoropropane (245cb). 1,2,2-pentafluoropropane (245cb) in the Gld and Glc stream.
    Stream Gld may be recycled in step a) of the present process. The stream Gld may be one of the one or more recycled streams in step a) (step c) of the present process.
    According to a preferred embodiment, the process comprises a step b3), subsequent to step b2), wherein the current Glc obtained in step b2) comprises 2,3,3,3-tetrafluoropropene (1234yf), 1 1,1,2,2-pentafluoropropane (245cb) and trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE); and said current Glc is distilled to form a Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and a Gif stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3 3,3-tetrafluoro-1-propene (1234zeE).
    The current Gif obtained in step b3) can be separated by extractive distillation.
    According to a particular embodiment, the current Gif obtained in step b3) is separated by extractive distillation according to the steps: b4) contacting said Gif stream obtained in step b3) with an organic extraction agent to form a current Glg, and b5) extractive distillation of the current Glg to form a flux Glh comprising 1,1,1,2,2-pentafluoropropane (245cb), advantageously at the top of the distillation column, and a composition Gli comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE) and said organic extraction agent, advantageously at the bottom of the distillation column.
    Preferably, the Gli stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) and said organic extractant is separated by distillation to form a stream G1 comprising said organic extractant and a Glk stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE). The current Glj comprising said organic extraction agent can be recycled in step b4). The Glk stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) can be either purified or destroyed by incineration.
    According to a preferred embodiment, said organic extraction agent is a solvent selected from the group consisting of hydrohalocarbon, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, thioalkyl, amide, heterocycle. Advantageously, said organic extraction agent is a solvent selected from the group consisting of alcohol, ketone. amine, ester and heterocycle. According to a preferred embodiment, said organic extraction agent has a boiling point between 10 and 150 ° C.
    Preferably, said extracting agent may have a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s P2) in which yi, s represents the coefficient of activity of 1,1,1,2,2-pentafluoropropane in said infinitely diluted organic extraction agent, PI represents the saturated vapor pressure of 1,1,1 , 2,2-pentafluoropropane, y2, s represents the activity coefficient of said trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) in said organic infinite dilution extractant, P2 represents the pressure saturated vapor of said trans-1,1,3,3-tetrafluoro-1-propene (1234zeE); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
    The saturation vapor pressure is considered for a temperature of 25 ° C.
    Preferably, said organic extraction agent may have a separation capacity C2, s greater than or equal to 0.20, said separation capacity being calculated by the formula C2, s = 1 / (y2, s) in which y2, s represents the coefficient of activity of said trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) in said organic infinite dilution extractant; advantageously, the C2, s separation capacity is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
    Preferably, said organic extraction agent may have a separation factor
    Si, 2 greater than or equal to 1.5 and a capacity of absorption C2, s greater than or equal to 0.6 and being selected from the group consisting of ethylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n-methylpropylamine, isobutanol, tetrahydrofuran, isopropylformate, diisopropylether, 2-ethoxy-2-methylpropane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 1-methoxy-2 methyl butane, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, di-n-propylether, 3-pentylamine, n- methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, opionitrile, 2-allyloxyethanol, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3, 3-dimethyl-2-butanone, 1,3-dioxane, piperidine, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, pyridine, 4-methyl-2- pentanone, 1,2-diaminoethane, butyronitrile, sec-butyl-tert-butylether, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-methylpyrazine, 2-ethoxy- l-propanol, 1-methylpiperazine, 1,3-propanediamine, di-n-butyleth er, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n, n-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol. Advantageously, said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.8 and / or an absorption capacity C2, s greater than or equal to 0.8; and being selected from the group consisting of ethylamine, isopropylamine, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, diethylamine, propanone, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, 1,2-dimethoxyethane, 3-methyl-2-butanamine, 3-pentylamine, n-methylbutylamine, 1-methoxy-2-propanamine, 2-methoxyethanamine, ethylpropionate, dioxane, 3-pentanone, 2-pentanone, 2-methoxy- propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, n-methyl-1,2-ethanediamine, 1,2-diaminoethane, butyronitrile, methoxy2-propanol, 1,2-propanediamine, 1- (dimethylamino) -2-propanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 2-methoxyl-propanol, 1, ethoxy-2 propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 2-ethoxy-1-propano 1,1-methylpiperazine, 1,3-propanediamine, valeronitrile, 2-heptanamine, n, n-diethylethylenediamine, 4-methyl-2-hexanone, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl -1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol. Preferably, said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.9 and / or an absorption capacity C2, s greater than or equal to 0.9 and be selected from the group consisting of ethylamine, isopropylamine, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, diethylamine, propanone, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, 1,2-dimethoxyethane, 3 -methyl-2-butanamine, 3-pentylamine, n-methylbutylamine, 1-methoxy-2-propanamine, 2-methoxyethanamine, ethylpropionate, dioxane, 3-pentanone, 2-pentanone, 2-methoxy-1-propanamine, n-pentylamine, 3 , 3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, n-methyl-1,2-ethanediamine, 1,2-diaminoethane, 1,2-propanediamine, 1- (dimethylamino) -2 propanol, 2-ethylbutylamine, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 1-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, 2- (dimethylamino) -ethano cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 2-ethoxy-1-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, n, n-diethylethylenediamine, 1-methoxy-2-acetoxypropane, 4- methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 1-propoxy-2-propanol. More particularly, said organic extractant is selected from the group consisting of ethylamine, isopropylamine, n-propylamine, diethylamine, propanone, tetrahydrofuran, ethylacetate, butanone, 3-pentylamine, 2-methoxyethanamine, dioxane, 3-pentanone, 2- pentanone, n-pentylamine, 1,3-dioxane, 1,2-diaminoethane, 1,2-propanediamine, 2-methoxyethanol, n-butylacetate, 1-ethoxy-2-propanol.
