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    • 专利摘要:
    The invention relates to an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 2,3,3-tri-trifluoro-1-chloropropene and one or more (hydro) halocarbon compounds having 1 to 3 carbon atoms. The (hydro) halocarbon compounds are preferably chosen from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes.
    公开号:FR3015478A1
    申请号:FR1362982
    申请日:2013-12-19
    公开日:2015-06-26
    发明作者:Dominique Deur-Bert；Anne Pigamo；Philippe Bonnet
    申请人:Arkema France SA；
    IPC主号:
    专利说明:

    [0001] FIELD OF THE INVENTION The present invention relates to azeotropic or quasi-azeotropic compositions based on hydrogen fluoride and on Z-3,3-azo-proprolytic compositions. 3-trifluoro-1-chloropropene.
    [0002] BACKGROUND 3,3,3-trifluoro-1-chloropropene or 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) exists as two isomers: the cis isomer, namely Z -3,3,3-trifluoro-1-chloropropene (HCF0-1233zdZ), and the trans isomer, namely E-3,3,3-trifluoro-1-chloropropene (HCFO-1233zdE). They have different boiling points, respectively 18.5 ° C for the trans compound and 39.5 ° C for the cis compound. Fluids based on E-3,3,3-trifluoro-1-chloropropene (HCFO-1233zdE) have found many applications in various industrial fields, including heat transfer fluids, propellants, foaming agents, agents blowing agents, gaseous dielectrics, polymerization media or monomers, support fluids, abrasive agents, drying agents and fluids for power generation units. The production of HCFO-1233zdE is accompanied by a multitude of by-products, with a boiling point close to HCFO-1233zdE. This leads to quite complex and expensive purification steps. The difficulties encountered during the purification of HCFO-1233zdE generally imply a consequent loss of the desired product. In addition, by-products can form azeotropic compositions with HCFO-1233zdE, making separation by simple distillation very difficult or impossible. US 6,013,846 discloses an azeotropic composition of HCFO-1233zd and hydrogen fluoride (HF). The document does not specify the isomeric form of HCFO-1233zd.
    [0003] US 6,328,907 discloses a azeotropic composition of 1,1,1,3,3-pentafluoropropane (HFC-245fa) and HF. US Pat. No. 8,378,158 describes a quasi-azeotropic composition of HCFO-1233zdZ and HF.
    [0004] US Pat. No. 7,423,188 describes an azeotropic composition of E-1,3,3,3-tetrafluoropropene (HFO-1234zeE) and HF. WO 2008/002500 discloses an azeotropic composition of Z-1,3,3,3-tetrafluoropropene (HFO-1234zeZ) and HF. US Pat. No. 7,183,448 describes an azeotropic composition of HFC-245fa and of HCFO-1233zd. It is stated in the document that the azeotrope is obtained with the trans isomer of HCFO-1233zd. US 8,075,797 discloses a near-azeotropic composition of HF, HFC-245fa and HCFO-1233zd. It is stated in the document that the quasi-azeotrope is obtained with the trans isomer of HCFO-1233zd.
    [0005] There is still a need to provide other azeotropic compositions including azeotropic compositions based compounds likely to be involved in the manufacture of HCFO-1233zdE. However, in general, the azeotropes are difficult to predict.
    [0006] SUMMARY OF THE INVENTION The invention primarily relates to an azeotropic or azeotropic composition comprising hydrogen fluoride, Z-3,3,3-trifluoro-chloropropene and one or more (hydro) halocarbon compounds having 1 at 3 carbon atoms.
    [0007] According to one embodiment, the (hydro) halocarbon compound (s) comprise 3 carbon atoms, and are preferably chosen from propanes and propenes partially or totally substituted with halogens. According to one embodiment, the (hydro) halocarbon compounds are chosen from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, trichlorofluorocarbons, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes. .
    [0008] According to one embodiment, the composition of the invention comprises hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3,3,3-trifluoro-1-chloropropene and a or several other (hydro) halocarbon compounds having 1 to 3 carbon atoms.
    [0009] According to one embodiment, the composition of the invention comprises hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-1,3,3,3-tetrafluoropropene and one or more other (hydro) halocarbon compounds having 1 to 3 carbon atoms.
    [0010] According to one embodiment, the composition of the invention comprises hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene and one or more other (hydro) halocarbon compounds having 1 to 3 carbon atoms. According to one embodiment, the composition of the invention comprises hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, 1,1,1,3,3-pentafluoropropane and one or more other (hydro) halocarbon compounds having 1 to 3 carbon atoms. According to one embodiment, the composition of the invention is a ternary mixture, and preferably is a mixture of hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene and E-3,3 , 3-trifluoro-1-chloropropene. According to one embodiment, the composition of the invention is a quaternary mixture, and preferably is a mixture of: hydrogen fluoride, 3,3,3-trifluoro-1-chloropropene, E-3 3,3-trifluoro-1-chloropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane. According to one embodiment, the composition of the invention is a five-year mixture, and preferably is a mixture of: - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3 3,3-trifluoro-1-chloropropene, 1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3,3,3-trifluoro-1-chloropropene, E 1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane. According to one embodiment, the composition of the invention is a senile mixture, and preferably is a mixture of: - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3 , 3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane.
    [0011] According to one embodiment, the composition of the invention is heteroazeotropic or quasi-heteroazeotropic. According to one embodiment, the composition of the invention comprises from 1 to 85% by weight, preferably from 1 to 80% by weight, more preferably from 5 to 80% by weight and most preferably from 5-75% by weight of hydrogen fluoride; and / or from 15 to 99% by weight, preferably from 20 to 99% by weight, more preferably from 20 to 95% by weight and most preferably from 25 to 95% by weight of compounds (hydro ) halocarbons having 1 to 3 carbon atoms.
    [0012] According to one embodiment, the composition of the invention has a boiling point of 0 to 40 ° C for a pressure of 0.5 to 9 bar absolute. The invention also relates to a process for producing a main (hydro) halocarbon compound, comprising: - forming a mixture of compounds comprising hydrogen fluoride, Z-3,3,3-trifluoro-1- chloropropene and one or more other (hydro) halocarbon compounds; the distillation of this mixture, making it possible to collect on the one hand an azeotropic composition of the invention, and on the other hand at least one of the compounds of the mixture.
    [0013] According to one embodiment, the distillation makes it possible to collect on the one hand an azeotropic composition of the invention, and on the other hand hydrogen fluoride; or on the one hand an azeotropic composition of the invention, and on the other hand E-3,3,3-trifluoro-1-chloropropene. According to one embodiment, the process of the invention is a process for producing 3,3,3-trifluoro-1-chloropropene, and preferably E-3,3,3-trifluoro-1-chloropropene. According to one embodiment, the mixture of compounds is obtained following a fluorination step, comprising the reaction of a chlorinated compound with hydrogen fluoride.
    [0014] According to one embodiment, the azeotropic composition collected is separated, preferably by decantation, into two immiscible liquid fractions, namely a fraction rich in hydrogen fluoride and a fraction that is poor in hydrogen fluoride, the fraction rich in hydrogen fluoride containing a higher proportion of hydrogen fluoride than the low hydrogen fluoride fraction; and the fraction rich in hydrogen fluoride being optionally recycled to the fluorination stage. The drunkard. In hydrogen is the object of a monomer of a further azeotropic puff of other, 1-3,3,3-trifluoro-i. In one embodiment, the compound chlorinated with hydrogen fluoride is 1,1,1,3,3-pentachloropropane or 1,1,3,3-tetrachloropropene.
    [0015] The present invention makes it possible to meet the need expressed above. It provides more particularly azeotropic or quasi-azeotropic compositions from compounds likely to be involved in the manufacture of various (hydro) halocarbon compounds, and in particular in the manufacture of HCFO-1233zdE.
