DEVICE AND METHOD FOR WATER DESALINATION DEIONIZATION

THERMAL FLUID EXTRACTION IONIC LIQUID PHASE

Technical Field of the Invention

The technical field of the invention is the ionic extraction applied to desalination, particularly seawater.

BACKGROUND

The current approach to desalination of sea water includes the extraction of water from salt water. It comprises the evaporation / condensation technologies water by natural or forced heating at ambient pressure or under vacuum and the use of semipermeable membranes (nanofiltration, reverse osmosis ...). Whatever the technology, this approach combines the following drawbacks and shortcomings:

1. A limited water recovery level of the fact that beyond 53% water extracting a running sea water, there is scaling of equipment by precipitation of CaC0 3 , then CaS0 4 or Mg (OH) 2 and other salts of low relative solubilities contained in residual water. If the technology is associated with a thermal vaporization of the water, the use temperature, usually above 80 ° C is then generating a lower threshold precipitation of certain salts (e.g. CaC0 3 by evaporation dioxide atoms) and the inverted solubility salts (CaS0 4 in water), which further limits the maximum extraction water level of salt water to not reach while 30-35% .

2. An energy intensive procedure. Since water is a large majority (in% by mass and% mol) with respect to the dissolved ions, extracting water from the brine returns to move a large amount of material which is not thermodynamically favorable. Thus, the vaporization of water is extremely costly in energy (its latent heat of vaporization is 2319 kJ / kg at 75 ° C. This is equivalent to burn 74.6 ml of gasoline per liter of water spray then a standard sea water contains only 36 g of salt per kg of sea water. Thus, in order to reduce the thermal energy consumed, there has been developed technology to multiple or successive pressure effects using sub tanks vacuum to reduce the thermal energy consumed to an order of magnitude and thus reach down to 230 kJ / kg with 12 effects associated with an investment surplus. Similarly, membrane permeation or reverse osmosis (representing more than 90 % new capacity installed in 2011) the electrical energy consumed is between 3.5 and 4.5

kWh / m 3 of desalinated seawater.

3. The use of stainless steel, use necessary in the operating pressures that are either much lower than atmospheric pressure (vacuum) is much higher (up to 80 bar) and high concentration of chlorides. These products are expensive, but may still corrode and releasing their metal components present on the surface, generating a water pollution with toxic metals like chromium, nickel, molybdenum, manganese and copper.

Another approach to water desalination is to extract salt from seawater. This approach is used in the desalination of low salinity water (<3-5 g / L) using electrodialysis membranes, or for ultrapure water from potable water by use of exchange resins ion. This approach is also developed to newer technology in development, based on the principle of a capacitive deionization (CDI or CapDI) applicable today only desalination of low salinity water, brackish say. The technological and economic limitations of these systems is mainly due to the transfer and / or storage of ions in the membranes, resins or electrodes. Very high storage area combined with excessively long cycle times, does not allow today to these capacitive deionization technology to be deployed in treatment of sea water and thus are limited to low salinities.

Methods of liquid-liquid extraction, also known as solvent extraction processes are now industrially used as separation technique in chemical engineering. For the separation of ionic compounds, it is today common to separate organic acidic compounds or basic, or to purify metals (Zn, Ni, Cu, Co, Cr, Mn ...) after dissolution (leaching) in water (Hydrometallurgy). This separation technique is also used for obtaining high-purity products such as salts of uranium, plutonium, cesium, strontium or rare earth salts via a liquid-liquid exchange process cations.

A very extensive bibliography exists in this area in which we can cite Article TG Levitskaia, -and al. Anal. Chem. 2003, 75, 405-412 which demonstrates that it is possible to extract the sodium hydroxide (NaOH) of an aqueous solution by use of a neutral extractant sodium, crown ether type with low lipophilic acid de-protonated to allow the formation of a hydrophobic sodium alkoxide.

[DC18C6](org) + [RCOH](org) + [Na+](aq) + [OH"](aq) <→ [RCC--Na+DC18C6](org) + H20(aq)

This paper also presents examples of extraction of NaF, NaCl, NaBr,

NaN0 3 and NaCI0 4 , 1M salinity by combining DC18C6 to 0.02M without and with seven weak acids (from the family of alcohols), present in an amount of 0.04m, all dissolved in nitrobenzene. Two of these alcohols are fluorinated aromatic alcohols having a pKa of about 8.8. The extraction rate for hydrophobic ions such as picrate, is relatively high. However, for hydrophilic anions such as chloride ion CI " , the recalculated extractions rates are between 0.06% and 0.16%, which confirms the great difficulty of extracting the hydrophilic NaCl and water little influence alcohols, at this concentration, the extraction performance.

It has already been proposed in WO 2010/086575, the use in a direct contact heat exchanger comprising a hydrophobic fluorinated liquid and phase associated with ion exchangers such as ion exchangers, fluorinated. However, the fluorinated liquid organic phase described in this application describes the use of ionic organo-fluorine compounds poorly suited to obtain high water desalination rate, for example over 50%, preferably over 70% for hydrophilic alkaline salts such as NaCl to 0.2 M at 25 ° C with a low operating cost and low energy demand.

The invention aims to remedy these disadvantages by providing a new generation of hydrophobic liquid phases having an absorption capacity sufficient ionic species dependent on the temperature to allow a low temperature extraction (e.g. at room temperature) and a hot stripping these two step having a temperature differential, ΔΤ, greater than 30 ° C, preferably 50 ° C. Other aspects of the invention relate to methods and water treatment systems for purifying water with low energy balance.

Description of the Invention

Thus, the invention especially relates to a hydrophobic organic liquid composition comprising or consisting essentially of, or consists of,

- at least a first organic compound, preferably protic, and hydrophobic whose pKa in water at 25 ° C is at least 9, preferably at least 10.5, and is preferably below the pKa of water at 25 ° C, or at least less than 15 at 25 ° C, and

- at least one second organic hydrophobic compound having a complexing constant of a cationic species, the value of Log K, in methanol at 25 ° C is greater than 2 and less than 11, preferably greater than 3 and less than 9.

The first compound is a compound capable of solvating an anionic species, which is designated by the acronym MSA (for solvating molecule Anion). The second compound is a compound for extracting (e.g., solvate or chelating) a cationic species which is designated by the acronym MEC (for extractant molecule Cation). Surprisingly the combination of MSA and MEC according to the invention allows the extraction (or solvation) of cations and more particularly of hydrophilic anions particularly difficult to transfer to an organic phase.

The terms "anionic species" and "cationic species" are respectively equivalent to the term "anion" and "cation".

The pKa (or acidity constant) is defined as pKa = -log 10 Ka, where Ka is the acid dissociation constant that is measured in a standard manner for such pKa. The standard recommended measurement methodology for high pK, basic, is preferably one described by Popov et al IUPAC - Guidelines for NMR measurements for determination of high and low pK Pure Appl.Chem., Vol. 78, No. 3, pp 663_675 2006.

K is the constant of complexation of MEC and a cation in methanol at 25 ° C, which is measured according to the standard method of isothermal titration calorimetry.