    Said Glh stream comprising 1,1,1,2,2-pentafluoropropane (245cb) can be recycled in step a) of the present process. Said Glh stream comprising 1,1,1,2,2-pentafluoropropane (245cb) may be one of the one or more recycled streams in step a) of the present process (step c)).
    As explained above, the Gli stream comprising trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) and said organic extractant is distilled to separate the organic extraction agent from the trans-l. , 3,3,3-tetrafluoro-1-propene (1234zeE), advantageously, said organic extraction agent thus separated is recycled to step b4). Trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) can be incinerated or purified for later use or for sale.
    If the gas stream G1 optionally comprises after distillation of the HF, it can be contained in said current Glb, then Glc. Thus, prior to step b3), unreacted HF contained in the Glc stream can be removed from said Glc stream. The removal of the HF can be carried out by a series of steps of absorption thereof in an aqueous medium. The current Glc can then be neutralized in the presence of a base, for example an alkaline or alkaline-earth hydroxide, and then dried, for example on a molecular sieve, to remove any traces of water. Optionally or not, if the current Glc comprises impurities having a boiling point lower than that of 2,3,3,3-tetrafluoro-1-propene, they can be removed by distillation. Said impurities having a boiling point lower than that of 2,3,3,3-tetrafluoro-1-propene may be trifluoromethane (F23), monofluoromethane (F41), difluoromethane (F32), pentafluoroethane (F125), 1,1 1-trifluoroethane (F143a), trifluoropropyl or 1-chloro-pentafluoroethane (F115); and these can be recovered at the top of the distillation column. The stream recovered at the bottom of the distillation column can then be used as described above for the Glc stream in step b) and the subsequent steps.
    The Gle current can be purified, as previously by extractive distillation, to remove trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) possibly present. In this case, said organic extractant is a solvent selected from the group consisting of hydrocarbon, hydrohalocarbon, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, thioalkyl, amide and heterocycle; or said organic extractant is difluorodiethylsilane, triethylfluorosilane or perfluorobutanoic acid; preferably from the group consisting of amine, ether, ketone, ester, alcohol, aldehyde, heterocycle. The boiling point of said organic extractant may be from 10 to 150 ° C. Said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2 where yi, s represents the activity coefficient of 2,3,3,3-tetrafluoro-1-propene in said infinitely diluted organic extractant, PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene , 3-tetrafluoro-1-propene, y 2, s represents the activity coefficient of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), in said organic extraction agent with infinite dilution P2 represents the saturated vapor pressure of said at least one of trans-1,3,3,3-tetrafluoro-1-propene compounds (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0. Said organic extraction agent can have an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (y2, s) in which y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E) in said organic infinite dilution extractant; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0. Advantageously, said organic extraction agent can be ethylamine, isopropylamine, diethylether, ethoxy-ethene, dimethoxymethane, n-propylamine, methyl-t-butylether, diethylamine, propanone, methylacetate, isobutanal, tetrahydrofuran, isopropylformate, diisopropylether, 2-ethoxy- 2-methylpropane, ethylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, trimethoxymethane, n-pentylamine, 1, 3-dioxane, 3,3-dimethyl-2-butanone, sec-butylacetate, 4-methyl-2-pentanone, 1,2-diaminoethane, 1-methoxy-2-propanol, diethylcarbonate, n-butylacetate, 1-ethoxy-2 propanol, hexanal; advantageously, said organic extraction agent is chosen from the group consisting of ethylamine, isopropylamine, diethyl ether, dimethoxymethane, n-propylamine, diethylamine, diisopropylether, 2-ethoxy-2-methylpropane, butanone, diethoxymethane, isopropylacetate, 3- pentylamine, 2-methoxyethanamine, tert-butylacetate, dioxane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, n-butylacetate, 1-ethoxy-2 propanol, hexanal; preferably said organic extractant is selected from the group consisting of ethylamine, isopropylamine, diethylether, dimethoxymethane, n-propylamine, diethylamine, diisopropylether, 2-ethoxy-2-methylpropane, diethoxymethane, isopropylacetate, 3-pentylamine, 2 methoxyethanamine, tert-butylacetate, dioxane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, n-butylacetate, 1-ethoxy-2-propanol, hexanal .
