Method of obtaining organic salts, which contain anions of bis(perfluoroalkyl)phosphinate

FIELD: chemistry.

SUBSTANCE: claimed invention relates to method of obtaining organic salts, which contain anions of bis(perfluoroalkyl)phosphinate and can be applied in organic synthesis. Difference of claimed method lies in the fact that it includes carrying out reaction of tris(perfluoroalkyl)phosphinoxide with alcohol and organic base, stronger than alcohol.

EFFECT: elaboration of new method of obtaining organic salts with properties of ionic liquids.

11 cl, 14 ex

The presented invention relates to a method of preparation of organic salts containing the anion of bis(perfluoroalkyl)phosphinate, and salts obtained by this method and their use as ionic liquids.

Quaternary ammonium and postname salt is typically obtained by alkylation of amines or phosphines. For this purpose use a variety of alkylating agents, such as, for example, alkylhalides, alkyl sulphates, alkylacrylate, inter alia. This method can also be used for the synthesis of salts containing heterocyclic cations. The disadvantage of this method is the high cost alkylating agent, the toxicity of these alkylating agents (dimethylsulfate, for example, is highly toxic). In addition, with this method are salts that contain only some of the anions. In order to obtain salts containing other anions, it is necessary to conduct additional step of ion exchange, using the reaction of the salt with the acid of Bronsted or salt of the metal. This makes the synthesis of organic salts containing some anions, very expensive.

In recent years there has been increased interest in organic salts, which have a very low melting temperature. These compounds, due to their low melting temperature, more and more are used as ionic liquids, proof of which it may serve as some reviews published in recent years (.Wasserscheid, W.Keim, "lonische Flüssigkeiten - neue Lösungen für die Übergangsmetallkatalyse" [Ionic liquids - new solutions for catalysis by transition metals], Angew. Chem. 112 (2000) pp.3926-3945; R.Sheldon, "Catalytic reactions in ionic liquids" [Catalytic reactions in ionic liquids], Chem. Commun. 2001, pp.2399-2407; M.J.Earle, .R.Sheldon, "Ionic liquids. Green solvent for the future" [Ionic liquids. "Green" solvent of the future]. Pure Appl. Chem. 72, No.7 (1999), pp.1391-1398; .Welton, "Room temperature ionic liquids of alkylimidazolium cations and fluoroanions" [Ionic liquid at room temperature on the basis of the cations alkylimidazole and fluoride anions], J. of Fluorine Chem. 105 (2000) pp.221-227). The term ionic liquid is used to denote a compound that is liquid at room temperature or at relatively low temperatures. In addition, it includes organic cations, such as, for example, of tetraalkylammonium cations, tetraalkylammonium, N-alkylpyridine, 1,3-dialkylimidazolium and trialkylamine, and usually inorganic anions, such as, for example, BF₄^-, F₆^-, SbF₆^-, NO₃^-, CF₃SO₃^-, (CF₃SO₂)₂N^-, rSO₃^-, CF₃CO₂^-CH₃CO₂^-, Al₂Cl₇^-.

Properties of ionic liquids, such as, for example, melting point, thermal and electrochemicalmachining and viscosity, strongly depends on the nature of the anion and cation. The polarity and hydrophilicity or lipophilicity can be adjusted by selecting suitable pair of cation/anion. Each new anion and each new cation open new possibilities for adjusting the properties of ionic liquids.

From the point of view of practical applications of ionic liquids economic efficiency, i.e. cost, is crucial. And considering this factor, that is, due to their very high costs of production, known ionic liquids are currently not comparable with normal organic solvents. So it is very important to develop new methods for obtaining ionic liquids with low cost of production.

The recently proposed method of obtaining bis(perfluoroalkyl)phosphinic acid (DE 10216997). Neutralization of these acids with organic bases such as tetrabutylammonium hydroxide, leads to the formation of the corresponding salts. In addition, bis(perfluoroalkyl)phosphinic acid can be used for the conversion of organic chlorides in organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate emitting Hcl. However, the synthesis of the corresponding chlorides (or bromides) by alkylation described above or also first need to use expensive GI is rockside of alkylamine or alkylphosphine.

Reaction of Tris(heptafluoropropyl)phosphine oxide with methanol, which leads to the formation of simple dimethyl ether and bis(heptafluoropropyl)phosphinic acid known from the prior art (N.V.Pavlenko, et al., J Gen. Chem. USSR (Engl. Transl.), 59, No.3 (1989) pp.474-476). The formation of this product was explained through the formation of an intermediate complex product dimethyl ether bis(heptafluoropropyl)phosphinic acid, which is then alkiliruet source material with methanol, leading to the formation of simple dimethyl ether.

The aim of the presented invention is to provide an industrial and economical method of producing salts, which contain the anion of bis(perfluoroalkyl)phosphinate, and which does not have the disadvantages of the prior art. In particular, the objective of the presented invention is the provision of a method which has a good output and is simpler and less expensive in comparison with the known prior art methods.

This objective is achieved in accordance with the invention with the help characterize its independent claim and the dependent claims.

The invention is characterized by the fact that Tris(perfluoroalkyl)phosphine oxide forms the corresponding salt, which contains the anion of bis(perfluoroalkyl)FOSFA the Nata with good outputs due to a simple reaction with alcohol and an organic base, which is a stronger base than alcohol.

The anion of bis(perfluoroalkyl)phosphinate can be represented by the formula [(R^F)₂P(O)O]^-where R^Fin each case, independently of one another, represents performanceline group, as described below.

Tris(perfluoroalkyl)phosphine oxide can be described using the formula [(R^F)₃P=O, where R^Fin each case, independently of one another, represents performanceline group, as described below.

The presence of a stronger base than alcohol suppresses the undesirable formation of simple dialkylamide ether, to form the corresponding organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate.

Monohydroperoxide, which are formed as by-product in the method according to the invention are also valuable substances. They can be selected and used for different purposes, such as, for example, as described in DE 10216995.

