The present invention relates to azeotropic or quasi-azeotropic compositions comprising 3,3,3-trifluoropropene and hydrogen fluoride. These compositions may originate from intermediate compositions in the production of 3,3,3-trifluoropropene and are generally useful in processes for recycling hydrogen fluoride.
The manufacture of 3,3,3-trifluoropropene accompanied by a multitude of by-products, having a boiling point close to HFO-1243zf, leads to relatively complex and expensive purification steps. The difficulty encountered during the purification of HFO-1243zf generally implies an appreciable loss of desired product. Furthermore, these by-products may form azeotropic compositions with 1,3,3,3-tetrafluoropropene, making separation by distillation simple, very difficult, or even impossible.
Fluids based on 3,3,3-trifluoropropene have found numerous applications in varied industrial fields, especially as heat-transfer fluid, propellants, foaming agents, swelling agents, gaseous dielectrics, polymerization medium or monomer, support fluids, abrasive agents, drying agents and fluids for power production units.
Particular importance is given to fluids that have a low impact on the environment.
The subject of the present invention is an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 3,3,3-trifluoropropene and one or more (hydro)halocarbon compounds comprising between 1 and 3 carbon atoms. According to one embodiment of the invention, the composition is heteroazeotropic or quasi-heteroazeotropic.
A heteroazeotropic or quasi-heteroazeotropic mixture is an azeotropic or quasi-azeotropic mixture in which the condensed liquid forms two immiscible solutions that can be readily separated, for example by decantation.
The term “quasi-azeotropic” or “quasi-heteroazeotropic” has a broad meaning and is intended to include compositions that are strictly azeotropic or strictly heteroazeotropic and those that behave like an azeotropic or heteroazeotropic mixture.
A mixture is azeotropic when the pressure at the dew point is equal to that at the bubble formation point, which means that the vapor composition is equal to that of the condensed liquid.
A mixture is considered as quasi-azeotropic when the pressure at the dew point is substantially equal to that at the bubble formation point, which means that the vapor composition is substantially equal to that of the condensed liquid.
Another way of characterizing a mixture as quasi-azeotropic when the pressure difference between the pressure at the dew point and the pressure at the bubble formation point is low, preferentially less than or equal to 5%, on the basis of the pressure at the bubble formation point.
The compositions according to the invention especially concern the following compounds, the acronyms of which represent:
The composition according to the invention may optionally be a mixture of one or more azeotropes and/or heteroazeotropes of ternary, quaternary, penternary systems, systems with six compounds, systems with seven compounds, systems with eight or more compounds.
The compound(s) containing 1 and/or 2 carbon atoms may be chosen especially from chloromethane, chloropentafluoroethane, 1-chloro-1,2,2,2-tetrafluoroethane, 1-chloro-1,1,2,2-tetrafluoroethane, pentafluoroethane, 1-chloro-1,2,2-trifluoroethane, 1-chloro-2,2,2-trifluoroethane, 1,1,2,2-tetrafluoroethane, 1,1,1,2-tetrafluoroethane, 1-chloro-1,2-difluoroethane, 1-chloro-1,1-difluoroethane, 1,1,2-trifluoroethane, 1,1,1-trifluoroethane, 1,1,2-trifluoroethane, 1,1-difluoroethane, 1,2-difluoroethylene and fluoroethylene.
