阅读说明：本技术 纯化1,1,1,2,3-五氟丙烷的方法及其用于获得高纯度2,3,3,3-四氟丙烯的用途 (Process for purifying 1,1,1,2, 3-pentafluoropropane and use thereof for obtaining high purity 2,3,3, 3-tetrafluoropropene ) 是由 P-M.塞达特 C.伯特兰德 于 2019-01-04 设计创作，主要内容包括：本发明涉及一种纯化1,1,1,2,3-五氟丙烷的方法,其包括以下步骤：i)提供包含1,1,1,2,3-五氟丙烷和1,1,1,3-四氟丙烷的组合物A1；ii)在足以形成至少两种物流的条件下纯化、优选蒸馏所述组合物A1,所述至少两种物流包括包含1,1,1,2,3-五氟丙烷的第一物流和包含1,1,1,3-四氟丙烷的第二物流。本发明还涉及一种生产2,3,3,3-四氟丙烯的方法和包含2,3,3,3-四氟丙烯的组合物。(The present invention relates to a process for purifying 1,1,1,2, 3-pentafluoropropane, comprising the steps of: i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane; ii) purifying, preferably distilling, the composition A1 under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane. The invention also relates to a process for producing 2,3,3, 3-tetrafluoropropene and to compositions comprising 2,3,3, 3-tetrafluoropropene.)

1. A process for purifying 1,1,1,2, 3-pentafluoropropane, comprising the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, the composition A1 under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane.

2. The process according to the preceding claim, characterized in that the content by mass of 1,1,1,2, 3-pentafluoropropane in composition a1 is greater than 90%, advantageously greater than 92%, preferably greater than 94%, more preferably 96%, in particular greater than 98%, based on the total weight of composition a 1.

3. The method of any of the preceding claims, wherein composition a1 further comprises 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane; and step ii) of the method is: ii) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and a third stream comprising 1,1,1, 2-tetrafluoropropane.

4. The method of any of the preceding claims, wherein composition a1 further comprises 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane; and step ii) of the method is:

ii-1) distilling said composition a1 under conditions sufficient to form a stream B1 comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane and a stream B1' comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

ii-2) distilling said stream B1 'obtained in step ii-1) to form a stream B2 comprising 1,1,1,2, 3-pentafluoropropane and a stream B2' comprising 1,1,1, 3-tetrafluoropropane.

5. The process according to any one of the preceding claims, characterized in that the mass content of 1,1,1, 3-tetrafluoropropane in the first stream or in stream B2 is less than 5000ppm, advantageously less than 4000ppm, preferably less than 3000ppm, more preferably less than 2000ppm, in particular less than 1000ppm, more particularly less than 500ppm, advantageously less than 375ppm, advantageously less than 250ppm, preferably advantageously less than 100ppm, particularly advantageously less than 50ppm, more particularly advantageously less than 10ppm, based on the total weight of the first stream or in stream B2.

6. The process according to any one of the preceding claims 4 and 5, characterized in that the mass content of 1,1,1,2,3, 3-hexafluoropropane in the stream B1 'or in the stream B2 is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more particularly less than 50ppm, based on the total weight of the stream B1' or of the stream B2.

7. Process according to either of the preceding claims 4 and 6, characterized in that the mass content of 1,1,1, 2-tetrafluoropropane in the stream B1 'or in the stream B2 is less than 5000ppm, advantageously less than 4000ppm, preferably less than 3000ppm, more preferably less than 2000ppm, in particular less than 1000ppm, more particularly less than 500ppm, advantageously less than 375ppm, advantageously less than 250ppm, preferably advantageously less than 100ppm, particularly advantageously less than 50ppm, more particularly advantageously less than 10ppm, based on the total weight of the stream B1' or B2.

8. The process according to any one of the preceding claims 4 to 7, characterized in that the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the stream B1 'or in the stream B2 is less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, based on the total weight of the stream B1' or of the stream B2; more particularly, the stream B1' or the stream B2 is free of 1,1, 2-trifluoroethane, i.e. has a mass content of less than 1 ppm.

9. The process according to any one of the preceding claims, characterized in that said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is subjected to a dehydrofluorination step iii) to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

10. The process according to the preceding claim, characterized in that said stream C1 is purified under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight, advantageously at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene, based on the total weight of said stream C3.

11. The process according to the preceding claim, characterized in that stream C3 also comprises 3,3, 3-trifluoropropene and in stream C3 the mass content of 3,3, 3-trifluoropropene is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm, based on the total weight of the first stream C3.

12. The process according to any of the preceding claims 10 and 11, characterized in that stream C3 further comprises 1,2,3,3, 3-pentafluoropropene and in stream C3 the mass content of 1,2,3,3, 3-pentafluoropropene is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, based on the total weight of the first stream C3.

13. The process according to any one of the preceding claims 10 to 12, characterized in that stream C3 further comprises 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in stream C3 is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, based on the total weight of the first stream C3.

14. The process according to any one of the preceding claims, characterized in that said composition A1 is obtained by a process comprising the following steps:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") in the presence of a dehydrofluorination catalyst or using a mixture comprising water and an alkaline hydroxide to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') or b ") is gas phase hydrogenated in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition a 1.

15. The process according to the preceding claim, characterized in that the hydrogenation catalyst used in step a) and/or c) comprises between 0.001% and 1.0% by weight of palladium supported on alumina, preferably palladium supported on alumina in the alpha polymorphic form.

16. A composition comprising:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 1,1,1,2, 3-pentafluoropropane,

less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10ppm of 1,1,1, 3-tetrafluoropropane;

less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm of 1,1,1,2,3, 3-hexafluoropropane;

less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, more in particular less than 1ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane;

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 1ppm of 1,1,1, 2-tetrafluoropropane;

based on the total weight of the composition.

17. A composition comprising:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm of 3,3, 3-trifluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, of 1,2,3,3, 3-pentafluoropropene,

less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane, and

less than 20ppm, advantageously less than 15ppm, preferably less than 10ppm, in particular less than 5ppm, of 1,1,1,2, 3-pentafluoropropane,

based on the total weight of the composition.

Technical Field

The present invention relates to a process for purifying 1,1,1,2, 3-pentafluoropropane. The invention also relates to a process for the production of 2,3,3, 3-tetrafluoropropene from purified 1,1,1,2, 3-pentafluoropropane. Finally, the present invention relates to the production of high purity 2,3,3, 3-tetrafluoropropene.

Background

Hydrofluorocarbons (HFCs) and in particular hydrofluoroolefins such as 2,3,3, 3-tetrafluoro-1-propene (HFO1234yf) are compounds that are well known for their properties as refrigerants and heat transfer fluids, fire extinguishing agents, propellants, blowing agents, swelling agents, dielectric gases, polymerization media or monomers, support fluids, abrasives, desiccants, and fluids for power generation equipment. Unlike CFCs and HCFCs, which are potentially dangerous to the ozone layer, HFOs do not contain any chlorine and thus do not cause any problems to the ozone layer.

Several methods of making 1234yf are known.

