Ionic liquids ii

FIELD: organic chemistry.

SUBSTANCE: invention relates to new ionic liquids designated for using in electrochemical cells and in organic synthesis. Invention describes ionic liquids of the general formula: K⁺A^- (I) wherein K⁺ represents one of cations of the group consisting of the following formulae: wherein R¹-R⁵ can be similar or different and can be bound to one another by a simple or double bond also, and each of them separately or in common can represent the following values: hydrogen atom (H), halogen atom, (C₁-C₈)-alkyl radical that can be partially or completely substituted with the following groups but preferably with fluorine atom (F), chlorine atom (Cl), N-[C_nF_(2n+1-x)H_x]₂, O-[C_nF_(2n+1-x)H_x], SO₂-[C_nF_(2n+1-x)H_x] or C_nF_(2n+1-x)H_x wherein 1 < n < 6 and 0 < x < 2n+1; A^- means anion taken among the group consisting of [PF_x(C_yF_(2y+1-z)H_z)_6-x]^- wherein 1 ≤ x ≤ 6, 1 ≤ y ≤ 8 and 0 ≤ z ≤ 2y+1. Invention provides the development of ionic liquids showing broad range of liquid state, high thermal resistance and low corrosive activity.

EFFECT: improved and valuable properties of ionic liquids.

3 ex

The invention relates to ionic liquids intended for use in electrochemical elements and in organic synthesis.

Ionic liquids without solvent, or salts that are molten at room temperature, were first described in the patent US 2446331. The disadvantage of these strong acids Lewis sites is that when the contact is present in the atmosphere with moisture, they form toxic gases.

For a long time the research was conducted compounds, which include AlCl₃and 1-ethyl-3-methylimidazole (EMI) chloride. Wilkes and Zaworotko described the original ionic liquids without solvent EMI BF₄and EMI O₂CLO₃in 1992, in J. Chem. Soc., Chem. Commun., p.965. However, these compounds are unsuitable for use as electrolytes in electrochemical elements, because the anions BF₄ ^-and CH₃CO₂ ^-oxidized even at relatively low potentials.

In the patent DE 19641138 described a new class of conductive salts - peralkylated lithium. These salts have high electrochemical stability and low ability to hydrolysis (M. Schmidt and others 10^thInternational Meeting on Lithium Batteries, Como 2000). In cyclic experiments are particularly good results were obtained with these compounds was demonstrated almost complete justicenet.

In the patent US 5827602 described application in electrochemical elements of ionic liquids from a group of salts of pyridinium, pyridazine, pyrimidine, pyrazine, imidazole, pyrazole, thiazole, oxazole and triazole containing the anions imides and methanide. These ionic liquids are characterized by high electrical conductivity, and is therefore particularly well suited for these applications. Their major drawback is that the synthesis of the initial reagents, in particular anions, is an expensive process.

The object of the present invention are ionic liquids with a wide interval a liquid state, high thermal stability and low corrosiveness, and anions, the synthesis of which is cheaper than described in the prototype.

In this invention the objective is achieved through the use of ionic liquids, which are described General formula

where To⁺there is one of the cations is presented below:

where R¹-R⁵may be the same or different and may be connected directly to each other by single or double bonds, and each of them severally or jointly with others accepts the following values:

-N,

- halogen,

is an alkyl radical (C₁-C ), which can be partially or completely substituted by the following groups, preferably F, Cl, N(C_nF_(2n+1-x)H_x)₂, O(C_nF_(2n+1-x)H_x), SO₂(C_nF_(2n+1-x)H_xor C_nF_(2n+1-x)H_xwhere 1<n<6 and 0<x≤2n+1

and

And^-there is an anion selected from the group of compounds described by the following formula:

[PF_x(C_yF_2y+1-zH_z)_6-x]^-

where 1≤x≤6

1≤y≤8 and

0≤z≤2y+1.

These ionic liquids are suitable not only for use as solvents in organic synthesis, but also for use in electrochemical cells. In addition, these ionic liquids suitable for use in the catalysis of chemical reactions. They can also be used as inert solvents for the reactants with high chemical activity. Another field of application of hydraulic fluid.

