The invention relates to a process for preparing 2,3,3,3-tetrafluoro-l-propene.

More particularly, the invention relates to a process for preparing 2,3,3,3-tetrafluoro-l-propene including the purification and recycle of 2-chloro-3,3,3-trifluoropropene from the reaction also .

BACKGROUND OF THE INVENTION

Hydrofluorocarbons (HFCs) and particularly hydrofluoroolefins (HFOs), such as 2,3,3,3-tetrafluoro-the l-propene (HFO-1234yf) are compounds known for their cooling properties and heat transfer fluids, fire extinguishing, propellants, foaming agents, blowing agents, gaseous dielectrics, polymerization medium or monomer, fluid media, abrasives agents, drying agents and fluids for energy production unit. The HFO have been identified as desirable alternatives to HCFCs due to their low values ​​ODP (Ozone Depletion Potential and potential to deplete the ozone layer) and GWP (Global Warming Potential or GWP).

Most manufacturing processes hydrofluoroolefins use a fluorination reaction and / or dehydrohalogenation. This type of reaction is carried out in the gas phase and generates impurities that must therefore be removed to obtain the desired compound in sufficient purity for the intended applications.

For example, in the context of the production of 2,3,3,3-tetrafluoro-l-propene (HFO-1234yf), the presence of impurities such as l-chloro-3,3,3-trifluoro-l propene (1233zd), 1,3,3,3-tetrafluoro-l-propene (1234ze), and 1,1,1,3,3-pentafluoropropane (245fa) are observed. These impurities are isomers of the major components to be obtained by the method for producing 2,3,3,3-tetrafluoro-l-propene addition thereto, ie 2-chloro-3,3,3-trifluoro-l- propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb). Given the respective boiling points of l-chloro-3,3,3-trifluoro-l-propene (1233zd), 1,3,3,3-tetrafluoro-l-propene (1234ze) and 1,1, 1,3,3-pentafluoropropane (245fa), they can accumulate in the loop product is recycled to the reactor and thus prevent the formation of products of interest.

Purification of this type of reaction may be effected by various techniques known to the prior art, such as e.g. distillation. However, when the compounds to be purified have boiling points too close or when they form azeotropic or near-azeotropic compositions, distillation is not an efficient process. extractive distillation methods have been described.

Is known from EP 0864554 a method for purifying a mixture comprising 1,1,1,3,3-pentafluoropropane (245fa) and l-chloro-3,3,3-trifluoro-trans-l-propene (1233zd ) by distillation in the presence of a solvent having a higher boiling point than 1-chloro-3,3,3-trifluoro-trans-l-propene.

by WO 03/068716 discloses a method of recovering pentafluoroethane from a mixture comprising pentafluoroethane and chloropentafluoroethane by distillation in the presence of hexafluoropropene.

is also known from WO 98/19982 a method for purifying 1,1-difluoroethane by extractive distillation. The method comprises contacting an extraction agent with a mixture of 1,1-difluoroethane and vinyl chloride. The extraction agent selected from hydrocarbons, alcohols, chlorocarbons having a boiling point between 10 ° C and 120 ° C.

As mentioned in WO 98/19982, the selection of the extracting agent can be complex depending on the products to be separated. There is therefore still a need for the implementation of a particular method of purification of 2-chloro-3,3,3-trifluoropropene.

Summary of the Invention

In a method for producing 2,3,3,3-tetrafluoro-l-propene, the choice of particular operating conditions can promote the presence of certain impurities or isomers thereof. The presence of impurities such as l-chloro-3,3,3-trifluoro-l-propene (1233zd) and 1,1,1,3,3-pentafluoropropane (245fa) can be observed. These impurities can originate from side reactions induced by intermediately compounds produced during production of 2,3,3,3-tetrafluoro-l-propene, and may have physical properties such as the separation thereof with 2-chloro -3,3,3-trifluoropropene (1233xf) can be complex. There is therefore an interest in treating the feedback loop to limit the presence of impurities. In addition, the present invention allows, in addition the production of 2,3,3,3-tetrafluoro-l-propene, recovery and recycling of the 2-chloro-3,3,3-trifluoropropene (1233xf) product with excellent purity.

According to a first aspect, the present invention provides a process for purifying 2-chloro-3,3,3-trifluoropropene (1233xf) from a first composition comprising 2-chloro-3,3,3-trifluoropropene and least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1, 3,3,3-hexafluoropropane (236fa), said method comprising the steps of:

a) contacting said first composition with at least one organic extractant to form a second composition; b) extractive distillation of said second composition to form:

i) a third composition comprising said organic extractant and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1, 3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa), ii) a stream comprising 2-chloro-3,3,3-trifluoropropene;

c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l- propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa).

Preferably, the stream comprising the organic extractant may be recycled to step a). Preferably, the stream comprising said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa ) and 1,1,1,3,3,3-hexafluoropropane (236fa) can be incinerated or recovered in order to purify one or more of the product component.

According to a preferred embodiment, the organic extractant separated in step c) is recycled to step a).

According to a preferred embodiment, said stream comprising 2-chloro-3,3,3-trifluoropropene formed in step b) is recovered from the distillation column overhead and optionally recycled to a process for producing 2,3, 3,3-tetrafluoropropene.

According to a preferred embodiment, said organic extractant is a solvent selected from the group consisting of hydrocarbon, hydrohalocarbure, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, sulfoxide, sulfate, thioalkyl, amide, heterocycle and phosphate or organic extraction agent is perfluorobutanoic acid.

According to a preferred embodiment, said organic extractant has a boiling point between 50 and 200 ° C.

According to a preferred embodiment, said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (Y2, s * P2) wherein

Yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene, Y2, s represents the coefficient of activity of said at least one of the compounds consisting of E-l-chloro-3,3,3-trifluoro -l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa) in said organic extractant at infinite dilution,

P2 represents the saturation vapor pressure of said at least one of the compounds consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1 , 1,1,3,3,3-hexafluoropropane (236fa);

preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0.

In the present application, the saturation vapor pressure is considered to a temperature of 25 ° C.

According to a preferred embodiment, said organic extractant has an absorption capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (Y2, s ) wherein Y2, s represents the coefficient of activity of said at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3 , 3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa) in said organic extractant at infinite dilution;

advantageously C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.

According to a preferred embodiment, said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (Yi, s * PI) / (Y2, s * P2) wherein

Yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene,

Y2, s is the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution,

P2 represents the saturation vapor pressure of 1,1,1,3,3-pentafluoropropane (245fa); preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0;

and

said organic extractant has an absorption capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s represents the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution; advantageously C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.