WO2011/010025 describes a process for the preparation of 2,3,3, 3-tetrafluoro-1-propene comprising the steps of: (I) gas phase hydrogenation of hexafluoropropene in a reactor to 1,1,1,2,3, 3-hexafluoropropane in the presence of a super stoichiometric amount of hydrogen and a catalyst; (ii) dehydrofluorinating the 1,1,1,2,3, 3-hexafluoropropane obtained in the previous step in the presence of a dehydrofluorination catalyst or using a mixture of water and potassium hydroxide to obtain 1,2,3,3, 3-pentafluoro-1-propene; (iii) gas-phase hydrogenating the 1,2,3,3, 3-pentafluoro-1-propene obtained in the preceding step in a reactor in the presence of a super-stoichiometric amount of hydrogen and a catalyst to obtain 1,1,1,2, 3-pentafluoropropane; (iv) purifying the 1,1,1,2, 3-pentafluoropropane obtained in the previous step; (v) dehydrofluorinating the purified 1,1,1,2, 3-pentafluoropropane in the presence of a dehydrofluorination catalyst or using a mixture of water and potassium hydroxide to obtain 2,3,3, 3-tetrafluoro-1-propene; (vi) purifying the 2,3,3, 3-tetrafluoro-1-propene obtained in the previous step.

WO 2010/139873 describes a dehydrofluorination process in the presence of a solid reagent comprising calcium hydroxide.

WO 2008/030439 describes a process for the preparation of hydrofluoroolefins from fluoropropane compounds in the presence of a basic solution, a solvent and a phase transfer agent.

WO 03/027051 describes a process for the preparation of hydrofluoroolefins from fluoropropane compounds in the presence of an alkaline hydroxide and a phase transfer agent.

CN103449963 describes a multi-step process for the preparation of 2,3,3, 3-tetrafluoropropene, which comprises in particular a dehydrofluorination step in the presence of a basic solution and an organic solvent. US 2010/0029997 describes a process for the production of 2,3,3, 3-tetrafluoropropene. Obtained from 1,1,1,2, 3-pentafluoropropane purified by photochlorination to remove certain impurities prior to carrying out the dehydrofluorination reaction.

There is a need for a method of preparing HFO-1234yf that makes it possible to limit the content of by-products produced in the various steps of the method of manufacturing HFO-1234yf, in particular impurities having potential toxicity: mention may be made of 1,2,3,3, 3-pentafluoropropene (1225ye), 1,2, 2-trifluoroethane (143) and 3,3, 3-trifluoropropene (1243 zf). 1,2,3,3, 3-pentafluoropropene (1225ye) has a boiling point close to HFO-1234yf and is difficult to separate from HFO1234 yf. The boiling point of 3,3, 3-trifluoropropene is close to that of HFO-1234yf and is very difficult to separate from HFO-1234 yf. These separations require very harsh conditions, which are often expensive. US 2013/0317262 discloses, inter alia, a process for purifying 2,3,3, 3-tetrafluoropropene by extractive distillation to remove 3,3, 3-trifluoropropene.

Accordingly, the present invention provides a simple and inexpensive method for producing high purity HFO-1234yf that does not suffer from the above-described disadvantages.

Disclosure of Invention

According to a first aspect, the present invention relates to a process for purifying 1,1,1,2, 3-pentafluoropropane, comprising the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, the composition A1 under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane.

According to a preferred embodiment, the content by mass of 1,1,1,2, 3-pentafluoropropane in the composition a1 is greater than 90%, advantageously greater than 92%, preferably greater than 94%, more preferably 96%, in particular greater than 98%, based on the total weight of the composition a 1.

According to a preferred embodiment, said composition a1 further comprises 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane; and step ii) of the method is: ii) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and a third stream comprising 1,1,1, 2-tetrafluoropropane.

According to a preferred embodiment, said composition a1 further comprises 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane; and step ii) of the method is:

ii-1) distilling said composition a1 under conditions sufficient to form a stream B1 comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane and a stream B1' comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

ii-2) distilling said stream B1 'obtained in step ii-1) to form a stream B2 comprising 1,1,1,2, 3-pentafluoropropane and a stream B2' comprising 1,1,1, 3-tetrafluoropropane.

Said stream B1 corresponds to said third stream comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane. Said stream B2 corresponds to said first stream comprising 1,1,1,2, 3-pentafluoropropane. Said stream B2' corresponds to said second stream comprising 1,1,1, 3-tetrafluoropropane.

According to a preferred embodiment, the mass content of 1,1,1, 3-tetrafluoropropane in said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is less than 5000ppm, advantageously less than 4000ppm, preferably less than 3000ppm, more preferably less than 2000ppm, in particular less than 1000ppm, more particularly less than 500ppm, advantageously less than 375ppm, advantageously less than 250ppm, preferably advantageously less than 100ppm, particularly advantageously less than 50ppm, more particularly advantageously less than 10ppm, based on the total weight of said first stream or said stream B2.

According to a preferred embodiment, the mass content of 1,1,1,2,3, 3-hexafluoropropane in the stream B1 'or in the stream B2 is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm, based on the total weight of the stream B1' or the stream B2.

According to a preferred embodiment, the mass content of 1,1,1, 2-tetrafluoropropane in the stream B1 'or in the stream B2 is less than 5000ppm, advantageously less than 4000ppm, preferably less than 3000ppm, more preferably less than 2000ppm, in particular less than 1000ppm, more particularly less than 500ppm, advantageously less than 375ppm, advantageously less than 250ppm, preferably advantageously less than 100ppm, particularly advantageously less than 50ppm, more particularly advantageously less than 10ppm, based on the total weight of the stream B1' or B2.

According to a preferred embodiment, the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the stream B1 'or in the stream B2 is less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, based on the total weight of the stream B1' or of the stream B2; more particularly, the stream B1' or the stream B2 is free of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane, i.e. has a mass content of less than 1 ppm.

According to a preferred embodiment, said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is subjected to a dehydrofluorination step iii) to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

According to a preferred embodiment, the stream C1 is purified under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight, advantageously at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene, based on the total weight of the stream C3.

According to a preferred embodiment, stream C3 further comprises 3,3, 3-trifluoropropene and the mass content of 3,3, 3-trifluoropropene in stream C3 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm, based on the total weight of the first stream C3.

According to a preferred embodiment, stream C3 also comprises 1,2,3,3, 3-pentafluoropropene and the mass content of 1,2,3,3, 3-pentafluoropropene in stream C3 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, based on the total weight of the first stream C3.

According to a preferred embodiment, stream C3 also comprises 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in stream C3 is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, based on the total weight of the first stream C3.

According to a preferred embodiment, said composition a1 is obtained by a process comprising the following steps:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating the stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') or b ") is gas phase hydrogenated in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition a 1.

According to a preferred embodiment, the hydrogenation catalyst used in step a) and/or c) comprises between 0.001 and 1.0% by weight of palladium supported on alumina, preferably palladium supported on alumina in the alpha polymorphic form.

According to another aspect, the present invention provides a composition comprising:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 1,1,1,2, 3-pentafluoropropane,

less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10ppm of 1,1,1, 3-tetrafluoropropane;

less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm of 1,1,1,2,3, 3-hexafluoropropane;

less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, more in particular less than 1ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane;

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 1ppm of 1,1,1, 2-tetrafluoropropane;

based on the total weight of the composition.