Found that the hydrophobicity of the compounds proposed in this invention, associated with the use of perforated alkyl chains, with the preferred use of dlinnozvennye perforated alkyl chains. Moreover, anhydrous synthesis minimizes the penetration into a parasitic water.

Another element of novelty lies in the fact that these ionic liquids not cause corrosion, but on the contrary - p is ssively aluminum current collector, which are usually used in electrochemical elements. This property allows you to increase the cyclic stability of the elements. In addition, the application of ionic liquids observed increase in the heat resistance system.

Discovered that the addition of solvents with low viscosity allows to increase the conductivity. Low viscosity combined with high electrical conductivity are a prerequisite for use in electrochemical cells. This invention describes compounds have a wide range of liquid state, which makes them particularly suitable for these applications.

A prerequisite for use in double layer capacitors is high electrical conductivity. This invention describes compounds meet this criterion and can thus be used individually or in mixtures with other solvents or conductive salts. Suitable for these purposes are compounds from the group of organic carbonates (for example, ethylene carbonate resulting, propylene carbonate and derivatives thereof, butylaniline, dimethylcarbonate, diethylcarbamyl, ethylmethylketone etc), esters of organic carboxylic acids (for example, γ-butyrolactone, methylformate, methyl acetate, ethyl acetate, ethylpropane, methylpropionate, methylbutyrate, ethyl butyrate, etc.), amides of the organic carboxylic acids (for example, dimethylformamide, methylformamide, formamide etc), organic esters (e.g., 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, derivatives of tetrahydrofuran, 1,3-dioxolane, dioxane, dioxolane derivatives, etc. or other aprotic solvents such as acetonitrile, sulfolane, dimethylsulfoxide, nitromethane, truefire phosphoric acid, trimethoxymethane, 3-methyl-2-oxazolidinone and so on). Similarly, you can apply a mixture of solvents such as ethylene carbonate resulting/dimethylcarbonate (EC/DMC).

This invention compounds can be used in conventional electrolytes with a common conductive salts. Their content in the mixture can range from 1 to 99%. Examples of suitable electrolytes can be such where the conductive salts belong to the following group: LiPF₆, LiBF₄, LiCIO₄, LiAsF₆, LiCF₃SO₃, LiN(CF₃SO₂)₂and LiC(CF₃SO₂)₃and mixtures thereof.

In addition, to reduce the water content in the electrolyte can be introduced organic isocyanates (DE 19944603).

Complex salts described General formula (DE 19951804)

where:

x and y is 1, 2 or 3,

M^x+- metal ion,

E - one of Lewis sites of acids belonging to the group BR¹R²R³, AlR¹R²R^{3 PR1R2R3R4R5AsR1R2R3R4R5and VR1R2R3R4R5,}

R¹-R⁵may be the same or different, and may be connected directly to each other by single or double bonds, and each separately or in conjunction with other is halogen (F, Cl or Br),

alkyl or CNS radical (C₁-C₈), which may be partially or fully substituted with halogen (F, Cl or Br,

aromatic ring which may have an oxygen connection, from the following groups: phenyl, naphthyl which may be unsubstituted or mono - to polyamidine alkyl group, (C₁-C₈), or halogen (F, Cl or Br,

aromatic heterocyclic ring, which may contain an oxygen connection, from the group consisting of pyridyl, pirila and pyrimidyl, which may be unsubstituted or mono - to polyamidine alkyl group, (C₁-C₈) or F, Cl or Br, and

Z is OR⁶, NR⁶R⁷, CR⁶R⁷R⁸, OSO₂R⁶N(SO₂R⁶)(SO₂R⁷), With(SO₂R⁶)-(SO₂R⁷)(SO₂R⁸or OCOR⁶where

R⁶-R⁸may be the same or different, and may be connected directly to each other through Odie is ary or double bond and each individually, or in combination with other represents hydrogen, or takes the values defined for R¹-R⁵obtained in the reaction of the adduct corresponding boric or phosphoric Lewis acid with the solvent, with the possible presence of imide, matanda or triflate, lithium or tetraalkylammonium.