Thus, in a particular embodiment, said organic extractant may be selected from the group consisting of ethanedial, propanone, methylacetate, Methylglyoxal, ethylacetate, butanone, propionitrile, dioxane, trimethoxymethane, 1,3-dioxane, 1.3 , 5-trioxane, 1,2-diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2-methoxyl-propanol, l-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, methylacetoacetate, η, η-dimethylpropanamide, dimethyl malonate, diethyl sulfoxide, 2- (2-methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate; preferably said organic extractant may be selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1,2-diaminoethane, l- methoxy-2-propanol. Preferably, this particular embodiment can effectively separate 2-chloro-3,3,3-trifluoropropene and 1,1,1,3,3-pentafluoropropane (245fa).

According to a particular embodiment, said organic extractant may have a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein

yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene,

Y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene

(1233zdE) in said organic extractant at infinite dilution,

P2 represents the saturation vapor pressure of the El-chloro-3,3,3-trifluoro-l-propene

(1233zdE);

preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0;

and

said organic extractant can have an absorbent capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l- propene (1233zdE) in said organic extractant at infinite dilution; advantageously C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.8, in particular greater than or equal to 1.0.

Ainsi, dans un mode de réalisation particulier, ledit agent d'extraction organique peut être choisi parmi le groupe consistant en isopropylmethylamine, methyl-t-butylether, diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, tetrahydrofurane, 1-butylamine, ethylacetate, butanone, n-propylformate, -dimethoxypropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, l-methoxy-2-propanamine, 2-methoxyethanamine, tert-butylacetate, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-l,2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, 1-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, l-(dimethylamino)-2-propanol, 3-methyl-3-pentanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 2-methoxyl-propanol, l-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-ethoxy-l-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, η,η-diethylethylenediamine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, l-propoxy-2-

propanol, 2-heptanone, dimethylformamide, 2-isopropoxyethanol, 2-methylpiperazine, cyclohexanone, 1-heptanamine, 2-ethoxyethanolacetate, 1,4-butanediamine, 2,4-dimethylpyridine, 2-methoxy-3-methylpyrazine, 4-methoxy-4-methyl-pentan-2-one, 3-ethoxy- 1- propanol, 3-methoxy-l-butanol, diglyme, 2-(diethylamino)-ethanol, 2,2-diethoxyethanamine, 2-methoxy-n-(2-methoxyethyl)ethanamine, 2-(ethylamino)ethanol, 3-octanone, diacetone alcohol, diethylaminopropylamine, 2-ethylhexylamine, l-butoxy-2-propanol, 2-butoxyethanol,

2- octanone, methylheptanoate, triethylenediamine, η,η-dimethylpropanamide, 2-propanol-l-methoxy-propanoate, 1,5-pentanediamine, cycloheptanone, 3,4-dimethylpyridine, 1-octanamine, benzylmethylamine, 1,1,3,3-tetramethoxypropane, dihexylphthalate, diethylpropanolamine, 2-butoxyethanolacetate, diethylsulfoxide, 2-(2-methoxyethoxy)ethanol, 4-methylbenzenemethanamine, diethyleneglycolmonoethylether, 2-propylcyclohexanone, trimethylphosphate, 2-methyl-2,4-pentanediol, methylbenzoate, diethylmalonate, 2-methoxypyrimidine ; de préférence ledit agent d'extraction organique est choisi parmi le groupe consistant en diethylamine, propanone, methylacetate, tetrahydrofurane, ethylacetate, butanone, diethoxymethane, isopropylacetate, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy2-propanol, n-butylacetate, l-ethoxy-2-propanol. De préférence, ce mode de réalisation particulier peut permettre de séparer efficacement 2-chloro-3,3,3-trifluoropropène et E-l-chloro-3,3,3-trifluoro-l-propene (1233zdE).

According to a particular embodiment, said organic extractant may be selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, l-methoxy-2-propanol , diethylcarbonate, 2-methoxyl-propanol, l-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, η, η-dimethylpropanamide, diethyl sulfoxide, 2- (2-methoxyethoxy) ethanol, trimethyl phosphate, diethylmalonate ; preferably said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, 1-methoxy-2-propanol, 3-methoxy-l- butanol, diacetone alcohol. Preferably, this particular embodiment can effectively and simultaneously separate the 2-chloro-3,3,3-trifluoropropene, El-chloro-3,3,3-trifluoro-l-propene (1233zdE) and 1, 1,1,3,3-pentafluoropropane (245fa).

According to a particular embodiment, the first composition is an azeotropic composition or quasi-azeotropic comprising 2-chloro-3,3,3-trifluoropropene and El-chloro-3,3,3-trifluoro-l-propene (1233zdE); or the first composition is an azeotropic composition or quasi-azeotropic comprising 2-chloro-3,3,3-trifluoropropene and 1, 1, 1,3,3-pentafluoropropane (245fa).

According to a second aspect of the present invention, a process for producing 2,3,3,3-tetrafluoro-l-propene is provided. Said method comprises the steps of:

A) in a reactor in the presence of a fluorination catalyst to a compound of formula CX (Y) 2 -CX (Y) m -CH m XY (I) wherein X and Y are independently H, F, or Cl and m = 0 or 1; and / or fluorination in the presence of a catalyst of a compound of formula (CXnY3-n) CHpXi pCH- m X 2-m (II) wherein X is independently of each other Cl, F, I or Br; Y is independently of each other H, Cl, F, I or Br; n is 1, 2 or 3; and m is 0, 1 or 2; and p is 0 or 1;

B) recovering a stream, preferably from a purge from the reaction recycle loop, comprising 1,1, 1,2,2-pentafluoropropane, 2-chloro-3,3,3-trifluoropropene, and at least one of the compounds selected from the group consisting of E-l-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1, 1, 1,3,3-pentafluoropropane (245fa) and 1, 1 , 1,3,3,3-hexafluoropropane (236fa),

C) distilling the stream recovered in step B) and recovery distillation column overhead a stream comprising 1, 1,1,2,2-pentafluoropropane and at the bottom of distillation column a stream comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1, 1.1 , 3,3-pentafluoropropane (245fa) and 1, 1,1,3,3,3-hexafluoropropane (236fa);

D) implementation of the purification process of 2-chloro-3,3,3-trifluoropropene of the present invention from the stream recovered in step C) and comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zd E), 1, 1,1,3,3-pentafluoropropane (245fa) and 1, 1,1,3,3,3-hexafluoropropane (236fa); and

E) recycling to step A) of the stream comprising 2-chloro-3,3,3-trifluoropropene formed and recovered in step b) of the purification process implemented in step D). According to a preferred embodiment, the stream comprising 1, 1,1,2,2-pentafluoropropane recovered in step C) in distillation column overhead can be recycled, for example in the reaction loop, that is i.e. in step A).

Preferably, the method for producing 2,3,3,3-tetrafluoro-l-propene is carried out in a device comprising a reactor and a reaction loop recycling. The latter can be served.