    [0016] The identification of these azeotropic or quasi-azeotropic compositions thus makes it possible in particular to improve the efficiency and performance of processes for producing (hydro) halocarbon compounds, and in particular for producing HCFO-1233zdE. In a preferred embodiment, these compositions are heteroazeotropic, that is to say they are compositions whose condensed liquid forms two immiscible solutions which can be easily separated, for example by decantation. This has a considerable advantage for the purification operations envisaged.
    [0017] BRIEF DESCRIPTION OF THE FIGURES FIG. 1 represents the vapor pressure (in ordinate, in absolute bar) of the mixtures according to the invention according to example 1, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B and C correspond to various compositions of (hydro) halocarbon compounds (see Example 1). FIG. 2 represents the vapor pressure (in ordinate, in absolute bar) of mixtures according to the invention according to example 2, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C and D correspond to various compositions of (hydro) halocarbon compounds (see Example 2). FIG. 3 represents the vapor pressure (in ordinate, in absolute bar) of the mixtures according to the invention in accordance with example 3, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C and D correspond to various compositions of (hydro) halocarbon compounds (see Example 3). FIG. 4 represents the vapor pressure (in ordinate, in absolute bar) of mixtures according to the invention according to example 4, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C and D correspond to various compositions of (hydro) halocarbon compounds (see Example 4). FIG. 5 represents the vapor pressure (in ordinate, in absolute bar) of the mixtures according to the invention in accordance with Example 5, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C, D and E correspond to various compositions of (hydro) halocarbon compounds (see Example 5). FIG. 6 represents the vapor pressure (in ordinate, in absolute bar) of mixtures according to the invention in accordance with example 6, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C, D and E correspond to various compositions of (hydro) halocarbon compounds (see Example 6). FIG. 7 represents the vapor pressure (in ordinate, in absolute bar) of mixtures according to the invention according to example 7, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C, D and E correspond to various compositions of (hydro) halocarbon compounds (see Example 7). FIG. 8 represents the vapor pressure (in ordinate, in absolute bar) of mixtures according to the invention according to example 8, for the isotherm of 25 ° C. The abscissa shows the mass fraction of HF in the composition. Curves A, B, C, D, E and F correspond to various compositions of (hydro) halocarbon compounds (see Example 8). DESCRIPTION OF EMBODIMENTS OF THE INVENTION The invention is now described in more detail and in a nonlimiting manner in the description which follows. Unless otherwise stated all the proportions mentioned in the present application are mass proportions. The invention provides azeotropic, quaazeotropic, heteroazeotropic and quasi-heteroazeotropic compositions. A mixture is considered azeotropic when the pressure at the dew point is equal to that at the bubble-forming point, which means that the composition of the vapor is equal to that of the condensed liquid. A mixture is considered quasi-azeotropic when the dew point pressure is substantially equal to that at the bubble-forming point, which means that the vapor composition is substantially equal to that of the condensed liquid: for example the pressure difference between the dew point pressure and the bubble-forming point pressure is less than or equal to 5%, based on the pressure at the point of bubble formation.
    [0018] A hetero-azeotropic mixture is an azeotropic mixture of which the condensed liquid forms two immiscible solutions which can be easily separated, for example by decantation. A quasi-heteroazeotropic mixture is a quasi-azeotropic mixture whose condensed liquid forms two immiscible solutions which can be easily separated, for example by decantation. The compositions according to the invention comprise HF, HCFO-1233zdZ and one or more (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms. The (hydro) halocarbon compounds are compounds based on carbon atoms, halogen (s) and optionally hydrogen; advantageously, they are compounds based on carbon atoms, chlorine and / or fluorine, and optionally hydrogen. It is advantageously alkanes or alkenes partially or totally substituted by halogen atoms, especially chlorine and / or fluorine.
    [0019] According to a particular embodiment, the (hydro) halocarbon compounds which may be used in the context of the invention comprise 1 or 2 carbon atoms. They may especially be chosen from: - chloromethane (HCC-40); - chloropentafluoroethane (HCFC-115); chlorotetrafluoroethane (HFCF-124), namely 1-chloro-1,2,2,2-tetrafluoroethane and 1-chloro-1,1,2,2-tetrafluoroethane; pentafluoroethane (HFC-125); chlorotrifluoroethane, namely in particular 1-chloro-1,2,2-trifluoroethane (HCFC-133), 1-chloro-2,2,2-trifluoroethane (HCFC-133a) and 1-chloro-1 1,2-trifluoroethane (HCFC-133b); tetrafluoroethane, namely in particular 1,1,2,2-tetrafluoroethane (HFC-134) and 1,1,1,2-tetrafluoroethane (HFC-134a); chlorodifluoroethane, namely in particular 1-chloro-2,2-difluoroethane (HCFC-142), 1-chloro-1,2-difluoroethane (HCFC-142a) and 1-chloro-1,1-difluoroethane; (HCFC-142b); trifluoroethane, namely in particular 1,1,2-trifluoroethane (HFC-143) and 1,1,1-trifluoroethane (HFC-143a); difluoroethane, namely in particular 1,1-difluoroethane (HFC-152a) and 1,2-difluoroethane (HFC-152); difluoroethylene, namely 1,2-difluoroethylene (HFO-1132) and 1,1-difluoroethylene (HFO-1132a); and - fluoroethylene (HFO-1141). According to a particular embodiment, the (hydro) halocarbon compounds that may be used in the context of the invention comprise 3 carbon atoms. They may especially be chosen from: dichlorohexafluoropropane, namely in particular 1,2-dichloro-1,1,2,3,3,3-hexafluoropropane (HCFC-216ba), 1,3-dichloro-1, 1,2,2,3,3-hexafluoropropane (HCFC-216ca), 1,1-dichloro-1,2,2,3,3,3-hexafluoropropane (HCFC-216cb) and 