Borate salts (DE 19959722) with the General formula

in which:

M is metal ion or a tetraalkylammonium, x and y take the values 1, 2 or 3,

R¹-R⁴may be the same or different and represent CNS or carboxyl radicals (C₁-C₃), which can be linked directly to each other by single or double bonds. These borate salts get in the reaction of tetraalkoxysilane lithium or a mixture of 1:1 lithium alkoxide and a borate with a suitable hydroxyl or carboxyl compound in the ratio of 2:1 or 4:1 in an aprotic solvent.

It is also possible presence of additives, such as silane compounds with the General formula

SiR¹R²R³R⁴,

where R¹-R⁴features: N

C_yF_2y+1-H_z

OC_yF_2y+1-zH_z

OC(O)C_yF_2y+1-zH_z

OSO₂With_yF_2U+1-zH_zand

1≤x≤6,

1≤y≤8 and

0≤z≤2y+1, and

R¹-R⁴may be the same or different and represent the th aromatic ring group, consisting of phenyl and naphthyl which may be unsubstituted, monosubstituted or polyamideimide F, CyF_2y+1-zH_zOC_yF_2y+1-zH_z, OC(O)C_yF_2y+1-zH_z, OSO₂C_yF_2y-1-zH_zor N(C_nF_2n+1-zH_z)₂or aromatic heterocyclic ring from the group consisting of pyridyl, persila or pyrimidyl, each of which can be monosubstituted or polyamidine F, C_yF_2y+1-zH_zOC_yF_2y+1-zH_z, OC(O)C_yF_2y+1-zH_z, OSO₂CyF_2y+1-zH_zN(C_nF_2n+i_zH_z)₂(DE 10027626).

According to this invention, these compounds can also be used in electrolytes, which contain peralkylated lithium with the following formula:

Li⁺[PF_x(C_yF_2y+1-zH_z)_6-x]^-

where 1≤x≤5

3≤y≤8

0≤z≤2y+1

and the ligands (C_yF_2y+1-zH_z) may be the same or different, with the exception of the compounds described by the General formula

Li⁺[PF_a(CH_bF_c(CF₃)_d)_e]^-

where and is an integer from 2 to 5, b=0 or 1, C=0 or 1, d=2 and e is an integer from 1 to 4, under the conditions that b and C are not zero simultaneously, and the sum of a+e is equal to 6, and the ligands (CH_bF_with(CF₃)_dcan be Odie is akovali or different (DE 10008955). The method of producing peralkylated lithium characterized in that at least one of the compounds described by the General formula

H_mP(C_nH_2n+i)_3-mPR(C_nH_2n+1)₃

Cl_mP(C_nH_2n+1)_3-m,

F_mP(C_nH_2n+1)_3-m,

Cl_oP(C_nH_2n+1)_5-o,

F_oP(C_nH_2n+1)_5-o,

each of them

0<m<2, 1<n<8 and 0<<4,

foryouth by electrolysis in hydrogen fluoride, the mixture of products of fluorination separated by extraction, phase separation and/or distillation are obtained reaction of fluorinated alkylphosphine and a mixture of lithium fluoride, aprotic solvent in the absence of moisture, and the resulting salt is purified and isolated by conventional methods.

According to this invention, these compounds can also be used in electrolytes, which contain a salt with the formula

Li[P(OR¹)_a(OR²)_b(OR³)_c(OR⁴)_dF_e],

in which 0<a+b+c+d≤5 and a+b+c+d+e=6, a R¹-R⁴independently from each other, may represent an alkyl, aryl or heteroaryl radicals, and at least two of R¹-R⁴can be connected directly to each other by single or double bonds (DE 10016801). Connections can be is Holocene in the reaction of phosphorus compounds (V), described General formula

P(OR¹)_a(OR²)_b(OR³)_c(OR⁴)_dF_e,

in which 0<a+b+c+d<5 and a+b+c+d+e=5, and R¹-R⁴correspond to the definitions given above, with lithium fluoride in the presence of organic solvents.