According to another aspect, the present invention provides a composition comprising:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm of 3,3, 3-trifluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, of 1,2,3,3, 3-pentafluoropropene,

less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane, and

less than 20ppm, advantageously less than 15ppm, preferably less than 10ppm, in particular less than 5ppm, of 1,1,1,2, 3-pentafluoropropane,

based on the total weight of the composition.

Drawings

Fig. 1a and 1b schematically show a process for purifying 1,1,1,2, 3-pentafluoropropane and producing 2,3,3, 3-tetrafluoropropene according to a particular embodiment of the present invention.

Fig. 2a and 2b schematically illustrate a process for producing 2,3,3, 3-tetrafluoropropene from hexafluoropropylene according to a particular embodiment of the present invention.

Figures 3a, 3b, 4a and 4b schematically illustrate a process for the production of 2,3,3, 3-tetrafluoropropene from hexafluoropropene according to a particular embodiment of the present invention, comprising the purification of 1,2,3,3, 3-tetrafluoropropene and 1,1,1,2, 3-pentafluoropropane.

Detailed Description

According to a first aspect, the present invention relates to a process for purifying 1,1,1,2, 3-pentafluoropropane. Preferably, the purification method comprises the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, the composition A1 under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane.

The purification according to step ii) of the invention makes it possible in particular to separate 1,1,1,2, 3-pentafluoropropane from all or some of the compounds having a boiling point which is greater than that of 1,1,1,2, 3-pentafluoropropane, preferably a boiling point which is at least 5 ℃ greater than that of 1,1,1,2, 3-pentafluoropropane.

According to a preferred embodiment, said composition a1 further comprises 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane; and step ii) of the method is:

ii) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and a third stream comprising 1,1,1, 2-tetrafluoropropane.

Thus, according to a preferred embodiment, the present invention may relate to a process for purifying 1,1,1,2, 3-pentafluoropropane, comprising the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and a third stream comprising 1,1,1, 2-tetrafluoropropane.

According to a particular embodiment, the purification of the composition a1 can be carried out in a single step using a dividing-wall distillation column.

According to another particular embodiment, the purification of the composition a1 can be carried out by carrying out two successive distillation steps using, for example, two distillation columns. Thus, according to a particular embodiment, the present invention may relate to a process for purifying 1,1,1,2, 3-pentafluoropropane, comprising the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane;

i') optionally drying said composition a 1;

ii-1) distilling said composition a1 under conditions sufficient to form a stream B1 comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane and a stream B1' comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

ii-2) distilling said stream B1 'obtained in step ii-1) to form a stream B2 comprising 1,1,1,2, 3-pentafluoropropane and a stream B2' comprising 1,1,1, 3-tetrafluoropropane.

Said stream B2 may correspond to said first stream comprising 1,1,1,2, 3-pentafluoropropane as described above. Said stream B2' may correspond to said second stream comprising 1,1,1, 3-tetrafluoropropane as described above. Said stream B1 may correspond to said third stream comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane as described above.

Preferably, the drying of composition a1 may be performed by contacting the composition a1 with a solid absorbent. The solid absorbent may comprise an agent that absorbs acidic molecules and/or a water-absorbing agent. The water absorbing agent may be an inorganic salt such as magnesium sulfate, calcium chloride, or may be a molecular sieve of type 3A, 4A, 5A, AW500, XH-7, XH-9, or 13X, silica gel, activated carbon, or a mixture thereof. The agent that absorbs acidic molecules may be: metal oxides such as aluminum oxide, alkaline earth metal oxides, alkali metal oxides or metal hydroxides such as aluminum hydroxide, alkaline earth metal hydroxides, alkali metal hydroxides, aluminosilicates such as andalusite, kyanite, sillimanite, calcium aluminosilicate, sodium aluminosilicate, or silica or mixtures thereof. When the drying step is carried out in the presence of a water-absorbing agent and an agent which absorbs acidic molecules, it is preferable to contact the composition a1 with the agent which absorbs acidic molecules and then with the water-absorbing agent. The agent that absorbs acidic molecules preferably absorbs hydrofluoric acid.

Preferably, step ii-1) is carried out at a pressure of between 1 and 20bar absolute, advantageously between 1 and 15bar absolute, preferably between 5 and 10bar absolute.

Preferably, in step ii-1), said stream B1 is recovered at the top of the distillation column. The stream B1' is recovered at the bottom of the distillation column. Preferably, the temperature at the top of the distillation column is between 20 ℃ and 100 ℃, and preferably between 45 ℃ and 75 ℃.

Preferably, step ii-2) is carried out at a pressure of between 1 and 20bar absolute, advantageously between 1 and 10bar absolute, preferably between 3 and 6bar absolute.

Preferably, in step ii-2), said stream B2 is recovered at the top of the distillation column. The stream B2' is recovered at the bottom of the distillation column. Preferably, the temperature at the top of the distillation column is between 40 ℃ and 100 ℃, and preferably between 50 ℃ and 80 ℃.

According to a preferred embodiment, the content by mass of 1,1,1,2, 3-pentafluoropropane in the composition a1 is greater than 80%, advantageously greater than 90%, preferably greater than 92%, more preferably greater than 94%, in particular greater than 96%, more in particular greater than 98%, based on the total weight of the composition a 1.

The mass content of 1,1,1, 3-tetrafluoropropane in the composition a1 and/or in the stream B1 'may be less than 5%, advantageously less than 4%, preferably less than 3%, more preferably less than 2%, in particular less than 1%, more in particular less than 0.5%, based on the total weight of the composition a1 and/or of the stream B1'.

Preferably, the mass content of 1,1,1, 3-tetrafluoropropane in the composition a1 and/or in the stream B1' is less than 3000ppm, based on the total weight of the composition a1 and/or of the stream B1', advantageously less than 2500ppm, preferably less than 2000ppm, in particular less than 1500ppm, more particularly less than 1000ppm, based on the total weight of the composition a1 and/or of the stream B1 '.

According to a preferred embodiment, said stream a1 may also comprise 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane, as described above.

Thus, when it is contained, the mass content of 1,1,1,2,3, 3-hexafluoropropane in the composition a1 may be less than 1000ppm, based on the total weight of the composition a1, advantageously less than 750ppm, preferably less than 500ppm, in particular less than 375ppm, more in particular less than 250 ppm. The mass content of 1,1,1,2,3, 3-hexafluoropropane in the composition a1 may be greater than 20ppm, advantageously greater than 30ppm, in particular greater than 60 ppm.

When included, the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the composition a1 may be less than 5%, based on the total weight of the composition a1, advantageously less than 4%, preferably less than 3%, in particular less than 2%, more in particular less than 1%.

When included, the mass content of 1,1,1, 2-tetrafluoropropane in the composition a1 may be less than 15%, based on the total weight of the composition a1, advantageously less than 10%, preferably less than 5%, in particular less than 2%, more in particular less than 1%.

The steps ii) or ii-1) and ii-2) of purifying the composition a1 according to the present purification process enable the production of the first stream comprising 1,1,1,2, 3-pentafluoropropane or the stream B2 having a purity greater than that of the composition a 1. Therefore, the mass content of 1,1,1, 3-tetrafluoropropane in said composition a1 is preferably greater than the mass content obtained in said first stream or in said stream B2 after carrying out steps ii) or ii-1) and ii-2).