2,2-dichloro- 1,1,1,3,3,3-hexafluoropropane (HCFC-216aa); chloroheptafluoropropane, namely in particular 1-chloro1,1,2,2,3,3,3-heptafluoropropane (HCFC-217ca) and 2-chloro-1,1,1,2,3,3,3 -heptafluoropropane (HCFC-217ba); octafluoropropane (HFC-218); dichloropentafluoropropane, namely in particular 2,2-dichloro-1,1,1,3,3-pentafluoropropane dichloro-1,1,1,2,3-pentafluoropropane dichloro-1, 1, 2,3,3-pentafluoropropane dichloro-1,1,1,2,2-pentafluoropropane dichloro-1,2,2,3-pentafluoropropane dichlo-1,2,2,3,3 -pentafluoropropane (HCFC-225aa), (HCFC-225ba), (HCFC-225bb), (HCFC-225ca), (HCFC-225cb), (HCFC-225cc), 2,3 1,2 3,3 1,3 1,1,1-Dichloro-1,1,3,3,3-pentafluoropropane (HCFC-225da), 1,3-dichloro-1,1,2,3,3-pentafluoropropane ( HCFC-225ea) and 1,1-dichloro-1,2,3,3,3-pentafluoropropane (HCFC-225eb); - chlorohexafluoropropane, namely in particular 2-chloro1,1,1,2,3,3-hexafluoropropane (HCFC-226ba), 3-chloro-1,1,1,2,2,3-hexafluoropropane (HCFCs -226ca), 1-chloro-1,1,2,2,3,3-hexafluoropropane (HCFC-226cb), 2-chloro-1,1,1,3,3,3-hexafluoropropane (HCFC-226cb), 226da) and 1-chloro-1,1,2,3,3,3-hexafluoropropane (HCFC-226ea); heptafluoropropane, namely in particular 1,1,2,2,3,3,3-heptafluoropropane (HFC-227ca) and 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ca); 227ea); dichlorotetrafluoropropane, namely in particular 2,2-dichloro-1,1,3,3-tetrafluoropropane (HCFC-234aa), 2,2-dichloro-1,1,1,3-tetrafluoropropane (HCFC-234ab) ), 1,2-dichloro-1,2,3,3-tetrafluoropropane (HCFC-234b), 2,3-dichloro-1,1,1,2-tetrafluoropropane (HCFC-234bb), 1,2-dichloro-1,2,3,3-tetrafluoropropane 1,1,2,3-tetrafluoropropane (HCFC-234bc), 1,3-dichloro-1,2,2,3-tetrafluoropropane (HCFC-234ca), 1,1-dichloro-2, 2,3,3-tetrafluoropropane (HCFC-234cb), 1,3-dichloro-1,1,2,2-tetrafluoropropane (HCFC-234cc), 1,1-dichloro-1,2,4 - tetrafluoropropane (HCFC-234cd), 2,3-dichloro-1,1,1,3-tetrafluoropropane (HCFC-234da), 1,3-dichloro-1,1,3,3-tetrafluoropropane (HCFC-234fa) ), 1,1-dichloro-1,3,3,3-tetrafluoropropane (HCFC-234fb), 1,1-dichloro-2,3,3,3-tetrafluoropropane (HCFC-234ea), 1 3-dichloro-1,1,2,3-tetrafluoropropane (HCFC-234eb) 1,1-dichloro-1,2,3,3-tetrafluoropropane (HCFC-234ec) and 1,2-dichloro-1, 1,3,3- tetraf luoropentane (HCFC-234db); Chloropentafluoropropane, namely in particular 1-chloro-1,2,2,3,3-pentafluoropropane (HCFC-235ca), 3-chloro-1,1,1,2,3-pentafluoropropane (HCFC 235ea), 1-chloro-1, 1,2,2,3-pentafluoropropane (HCFC-235cc), 2-chloro-1,1,1,3,3-1-chloro-1, 1, 3 , 3,3 -3-Chloro-1,1,1,2,2-2-chloro-1,1,2,3,3-2-chloro-1,1,1,2,3-pentafluoropropane ( HCFC-235bb); Hexafluoropropane, namely in particular 1,1,1,2,2,3-hexafluoropropane (HFC-236cb), 1,1,1,2,3,3-hexafluoropropane (HFC-236ea), 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) and 1,1,2,2,3,3-hexafluoropropane (HFC-236ca); Pentafluoropropane pentafluoropropane pentafluoropropane pentafluoropropane pentafluoropropane 1-chloro-1, 1,2, 3, 3- (HCFC-235da), (HCFC-235fa), (HCFC-235eb), (HCFC-235cb), ( HCFC-235ba) and tetrachlorofluoropropane, namely tetrachloro-1-fluoropropane (HCFC-241fa), 3-fluoropropane (HCFC-241fb), fluoropropane (HCFC-241ea), fluoropropane (HCFC-241eb), fluoropropane (HCFC-241da), fluoropropane (HCFC-241db), fluoropropane (HCFC-241dc), fluoropropane (HCFC-241ba), fluoropropane (HCFC-241bb), fluoropropane (HCFC-241aa), fluoropropane ( HCFC-241ab) and fluoropropane (HCFC-241ac); - trichlorodifluoropropane, namely in particular 1,1-difluoropropane (HCFC-242fa), difluoropropane (HCFC-242fb), difluoropropane (HCFC-242fc), difluoropropane (HCFC-242ea), difluoropropane (HCFC-242eb) , difluoropropane (HCFC-242ec), difluoropropane (HCFC-242da), difluoropropane (HCFC-242db), difluoropropane (HCFC-242dc), difluoropropane (HCFC-242dd), difluoropropane (HCFC-242dc), difluoropropane (HCFC-242cb), difluoropropane (HCFC-242b), difluoropropane (HCFC-242bb), difluoropropane (HCFC-242bc), difluoropropane (HCFC-242aa), difluoropropane (HCFC-242ab) and difluoropropane (HCFCs -242ac); dichlorotrifluoropropane, namely in particular 3,3,3-trifluoropropane (HCFC-243fa), trifluoropropane (HCFC-243fb), trifluoropropane (HCFC-243fc), trifluoropropane (HCFC-243ea), trifluoropropane (HCFC-243fc), 243eb), 1,3,3-trichloro-1,1,3-trichloro-1,3,1,1,1-trichloro-3,3-l, 1,3-trichloro-2,3-diol, 1,1,3-trichloro-1,2-l, 1,1-trichloro-2,3-1,2,3-trichloro-1,3-l, 1,2-trichloro-3,3-l, 2,3-trichloro-1,1,1,2-dichloro-13-1,1,3-trichloro-2,2-1,1,1-trichloro-2,2-1,2,3-diol 1,2-trichloro-1,2-trichloro-2,3-l, 1,2-trichloro-1,2-2,2,3-trichloro-1,1-1,2,2-trichloroethane 1,1,3,3-1,2,2-trichloro-1,1,1,1,3,3-le 1,1,1,3-tetrachloro, 1,3,3-tetrachloro-1-one. 1,1,3-tetrachloro-2-l, 1,2,3-tetrachloro-3,1,2,2,3-tetrachloro-1,1,1,2-tetrachloro-3 1, 1,2,3-tetrachloro-2,1,1,2-tetrachloro-1,2,2,3-tetrachloro-1,1,2,2-tetrachloro 1,1,2,2-tetrachloro-1-diol 1,1-dichloro-1,3-dichloro-1,1,3-1 , 1-Dichloro-1,3,3-1,3-dichloro-1,2,3-1,1-dichloro-2,3,3-1,3-dichloro-1,1,2-trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane trifluoropropane (HCFC-243ec), , (HCFC-243cb), (HCFC-243cc), (HCFC-243ba), (HCFC-243bb), (HCFC-243bc), (HCFC-243aa) and 1,1-dichloro- 1,2,3-1,2-dichloro-1,3,3-2,3-dichloro-1,1,1-1,2-dichloro-1,1,3-1,3-dichloro-1, 2,2-1,1-dichloro-2,2,3-1,1-dichloro-1,2,2-2,3-dichloro-1,1,2-1,2-dichloro-1,2, 3- 1,2-dichloro-1,1,2-2,2-dichloro-1,1,3-2,2-dichloro-3,3,3-trifluoropropane (HCFC-243ab); - chlorotetrafluoropropane, namely in particular 2-chloro-1,2,3,3-tetrafluoropropane (HCFC-244ba), (HCFC-244bb), (HCFC-244ca), (HCFC-244cb), (HCFC-244cc), (HCFC-244da), (HCFC-244db), (HCFC-244ea), (HCFC-244eb), (HCFC-244ec), (HCFC-244fa) and on 1-chloro-1, 1, 1,2-3-chloro-1, 1,2,2-1-chloro-1,2,2,3-1-chloro-1, 1,2,2 2-chloro-1, 1,3,3-2-chloro-1,1,1,3-3-chloro-1,1,2,3-3-chloro-1,1,1 2- [1-chloro-1,1,2,3-3-chloro-1,1,1,3-l-chloro-1,1,3,3-tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane tetrafluoropropane (HCFC-244fb); pentafluoropropane, namely in particular 1,1,2,2,3-pentafluoropropane (HFC-245ca), 1,1,2,3,3-pentafluoropropane (HFC-245ea), 1,1,1,2 3-pentafluoropropane (HFC-245eb), 1,1,1,2,2-pentafluoropropane (HFC-245cb) and 1,1,1,3,3-pentafluoropropane (HFC-245fa); chlorotrifluoropropane, namely in particular 2-chloro-1,2,3-trifluoropropane (HCFC-253ba), 2-chloro-1,1,2-trifluoropropane (HCFC-253bb), 1-chloro-2 2,3-trifluoropropane (HCFC-253ca), 