In the method in accordance with the invention, the virtual is not formed extraneous substances which will collapse. In addition, due to the used materials and one-step reaction method in accordance with the invention can be implemented with little cost.

The method in accordance with the invention is mainly to provide Ecevit obtaining compounds, which contain the anion of bis(perfluoroalkyl)phosphinate, only in one stage. In addition, all necessary raw materials for newly cationic alkyl groups are not expensive alkylating agents, and cheap alcohol.

Thus, the method in accordance with the invention for the preparation of organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate includes, at least, the reaction of Tris(perfluoroalkyl)phosphine oxide with an alcohol and an organic base, which is a stronger base than alcohol.

In a preferred variant of the method in accordance with the invention used organic base is a compound of General formula (1)

or the General formula (2)

in which X represents

,,or,

Y represents-O-, -S-, -Se-, -C(=O)-, -C(=S) -, or-C(=Se)-,

R represents-H for Y≠O and where, in the case of formula (2), all R cannot simultaneously be H,

unbranched or branched alkyl having 1 to 20 C atoms,

unbranched or branched alkenyl having 2-20 C atoms and one or more double bonds,

unbranched or branched quinil, have s 2-20 C atoms and one or more triple relations, or

saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, in particular phenyl, which may be substituted by alkyl groups having 1-6 C atoms,

where the substituents R, in each case, are the same or different,

where the substituents R can be related to each other, forming a pair with a simple or double bond,

where one or more, but not all, of the substituents R may be partially or fully substituted by Halogens, in particular-F and/or-CL, or partially by CN or-NO₂,

and where one or two non-adjacent carbon atoms of the substituent R may be replaced by atoms and/or groups of atoms, which is selected from the group of-O-, -C(O)-,

-C(O)O-, -C(O)NH-, -C(O)NR'-, -S-, -S(O)-, -S(O)NH-, -S(O)NR'-, -S(O)O-, -S(O)₂-, -S(O)₂O-, -S(O)₂NH-, -S(O)₂NR'-, -N=, -N=N-, -NH-, -NR'-, -PH-, -PR'-, -P(O)R'-, -P(O)R'-O-,

-O-P(O)R'-O - I-PR'₂=N-, where R' represents a non-, partially or perfluorinated C₁-C₆-alkyl, C₃-C₇-cycloalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted heterocycle.

Thus, in addition to hydrogen, suitable substituents R of the organic bases used in accordance with the invention are C₁-C₂₀-in particular With₁-C₁₂-kalkiliya groups, and saturated or unsaturated, i.e. also aromatic, With₃-C₇-the CEC is alkylene group, which may be substituted

C₁-C₆-alkyl groups, in particular phenyl. However, in the case of the founding of the formula (2), all R cannot be hydrogens, that is, the ground cannot be H₂O, H₂S or H₂Se.

Alkyl group which has 1-12 C atoms means, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2 - or 3-methylbutyl, 1,1-, 1,2 - or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl. Alkyl groups can also be partially or fully substituted by Halogens, in particular-F and/or CL. Fluorinated alkyl groups are deformity, trifluoromethyl, pentafluoroethyl, pentafluoropropyl, heptafluoropropyl, heptafluorobutyl or nonattorney. The term performanceline group means that all the atoms N-alkyl group substituted by atoms F.

Unbranched or branched alkenyl, which has from 2 to 20 C atoms, which may contain a number of double bonds is, for example, allyl, 2 - or 3-butenyl, Isobutanol, second-butenyl, in addition, 4-pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, -C₉H₁₇, -C₁₀H₁₉up With₂₀H₃₉preferably allyl, 2 - or 3-butenyl, Isobutanol, second-butenyl, in addition, preference is given to 4-pentenyl from pentenyl or hexenyl.

Unbranched or branched quinil, which has from 2 to 20 C atoms, which can also present a number of ternary relations is, for example, ethinyl, 1 - or 2-PROPYNYL, 2 - or 3-butynyl, in addition, 4-pentenyl, 3-pentenyl, hexenyl, heptenyl, octenyl, -C₉H₁₅-, -C₁₀H₁₇up With₂₀H₃₇preferably ethinyl, 1 - or 2-PROPYNYL, 2 - or 3-butenyl, 4-pentenyl, 3-pentenyl or hexenyl.

Unsubstituted saturated or partially or fully unsaturated cycloalkyl groups having 3-7 C atoms, are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclopent-1,3-dienyl, cyclohexenyl, cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, phenyl, cycloheptenyl, cyclohepta-1,3-dienyl, cyclohepta-1,4-dienyl or cyclohepta-1,5-dienyl, which may be substituted C₁-C₆-alkyl groups, where cycloalkyl group or cycloalkenyl group, substituted C₁-C₆-alkyl groups may in turn also be substituted by halogen atoms such as F, Cl, Br or I, in particular F or Cl, CN or NO₂.

Three or two substituent R of the organic base may be the same or different. The substituents R may also be linked in this way that the formed mono-, bi - or polycyclic bases, for example, preferably hetero is ilycheskie connection pyridine, the imidazole, pyrazole, triazole, pyridazine, pyrimidine, pyrazin, thiazole, oxazole, benzoxazole, benzothiazole, pyrrolidine, piperidine, piperazine, morpholine, indole, indoline, quinoline, isoquinoline or aniline, each of which may optionally be substituted

unbranched or branched alkyl that has 1 to 20 C atoms,

unbranched or branched alkenyl, which has 2-20 C atoms and one or more double bonds,

unbranched or branched quinil, which has 2-20 C atoms and one or more triple bonds or

saturated, partially or fully unsaturated cycloalkyl, which has 3 to 7 C atoms, in particular phenyl,

which may be substituted by alkyl groups having 1-6 atoms C.

These heterocycles are preferably unsubstituted or substituted unbranched or branched alkyl groups with 1-20 C atoms, in particular 1 to 12 atoms C.