Preferably, the mass content of 1,1,1,2, 3-pentafluoropropane in said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is at least 99.5 wt%, advantageously at least 99.8 wt%, based on the total weight of said first stream or said stream B2.

Advantageously, the mass content of 1,1,1, 3-tetrafluoropropane in said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10ppm, based on the total weight of said first stream or said stream B2.

Preferably, the mass content of 1,1,1,2,3, 3-hexafluoropropane in said stream B1 'or said stream B2, when it is contained, is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm, based on the total weight of said stream B1' or said stream B2.

Preferably, when it is contained, the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in said stream B1 'or in said stream B2 is less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, based on the total weight of said stream B1' or of said stream B2; more particularly, the stream B1' or the stream B2 is free of 1,1, 2-trifluoroethane, i.e. has a mass content of less than 1 ppm.

Preferably, when it is contained, the mass content of 1,1,1, 2-tetrafluoropropane in the stream B1 'or in the stream B2 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, based on the total weight of the stream B1' or of the stream B2; more particularly, the stream B1' or the stream B2 is free of 1,1,1, 2-tetrafluoropropane, i.e. has a mass content of less than 1 ppm.

Streams a1, B1' and/or B2 may also comprise 1,2,3,3, 3-pentafluoropropene. Preferably, the mass content of 1,2,3,3, 3-pentafluoropropene in said stream B1 'or in said stream B2, when present, is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 50ppm, in particular less than 10ppm, based on the total weight of said stream B1' or said stream B2. Preferably, the mass content of 1,2,3,3, 3-pentafluoropropene in stream a1 is less than 10%, advantageously less than 5%, preferably less than 1%, more preferably less than 5000ppm, especially less than 2000ppm, based on the total weight of stream a 1.

Stream a1, B1' and/or B2 may also comprise Hydrogen Fluoride (HF). Preferably, the mass content of HF in said stream B1 'or in said stream B2, when it is contained, is less than 2000ppm, advantageously less than 1500ppm, preferably less than 1000ppm, more preferably less than 500ppm, in particular less than 100ppm, based on the total weight of said stream B1' or of said stream B2. Preferably, the mass content of HF in the stream a1 is less than 1%, advantageously less than 7500ppm, preferably less than 5000ppm, more preferably less than 2500ppm, based on the total weight of the stream a 1.

The streams A1, B1' and/or B2 may also comprise water (H)₂O). When it is contained, inThe mass content of water in the stream B1 'or the stream B2 is less than 1000ppm, preferably less than 750ppm, more preferably less than 500ppm, in particular less than 250ppm, based on the total weight of the stream B1' or the stream B2. When it is contained, the water content by mass in the stream a1 is less than 10000ppm, advantageously less than 5000ppm, preferably less than 2500ppm, based on the total weight of the stream a 1.

Said second stream or said stream B2' obtained at the bottom of the distillation column during step ii) or ii-2) may be recovered for subsequent upgrading (upgrading) or may be emptied into incineration plants. In addition, the stream B1 obtained in step ii-1) or the third stream obtained in step ii) may be recovered for subsequent upgrading or may be discharged to an incineration plant.

The present purification process enables the removal of precursors of impurities that are difficult to separate from 2,3,3, 3-tetrafluoropropene upstream of the reaction that forms the impurities. For example, 3,3, 3-trifluoropropene is difficult to separate from 2,3,3, 3-tetrafluoropropene. Applicants have determined that 3,3, 3-trifluoropropene may be formed from precursors of, for example, 1,1,1, 3-tetrafluoropropane and/or 1,1,1, 2-tetrafluoropropane. Thus, by the present purification process, a stream of 1,1,1,2, 3-pentafluoropropane is obtained in which the content of 1,1,1, 3-tetrafluoropropane is reduced. According to a particular embodiment of the present purification process, a stream of 1,1,1,2, 3-pentafluoropropane is obtained in which the content of 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane is reduced. This makes it possible to reduce impurities such as 1,2,3,3, 3-pentafluoropropene or 3,3, 3-trifluoropropene in 2,3,3, 3-tetrafluoropropene.

According to a preferred embodiment, said first stream comprising 1,1,1,2, 3-pentafluoropropane or said stream B2 is subjected to a dehydrofluorination step iii) to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

Thus, according to a second aspect of the present invention, there is provided a process for producing 2,3,3, 3-tetrafluoropropene. The process for producing 2,3,3, 3-tetrafluoropropene includes the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, the composition a1 under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane;

iii) dehydrofluorinating said first stream comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

According to a preferred embodiment, the process for producing 2,3,3, 3-tetrafluoropropene comprises the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane;

i') optionally drying said composition a 1;

ii) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and a third stream comprising 1,1,1, 2-tetrafluoropropane;

iii) dehydrofluorinating said first stream comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

According to a particular embodiment, the process for the production of 2,3,3, 3-tetrafluoropropene comprises the steps of:

i) providing a composition a1 comprising 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane;

i') optionally drying said composition a 1;

ii-1) distilling said composition a1 under conditions sufficient to form a stream B1 comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane and a stream B1' comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

ii-2) distilling said stream B1 'obtained in step ii-1) to form a stream B2 comprising 1,1,1,2, 3-pentafluoropropane and a stream B2' comprising 1,1,1, 3-tetrafluoropropane;

iii) dehydrofluorinating said stream B2 comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene.

The dehydrofluorination step can be carried out according to techniques known to those skilled in the art, as described, for example, in WO2011/010025, page 10, lines 1-21 and page 14, lines 19 to page 15, line 4, which is incorporated herein by reference. For example, potassium hydroxide is preferably present in the reaction medium in an amount of between 20% and 75% by weight, and advantageously between 55% and 70% by weight, relative to the weight of the mixture of water and KOH. For example, the aqueous reaction medium of the dehydrofluorination step comprising KOH is preferably maintained at a temperature of between 80 and 180 ℃, advantageously between 125 and 180 ℃.

In addition to 2,3,3, 3-tetrafluoropropene, the stream C1 may also comprise one or more compounds selected from the following: 3,3, 3-trifluoropropene, 1,2,3,3, 3-pentafluoropropene, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1, 2-difluoroethylene and 1, 1-difluoroethylene. These compounds may originate from side reactions which occur during step iii) according to the invention, possibly due to the presence of residual impurities other than 1,1,1, 3-tetrafluoropropane in composition a1 or in said first stream or in said stream B2.

Preferably, the mass content of 3,3, 3-trifluoropropene in said stream C1 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, based on the total weight of said stream C1. This content of 3,3, 3-trifluoropropene in said stream C1 can be obtained by: carrying out step ii) or steps ii-1) and ii-2), purifying, preferably distilling, said composition a1, comprising in particular 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane. The separation between 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane (step iii) of the present process) prior to the dehydrofluorination of 1,1,1,2, 3-pentafluoropropane makes it possible to finally obtain a high purity stream C1 which is practically free of 3,3, 3-trifluoropropene. Prior to the dehydrofluorination of 1,1,1,2, 3-pentafluoropropane, the separation between 1,1,1,2, 3-pentafluoropropane on the one hand and 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane on the other hand (if the latter compound is present in said composition a1) (step iii) of the process) makes it possible to finally obtain a high purity stream C1 which is practically free of 1,2,3,3, 3-pentafluoropropene and/or 3,3, 3-trifluoropropene.