According to a preferred embodiment, the stream recovered in step B) also comprising HF, 1,1,1,2,2-pentafluoropropane and 1,3,3,3-tetrafluoro-l-propene (1234ze), those - this being prior to the implementation of the distillation step C), treated according to the following steps:

i) low temperature separation of said liquid composition to form a first phase rich in HF and a second organic layer containing 1,3,3,3-tetrafluoro-l-propene (1234ze) 1,1,1,2,2 -pentafluoropropane and 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1, 1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa);

ii) distilling said second organic phase to form and recover, preferably distillation column, a first stream comprising 1,1,1,2,2-pentafluoropropane and 1,3,3,3-tetrafluoro-l-propene (1234ze), and to form and recover, preferably at the bottom of distillation column, a second stream comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El - chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa);

iii) recovering said second current and implement Step D) from thereof.

According to another aspect, the invention provides a composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf), El-chloro-3,3,3-trifluoro-l-propene (1233zdE) and an agent organic extractant having a separation factor If two greater than or equal to 1.6, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein yi , s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene (1233xf) in said organic extractant at infinite dilution, PI represents the saturation vapor pressure of 2-chloro-3,3, 3-trifluoropropene (1233xf), y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-1-propene (1233zdE) in said organic extractant at infinite dilution, P2 represents the pressure saturated vapor of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), preferably said organic extractant has a C2 absorbency, s greater than or equal to 1.0, said capacitor of absorptio n being calculated by the formula C2, s = l / (y2, s) wherein y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE) in said agent organic extraction at infinite dilution; preferably said organic extractant is selected from the group consisting of isopropylmethylamine, methyl-t-butylether, diethylamine, propanone, methyl acetate, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate , -dimethoxypropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, l-methoxy-2-propanamine, 2-methoxyethanamine, tert-butylacetate, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butyl acetate, n-methyl-l, 2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl- 5-heptenal, l- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 2-ethylbutylamine, diethyl carbonate, n-butylacetate, 2-hexanone, n-and hylethylenediamine, 2-methoxyl-propanol, l-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2- ethoxy-l-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, η, η-diethylethylenediamine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-l, 2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-Propoxyethanol, l-propoxy-2-propanol, 2-heptanone, dimethylformamide, 2-isopropoxyethanol, 2-methylpiperazine , cyclohexanone, 1-heptanamine, 2-ethoxyethanolacetate, 1,4-butanediamine, 2,4-dimethylpyridine, 2-methoxy-3-methylpyrazine, 4-methoxy-4-methyl-2-pentanone, 3-ethoxy-1 - propanol, 3-methoxy-l-butanol, diglyme, 2- (diethylamino) -ethanol, 2,2-diethoxyethanamine, 2-methoxy-N- (2-methoxyethyl) ethanamine, 2- (ethylamino) ethanol, 3-octanone , diacetone alcohol, DIETHYLAMINOPROPYLAMINE, 2-ethylhexylamine, l-butoxy-2 propanol, 2-butoxyethanol,

2- octanone, methylheptanoate, triethylenediamine, η,η-dimethylpropanamide, 2-propanol-l-methoxy-propanoate, 1,5-pentanediamine, cycloheptanone, 3,4-dimethylpyridine, 1-octanamine, benzylmethylamine, 1,1,3,3-tetramethoxypropane, dihexylphthalate, diethylpropanolamine, 2-butoxyethanolacetate, diethylsulfoxide, 2-(2-methoxyethoxy)ethanol, 4-methylbenzenemethanamine, diethyleneglycolmonoethylether, 2-propylcyclohexanone, trimethylphosphate, 2-methyl-2,4-pentanediol, methylbenzoate, diethylmalonate, 2-methoxypyrimidine ; en particulier ledit agent d'extraction organique est choisi parmi le groupe consistant en diethylamine, propanone, methylacetate, tetrahydrofurane, ethylacetate, butanone, diethoxymethane, isopropylacetate, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy2-propanol, n-butylacetate, l-ethoxy-2-propanol.

According to another aspect, the invention provides a composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3,3-pentafluoropropane (245fa) and an organic extractant having a separation factor If two greater than or equal to 1.6, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein yi, s represents the activity coefficient of 2-chloro-3,3,3-trifluoropropene (1233xf) in said organic extractant at infinite dilution, PI represents the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene ( 1233xf), y2, s is the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution, P2 represents the saturation vapor pressure of 1.1, 1,3,3-pentafluoropropane (245fa), preferably said organic extractant has a C2 absorbency, s greater than or equal to 1.0, said absorptive capacity is calculated by f ormule C2, s = l / (y2, s) wherein Y2, s is the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution; preferably said organic extractant is selected from the group consisting of ethanedial, propanone, methylacetate, Methylglyoxal, ethylacetate, butanone, propionitrile, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1.2 -diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2-methoxyl-propanol, l-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, methylacetoacetate, η, η-dimethylpropanamide, dimethyl malonate, diethyl sulfoxide, 2- (2-methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate; in particular said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1,2-diaminoethane, l-methoxy -2-propanol ..

According to another aspect, the invention provides an azeotropic composition or quasi-azeotropic comprising from 45 to 65 mole% of 2-chloro-3,3,3-trifluoropropene (1233xf) and 35 to 55 mole% 1,1,1 , 3,3-pentafluoropropane (245fa) based on the total composition.

According to another aspect, the invention provides a composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3,3-pentafluoropropane (245fa), El-chloro-3,3, 3-trifluoro-l-propene (1233zdE) and an organic extractant selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-

dioxane, 1,2-diaminoethane, l-methoxy2-propanol, diethylcarbonate, 2-methoxyl-propanol, 1-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxy-l-butanol, diacetone alcohol, n,n-dimethylpropanamide, diethylsulfoxide, 2-(2-methoxyethoxy)ethanol, trimethylphosphate, diethylmalonate ; de préférence un agent d'extraction organique sélectionné parmi le groupe consistant en propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, l-methoxy2-propanol, 3-methoxy-l-butanol, diacetone alcohol.

BRIEF DESCRIPTION OF FIGURES

Figures la-d show schematically a device implementing a method for purifying 2-chloro-3,3,3-trifluoropropene according to particular embodiments of the present invention.

2 schematically shows a device implementing a method for producing 2,3,3,3-tetrafluoropropene according to a particular embodiment of the present invention.

Detailed Description of the Invention

The term "hydrocarbon" as used herein refers to linear or branched alkane compounds C1-C20, C3-C20 cycloalkane, alkene, C5-C20, C5-C20 cycloalkene, arene C6-C18. For example, the alkane term refers to compounds of formula C n H 2n + 2 wherein n is between 1 and 20. The term alkane C1-C20 includes, for example pentane, hexane, heptane, octane, nonane, decane or isomers thereof. The term C 5 -C 20 alkene refers to hydrocarbon compounds containing one or more carbon-carbon double bonds and comprising 5 to 20 carbon atoms. The term cycloalkane C3-C20 refers to a saturated hydrocarbon ring having 3 to 20 carbon atoms. The term C6-C18 refers to cyclic and aromatic hydrocarbon compounds having 6 to 18 carbon atoms. Cycloalkene the term C5-C20 refers to cyclic hydrocarbon compounds comprising from 5 to 20 carbon atoms and comprising one or more double carbon-carbon bonds.