The substituents R may be partially or completely replaced by halogen atoms, in particular-F and/or Cl, or partially by CN or NO₂but where all substituents R should not be in the fully halogenated form. In addition, the substituents R may contain one or two non-adjacent heteroatoms or groups of atoms, which is selected from the group O, S(O), C(O)O, C(O)NH, C(O)NR', S, S(O), S(O)NH, S(O)NR', (O)O, SO₂, SO₂O, SO₂NH, SO₂NR', N, N=N, NH, NR', PH, PR', P(O)R', P(O)R O, OP(O)R O PR'₂=N, where R' can be non-, partially or perfluorinated C₁-C₆-alkyl, C₃-C₇-cycloalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted heterocycle.

In R'₃-C₇-cycloalkyl represents, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.

In R' substituted phenyl is a phenyl, which is substituted C₁-C₆-alkyl, C₁-C₆-alkenyl, NO₂, F, Cl, Br, I, HE, C₁-C₆-alkoxy, CN, SCN, SCF₃, SO₂CF₃With(O)O-C₁-C₆-alkyl, NH₂C₁-C₆-alkylamino or C₁-C₆-dialkylamino, C(O)NR₂, SO₂OR", SO₂X', SO₂NR₂or NHC(O)R", where X' represents F, Cl or Br and R" represents a non-, partially or perfluorinated C₁-C₆-alkyl or C₃-C₇-cycloalkyl as defined for R', for example o-, m - or p-were, o-, m - or p-ethylphenyl, o-, m - or p-propylphenyl, o-, m - or p-isopropylphenyl, o-, m - or p-tert-butylphenyl, o-, m - or p-AMINOPHENYL, o-, m - or p-(N,N-dimethylamino)phenyl, o-, m - or p-nitrophenyl, o-, m - or p-hydroxyphenyl, o-, m - or p-methoxyphenyl, o-, m - or p-ethoxyphenyl, o-, m - or p-(trifluoromethyl)phenyl, o-, m - or p-(triptime the si)phenyl, o-, m - or p-(trifloromethyl)phenyl, o-, m - or p-forfinal, o-, m - or p-chlorophenyl, o-, m - or p-bromophenyl, o-, m - or p-iopener, in addition, preferably 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3, 5dimethylphenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dihydroxyphenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-differenl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dichlorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dibromophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-acid, 5-fluoro-2-were, 3,4,5-trimethoxyphenyl or 2,4,5-trimetilfenil.

In R' a heterocycle means a saturated or unsaturated mono - or bicyclic heterocyclic radical that has from 5 to 13 ring members, where you can attend 1, 2 or 3 atom N and/or 1 or 2 S atom or heterocyclic radical may be mono - or polyamidine C₁-C₆-alkyl, C₁-C₆-alkenyl, NO₂, F, Cl, Br, I, HE, C₁-C₆-alkoxy, CN, SCN, SCF₃, SO₂CF₃With(O)O-C₁-C₆-alkyl, NH₂C₁-C₆-alkylamino or C₁-C₆-dialkylamino, C(O)NR₂, SO₂OR", SO₂X', SO₂NR₂or NHC(O)R", where X' and R" have the meanings specified above.

The heterocyclic radical is preferably substituted or unsubstituted 2 - or 3-furyl, 2 - or 3-thienyl, 1-, 2 - or 3-pyrrolyl, 1-, 2-, 4 - or 5-imidazolyl, 3-, 4 - or 5-pyrazolyl, 2-, 4 - or 5-oxazolyl, 3-, 4 - or 5-isoxazolyl, 2-, 4 - or 5-thiazolyl, 3-, 4 - or 5-isati who was Salil, 2-, 3 - or 4-pyridyl, 2-, 4-, 5 - or 6-pyrimidinyl, in addition, preferably 1,2,3-triazole-1-, -4 - or-5-yl, 1,2,4-triazole-1-, -4 - or-5-yl, 1 - or 5-tetrazole, 1,2,3-oxadiazol-4 - or-5-yl, 1,2,4-oxadiazol-3 - or-5-yl, 1,3,4-thiadiazole-2 - or-5-yl, 1,2,4-thiadiazole-3 - or-5-yl, 1,2,3-thiadiazole-4 - or-5-yl, 2-, 3-, 4-, 5 - or 6-2H-dipiradol, 2-, 3 - or 4-4H-dipiradol, 3 - or 4-pyridazinyl, pyrazinyl, 2-, 3-, 4-, 5-, 6 - or 7-benzofuran,

2-, 3-, 4-, 5-, 6 - or 7-benzothiazyl, 1-, 2-, 3-, 4-, 5-, 6 - or 7-1H-indolyl, 1-, 2-, 4 - or 5-benzimidazolyl, 1-, 3-, 4-, 5-, 6 - or 7-benzimidazolyl, 2-, 4-, 5-, 6 - or 7-benzoxazolyl, 3-, 4-, 5-, 6 - or 7-benzisoxazole, 2-, 4-, 5-, 6 - or 7-benzothiazolyl, 2-, 4-, 5-, 6 - or 7-benzothiazolyl, 4-, 5-, 6 - or 7-benzo-2,1,3-oxadiazole, 1-, 2-, 3-, 4-, 5-, 6-, 7 - or 8-chinoline, 1-, 3-, 4-, 5-, 6-, 7 - or 8-ethenolysis, 1-, 2-, 3-, 4 - or 9-carbazolyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8 - or 9-acridine, 3-, 4-, 5-, 6-, 7 - or 8-indolinyl, 2-, 4-, 5-, 6-, 7 - or 8-hintline or 1-, 2 - or 3-pyrrolidinyl.