According to a preferred embodiment, the stream C1 is purified under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight, preferably at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene, based on the total weight of the stream C3.

The stream C1 can thus be purified by one or more steps including, for example, condensation, evaporation, decantation, absorption, washing, liquid-liquid extraction, photochlorination, distillation, for example extractive distillation, azeotropic distillation, adsorption on solids and more particularly on molecular sieves, alumina or activated carbon, and membrane separation. The purification of the stream C1 may comprise at least one adsorption step, preferably on activated alumina and/or molecular sieves, and at least one distillation step.

Thus, the process of the present invention for the production of 2,3,3, 3-tetrafluoropropene may comprise a step iv) of purifying the stream C1 obtained in step iii) to form said stream C3.

In particular, said step iv) of purifying said stream C1 comprises a first distillation separating 2,3,3, 3-tetrafluoropropene from light impurities and a second distillation separating 2,3,3, 3-tetrafluoropropene from heavy impurities, in particular 1,1,1,2, 3-pentafluoropropane.

In particular, the process for producing 2,3,3, 3-tetrafluoropropene of the present invention may include the steps of:

iv-1) purifying, preferably distilling, said stream C1 obtained in step iii) to form a stream C2, preferably at the top of the distillation column, and a stream C2', preferably at the bottom of the distillation column, comprising 2,3,3, 3-tetrafluoropropene;

iv-2) purifying, preferably distilling, said stream C2 'obtained in step iv-1) to form said stream C3, preferably at the top of a distillation column, comprising 2,3,3, 3-tetrafluoropropene, and stream C3', preferably at the bottom of a distillation column, comprising 1,1,1,2, 3-pentafluoropropane.

Said step iv-1) can be carried out at a pressure of from 2 to 20bar absolute, advantageously from 11 to 15bar absolute. Preferably, the temperature at the top of the distillation column is from 35 ℃ to 50 ℃. Stream C2 may contain, inter alia, 1-difluoroethylene.

Said step iv-2) can be carried out at a pressure of from 2 to 20bar absolute, advantageously from 9 to 13bar absolute. Preferably, the temperature at the top of the distillation column is from 36 ℃ to 51 ℃.

Preferably, the stream C3' can be recycled to step iii) or step i).

Preferably, the mass content of 1,2,3,3, 3-pentafluoropropene in said stream C1 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, in particular less than 25ppm, based on the total weight of said stream C1.

Preferably, the mass content of 1,1,1,2, 3-pentafluoropropene in stream C1 or in stream C2 'is less than 40%, advantageously less than 30%, preferably less than 20%, in particular less than 10%, based on the total weight of stream C1 or stream C2'.

Preferably, the mass content of 1, 2-difluoroethylene in the stream C2 'and/or in the stream C3 is less than 500ppm, advantageously less than 250ppm, preferably less than 100ppm, in particular less than 50ppm, based on the total weight of the stream C2' or the stream C3.

As mentioned above, the purification of said stream C1 makes it possible to produce a stream C3 comprising purified 2,3,3, 3-tetrafluoropropene.

Preferably, the mass content of 3,3, 3-trifluoropropene in stream C3 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm, based on the total weight of said stream C3.

Preferably, the mass content of 1,2,3,3, 3-pentafluoropropene in stream C3 is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, based on the total weight of stream C3.

According to a preferred embodiment, stream C3 also comprises 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in stream C3 is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, based on the total weight of the first stream C3.

Preferably, the mass content of 1,1,1,2, 3-pentafluoropropane in the stream C3 is less than 10ppm, advantageously less than 5ppm, based on the total weight of the stream C3; preferably, the stream C3 is free of 1,1,1,2, 3-pentafluoropropane, i.e. has a mass content of less than 1 ppm.

According to a preferred embodiment, said composition a1 is obtained by a process comprising the following steps:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating the stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') or b ") is gas phase hydrogenated in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition a 1.

Preferably, the hydrogenation step a) and/or c) is carried out in the presence of a catalyst. Catalysts which may be mentioned in particular include metals such as Pd, Ru, Pt, Rh, Ir, Fe, Co, Ni, Cu, Ag, Re, Os, Au, Ge, Te, which are optionallyLoaded. Vectors which may be mentioned in particular include: carbon, alumina, fluorided alumina, AlF₃The amount of metal present in the catalyst when it is supported may be between 0.001 and 10 wt%, preferably between 0.001 and 1.0 wt%, in particular between 0.01 and 0.2 wt% the hydrogenation step is advantageously carried out in the presence of Pd supported on alumina, preferably Pd supported on α polymorphic form of alumina, in particular the hydrogenation catalyst may comprise Pd supported on α polymorphic form of alumina, and palladium represents from 0.001 to 1.0 wt%, preferably from 0.01 to 0.2 wt% of the total weight of the catalyst the hydrogenation step may be carried out in liquid phase or in vapour phase, however, the vapour phase is preferred.

The hydrogenation step a) is carried out in the presence of hydrogen, advantageously with a hydrogen/hexafluoropropylene molar ratio between 1 and 50, and most particularly between 2 and 15. The hydrogenation step c) is carried out in the presence of hydrogen, advantageously with a hydrogen/1, 2,3,3, 3-pentafluoropropene molar ratio of between 1 and 50, and most particularly between 2 and 15.

The hydrogenation step a) and/or c) is preferably carried out at a temperature between 50 and 200 ℃, preferably between 80 and 120 ℃. Preferably, the temperature at the inlet of the reactor of the hydrogenation step a) and/or c) is between 30 and 100 ℃, advantageously between 40 and 80 ℃.

The contact time of the hydrogenation steps a) and/or c) (defined as the ratio of the volume of the catalytic bed to the volumetric flow rate of the total stream under the usual conditions of temperature and pressure) is preferably between 0.1s and 20s, and advantageously between 0.5 and 5 s.

The hydrogenation steps a) and/or c) are preferably carried out at an absolute pressure of between 0.5 and 20bar and advantageously between 1 and 5 bar.

Preferably, the hydrogenation steps a) and/or c) are carried out in the presence of a diluent which can be introduced into the reaction medium together with the reagents. The diluent is an inert gas which does not react under the conditions of the hydrogenation step. Nitrogen, helium or argon may be mentioned as diluents. The molar ratio of diluent/reagent at the inlet of the reactor of the hydrogenation step a) and/or c) may be between 100:1 and 1:1, preferably between 10:1 and 1:1, advantageously between 5:1 and 1: 1.

In particular, during step a) according to the invention, the diluent can be the hydrogenation product HFC-236 ea. In this case, a portion of the gaseous effluent obtained from the reactor comprising HFC-236ea, unreacted hydrogen and optionally unreacted hexafluoropropene, 1,1,1,2, 3-pentafluoropropane (HFC-245eb) and 1,1,1, 2-tetrafluoropropane (HFC-254eb) is recycled and another portion of the gaseous effluent obtained from the reactor is subjected to a separation and/or purification step. The gas stream comprising the recycle loop and the reagents may be preheated prior to introduction into the reactor. The portion of gaseous effluent recycled to the reactor preferably represents at least 90% by volume, advantageously at least 93% by volume, of the total amount of effluent at the outlet of the reactor. Particularly preferably, the portion of the effluent recycled to the reactor represents 94% to 98% by volume of the total effluent at the outlet of the reactor.

