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-[CnF(2n+1-x)Hx]2, O-[CnF(2n+1-x)Hx], SO2-[CnF(2n+1-x)Hx] or CnF(2n+1-x)Hx wherein 1 < n < 6 and 0 < x < 2n+1; A- means anion taken among the group consisting of [PFx(CyF(2y+1-z)Hz)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 10thInternational 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(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), SO2(CnF(2n+1-x)Hxor CnF(2n+1-x)Hxwhere 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:

[PFx(CyF2y+1-zHz)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,

Mx+- metal ion,

E - one of Lewis sites of acids belonging to the group BR1R2R3, AlR1R2R3 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

CyF2y+1-Hz

OCyF2y+1-zHz

OC(O)CyF2y+1-zHz

OSO2WithyF2U+1-zHzand

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, CyF2y+1-zHzOCyF2y+1-zHz, OC(O)CyF2y+1-zHz, OSO2CyF2y-1-zHzor N(CnF2n+1-zHz)2or aromatic heterocyclic ring from the group consisting of pyridyl, persila or pyrimidyl, each of which can be monosubstituted or polyamidine F, CyF2y+1-zHzOCyF2y+1-zHz, OC(O)CyF2y+1-zHz, OSO2CyF2y+1-zHzN(CnF2n+izHz)2(DE 10027626).

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

Li+[PFx(CyF2y+1-zHz)6-x]-

where 1≤x≤5

3≤y≤8

0≤z≤2y+1

and the ligands (CyF2y+1-zHz) may be the same or different, with the exception of the compounds described by the General formula

Li+[PFa(CHbFc(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 (CHbFwith(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

HmP(CnH2n+i)3-mPR(CnH2n+1)3

ClmP(CnH2n+1)3-m,

FmP(CnH2n+1)3-m,

CloP(CnH2n+1)5-o,

FoP(CnH2n+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)dFe],

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)dFe,

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(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), SO2(CnF(2n+1-x)Hxor CnF(2n+1-x)Hx1where 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 CnF(2n+1-x)Hxwhere 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 CnF(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(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), SO2(CnF(2n+1-x)Hxor CnF(2n+1-x)Hxwhere 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(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), SO2(CnF(2n+1-x)Hxor CnF(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, CyF2y+1-zHzor (CnF2n-mHm)X, where X is an aromatic or heterocyclic radical, and

R3represent a (CnF2n-mHm)Y, where Y is a heterocyclic radical, or (CoF2o-pHp)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+[PFx(CyF2y+1-zHz)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)kR3mR44-k-m(where k=1-4, m=0-3 and k+m≤4),

(NR1R2)(NR3R4)(NR5 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+[PFx(CyF2y+1-zHz)6-x]-

in which 1≤x≤5,

1≤y≤8 and

0≤z≤2y+1,

and the ligands (CyF2y+1-zHzin 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 (CxF2x+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+[BFx(CyF2y+1-zHz)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)kR7mR84-k-m(where k=1-4, m=0-3 and k+m≤4), or

C(NR5R6)(NR7R8)(NR9R10), where

R1-R4represents a CyF2y+1-zHzand

R5-R10there is N or CyF2y+1-zHzor

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+([PFx(CyF2y+1-zHz)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 (CyF2y+1-zHzin 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

HrP(CsH2s+1)3-r

OP(CsH2S+1)3,

ClrP(CsH2s+l)3-r,

FrP(CsH2s+1)3-r,

CltP(CsH2s+1)5-tand/or

FtP(CsH2s+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 Mn+/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

(Ma+)b[(CnF2n+1-rnHm)yPF5-y(CR1R2)xPF5-y(CnF2n+1-mHm)y](2-)(a*b/2),

in which

Ma+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 (CnF2n+1-mHm) 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 (Ma+) [F-]awhere (Ma+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

[PFx(CyF2y+1-zHz)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(CnF(2n+1-x)Hx)2, O(CnF(2n+1-x)Hx), SO2(CnF(2n+1-x)Hxor CnF(2n+1-x)Hxwhere 1<n<6 and 0<x<2n+1, and

And-there is an anion selected from the group consisting of [PFx(CyF2y+1-zHz)6-x]-where

1≤x≤6,

1≤≤8 and

0≤z≤2y+1.