Without limiting the generality, examples of the substituents R of the organic bases used in accordance with the invention, are

-CH₃- ₂H₅- ₃H₇, -CH(CH₃)₂- ₄H₉- (CH₃)₃- ₅H₁₁- ₆H₁₃, -C₇H₁₅- ₈H₁₇, -C₉H₁₉- ₁₀H₂₁- ₁₂H₂₅- ₂₀H₄₁, -Och₃, -Och(CH₃)₂, -CH₂Och₃- 2H₄Och(CH₃)₂, -S₃, -S(CH₃)₂, -C₂H₄SC₂H₅- ₂H₄S(CH₃)₂, -S(O)CH₃,

-CH₂SO₂CH₃, -OSO₂CH₃, -CH₂N(H)₂H₅- ₂H₄N(H)₂H₅, -CH₂N(CH₃)CH₃- ₂H₄N(CH₃)CH₃, -N(CH₃)₂, -N(CH₃)₃H₅, -N(CH₃)CF₃, -O-C₄H₈-O-C₄H₉, -S-C₂H₄-N(C₄H₉)₂, -CF₃, -C₂F₅- ₃F₇, -C₄F₉- (CF₃)₃, -CF₂SO₂CF₃, -C₂F₄N(C₂F₅)C₂F₅, -CFH₂, -CHF₂, -CH₂CF₃, -C₂F₂H₃,

-C₃FN₆, -CH₂With₃F₇- (F₂)₃, -Cho, -CH₂C(O)CH₃, -CH₂With(O)₂H₅, -CH₂C(O)och₃CH₂S(O)OS₂H₅-C(O)CH₃-C(O)och₃, -CH=CH₂, -CH₂CH=CH₂- (CH₃)=CH₂, -CH=SNSN₃, -CH₂SN=SNSN₃, -O-CH=CH₂, -O-CH₂CH=CH₂, -C≡CH, -CH₂With≡CH, -C≡CLO₃, -CH₂C≡CLO₃,

The choice of a suitable basis for the method in accordance with the invention is absolutely simple for the average person skilled in the art. With particular preference in accordance with the invention is given to the grounds, which are selected from the group comprising (C₂H₅)₃N, (C₂H₅)₂NH, (C₂H₅)₃R, (C₂H₅O)₃R, (C₄H₉)₃P,

CH₃-S-CH₃, (CH₃)₂N-C(O)-N(CH₃)₂With₆H₅-Se-C₆H₅, guanidine, pyridine, imidazole, N-Mei, benzoxazole, benzothiazole, pyrrolidine, piperidine, piperazine, aniline, N,N-dimethylaniline, benzylamine, N-ethylbenzylamine or diphenylsulfide.

Suitable alcohol is chosen so as to form the desired cation after alkylation using Foundation. The appropriate choice is absolutely not difficult for renego specialist in this field. Without it limits the generalization of alcohol is described by the formula, R^OHIs HE using the method in accordance with the invention, preferably an aliphatic alcohol, that is, R^OHin this case, represents an aliphatic group. Particular preference is given to variants of the method, in which the alcohol is chosen from the group comprising methanol, ethanol, isopropanol, n-propanol, allyl alcohol, butanol, hexanol or benzyl alcohol, but also use fluorinated aliphatic alcohols, such as 4,5,5-triterpen-4-EN-1-ol or 3,3,4,4,5,5,5-heptadecene-1-ol.

Tris(perfluoroalkyl)phosphine oxides used in accordance with the invention, can be obtained using conventional techniques well known to the average person skilled in the art. These compounds are preferably obtained by reaction with hexamethyldisiloxane (V.Ya.Sememii et al., J. Gen. Chem. USSR (Engl. Trans.) 55, No.12 (1985), 2415-2417). Corresponding descriptions are included here as reference and considered part of the description.

Also in accordance with the invention, it is possible to use a mixture of two or more of Tris(perfluoroalkyl)phosphine oxides. Preferably in each case in the method in accordance with the invention responds only one of Tris(perfluoroalkyl)phosphine oxide.

Tris(perfluoroalkyl)phosphine oxides used in accordance with the invention, or their respective produced in the water have three performanceline group, marked with the abbreviation R^Fabove, and which are the same or different. In each case, the preference is given to the use of Tris(perfluoroalkyl)phosphine oxides having the same performanceline group.

In the preferred embodiment of the method in accordance with the invention, the use of Tris(perfluoroalkyl)phosphine oxide, in which performanceline groups contain from 1 to 20 C atoms and are unbranched or branched. Particular preference is given to the source materials, which performanceline groups have from 1 to 12 atoms C.

Without limiting the generalization used Tris(perfluoroalkyl)phosphine oxide is a compound which is chosen from the group comprising (CF₃)₃P(O), (C₂F₅)₃R(O), (C₃F₇)₃P(O) and (C₄F₉)₃P(O).

Suitable reaction medium for the method in accordance with the invention is preferably a conventional polar or non-polar solvent known to a person skilled in the art. An alternative method in accordance with the invention can also be carried out without the presence of solvent. Without limiting the generalization of the used polar solvent is particularly preferably dichloromethane, 1,2-dimethoxyethane, benzene, or mixtures thereof.

The temperature at which carry out the reaction in the accordance with the invention, preferably is in the range of temperatures from -20 to 200°C. the Reaction is particularly preferably carried out at a temperature in the range from 0 to 100°C. the reaction Temperature is very particularly preferably room temperature.

In a preferred variant of the method in accordance with the invention is carried out without excess or up to five-fold excess of one of the reactants, based on the molar quantities. The reaction is particularly preferably carried out using approximately equimolar amounts of starting materials.

In addition, the invention relates to organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate obtained using the method in accordance with the invention.

The compounds obtained in the method in accordance with the invention, have colpotomy nature, relatively low melting temperature (usually below 100°C) and can be used as ionic liquids.

Salts obtained in the method in accordance with the invention, can be used as solvents for many synthetic or catalytic reactions, such as acylation or alkylation Friedel -, cycloaddition Diels-alder reaction, hydrogenation reactions, and oxidation, the Heck reaction, Suzuki condensation, hydroformylation.

You can also use the connection, the scientists using the method in accordance with the invention as non-aqueous electrolytes, not necessarily, in combination with other electrolytes known to the average person skilled in the art, or as a conductive salt in an electrochemical cell.

In addition, the salt obtained by the method in accordance with the invention, can be used as non-aqueous polar substances in a suitable reaction as the catalyst phase transfer, as a surfactant (surface active agent), as a plasticizer or as a medium for heterogenization homogeneous catalysts.