The compound(s) containing 3 carbon atoms may be chosen especially from 1,2-dichloro-1,1,2,3,3,3-hexafluoropropane, 1,3-dichloro-1,1,2,2,3,3-hexafluoropropane, 1,1-dichloro-1,2,2,3,3,3-hexafluoropropane, 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane, 1-chloro-1,1,2,2,3,3,3-heptafluoropropane, 2-chloro-1,1,1,2,3,3,3-heptafluoropropane, octafluoropropane, dichloropentafluoropropane, 2,2-dichloro-1,1,1,3,3-pentafluoropropane, 2,3-dichloro-1,1,1,2,3-pentafluoropropane, 1,2-dichloro-1,1,2,3,3-pentafluoropropane, 3,3-dichloro-1,1,1,2,2-pentafluoropropane, 1,3-dichloro-1,1,2,2,3-pentafluoropropane, 1,1-dichloro-1,2,2,3,3-pentafluoropropane, 1,2-dichloro-1,1,3,3,3-pentafluoropropane, 1,3-dichloro-1,1,2,3,3-pentafluoropropane, 1,1-dichloro-1,2,3,3,3-pentafluoropropane, chlorohexafluoropropane, 2-chloro-1,1,1,2,3,3-hexafluoropropane, 3-chloro-1,1,1,2,2,3-hexafluoropropane, 1-chloro-1,1,2,2,3,3-hexafluoropropane, 2-chloro-1,1,1,3,3,3-hexafluoropropane, 1-chloro-1,1,2,3,3,3-hexafluoropropane, 1,1,2,2,3,3,3-heptafluoropropane, 1,1,1,2,3,3,3-Heptafluoropropane, dichlorotetrafluoropropane, 2,2-dichloro-1,1,3,3-tetrafluoropropane, 2,2-dichloro-1,1,1,3-tetrafluoropropane, 1,2-dichloro-1,2,3,3-tetrafluoropropane, 2,3-dichloro-1,1,1,2-tetrafluoropropane, 1,2-dichloro-1,1,2,3-tetrafluoropropane, 1,3-dichloro-1,2,2,3-tetrafluoropropane, 1,1-dichloro-2,2,3,3-tetrafluoropropane, 1,3-dichloro-1,1,2,2-tetrafluoropropane, 1,1-dichloro-1,2,2,3-tetrafluoropropane, 2,3-dichloro-1,1,1,3-tetrafluoropropane, 1,3-dichloro-1,1,3,3-tetrafluoropropane, 1,3-dichloro-1,1,3,3-tetrafluoropropane, 1,1-dichloro-1,3,3,3-tetrafluoropropane, 1,1-dichloro-2,3,3,3-tetrafluoropropane, 1,3-dichloro-1,1,2,3-tetrafluoropropane, 1,1-dichloro-1,2,3,3-tetrafluoropropane, chloropentafluoropropane, 1-chloro-1,2,2,3,3-pentafluoropropane, 3-chloro-1,1,1,2,3-pentafluoropropane, 1-chloro-1,1,2,2,3-pentafluoropropane, 2-chloro-1,1,1,3,3-pentafluoropropane, 1-chloro-1,1,3,3,3-pentafluoropropane, 1-chloro-1,1,2,3,3-pentafluoropropane, 3-chloro-1,1,1,2,2-pentafluoropropane, 2-chloro-1,1,2,3,3-pentafluoropropane, 2-chloro-1,1,1,2,3-pentafluoropropane, 1,1,1,2,2,3-hexafluoropropane, 1,1,1,2,3,3-hexafluoropropane, 1,1,1,3,3,3-hexafluoropropane, 1,1,2,2,3,3-hexafluoropropane, dichlorotrifluoropropane, 1,1-dichloro-3,3,3-trifluoropropane, 1,3-dichloro-1,1,3-trifluoropropane, 1,1-dichloro-1,3,3-trifluoropropane, 1,3-dichloro-1,2,3-trifluoropropane, 1,1-dichloro-2,3,3-trifluoropropane, 1,3-dichloro-1,1,2-trifluoropropane, 1,1-dichloro-1,2,3-trifluoropropane, 1,2-dichloro-1,3,3-trifluoropropane, 2,3-dichloro-1,1,1-trifluoropropane, 1,2-dichloro-1,1,3-trifluoropropane, 1,3-dichloro-1,2,2-trifluoropropane, 1,1-dichloro-2,2,3-trifluoropropane, 1,1-dichloro-1,2,2-trifluoropropane, 2,3-dichloro-1,1,2-trifluoropropane, 1,2-dichloro-1,2,3-trifluoropropane, 1,2-dichloro-1,1,2-trifluoropropane, 2,2-dichloro-1,1,3-trifluoropropane, 2,2-dichloro-3,3,3-trifluoropropane, chlorotetrafluoropropane, 2-chloro-1,2,3,3-tetrafluoropropane, 2-chloro-1,1,1,2-tetrafluoropropane, 3-chloro-1,1,2,2-tetrafluoropropane, 1-chloro-1,2,2,3-tetrafluoropropane, 1-chloro-1,1,2,2-tetrafluoropropane, 2-chloro-1,1,3,3-tetrafluoropropane, 2-chloro-1,1,1,3-tetrafluoropropane, 3-chloro-1,1,2,3-tetrafluoropropane, 3-chloro-1,1,1,2-tetrafluoropropane, 1-chloro-1,1,2,3-tetrafluoropropane, 3-chloro-1,1,1,3-tetrafluoropropane, 1-chloro-1,1,3,3-tetrafluoropropane, pentafluoropropane, 1,1,2,2,3-pentafluoropropane, 1,1,2,3,3-pentafluoropropane, 