    Alternatively, as mentioned above, the Glc stream can be distilled by extractive distillation to form a Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb) ; and a Gif stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE). According to a preferred embodiment, said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * Pl) / (y2, s * P2) wherein yi, s represents the activity coefficient of 2,3,3,3-tetrafluoro-1-propene in said infinitely diluted organic extraction agent, PI represents the vapor pressure 23,3,3,3-tetrafluoro-1-propene, y2, s represents the activity coefficient of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) in said infinitely diluted organic extraction, P2 represents the saturated vapor pressure of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8. In this embodiment, said organic extractant may also have a separation factor
    If, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (Yi, s * P1) / (Y2, s * P2) in which y1 | S represents the activity coefficient 1,1,1,2,2-pentafluoropropane (245cb) in said infinitely diluted organic extraction agent, PI represents the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb), y2 , s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) in said infinitely-diluted organic extractant, P2 represents the saturated vapor pressure of the trans- 1,1,3,3-tetrafluoro-1-propene (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0. In this preferred embodiment, said organic extraction agent may have an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (y 2, s) wherein y2, s represents the activity coefficient of said at least one of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) compounds in said diluted organic extractant infinite, preferably y2, s represents the activity coefficient of said at least one of the compounds consisting of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), in said organic extractant at infinite dilution; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0. Thus, in this preferred embodiment, said organic extractant may be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether , diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane , 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3 -dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, 4-methyl-2-penta none, 1,2-diaminoethane, butyronitrile, 1-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 1,1-diethoxypropane, 2- ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal; advantageously, ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal; preferably, ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal.
    According to another preferred embodiment, said liquid stream L1 comprises all or part of intermediate products B and all or part of secondary products C; and all or part of this stream L1 is heated at low temperature, advantageously between -50 ° C and 20 ° C, to form a first phase Lia comprising a portion of unreacted HF and a second phase Llb comprising said intermediate products B and said secondary products C. Advantageously, said low temperature is between -50 ° C and 15 ° C, preferably between -40 ° C and 10 ° C, in particular between -30 ° C and 0 ° C. This step can be performed continuously or discontinuously.
    Said first phase Lia can be recycled in step a).
    Optionally or not, said current G11 formed in step b2) can be mixed with the liquid stream L1 before all or part of the latter is heated to a low temperature.
    All or part of 1,1,1,2,2-pentafluoropropane (245cb) can also be contained in said liquid stream L1 and then in said second phase Llb.
    All or part of the 1,3,3,3-tetrafluoro-1-propene (1234ze) can also be contained in said liquid stream L1 and then in said second phase Llb.
    All or part of 2-chloro-3,3,3-trifluoropropene (1233xf) may also be contained in said liquid stream L1 and then in said second phase Llb.
    All or part of the E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) may also be contained in said liquid stream L1 and then in said second phase Llb.
    All or part of the 1,1,1,3,3-pentafluoropropane (245fa) may also be contained in said liquid stream L1 and then in said second phase Llb.
    Preferably, said second L1b phase may comprise 1,1,1,3,3-pentafluoropropane (245fa), E1-chloro-3,3,3-trifluoro-1-propene (1233zdE), 2-chloro-3,3 , 3-trifluoropropene (1233xf), 1,3,3,3-tetrafluoro-1-propene (1234ze) and 1,1,1,2,2-pentafluoropropane (245cb).
    According to a preferred embodiment, said second phase Llb is distilled to recover a Lie stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and 1,3,3,3-tetrafluoro-1-propene (1234ze) , advantageously at the top of the distillation column, and a stream Lld comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), 1-chloro-3,3,3-trifluoro-1-propene (1233zdE ) and 1,1,1,3,3-pentafluoropropane (245fa); advantageously at the bottom of the distillation column. Said Lie current can be recycled in step a). Said current Lie may therefore be one of the said one or more recycled streams in step a) during step c) of the present process. Optionally, said Lie stream may be purified to separate 1,1,1,2,2-pentafluoropropane (245cb) and 1,3,3,3-tetrafluoro-1-propene (1234ze). This can be done by extractive distillation as explained above in connection with the separation of the Gif stream.
    According to a preferred embodiment, said Lld stream can be separated to form a stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and a stream comprising E1-chloro-3,3,3- trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa). The separation of said Lld current can be carried out by extractive distillation.
    Preferably, said Lld may be an azeotropic or azeotropic composition comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa).
    Preferably, said separation can be carried out by extractive distillation. Said extractive distillation of said stream Lld comprises the steps of: - contacting said stream Lld with an organic extraction agent to form a composition Lie, and - extractive distillation of the composition Lie to form a stream Llf comprising 2-chloro-3 , 3,3-trifluoro-1-propene (1233xf), advantageously at the top of the distillation column, and a stream Llg comprising E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1, 1,3,3-pentafluoropropane (245fa) and said organic extraction agent, advantageously at the bottom of the distillation column.
    Preferably, the stream L1 is then separated by distillation to form a stream L1 comprising said organic extraction agent and a stream L1 comprising E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1.1 1,3,3-pentafluoropropane (245fa). The current Llh can be recycled to be contacted with a current Lld to form a composition Lie. Lli stream comprising E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) can be either purified or destroyed by incineration.