 

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5 cl, 9 tbl, 9 ex

The invention relates to the field of chemistry of heterocyclic compounds, namely the derivative of 1,2,4-triazinones with astragalina and herbicide activities that can be used in agriculture

The invention relates to new compounds of the formula (I), where R0- phenyl, R1- phenyl, heteroaryl, lower alkyl which may be substituted or unsubstituted, R2substituted or unsubstituted phenyl, lower alkyl, R3is hydrogen, acyl group, sulfonylurea group, X and Y independently represent a nitrogen atom or a carbon atom, Z is methylene group

The invention relates to androidiani carboxanilides, compositions based on them and the way to deal with arteriotomy and can be used in agriculture

The invention relates to the derivatives of triazole, exhibiting antifungal activity

FIELD: organic chemistry, pharmacology.

SUBSTANCE: invention relates to compounds of formula I ,

where R(1), R(2), R(3), R(4), R(5), R(6), R(7), R(8), R(30), and R(31) are disclosed in claims. Compound of present invention are particularly useful as new antiarrythmia bioactive substances, in particular for treatment and prophylaxis of atrial arrhythmia (e.g., atrial fibrillation or auricular flutter).

EFFECT: higher efficiency.

13 cl, 18 ex, 1 tbl

The invention relates to imidazole derivative of formula (1), where X, Y, R, R2, R3and R4such as defined in the claims

The invention relates to means for inhibiting the adhesion or migration of cells, or inhibition of VLA-4 receptor, representing the heterocycles of General formula (I), where W means R1-A-C (R13), Y represents carbonyl, Z denotes N(R0), And means a divalent residue of phenylene, divalent (C1-C6)-alkalinity balance, means the divalent (C1-C6)-alkalinity residue which may be substituted (C1-C8)-alkyl, D is C(R2) (R3), E mean R10CO., R and R0independently of one another denote hydrogen, if necessary substituted (C6-C14)-aryl, if necessary substituted heteroaryl, if necessary substituted in the aryl residue (C6-C14)-aryl-(C1-C6)-alkyl or, if necessary, substituted in the heteroaryl residue heteroaryl-(C1-C6)-alkyl, R1means hydrogen, Gets the remainder R28N (R21)-C(O)-, R2means hydrogen, R3means CONHR4, R11NH, R4means (C1-C28)-alkyl, which optionally may be single - or multi-substituted by identical or different residues selected from the range hydroxy (C6-C14)-aryl, R10means hydroxyl or (C1-C6)-alkoxy, R11means R12CO., R12means R15-O-, R13means (C1-C6)-alkyl, R15means R16-(C1-C6)-alkyl, R16means 7-12-membered bicyclic or tricyclic residue, a saturated or partially unsaturated and which may be substituted by one or more identical or different (C1-C4)-alkyl residues, R21means hydrogen, R28means R21, Het denotes a mono - or polycyclic, 4-14-membered, aromatic or non-aromatic cycle, which may contain 1, 2, 3 or 4 nitrogen atom, b, C, d and f independently of one another denote 0 or 1, but at the same time may not mean zero, e, g and h independently of one another denote 0, 1, 2, 3, 4, 5 or 6, in all their stereoisomeric forms and mixtures thereof in any ratio, and their physiologically acceptable salts

The invention relates to new derivatives of phenyl - and aminobenzenesulfonamide formula

< / BR>
where a denotes (R1SO2NR2-), (R3R60NSO2NR2-); X represents-NH-, -CH2- or-OCH2-; Y represents 2-imidazoline, 2-oxazoline or 4-imidazole; R1means (NISS

The invention relates to heterocyclic compounds of the formula I, values radicals cm
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