The electrolyte may also be present ionic liquid with General formula

K⁺A^-

in which:

To⁺represents one of the cations of the following groups:

where R¹-R⁵may be the same or different and may be connected directly to each other by single or double bonds, and each individually or together with others, can take the following values:

-N,

- halogen,

is an alkyl radical (C₁-C₈), which can be partially or completely substituted by the following groups: F, Cl, N(C_nF_(2n+1-x)H_x)₂, O(C_nF_(2n+1-x)H_x), SO₂(C_nF_(2n+1-x)H_xor C_nF_(2n+1-x)H_x1where 1<n<6 and 0<x≤2n+1,

and

And^-anion selected from the group consisting of

B(OR¹)_n(OR²)_m(OR³)_o(OR⁴)_p]^-

where 0≤n, m, o, p≤4, and

m+n+o+p=4,

where R¹-R⁴the same or different pairs can be connected to not orestano with each other by means of a single or double bond, and each individually, or in aggregate, is as follows:

the aromatic ring from the group consisting of phenyl, naphthyl, anthracene and phenanthrene, which may be unsubstituted, monosubstituted or polyamideimide groups C_nF_(2n+1-x)H_xwhere 1<n<6 and 0<x≤13, or halogen (F, Cl or Br),

aromatic heterocyclic ring from the group consisting of pyridyl, pirila and pyrimidyl, which may be unsubstituted, monosubstituted or polyamideimide groups C_nF_(2n+1i-x)H, where 1<n<6 and 0<x≤13, or halogen (F, Cl or Br), alkyl radical (C₁-C₈), which can be partially or completely substituted by the following groups, preferably F, CI, N(C_nF_(2n+1-x)H_x)₂, O(C_nF_(2n+1-x)H_x), SO₂(C_nF_(2n+1-x)H_xor C_nF_(2n+1-x)H_xwhere 1<n<6 and 0<x≤13,

or or¹-C₈OR⁴

individually or in the aggregate, represent an aromatic or aliphatic carboxylic, dicarboxylic, oxysulphide or oxycarbonyl radical, which may be partially or fully substituted by the following groups, preferably F, Cl, N(C_nF_(2n+1-x)H_x)₂, O(C_nF_(2n+1-x)H_x), SO₂(C_nF_(2n+1-x)H_xor C_nF_(2n+1-x)H where 1<n<6 and 0<x≤13 (DE 10026565).

According to this invention for reducing the amount of acid in aprotic electrolyte systems in electrochemical elements of the proposed compounds may also be present in the electrolytes containing compounds with the following formula:

NR¹R²R³,

in which

R¹and R²is H, C_yF_2y+1-zH_zor (C_nF_2n-mH_m)X, where X is an aromatic or heterocyclic radical, and

R³represent a (C_nF_2n-mH_m)Y, where Y is a heterocyclic radical, or (C_oF_2o-pH_p)Z, where Z is an aromatic radical,

and where n, m, o, R, u and z satisfy the following conditions:

0≤n≤6,

0≤m≤2n,

2≤o≤6,

0≤R≤2O,

1≤y≤8 and

0≤z≤2U+1.

You can also apply peralkylated with the General formula

Mⁿ⁺[PF_x(C_yF_2y+1-zH_z)_6-x]_n ^-

in which

1≤x≤6,

1≤y≤8,

0≤z≤2y+1,

1≤n≤3, and

Mⁿ⁺- monovalent or trivalent radical, in particular:

NR¹R²R³R⁴,

PR¹R²R³R⁴,

P(NR¹R²)_kR³ _mR⁴ _4-k-m(where k=1-4, m=0-3 and k+m≤4),

(NR¹R²)(NR³R⁴)(NR^{5 6}),

(l)₃, Rb or tropoli,

where R¹-R⁸represent H, alkyl or aryl group, (C₁-C₈), which may be partially substituted with halogen (F, Cl or Br, and Mⁿ⁺excluded values Li⁺, Na⁺Cs⁺, K⁺and Ag⁺. These peralkylated can be obtained in the reaction phosphoranes with fluorides or peralkylated metal fluorides or chlorides in organic aprotic solvents (DE 10038858). The electrolyte may also contain a mixture of the following composition:

a) at least one salt of peralkylated lithium with the General formula

Li⁺[PF_x(C_yF_2y+1-zH_z)_6-x]^-

in which 1≤x≤5,

1≤y≤8 and

0≤z≤2y+1,

and the ligands (C_yF_2y+1-zH_zin each case, may be the same or different, and

b) at least one polymer (DE 10058264).