1,1,1,2,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, chlorotrifluoropropane, 2-chloro-1,2,3-trifluoropropane, 2-chloro-1,1,2-trifluoropropane, 1-chloro-2,2,3-trifluoropropane, 1-chloro-1,2,2-trifluoropropane, 3-chloro-1,1,2-trifluoropropane, 1-chloro-1,2,3-trifluoropropane, 1-chloro-1,1,2-trifluoropropane, 3-chloro-1,3,3-trifluoropropane, 3-chloro-1,1,1-trifluoropropane, 1-chloro-1,1,3-trifluoropropane, 2-chloro-1,1,3-trifluoropropane, 2-chloro-1,1,1-trifluoropropane, 1,1,2,2-tetrafluoropropane, 1,1,1,3-tetrafluoropropane, 1,1,2,3-tetrafluoropropane, 1,1,1,2-tetrafluoropropane, 1,2,2,3-tetrafluoropropane, 1,1,3,3-tetrafluoropropane, chlorodifluoropropane, 1-chloro-2,2-difluoropropane, 3-chloro-1,1-difluoropropane, 1-chloro-1,3-difluoropropane, 1-chloro-1,1-difluoropropane, 1-chloro-2,3-difluoropropane, 1-chloro-1,2-difluoropropane, 2-chloro-1,3-difluoropropane, 2-chloro-1,1-difluoropropane, 2-chloro-1,2-difluoropropane, trifluoropropane, 1,1,1-trifluoropropane, 1,1,3-trifluoropropane, 1,2,3-trifluoropropane, 1,1,2-trifluoropropane, 1,2,2-trifluoropropane, dichlorotetrafluoropropene, 1,2-dichloro-1,3,3,3-tetrafluoropropene, 1,1-dichloro-2,3,3,3-tetrafluoropropene, 1,3-dichloro-1,2,3,3-tetrafluoropropene, 2,3-dichloro-1,1,3,3-tetrafluoropropene, 3,3-dichloro-1,1,2,3-tetrafluoropropene, chloropentafluoropropene, 1-chloropentafluoropropene, 2-chloropentafluoropropene, 3-chloropentafluoropropene, hexafluoropropene, dichlorotrifluoropropene, 1,1-dichloro-3,3,3-trifluoropropene, 1,2-dichloro-3,3,3-trifluoropropene, 2,3-dichloro-1,3,3-trifluoropropene, 1,3-dichloro-2,3,3-trifluoropropene, 1,2-dichloro-1,3,3-trifluoropropene, 2,3-dichloro-1,1,3-trifluoropropene, 1,1-dichloro-2,3,3-trifluoropropene, 1,3-dichloro-1,2,3-trifluoropropene, 3,3-dichloro-1,1,2-trifluoropropene, 3,3-dichloro-1,2,3-trifluoropropene, 1,3-dichloro-1,3,3-trifluoropropene, 3,3-dichloro-1,1,3-trifluoropropene, 1-chloro-2,3,3,3-tetrafluoropropene, 1-chloro-1,3,3,3-tetrafluoropropene, 2-chloro-1,3,3,3-tetrafluoropropene, 3-chloro-1,2,3,3-tetrafluoropropene, 3-chloro-1,1,3,3-tetrafluoropropene, 2-chloro-1,1,3,3-tetrafluoropropene, 1-chloro-1,2,3,3-tetrafluoropropene, 3-chloro-1,1,2,3-tetrafluoropropene, 1,2,3,3,3-pentafluoropropene, 1,1,3,3,3-pentafluoropropene, 1,1,2,3,3-pentafluoropropene, dichlorodifluoropropene, 2,3-dichloro-3,3-difluoropropene, 1,2-dichloro-1,3-difluoropropene, 2,3-dichloro-1,1-difluoropropene, 1,2-dichloro-3,3-difluoropropene, 2,3-dichloro-1,3-difluoropropene, 1,1-dichloro-2,3-difluoropropene, 1,3-dichloro-1,2-difluoropropene, 1,3-dichloro-2,3-difluoropropene, 3,3-dichloro-1,2-difluoropropene, 3,3-dichloro-2,3-difluoropropene, 1,1-dichloro-3,3-difluoropropene, 1,3-dichloro-1,3-difluoropropene, 3,3-dichloro-1,1-difluoropropene, 1,3-dichloro-3,3-difluoropropene, 3,3-dichloro-1,3-difluoropropene, chlorotrifluoropropene, 2-chloro-1,1,3-trifluoropropene, 2-chloro-1,3,3-trifluoropropene, 1-chloro-1,2,3-trifluoropropene, 3-chloro-1,1,2-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, 1,1,2,3-tetrafluoropropene, 1,2,3,3-tetrafluoropropene, 1,1,3,3-tetrafluoropropene, chlorodifluoropropene, 3-chloro-3,3-difluoropropene, 3-chloro-1,3-difluoropropene, 2-chloro-1,1-difluoropropene, 2-chloro-1,3-difluoropropene, 2-chloro-3,3-difluoropropene, 1-chloro-1,2-difluoropropene, 1-chloro-2,3-difluoropropene, 3-chloro-1,2-difluoropropene, 3-chloro-2,3-difluoropropene, 1-chloro-1,3-difluoropropene, 3-chloro-1,1-difluoropropene, 1-chloro-3,3-difluoropropene, trifluoropropene, 1,1,2-trifluoropropene, 1,2,3-trifluoropropene, 2,3,3-trifluoropropene, 