1-chloro-1,2,2-trifluoropropane (HCFC-253cb), 3-chloro-1,1,2-trifluoropropane (HCFC-253ea), 1 -chloro-1,2,3-trifluoropropane (HCFC-253eb), 1-chloro-1,1,2-trifluoropropane (HCFC-253ec), 1-chloro-1,3,3-trifluoropropane (HCFC-253fa) ), 3-chloro-1,1,1-trifluoropropane (HCFC-253fb), 1-chloro-1,1,3-trifluoropropane (HCFC-253fc), 2-chloro-1,1,3-trifluoropropane (HCFC-253da) and 2-chloro-1,1,1-trifluoropropane (HCFC-253db); tetrafluoropropane, namely in particular 1,1,2,2-tetrafluoropropane (HFC-254cb), 1,1,1,3-tetrafluoropropane (HFC-254fb), 1,1,2,3-tetrafluoropropane (HFC-254ea), 1,1,1,2-tetrafluoropropane (HFC-254eb), 1,2,2,3-tetrafluoropropane (HFC-254ca) and 1,1,3,3-tetrafluoropropane (HFC -254fa); chlorodifluoropropane, namely in particular 1-chloro-2,2-difluoropropane (HCFC-262ca), 3-chloro-1,1-difluoropropane (HCFC-262fa), 1-chloro-1,3-difluoropropane (HCFC-262fb), 1-chloro-1,1-difluoropropane (HCFC-262fc), 1-chloro-2,3-difluoropropane (HCFC-262ea), 1-chloro-1,2-difluoropropane (HCFCs -262eb), 2-chloro-1,3-difluoropropane (HCFC-262da), 2-chloro-1,1-difluoropropane (HCFC-262db) and 2-chloro-1,2-difluoropropane (HCFC-262ba) ); trifluoropropane (HFC-263), namely in particular 1,1,1-trifluoropropane (HFC-263fb), 1,1,3-trifluoropropane (HFC-263fa), 1,2,3-trifluoropropane ( HFC-263ea), 1,1,2-trifluoropropane (HFC-263eb) and 1,2,2-trifluoropropane (HFC-263ca); dichlorotetrafluoropropene (HCFO-1214), namely in particular 1,2-dichloro-1,3,3,3-tetrafluoropropene (HCF0-1214xb), 1,1-dichloro-2,3,3,3- tetrafluoropropene (HCF0-1214ya), 1,3-dichloro-1,2,3,3-tetrafluoropropene (HCF0-1214yb), 2,3-dichloro-1,1,3,3-tetrafluoropropene (HCF0-1214xc) and 3,3-dichloro-1,1,2,3-tetrafluoropropene (HCF0-1214yc); chloropentafluoropropene (HCFO-1215), namely in particular 1-chloropentafluoropropene, 2-chloropentafluoropropene and 3-chloropentafluoropropene; hexafluoropropene (HFO-1216); dichlorotrifluoropropene (HCFO-1223), namely in particular 1,1-dichloro-3,3,3-trifluoropropene (HCF0-1223za), 1,2-dichloro-3,3,3-trifluoropropene (HCF0- 1223xd), 2,3-dichloro-1,3,3-trifluoropropene (HCF0-1223xe), 1,3-dichloro-2,3,3-trifluoropropene (HCFO-1223yd), 1,2-dichloro- 1,3,3-trifluoropropene (HCF0-1223xb), 2,3-dichloro-1,1,3-trifluoropropene (HCF0-1223xc), 1,1-dichloro-2,3,3-trifluoropropene (HCF0-1223xc), 1223a), 1,3-dichloro-1,2,3-trifluoropropene (HCF0-1223yb), 3,3-dichloro-1,1,2-trifluoropropene (HCF0-1223yc), 3,3-dichloroethane, 1,2,3-trifluoropropene (HCF0-1223ye), 1,3-dichloro-1,3,3-trifluoropropene (HCF0-1223zb) and 3,3-dichloro-1,1,3-trifluoropropene (HCF0-1223zb); 1223zc); chlorotetrafluoropropene (HCFO-1224), namely in particular 1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd), 1-chloro-1,3,3,3-tetrafluoropropene (HCF0- 1224zb), 2-chloro-1,3,3,3-tetrafluoropropene (HCF0-1224xe), 3-chloro-1,2,3,3-tetrafluoropropene (HCF0-1224ye), 3-chloro-1, 1,3,3-tetrafluoropropene (HCF0-1224zc), 2-chloro-1,1,3,3-tetrafluoropropene (HCF0-1224xc), 1-chloro-1,2,3,3-tetrafluoropropene (HCF0- 1224yb) and 3-chloro-1,1,2,3-tetrafluoropropene (HCF0-1224yc); pentafluoropropene, namely in particular 1,1,1,2,3-pentafluoropropene in trans form (HFO-1225yeE), 1,1,1,2,3-pentafluoropropene in cis form (HFO-1225yeZ), on 1 1,3,3,3-pentafluoropropene (HFO-1225zc) and 1,1,2,3,3-pentafluoropropene (HFO-12,225yc); trichlorofluoropropene (HCFO-1231), namely in particular 1,1,2-trichloro-3-fluoropropene (HCF0-1231xa), 1,2,3-trichloro-1-fluoropropene (HCF0-1231xb), 1,2,3-trichloro-3-fluoropropene (HCF0-1231xd), 2,3,3-trichloro-1-fluoropropene (HCF0-1231xe), 2,3,3-trichloro-3-fluoropropene (HCF0-1231xe), 1231xf), 1,1,3-trichloro-2-fluoropropene (HCF0-1231ya), 1,3,3-trichloro-2-fluoropropene (HCFO-1231yd), 3,3,3-trichloro-2-fluoropropene (HCF0-1231yf), 1,1,3-trichloro-3-fluoropropene (HCF0-1231za), 1,3,3-trichloro-1-fluoropropene (HFCO-1231zb), 1,3,3-trichloroethane, 3- fluoropropene (HCF0-1231zd) and 3,3,3-trichloro-1-fluoropropene (HCF0-1231ze); dichlorodifluoropropene (HCFO-1232), namely in particular 2,3-dichloro-3,3-difluoropropene (HCF0-1232xf), 1,2-dichloro-1,3-difluoropropene (HCF0-1232xb), 2,3-dichloro-1,1-difluoropropene (HCF0-1232xc), 1,2-dichloro-3,3-difluoropropene (HCF0-1232xd), 2,3-dichloro-1,3-difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene difluoropropene 14 (HCF0-1232xe), (HCF0-1232ya), (HCF0-1232yb), (HCFO-1232yd), (HCF0-1232ye), (HCF0-1232yf), ( HCF0-1232za), (HCF0-1232zb), (HCF0-1232zc), (HCFO-1232zd) and 1,1-dichloro-2,3,3-dichloro-1,2-1,3 2,3,4-dichloro-2,3-dichloro-1,2,3,3-dichloro-2,3-1,1-dichloro-3,3-1,3-dichloro-1,3- 3,3 1,1,3-dichloro-1,3-dichloro-3,3- 3,3-dichloro-1,3-difluoropropene (HCF0-1232ze); chlorotrifluoropropene, namely in particular 2-chloro-1,1,3-trifluoropropene (HCF0-1233xc), 2-chloro-1,3,3-trifluoropropene (HCF0-1233xe), (HCFO-1233yb), (HCF0-1233yc), (HCFO-1233yd), (HCF0-1233ye), (HCF0-1233yf), (HCFO-1233zb), (HCF0-1233zc), (HCF0-1233ze), (HCFO-1233xf) and the 1 3-chloro-1,2,3-trifluoropropene 3-chloro-1,2,4-trifluoropropene 1-chloro-2,3,3-trifluoropropene 3-chloro-1,2,3-trifluoropropene 3-chloro-2,3,3-trifluoropropene 1-chloro-1,3,3-trifluoropropene 3-chloro-1,1,3-trifluoropropene 3-chloro-1,3 3-trifluoropropene 2-chloro-3,3,3-trifluoropropene 1-chloro-3,3,3-trifuloropropene in trans form (HCF0-1233zdE); tetrafluoropropene, namely in particular 1,1,2,3-tetrafluoropropene (HFO-1234yc), 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,2,3,3-tetrafluoropropene (HF0-1234ye), 1,1,3,3-tetrafluoropropene (HF0-1234zc), 1,3,3,3-tetrafluoropropene in cis form (HFO-1234zeZ) and 1,3,3,3- tetrafluoropropene in trans form (HF0-1234zeE); chlorodifluoropropene (HCFO-1242), namely in particular 3-chloro-3,3-difluoropropene (HCF0-1242zf), 3-chloro-1,3-difluoropropene (HCF0-1242ze), 2-chloro 1,1-difluoropropene (HCF0-1242xc), 2-chloro-1,3-difluoropropene (HCF0-1242xe), 2-chloro-3,3-difluoropropene (HCF0-1242xf), 1-chloro-1, 2- difluoropropene (HCF0-1242yb), 1-chloro-2,3-difluoropropene (HCFO-1242yd), 3-chloro-1,2-difluoropropene (HCF0-1242ye), 3-chloro-2,3-diol difluoropropene (HCF0-1242yf), 1-chloro-1,3-difluoropropene (HCF0-1242zb), 3-chloro-1,1-difluoropropene (HCF0-1242zc) and 1-chloro-3,3-difluoropropene ( HCF0-1242zd); trifluoropropene, namely in particular 1,1,2-trifluoropropene (HFO-1243yc), 1,2,3-trifluoropropene (HFO-1243ye), 2,3,3-trifluoropropene (HFO-1243yf), 1,1,3-trifluoropropene (HFO-1243zc), 1,3,3-trifluoropropene (HFO-1243ze) and 3,3,3-trifluoropropene (HFO-1243zf); chlorofluoropropene (HCFO-1251), namely in particular 1-chloro-3-fluoropropene (HCF0-1251zd), 1-chloro-1-fluoropropene (HCF0-1251zb), 1-chloro-2-fluoropropene ( HCFO-1251yd), 2-chloro-1-fluoropropene (HCF0-1251xe), 2-chloro-3-fluoropropene (HCF0-1251yf), 3-chloro-2-fluoropropene (HCF0-1251xf), 3- chloro-1-fluoropropene (HCF0-1251zf) and difluoropropene (HFO-1252), namely, in particular 2,3-difluoropropene (HCF0-1252yf), 1,1-difluoropropene (HCF0-1252zc), 1,3difluoropropene (HCF0-1252ze) and 3,3-difluoropropene (HCF0-1252zf), and trifluoropropyne. The compositions according to the invention may be ternary mixtures, that is to say mixtures of three compounds and only three, The compositions according to the invention may be quaternary mixtures, that is to say mixtures of four compounds and only four. The compositions according to the invention may be five-year mixtures, i.e. mixtures of five compounds and only five.
    [0020] The compositions according to the invention may be senescence mixtures, that is to say mixtures of six compounds and only six. The compositions according to the invention may also be mixtures of seven compounds and only seven. The compositions according to the invention may also be mixtures of eight compounds and only eight. The compositions according to the invention may also be mixtures comprising more than eight compounds.
    [0021] According to one embodiment, the compositions according to the invention consist essentially of a mixture of HF, HCFO-1233zdZ and one or more (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms - the maximum amount of impurities , different from these compounds, for example being 2%, or 1%, or 0.5%, or 0.2%, or 0.1%, or 0.05%, or 0, 02% or 0.01%. According to one embodiment, the compositions according to the invention consist of a mixture of HF, HCFO-1233zdZ and one or more (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms. According to one embodiment, the abovementioned (hydro) halocarbon compounds used in the compositions according to the invention are chosen from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes, tetrafluoropropenes and their mixtures. According to one embodiment, the abovementioned (hydro) halocarbon compounds used in the compositions according to the invention are chosen from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HFC-245fa, HCFO-1232za, HCFO-1232zd, HCFO-1233zdE, HFO-1234zeZ and HFO-1234zeE. According to one embodiment, the above-mentioned (hydro) halocarbon compounds used in the compositions according to the invention are selected from HFC-245fa, HCFO-1233zdE, HFO-1234zeZ and HF0-1234zeE. According to one embodiment, the compositions according to the invention may consist (or consist essentially of) of a mixture of HF, HCFO-1233zdE and HCFO-1233zdZ. The HF content in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 4.0 bar absolute. Alternatively the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdE, HCFO-1233zdZ and one or more other (hydro) halocarbon compounds, which may be selected from the group of compounds listed below. above ; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HFC-245fa, HCFO-1232za, HCFO-1232zd, HFO-1234zeZ and HF0- 1234zeE; and which may more particularly be selected from HFC-245fa, HFO1234zeZ and HFO-1234zeE.
    [0022] According to one embodiment, the compositions according to the invention may consist (or consist essentially of) a mixture of HF, HCFO-1233zdE, HCFO-1233zdZ and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 4.4 bar absolute. Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdE, HCFO-1233zdZ, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen from the group consisting of compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HCFO-1232za, HCFO-1232zd, HFO-1234zeZ and HFO-1234zeE; and which may more particularly be selected from HFO-1234zeZ and HFO-1234zeE. According to one embodiment, the compositions according to the invention may consist (or consist essentially of) a mixture of HF, HCFO-1233zdZ, HFO-1234zeZ and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 4.8 bar absolute. Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HFO-1234zeZ, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen from the group consisting of compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HCFO-1232za, HCFO-1232zd, HCFO-1233zdE and HF0-1234zeE; and which may more particularly be selected from HCFO-1233zdE and HFO-1234zeE. According to one embodiment, the compositions according to the invention may consist (or consist essentially of) a mixture of HF, HCFO-1233zdZ, HFO-1234zeE and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 80%, and more preferably from 5 to 75%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 8.6 bar absolute.
    [0023] Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HFO-1234zeE, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen from the group consisting of compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HCFO-1232za, HCFO-1232zd, HCFO-1233zdE and HF0-1234zeZ; and which may more particularly be selected from HCFO-1233zdE and HFO-1234zeZ.
    [0024] According to one embodiment, the compositions according to the invention may consist (or consist essentially of) of a mixture of HF, HCFO-1233zdZ, HFO-1234zeE, HFO-1234zeZ and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 8.9 absolute bar. Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HFO-1234zeE, HFO-1234zeZ, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen among all the compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HCF0-1232za, HCFO-1232zd and HCF0-1233zdE; and which may especially be HCF0-1233zdE According to one embodiment, the compositions according to the invention may consist (or consist essentially of) a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeE and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 8.9 absolute bar. Alternatively the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeE, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen among all the compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HCFO-1232za, HCFO-1232zd and HF0-1234zeZ; and which may especially be the HFO-1234zeZ.