    According to a preferred embodiment, said organic extraction agent brought into contact with the current Lld is a solvent selected from the group consisting of hydrocarbon, hydrohalocarbon, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, sulfoxide sulfate, thioalkyl, amide, heterocycle and phosphate or the organic extractant is perfluorobutanoic acid. According to a preferred embodiment, said organic extraction agent has a boiling point between 50 and 200 ° C. According to a preferred embodiment, said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * Pl) / (y2, s * P2) wherein yi, s represents the activity coefficient of 2-chloro-3,3,3-trifluoropropene in said infinitely diluted organic extraction agent, PI represents the saturation vapor pressure of 2 -chloro-3,3,3-trifluoropropene, y2, s represents the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic infinite dilution extractant, P2 represents the pressure saturated vapor of 1,1,1,3,3-pentafluoropropane (245fa); advantageously, the separation factor Si, 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to 2.0; and said organic extractant has an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (y2, s) in which y2, s represents the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic infinite dilution extractant; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
    Thus, according to a particular embodiment, said organic extraction agent may be chosen from the group consisting of ethanedial, propanone, methylacetate, methylglyoxal, ethylacetate, butanone, propionitrile, dioxane, trimethoxymethane, 1,3-dioxane, 1,3 5-trioxane, 1,2-diaminoethane, 1-methoxy-2-propanol, diethylcarbonate, 2-methoxyl-propanol, 1-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxy-1-butanol, diacetone alcohol, methylacetoacetate, η, η-dimethylpropanamide, dimethylmalonate, diethylsulfoxide, 2- (2-methoxyethoxy) ethanol, trimethylphosphate, diethylmalonate; preferably said organic extractant may be selected from the group consisting of propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1,2-diaminoethane, methoxy-2-propanol. Preferably, this particular embodiment can effectively separate 2-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluoropropane (245fa).
    According to a particular embodiment, said organic extraction agent brought into contact with the current Lld may have a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2) wherein yi, s represents the activity coefficient of 2-chloro-3,3,3-trifluoropropene in said organic end-dilution extractant, PI represents the saturating vapor pressure of 2-chloro-3,3,3-trifluoropropene, y2, s represents the activity coefficient of E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) in said agent of organic extraction at infinite dilution, P2 represents the saturated vapor pressure of 1-chloro-3,3,3-trifluoro-1-propene (1233zdE); advantageously, the separation factor Si, 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to 2.0; and said organic extractant may have an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (y2, s) in which y2, s represents the activity coefficient of E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) in said organic infinite dilution extractant; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.8, in particular greater than or equal to 1.0.
    Thus, in a particular embodiment, said organic extraction agent may be chosen from the group consisting of isopropylmethylamine, methyl-t-butylether, diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1-butylamine. ethylacetate, butanone, n-propylformate, dimethoxypropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-methoxy-2-propanamine, 2- methoxyethanamine, tert-butylacetate, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2- butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2- propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 2-methoxyl-propanol, 1-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) -ethanol, cyclohexylamine, n- ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-ethoxy-1-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, n, n-diethylethylenediamine, 4-methyl-2-hexanone, 1,1,1- triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol, 2-heptanone , dimethylformamide, 2-isopropoxyethanol, 2-methylpiperazine, cyclohexanone, 1-heptanamine, 2-ethoxyethanolacetate, 1,4-butanediamine, 2,4-dimethylpyridine, 2-methoxy-3-methylpyrazine, 4-methoxy-4-methylpentan -2-one, 3-ethoxy-1-propanol, 3-methoxy-1-butanol, diglyme, 2- (diethylamino) -ethanol, 2,2-diethoxyethanamine, 2-methoxy-n- (2-methoxyethyl) ethanamine, 2- (ethylamino) ethanol, 3-octanone, diacetone alcohol, diethylaminopropylamin e, 2-ethylhexylamine, 1-butoxy-2-propanol, 2-butoxyethanol, 2-octanone, methylheptanoate, triethylenediamine, n, n-dimethylpropanamide, 2-propanol-1-methoxypropanoate, 1,5-pentanediamine, cycloheptanone, 3,4-dimethylpyridine, 1-octanamine, benzylmethylamine, 1,1,3,3-tetramethoxypropane, dihexylphthalate, diethylpropanolamine, 2-butoxyethanolacetate, diethylsulfoxide, 2- (2-methoxyethoxy) ethanol, 4-methylbenzenemethanamine, diethyleneglycolmonoethylether, 2-propylcyclohexanone trimethylphosphate, 2-methyl-2,4-pentanediol, methylbenzoate, diethylmalonate, 2-methoxypyrimidine; preferably said organic extractant is selected from the group consisting of diethylamine, propanone, methylacetate, tetrahydrofuran, ethylacetate, butanone, diethoxymethane, isopropylacetate, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, n-butylacetate, 1-ethoxy-2-propanol. Preferably, this particular embodiment can effectively separate 2-chloro-3,3,3-trifluoropropene and E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE).