1,1,3-trifluoropropene, 1,3,3-trifluoropropene, chlorofluoropropene, 1-chloro-3-fluoropropene, 1-chloro-1-fluoropropene, 1-chloro-2-fluoropropene, 2-chloro-1-fluoropropene, 2-chloro-3-fluoropropene, 3-chloro-2-fluoropropene, 3-chloro-1-fluoropropene, 3-chloro-3-fluoropropene, difluoropropene, 1,2-difluoropropene, 2,3-difluoropropene, 1,1-difluoropropene, 1,3-difluoropropene, 3,3-difluoropropene, 1,1,1,2,2-pentafluoropropane, E-1,3,3,3-tetrafluoropropene, Z-1,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, Z-3,3,3-trifluoro-1-chloropropene and trifluoropropyne.
A subject of the present invention is also an azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 3,3,3-trifluoropropene, and one or more compounds chosen from 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
A subject of the present invention is also a composition comprising hydrogen fluoride, 3,3,3-trifluoropropene and at least one or more organic compounds chosen from E-1,3,3,3-tetrafluoropropene, Z-1,3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane and 2,3,3,3-tetrafluoropropene.
According to one embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,2-heptafluoropropane and optionally one or more compounds chosen from 2,3,3,3-tetrafluoropropene, E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene and optionally one or more compounds chosen from E-3,3,3-trifluoro-1-chloropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-3,3,3-trifluoro-1-chloropropene and optionally one or more compounds chosen from 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene and optionally one or more compounds chosen from 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,3,3,3-tetrafluoropropene and optionally one or more compounds chosen from trifluoropropyne, 1,1,1,3,3-pentafluoropropene, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, trifluoropropyne and optionally one or more compounds chosen from 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,3,3-pentafluoropropane and optionally one or more compounds chosen from 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,3,3-pentafluoropropene and optionally one or more compounds chosen from 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,3-pentafluoropropene and optionally 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-1,3,3,3-tetrafluoropropene and optionally one or more compounds chosen from Z-1,3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment of the invention, the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, Z-1,3,3,3-tetrafluoropropene and optionally one or more compounds chosen from 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene and optionally one or more compounds chosen from E-3,3,3-trifluoro-1-chloropropene, 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment of the invention, the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, E-3,3,3-trifluoro-1-chloropropene and optionally one or more compounds chosen from 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to another embodiment, the composition according to the invention comprises hydrogen fluoride, 3,3,3-trifluoropropene, 1,1,1,2,2-pentafluoropropane and optionally one or more compounds chosen from 2,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
According to one embodiment of the invention, the composition comprises hydrogen fluoride, 3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene and optionally one or more compounds chosen from trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane.