The electrolyte may also contain tetranitroaniline salts with the General formula

Mⁿ⁺([BR₄]^-)_n,

in which Mⁿ⁺there is monovalent, divalent or trivalent cation,

the ligands R in all cases are the same and represent a (C_xF_2x+1), where 1≤x≤8,

and n=1, 2, or 3 (DE 10055811).

The method of obtaining tetranitroaniline salts characterized in that at least one of soy is ineni with the General formula M ⁿ⁺([B(CN)₄]^-)_nin which Mⁿ⁺and n correspond to the definitions given above, foryouth in the reaction with at least one fluorinating agent in at least one solvent, and the obtained fluorinated compound purified and isolated by conventional methods. The electrolyte may also contain borate salts with the General formula

Mⁿ⁺[BF_x(C_yF_2y+1-zH_z)_4-x]_n ⁺

in which

1<x<3, 1≤y≤8 and 0≤z≤2U+1, and

M is monovalent, divalent or trivalent cation (1≤n≤3)addition of potassium and barium,

in particular

Li,

NR¹R²R³R⁴PR⁵R⁶R⁷R⁸P(NR⁵R⁶)_kR⁷ _mR⁸ _4-k-m(where k=1-4, m=0-3 and k+m≤4), or

C(NR⁵R⁶)(NR⁷R⁸)(NR⁹R¹⁰), where

R¹-R⁴represents a C_yF_2y+1-zH_zand

R⁵-R¹⁰there is N or C_yF_2y+1-zH_zor

aromatic heterocyclic cation, in particular nitrogen and/or oxygen and/or sulfur-containing aromatic heterocyclic cation (DE 10103189). The method of obtaining these compounds is characterized by the fact that

a) carry out the reaction in a mixture of 1:1 between complexes BF₃/solvent and an organolithium compound at low t is mperature, then with a small heated to remove the major part of the solvent and then the solid phase is filtered off and washed with a suitable solvent, or

b) conducting the reaction in 1:1-mixture of lithium salts in a suitable solvent and salts(CF₃)F₃the mixture is stirred at elevated temperature to remove the solvent, then the reaction mixture are added aprotic non-aqueous solvents, preferably those which are used in electrochemical elements, and the resulting mixture is dried, or

b) conducting the reaction in the mixture composition is from 1:1 to 1:1,5 salts(CF₃)F₃with lithium salts in water at elevated temperature, then heated to boiling point and within 0.5 to 2 hours to evaporate the solution, after removal of water to the reaction mixture add aprotic non-aqueous solvents, preferably those which are used in electrochemical elements, and the resulting mixture is dried. The electrolyte may also contain foruminformation salts with the General formula

Mⁿ⁺([PF_x(C_yF_2y+1-zH_z)_6-x]^-)_n,

in which

Mⁿ⁺there is monovalent, divalent or trivalent cation,

1≤x≤5,

1≤y≤8 and

0≤z≤2U+1, n=1, 2, or 3, and the ligands (C_yF_2y+1-zH_zin each case, may be the same or different, with the exception f aralkylated salts, in which Mⁿ⁺is a lithium cation and a salt represented by the following formula:

M⁺([PF₄(CF₃)₂]^-where M⁺=Cs⁺Ag⁺or⁺,

M⁺([PF₄(C₂F₅)₂]^-) where M⁺=Cs⁺,

M⁺([PF₃(C₂F₅)₃]^-) where M⁺=Cs⁺To⁺, Na⁺or para-Cl(C₆H₄N₂ ⁺,

M⁺([PF₃(C₃F₇)₃]^-), where M⁺=Cs⁺To^*, Na⁺pair-Cl(C₆H₄N₂ ⁺or a pair of O₂N(C₆H₄N₂ ⁺(DE 10055812). The method of obtaining these peralkylated salts characterized in that at least one compound with the General formula