The following General scheme discloses a method in accordance with invention

where R^F, R, X, Y, and R^OHhave the values listed in the description. See arrow in case monohydroperoxide R^FH means that the compound is volatile.

A full description of the content of all applications, patents and publications mentioned above and below, is included in this application with references.

Even without additional comments it is clear that the person skilled in the art can use the above description in a broad framework. Therefore, the preferred embodiments and examples should be considered only as illustrative description, which is not limited in any way.

NMR spectra were removed from the solutions in deuterated solvents is ri 20°C on a spectrometer Bruker Avance 300 with 5 mm ¹N/a BB broadband head with deuterium gate. The frequency of measurement of different nuclei is

¹H: 300,13 MHz,¹¹B: 96,92 MHz,¹⁹F: 282,41 MHz and³¹R: 121,49 MHz. The counting direction is specified separately for each spectrum or each set of data.

Examples

Example 1. N-Ethylpyridine bis(pentafluoroethyl)phosphinate

15,69 g (38,8 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dichloromethane and to 3.09 g (39,1 mmol) of pyridine in 50 ml flask, equipped with reflux condenser, cooled to -65 - -70°C. was Added 1.85 g (40,2 mmol) of ethanol for 15 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 14,56 g dark red very viscous material. Output N-ethylpyridine bis(pentafluoroethyl)phosphinate 91.7%.

¹⁹F NMR (relatively CCl₃F - internal standard; the solvent CD₃CN): -80,13 m (2F₃); -124,81 dm (2CF₂);²J_P,F=67 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 1,59 t (CH₃); 4,59 q (CH₂); 8,03 m (2CH); 8,50 tt (CH); 8,78 m (2CH);³J_H,H=7,3 Hz;³J_H,H=7,8 Hz;⁴J_H,H=1.2 Hz.

^{31 P NMR (relative to 85% H₃RHO₄; solvent CD₃SP): -2,19 quin.;3J_P,F=67 Hz.}

Example 2. Ethyldimethylamine bis(pentafluoroethyl)phosphinate

to 4.92 g (12.2 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³1,2-dimethoxyethane and 0,775 g (12.5 mmol) of dimethyl sulfide in 50 ml flask, equipped with reflux condenser. Added over 1 minute while stirring the reaction mixture with a magnetic stirrer at room temperature 0,560 g (12.2 mmol) of ethanol. The reaction mixture is refluxed for 5 hours and 1,2-dimethoxyethan distilled off. The residue is dried at 40°C in a vacuum of 1.4 PA, receiving 4,18 g of solid material. Output ethyldimethylamine bis(pentafluoroethyl)phosphinate is 87,4%.

¹⁹F NMR (relatively CCL₃F - internal standard; the solvent CD₃CN): -80,19 m (2F₃); -124,96 dm (2CF₂);²J_P,F=69 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 1,37 t (CH₃); 2,81 s (2CH₃); 3,28 q (CH₂);³J_H,H=7,4 Hz.

³¹P NMR (relative to 85% H₃RHO₄; solvent CD₃SP): -1,86 quin.;²J_P,F=69 Hz.

Example 3. N-Methylbenzimidazole bis(pentafluoroethyl)phosphinate

9,40 g (23,3 mmol) of Tris(pentaho is ethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dry 1,2-dimethoxyethane and 2.77 g (23,3 mmol) benzoxazole 50 ml flask, equipped with reflux condenser. Added during 5 minutes while stirring the reaction mixture with a magnetic stirrer at room temperature 0,745 g (23,3 mmol) of methanol. The reaction mixture is stirred for 1 hour and 1,2-dimethoxyethan distilled off. The residue is dried at 40°C in a vacuum of 1.4 PA, receiving 9,44 g of solid material (melting point of 78-79°C). Output N-methylbenzimidazole bis(pentafluoroethyl)phosphinate is 93.1%of.

¹⁹F NMR (relatively CCl₃F - internal standard; the solvent CD₃SP): -80,16 m (2F₃); -124,93 dm (2CF₂);²J_P,F=71 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 4,20 d (CH₃); a 7.85 m (2CH); 8,01 m (2CH); of 10.05 br. s (CH);⁴J_H,H=1.0 Hz.

³¹P NMR (relative to 85% H₃RHO₄; solvent CD₃SP): -1,77 quin.;²J_P,F=71 Hz.

Example 4. Triethyl-out-of Propylamine bis(pentafluoroethyl)phosphinate

of 9.30 g (23,0 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with a 8.34 g (82,4 mmol) of triethylamine and 50 ml flask, equipped with reflux condenser and magnetic stirrer. To this reaction mixture at 0°C. cooling bath of ice) when paramasivan the gain of 1.41 g (23.5 mmol) of ISO-propanol. The reaction mixture was stirred at 0°C for 5 hours and at room temperature for 36 hours. All volatile products are removed at 50°C in high vacuum at 1.4 PA, getting a 9.25 g of solid material, which contains 37% of triethylamine bis(pentafluoroethyl)phosphinate and 63% triethyl-out-of Propylamine bis(pentafluoroethyl)phosphinate.

To highlight triethyl-out-of Propylamine bis(pentafluoroethyl)phosphinate, this mixture is dissolved in 15 cm³water and treated at room temperature aqueous KOH (0,477 g of KOH in 5 cm³of water). Water is removed on a rotary evaporator and the residue is dried for three hours at 50°C in high vacuum (1,4 PA), getting to 8.70 g of solid material suspended in 15 cm³dichloromethane, the precipitate is filtered off and washed twice on the filter with 5 cm³dichloromethane. After removal of dichloromethane obtain 5.9 g of the solid salt. Output triethyl-out-of Propylamine bis(pentafluoroethyl)phosphinate is 57,7%, based on the Tris(pentafluoroethyl)phosphine oxide.