Irrespective of the embodiment, the composition preferably comprises from 1% to 95% and advantageously from 5% to 80% by weight of hydrogen fluoride and from 99% to 5% and advantageously from 20% to 95% by weight of the sum of the organic compounds; more particularly, the composition comprises from 1% to 85% by weight of hydrogen fluoride and from 99% to 15% by weight of the sum of the organic compounds (HFO-1243zf and the (hydro)halocarbon compounds).
Irrespective of the embodiment, the boiling point of the composition according to the invention is between −20° C. and 80° C. and at a pressure between 0.1 and 44 bar absolute, preferentially between 0° C. and 40° C. and preferentially at a pressure of between 0.7 and 18 bar absolute, advantageously between 0.9 and 12.5 bar absolute.
The Applicant has discovered that the compositions according to the invention have advantageous properties in particular for the recycling of HF in the reaction step. 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, form two immiscible liquid phases.
By way of example, for the ternary compounds containing hydrogen fluoride, 3,3,3-trifluoropropene and a compound chosen from 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene and E-3,3,3-trifluoro-1-chloropropene, the appearance of a heteroazeotrope characterized by two liquid phases, one rich in HF and the other depleted in HF, depends on the amount of HF in the composition. These decantation ranges as a function of the HF content in the compositions were characterized for at least isotherms at 0° C., 25° C. and 40° C.
Similarly, the decantation ranges for the ternary compounds containing hydrogen fluoride, 3,3,3-trifluoropropene and a compound chosen from trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, Z-1,1,1,2,3-pentafluoropropene and 2-chloro-1,1,1,2-tetrafluoropropane are characterized by a phase depleted in HF and a phase enriched in HF for at least isotherms at 0° C., 25° C. and 40° C.
An azeotropic or quasi-azeotropic composition that is preferred according to the invention comprises from 1% to 85% by weight of hydrogen fluoride and from 99% to 15% by weight of the sum of HFO-1243zf and of HFC-245cb, the boiling point of this preferred composition is between 0 and 40° C. at a pressure of between 0.9 and 11.6 bar absolute.
An azeotropic or quasi-azeotropic composition that is preferred according to the invention preferably comprises from 5% to 80% by weight of hydrogen fluoride and from 95% to 20% by weight of the sum of HFO-1243zf and of HFC-245cb, the boiling point of this preferred composition is between 0 and 40° C. at a pressure of between 0.9 and 11.6 bar absolute.
An azeotropic or quasi-azeotropic composition that is preferred according to the invention preferably comprises from 1% to 85% by weight of hydrogen fluoride and from 99% to 15% by weight of the sum of HFO-1243zf, of HCFC-244bb, of HFC-245fa, of trifluoropropyne, of HFO-1225yeZ and of HFO-1225zc, the boiling point of this preferred composition is between 0 and 40° C. at a pressure of between 0.7 and 18 bar absolute.
An azeotropic or quasi-azeotropic composition that is preferred according to the invention preferably comprises from 5% to 80% by weight of hydrogen fluoride and from 95% to 20% by weight of the sum of HFO-1243zf, of HCFC-244bb, of HFC-245fa, of trifluoropropyne, of HFO-1225yeZ and of HFO-1225zc, the boiling point of this preferred composition is between 0 and 40° C. at a pressure of between 0.7 and 18 bar absolute.
The pressure characteristics of the mixtures of Examples 1, 4, 7, 10, 13, 16 and 19 were calculated for an isotherm at 25° C.