The stream at the end of hydrogenation step a) may be subjected to a condensation step, provided that the unreacted hydrogen is not condensed and that a portion of the HFC-236a formed in step a) is condensed. Preferably, the condensation step is carried out at a temperature between 0 and 50 ℃ and at a pressure between 0.5 and 20bar absolute, advantageously between 1 and 5bar absolute. Preferably, the condensation step is carried out under conditions such that 1% to 30% and advantageously 2% to 10% of HFC-236ea leaving the reactor is condensed. The uncondensed fraction is then recycled, after optional heating, to the hydrogenation step a). The condensed fraction is then evaporated and then sent to step b). The condensed fraction may be purified and/or dried before step b) is performed.

If so, step a') of drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane may be carried out by contacting said stream with a solid absorbent. The solid absorbent may comprise an agent that absorbs acidic molecules and/or a water-absorbing agent. The water absorbing agent may be an inorganic salt such as magnesium sulfate, calcium chloride, or may be a molecular sieve of type 3A, 4A, 5A, AW500, XH-7, XH-9, or 13X, silica gel, activated carbon, or a mixture thereof. The agent that absorbs acidic molecules may be: metal oxides such as aluminum oxide, alkaline earth metal oxides, alkali metal oxides or metal hydroxides such as aluminum hydroxide, alkaline earth metal hydroxides, alkali metal hydroxides, aluminosilicates such as andalusite, kyanite, sillimanite, calcium aluminosilicate, sodium aluminosilicate, or silica or mixtures thereof. When the drying step is carried out in the presence of a water-absorbing agent and an agent which absorbs acidic molecules, the stream is preferably contacted with the agent which absorbs acidic molecules and then with the water-absorbing agent. The agent that absorbs acidic molecules preferably absorbs hydrofluoric acid.

If carried out, step a ") of purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a') enables the removal of the by-products formed during step a) to recover a stream comprising purified 1,1,1,2,3, 3-hexafluoropropane, i.e. wherein the content of by-products is reduced.

Step b) of the dehydrofluorination of 1,1,1,2,3, 3-hexafluoropropane is carried out under the conditions described above in connection with step iii) of the process. Step b) of the process enables the production of a stream comprising 1,2,3,3, 3-pentafluoropropene. This product may optionally be purified or not purified before being subjected to hydrogenation step c) described above.

According to the process of the invention, preferably one or more adiabatic reactors are used.

Thus, according to a particular aspect of the present invention, a process for the production of 2,3,3, 3-tetrafluoropropene comprises the steps of:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating the stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) gas-phase hydrogenating the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition a1 comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

d) purifying, preferably distilling, the composition a1 obtained in step c) under conditions sufficient to form at least two streams comprising a first stream comprising 1,1,1,2, 3-pentafluoropropane and a second stream comprising 1,1,1, 3-tetrafluoropropane;

e) dehydrofluorinating said first stream comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene;

e') optionally drying said stream C1 obtained from step e);

e ') optionally, purifying, preferably distilling, said stream C1 obtained from step e) or e') under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight of 2,3,3, 3-tetrafluoropropene, based on the total weight of said stream C3.

Preferably, the process for producing 2,3,3, 3-tetrafluoropropene comprises the steps of:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating the stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) gas-phase hydrogenating the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition A1 comprising 1,1,1,2,3, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane;

d) purifying, preferably distilling, said composition a1 under conditions sufficient to form a first stream comprising 1,1,1,2, 3-pentafluoropropane, a second stream comprising 1,1,1,3, 3-tetrafluoropropane, and a third stream comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane, and 1,1,1, 2-tetrafluoropropane;

e) dehydrofluorinating said first stream comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene;

e') optionally drying said stream C1 obtained from step e);

e ') optionally, purifying, preferably distilling, said stream C1 obtained from step e) or e') under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight of 2,3,3, 3-tetrafluoropropene, based on the total weight of said stream C3.

In particular, the process for producing 2,3,3, 3-tetrafluoropropene comprises the steps of:

a) hydrogenating hexafluoropropene in the gas phase in the presence of hydrogen and a hydrogenation catalyst to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a') optionally, drying said stream comprising 1,1,1,2,3, 3-hexafluoropropane;

a ") optionally, purifying, preferably distilling, said stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained from step a) or a');

b) dehydrofluorinating the stream comprising 1,1,1,2,3, 3-hexafluoropropane obtained in step a) or a') or a ") to form a stream comprising 1,2,3,3, 3-pentafluoropropene;

b') optionally, drying said stream comprising 1,2,3,3, 3-pentafluoropropene;

b ") optionally, purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene obtained from step b) or b');

c) gas-phase hydrogenating the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b') in the presence of hydrogen and a hydrogenation catalyst under conditions sufficient to form said composition A1 comprising 1,1,1,2,3, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane;

d-1) distilling said composition a1 under conditions sufficient to form a stream B1 comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane and a stream B1' comprising 1,1,1,2, 3-pentafluoropropane and 1,1,1, 3-tetrafluoropropane;

d-2) distilling said stream B1 'obtained in step ii-1) to form a stream B2 comprising 1,1,1,2, 3-pentafluoropropane and a stream B2' comprising 1,1,1, 3-tetrafluoropropane;

e) dehydrofluorinating said stream B2 comprising 1,1,1,2, 3-pentafluoropropane to form a stream C1 comprising 2,3,3, 3-tetrafluoropropene;

e') optionally drying said stream C1 obtained from step e);

e ') optionally, purifying, preferably distilling, said stream C1 obtained from step e) or e') under conditions sufficient to obtain a stream C3 comprising at least 99.5% by weight of 2,3,3, 3-tetrafluoropropene, based on the total weight of said stream C3.

The above-mentioned step d), step d-1), step d-2) and step e) correspond to the above-mentioned step ii), step ii-1), step ii-2) and step iii) of the process for purifying 1,1,1,2, 3-pentafluoropropane and the process for producing 2,3,3, 3-tetrafluoropropene, respectively, in the present application.

Step b ") may be carried out to purify the 1,2,3,3, 3-pentafluoropropene obtained in step b) or b'). The stream comprising 1,2,3,3, 3-pentafluoropropene formed in step b) or b') may comprise, inter alia, 1,1,1,2,3, 3-hexafluoropropane and 1,1, 2-trifluoroethylene. Thus, step b ") may comprise a step of purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene to form a stream D1 comprising 1,2,3,3, 3-pentafluoropropene and 1,1, 2-trifluoroethylene, advantageously at the top of the distillation column; and a stream D2 comprising 1,1,1,2,3, 3-hexafluoropropane, advantageously at the bottom of the distillation column.