    According to a preferred embodiment, to promote the simultaneous elimination of E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa); said organic extraction agent contacted with the Lld current may be selected from the group consisting of propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, 1-methoxy-2-propanol, diethyl carbonate , 2-methoxyl-propanol, 1-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxy-1-butanol, diacetone alcohol, n, n-dimethylpropanamide, diethylsulfoxide, 2- (2-methoxyethoxy) ethanol, trimethylphosphate, diethylmalonate. In particular, said organic extraction agent may be selected from the group consisting of propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, 1-methoxy-2-propanol, 3-methoxy 1-butanol, diacetone alcohol.
    According to a preferred embodiment, said current Llg comprising E1-chloro-3,3,3-trifluoro-1-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and said extractant organic can be distilled to separate on the one hand said organic extraction agent and on the other hand E1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3, 3-pentafluoropropane (245fa). Preferably, said organic extraction agent can be recycled.
    According to a preferred embodiment, the Llf stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf) is recycled to step a).
    If heavy impurities are present in said stream Lld, it can be distilled prior to its separation to eliminate them. The Lld current as described above can be recovered at the top of the distillation column, the heavy impurities being recovered at the bottom of the distillation column. The heavy impurities may contain, for example, 1,2-dichloro-3,3,3-trifluoropropene (1223xd), dimers or trimers derived from one of the compounds present in the composition or the current under consideration.
    More particularly, the starting composition may comprise 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, 1,1,3,3-tetrachloropropene, 1,3,3,3-tetrachloropropene, tetrachloropropene, 1,1,1,2,3-pentachloropropane, 1,1,1,3,3-pentachloropropane, 1,1,2,2,3-pentachloropropane, 1,2-dichloro-3,3,3 trifluoropropane, 2-chloro-2,3,3,3-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane, 1-chloro-1,3,3,3-tetrafluoropropane and 1,1,1,2,2-pentafluoropropane; , 1,3,3-pentafluoropropane, preferably 1,1,1,2,3-pentachloropropane, 1,1,2,3, tetrachloropropene, 1,1,1,2,2-pentafluoropropane and / or 2 chloro-3,3,3-trifluoro-1-propene; in particular 1,1,1,2,3-pentachloropropane (240db).
    The catalyst used in the present process for producing 2,3,3,3-tetrafluoropropene may for example be based on a metal comprising a transition metal oxide or a derivative or a halide or an oxyhalide of such a metal. . For example, FeCU, chromium oxyfluoride, chromium oxides (possibly subjected to fluorination treatments), chromium fluorides and mixtures thereof may be mentioned. Other possible catalysts are carbon-supported catalysts, antimony catalysts, aluminum catalysts (eg AlF 3 and Al 2 O 3, alumina oxyfluoride and alumina fluoride).
    It is generally possible to use a chromium oxyfluoride, a fluoride or an aluminum oxyfluoride, or a supported or non-supported catalyst containing a metal such as Cr, Ni, Fe, Zn, Ti, V, Zr, Mo, Ge or Sn. Pb, Mg, Sb.
    Reference can be made in this regard to document WO 2007/079431 (in p.7,1.1-5 and 28-32), to document EP 939071 (paragraph [0022]), to document WO 2008/054781 (in p.9). 1.22-p.101.34), and WO 2008/040969 (claim 1), to which reference is expressly made.
    The catalyst is more preferably based on chromium and it is more particularly a mixed catalyst comprising chromium.
    According to one embodiment, a mixed catalyst comprising chromium and nickel is used. The molar ratio Cr / Ni (based on the metal element) is generally 0.5 to 5, for example 0.7 to 2, for example about 1. The catalyst may contain from 0.5 to 20% by weight of nickel.
    The metal may be present in metallic form or in the form of a derivative, for example an oxide, halide or oxyhalide. These derivatives are preferably obtained by activation of the catalytic metal.
    The support is preferably made of aluminum, for example alumina, activated alumina or aluminum derivatives, such as aluminum halides and aluminum oxyhalides, for example described in US Pat. US 4,902,838, or obtained by the activation method described above.
    The catalyst may comprise chromium and nickel in an activated or non-activated form, on a support which has been subjected to activation or not.
    Reference can be made to WO 2009/118628 (especially at p.4, l.30-p.7 1.16), which is expressly referred to herein.
    Another preferred embodiment is based on a chromium-containing mixed catalyst and at least one element selected from Mg and Zn. The atomic ratio of Mg or Zn / Cr is preferably from 0.01 to 5.
    Prior to use, the catalyst is preferably activated with air, oxygen or chlorine and / or with HF.
    For example, the catalyst is preferably subjected to activation with air or oxygen and HF at a temperature of 100 to 500 ° C, preferably 250 to 500 ° C and more preferably 300 to 400 ° C. ° C. The activation time is preferably from 1 to 200 hours and more particularly from 1 to 50 hours.
    This activation may be followed by a final fluorination activation step in the presence of an oxidizing agent, HF and organic compounds.