By the term "hydrophobic" is meant a compound or a mixture of compounds whose solubility in water at 25 ° C, is at least less than 0.1 mol / liter. Preferably it is selected hydrophobic compounds whose solubility in water at 25 ° C is less than 0.01 mol / L, preferably less than 0.0001 mol / L and preferably less than 1x10 "5 Mol / L . the hydrophobicity or solubility of a compound can be measured by standard methods and in particular by UV-visible spectrometry methods.

The pKa of the first compound is preferably greater than 9, preferably greater than 10.5, preferably greater than 12, preferably greater than 13 and less than 15.

Alternatively, the pKa of the first compound is selected from a range from 12 to 15, preferably 13 to 14. pKa range of from 12 to 15 are defined as pKa 12.1; 12.2; 12.3; 12.4; 12.5; 12.6; 12.7; 12.8; 12.9; 13.0; 13.1; 13.2; 13.3; 13.4; 13.5; 13.6; 13.7; 13.8; 13.9; 14.0; 14.1; 14.2; 14.3; 14.4; 14.5; 14.6; 14.7; 14.8; 14.9 or 15.0.

According to a preferred aspect, the second compound, allowing the extraction, in the composition, of at least one cation, has a Log K complexing constant for said cation from 4 to 8, preferably from 5 to 7. Log K ranging from 5 to 7, means 5,1; 5.2; 5.3; 5.4; 5.5; 5.6; 5.7; 5.8; 5.9; 6.0; 6.1; 6.2; 6.3; 6.4; 6.5; 6,6; 6.7; 6.8; 6.9 or 7.0.

Advantageously, said second compound also has a complexing constant for sodium in water at 25 ° C, greater than or equal to 1.

The invention also relates to a composition comprising at least one MSA, at least one MEK and, optionally, a plasticizer. MSA compounds and MEC are as described above and / or below.

compound MSA

MSA a compound as described herein, mixtures thereof and uses in a method of extracting at least one anionic species of water containing said species are also part of the invention.

MSA may be a compound containing from 6 to 50 carbon atoms, preferably from 7 to 30 carbon atoms, and especially from 8 to 20 carbon atoms, and including at least one aromatic ring and at least one halogen atom or an electron withdrawing group, in particular fluorinated.

Advantageously, the MSA is a compound of formula B:

wherein at least any one of R A , RB, RC, RD and R E , equal or different, is a halogen atom or an electron-withdrawing group, in particular a halogenated group, the following group:

- F, Cl, Br,

C m F 2m + i with m≤ 4, wherein m is a non-zero integer,

CF 2 CF2CpH2p + i with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- CH 2 cpf 2 p + i with p ≤ 4, where p is an integer,

- OCH 2 the CF 3 ,

- C(=0)CF3,

- C m H n F p Cl q Br s with m≤ 4, wherein n, p, q, s are integers which at least p, q or s is not zero,

- C (= 0) OC m H 2m + 1 with m≤ 4, wherein m is an integer, and

- C (= 0) C m H 2m + 1 with m≤ 4, wherein m is an integer,

or the radicals R A , R B , R C . R D and R E remaining (s) are chosen, which are identical or different, from the following non-electron-withdrawing radicals:

- H,

- CH The 3 ,

- CH 2 CH 2 C p F 2p + i with p ≤ 4, where p is an integer,

- C m H 2m -i with m≤ 10, wherein m is a nonzero integer, and

- C m H 2m + i m <10, where m is a non-zero integer; where one of R A to R E can be one of these two latter radicals C m H 2m-1 and C m H 2m + 1;

and wherein X is selected from the following radicals:

OH

/

C— R'

"

or R 'and R ", identical or different, are chosen from the following radicals:

- H,

- C n H 2n i n <4, where n is a nonzero integer,

- C n H 2n + 1 with n <4, where n is a nonzero integer,

- CH 2 CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

- CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- C m F 2m + 1 with m≤ 4, wherein m is a non-zero integer,

- C m H n F p Cl q Br s with m≤ 4, wherein n, p, q, s are integers which at least p, q or s is not zero,

and an aryl radical of the formula b

(b)

where R A , RB, RC. R and RD EL identical or different, are as previously defined in formula B;

and wherein R ' "is selected from the following radicals:

- C m H 2m + i with m≤ 20 of préférence≤ 15, wherein m is an integer,

- C m H 2m -i with m≤ 20, wherein m is a non-zero integer,

- C m H n F p Cl q Br s m <10, wherein n, p, q, s are integers which at least p, q or s is not zero,

- CH 2 CH2CpF 2 p + i with p ≤ 4, where p is an integer,

- CH 2 C p F2p + i with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + i with p ≤ 4, where m is an integer,

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where m is an integer,

- C m F 2m + 1 with m≤ 4, wherein m is a non-zero integer,

- and an aryl radical of the formula b:

(b)

wherein R A , RB > RC, RD and R E , equal or different, are as previously defined for formula B.

Composed M SA - alcohol

Such a compound is advantageously chosen from the group of fluorinated aromatic alcohols. For example, this compound may be a phenol derivative such as 3- (trifluoromethyl) phenol (CAS: 98-17-9).

Preferably, the first compound is a compound methanolic phenyl which advantageously comprises more than 3 fluorine atoms. Advantageously, this compound has more than two radicals -CF 3 .

According to one embodiment of the invention the first compound is a compound of formula A:

in which

Ri, R2, R 3, R 4 and R 5 , identical or different, but where any one of R 2 and R 3 is a fluorinated radical, are chosen from the following radicals:

- H,

- F,

- C m F 2m + i with m≤ 4, wherein m is a non-zero integer,

- CF 2 CpH 2 p + i with p ≤ 4, where p is a nonzero integer, and

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where p is a non-zero integer;

and wherein R 'and R ", identical or different, are chosen from the following radicals:

- H

- C n H 2n i n <4, where n is a nonzero integer,

- C n H 2n + i with n <4, where n is a nonzero integer,

- CH 2 C p F 2p + i where p ≤ 2, where p is a nonzero integer,

- CH 2 CH 2 C p F 2p + 1 where p ≤ 2, where p is a nonzero integer,

- and an aryl radical of formula a:

where RL R 2L R 3L R 4 and R 5 , identical or different, are selected from the group

- H

- F

- C m F 2m + 1 with m <4 ,.

- CF 2 C p H 2p + 1 with p ≤ 4, where p is a nonzero integer,

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where p is a nonzero integer.

Preferably said first compound is selected from the group consisting of the compounds described in the following Table I:

Tableau I :

Formula weight [MSA] Solubility

MSA Formula semi Density

No gross maximum molar ° to the developed pKa water (g / cm3)

CAS (g / mole) Mole / L mmol / L

C15H10F6O 1 ,37 13,3

320.23 +/- 4.28 0.07 1 0 1598-89-6 Liquid (estimated)

and two compounds MSA, MSA MSA 3 and 5 described below.

According to one aspect of the invention, the hydrophobic organic liquid composition comprises at least two compounds for the solvation of at least one anion. Preferably these compounds are selected from compounds of type (MSA) described in the present application.

In particular, the liquid composition according to the invention may comprise a mixture of [3- (Trifluoromethyl) phenyl] methanol (CAS: 349-75-7) and [3,5-bis (trifluoromethyl) phenyl] methanol ( CAS #: 32707-89-4). The volume relative proportion of these compounds relative to each other may vary, but is preferably in a ratio ranging from 30/70 to 50/50 volume / volume (v / v). Preferably this ratio is about 40/60 v / v.