    [0025] According to one embodiment, the compositions according to the invention can consist (or consist essentially of) a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeZ and HFC-245fa. The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 4.8 bar absolute. Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeZ, HFC-245fa and one or more other (hydro) halocarbon compounds, which may be chosen among all the compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen especially from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, LI 9 chlorotrifluoropropenes and tetrafluoropropenes; and which may be especially selected from HCFC-241fa, HCFC242fa, HCFC-243fa, HCFC-244fa, HCFO-1232za, HCFO-1232zd and HF0-1234zeE; and which can in particular be the HFO-1234zeE. According to one embodiment, the compositions according to the invention may consist (or consist essentially of) a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeE, HFO-1234zeZ, and HFC-245fa . The content of HF in these compositions is advantageously from 1 to 85%, and more preferably from 5 to 80%. The boiling point is preferably 0 to 40 ° C for a pressure of 0.6 to 8.8 bar absolute. Alternatively, the compositions according to the invention may comprise a mixture of HF, HCFO-1233zdZ, HCFO-1233zdE, HFO-1234zeE, HFO-1234zeZ of HFC-245fa and one or more other (hydro) halocarbon compounds, which may be selected from the group of compounds listed above; and which may be chosen in particular from propanes and propenes partially or totally substituted by halogens; and which may be chosen in particular from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropenes, chlorotrifluoropropenes and tetrafluoropropenes; and which may be selected include HCFC 241fa, HCFC-242fa, HCFC-243fa, HCFC-244fa, HFO 1232za and HCFO-1232zd. In general, in the compositions according to the invention, the proportion of HF is preferably from 1 to 85%, especially from 5 to 80% (relative to the total weight of the composition), more particularly from 10 to 65%; and the proportion of (hydro) halocarbon compounds, including HCFO-1233zdZ, is 15 to 99%, especially 20 to 95%, more preferably 35 to 90%. The boiling point of a composition according to the invention is preferably from -20 ° C to 80 ° C for a pressure of 0.1 to 44 bar absolute; advantageously from 0 to 40 ° C for a pressure of 0.5 to 9 bar absolute. When the compositions according to the invention comprise both HCFO-1233zdZ and HCFO-1233zdE, these may comprise, in proportions by mass relative to the sum of these two compounds: HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE; HCF0-1233zdE. According to one embodiment, the compositions according to the invention, in the condensed state, comprise two liquid phases, preferably one richer in HF than the other. from 1 to 10% of HCFO-1233zdZ and from 90 to 99% of 10 to 20% of HCFO-1233zdZ and 80 to 90% of from 20 to 30% of HCFO-1233zdZ and from 70 to 80% of at 40% HCFO-1233zdZ and 60-70% 40-50% HCFO-1233zdZ and 50-60% 25-50-60% HCFO-1233zdZ and 40-50% from 60-50% 70% of HCFO-1233zdZ and 30 to 40% of 70 to 80% of HCFO-1233zdZ and 20 to 30% of 80 to 90% of HCFO-1233zdZ and 10 to 20% of 90 to 99% In particular, the use of HCFO-1233zdZ and 1-10% of the invention may be particularly useful in processes for the production of a fluorinated compound in which mixtures of the compounds described above can be produced. Such mixtures can then be treated by distillation in order to collect on the one hand a composition according to the invention, and on the other hand HF, or else on the other hand HCFO-1233zdZ, or else one or more several other (hydro) halocarbon compounds. Such mixtures may in particular be obtained as a product stream after a catalytic fluorination reaction of a chlorinated compound in a fluorinated compound with HF. By "chlorinated compound" (which represents the main reagent of the catalytic fluorination reaction) is meant an organic compound comprising one or more chlorine atoms, and by "fluorinated compound" (which represents the desired product of the catalytic fluorination reaction) ) is an organic compound comprising one or more fluorine atoms. It is understood that the chlorinated compound may comprise one or more fluorine atoms, and that the fluorinated compound may comprise one or more chlorine atoms. In general, the number of chlorine atoms of the fluorinated compound is less than the number of chlorine atoms of the chlorinated compound; and the number of fluorine atoms of the fluorinated compound is greater than the number of fluorine atoms of the chlorinated compound. The chlorinated compound may be an alkane or an alkene optionally having substituents selected from F, Cl, I and Br (preferably from F and Cl), and having at least one substituent Cl.
    [0026] The fluorinated compound may be an alkane or an alkene optionally having substituents chosen from F, Cl, I and Br (preferably from F and Cl), and comprising at least one substituent F. The chlorinated compound may in particular be an alkane with a or more substituents chlorine (hydrochlorocarbon or chlorocarbon) or an alkane with one or more substituents chlorine and fluorine (hydrochlorofluorocarbon or chlorofluorocarbon) or an alkene with one or more substituents chlorine (chloroolefin or hydrochlorohefin) or an alkene with one or more substituents chlorine and fluorine (hydrochlorofluoroolefin or chlorofluoroolefin).
    [0027] The fluorinated compound may in particular be an alkane with one or more fluorine substitutions (fluorocarbon or hydrofluorocarbon) or an alkane with one or more substituents chlorine and fluorine (hydrochlorofluorocarbon or chlorofluorocarbon) or an alkene with one or more fluorine substituents (fluoroolefin or hydrofluoroolefin) or an alkene with one or more substituents chlorine and fluorine (hydrochlorofluoroolefin or chlorofluoroolefin). According to one embodiment, the chlorinated compound and the fluorinated compound comprise a single carbon atom. According to one embodiment, the chlorinated compound and the fluorinated compound comprise two carbon atoms. According to a particularly preferred embodiment, the chlorinated compound and the fluorinated compound comprise three carbon atoms.
    [0028] The invention is particularly applicable to the following fluorination reactions: fluorination of 1,1,1,3,3-pentachloropropane to HCF0-1233zdE; fluorination of 1,1,3,3-tetrachloropropene to HCF0-1233zdE. The invention can be applied in particular to the determination of the decantation and purification steps necessary for the treatment of a gaseous flow leaving a liquid-phase fluorination reactor using 1,1,3,3-tetrachloropropene as raw material. or a gas phase fluorination reactor using 1,1,1,3,3-pentachloropropane as a raw material. This gas stream can contain between 15 and 50% of HF, between 15 and 50% of HCl and the complement consists of all the organic compounds resulting from the reaction. In one embodiment, a liquid phase fluorination process is carried out using 1,1,3,3-tetrachloropropene as raw material, and the distribution of the organic compounds at the end of the reaction may notably be as follows: 85 to 95% HCFO-1233zdE, 0 to 5% HCFO-1233zdZ, 0 to 3% HFO-1234zeE, 0 to 3% HFO-1234zeZ, 0 to 3% HFC-245fa, 0 to 3% HCFO-1232, 0 to 1% HCFC-243 and 0 to 1% HCFC-241. In one embodiment, a gas phase fluorination process is carried out using 1,1,1,3,3-pentachloropropane as raw material, and the distribution of the organic compounds at the end of the reaction may in particular be the following: 65 to 85% HCFO-1233zdE, 15 to 25% HCFO-1233zdZ, 0 to 10% HCFO-1232, 0 to 3% HFO-1234zeE, 0 to 3% HFO- 1234zeZ, 0 to 3% HFC-245fa, 0 to 3% HCFC-243. The compositions according to the invention have advantageous properties, in particular for the recycling of HF in the reaction stage. Thus, the condensed phase of these compositions, optionally when they are subjected to a distillation step and / or a liquid / liquid separation step, such as by decantation, forms two immiscible liquid phases. The richer phase of HF can be recycled to the reaction stage, while the less HF rich phase can be subjected to one or more distillation steps to separate the organic compounds and allow for example to be recycled to the reaction stage of the reaction stage. organic compounds which are reaction intermediates. EXAMPLES The following examples illustrate the invention without limiting it. Example 1 - Ternary composition HF / HCFO-1233zdE / HCFO-1233zdZ Azeotropic and heteroazeotropic behavior was observed for the ternary mixture HF / HCFO-1233zdE / HCFO-1233zdZ.
    [0029] Figure 1 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdE / HCFO-1233zdZ, namely: A: 95% HCFO-1233zdE and 5% HCFO-1233zdZ (relative to the total both) ; - B: 50% HCFO-1233zdE and 50% HCFO-1233zdZ (relative to the total of both); - C: 5% HCFO-1233zdE and 95% HCFO-1233zdZ (relative to the total of both). It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 4.0 bar absolute. Thus, for a mixture of HF with 50% HCFO-1233zdZ and 50% HCF0-1233zdE (the proportions being relative to the sum of the two), the boiling point is 0 ° C to about 0.9 bar. absolute, from 25 ° C to about 2.1 bar absolute and from 40 ° C to about 3.5 bar absolute. The settling ranges for a mixture of HF with 50% HCFO-1233zdZ and 50% HCFO-1233zdE (the proportions being relative to the sum of the two) are: 5 to 75% HF at 0 ° C; from 5 to 70% HF at 25 ° C; and 5 to 60% HF at 40 ° C. Example 2 - Quaternary Composition HF / HCFO-1233zdZ / HFO-1234zeE / 35 HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the quaternary mixture HF / HCFO-1233zdZ / HFO-1234zeE / HFC245fa.