    The molar ratio of HF / organic compounds is preferably from 2 to 40 and the molar ratio of oxidation agent / organic compounds is preferably from 0.04 to 25. The temperature of the final activation is preferably from 300 to 400 ° C. C and its duration preferably from 6 to 100 h.
    The gas phase fluorination reaction can be carried out: with a HF / compound of formula (I) and / or (II) molar ratio of from 3: 1 to 150: 1, preferably from 4: 1 to 125: 1 and more preferably, from 5: 1 to 100: 1; with a contact time of 3 to 100 seconds, preferably 4 to 75 seconds and more particularly 5 to 50 seconds (volume of catalyst divided by the total incoming flow, adjusted to the temperature and to the operating pressure); at a pressure ranging from atmospheric pressure to 20 bar, preferably from 2 to 18 bar and more particularly from 3 to 15 bar; at a temperature (temperature of the catalyst bed) of 200 to 450 ° C., preferably of 250 to 400 ° C., and more particularly of 280 to 380 ° C.
    The duration of the reaction step is typically from 10 to 8000 hours, preferably from 50 to 5000 hours and more preferably from 70 to 1000 hours.
    An oxidizing agent, preferably oxygen, may optionally be added during the fluorination reaction. The oxygen / organic compounds molar ratio may be from 0.005 to 2, preferably from 0.01 to 1.5. The oxygen can be introduced pure or in the form of air or oxygen / nitrogen mixture. Oxygen can also be replaced by chlorine.
    Fig. 1 schematically illustrates a device implementing a process for producing 2,3,3,3-tetrafluoropropene according to a particular embodiment of the present invention. The hydrofluoric acid 1 is brought into contact with 1,1,1,2,3-pentachloropropane (240db) 2 in one or more reactors 3. The resulting mixture comprising 2,3,3,3-tetrafluoro-1 propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234zeE), 2-chloro-3,3,3-trifluoropropene (1233xf), El-chloro - 3.3.3- trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) is recovered at the outlet of the reactor and conveyed to a distillation column 5 via line 4. The mixture can also include HCl, unreacted HF and heavy impurities or impurities having a boiling point lower than that of 2,3,3,3-tetrafluoro-1-propene. All or part of the stream obtained at the bottom of the distillation column is conveyed to purification device 13 via line 7. From this purification device 13 can be extracted HF, 2-chloro-3,3,3-trifluoropropene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb), and optionally trans-1,3,3,3-tetrafluoro-1-propene (1234zeE), which are recycled to reactor 3 via line 15. El-chloro-3 3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) may also be removed from the device 13 to be discharged at 14 to an incinerator or a purification device. A stream is also recovered at the top of the distillation column 5 and conveyed to a purification device 7 via the conduit 6. From the purification device 7, a stream comprising 2,3,3,3-tetrafluoro-1-propene is recovered at 11 via line 8. A flow comprising 1,1,1,2,2-pentafluoropropane (245cb), and optionally trans-1,3,3,3-tetrafluoro-1-propene (1234zeE), is also obtained and recycled to the reactor Finally, a stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) can be recovered at 12 via line 9.
    Fig. 2 illustrates schematically according to a particular embodiment of the present invention a purification device 13. A stream 21 comprising in particular HF, trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE), 1,1,1 2,2-pentafluoropropane (245cb), 2-chloro-3,3,3-trifluoropropene (1233xf), 1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3, 3-pentafluoropropane (245fa) is sent to the decanter 22 having a temperature of -25 ° C. The HF is extracted and recovered at 23 for recycling to the reactor 3. The other constituents are conveyed to the distillation column 25 via line 24. Trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) and 1,1,1,2,2-pentafluoropropane (245cb) are removed at the top of the distillation column and recovered at Tl via line 26. These can be recovered for recycling to reactor 3. 2-chloro -3,3,3-trifluoropropene (1233xf), 1-chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) are fed to the column distillation device 29 via line 28 to extract any heavy impurities present at the bottom of the distillation column and convey them to an incinerator 32 via line 31. 2-chloro-3,3,3-trifluoropropene (1233xf), El- chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1.1.1.3.3- pentafluoropropane (245fa) recovered at the top of the distillation column 29 are conveyed to Purification device 33 via conduit 30. From this purification device 33, 2-chloro-3,3,3-trifluoropropene (1233xf) can be extracted at 36 via line 34. Purification device 33 can be a extractive distillation. E-1-Chloro-3,3,3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) can be recovered at 37 via line 35 to be incinerated or purified.