Alternatively, the liquid composition according to the invention may comprise a mixture of 3- (perfluorobutyl) phenyl] methanol (MSA 5) and 3,5 (perfluoropropyl) phenyl] methanol (MSA 6). The relative proportion of these compounds relative to each other may vary, but is preferably in a ratio ranging from 60/40 to 80/20 v / v. Preferably this ratio is about 70/30 v / v.

Compound MSA - amide

The MSA compound of formula B may also be an amide compound. In this case the radical X in formula B is:

where R ' "is as previously described.

Reference the amide is of the formula:

the following radicals:

- -C m H 2m + i m <20, preferably <15 where m is an integer,

- -CmH 2m -i m <20, where m is a non-zero integer,

- -C m H n F p Cl q Br s with m≤ 10, wherein n, p, q, s are integers which at least p, q or s is not zero,

- and an aryl radical of the formula b:

wherein at least any one of R A , RB. RC, RD and R E , equal or different, is a halogen atom or an electron-withdrawing group, in particular a halogenated group, the following group:

- F, Cl, Br,

C m F 2m + i m <4, where m is a non-zero integer,

- CF 2 CF 2 CpH 2 p + i with p ≤ 4, where p is an integer,

CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- CH 2 cpf 2 p + i with p ≤ 4, where p is an integer,

- C(=0)CF3,

- C m H n F p Cl q Br s m <4, where n, p, q, s are integers which at least p, q or s is not zero,

- C (= 0) OC m H 2m + 1 with m <4, where m is an integer, and

- C (= 0) C m H 2m + 1 with m <4, where m is an integer,

or the radicals R A , RB, RC, RD and R E remaining (s) are chosen, which are identical or different, from the following non-electron-withdrawing radicals:

- H,

- CH The 3 ,

- CH 2 CH2CpF 2 p + i with p ≤ 4, where p is an integer,

- C m H 2m -i with m≤ 10, wherein m is a nonzero integer, and

- C m H 2m + i with m≤ 10, wherein m is a non-zero integer,

where one of R A to R E can be one of these two latter radicals C m H 2m-1 and

Preferably the radical R " 'is an alkyl chain, linear or not, and in particular a radical nC 7 H 15 , nC 9 H 19 , n-C n H 23 or nC 13 H 27 .

These amide compounds are particularly suited to the extraction process by temperature difference according to the invention. Other compounds of this type that can be used as MSA for extraction compositions according to the invention are for example:

N- [3,5-Bis (trifluoromethyl) phenyl] acetamide (CAS No. 16143-84-3),

N- [3,5-Bis (trifluoromethyl) phenyl] -2-chloroacetamide (CAS # 790-75-0), N- [3,5-Bis (trifluoromethyl) phenyl] -2-bromoacetamide (CAS 99468 -72-1), N- [3,5-Bis (trifluoromethyl) phenyl] -2-chlorobenzamide (CAS No. 56661-47-3), N- [3,5-Bis (trifluoromethyl) phenyl] -4 -chlorobenzamide (CAS No. 56661-30-4), N- [3,5-Bis (trifluoromethyl) phenyl] -4-bromobenzamide (CAS No. 56661-31-5), N- [3,5-dichlorophenyl] acetamide (CAS No. 31592-84-4),

N- [4-methyl-3,5-dichlorophenyl] acetamide (CAS No. 39182-94-0),

N- [3-fluoro-5- (trifluoromethyl) phenyl] acetamide (CAS 402-02-8), N- [2-fluoro-5- (trifluoromethyl) phenyl] acetamide (CAS 349-27 -9), N- [4-chloro-3- (trifluoromethyl) phenyl] acetamide (CAS 348-90-3), N- [4-bromo-3- (trifluoromethyl) phenyl] acetamide (No. 41513-05-7 CAS), N- [2,5-difluoro-3- (trifluoromethyl) phenyl] acetamide (CAS 1994-23-6), N- [3- (trifluoromethyl) phenyl] acetamide ( CAS 351-36-0)

N- [2-methyl-3- (trifluoromethyl) phenyl] acetamide (CAS No. 546434-38-2), N- [2-amino-3- (trifluoromethyl) phenyl] acetamide (CAS 1579-89 -1), N- [3- (trifluoromethyl) phenyl] -2,2,2-trifluoroacetamide (CAS No. 2946-73-8), N- [3- (trifluoromethyl) phenyl] -2,2 dichloroacetamide (CAS No. 2837-61-8), N- [3- (trifluoromethyl) phenyl] -2,2,2-trichloroacetamide (CAS 1939-29-3), N- [4-chloro- 3- (trifluoromethyl) phenyl] -2,2,2-trichloroacetamide (CAS No. 13692-04-1),

N- [3- (trifluoromethyl) phenyl] -2-bromoacetamide (CAS No. 25625-57-4),

N- [3- (trifluoromethyl) phenyl] propanamide (CAS No. 2300-88-1),

N- [2-chloro-5- (trifluoromethyl) phenyl] propanamide (CAS No. 721-57-3), N- [3- (trifluoromethyl) phenyl] (2,2-dimethyl-propanamide) (No. CAS 1939-19-1), N- [2-methyl-3- (trifluoromethyl) phenyl] (2,2-dimethyl-propanamide) (CAS No. 150783-50-9),

le N-[4-chloro-2-methyl-3-(trifluoro

(112641-23-3 CAS),

N- [3- (trifluoromethyl) phenyl] (2-chloro-propanamide) (CAS 36040-85-4), N- [3- (trifluoromethyl) phenyl] butanamide (CAS 2339-19-7 )

N- [3- (trifluoromethyl) phenyl] isobutanamide (CAS 1939-27-1),

N- [3- (Trifluoromethyl) phenyl] cyclopentanecarboxamide. (CAS no. 13691-84-4), N- [3- (trifluoromethyl) phenyl] (2-methyl-pentanamide) (CAS # 1939-26-0 ), N- [3- (trifluoromethyl) phenyl] (2,2-Dimethyl-pentanamide) (CAS No. 2300-87-0), N- [3- (trifluoromethyl) phenyl] (2- (4-Brornophényl ) acetamide) (CAS 349420- 02-6)

N- [3- (Trifluoromethyl) phenyl] -1-adamantanecarboxarnide (CAS No. 42600-84- 0),

N- [2-chloro-5- (trifluoromethyl) phenyl] octanamide (CAS # 4456-59-1).

These molecules, employed as MSA, by integrating them in a formulation combining at least one MEK and optionally a diluent, allow the extraction of ionic species and in particular of hydrophilic water salts to the extracting organic phase.

Another object of the invention concerns the use of MSA and MSA in particular amide compounds to the salt water desalination and / or for extraction of salts and / or ions from an aqueous medium. In particular these compounds may be used individually or in mixture, in a composition or in a method according to the invention as described in the present application.

MSA concentration in the organic liquid composition

According to a preferred aspect of the invention the molar concentration of the first compound MSA (or mixture thereof) in the composition according to the invention is at least 0.1 M. Preferably this composition is higher, and is at least equal to 1 M so as to enable an optimized extraction particularly hydrophilic anions. It may also be at least equal to 2 M, preferably at least equal to 3 M, for example at least equal to 4 M. In some embodiments of the invention, the first compound, or a mixture of first compounds, can be used pure (molar concentration of 7.32 M for the CAS No. 349-75-7).