    [0030] Figure 2 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdZ / HFO-1234zeE / HFC245fa, namely: - A: 5% HCFO-1233zdZ, 90% HFO-1234zeE and 5 % HFC-245fa (relative to the total of the three); - B: 40% HCFO-1233zdZ, 30% HFO-1234zeE and 30% HFC-245fa (relative to the total of the three); C: 5% HCFO-1233zdZ, 5% HFO-1234zeE and 90% HFC-245fa (relative to the total of the three); - D: 90% HCFO-1233zdZ, 5% HFO-1234zeE and 5% HFC-245fa (relative to the total of the three). It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 8.6 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdZ, HFO-1234zeE and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and 5 to 70% HF at 40 ° C. Example 3 - Quaternary Composition HF / HCFO-1233zdZ / HFO-1234zeZ / 20 HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the quaternary mixture HF / HCFO-1233zdZ / HFO-1234zeZ / HFC245fa. Figure 3 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdZ / HFO-1234zeZ / HFC-245fa, namely: - A: 5% HCFO-1233zdZ, 90% HFO- 1234zeZ and 5% HFC-245fa (relative to the total of the three); B: 5% HCFO-1233zdZ, 5% HFO-1234zeZ and 90% HFC-245fa (relative to the total of the three); - C: 40% HCFO-1233zdZ, 30% HFO-1234zeZ and 30% HFC-245fa (relative to the total of the three); - D: 90% HCFO-1233zdZ, 5% HFO-1234zeZ and 5% HFC-245fa (relative to the total of the three). It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 4.8 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdZ, HFO-1234zeZ and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and 5 to 75% HF at 40 ° C. Example 4 - Quaternary Composition HF / HCFO-1233zdE / HCFO-1233zdZ / HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the quaternary mixture HF / HCFO-1233zdE / HCFO-1233zdZ / HFC245fa. Figure 4 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdE / HCFO-1233zdZ / HFC-245fa, namely: - A: 5% HCFO-1233zdE, 5% HCFO-1233zdZ and 90% HFC-245fa (relative to the total of the three); B: 90% HCFO-1233zdE, 5% HCFO-1233zdZ and 5% HFC-245fa (relative to the total of the three); - C: 40% HCFO-1233zdE, 30% HCFO-1233zdZ and 30% HFC-245fa (relative to the total of the three); - D: 5% HCFO-1233zdE, 90% HCFO-1233zdZ and 5% HFC-245fa (relative to the total of the three).
    [0031] It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 4.4 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdE, HCFO-1233zdZ and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and 5 to 75% HF at 40 ° C. Example 5 - Five-year composition HF / HCFO-1233zdZ / HFO-1234zeE / HFO-1234zeZ / HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the five-year mixture HF / HCFO-1233zdZ / HFO-1234zeE / HFO-1234zeZ / HFC-245fa. Figure 5 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdZ / HFO-1234zeE / HFO1234zeZ / HFC-245fa, namely: - A: 1% HCFO-1233zdZ, 97% HFO -1234zeE, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of the four); B: 25% HCFO-1233zdZ, 25% HFO-1234zeE, 25% HFO-1234zeZ and 25% HFC-245fa (relative to the total of the four); - C: 1% HCFO-1233zdZ, 1% HFO-1234zeE, 97% HFO-1234zeZ and 1% HFC-245fa (relative to the total of the four); - D: 1% HCFO-1233zdZ, 1% HFO-1234zeE, 1% HFO1234zeZ and 97% HFC-245fa (relative to the total of the four); E: 97% HCFO-1233zdZ, 1% HFO-1234zeE, 1% HFO1234zeZ and 1% HFC-245fa (relative to the total of the four).
    [0032] It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 8.9 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdZ, HFO-1234zeE, HFO-1234zeZ and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and from 5 to 65% HF at 40 ° C. Example 6 - Five-year composition HF / HCFO-1233zdE / HCF0-1233zdZ / HFO-1234zeE / HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the five-year mixture HF / HCFO-1233zdE / HCFO-1233zdZ / HFO-1234zeE / HFC-245fa. Figure 6 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdE / HCFO-1233zdZ / HFO1234zeE / HFC-245fa, namely: - A: 1% HCFO-1233zdE, 1% HCFO -1233zdZ, 97% HFO-1234zeE and 1% HFC-245fa (relative to the total of the four); B: 25% HCFO-1233zdE, 25% HCFO-1233zdZ, 25% HFO-1234zeE and 25% HFC-245fa (relative to the total of the four); - C: 1% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO1234zeE and 97% HFC-245fa (relative to the total of the four); - D: 97% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO-1234zeE and 1% HFC-245fa (relative to the total of four); - E: 1% HCFO-1233zdE, 97% HCFO-1233zdZ, 1% HFO-1234zeE and 1% HFC-245fa (relative to the total of the four).
    [0033] It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 8.9 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdE, HCFO-1233zdZ, HFO-1234zeE and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and from 5 to 65% HF at 40 ° C. Example 7 - Five-year composition HF / HCFO-1233zdE / HCFO-1233zdZ / HFO-1234zeZ / HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the five-year mixture HF / HCFO-1233zdE / HCF0-1233zdZ / HFO1234zeZ / HFC- 245fa. Figure 7 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdE / HCFO-1233zdZ / HFO-1234zeZ / HFC-245fa, namely: - A: 1% HCFO-1233zdE, 1% of HCFO-1233zdZ, 97% HFO-1234zeZ and 1% HFC-245fa (relative to the total of the four); B: 1% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO-1234zeZ and 97% HFC-245fa (relative to the total of the four); C: 25% HCFO-1233zdE, 25% HCFO-1233zdZ, 25% HFO-1234zeZ and 25% HFC-245fa (relative to the total of the four); - D: 97% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of the four); - E: 1% HCFO-1233zdE, 97% HCFO-1233zdZ, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of the four).
    [0034] It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 4.8 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdE, HCFO-1233zdZ, HFO-1234zeZ and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and 5 to 70% HF at 40 ° C. Example 8 - Senary Composition HF / HCFO-1233zdE / HCFO-1233zdZ / HFO-1234zeE / HFO-1234zeZ / HFC-245fa Azeotropic and heteroazeotropic behavior was observed for the senile mixture HF / HCFO-1233zdE / HCFO-1233zdZ / HFO1234zeE / HFO-1234zeZ / HFC-245fa. Figure 8 illustrates the azeotropic behavior for the isotherm at 25 ° C, for various proportions HCFO-1233zdE / HCFO-1233zdZ / HFO-1234zeE / HFO-1234zeZ / HFC-245fa, namely: - A: 1% HCFO- 1233zdE, 1% HCFO-1233zdZ, 96% HFO-1234zeE, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of five); B: 20% HCFO-1233zdE, 20% HCFO-1233zdZ, 20% HFO-1234zeE, 20% HFO-1234zeZ and 20% HFC-245fa (relative to the total of five); - C: 1% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO1234zeE, 96% HFO-1234zeZ and 1% HFC-245fa (relative to the total of five); - D: 1% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO1234zeE, 1% HFO-1234zeZ and 96% HFC-245fa (relative to the total of five); E: 96% HCFO-1233zdE, 1% HCFO-1233zdZ, 1% HFO-1234zeE, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of five); - F: 1% HCFO-1233zdE, 96% HCFO-1233zdZ, 1% HFO-1234zeE, 1% HFO-1234zeZ and 1% HFC-245fa (relative to the total of five).
    [0035] It is found that the composition has a boiling point of 0 to 40 ° C for a pressure of 0.6 bar absolute to 8.8 bar absolute. The settling ranges for a mixture comprising equal mass proportions of HCFO-1233zdE, HCFO-1233zdZ, HFO-1234zeE, HFO-1234zeZ and HFC-245fa are: from 5 to 80% HF at 0 ° C; from 5 to 75% HF at 25 ° C; and from 5 to 65% HF at 40 ° C.