Alternatively, step b ") may comprise a step of purifying, preferably distilling, said stream comprising 1,2,3,3, 3-pentafluoropropene to form and recover a stream D3 comprising 1,1, 2-trifluoroethylene, advantageously at the top of the distillation column, and a stream D3' comprising 1,2,3,3, 3-pentafluoropropene and 1,1,1,2,3, 3-hexafluoropropane, advantageously at the bottom of the distillation column. The distillation may be carried out at a pressure of from 11 to 15bara and the temperature at the top of the distillation column is from 45 ℃ to 65 ℃. Said stream D3 'may be distilled to form and recover a stream D4 comprising 1,2,3,3, 3-pentafluoropropene, advantageously at the top of the distillation column, and a stream D4' comprising 1,1,1,2,3, 3-hexafluoropropane, advantageously at the bottom of the distillation column. The distillation may be carried out at a pressure of from 9 to 13bara and the temperature at the top of the distillation column is from 44 ℃ to 60 ℃.

The stream D1 or D4 can be used in step c) of the process. The stream D4' comprising 1,1,1,2,3, 3-hexafluoropropane can be recycled to step b). Stream D3 may be upgraded or incinerated.

According to another aspect of the present invention, a composition is provided. Preferably, the composition comprises:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 1,1,1,2, 3-pentafluoropropane,

less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10ppm of 1,1,1, 3-tetrafluoropropane;

less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm of 1,1,1,2,3, 3-hexafluoropropane;

less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, more in particular less than 1ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane;

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 1ppm of 1,1,1, 2-tetrafluoropropane;

optionally less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 50ppm, in particular less than 10ppm, of 1,2,3,3, 3-pentafluoropropene;

optionally less than 2000ppm, advantageously less than 1500ppm, preferably less than 1000ppm, more preferably less than 500ppm, in particular less than 100ppm of HF;

based on the total weight of the composition.

Advantageously, the composition comprises at least 99.5% by weight, advantageously at least 99.8% by weight, of 1,1,1,2, 3-pentafluoropropane.

Preferably, the composition comprises 1,1,1,2, 3-pentafluoropropane and 1,1,1,1, 3-tetrafluoropropane, and the mass content of 1,1,1,2, 3-pentafluoropropane in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 1,1,1, 3-tetrafluoropropane in the composition is less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10 ppm. Preferably, the 1,1,1, 3-tetrafluoropropane content is greater than 1 ppb.

Preferably, the composition comprises 1,1,1,2, 3-pentafluoropropane and 1,1,1,2,3, 3-hexafluoropropane, and the mass content of 1,1,1,2, 3-pentafluoropropane in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 1,1,1,2,3, 3-hexafluoropropane in the composition is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50 ppm. Preferably, the 1,1,1,2,3, 3-hexafluoropropane content is greater than 1 ppb.

The composition may comprise 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, and 1,1,1,2,3, 3-hexafluoropropane; the content by mass of 1,1,1,2, 3-pentafluoropropane in the composition is at least 99.5%, advantageously at least 99.8%; the mass content of 1,1,1,2,3, 3-hexafluoropropane in the composition is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50ppm, and the mass content of 1,1,1, 3-tetrafluoropropane in the composition is less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10 ppm.

Preferably, the composition comprises 1,1,1,2, 3-pentafluoropropane and 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane; the content by mass of 1,1,1,2, 3-pentafluoropropane in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the composition is less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, more in particular less than 1 ppm. Preferably, the 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane content is greater than 1 ppb.

Thus, the composition may comprise 1,1,1,2, 3-pentafluoropropane, 1,1,1, 3-tetrafluoropropane, 1,1,1,2,3, 3-hexafluoropropane and 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane; the content by mass of 1,1,1,2, 3-pentafluoropropane in the composition is at least 99.5%, advantageously at least 99.8%; the mass content of 1,1,1,2,3, 3-hexafluoropropane in the composition is less than 1000ppm, advantageously less than 750ppm, preferably less than 500ppm, more preferably less than 250ppm, in particular less than 100ppm, more in particular less than 50 ppm; the mass content of 1,1,1, 3-tetrafluoropropane in the composition is less than 500ppm, advantageously less than 375ppm, preferably less than 250ppm, more preferably less than 100ppm, in particular less than 50ppm, more in particular less than 10ppm and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the composition is less than 50ppm, advantageously less than 40ppm, preferably less than 30ppm, more preferably less than 20ppm, in particular less than 10ppm, more in particular less than 1 ppm.

Preferably, the composition is obtainable by the process for purifying 1,1,1,2, 3-pentafluoropropane according to the present invention.

According to another aspect of the present invention, a composition is provided. Preferably, the composition comprises:

at least 99.5% by weight, advantageously at least 99.8% by weight, of 2,3,3, 3-tetrafluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5ppm of 3,3, 3-trifluoropropene,

less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, of 1,2,3,3, 3-pentafluoropropene,

less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50ppm, of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane, and

less than 20ppm, advantageously less than 15ppm, preferably less than 10ppm, in particular less than 5ppm, of 1,1,1,2, 3-pentafluoropropane,

based on the total weight of the composition.

Preferably, the composition comprises 2,3,3, 3-tetrafluoropropene and 3,3, 3-trifluoropropene; the mass content of 2,3,3, 3-tetrafluoropropene in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 3,3, 3-trifluoropropene in the composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5 ppm.

Preferably, the composition comprises 2,3,3, 3-tetrafluoropropene and 1,2,3,3, 3-pentafluoropropene; the mass content of 2,3,3, 3-tetrafluoropropene in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 1,2,3,3, 3-pentafluoropropene in said composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, especially less than 10 ppm.

Preferably, the composition comprises 2,3,3, 3-tetrafluoropropene, 3,3, 3-trifluoropropene, and 1,2,3,3, 3-pentafluoropropene; the mass content of 2,3,3, 3-tetrafluoropropene in the composition is at least 99.5%, advantageously at least 99.8%; the mass content of 3,3, 3-trifluoropropene in the composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5 ppm; and the mass content of 1,2,3,3, 3-pentafluoropropene in said composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, especially less than 10 ppm.

Preferably, the composition comprises 2,3,3, 3-tetrafluoropropene and 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane; the mass content of 2,3,3, 3-tetrafluoropropene in the composition is at least 99.5%, advantageously at least 99.8%; and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the composition is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50 ppm.

Preferably, the composition comprises 2,3,3, 3-tetrafluoropropene, 3,3, 3-trifluoropropene, 1,2,3,3, 3-pentafluoropropene and 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane; the mass content of 2,3,3, 3-tetrafluoropropene in the composition is at least 99.5%, advantageously at least 99.8%; the mass content of 3,3, 3-trifluoropropene in the composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, in particular less than 10ppm, more in particular less than 5 ppm; the mass content of 1,2,3,3, 3-pentafluoropropene in said composition is less than 100ppm, advantageously less than 75ppm, preferably less than 50ppm, more preferably less than 25ppm, especially less than 10 ppm; and the mass content of 1,1, 2-trifluoroethane and/or 1,1, 1-trifluoroethane in the composition is less than 200ppm, advantageously less than 150ppm, preferably less than 100ppm, more preferably less than 75ppm, in particular less than 50 ppm.