Density and solubility and viscosity

According to an advantageous aspect of the invention, the first compound for solvation in the composition, of at least one anion has a solubility in water, in its free form or complexed less than 0.1 Mol / L , preferably less than 0.01 Mol / L, preferably less than 0.0001 mol / L and more preferably less than 1x10 "5 mol / L.

According to another advantageous aspect of the invention, the first compound for solvation in the composition, of at least one anion has a density greater than 1, 1 kg / L, ideally greater than 1, 2 kg / Liter.

According to yet another advantageous aspect of the invention, the first compound for solvation in the composition of at least one anion has a viscosity at 25 ° C of less than 100 mPa.s, preferably less than 50 mPa .s, for example less than 20 mPa.s.

GUY

The second compound, which allows the at least one cation extraction (MEC), may advantageously be selected from molecules having a good capacity for extraction of the alkali ions such as sodium ions and / or alkaline ions earthy or other cations according to the need for separation. The extraction can be due to replacement of the solvation of cations and anions through the water by a solvation thereof by the extracting composition which then allows an interaction with CME and MSA. The nature of interactions covers such phenomena as ion-dipole interactions, accompanied by the establishment of hydrogen bonds and électrostiques interactions or van der Waals bonds. Preferably the ECM is a compound capable of complexing, and in particular of chelating cation. The "Chelate" differs from the simple "complex" in that the cation is attached to the chelating ligand by at least two links / interactions.

The second compound may advantageously be selected from the group of nonionic compounds (or neutral) and / or non-fluorinated. The use of a crown ether having a carbon number ranging from 14 to 80, in particular non fluorinated crown ethers can be considered.

By crown ether cyclic molecule is meant having a carbon number ranging from 14 to 80, crown is meant the ether having 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79 or 80 carbon atoms.

Thus, the second compound may be selected from the group consisting of DB21 C7, B15C5, C15C5, DC18C6, DB18C6, DB24C8, Calix [4] is, and substituted calixarene

other than the Calix [4] East. The formula of these compounds are indicated below.

The second compound is preferably a substituted calixarene may include, for example, from 32 to 80 carbon atoms, more particularly from 50 to 70 atoms, for example from 58 to 60 carbon cabones. 4-tert-butylcalix [4] arene-0,0 , , 0, "0" , -tetraacetic Acid Tetraethyl Ester is particularly preferred for the extraction of sodium.

The composition according to the invention may also comprise more than one compound for the extraction of at least one cation, the latter can advantageously be selected from the compounds described in the present application.

Density and solubility and viscosity

According to a preferred aspect of the invention, the second compound allowing the extraction, in the composition, of at least one cation has a solubility in water, in its free form or complexed with the cation of less than 0.1 Mol / L, preferably less than 0.01 Mol / L, preferably less than 0.0001 mol / L and more preferably less than 1x10 "5 mol / L.

According to another preferred aspect of the invention, the second compound allowing the extraction, in the composition, of at least one cation has a solubility in the first compound (MSA) at 25 ° C greater than 0.2 M / L, preferably greater than 0.5 M / L, for example more than 1 M / L.

According to another preferred aspect of the invention, the second compound allowing the extraction, in the composition, of at least one cation having a density greater than 0.8 kg / L, preferably greater than 1, 0 kg / L , ideally greater than 1, 2 kg / L. According to another preferred aspect of the invention, the second compound allowing the extraction liquid in the at least one cation is a liquid and has a viscosity at 25 ° C of less than 100 mPa.s, preferably less than 50 mPa.s, for example less than 20 mPa.s.

relative concentration of MSA and MEC in the organic liquid composition

To ensure maximum extraction of ionic species, concentrations of MSA and MEC are chosen depending on the concentration in the aqueous solution of the ionic species to be extracted.

Thus at constant volume of salt water and extraction formulation, MEC compound concentration is advantageously equimolar to or greater than the concentration of the cation to be extracted. Near a concentration twice generally a boundary beyond which the extraction of cations is not substantially improved.

Surprisingly a molar concentration of MSA much higher than that

of the anion to be extracted can be required to perform an optimized extraction. And at least twice, preferably four times, see the quintuple or sextuple, see, concentration of the anion to be extracted may be necessary to obtain satisfactory results, particularly when the anion is the anion chloride.

Thus the relative proportion of molar MSA / MEC of a composition according to the invention for extracting a salt consisting of an anion and a cation is advantageously greater than or equal to 1, 2, 3, 4, 5 or 6. The choice of molar ratio relative MSA / MEC to remember for industrial application is dependent on the relative cost of these compounds and the technical and economic data of the project. Preferably this proportion is at least 4 for a MSA alcohol and between 1 and 4 for a MSAAmide.

Use of the composition according to the invention

The composition according to the invention can advantageously be used for extracting ions (cations, anions) an aqueous hydrophilic phase. It should be noted that this ion extraction is not offset by the transfer of chemical species, ionic or otherwise, from the organic phase to the aqueous phase. This composition is particularly suitable for the extraction of ionic species present in salt water, particularly seawater. Also, this composition can advantageously be used for desalination of sea water and usually purification or treatment of salt water. By "salt" refers to water comprising at least one salt. By "salt" means an ionic compound composed of cations and anions and forming a neutral product with no net charge. These ions can be both inorganic (CI chloride " , Na ion + ...), and organic (acetate CH 3 -COO " , ammonium R 3 NH + ...) and monatomic fluoride (F " , ion Mg 2 + ...) as well as polyhydric (nitrates N0 3 " , hydrogen HC0 3 " , sulfate S0 4 2 " ...).

The composition according to the invention is therefore particularly suitable for use in a method or an ion extraction device according to any of the other objects of the invention described in this application.

Anions and cations to extract

The first and second compounds within the composition according to the invention are compounds allowing the solvation and extraction of at least one, and preferably several, ionic species constituting alkali or alkaline earth salts. In particular, these ionic species are those present in seawater and are listed and their respective concentrations in Table II.

Tableau II:

Also the compositions of the invention may be used in methods according to the invention to extract into an organic phase on Na + or K + or a mixture of Na + and K + . Preferably, the anion solvated by the composition of the invention is a hydrophilic anion, such as Cl " or S0 4 2" or HC0 3 " or a mixture of Cl " and S0 4 2 " . Thus the composition according to the invention is particularly suitable for the extraction of an aqueous phase of NaCl, Na 2 S0 4 , of NaHC0 3 , KCl, K 2 S0 4 or KHC0 3 , or extraction a mixture of NaCl and Na 2 S0 4 , NaCl and NaHC0 3 , NaCl and KCl, NaCl and K 2 S0 4 or NaCl and KHCO 3 , or any mixtures of these salts, or a mixture of NaCl and Na 2 S0 4 and NaHC0 3 and KCl and K 2 S0 4 and KHC0 3 .

Alternatively, or additionally, the extracted anions are fluorides, bromides, HC0 3 " , nitrates N0 3 " , CN " , OH " , nitrites N0 2 " , carbonates C0 3 2" , or CI0 2 " or sulfite S0 3 2 " or other.