¹⁹F NMR (relatively CCL₃F - internal standard; the solvent CD₃SP): -80,18 m (2F₃); -124,89 dm (2CF₂);²J_P,F=66 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 1,29 tm (SN₃); 1,38 dm (2CH₃); 3,31 q (3CH₂); 3,71 hep.(CH);³J_H,H=7,3 Hz;³J_H,H=6,7 Hz.

³ P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,32 quin. (1P);²J_P,F=66 Hz.

Example 5: Ethyltriphenylphosphonium bis(pentafluoroethyl)phosphinate

12.00 g (29.7 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dichloromethane and 6.00 g (29.7 mmol) of tributylphosphine 50 ml flask, equipped with reflux condenser, in which the temperature is between minus 65 to minus 70°C. For 3 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer was added to 1.37 g (29.7 mmol) of ethanol. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 15,60 g of solid material (the melting temperature of 42-43°C). Output ethyltriphenylphosphonium bis(pentafluoroethyl)phosphinate is 98,7%.

¹⁹F NMR (relatively CCL₃F - internal standard; the solvent CD₃CN): -80,21 m (2F₃); -124,89 dm (2CF₂);²J_P,F=65 Hz.

¹H NMR (relative to TMS; solvent CD₃CN): 0,94 t (SN₃); 1,17 dt (CH₃); 1,46 m (SN₂); 2,11 m (3CH₂); 2,15 dq (CH₂);³J_H,H=7,1 Hz;³J_H,H=7,6 Hz;³J_P,H=13,0 Hz;

⁴J_P,H=18.2 Hz.

³¹P NMR (relative to 85% H₃RHO₄; the solution is tel CD ₃SP): 34,73 br. s (1P); -2,39 quin. (1P);²J_P,F=65 Hz.

Example 6. Tetraethylammonium bis(pentafluoroethyl)phosphinate

br12.62 g (% 31.2 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dichloromethane and of 3.16 g (% 31.2 mmol) of triethylamine in 50 ml flask, equipped with reflux condenser, in which the temperature is between minus 65 to minus 70°C. For 3 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer was added 1.44 g (% 31.2 mmol) of ethanol. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 13,07 g of solid material (melting point 103-105°C). The output of tetraethylammonium bis(pentafluoroethyl)phosphinate is to 97.1%.

¹⁹F NMR (relatively CCL₃F - internal standard; the solvent CD₃SP): -80,23 m (2F₃); -124,94 dm (2CF₂);²J_P,F=65 Hz.

¹H NMR (relative to TMS; solvent CD₃CN): 1,20 tm (CH₃); 3,18 q (CH₂);

³J_H,H=7,3 Hz.

³¹P NMR (relative to 85% H₃RHO₄; solvent CD₃SP): -2,33 quin.;²J_P,F=65 Hz.

Example 7. N-Ethylbenzothiazoline bis(pentafluoroethyl)phosphinate

a 10.74 g (to 26.6 mmol) of Tris(pentaborate is)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dichloromethane and of 3.53 g (26,1 mmol) of benzothiazole in a 50 ml flask, equipped with reflux condenser, in which the temperature is between minus 65 to minus 70°C. For 5 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer was added 1.22 g (of 26.5 mmol) of ethanol. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 13,07 g of solid material (melting point 76-77°C). Output N-ethylbenzothiazoline bis(pentafluoroethyl)phosphinate is 82,0%, based on benzothiazole.

¹⁹F NMR (relatively CCL₃F - internal standard; the solvent CD₃SP): -80,08 m (2F₃); -124,81 dm (2CF₂);²J_P,F=67 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 1,66 t (CH₃); 4,81 q (CH₂); 7,88 m (2CH); 8,30 m (2CH); 10,34 s (CH);³J_H,H=7,3 Hz.

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,00 quin.;²J_P,F=67 Hz.

Example 8. N,N-Dimethylimidazolium bis(pentafluoroethyl)phosphinate

20,49 g (50,7 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, is mixed with 30 cm³dichloromethane and of 4.16 g (50,7 mmol) of N-methylimidazole in a 100 ml flask, equipped with check the fridge, in which the temperature is between minus 65 to minus 70°C. For 15 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer was added 1,623 g (50,7 mmol) of methanol. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 19,23 g of solid material. Exit N,N-dimethylimidazolium bis(pentafluoroethyl)phosphinate is 95.2 percent (the melting temperature of 35-37°C).

¹⁹F NMR (relatively CCl₃F - internal standard; the solvent CD₃SP): -80,18 m (2CF₃); -124,90 dm (2CF₂);²J_P,F=66 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 3,84 d (2CH₃); 7,37 d (2CH); 8,61 br. s (CH);⁴J_H,H=1,6 Hz;⁴J_H,H=0.6 Hz.

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,16 quin.;²J_P,F=66 Hz.

Example 9. N-Methyl-N-ethylimidazolium bis(pentafluoroethyl)phosphinate

23,22 g (57.5 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, is mixed with 30 cm³dichloromethane and 4,72 g (57.5 mmol) of N-methylimidazole in a 100 ml flask, equipped with reflux condenser, in which the temperature is between minus 65 to minus 70°C. For 15 minutes at room temperature with stirring the reaction with the art with a magnetic stirrer was added 2,643 g (57,4 mmol) of ethanol. The reflux condenser is heated to room temperature and dichloromethane is distilled off. The residue is dried at 60°C in vacuum of 1.4 PA, receiving 21,97 g of liquid material. The output of the N-methyl-N-ethylimidazolium bis(pentafluoroethyl)phosphinate is of 92.9%.

¹⁹F NMR (relatively CCl₃F - internal standard; the solvent CD₃SP): -80,17 m (2F₃); -124,90 dm (2CF₂);²J_P,F=66 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 1,47 t (CH₃); a 3.87 s (CH₃); 4,21 q (CH₂); of 7.48 dd (CH); 7,56 dd (CH); 9,01 br. s (CH);³J_H,H=7,3 Hz; J_H,H=1,8 Hz.

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,07 quin.;²J_P,F=67 Hz.