    Fig. 3 schematically illustrates, according to a particular embodiment of the present invention, a purification device 7. A storage tank 41 comprises 2,3,3,3-tetrafluoro-1-propene, trans-1,3,3,3-tetrafluoro 1-propene (1234zeE), 1,1,1,2,2-pentafluoropropane (245cb) and impurities having a boiling point lower than that of 2,3,3,3-tetrafluoro-1-propene. This mixture is conveyed to distillation column 43 via line 42. The impurities having a boiling point lower than that of 2,3,3,3-tetrafluoro-1-propene are discharged at 45 via line 44. Other constituents of the mixture are conveyed to distillation column 47 via line 46. A stream comprising 2,3,3,3-tetrafluoro-1-propene is recovered at the top of the distillation column and discharged at 48 to tanks of storage or an additional purification device 55, for example an extractive distillation device. The trans-1,3,3,3-tetrafluoro-1-propene (1234zeE), 1,1,1,2,2-pentafluoropropane (245cb) are recovered at the bottom of the distillation column to be conveyed to a purification device. 50 via line 49. A stream comprising 1,1,1,2,2-pentafluoropropane (245cb) separated from trans-1,1,3,3-tetrafluoro-1-propene (1234zeE) is recovered at 53 via the conduit. 52. The stream comprising 1,1,1,2,2-pentafluoropropane (245cb) recovered at 53 can be recycled to the reactor 3. A stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) is recovered in 54 via line 51 to be incinerated or purified. The purification device 50 may be extractive distillation.
    权利要求:
    Claims (14)
    [1" id="c-fr-0001]
    claims
    A process for the production and purification of 2,3,3,3-tetrafluoropropene (1234yf) carried out starting from a starting composition comprising at least one compound of formula (I) CX (Y) 2-CX ( Y) m-CHmXY wherein X and Y independently represent a hydrogen, fluorine or chlorine atom and m = 0 or 1; and / or fluorinating in the presence of a catalyst of a compound of the formula (CXnY3-n) CHpXi-pCHmX2-m (H) wherein X is independently of each other Cl, F, I or Br; Y is independently of each other H, Cl, F, I or Br; n is 1, 2 or 3; and m is 0.1 or 2; and p is 0 or 1; said process comprising the steps of: a) contacting, in the presence of a catalyst, the starting composition with HF to produce a composition A comprising 2,3,3,3-tetrafluoropropene (1234yf), intermediate products B consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,2,2-pentafluoropropane (245cb), and by-products C consisting of 1-chloro-3,3,3-trifluoro 1-propene (1233zdE), trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) and 1,1,1,3,3-pentafluoropropane (245fa); b) recovering said composition A and purifying it to form and recover a first stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb); c) recycling in step a) said one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and / or 1,1,1,2,2-pentafluoropropane (245cb), characterized in that the content of at least one of the secondary products C in said one or more recycled streams in step a) is less than this in said composition A.
    [2" id="c-fr-0002]
    2. Method according to the preceding claim characterized in that: the composition A also comprises HCl, a part of unreacted HF; and purifying said composition A carried out in step b) comprising the distillation of said composition A to recover at the top of the distillation column a gaseous stream G1 comprising HCl and 2,3,3,3-tetrafluoropropene (1234yf); and at the bottom of the distillation column a liquid stream L1 comprising said part of unreacted HF; all or part of the intermediate products B and all or part of the secondary products C being contained in said gas stream G1 and / or in said liquid stream L1.
    [3" id="c-fr-0003]
    3. Process according to any one of the preceding claims, characterized in that said gaseous stream G1 comprises part of the intermediate products B and a part of the by-products C, and said gaseous stream G1 is purified by the following steps: b1) distillation of the G1 gas stream for recovering a Gla stream comprising HCl, advantageously at the top of the distillation column, and a Glb stream comprising 2,3,3,3-tetrafluoropropene (1234yf), said part of the intermediate products B and said part of the secondary products C, advantageously at the bottom of the distillation column; b2) distilling said current Glb obtained in step b1) to form a current Glc comprising 2,3,3,3-tetrafluoropropene (1234yf), a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the top of the distillation column, and a stream Gld comprising a portion of said portion of the intermediate products B and a portion of said portion of the by-products C, advantageously at the bottom of the distillation column.
    [4" id="c-fr-0004]
    4. Method according to any one of claims 3 characterized in that the method comprises a step b3), subsequent to step b2), wherein the current Glc obtained in step b2) comprises 2,3,3, 3-tetrafluoropropene (1234yf), 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,33,3-tetrafluoro-1-propene (1234zeE); and said current Glc is distilled to form a Gle stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and a Gif stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3 3,3-tetrafluoro-1-propene (1234zeE).
    [5" id="c-fr-0005]
    5. Method according to the preceding claim characterized in that the current Gif obtained in step b3) is separated by extractive distillation.
    [6" id="c-fr-0006]
    6. Method according to the preceding claim characterized in that the Gif stream obtained in step b3) is separated by extractive distillation according to the steps: b4) bringing said Gif stream obtained in step b3) into contact with an agent. organic extraction to form a current Glg, and b5) extractive distillation of the current Glg to form a flux Glh comprising 1,1,1,2,2-pentafluoropropane (245cb), advantageously at the top of the distillation column, and a Gli stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234zeE) and said organic extracting agent, advantageously at the bottom of the distillation column.
    [7" id="c-fr-0007]
    7. Method according to the preceding claim characterized in that the Glh flux comprising 1,1,1,2,2-pentafluoropropane (245cb), preferably free of trans-1,3,3,3-tetrafluoro-1-propene ( 1234zeE), is recycled in step a).