For the more hydrophobic anions such as perchlorates CI0 4 " , permanganates Mn0 4 " , the picrates, lower concentrations of MSA sufficient to effect transfer to the organic phase in combination with at least one cation complexed with an ECM.

thinning

Some of MEC and MSA being solid or viscous compounds at operating temperatures of the extraction process, the use of a plasticizer is then advantageous. Since the method according to the invention allows in particular to extract relatively high concentrations of salts, identify solubilizer capable of dissolving at least 0.1 mol / L of MEC and MSA, cumulative, must be identified. Indeed, conventional solvents such as acetone, ethyl acetate, heptane, dimethyl formamide, nitromethane, methanol, ethanol, diethyl ether or acetonitrile, for example do not solubilize at these levels concentration number MEC known and especially Calix [4] ester, which is a MEC of interest.

By cons, it appears that solvents such as chloroform and particularly polar aromatic solvents have the ability to be good candidates as solubilizing for this application. This can be explained by the similar nature of the MSA, themselves generally aromatic compounds. For example, the 1, 3-bis (trifluoromethyl) benzene (CAS: 402-31-3) and more preferably the benzyl benzoate (CAS: 120-51-4) composed of two aromatic rings meet this criterion solubilization of the tested formulations incorporating Calix [4] Ester and MSA3. Thus the presence of at least one electron withdrawing trifluoromethyl group on an aromatic or 2 aromatic rings allow to obtain compounds fluidizing particularly advantageous.

According to a preferred aspect of the invention, the composition is composed only of MEC and MSA compounds, and optionally in combination with a compound thus constituting plasticizer a composition consisting of MSA and MEC and a plasticizer compound.

In a preferred aspect of the invention, the composition does not include compounds classified as hazardous and shows no effect of skin irritation, is not allergenic and has no acute oral toxicity.

Preferably the composition according to the invention does not contain nitrobenzene. Preferably the composition according to the invention comprises a fluorinated aromatic compound containing more than 3 fluorine atoms and a MEC having a complexing constant in methanol at 25 ° C of between 3 and 9. The MEC can be e.g. Ether crown, a cryptand Calixarene or functionalized, as for example Cali [4] Ester.

Another object of the invention relates to the compound 3- (perfluorobutyl) phenyl] methanol.

Still another object of the invention relates to the compound 3,5 (perfluoropropyl) phenyl] methanol.

The invention further relates to a composition comprising, consisting essentially of or consists of, a mixture of 3- (perfluorobutyl) phenyl] methanol and 3,5 (perfluoropropyl) phenyl] methanol

These two compounds are new, as is the composition comprising them. Another object of the invention relates to the use of 3-

(Perfluorobutyl) phenyl] methanol and / or 3,5- (perfluoropropyl) phenyl] methanol, alone or in mixture, for desalination of salt water and / or for extraction of salts and / or ions an aqueous medium. In particular these compounds may be used individually or in mixture, in a composition or in a method according the invention as disclosed in the present application.

In a preferred embodiment the composition does not comprise MEC for the extraction of calcium ions.

The invention also relates to a water processing method comprising extracting at least two ionic species, said ionic species comprising an anionic species and a cationic species and being present in water to be treated, said method comprising the following steps:

a) mixing in a first reactor at a first temperature between a liquid hydrophobic organic phase and the water to be treated, said water to be treated being in the liquid state, for the subsequent obtaining of a liquid treated water and a hydrophobic liquid organic phase containing said ionic species,

said hydrophobic phase comprising a first and a second hydrophobic compound as described herein and in particular:

a first organic compound, preferably protic, and hydrophobic whose pKa in water at 25 ° C is at least 9, preferably 10.5 and is preferably below the pKa of water at 25 ° C, or at least below 15 to 25 ° C, and

and a second organic compound having a hydrophobic complexing constant whose value Log K, in methanol at 25 ° C, is greater than 2 and less than 11, preferably greater than 3 and less than 9;

b) separating on the one hand, of said treated liquid water and the other of said liquid organic phase containing said ionic species,

c) mixing, at a second temperature, in the liquid phase in a second reactor of said liquid organic phase charged ionic species and regeneration of liquid water, for the subsequent obtaining of a regenerated liquid organic phase and liquid regeneration water loaded with ionic species, the difference between said first and second temperatures ranging from 30 ° C to 150 ° C.

Alternatively the invention also relates to a method as described above but where the first organic compound is a MSA and the second organic compound is a MEK. According to another variant of the invention, the method is as described above but the first and second organic compounds are included in a composition according to the invention extradante.

Unlike many already known extraction processes, the process according to the invention is not based on a pH change to allow either the absorption or release of the captured ions, especially via an acid-base mobility the hydrogen ion H + . Thus a preferred aspect of the invention is that the method does not include a step wherein the pH of liquid regeneration water is significantly altered, that is to say beyond a pH change of + / - 2, for example of ± 1 with respect to water to be treated.

The method being especially suitable for desalination of sea water, considered ionic species may be one of those described in Table II above. Moreover, this process advantageously allows to extract from the water to be treated, at least one alkaline or alkaline cationic species and anionic species such as CI ions " or S0 4 2" . It should be noted that such anionic species are hydrophilic and particularly difficult to extract from aqueous media. A particularly advantageous aspect of the method according to the invention is that it can enable the extraction of an aqueous phase of Na + , Cl " , S0 4 2" , and K + simultaneously.

ETAPE a)

The mixing step a) water to be treated and the organic phase may be effected by stirring the two liquid phases, for example by rotation, centrifugation, and / or interpenetration vertical (gravity column) when the two phases are of different densities. The latter is what is preferred. Also, the organic phase is preferably chosen as having a higher density than the density of water to be treated and treated water. Alternatively, the organic phase can be chosen to have a lower density than the density of water to be treated and treated water. In both cases, the density differential sufficient to allow effective interpenetration of the two phases when this type of mixture is used. In this case, this difference is preferably at least 0.1 kg / L. However, if other mixtures of means are used, such as centrifugation, then this differential may be only at least 0.05 kg / L.

It is also preferred that the mixture of step a) does not take place under conditions which result in a microemulsion or in a stable emulsion.

ETAPE b)

The step of separating the aqueous and organic phases may advantageously be a simple gravitational decantation of the organic phase and the aqueous liquid phase. This settling can take place in the reactor where the mixture is carried out. Alternatively the separation may be achieved by applying an external means, e.g., centrifugation, optionally in a separate centrifuge reactor where applicable the mixture of the aqueous and organic phases.

Step c)

After the phases separated, the organic liquid phase containing species

ion is directed to the second reactor where it is contacted with liquid water, where regeneration water. With the exception of temperature, this mixture of step c) may be carried out under similar operating conditions to those described for the mixture of step a). However, some conditions such as pressure, may vary for example to avoid a boiling up of water or plasticizer.

TEMPERATURE

According to a particularly advantageous aspect of the invention, step a) is performed at room temperature. It is also advantageous that the water to be treated is not subjected to a step of heating or pre-cooling. Alternatively, a step of heating or pre-cooling can take place. In this case it is preferable that water to be treated is heated or cooled by more than 5 ° C, preferably more than 2 ° C, relative to the water to be treated unheated or uncooled.

According to another advantageous aspect of the invention, the first temperature is at a temperature below 50 ° C but preferably above 0 ° C. This temperature can be chosen within ranges of from 10 ° C to 40 ° C, preferably 15 ° C to 30 ° C, and particularly 19 to 26 ° C (eg 25 ° C).