The term "alkyl" means a monovalent radical derived from an alkane, linear or branched, comprising 1 to 20 carbon atoms. The term "cycloalkyl" means a monovalent radical derived from a cycloalkane having 3 to 20 carbon atoms. The term "aryl" means a monovalent radical derived from an arene having 6 to 18 carbon atoms. The

term "alkenyl" denotes a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon double bond. The term "alkynyl" refers to a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon triple bond. The term "halogen" refers to a group F, Cl, Br or -I. The term "cycloalkenyl" refers to a monovalent radical derived from a cycloalkene having 3 to 20 carbons. The alkyl substituents C1-C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 may be substituted or not by one or more -OH, halogen, -P (0) (OR a ) 2 , -NR a C (0) R b , -C (0) NR a R b -CN, -N0 2 , -NR a R b , -OR a , - SR a , -C0 2 R a , -OC (0) OR a , -OC (0) R a , -C (0) H, -C (0) R a , -S (0) R a wherein R a and R b are independently of one another hydrogen, unsubstituted C1-C20 alkenyl, unsubstituted C2-C20 alkynyl unsubstituted C2-C20 cycloalkyl, unsubstituted C3-C20 cycloalkenyl, C3 C20 unsubstituted aryl, C6-C18 unsubstituted. In the substituents -NR a R b , R a and R b may form with the nitrogen atom to which they are attached, a saturated or unsaturated, aromatic or nonaromatic, comprising from 5 to 10 ring members.

The term "hydrohalocarbures" refers to compounds of formula R a X where

R a is selected from C1-C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 and X represents a chlorine, fluorine , bromine or iodine. The alkyl substituents C1-C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 may be substituted or not by one or more -OH, halogen, -P (0) (OR a ) 2 , -NR a C (0) R b , -C (0) NR a R b -CN, -N0 2 , -NR a R b , -OR a , - SR a , -C0 2 R a , -OC (0) OR a , -OC (0) R a , -C (0) H, -C (0) R a , -S (0) R a wherein R a and R b are as defined above.

The term "alcohol" refers to hydrocarbons or hydrohalocarbures as defined above wherein at least one hydrogen atom is replaced with a hydroxyl group -OH.

The term "ketone" refers to hydrocarbons comprising at least one or more carbonyl functional groups R c -C (0) -R d wherein R c and R d are independently from each other alkyl, C1- C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 and may be substituted or not by one or more -OH, halogen, -P ( 0) (OR a ) 2 , -NR a C (0) R b , -C (0) NR a R b -CN, -N0 2 , -NR a R b , -OR a , -SR a , -C0 2 R a , -OC (0) OR a , -OC (0) R a , -C (0) H, -C (0) R a , -S (0) R a wherein R a and R b are , R c and R d may be linked together to form with the carbonyl group to which they are attached a cyclic ketone having 4 to 10 ring members, preferably from 4 to 7 members. the ketone

ring may also comprise one or more double carbon-carbon bonds. The cyclic ketone may also be unsubstituted or substituted with one or more substituents as defined above.

The term "amino" refers to hydrocarbons comprising at least one or more amine functional groups -N cd wherein R c and R d are as defined above, R c and R d may be linked together to form with the nitrogen atom to which they are attached an aromatic or nonaromatic heterocycle containing from 4 to 10 ring members.

The term "esters" refers to compounds of the formula R c -C (0) -0-R d wherein R c and R d are as defined above, R c and R d may be linked together to form with the ester group a ring comprising from 4 to 20 carbon atoms.

The term "ether" refers to compounds of the formula R c -0-R d wherein R c and R d are as defined above, R c and R d may be linked together to form with the atom oxygen which they are attached a heterocycle containing 4 to 20 carbon atoms.

The term "aldehyde" refers to compounds comprising at least one or more functional groups -C (0) -H.

The term "nitrile" refers to compounds comprising at least one or more functional groups -CN.

The term "carbonate" refers to compounds of the formula R c -0-C (0) -0-R d wherein R c and R d are as defined above.

The term "sulfoxide" refers to compounds of the formula R c S (0) R d wherein R c and

R d are as defined above.

The term "sulfate" relates to compounds of formula R c S (0) 2R d .

The term "thioalkyl" refers to compounds of the formula R c SR d wherein R c and R d are as defined above.

The term "amide" refers to compounds of the formula R c C (0) NR e R d wherein R c and

R d are as defined above, R e being defined by the same substituents as R c , R c and R d may be linked together to form with the amide group -C (0) N to which they are attached a cyclic amide containing from 4 to 10 ring members, preferably from 4 to 7 members. The cyclic amide can also include one or more double carbon-carbon bonds. The cyclic amide can also be unsubstituted or substituted with one or more substituents as defined above.

The term "heterocycle" refers to a carbocycle containing from 4 to 10 ring members of which at least one of the ring members is a heteroatom selected from the group consisting of O, S, P and N. The heterocyclic ring may comprise one or more carbon double bond atoms or one or more double carbon-heteroatom bond or one or more double hetero atom-hetero atom bond. Preferably, the heterocycle may comprise 1, 2, 3, 4 or 5 heteroatoms as defined above. In particular, the heterocycle may comprise 1, 2 or 3 heteroatoms selected from oxygen, nitrogen or sulfur. Preferably, the heterocycle may be a carbon ring comprising 4 to 6-membered ring including 1, 2 or 3 ring members are heteroatoms selected from O or N; preferably O. The heterocycle may be unsubstituted or substituted by one or more substituents selected from -OH, halogen, -P (0) (O a ) 2 , -NR a C (0) R b , -C (0) NR a R b -CN, -N0 2 , -NR a R b , -OR a , -SR a , -C0 2 R a , -OC (0) OR a , -OC (0) R a , -C ( 0) H, -C (0) R a , -S (0) R a wherein R a and R b are as defined above.

The term "phosphate" refers to a compound of formula (RO) sP (O) wherein R c is as defined above.

The term "azeotropic composition" refers to a liquid mixture of two or more compounds that behave as a single substance, and which boils at fixed temperature keeping an identical composition in liquid phase to the gas phase. The term "quasi-azeotropic composition" refers to a liquid mixture of two or more compounds having a constant boiling or which tends not to split when subjected to boiling or evaporation.

According to a first aspect, the invention relates to a process for purifying 2-chloro-3,3,3-trifluoropropene (1233xf). The purification process is performed from a first composition comprising 2-chloro-3,3,3-trifluoropropene and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro- l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa).

Preferably, said method comprises the steps of:

a) contacting said first composition with at least one organic extractant to form a second composition; b) extractive distillation of said second composition to form:

i) a third composition comprising said organic extractant and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1, 3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa), ii) a stream comprising 2-chloro-3,3,3-trifluoropropene;

c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l- propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa).

Alternatively, step c) may be optional.

Preferably, the stream comprising said organic templating agent is recycled to step a). Preferably, the stream comprising said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa ) and 1,1,1,3,3,3-hexafluoropropane (236fa) is incinerated or recovered to extract and purify a thereof constituents.

Said first composition may comprise 2-chloro-3,3,3-trifluoropropene and at least one, at least two or all the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l -propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa).

Said first composition may comprise between 50 and 99.99% by weight of 2-chloro-3,3,3-trifluoropropene based on the total weight of the first composition, preferably between 55 and 99.9% by weight, preferably between 55 and 95% and especially between 60 and 90% by weight of 2-chloro-3,3,3-trifluoropropene based on the total weight of the first composition.

When it contains, said first composition may comprise between 0.01 and 50

% By weight of Al-chloro-3,3,3-trifluoro-l-propene (1233zdE) based on the total weight of the first composition, preferably between 0.01 and 40% by weight, preferably between 0.01 and 30% and in particular between 0.01 and 20% by weight of Al-chloro-3,3,3-trifluoro-l-propene (1233zdE) based on the total weight of the first composition.

When it contains, said first composition may comprise between 0, 01 and 50

% By weight of 1,1,1,3,3-pentafluoropropane (245fa) based on the total weight of the first composition, preferably between 0.01 and 40% by weight, preferably between 0.01 and 30% and particularly between 0.01 and 20% by weight of 1,1,1,3,3-pentafluoropropane (245fa) based on the total weight of the first composition.

When it contains, said first composition may comprise between 0.01 and 15

% By weight of 1,1,1,3,3,3-hexafluoropropane (236fa) based on the total weight of the first composition, preferably between 0.01 and 10% by weight, preferably between 0.01 and 7% and in particular between 0.01 and 5% by weight of 1,1,1,3,3,3-hexafluoropropane (236fa) based on the total weight of the first composition.

According to a particular embodiment, said organic extractant is a solvent selected from the group consisting of hydrocarbon, hydrohalocarbure, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, sulfoxide, sulfate, thioalkyl, amide, heterocyclic and phosphate. Said organic extractant may also be the perfluorobutanoic acid. Preferably, said organic extractant is a solvent selected from the group consisting of alcohol, ketone, amine, ester, ether, aldehyde, carbonate, sulfoxide, amide, heterocycle and phosphate.

Said organic extraction agent refers to a compound having at least one carbon atom.

Preferably the hydrocarbons are selected from the group consisting of cyclohexene, 1,3,5-triethylbenzene, 2,4,4-trimethyl-l-pentene, 1-methylcyclohexene, 1,4-dimethylbenzene, styrene, 1.3, 5-trimethylbenzene, 1,2,4,5-tetramethylbenzene, 1,3-diethenylbenzene.

De préférence, les hydrohalocarbures sont sélectionnés parmi le groupe consistant en 2-chloro-2-methylpropane, l-chloro-2,2-difluoropropane, 1,1-dichloroethane 2-bromopropane, 2-chlorobutane, 1-bromopropane, 2-bromo-2-methylpropane, l-chloro-3-fluoropropane, 1-chlorobutane, 2-chloro-2-methylbutane, 1,2-dichloroethane, 1,1-dichloropropane, l,2-dichloro-2-fluoropropane, 2-bromobutane, l-fluorohexane,2,3-dichloro-1-propene, 1,2-dichloropropane, 3-chloropentane, trichloroacetaldehyde, isoamylchloride, 1-chloro-4-fluorobutane, l-bromo-3-fluoropropane, 1-bromobutane, 2,2-dichlorobutane, cis-1,3-dichloropropene, 2-bromo-2-methylbutane, trans-l,3-dichloropropene, l,l,l-trichloro-3-fluoropropane, l-chloro-3,3-dimethylbutane, 2-bromopentane, 2,3-dichlorobutane, 1-bromo-3-methylbutane, l,3-dichloro-trans-2-butene, 1,3-dichloropropane, 1,2,2-trichloropropane, 1,2-dichlorobutane, 2,3-dichloro-2-methylbutane, 1-bromopentane, l,2-dichloro-2-butene, 1,3-dichlorobutane, l-chloro-3-bromopropane, 1,2-dichloropentane, 1-bromohexane, 1,2,3-trichloropropane, l,4-dichloro-trans-2-butene, 1,4-dichlorobutane, 2-chloropyridine, bromocyclohexane, 1,3-dibromopropane, 1,4-dichlorobenzene, 1-chlorooctane, 1-fluorodecane, 2-chloro-l,4-dimethylbenzene, 1,4-dibromobutane.

Preferably, the alcohols are selected from the group consisting of methanol, l, l, l-trifluoro-2-propanol, ethanol, 2-propanol, tert-butanol, 2,2-difluoroethanol, propanol, 2-allyloxyethanol, 2 butanol, 2,2,3,3-tetraflouro-l-propanol, l-methoxy-2-propanol, 1-

(dimethylamino)-2-propanol, 4,4,4-trifluorobutanol, 3-fluoropropanol, 2-chloroethanol, 2-methoxyl-propanol, l-ethoxy-2-propanol, 2-chloro-l-propanol, 2-(dimethylamino)-ethanol, 2-ethoxy-l-propanol, 2-propoxyethanol, l-propoxy-2-propanol, 2-isopropoxyethanol, 2-(methylamino)-ethanol, 3-ethoxy-l-propanol, 3-methoxy-l-butanol, 2-(diethylamino)-ethanol, 2-(ethylamino)ethanol, l-butoxy-2-propanol, 2-furanmethanol, 2-butoxyethanol, 2-aminopropanol, 2-amino-l-butanol, 2-methyl-2-nitro-l-propanol, 2-(ethylthio)-ethanol, propyleneglycol, 2-(2-methoxyethoxy)ethanol, 1,2-butanediol, glycol, 2-methyl-2,4-pentanediol.

Preferably, the ketones are selected from the group consisting propanone, butanone, 3-pentanone, 2-pentanone, 3,3-dimethyl-2-butanone, 4-methyl-2-pentanone, 2-hexanone, 5-hexen- 2-one, 4-methyl-2-hexanone, 2-heptanone, cyclohexanone, 4-methoxy-4-methyl-2-pentanone, 2,3-heptanedione, 3-octanone, diacetone alcohol, 2-octanone, cycloheptanone , dihydroxyacetone, 2-propylcyclohexanone.

Preferably, the amines are selected from the group consisting of 2-methoxyethanamine, n-methylhydroxylamine, 2-ethoxyethanamine, n-methyl-1,2-ethanediamine, 1,2-diaminoethane, 1,2-propanediamine, 1,3- propanediamine, dimethylethanolamine, 1,4 butane diamine, ethanolamine, diethylpropanolamine.

Preferably, the esters are selected from the group consisting of methylacetate, isopropylformate, ethylacetate, n-propylformate, isopropylacetate, t-butylacetate, ethylpropionate, sec-butyl acetate, diethyl carbonate, n-butylacetate, ,, isopropylchloroacetate methylhexanoate, 2-ethoxyethanolacetate, methylacetoacetate , methylheptanoate, 2-propanol-l-methoxy-propanoate, dimethyl malonate, dihexylphthalate, dimethyl sulfate, 2-butoxyethanolacetate, trimethyl phosphate, methyl benzoate, diethyl malonate.

Preferably, the ethers are selected from the group consisting of chloromethyl methyl, 1,2-dimethoxyethane, trimethoxymethane, 2-methoxyethanol, 2-chloro-l, l-dimethoxyethane, ethoxyethanol, l-methoxy-2-acetoxypropane, 1,1, 3,3-tetramethoxypropane, diethyleneglycolmonoethylether.

Preferably, the aldehydes are selected from the group consisting of ethanedial, isobutanal, Methylglyoxal, 2-methylbutanal, hexanal, heptanal, 3-hydroxy-butanal, furfural.

Preferably nitriles are selected from the group consisting of acetonitrile, propionitrile, butyronitrile, valeronitrile, (methyleneamino) acetonitrile, 3-methoxypropanenitrile.

Preferably, the carbonate may be diethylcarbonate.

Preferably, the sulfoxides are selected from the group consisting of dimethyl sulfoxide and diethyl sulfoxide.

Preferably, the dimethyl sulfate can be.

Preferably, the amides include dimethylformamide, 2,2,2-trifluoro-acetamide, N, N-dimethylpropanamide.

Preferably, thioalkyl may be the 3-mercapto-l, 2-propanediol.

Preferably, heterocycles are selected from the group consisting of tetrahydrofuran, dioxane, 1,3-dioxane, 1,3,5-trioxane, 3-furfural.

Preferably, the phosphate can be for example trimethyl.

The organic extraction agent to be used can be selected depending on the compounds present in said first composition. Thus, the organic extractant may be selected depending on the separation factor and the absorption capacity determined for a particular composition. Besides these two criteria, the choice of organic extraction agent can optionally be based on other commercial or environmental criteria, such as for example the cost of organic extraction agent, the availability on the market, its flammable or toxic properties. In addition, according to a particular embodiment, in order to optimize the operation of the distillation columns used in step b) and c) of this method of purification of 2-chloro-3,3,3-trifluoropropene, point boiling of the organic extractant may be 50 ° C to 200 ° C, preferably 50 ° C to 190 ° C, preferably 50 ° C to 180 ° C, particularly 50 ° C to 160 ° C, and preferentially from 50 ° C to 150 ° C, more preferred manner from 75 ° C to 150 ° C.

According to a preferred embodiment, said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (Y2, s * P2) wherein

Yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene,

Y2, s represents the coefficient of activity of said at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3 pentafluoropropane (245fa) in said organic extractant at infinite dilution, P2 represents the saturation vapor pressure of said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa).

In the present application, the saturation vapor pressure is considered to a temperature of 25 ° C. Advantageously, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0.

Said organic extractant may have an absorption capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s represents the coefficient of activity of said at least one of the compounds selected from the group consisting of l-chloro-3,3,3-trifluoro-l-propene (1233zd), 1,1,1,3,3-pentafluoropropane (245fa ) and 1,1,1,3,3,3-hexafluoropropane (236fa) in said organic extractant at infinite dilution. Advantageously, C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0, more particularly greater than or equal to 1.4, higher privileged manner or equal to 1.6. Thus, said organic extractant may have a separation factor If two greater than or equal to 1.1, advantageously greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8 and greater than or equal to 2.0; and a C2 absorbency, s greater than or equal to 0.20, advantageously greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.8, in particular greater than or equal to 1.0, more preferably greater than or equal to 1.4, higher privileged manner or equal to 1.6.

Preferably, said organic extractant may be selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2 -methoxyl-propanol, l-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxy-l-butanol, diacetone alcohol, η, η-dimethylpropanamide, diethyl sulfoxide, 2- (2-methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate. In particular, said organic extractant may be selected from the group consisting propanone, methylacetate, ethylacetate,

butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, l-methoxy2-propanol, 3-methoxy-l-butanol, diacetone alcohol.

Said first composition may be a composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene ( 1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa). Said first composition may be a composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least two or all the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro- l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa). The content of each compound in the first azeotropic or near-azeotropic composition is as expressed above.

Depending of the compound to be removed in said first composition, said separation factor and said absorption capacity may be calculated for a particular bit pair consisting of 2-chloro-3,3,3-trifluoropropene (1233xf) and one of compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa), and 1,1,1,3,3 , 3-hexafluoropropane (236fa). Thus, for selecting said organic extractant suitable for use in step b) of extractive distillation, the separation factor and the absorption capacity may be calculated for example for a binary Couple 2-chloro-3,3 , 3-trifluoropropene (1233xf) and 1,1,1,3,3-pentafluoropropane (245fa) if said first composition comprises these two compounds or a binary pair 2-chloro-3,3,3-trifluoropropene (1233xf) and El-chloro-3,3,3-trifluoro-l-propene (1233zdE) if said first composition comprises these two compounds. If the separation factor, two used to determine the ability of an organic extractant to separate two or more compounds. C2 absorbency, s to determine the amount of solvent to be used for the separation of the compounds concerned. For all raw compositions detailed below, said organic extractant may have a separation factor If two greater than or equal to 1.1, advantageously greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8 and greater than or equal to 2.0; and / or said organic extractant can have an absorbent capacity C2, s greater than or equal to 0.25, advantageously greater than or equal to 0.5, preferably greater than or equal to 0.75, more preferably greater than or equal to 1.0, more preferably greater than or equal to 1.4, higher privileged manner or equal to 1.6.

claims.
A process for purifying 2-chloro-3,3,3-trifluoropropene (1233xf) from a first composition comprising 2-chloro-3,3,3-trifluoropropene and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa) , said method comprising the steps of:

a) contacting said first composition with at least one organic extractant to form a second composition;

b) extractive distillation of said second composition to form:

i) a third composition comprising said organic extractant and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1, 3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa), ii) a stream comprising 2-chloro-3,3,3-trifluoropropene;

c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l- propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa.

Method according to the preceding claim characterized in that the stream comprising the organic extractant separated in step c) is recycled to step a).

A method according to any preceding claim characterized in that said stream comprising 2-chloro-3,3,3-trifluoropropene formed in step b) is recovered from the distillation column overhead and optionally recycled in a process for Production of 2,3,3,3-tetrafluoropropene.

The method of any one of the preceding claims, characterized in that said organic extractant is a solvent selected from the group consisting of hydrocarbon, hydrohalocarbure, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, sulfoxide, sulfate, thioalkyl, amide, heterocycle and phosphate, or organic extraction agent is perfluorobutanoic acid; preferably said organic extractant is a solvent selected from the group consisting of alcohol, ketone, amine, ester, ether, aldehyde, carbonate, sulfoxide, amide, heterocycle and phosphate.

A method according to any preceding claim characterized in that said organic extractant has a boiling point between 50 and 200 ° C.

A method according to any preceding claim in that said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene, Y2, s represents the coefficient of activity of said at least one of the compounds consisting of El-chloro-3,3,3-trifluoro-l -propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa) in said organic extractant at infinite dilution,

P2 represents the saturation vapor pressure of said at least one of the compounds consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1 , 1,1,3,3,3-hexafluoropropane (236fa);

preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0.

A method according to any preceding claim characterized in that said organic extractant has a C2 absorbency, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s represents the coefficient of activity of said at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1 , 1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa) in said organic extractant at infinite dilution;

advantageously C2 absorption capacity, s is greater than or equal to 0.5, preferably greater than or equal to 0.75, more preferably greater than or equal to 1.0.

A method according to any preceding claim characterized in that said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (yi , s * PI) / (y2, s * P2) wherein

yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene, Y2, s is the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said extractant organic at infinite dilution,

P2 represents the saturation vapor pressure of 1,1,1,3,3-pentafluoropropane (245fa); preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0;

and

said organic extractant has an absorption capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s represents the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution; advantageously C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.

Method according to the preceding claim characterized in that said organic extractant is selected from the group consisting of ethanedial, propanone, methylacetate, Methylglyoxal, ethylacetate, butanone, propionitrile, dioxane, trimethoxymethane, 1,3-dioxane, 1,3, 5-trioxane, 1,2-diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2-methoxyl-propanol, l-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, methylacetoacetate, n, n -dimethylpropanamide, dimethyl malonate, diethyl sulfoxide, 2- (2-

methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate; preferably said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1,2-diaminoethane, l-methoxy -2-propanol.

10. A method according to any one of claims 1 to 7 characterized in that said organic extractant has a separation factor If two greater than or equal to 1.1, said separation factor is calculated by the formula Si, 2 = (y i, s * PI) / (y2, s * P2) wherein yi, s is the activity coefficient of the 2-chloro-3,3,3-trifluoropropene in said organic extractant at infinite dilution ,

IP is the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene, Y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE) in said organic extractant at infinite dilution,

P2 represents the saturation vapor pressure of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE);

preferably, the separation factor If 2 is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, particularly greater than or equal to 2.0;

and

said organic extractant has an absorption capacity C2, s greater than or equal to 0.20, said absorptive capacity is calculated by the formula C2, s = l / (y2, s) wherein y2, s represents the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE) in said organic extractant at infinite dilution; advantageously C2 absorption capacity, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.

11. Method according to the preceding claim characterized in that said organic extractant is selected from the group consisting of isopropylmethylamine, methyl-t-butylether, diethylamine, propanone, methyl acetate, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1- butylamine, ethylacetate, butanone, n-propylformate, dimethoxypropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n

methylbutylamine, l-methoxy-2-propanamine, 2-methoxyethanamine, tert-butylacetate, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-l,2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, l-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, l-(dimethylamino)-2-propanol, 3-methyl-3-pentanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 2-methoxyl-propanol, l-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-ethoxy-l-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, η,η-diethylethylenediamine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, l-propoxy-2-propanol, 2-heptanone, dimethylformamide, 2-isopropoxyethanol, 2-methylpiperazine, cyclohexanone, 1-heptanamine, 2-ethoxyethanolacetate, 1,4-butanediamine, 2,4-dimethylpyridine, 2-methoxy-3-methylpyrazine, 4-methoxy-4-methyl-pentan-2-one, 3-ethoxy-l-propanol, 3-methoxy- 1- butanol, diglyme, 2-(diethylamino)-ethanol, 2,2-diethoxyethanamine, 2-methoxy-n-(2-methoxyethyl)ethanamine, 2-(ethylamino)ethanol, 3-octanone, diacetone alcohol, diethylaminopropylamine, 2-ethylhexylamine, l-butoxy-2-propanol, 2-butoxyethanol,

2- octanone, methylheptanoate, triethylenediamine, n,n-dimethylpropanamide, 2-propanol-l-methoxy-propanoate, 1,5-pentanediamine, cycloheptanone, 3,4-dimethylpyridine, 1-octanamine, benzylmethylamine, 1,1,3,3-tetramethoxypropane, dihexylphthalate, diethylpropanolamine, 2-butoxyethanolacetate, diethylsulfoxide, 2-(2-methoxyethoxy)ethanol, 4-methylbenzenemethanamine, diethyleneglycolmonoethylether, 2-propylcyclohexanone, trimethylphosphate, 2-methyl-2,4-pentanediol, methylbenzoate, diethylmalonate, 2-methoxypyrimidine ; de préférence ledit agent d'extraction organique est choisi parmi le groupe consistant en diethylamine, propanone, methylacetate, tetrahydrofurane, ethylacetate, butanone, diethoxymethane, isopropylacetate, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy2-propanol, n-butylacetate, l-ethoxy-2-propanol.

12. A method according to any preceding claim characterized in that said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2- diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2-methoxyl-propanol, 1-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, η, η-dimethylpropanamide, diethyl sulfoxide, 2- (2- methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate; preferably said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,2-diaminoethane, the methoxy2--propanol, 3-methoxy-l- butanol, diacetone alcohol.

13. A method according to any preceding claim characterized in that the first composition is an azeotropic composition or quasi-azeotropic comprising 2-chloro-3,3,3-trifluoropropene and El-chloro-3,3,3-trifluoro -l-propene (1233zdE); or the first composition is an azeotropic composition or quasi-azeotropic comprising 2-chloro-3,3,3-trifluoropropene and 1, 1,1,3,3-pentafluoropropane (245fa).

14. A process for producing 2,3,3,3-tetrafluoro-l-propene comprising the steps of:

A) in a reactor in the presence of a fluorination catalyst to a compound of formula (I) CX (Y) 2-CX (Y) m -CH m XY where X and Y independently represent a hydrogen atom, fluorine or chlorine and m = 0 or 1; and / or catalytic fluorination in the presence of a catalyst of a compound of formula (CXnY3-n) CHpXi pCH- m X 2-m (II) wherein X is independently of each other Cl, F, I or Br; Y is independently of each other H, Cl, F, I or Br; n is 1, 2 or 3; and m is 0, 1 or 2; and p is 0 or 1;

B) recovering a stream from a purge of the reaction recycling loop comprising 1, 1, 1,2,2-pentafluoropropane, 2-chloro-3,3,3-trifluoropropene and at least one compound selected from the group consisting of El-chloro-3,3,3-trifluoro-1-propene (1233zdE), 1, 1, 1,3,3-pentafluoropropane (245fa) and 1, 1, 1,3,3,3 - hexafluoropropane (236fa).

C) distilling the stream recovered in step B) and distillation column head recovering a stream comprising 1, 1,1,2,2-pentafluoropropane and down

distillation column a stream comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa);

D) implementation of the purification process of 2-chloro-3,3,3-trifluoropropene as claimed in any one of claims 1 to 8 from the stream recovered in step C) and comprising 2-chloro-3 , 3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3 pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa); and

E) recycling to step A) of the stream comprising 2-chloro-3,3,3-trifluoropropene formed and recovered in step b) of the purification process implemented in step D).

15. Method according to the preceding claim characterized in that the stream recovered in step B) also comprising HF, 1,1,1,2,2-pentafluoropropane and 1,3,3,3-tetrafluoro-l-propene ( 1234ze), these being, prior to the implementation of the distillation step C), treated according to the following steps:

i) low-temperature separation of said liquid composition to form a first phase rich in HF and a second organic phase containing 1,1,1,2,2- pentafluoropropane and 1,3,3,3-tetrafluoro-l-propene ( 1234ze), 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El-chloro-3,3,3-trifluoro-l-propene (1233zdE), 1, 1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa);

ii) distilling said second organic phase to form and recover, preferably distillation column, a first stream containing 1,1,1,2,2-pentafluoropropane and 1,3,3,3-tetrafluoro-l-propene (1234ze), and to form and recover, preferably at the bottom of distillation column, a second stream comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and at least one of the compounds selected from the group consisting of El - chloro-3,3,3-trifluoro-l-propene (1233zdE), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,3,3,3-hexafluoropropane (236fa);

iii) recovering said second current and implement Step D) from thereof.

16. A composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3,3-pentafluoropropane (245fa) and an organic extractant having a separation factor Si, 2 upper or equal to 1.6, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein yi, s represents the coefficient of activity of the 2-chloro -3,3,3-trifluoropropene (1233xf) in said organic extractant at infinite dilution, PI represents the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene (1233xf), y2, s represents the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution, P2 represents the saturation vapor pressure of 1,1,1,3,3-pentafluoropropane ( 245fa), preferably said organic extractant has an absorption capacity C2, s greater than or equal to 1.0, said absorptive capacity is calculated by the formula C2, s = l / (Y2, s) in wherein y2, s is the activity coefficient of 1,1,1,3,3-pentafluoropropane (245fa) in said organic extractant at infinite dilution; preferably said organic extractant is selected from the group consisting of ethanedial, propanone, methylacetate, Methylglyoxal, ethylacetate, butanone, propionitrile, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1.2 - diaminoethane, l-methoxy-2-propanol, diethyl carbonate, 2-methoxyl-propanol, 1-methoxy-2-acetoxypropane, dimethylformamide, 3-methoxyl-butanol, diacetone alcohol, methylacetoacetate, η, η-dimethylpropanamide, dimethyl malonate, diethyl sulfoxide, 2- (2-methoxyethoxy) ethanol, trimethyl phosphate, diethyl malonate; in particular said organic extractant is selected from the group consisting propanone, methylacetate, ethylacetate, butanone, dioxane, trimethoxymethane, 1,3-dioxane, 1,3,5-trioxane, 1,2-diaminoethane, l-methoxy -2- propanol ..

17. An azeotropic composition or quasi-azeotropic comprising 45-65 mol% of 2- chloro-3,3,3-trifluoropropene (1233xf) and 35 to 55 mole% of 1,1,1,3,3-pentafluoropropane (245fa ) based on the total composition.

18. A composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf), El-chloro-3,3,3-trifluoro-l-propene (1233zdE) and an organic extractant having a separation factor If 2 greater than or equal to 1.6, said separation factor is calculated by the formula Si, 2 = (yi, s * PI) / (y2, s * P2) wherein yi, s represents the coefficient of activity 2-chloro-3,3,3-trifluoropropene (1233xf) in said organic extractant at infinite dilution, PI represents the saturation vapor pressure of 2-chloro-3,3,3-trifluoropropene (1233xf), y2 , s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE) in said organic extractant at infinite dilution, P2 represents the saturation vapor pressure of the El-chloro- 3,3,3-trifluoro-l-propene (1233zdE), preferably said organic extractant has a C2 absorbency, s greater than or equal to 1.0, said absorptive capacity is calculated by the formula C2, s = / (Y2, s) wherein y2, s is the activity coefficient of the El-chloro-3,3,3-trifluoro-l-propene (1233zdE) in said organic extractant at infinite dilution; preferably said organic extractant is selected from the group consisting of isopropylmethylamine, methyl-t-butylether, diethylamine, propanone, methyl acetate, 2-butanamine, n-methylpropylamine, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate , -dimethoxypropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, l-methoxy-2-propanamine, 2-methoxyethanamine, tert-butylacetate, ethylpropionate, 1,2-dimethoxypropane, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butyl acetate, n-methyl-l, 2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl- 5-heptenal, l- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 2-ethylbutylamine, diethyl carbonate, n-butylacetate, 2-hexanone, n-and hylethylenediamine, 2-methoxyl-propanol, l-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2- ethoxy-l-propanol, 1-methylpiperazine, 1,3-propanediamine, 2-heptanamine, η, η-diethylethylenediamine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-l, 2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-Propoxyethanol, l-propoxy-2-propanol, 2-heptanone, dimethylformamide, 2-isopropoxyethanol, 2-methylpiperazine , cyclohexanone, 1-heptanamine, 2-ethoxyethanolacetate, 1,4-butanediamine, 2,4-dimethylpyridine, 2-methoxy-3-methylpyrazine, 4-methoxy-4-methyl-2-pentanone, 3-ethoxy-l propanol, 3-methoxy-1-butanol, diglyme, 2- (diethylamino) -ethanol, 2,2-diethoxyethanamine, 2-methoxy-N-

(2-methoxyethyl)ethanamine, 2-(ethylamino)ethanol, 3-octanone, diacetone alcohol, diethylaminopropylamine, 2-ethylhexylamine, l-butoxy-2-propanol, 2-butoxyethanol, 2-octanone, methylheptanoate, triethylenediamine, n,n-dimethylpropanamide, 2-propanol-l-methoxy-propanoate, 1,5-pentanediamine, cycloheptanone, 3,4-dimethylpyridine, 1-octanamine, benzylmethylamine, 1,1,3,3-tetramethoxypropane, dihexylphthalate, diethylpropanolamine, 2-butoxyethanolacetate, diethylsulfoxide, 2-(2-methoxyethoxy)ethanol, 4-methylbenzenemethanamine, diethyleneglycolmonoethylether, 2-propylcyclohexanone, trimethylphosphate, 2-methyl-2,4-pentanediol, methylbenzoate, diethylmalonate, 2-methoxypyrimidine ; en particulier ledit agent d'extraction organique est choisi parmi le groupe consistant en diethylamine, propanone, methylacetate, tetrahydrofurane, ethylacetate, butanone, diethoxymethane, isopropylacetate, tert-butylacetate, dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy2-propanol, n-butylacetate, l-ethoxy-2-propanol.