    [8" id="c-fr-0008]
    8. Method according to any one of claims 2 to 7 characterized in that said liquid stream L1 comprises all or part of the intermediate products B and all or part of the secondary products C, and all or part of the liquid stream L1 is brought to low temperature, advantageously between -50 ° C and 20 ° C, to form a first phase Lia comprising a portion of unreacted HF and a second phase Llb comprising said intermediate products B and said secondary products C; optionally or not, said current G11 formed in step b2) is mixed with the liquid stream L1 before the latter is heated to a low temperature.
    [9" id="c-fr-0009]
    9. Method according to the preceding claim characterized in that said first phase Lia is recycled in step a).
    [10" id="c-fr-0010]
    10. The method of claim 8 or 9 characterized in that said second phase Llb is distilled to recover a Lie stream comprising 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3- tetrafluoro-1-propene (1234zeE), advantageously at the top of the distillation column, and a stream Lld comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), El-chloro-3,3,3 -trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa); advantageously at the bottom of the distillation column, advantageously said Lie stream is recycled in step a).
    [11" id="c-fr-0011]
    11. Method according to the preceding claim characterized in that said Lld current is separated to form a stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and a stream comprising El-chloro-3,3 3-trifluoro-1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa).
    [12" id="c-fr-0012]
    12. Method according to the preceding claim characterized in that the separation of said Lld current is carried out by extractive distillation.
    [13" id="c-fr-0013]
    13. Method according to the preceding claim characterized in that the extractive distillation of said Lld stream comprises the steps of: - contacting said Lld current with an organic extraction agent to form a composition Lie, and - extractive distillation of the composition Lie to form a Llf stream comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), advantageously at the top of the distillation column, and an L1g stream comprising E1-chloro-3,3,3-trifluoro- 1-propene (1233zdE) and 1,1,1,3,3-pentafluoropropane (245fa) and said organic extraction agent, advantageously at the bottom of the distillation column.
    [14" id="c-fr-0014]
    14. Method according to the preceding claim characterized in that the flow Llf comprising 2-chloro-3,3,3-trifluoro-1-propene (1233xf), preferably free of E-chloro-3,3,3-trifluorocarbon. 1-propene (1233zdE) and / or 1,1,1,3,3-pentafluoropropane (245fa) is recycled in step a).
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    同族专利:
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    CN108368013A|2018-08-03|
    US20180370879A1|2018-12-27|
    MX2018007594A|2018-09-21|
    US10407369B2|2019-09-10|
    EP3394019A1|2018-10-31|
    JP2019501166A|2019-01-17|
    ES2777607T3|2020-08-05|
    WO2017108523A1|2017-06-29|
    JP6964589B2|2021-11-10|
    EP3394019B1|2020-01-29|
    US10730813B2|2020-08-04|
    US20190345083A1|2019-11-14|
    FR3046164B1|2021-01-08|
    PL3394019T3|2020-06-29|
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    法律状态:
    2016-11-11| PLFP| Fee payment|Year of fee payment: 2 |
    2017-06-30| PLSC| Publication of the preliminary search report|Effective date: 20170630 |
    2017-11-13| PLFP| Fee payment|Year of fee payment: 3 |
    2019-11-14| PLFP| Fee payment|Year of fee payment: 5 |
    2020-11-12| PLFP| Fee payment|Year of fee payment: 6 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1563168A|FR3046164B1|2015-12-23|2015-12-23|PROCESS FOR THE PRODUCTION AND PURIFICATION OF 2,3,3,3-TETRAFLUOROPROPENE.|FR1563168A| FR3046164B1|2015-12-23|2015-12-23|PROCESS FOR THE PRODUCTION AND PURIFICATION OF 2,3,3,3-TETRAFLUOROPROPENE.|
    PL16809821T| PL3394019T3|2015-12-23|2016-12-14|Method for producing and purifying 2,3,3,3-tetrafluoropropene|
    US16/063,302| US10407369B2|2015-12-23|2016-12-14|Method for producing and purifying 2,3,3,3-tetrafluoropropene|
    JP2018532114A| JP6964589B2|2015-12-23|2016-12-14|Methods for producing and purifying 2,3,3,3-tetrafluoropropene|
    MX2018007594A| MX2018007594A|2015-12-23|2016-12-14|Method for producing and purifying 2,3,3,3-tetrafluoropropene.|
    CN201680071474.2A| CN108368013A|2015-12-23|2016-12-14|The method of production and purifying 2,3,3,3- tetrafluoropropenes|
    ES16809821T| ES2777607T3|2015-12-23|2016-12-14|Procedure for the production and purification of 2,3,3,3-tetrafluoropropene|
    PCT/EP2016/080949| WO2017108523A1|2015-12-23|2016-12-14|Method for producing and purifying 2,3,3,3-tetrafluoropropene|
    EP16809821.8A| EP3394019B1|2015-12-23|2016-12-14|Method for producing and purifying 2,3,3,3-tetrafluoropropene|
    US16/521,031| US10730813B2|2015-12-23|2019-07-24|Method for producing and purifying 2,3,3,3-tetrafluoropropene|
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