H_rP(C_sH_2s+1)_3-r

OP(C_sH_2S+1)₃,

Cl_rP(C_sH_2s+l)_3-r,

F_rP(C_sH_2s+1)_3-r,

Cl_tP(C_sH_2s+1)_5-tand/or

F_tP(C_sH_2s+1)_5-t,

in each case,

0≤r≤2

3≤s≤8 and

0≤t≤4,

foryouth by electrolysis in hydrogen fluoride, the mixture of products of fluorination share and spend the obtained reaction of fluorinated alkylphosphine connection, which is described by the General formula M^{n+/sup> (F-)_nin which Mn+and n correspond to the above compounds in an aprotic solvent or mixture of solvents in the absence of moisture, and the resulting forumilpopolo salt is purified and isolated by conventional methods.}

Compounds according to this invention may be present in electrolytes, which contain foruminformation salt (DE 10109032)with the formula

(M^a+)_b[(CnF_2n+1-rnH_m)_yPF_5-y(CR₁R₂)_xPF_5-y(C_nF_2n+1-mH_m)_y]^(2-) _(a*b/2),

in which

M^a+there is monovalent, divalent or trivalent cation, a=1, 2, or 3, b=2 if a=1, b=2 if a=3, b=1 when a=2 and in each case

1≤n≤8,

0≤m≤2 if n=1 or 2

0≤m≤4 3≤n≤8,

1≤x≤12,

0≤y≤2,

where R₁and R₂in each case, may be the same or different and are selected from the group comprising fluorine substituents, hydrogen, alkyl, foralkyl and perfluoroalkyl, and

where in each case the substituents (C_nF_2n+1-mH_m) may be the same or different. These compounds get in the reaction of at least one fluorine-α,ωbis(alkylphosphate)alkane with at least one fluoride salt, which is described General formula (M^a+) [F^-]_awhere (M^a+and sootvetstvuut above definitions, in solution, allowing you to get forumilpopolo salt, and, if necessary, purify and isolate the latter with conventional methods.

Compounds according to this invention can be used in electrolytes for electrochemical elements, in which the material of the positive electrode consists of a metal substrate with a coating, where the substrate material belongs to the following group: Sb, Bi, Cd, In, Pb, Ga and tin or their alloys (DE 10016024). The method of preparation of these materials for positive electrodes differs in that

a) prepare a suspension or Sol of a metal or alloy substrate in urotropine,

b) suspension emuleret₅-C₁₂-hydrocarbons,

C) the emulsion is precipitated on the substrate made of metal or alloy, and

g) hydroxides or oxyhydroxides metal is transformed into the corresponding oxides by heating system.

Compounds according to this invention can also be used in electrolytes for electrochemical elements, in which the negative electrode is made of conventional intercalation and substituted compounds of lithium, and, furthermore, such that the material of the negative electrodes are composed of a mixture of particles of lithium oxide having a coating of one or more metal oxides (DE 19922522). They may also consist of a mixture of particles of lithium oxide having a coating of one who does more polymers (DE 19946066). Compounds according to this invention can similarly be applied in systems where the negative electrode consists of a mixture of particles of oxide of lithium with one or more kinds of coatings of compounds of alkali metals and metal oxides (DE 10014884). The method of obtaining these materials is characterized by the fact that the particles are suspended in an organic solvent, further to the suspension type suspension alkali metal salts in an organic solvent, and the metal oxide dissolved in an organic solvent, and gidrolizuemye solution, then the particles with the coating agent is dried and calicivirus. Compounds according to this invention can similarly be applied in systems where the material of the positive electrode is doped with tin oxide (DE 10025761). This material is a positive electrode is prepared as follows:

a) to a solution of chloride of tin add urea,

b) to the resulting solution was added methenamine and suitable alloying component

C) Sol obtained emuleret in naphthenic the air,

g) wash the obtained gel and remove the solvent by suction and

d) is dried and heated gel.

Compounds according to this invention can similarly be applied in systems in which the material of the positive electrode includes the restored oxide on the ova (DE 10025762). This material is a positive electrode is prepared as follows:

a) a solution of tin chloride is injected urea,

b) to the resulting solution was added methenamine,

in) emuleret Sol obtained in naphthenic the air,

g) wash the obtained gel and remove the solvent by suction,

d) is dried and heated gel and

e) put the received SnO₂in the flow of the reducing gas adapted for blowing a drying Cabinet.

A common example of the invention is explained in more detail below.

Anion selected from the group consisting of

[PF_x(C_yF_2y+1-zH_z)_6-x]^-

where 1≤x≤6,

1≤y≤8 and

0≤z≤2y+1,

get the method described in DE 19641138.

Cation selected from the group consisting of

prepare by the method described in US 5827602. The reaction between the starting reagents is carried out in an aprotic organic solvent in the temperature range in which the solvent is in a liquid state, for from 0.5 to 12 hours, preferably from 1 to 4 hours.

In order to remove by-products, the mixture is cooled to -30°With, for example up to -10°-20°if a byproduct is LiCl, and fell in the sludge by-product is filtered off, preferably made in the field, and filtered with suction.

The resulting mixture solvent/product can be entered directly into the electrolyte. If necessary, the solvent can also be removed by distillation and the resulting product dried to use in these assignments. The following examples lead to a more detailed explanation of the invention, which however is not restricted by them.

Examples

Example 1

Synthesis of 1-ethyl-3-methylimidazole Tris(pentafluoroethyl)triphosphate

Tris(pentafluoroethyl)triphosphate lithium synthesized according to the method described in DE 19641138. Then hold the reaction product in acetonitrile according to the following reaction equation:

The reaction mixture upon cooling, is subjected to filtration with suction through a glass Frit to remove LiCI, which is formed as a by-product. The solvent is removed by distillation under reduced pressure and the resulting product is 1-ethyl-3-methylimidazole Tris(pentafluoroethyl)triphosphate dried under reduced pressure.

Example 2

Synthesis of 1,2-dimethyl-3-propylimidazolium Tris(pentafluoroethyl)-triphosphate

Tris(pentafluoroethyl)triphosphate lithium synthesized according to the method described in DE 19641138. Next, perform the following reaction of the obtained product in acetonitrile:

The reaction mixture when about is ladanyi subjected to filtration with suction through a glass Frit to remove LiCl, which is formed as a by-product. The solvent is removed by distillation under reduced pressure and the obtained 1,2-dimethyl-3-propylimidazolium Tris(pentafluoroethyl)triphosphate dried under reduced pressure.

Example 3

Synthesis of 1-ethyl-3-methylimidazole Tris(nonattorney)-triphosphate.

Tris(nonattorney)triphosphate lithium synthesized by the same method, and Tris(pentafluoroethyl)triphosphate lithium. Next, perform the following reaction product in acetonitrile:

The reaction mixture upon cooling, is subjected to filtration with suction through a glass Frit to remove LiCI, which is formed as a by-product. The solvent is removed by distillation under reduced pressure and the obtained product, 1-ethyl-3-methylimidazole Tris(nonattorney)triphosphate dried under reduced pressure.

1. Ionic liquid with General formula

where To⁺represents one of the cations of the group consisting of

where R¹-R⁵may be the same or different and may be connected directly to each other by single or double bonds, and each of them separately and together take the following values:

-N,

- halogen,

is an alkyl radical (C₁-C₈), which can be partially or completely substituted by the following groups, preferably F, Cl, N(C_nF_(2n+1-x)H_x)₂, O(C_nF_(2n+1-x)H_x), SO₂(C_nF_(2n+1-x)H_xor C_nF_(2n+1-x)H_xwhere 1<n<6 and 0<x<2n+1, and

And^-there is an anion selected from the group consisting of [PF_x(C_yF_2y+1-zH_z)_6-x]^-where

1≤x≤6,

1≤≤8 and

0≤z≤2y+1.