Example 10. 2-Methyl-1,1,3,3-tetramethylthiourea bis(pentafluoroethyl)phosphinate

6,72 g (of 16.6 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 15 cm³dimethoxyethane and of 1.93 g (of 16.6 mmol) tetramethylrhodamine a 25 ml flask, equipped with reflux condenser. To this mixture under stirring with a magnetic stirrer was added 0,532 g (of 16.6 mmol) of methanol. The reaction mixture is boiled for 5 hours and all volatile products are removed at 50°C in high vacuum (1,4 PA), receiving 6,59 g of a viscous fluid. The yield of 2-methyl-1,1,3,3-tetramethylthiourea bis(pentafluoroethyl)phosphinate is 91,9%.

¹⁹F YAM is (relatively CCl ₃F - internal standard; the solvent CD₃SP): -80,21 m (2F₃); -124,91 dm (2CF₂);²J_P,F=67 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 3,05 s (SN₃); 4,05 s (och₃).

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,12 quin.;²J_P,F=67 Hz.

Example 11. Methyldiphenylamine bis(pentafluoroethyl)phosphinate

between 6.08 g (15,05 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 15 cm³dimethoxyethane and 3.51 g (15,05 mmol) diphenylsilane a 25 ml flask, equipped with reflux condenser. To this mixture under stirring with a magnetic stirrer was added 0,482 g (15,05 mmol) of methanol. The reaction mixture is boiled for 8 hours and all volatile products are removed at 50°C in high vacuum (1,4 PA). The residue is washed with pentane (three times for 5 cm³) and dried for one hour at 50°C in a vacuum of 1.4 PA, receiving 4,06 g light green viscous liquid. The output methyldiphenylamine bis(pentafluoroethyl)phosphinate is 49.2%.

¹⁹F NMR (relatively CCl₃F - internal standard CD₃CN film): -80.16 m

(2F₃); -124,84 dm (2CF₂);²J_P,F=77 Hz.

¹H NMR (relative to TMS; solvent CD₃JV film): 3,39 s (CH₃); 7,60-7,80 m (2C₆H₅).

³¹P NMR (relative to 85% H ₃PO₄; solvent CD₃JV film): -1,15 quin.;²J_P,F=77 Hz.

Example 12. 1-(4,5,5-Cryptor-4-pentenyl)-3-methylimidazolium bis(pentafluoroethyl)phosphinate

8,61 g (of 21.3 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dry benzene and 1.75 g (of 21.3 mmol) of N-methylimidazole in a flask equipped with reflux condenser, in which the temperature of minus 25°C. To this mixture at room temperature under stirring with a magnetic stirrer was added 2,98 g (21,3 mmol) 4,5,5-triterpen-4-EN-1-ol. The reaction mixture is heated on an oil bath with a temperature of 100°C for 20 minutes. After cooling to room temperature phosphinate separated from the benzene phase and washed twice with 10 cm³of benzene. Dried at 60°C (2 hours) in a vacuum of 13.3 PA, receiving 10,53 g of 1-(4,5,5-Cryptor-4-pentenyl)-3-methylimidazolium bis(pentafluoroethyl)phosphinate as a liquid. The output is of 97.6%.

¹⁹F NMR (relatively CCl₃F - internal standard; CD₃JV film): -80.22 m

(2F₃); -124,90 dm (2CF₂);²J_P,F=66 Hz; -105,27 dd (CF);²J_F,F=89 Hz;³J_F,F=33 Hz; -123,72 dd (CF);²J_F,F=89 Hz;³J_F,F=113 Hz; -174,2 ddt (CF);²J_F,F=89 Hz;³J_F,F=113 Hz;³J_F,H=21 Hz.

¹H NMR (relative to TMS solvent CD ₃JV film): 2,08 quin (CH₂);³J_H,H=7,4 Hz; 2,36 dddt (CH₂);³J_H,H=7,4 Hz;³J_F,H=21 Hz;⁴J_H,F=4 Hz;⁴J_H,F=3 Hz; 3,82 s

(CH₃); 4,19 t (CH₂);³J_H,H=7 Hz; 7,37 dd (CH);³J_H,H=7,3 Hz; J_H,H=1.5 Hz; 7,42 dd (CH);³J_H,H=7,3 Hz; J_H,H=1.5 Hz; 8,66 br. s (CH).

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃JV film): -1,61 quinsep;²J_P,F=66 Hz;³J_P,F=1 Hz.

Example 13. 1-(3,3,4,4,5,5,5-Heptafluorobutyl)-3-methylimidazolium bis(pentafluoroethyl)phosphinate

of 8.27 g of 20.5 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dry benzene and 1.67 g (20.3 mmol) of N-methylimidazole in a flask equipped with reflux condenser, in which the temperature of minus 25°C. To this mixture at room temperature under stirring with a magnetic stirrer was added 4,37 g (to 20.4 mmol) of 3,3,4,4,5,5,5-heptadecene-1-ol. The reaction mixture is heated on an oil bath with a temperature of 100°C for 20 minutes. After cooling to room temperature phosphinate separated from the benzene phase and washed twice with 10 cm³of benzene. Dried at 60°C (2 hours) in a vacuum of 13.3 PA, receiving for 11.55 g of 1-(3,3,4,4,5,5,5-heptafluorobutyl)-3-methylimidazolium bis(pentafluoroethyl)phosphinate as liquids the ü. The output is 97.5%.

¹⁹F NMR (relatively CCl₃F - internal standard; CD₃JV film): -80,26 m

(2F₃); -80,16 t (CF₃),⁴J_F,F=9 Hz; -124,92 dm (2CF₂);²J_P,F=66 Hz; -114,23 qt (CF₂);³J_F,H=18.5 Hz;⁴J_F,F=9 Hz; -127,33 s (CF₂).