In particular, in any of the above compositions comprising 2,3,3, 3-tetrafluoropropene, they may be free of 1,1,1,2, 3-pentafluoropropane.

Alternatively, in any of the above compositions comprising 2,3,3, 3-tetrafluoropropene, they may comprise less than 20ppm, advantageously less than 15ppm, preferably less than 10ppm, in particular less than 5ppm, of 1,1,1,2, 3-pentafluoropropane.

Preferably, the composition is obtainable by the process for the production of 2,3,3, 3-tetrafluoropropene according to the invention.

Figure 1a schematically shows a particular embodiment of the invention. In particular, fig. 1 shows a process for purifying 1,1,1,2, 3-pentafluoropropane and producing 2,3,3, 3-tetrafluoropropene according to a particular embodiment of the present invention. Composition a1 as described above was sent to distillation column 2 to form stream B1' recovered at the bottom of distillation column 2 and stream B1 recovered at the top of distillation column 2. Stream B1 is conveyed via a pipe 3 to an incineration plant 4. Stream B1' is sent to distillation column 6 via line 5. Stream B1 'is distilled to form and recover stream B2 as described herein at the top of the distillation column and stream B2' as described herein at the bottom of the distillation column. Stream B2' is conveyed to the incineration plant 9 through a pipe 10. Stream B2 is fed via line 7 to dehydrofluorination reactor 8 to enable dehydrofluorination of 1,1,1,2, 3-pentafluoropropane to produce 2,3,3, 3-tetrafluoropropene. Thus a stream C1 according to the invention is obtained at 8. Finally, stream C1 is sent via line 11 to purification unit 12, which preferably comprises at least one distillation column, in particular at least two distillation columns. The purification device 12 enables the formation of a stream C3 as described in the present application.

Figure 1b schematically shows a particular embodiment of the invention. In particular, figure 1b represents a process for purifying 1,1,1,2, 3-pentafluoropropane and producing 2,3,3, 3-tetrafluoropropene according to another particular embodiment of the present invention. Composition a1 as described above was fed to distillation column 2. In this case, the distillation column 2 is a dividing wall distillation column. Thus, the third stream comprising 1,1,1,2,3, 3-hexafluoropropane, 1,1, 2-trifluoroethane, 1,1, 1-trifluoroethane and 1,1,1, 2-tetrafluoropropane is recovered at the top of the distillation column. This stream is conveyed via a pipe 3 to an incineration plant 4. Said second stream comprising 1,1,1, 3-tetrafluoropropane is recovered at the bottom of a distillation column. This stream is conveyed via a pipe 5 to an incineration plant 9. Finally, said first stream comprising 1,1,1,2, 3-pentafluoropropane is recovered at a height h of distillation column 2 between the top and the bottom of the distillation column. The first stream is conveyed via conduit 7 to a dehydrofluorination reactor 8 to enable dehydrofluorination of 1,1,1,2, 3-pentafluoropropane to produce 2,3,3, 3-tetrafluoropropene. Thus a stream C1 according to the invention is obtained at 8. Finally, stream C1 is sent via line 11 to purification unit 12, which preferably comprises at least one distillation column, in particular at least two distillation columns. The purification device 12 enables the formation of a stream C3 as described in the present application.

Fig. 2a and 2b schematically show a particular embodiment of the invention. In particular, fig. 2a and 2b show a process for producing 2,3,3, 3-tetrafluoropropene, including a process for purifying 1,1,1,2, 3-pentafluoropropane according to the present invention. In reactor 30, hexafluoropropylene (reference 34) and hydrogen (reference 33) are contacted to form a stream comprising 1,1,1,2,3, 3-hexafluoropropane. This stream is conveyed to reactor 31 via conduit 38. 1,1,1,2,3, 3-hexafluoropropane is dehydrofluorinated in reactor 31 to form a stream comprising 1,2,3,3, 3-pentafluoropropene. This stream is conveyed to reactor 32 and is brought into contact with hydrogen (numeral 36) to form composition a1 according to the invention. Composition a1 is transported to distillation column 2 via line 40 to form stream B1' recovered at the bottom of distillation column 2 and stream B1 recovered at the top of distillation column 2. Stream B1 is conveyed via a pipe 3 to an incineration plant 4. Stream B1' is sent to distillation column 6 via line 5. Stream B1 'is distilled to form and recover stream B2 as described herein at the top of the distillation column and stream B2' as described herein at the bottom of the distillation column. Stream B2' is conveyed to the incineration plant 9 through a pipe 10. Stream B2 is fed via line 7 to dehydrofluorination reactor 8 to enable dehydrofluorination of 1,1,1,2, 3-pentafluoropropane to 2,3,3, 3-tetrafluoropropene. Thus a stream C1 according to the invention is obtained at 8. Stream C1 is finally sent to distillation column 14 via conduit 13 to form said stream C2 at the top of the distillation column and said stream C2' at the bottom of the distillation column. Stream C2 is sent to the incinerator 16 via pipe 15. Stream C2 'is sent via line 17 to distillation column 18 to recover said stream C3 at the top of the distillation column and said stream C3' at the bottom of the distillation column. Said stream C3 comprising 2,3,3, 3-tetrafluoropropene is sent to storage unit 20 through line 19. Said stream C3' comprising 1,1,1,2, 3-pentafluoropropane is recycled to reactor 8 (fig. 2a, 3a, 3b) or to the outlet of reactor 32 (fig. 2b, 4a and 4 b).

The stream obtained from reactor 31 and comprising 1,2,3,3, 3-pentafluoropropene may be purified prior to being sent to reactor 32. This is shown in fig. 3a, 3b, 4a and 4 b. In FIGS. 3a and 4a, the stream comprising 1,2,3,3, 3-pentafluoropropene at the outlet of reactor 31 is sent via conduit 43 to distillation column 41. Purified 1,2,3,3, 3-pentafluoropropene is recovered at the top of the distillation column and is transported to reactor 32 via conduit 39. This stream may also comprise 1,1,1, 2-tetrafluoroethane, 1,1, 2-trifluoroethane and 1,1, 1-trifluoroethane which form the stream D1 described above. Unreacted 1,1,1,2,3, 3-hexafluoropropane (stream D2) in reactor 31 is recovered at the bottom of distillation column 41 and is transported to the inlet of reactor 31 via conduit 42. Figures 3b and 4b show an embodiment of the purification of the stream obtained from the reactor 31 by means of two distillation columns. The stream comprising 1,2,3,3, 3-pentafluoropropene at the outlet of reactor 31 is conveyed via conduit 43 to distillation column 41. Stream D3 comprising 1,1, 2-trifluoroethylene is recovered at the top of the distillation column. Stream D3 may be upgraded or incinerated at 46 via line 45. At the bottom of the distillation column 41, a stream D3' comprising 1,2,3,3, 3-pentafluoropropene and 1,1,1,2,3, 3-hexafluoropropane is recovered and sent to the distillation column 44 via line 42. Stream D4 comprising 1,2,3,3, 3-pentafluoropropene is withdrawn at the top of the distillation column and is transported to reactor 32 via conduit 39. Stream D4' comprising 1,1,1,2,3, 3-hexafluoropropane is withdrawn at the bottom of the distillation column and recycled to the inlet of reactor 31 via line 47.