Examples 2, 5, 8, 11, 14, 17 and 20 represent the boiling point and pressure ranges of the mixtures and Examples 3, 6, 9, 12, 15, 18 and 21 represent the decantation ranges of the mixtures of Examples 1, 4, 7, 10, 13, 16 and 19 as a function of the mass percentage of HF characterized for isotherms at 0° C., 25° C. and 40° C. The decantation ranges of Examples 3, 6, 9, 12, 15, 18 and 21 are calculated for mixtures of organic compounds having equal-mass contents. By way of example, for a ternary mixture, a mixture containing 50% by weight of each of the two organic compounds is considered; for a penternary mixture, a mixture containing 25% by weight of each of the four organic compounds is considered, the mass fraction of HF ranging from 0 to 1. These calculations are performed at the liquid-vapor equilibrium, under azeotropic conditions.
HF-HFO-1243zf-HFC-245cb HF-HFO-1234yf-HFO-1243zf
HF-HCFO-1233xf-HFO-1243zf HF-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234zeE-HFO-1243zf HF-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1243zf-HFC-245cb
HF-HCFO-1233xf-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1243zf
HF-HFC-245cb-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233zdE-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233zdE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeE-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFO-1243zf-HFC-245cb
HF-HFC-245th-HFO-1234zeE-HFO-1243zf
HF-HFC-245cb-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HCFO-1233zdE-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HCFO-1233zdE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234yf-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeE-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HFO-1234zeE-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1243zf
HF-HFC-245cb-HCFO-1233zdE-HFO-1234zeE-HFO-1243zf
HF-HFC-245cb-HCFO-1233zdE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFC-245cb-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1234zeE-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234zeE-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234zeE-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HFO-1234zeE-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFC-245th-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HFO-1234yf-HFO-1234zeE-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HFC-245cb-HFO-1234zeE-HFO-1234zeZ-HCFO-1233zdE-HFO-1243zf
HF-HCFO-1233xf-HFC-245cb-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1234zeE-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HCFO-1233xf-HFO-1234yf-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFF-1243zf-HCFC-244bb-HFC-245fa-Trifluoropropyne-HFO-1225yeZ-HFO-1225zc
HF-HCFO-1233xf-HFO-1234yf-HFC-245cb-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFO-1243zf
HF-HFO-1234yf-HFC-245cb-HCFO-1233xf-HCFO-1233zdE-HFO-1234zeE-HFO-1234zeZ-HFC-1243zf-HCFC-244bb-TFP-HFC-245fa-HFO-1225yeZ-HFO-1225zc
Number | Date | Country | Kind |
---|---|---|---|
13 52486 | Mar 2013 | FR | national |
Filing Document | Filing Date | Country | Kind |
---|---|---|---|
PCT/FR2014/050371 | 2/24/2014 | WO | 00 |
Publishing Document | Publishing Date | Country | Kind |
---|---|---|---|
WO2014/147314 | 9/25/2014 | WO | A |
Number | Name | Date | Kind |
---|---|---|---|
6013846 | Wismer | Jan 2000 | A |
6328907 | Nakada et al. | Dec 2001 | B1 |
7183448 | Nakada et al. | Feb 2007 | B2 |