For temperature range from 10 ° C to 50 ° C is meant temperatures of 10 ° C, 11 ° C, 12 ° C, 13 ° C, 14 ° C, 15 ° C, 16 ° C, 17 ° C , 18 ° C, 19 ° C, 20 ° C, 21 ° C, 22 ° C, 23 ° C, 24 ° C, 25 ° C, 26 ° C, 27 ° C, 28 ° C, 29 ° C, 30 ° C, 31 ° C, 32 ° C, 33 ° C, 34 ° C, 35 ° C, 36 ° C, 37 ° C, 38 ° C, 39 ° C, 40 ° C, 41 ° C, 42 ° C , 43 ° C, 44 ° C, 45 ° C, 46 ° C, 47 ° C, 48 ° C, 49 ° C or 50 ° C.

According to another advantageous aspect of the invention the second temperature is a temperature above 50 ° C, preferably above 70 ° C. This temperature can be chosen within ranges of from 50 ° C to 150 ° C, preferably 70 ° C to 110 ° C, particularly 80 ° C to 90 ° C (e.g. 85 ° C).

For temperature range from 50 ° C to 150 ° C is meant temperatures of 50 ° C, 51 ° C, 52 ° C, 53 ° C, 54 ° C, 55 ° C, 56 ° C, 57 ° C , 58 ° C, 59 ° C, 60 ° C, 61 ° C, 62 ° C, 63 ° C, 64 ° C, 65 ° C, 66 ° C, 67 ° C, 68 ° C, 69 ° C, 70 ° C, 71 ° C, 72 ° C, 73 ° C, 74 ° C, 75 ° C, 76 ° C, 77 ° C, 78 ° C, 79 ° C, 80 ° C, 81 ° C, 82 ° C , 83 ° C, 84 ° C, 85 ° C, 86 ° C, 87 ° C, 88 ° C, 89 ° C, 90 ° C, 91 ° C, 92 ° C, 93 ° C, 94 ° C, 95 ° C, 96 ° C, 97 ° C, 98 ° C, 99 ° C, 100 ° C, 101 ° C, 102 ° C, 103 ° C, 104 ° C, 105 ° C, 106 ° C, 107 ° C , 108 ° C, 109 ° C, 110 ° C, 111 ° C, 112 ° C, 113 ° C, 114 ° C, 115 ° C, 116 ° C, 117 ° C, 118 ° C, 119 ° C, 120 ° C, 122 ° C, 124 ° C, 126 ° C, 128 ° C, 130 ° C, 132 ° C, 134 ° C, 136 ° C, 138 ° C, 140 ° C, 142 ° C, 144 ° C , 146 ° C, 148 ° C or 150 ° C.

The first and second temperatures are necessarily chosen so that the mixture remains in the liquid state at the operating pressure. It is particularly advantageous that the difference between these temperatures, ΔΤ, be chosen within a range from 30 ° C to 150 ° C, preferably 50 ° C to 75 ° C. By ΔΤ from 50 ° C to 75 ° C is meant a ΔΤ 50 ° C, 51 ° C, 52 ° C, 53 ° C, 54 ° C, 55 ° C, 56 ° C, 57 ° C, 58 ° C, 59 ° C, 60 ° C, 61 ° C, 62 ° C, 63 ° C, 64 ° C, 65 ° C, 66 ° C, 67 ° C, 68 ° C, 69 ° C, 70 ° C , 71 ° C, 72 ° C, 73 ° C, 74 ° C or 75 ° C. Also, if the first temperature is 20 ° C, the second temperature is over 50 ° C, preferably over 70 ° C.

Thus, the method of the invention may comprise a first step a) allowing the transfer of ionic species of the water to be treated to the organic phase at room temperature, followed by a step c) for the regeneration phase loaded organic ionic species and which occurs at a temperature above room temperature but relatively low (e.g. less than 150 ° C).

According to a preferred aspect of the method, it comprises the subsequent steps of:

d) separating said regenerated liquid organic phase and liquid regeneration water loaded in said ionic species,

e) placing in indirect thermal contact, for example by heat exchanger, said liquid organic phase charged ionic species and said regenerated liquid organic phase.

According to a particular aspect of the invention, it is advantageous that the method comprises the steps of heating and / or cooling:

- the organic phase containing ionic species,

- the organic phase, especially regenerated unloaded into ionic species,

- the water being treated,

- the treated water, and / or

- the regeneration water;

which precede the introduction of these various phases or water in the first and second reactors.

Such heating steps may be performed wholly or partly through exchange of heat between at least two of the various aforementioned phases (that is to say, the organic phases and aqueous phases such as water to be treated, the treated water and water containing ionic species (salt)).

In particular the method according to the invention comprises a regeneration of the water heating step carried out before step c).

PRESSION

The mixing steps a) and / or c) are advantageously carried out at atmospheric pressure of about 1 atm at sea level, or without pressure application means other than the weight of the liquid present in the reactor.

If pressure is applied, it can be positive or negative. Such pressure can range from 0.8 atm to 80 atm, preferably 1 to 10 atm.

USE OF TREATED WATER

Advantageously the liquid regeneration water used in step c) is a part of the treated water obtained at the end of step a). Alternatively it can be after an external source.

COMPOSITION

The organic phase comprises, or consists essentially of, or consists of the composition according to the invention that is described in the present application. This composition is particularly effective to implement said method. Compositions particularly suited for the implementation of the method according to the invention include 7 MSA and MSA 4 associated with compositions of the compounds types calixarene such as 4-tert-butylcalix [4] arene-0,0 , , 0 " , 0 " , -tetraacetic acid tetraethyl ester.

In the description of the invention, this composition can also be called "solvent" or "resin".

DEVICE

The invention also relates to a device for extracting at least two ionic species, said ionic species comprising at least one anionic species and a cationic species present in the water to be treated comprising:

- a first reactor comprising a hydrophobic organic liquid phase or composition of the invention as described in the present application.

This device may advantageously comprise:

- a first reactor comprising said hydrophobic liquid organic composition and optionally water to be treated, said water to be treated being in the liquid state, for the subsequent obtaining a treated liquid water and a hydrophobic liquid organic phase and loaded in said ionic species, said first reactor comprising in addition the first mixing means and first means for separating a part of said treated water liquid and secondly of said liquid loaded organic phase,

- a second reactor comprising a hydrophobic organic liquid phase containing ionic species and optionally liquid treated the regeneration water from said first reactor to the subsequent obtaining a liquid regeneration water charge of said ionic species and an organic phase regenerated, said second reactor comprising a second mixing means and second means for separating a part of said liquid water containing ion species

and the other of said regenerated organic phase;

-optionally of temperature control means in said second reactor;

-means for transferring communications between the first and the second reactor:

-ladite treated water regeneration liquid extracted from said first reactor

-ladite liquid charged hydrophobic organic phase withdrawn from said first reactor

-ladite regenerated liquid hydrophobic organic phase removed from said second reactor; and eventually,

-a heat exchanger bringing together the one hand said charged liquid hydrophobic organic phase withdrawn from said first reactor and secondly said regenerated liquid hydrophobic organic phase removed from said second reactor and / or said liquid water containing ionic species.

In a particular aspect of the invention, reactors, particularly those parts of the reactors that are not mobile, not stainless steel.