¹H NMR (relative to TMS; solvent CD₃CN film): 2,82 ttt (CH₂);³J_H,F=18.5 Hz;³J_H,H=7,1 Hz;⁴J_H,F=1.3 Hz; 3,83 s (CH₃); 4,51 t (CH₂);³J_H,H=7,1 Hz; 7,38 dd (SN);³J_H,H=7,1 Hz;³J_H,H=1.5 Hz; 7,51 dd (CH);³J_H,H=7,1 Hz;³J_H,H=1.5 Hz; 8,79 br. s (CH).

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃CN film): -1,59 quinsep;

²J_P,F=66 Hz;³J_P,F=1 Hz.

Example 14. 1-Allyl-3-methylimidazolium bis(pentafluoroethyl)phosphinate

17,81 g (to 44.1 mmol) of Tris(pentafluoroethyl)phosphine oxide, (C₂F₅)₃P=O, mixed with 20 cm³dry benzene and 3,62 g (to 44.1 mmol) of N-methylimidazole in a flask equipped with reflux condenser, in which the temperature of minus 65 to 70°C. For 15 minutes at room temperature with stirring of the reaction mixture with a magnetic stirrer was added 2,56 g (to 44.1 mmol) of allyl alcohol. The reflux condenser is heated to room temperature benzol distilled off. The residue is dried at 80°C in vacuum 13 PA, receiving 16,97 g of viscous liquid material. Output 1-allyl-3-methylimidazolium bis(pentafluoroethyl)phosphinate is 90.7 percent.

¹⁹F NMR (relatively CCl₃F - internal standard; CD₃SP): -80,14 m (2F₃); -124,90 dm (2CF₂);²J_P,F=66 Hz.

¹H NMR (relative to TMS; solvent CD₃SP): 3,83 s (CH₂); 4,75 d, m, (CH₂);

³J_H,H=6,1 Hz; 5,35 d, m (CH);³J_H,H=16.8 Hz; 5,38 d, d (CH);³J_H,H=10.3 Hz; J_H,H=1.0 Hz; 6,00 d, d, t (CH);³J_H,H=16,8 Hz;³J_H,H=10.3 Hz;³J_H,H=6.3 Hz; 7,39 m (CH); 7,40 m (CH); 8,73 br. s (CH).

³¹P NMR (relative to 85% H₃PO₄; solvent CD₃SP): -2,48 quin.;²J_P,F=66 Hz.

1. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate, including, at least, the reaction of Tris(perfluoroalkyl)phosphine oxide with an alcohol and an organic base that is stronger than the alcohol.

2. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate, according to claim 1, characterized in that the organic base is used as a compound of General formula (1)

or the General formula (2)

in which X represents a
, ,or,
Y represents-O-, -S-, -Se-, -C(=O)-, -C(=S) -, or-C(=Se)-,
R represents-H for Y≠O and where, in the case of formula (2), all R cannot simultaneously be H,
unbranched or branched alkyl having 1-20 C atoms,
unbranched or branched alkenyl having 2-20 C atoms and one or more double bonds,
unbranched or branched quinil having 2-20 C atoms and one or more triple bonds or
saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, in particular phenyl, which may be substituted by alkyl groups having 1-6 C atoms,
where the substituents R, in each case, are the same or different,
where the substituents R can be related to each other, forming a pair with a simple or double bond,
where one or more, but not all, of the substituents R may be partially or fully substituted by Halogens, in particular-F and/or-CL, or partially by CN or-NO₂,
and where one or two non-adjacent carbon atoms of the substituent R may be replaced by atoms and/or groups of atoms, which is selected from the group
-O-, -C(O)-, -C(O)O-, -C(O)NH-, -C(O)NR'-, -S-, -S(O)-, -S(O)NH-,
-S(O)NR'-, -S(O)O-, -S(O)₂-, -S(O)₂O-, -S(O)₂NH-, -S(O)₂NR'-, -N=, -N=N-,
-NH-, -NR'-, -PH-, -PR'-, -P(O)R'-, -P(O)R'-O-, -O-P(O)R'-O - I-PR'₂=N-,where R' is a not-, partially or perforated C₁-C₆-alkyl, C₃-C₇-cycloalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted heterocycle.

3. The method according to claim 1 or 2, characterized in that the organic base is used as a compound which is chosen from the group comprising (C₂H₅)₃N, (C₂H₅)₂NH, (C₂H₅)₃R, (C₂H₅O)₃R, (C₄H₉)₃R, CH₃-S-CH₃, (CH₃)₂N-C(O)-N(CH₃)₂With₆H₅-Se-C₆H₅, guanidine, pyridine, imidazole, N-Mei, benzoxazole, benzothiazole, pyrrolidine, piperidine, piperazine, aniline, N,N-dimethylaniline, benzylamine, N-ethylbenzylamine or diphenylsulfide.

4. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate according to claim 1 or 2, characterized in that the aliphatic alcohol use alcohol.

5. The method according to claim 1 or 2, characterized in that as alcohol is used as a compound which is chosen from the group comprising methanol, ethanol, isopropanol, n-propanol, butanol, hexanol and benzyl alcohol.

6. The method according to claim 1 or 2, characterized in that as alcohol use fluorinated aliphatic alcohol.

7. The method according to claim 1 or 2, characterized in that as the alcohol use of nenasi the military spirit.

8. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate, according to claim 1, characterized in that as Tris(perfluoroalkyl)phosphine oxide using Tris(perfluoroalkyl)phosphine oxide, in which the three performanceline groups are the same or different.

9. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate, according to claim 1, characterized in that as Tris(perfluoroalkyl)phosphine oxide using Tris(perfluoroalkyl)phosphine oxide, in which performanceline groups contain from 1 to 12 C atoms and are unbranched or branched.

10. The method according to claim 8 or 9, characterized in that as Tris(perfluoroalkyl)phosphine oxide is used as a compound which is chosen from the group comprising (CF₃)₃P(O), (C₂P₅)₃R(O), (C₂P₇)₃P(O) or (C₄F₉)₃P(O).

11. Method for producing organic salts, which contain the anion of bis(perfluoroalkyl)phosphinate, according to claim 1 or 2, characterized in that the reaction is carried out at a temperature of from -20 to 200°C.