7423188 | Miller et al. | Sep 2008 | B2 |
8075797 | Hulse et al. | Dec 2011 | B2 |
8273928 | Knapp | Sep 2012 | B2 |
8378158 | Hulse et al. | Feb 2013 | B2 |
8450537 | Rao | May 2013 | B2 |
8858823 | Rached et al. | Oct 2014 | B2 |
9000238 | Knapp | Apr 2015 | B2 |
9889416 | Bonnet et al. | Feb 2018 | B2 |
10029961 | Deur-Bert et al. | Jul 2018 | B2 |
10029963 | Bonnet et al. | Jul 2018 | B2 |
10077221 | Bonnet et al. | Sep 2018 | B2 |
10252913 | Bonnet et al. | Apr 2019 | B2 |
10266465 | Bonnet et al. | Apr 2019 | B2 |
10343963 | Bonnet et al. | Jul 2019 | B2 |
20070100173 | Miller | May 2007 | A1 |
20070100175 | Miller | May 2007 | A1 |
20080051612 | Knapp | Feb 2008 | A1 |
20090127496 | Rao | May 2009 | A1 |
20100072415 | Rao | Mar 2010 | A1 |
20100187088 | Merkel | Jul 2010 | A1 |
20100237279 | Hulse | Sep 2010 | A1 |
20110112340 | Smith | May 2011 | A1 |
20110218369 | Elsheikh | Sep 2011 | A1 |
20110218370 | Elsheikh et al. | Sep 2011 | A1 |
20120010449 | Wismer et al. | Jan 2012 | A1 |
20120041239 | Suzuki | Feb 2012 | A1 |
20120053369 | Hulse | Mar 2012 | A1 |
20120053372 | Hulse et al. | Mar 2012 | A1 |
20120056122 | Hulse | Mar 2012 | A1 |
20120138841 | Hulse | Jun 2012 | A1 |
20120222448 | Chaki | Sep 2012 | A1 |
20120305382 | Knapp | Dec 2012 | A1 |
20130105296 | Chaki | May 2013 | A1 |
20140012052 | Pham | Jan 2014 | A1 |
20140024575 | Rached | Jan 2014 | A1 |
20150105596 | Wang | Apr 2015 | A1 |
20150197467 | Pigamo | Jul 2015 | A1 |
20160009555 | Bonnet | Jan 2016 | A1 |
20160023176 | Bonnet | Jan 2016 | A1 |
20160023974 | Bonnet | Jan 2016 | A1 |
20160031773 | Bonnet | Feb 2016 | A1 |
20160046548 | Bonnet | Feb 2016 | A1 |
20170297982 | Deur-Bert et al. | Oct 2017 | A1 |
20180126348 | Bonnet et al. | May 2018 | A1 |
20180297919 | Deur-Bert et al. | Oct 2018 | A1 |
20180312453 | Bonnet et al. | Nov 2018 | A1 |
20180354875 | Bonnet et al. | Dec 2018 | A1 |
Number | Date | Country |
---|---|---|
H11-279088 | Oct 1999 | JP |
2012-516336 | Jul 2012 | JP |
2012-521430 | Sep 2012 | JP |
WO 9727163 | Jul 1997 | WO |
WO 0029361 | May 2000 | WO |
WO 2007053736 | May 2007 | WO |
WO 2008002500 | Jan 2008 | WO |
WO 2009105517 | Aug 2009 | WO |
WO 2010059493 | May 2010 | WO |
WO 2010088196 | Aug 2010 | WO |
WO 2010088196 | Aug 2010 | WO |
WO 2010111067 | Sep 2010 | WO |
WO 2012075283 | Jun 2012 | WO |
WO 2014147310 | Sep 2014 | WO |
WO 2014147311 | Sep 2014 | WO |
WO 2014147312 | Sep 2014 | WO |
WO 2014147313 | Sep 2014 | WO |
WO 2014147314 | Sep 2014 | WO |
Entry |
---|
U.S. Appl. No. 15/104,836, Dominique Deur-Bert, filed Jun. 15, 2016. |
Deur-Bert, Dominique, U.S. Appl. No. 15/104,836 entitled “Azeotropic Compositions of Hydrogen Flouride and Z-3,3,3-Trifluoro-1-Chloropropene,”, filed Jun. 15, 2016. |
International Search Report (PCT/ISA/210) dated Jun. 10, 2014, by the France Patent Office as the International Searching Authority for International Application No. PCT/FR2014/050371. |
U.S. Appl. No. 16/018,191 Dominique Deur-Bert, Anne Pigamo and Phillipe Bonnet, filed Jun. 26, 2018. |
Duer-Bert, Dominique, U.S. Appl. No. 16/018,191 entitled “Azeotropic Compositions of Hydrogen Flouride and Z-3,3,3-Trifluoro-1-Chloropropene,” filed Jun. 26, 2018. |
U.S. Appl. No. 15/858,005, Phillippe Bonnet, Bertrand Collier, Dominique Deur-Bert and Laurent Wendlinger, filed Dec. 29, 2017. (Cited herein as U.S. Pat. No. 2018/0126348 A1 of May 10, 2018). |
Number | Date | Country | |
---|---|---|---|
20160046548 A1 | Feb 2016 | US |