According to another particular aspect of the invention the first and / or second reactor does not comprise a heating means (heaters) or cooling (coolant).

According to yet another particular aspect of the invention the organic phase present in the device comprises, or consists essentially of, or consists of the composition according to the invention described in this application.

The device according to the invention may advantageously be connected in series to allow successive processing steps of the water to be treated so as to decrease the ionic species content of water to obtain a pure and / or drinking water. Such a device is also covered by the present invention.

OTHER EMBODIMENT

According to another embodiment, the invention relates to a water processing method comprising extracting at least two ionic species comprising an anionic species and a cationic species present in the water to be treated and comprising the following steps:

a) mixing in a first reactor at a first temperature between a liquid hydrophobic organic phase and the water to be treated, said water to be treated being in the liquid state, for the subsequent obtaining of a liquid treated water and a hydrophobic liquid organic phase and loaded in said ionic species,

said hydrophobic phase comprising:

a first protic and hydrophobic organic compound to the solvation

the anionic species and whose pKa in water at 25 ° C is preferably at least 11 and lower than water at 25 ° C, or at least less than 15 at 25 ° C,

and a second organic hydrophobic compound and allowing the extraction of the cationic species and advantageously having a complexing constant whose value Log K, in methanol, is greater than 2 and less than 11, preferably greater than 3 and less than 9;

b) separating a portion of said treated liquid water and the other of said liquid organic phase containing said ionic species,

c) mixture to a second temperature in the liquid phase in a second reactor of said liquid organic phase charged ionic species and regeneration of liquid water, for the subsequent obtaining of a regenerated liquid organic phase and water containing species ionic;

said organic phase charged ionic species containing only little or no calcium ions.

According to a preferred embodiment the organic phase does not comprise compounds for the extraction of calcium ions and / or divalent cations so as to enable selective extraction. As a corollary, it is also possible to use an organic phase which only allows the extraction of one or more species of divalent cations (such as calcium, magnesium, strontium, barium), and little or no cations monovalent, especially sodium.

DESCRIPTION OF FIGURES

The invention will be better understood from the appended figures, which are provided as examples and not limiting in any way, in which:

Figure 1 is a graph showing extraction rate NaCl as% salt water at various concentrations (x-axis) and temperatures (round: 20 ° C, square: 40 ° C, 60 ° C triangle and diamond: 80 ° C) using a composition MSA 4 / Calix [4] according to the invention at a concentration of 0.4M in MEC described in example 6B.

Figure 2 is a graph showing, for MSA compositions 4 / Calix [4] of Example 6B (diamond: 0.2M round: 0.4M and 0.8M triangle MEC), loading rates of PPM NaCl in% for various initial concentrations of NaCl in Mol / L at room temperature.

Figure 3 is a graph showing, in the% extraction rate of Na 2 S0 4 to a water container at different initial concentrations and at room temperature by use of a composition MSA 4 / Calix [4] Est at various concentrations (triangle: 0.2M diamond: and round 0.4M: 0.8M) according to the invention described in Example 6C.

Figure 4 is a schematic representation of an example device 7 according to the invention for implementing the method according to the invention.

Figure 5 is another schematic representation of the example of Figure 4 showing an example of operation of the various temperature of the device.

Figure 6 is a table showing the concentrations of each ion species in each of the streams identified in the Example 7 device and total salinity, density, temperature and flow rate of these flows when water to be treated is of seawater.

Figure 7 is a schematic representation of another exemplary device according to the invention described in Example 8.

Figure 8 a schematic representation of another exemplary device according to the invention described in Example 9.

Figure 9 shows the NMR spectrum of the compound MSAC11

EXAMPLES

Example 1: Description of MEC tested

Different extractive ion compositions of the invention were made and tested. The 7 MEC used in these compositions are:

7 of 10 MEC presented above were solubilized in 1 SMA, then NaCl extraction measurements were performed. The others were dissolved in 2 SMA.

Example 2: description of MSA tested

M 1: (3TFMPhOH)

3-(Trifluoromethyl)phenol

CAS: 98-17-9

The C 7 the H 5 F 3 0,

MW= 162,11 g/mole

colorless liquid

Parameter values ​​Units

Density 1, 295 kg / L

MSA 3: (35TFMBnOH)

[3,5-Bis(Trifluoromethyl)phenyl]methanol N° CAS : 32707-89-4

CgHgFeO,

MW= 244,13 g/mole

White solid.

MSA 4 = 60% vol MSA 3 + 40% voI MSA 2

White liquid, colorless.

MSA 5: (3C4F9BnOH)

[3- (perfluorobutyl) phenyl] methanol

CAS: Unknown

CnH7FgO,

MW= 326,16 g/mole

Colorless and odorless.

M SA 6 : (3,5-C3F7BnOH)

[3,5-(Perfluoropropyl)phenyl]methanol

CAS: Unknown

C l Shef O,

MW= 444,16 g/mole

In data tables above acronyms BP, MP and FP designate

BP (boiling point) = boiling point

MP (melting point) = point de fusion

FP (flash point) = flash point

example 3

The compound of formula MSA5 was synthesized as follows:

First stage

A solution of 3-iodobenzoate hydrochloride (207.9 g, 753.2 mmol, 1.0 eq.), Copper powder (239.3 g, 3.766 mol, 5.0 eq.) And 450 mL of DMSO was degassed then placed under an atmosphere of argon. The mixture is then brought to 130 ° C then a solution of 1-iodoperfluorobutane (181.5 mL, 1.054 mol, 1.4 eq) was added dropwise over 30 minutes. The reaction mixture was stirred at 130 ° C for 5 h under argon. After returning to ambient temperature, 2 L of ethyl acetate and 1 L of water acetate are added. The mixture is then filtered through silica (Celite). The organic phase is washed with water (2 x 1 L), dried over sodium sulfate, filtered and then concentrated under reduced pressure to give ethyl 3- (perfluorobutane) crude benzoate (269.0 g, 730.6 mmol, 97%, light brown liquid).

1H RMN (CDCI3, 300 MHz) : δ (ppm) = 1.42 (t, 3J = 7.1 Hz, 3H), 4.44 (q, 3J = 7.1 Hz, 4H), 7.61 (t, 3J = 8.0 Hz, 1 H), 7.78 (d, 3J = 7.7 Hz, 1 H), 8.24-8.30 (m, 2H).

Second step

To a solution cooled with an ice bath 3- (perfluorobutane) benzoate (269.0 g, 730.6 mmol, 1 .0 eq.) And 500 mL of ethanol is added in small portions of sodium borohydride (82.9 g, 2.192 mol, 3.0 eq.). Temperature is monitored and should be less than 20 ° C. After the addition was complete, the reaction mixture was stirred at room temperature for 15 h. Once the stirring is ended, a saturated solution of NH 4 CI (2 L) is added to cool and then diluted with 2 L of ethyl acetate. The aqueous phase is extracted with ethyl acetate (1 x 1 L), then the organic phases are washed with i) saturated solution of NH 4 CI (1 x 1 L) and ii) with water (1 x 1 L). After drying over sodium sulfate and filtration, the organic phase is concentrated under reduced pressure to give (3-perfluorobutyl) phenylmethanol crude (228.9 g, 701.8 mmol, 96%, light brown liquid).