    权利要求:
    Claims (10)
    [0001]
    REVENDICATIONS1. Azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene and one or more (hydro) halocarbon compounds having 1 to 3 carbon atoms.
    [0002]
    2. Composition according to claim 1, wherein the (hydro) halocarbon compounds have 3 carbon atoms, and are preferably chosen from propanes and propenes partially or totally substituted by halogens.
    [0003]
    3. Composition according to claim 1 or 2, wherein the (hydro) halocarbon compounds are selected from tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, chlorotetrafluoropropanes, pentafluoropropanes, dichlorodifluoropropènes, chlorotrifluoropropènes and tétrafluoropropènes.
    [0004]
    4. Composition according to one of claims 1 to 3, comprising hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3,3,3-trifluoro-1-chloropropene and one or more other (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms.
    [0005]
    5. Composition according to one of claims 1 to 4, comprising hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-1,3,3,3-tetrafluoropropene and one or several other (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms.
    [0006]
    6. Composition according to one of claims 1 to 5, comprising hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene and one or several other (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms.
    [0007]
    7. Composition according to one of claims 1 to 6, comprising hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, 1,1,1,3,3-pentafluoropropane and one or several other (hydro) halocarbon compounds comprising from 1 to 3 carbon atoms.
    [0008]
    8. Composition according to one of claims 1 to 7, which is a ternary mixture, and preferably is a mixture of hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene and E-3 3,3-trifluoro-1-chloropropene.
    [0009]
    9. Composition according to one of claims 1 to 7, which is a quaternary mixture, and preferably is a mixture of: - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E -3,3,3-trifluoro-1-chloropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane.
    [0010]
    10. Composition according to one of claims 1 to 7, which is a mixture of five years, and preferably is a mixture of: - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E -3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene and 1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, E-3,3,3-trifluoro-1-chloropropene, E-1,3,3,3-tetrafluoropropene and 1, 1,1,3,3-pentafluoropropane; or - hydrogen fluoride, Z-3,3,3-trifluoro-1-chloropropene, Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane.11. A composition according to any one of claims 1 to 7, which is a senile mixture, and is preferably a mixture of: hydrogen fluoride, Z-3,3,3. 1-trifluoro-1-chloropropene, 3,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoropropene, and 1,1,3,3-tetrafluoropropene , 1,3,3-pentafluoropropane. Composition according to one of Claims 1 to 11, which is heteroazeotropic or quasi-heteroazeotropic. Composition according to one of claims 1 to 12, which comprises from 1 to 85% by weight, preferably from 1 to 80% by weight, more preferably from 5 to 80% by weight and very particularly preferably from 5-75% by weight of hydrogen fluoride; and / or from 15 to 99% by weight, preferably from 20 to 99% by weight, more preferably from 20 to 95% by weight and most preferably from 25 to 95% by weight of compounds (hydro ) halocarbons having 1 to 3 carbon atoms. Composition according to one of Claims 1 to 13, having a boiling point of 0 to 40 ° C for a pressure of 0.5 to 9 bar absolute. A process for producing a main (hydro) halocarbon compound, comprising: forming a mixture of compounds comprising hydrogen fluoride, 2,3,3,3-trifluoro-1-chloropropene and one or more other compounds (hydro) halocarbons; the distillation of this mixture, allowing to collect on the one hand an azeotropic composition according to one of claims 1 to 14, and on the other hand at least one of the compounds of the mixture. 16. The method according to claim 15, in which the distillation makes it possible to collect, on the one hand, an azeotropic composition according to one of claims 1 to 14, and on the other hand fluoride d. hydrogen; or on the one hand an azeotropic composition according to one of claims 1 to 14, and on the other hand E3,3,3-trifluoro-1-chloropropene. A process according to claim 15 or 16, which is a process for producing 3,3,3-trifluoro-1-chloropropene, and preferably E-3,3,3-trifluoro-1-chloropropene. Process according to one of claims 15 to 17, wherein the mixture of compounds is obtained following a fluorination step, comprising the reaction of a chlorinated compound with hydrogen fluoride. Process according to one of Claims 15 to 18, in which the azeotropic composition collected is separated, preferably by decantation, into two immiscible liquid fractions, namely a fraction rich in hydrogen fluoride and a fraction which is low in fluoride. hydrogen, the hydrogen fluoride-rich fraction containing a higher proportion of hydrogen fluoride than the low hydrogen fluoride fraction; and the fraction rich in hydrogen fluoride being optionally recycled to the fluorination stage. Process according to one of Claims 15 to 19, in which the chlorinated compound is 1,1,1,3,3-pentachloropropane or 1,1,3,3-tetrachloropropene.
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    同族专利:
    公开号 | 公开日
    CN105829270B|2018-06-19|
    US20170297982A1|2017-10-19|
    CN105829270A|2016-08-03|
    WO2015092211A1|2015-06-25|
    US20180297919A1|2018-10-18|
    JP6606499B2|2019-11-13|
    MX2016007254A|2016-09-07|
    JP2017504604A|2017-02-09|
    FR3015478B1|2015-12-25|
    EP3083537A1|2016-10-26|
    US10029961B2|2018-07-24|
    EP3083537B1|2018-05-23|
    ES2675146T3|2018-07-09|
    US10590052B2|2020-03-17|
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    法律状态:
    2015-11-10| PLFP| Fee payment|Year of fee payment: 3 |
    2016-11-11| PLFP| Fee payment|Year of fee payment: 4 |
    2017-11-13| PLFP| Fee payment|Year of fee payment: 5 |
    2018-11-20| PLFP| Fee payment|Year of fee payment: 6 |
    2020-10-16| ST| Notification of lapse|Effective date: 20200910 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1362982A|FR3015478B1|2013-12-19|2013-12-19|AZEOTROPIC COMPOSITIONS BASED ON HYDROGEN FLUORIDE AND Z-3,3,3-TRIFLUORO-1-CHLOROPROPENE|FR1362982A| FR3015478B1|2013-12-19|2013-12-19|AZEOTROPIC COMPOSITIONS BASED ON HYDROGEN FLUORIDE AND Z-3,3,3-TRIFLUORO-1-CHLOROPROPENE|
    CN201480069887.8A| CN105829270B|2013-12-19|2014-12-09|The Azeotrope compositions of tri- fluoro- 1- chloropropenes of hydrogen fluoride and Z-3,3,3-|
    US15/104,836| US10029961B2|2013-12-19|2014-12-09|Azeotropic compositions of hydrogen fluoride and Z-3,3,3-trifluoro-1-chloropropene|
    PCT/FR2014/053228| WO2015092211A1|2013-12-19|2014-12-09|Azeotropic compositions of hydrogen fluoride and z-3,3,3-trifluoro-1-chloropropene|
    ES14827806.2T| ES2675146T3|2013-12-19|2014-12-09|Azeotropic compositions based on hydrogen fluoride and Z-3,3,3-trifluoro-1-chloropropene|
    JP2016541417A| JP6606499B2|2013-12-19|2014-12-09|Azeotropic composition of hydrogen fluoride and Z-3,3,3-trifluoro-1-chloropropene|
    MX2016007254A| MX2016007254A|2013-12-19|2014-12-09|Azeotropic compositions of hydrogen fluoride and z-3,3,3-trifluoro-1-chloropropene.|
    EP14827806.2A| EP3083537B1|2013-12-19|2014-12-09|Azeotropic compositions of hydrogen fluoride and z-3,3,3-trifluoro-1-chloropropene|
    US16/018,191| US10590052B2|2013-12-19|2018-06-26|Azeotropic compositions of hydrogen fluoride and Z-3,3,3-trifluoro-1-chloropropene|
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