CLAIMS

1. hydrophobic organic liquid composition comprising at least a first organic compound of formula,

Wherein R ' "is selected from the following radicals:

- -C m H 2m + i with m≤ 20 of préférence≤ 15 wherein m is an integer,

- -C m H 2m -i with m≤ 20, wherein m is a non-zero integer,

- -C m H n F p Cl q Br s with m≤ 10, wherein n, p, q, s are integers which at least p, q or s is not zero,

- Ryle of formula b:

wherein at least any one of R A , R B , R C . R D and R E , equal or different, is a halogen atom or an electron-withdrawing group, in particular a halogenated group, the following group:

- F. CI. Br,

- C m F 2m + i with m≤ 4, wherein m is a non-zero integer,

- CF 2 CF 2 CpH 2 p + i with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- CH 2 C p F 2 p + i with p ≤ 4, where p is an integer,

- OCH 2 the CF 3 ,

- C(=0)CF3,

- C m H n F p Cl q Br s with m≤ 4, wherein n, p, q, s are integers which at least p, q or s is not zero,

- C (= 0) OC m H 2m + i m <4, where m is an integer, and

- C (= 0) C m H 2m + i m <4, where m is an integer,

or the radicals R A , R B . R C , R D and R E remaining (s) are chosen, which are identical or different, from the following non-electron-withdrawing radicals:

- H,

- CH The 3 ,

- CH 2 CH 2 CpF2p + i with p ≤ 4, where p is an integer,

- C m H 2m -i with m≤ 10, wherein m is a nonzero integer, and

- C m H 2m + i with m≤ 10, wherein m is a non-zero integer,

where one of R A to R E can be one of these two radicals C m H 2m -i

of Calix [4] East and thinner.

2. The composition of claim 1, wherein the radical R " 'is the nC 7 H 15 , nC 9 H 19 ,

3. The composition according to claim 1 or 2, wherein the plasticizer is selected from the group consisting of polar organic aromatic compounds.

4. A method of treating water comprising extracting at least two ionic species, said ionic species comprising an anionic species and a cationic species and being present in water to be treated, said method comprising the steps of:

a) mixing in a first reactor at a first temperature between a liquid hydrophobic organic phase and the water to be treated, said water to be treated being in the liquid state, for the subsequent obtaining of a liquid treated water and a hydrophobic liquid organic phase containing said ionic species,

said hydrophobic phase comprising:

at least a first organic compound solvating anions, protic and hydrophobic whose pKa in water at 25 ° C is at least 9, preferably 10.5 and is preferably below the pKa of water at 25 ° C , or at least less than 15 at 25 ° C and,

at least one second organic compound extractant cations and hydrophobic having a complexing constant of said cationic species whose value Log K, in methanol at 25 ° C, is greater than 2 and less than 11, preferably greater than 3 and less to 9;

b) separating on the one hand, of said treated liquid water and the other of said liquid organic phase containing said ionic species,

c) mixing, at a second temperature, in the liquid phase in a second reactor of said liquid organic phase charged ionic species and regeneration of liquid water, for the subsequent obtaining of a regenerated liquid organic phase and water liquid regeneration charged ionic species, the difference between said first and second temperatures ranging from 30 ° C to 150 ° C.

5. A method according to claim 4, characterized in that the method does not include a step wherein the pH of liquid water regeneration is significantly changed.

6. The method of claim 4 or 5, characterized in that said method comprises the subsequent steps of:

d) separating said regenerated liquid organic phase and liquid water containing said ionic species,

e) placing in indirect thermal contact with said liquid organic phase charged ionic species and said regenerated liquid organic phase.

7. A method according to any one of claims 4, 5 and 6, characterized in that the method comprises a regeneration of the water heating step carried out before step c).

8. The method of any one of claims 4 to 7, characterized in that the anionic species is chloride or sulfate.

9. Device for extraction of at least two ionic species, said ionic species comprising at least one anionic species and a cationic species present in the water to be treated comprising:

- a first reactor comprising a hydrophobic liquid organic phase as described in claim 1;

- a second reactor also comprising a hydrophobic liquid organic phase as described in claim 1;

- connections means for transferring said organic phase from the first reactor to the second reactor; and

- heating means of said liquid organic phase after leaving said first reactor.

10. N- [3,5-bis (trifluoromethyl) phenyl] octanamide.

11. N- [3,5-bis (trifluoromethyl) phenyl] decanamide.

12. N- [3,5-bis (trifluoromethyl) phenyl] dodecanamide.

13. N- [3,5-bis (trifluoromethyl) phenyl] tétradécanamide.

14. Use of a compound of formula B:

wherein at least any one of R A , RB, RC, RD and R E , equal or different, is a halogen atom or an electron-withdrawing group, in particular a halogenated group, the following group:

- F, Cl, Br,

C m F 2m + i m <4, where m is a non-zero integer,

CF 2 CF 2 CpH 2 p + i with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + i with p ≤ 4, where p is an integer,

CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

- OCH 2 the CF 3 ,

- C(=0)CF3,

- C m H n F p Cl q Br s m <4, where n, p, q, s are integers which at least p, q or s is not zero,

- C (= 0) OC m H 2m + 1 with m <4, where m is an integer, and

- C (= 0) C m H 2m + 1 with m <4, where m is an integer,

or the radicals R A , R B> R C , R D and R E remaining (s) are chosen, which are identical or different, from the following non-electron-withdrawing radicals:

- H,

- CH The 3 ,

CH 2 CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

C m H 2m- i m <10, where m is a nonzero integer, and

- C m H 2m + 1 with m <10, where m is a non-zero integer; where one of the radicals

R A -R E can be one of these two latter radicals C m H 2m-1 and C m H 2m + 1;

and wherein X is selected from the following radicals:

- OH,

- NH-R ',

OH

Y

C— '

or R 'and R ", identical or different, are chosen from the following radicals:

- H,

- C n H 2n -i n <4, where n is a nonzero integer,

- C n H 2n + i with n <4, where n is a nonzero integer,

- CH 2 CH 2 C p F 2p + i with p ≤ 4, where p is an integer,

- CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer

- CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where p is an integer,

- C m F 2m + 1 with m≤ 4, wherein m is a non-zero integer,

- C m H n F p Cl q Br s with m≤ 4, wherein n, p, q, s are integers which at least p, q or s is not zero,

- and an aryl radical of the formula b:

wherein R A , RB > RC, RD and R E , equal or different, are as previously defined in formula B;

and wherein R ' "is selected from the following radicals:

- C m H 2m + 1 with m≤ 20, wherein m is an integer,

- C m H 2m- i with m≤ 20, wherein m is a non-zero integer,

- C m H n F p Cl q Br s with m≤ 10, wherein n, p, q, s are integers which at least p, q or s is not zero,

- CH 2 CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

- CH 2 C p F 2p + 1 with p ≤ 4, where p is an integer,

- CF 2 C p H 2p + 1 with p ≤ 4, where m is an integer,

- CF 2 CF 2 C p H 2p + 1 with p ≤ 4, where m is an integer,

- C m F 2m + 1 with m≤ 4, wherein m is a non-zero integer,

- and an aryl radical of the formula b:

(b)

wherein R A , RB > RC, RD and R E , equal or different, are as previously defined for formula B.

15. Use according to claim 14, characterized in that in formula B, X is: