The method of obtaining salts retinylideneproteins

 

(57) Abstract:

The invention relates to a method for producing salts retinylidene, which are intermediates in the production of beta-carotene and other carotenoids, and may find application in pharmaceutical industry. To obtain salts retinylideneproteins to triphenylphosphine in an organic solvent is slowly added sulfuric or p-toluensulfonate at room temperature, then the reaction mass is injected acetate vitamin a and the condensation reaction is carried out at 25 - 50oC. as the organic solvent use C1- C4-alcohols, ethers or chlorinated solvents or mixtures thereof. 3 C.p. f-crystals, 2 tab.

The invention relates to the field of chemistry of carotenoids, in particular to an improved method for producing a salt retinylideneproteins (TFF-salt vitamin A), which is an intermediate in the production of beta-carotene and other carotenoids, and may find application in pharmaceutical industry.

The number of known ways to get TTF-salt vitamin A from vitamin A alcohol, esters of vitamin A or anhydroecgonine and triphenylphosphine (TFF) or salt triphenylphosphine and donors prot - 60 hours

As a donor of protons used mineral (HCl, HBr, HJ, H2SO4) or organic (p-toluensulfonate, benzoylacetonate, trichloroacetic acids or alcoholic solution of hydrogen chloride.

Thus, in [1,2] to a mixture of vitamin A alcohol and triphenylphosphine in alcohol add an alcoholic solution of hydrogen chloride, after which the resulting solution was stirred 24-60 h at 20oC. Obtained TFF-salt was purified from the original product and was isolated in crystalline form.

The disadvantage of these methods is the length and complexity of the process and the use of large quantities of solvents.

Source [3] TTF-Sol vitamin A is obtained from sulfate triphenylphosphine and acetate of vitamin A.

The process is carried out in methanol at 20oC for 20 h Data output and quality of the target product are not listed.

The disadvantage of this method is the necessity of first obtaining a crystalline sulfate triphenylphosphine, which complicates and lengthens the process and leads to a large consumption of solvent.

According to source [4] to a mixture of triphenylphosphine in isopropanol the eyes and poured n-heptane.

The precipitated crystals TFF-salt vitamin A was separated, washed with heptane and dried in a stream of nitrogen. Output TFT-salt vitamin A is 84% of theory.

UV spectrum: 336 nm (750), isopropanol.

The disadvantage of this method is the low yield of the final product, using hardly separated for reuse solvents, due to the need of vysalivaniya and filtration of the crystalline product, as well as the long duration of the process.

The closest to the technical nature of the effect is achieved is a method for the synthesis of sulfonate retinylideneproteins described in [5], example 3.

According to the prototype, the mixture equimolar quantities of triphenylphosphine, vitamin A acetate and p-toluenesulfonic acid in methanol is stirred for 15 h at room temperature, then 2 h at 40oC. After removal of the solvent mass pound 4 times with absolute ether, the ether layer is removed and the residue dried. Received p-toluensulfonate retinylideneproteins, in which the ratio of the specific absorption is significantly lower than for the pure product [4] E1%1Cm= 750.

This suggests that the purity of the obtained product Rav is the ed of all reagents in the prototype of possible temperature rises and the course side processes:

- destruction of vitamin A acid;

- the formation of the products of the interaction of the acid with an organic solvent, etc.

The disadvantage of the prototype is the necessity of separation from the reaction mixture the desired product in crystalline form with the purpose of cleaning, the relatively low yield and quality of the target product, the complexity of the process of its selection and use trudnoperevarivaemym for reuse solvents.

The aim of the invention is to obtain salt retinylideneproteins high quality suitable for further use without isolation from the reaction mass, with a simultaneous increase in its output, simplifying the process and reducing its duration.

This goal is achieved by the proposed method lies in the fact that salt retinylideneproteins obtained by slow addition to triphenylphosphine in an organic solvent donor of protons /sulfuric or p-toluenesulfonic acid at room temperature and then the reaction mixture is injected acetate vitamin A and condensation of the latter with the formed salt triphenylphosphine carried out at a temperature of 25-50o1-C4or esters (ethyl acetate, ethyl formate) or chlorinated solvents (methylene chloride, chloroform, dichloroethane), or a mixture of alcohols C1-C4or a mixture of one of the alcohols C1-C4and ether, or a mixture of one of the alcohols C1-C4and chlorinated solvent.

Slow draining acid to triphenylphosphine at room temperature provides a more complete formation of the salt of triphenylphosphine, eliminates temperature rises and the interaction of the acid with an organic solvent.

The introduction of vitamin A into the reaction mass with salt triphenylphosphine that do not contain free acid, protects vitamin A from destruction in the short-term heating of the reactants to 25 - 50oC.

The combination of these distinctive characteristics contributes to the quality of the finished product, suitable without its isolation and further purification for immediate application in the synthesis of carotene or dyes.

The formation of triphenylphosphonium salt of vitamin A in the stated temperature range 25 - 50oC (letsa as thin-layer chromatography in the absence of the original reagents, and SF-method of control.

The temperature drops below the 25oC slows down the process, it increases the amount of impurities that affect the quality of the product (see tab. 1, examples 21; 22). The temperature increases above the 50oC speeds up the process, however, accelerates the decomposition process as vitamin A and its TFF-salt: the reaction mass darkens, the quality of the finished product is reduced (see table.1, examples 23 and 24).

Fast loss of acid during the formation of the salt of triphenylphosphine leads to uncontrolled growth temperature of the reaction mass, which is accompanied by side processes and ultimately leads to reduced yield and quality of the target product (table. 1, example 25).

Simultaneous mixing of all reagents (acid, triphenylphosphine and vitamin A acetate) the same way as the prototype leads to a temperature jump, the degradation of the reactants and the yield and quality of the target product (table. 1, example 26).

As a result of our research shows that in addition to the methyl alcohol used in the prototype [5] for the synthesis of salts retinylideneproteins suitable alcohols C2-C4or other individual solvents (mixtures of alcohol C1-C4and chlorine-containing solvent (examples 11-14), mixtures of alcohol C1-C4and ether (examples 15, 19) to obtain high yield and quality of the target product.

Similar results were obtained for mixtures of methylene chloride and alcohols C1-C4, dichloroethane and alcohols C1-C4, ethylformate and alcohols C1-C4, ethyl acetate and alcohols C1-C4.

The ratio of reagents (vitamin A, triphenylphosphine, sulfuric acid) in the present method depends on the quality of the vitamin A: Pharmacopoeia (recrystallized, distilled) product reagents are in equimolar quantities; for technical take vitamin A excess triphenylphosphine and sulfuric acid 1:1,05 - 1,12:1,07 - 1,15, depending on the percentage content of vitamin A, the presence of retroporn, anhydroecgonine (see tab. 1 examples 18-20). In such cases, the output TTF salts, vitamin A more than 100% due to transformations in TFF-Sol retro and anhydroecgonine present in the technical product, as observed in example 2 source [5].

Thus, the distinctive features of the proposed method: the procedure for removal of reagents, speed drain acid to triphenylphosphine at room timeou no free acid, - are new and provide a positive effect - increase the yield and quality of salt retinylideneproteins that gives the possibility to use TTF-Sol without selection synthesis --carotene or dyes. This, in turn, simplifies the process and reduces its duration.

The method is as follows.

Charged to the reactor, an organic solvent, and triphenylphosphine, stirred slowly at room temperature add a donor of protons (sulfuric acid or p-toluensulfonate), then add the vitamin A-acetate and heated to 25-50oC in a stream of nitrogen. The reaction mass can be heated up to acetic temperature before adding vitamin A-acetate. The reaction mass is stirred for 1-5 hours depending on the solvent, and then analyze the sample by thin-layer chromatography in the absence of initial reagents and SF-method (defined E1%1Cm). The resulting salt solution triphenylphosphine used in the synthesis of carotene.

The invention is illustrated by the following examples.

Example 1. Charged to the reactor 30 ml of methyl alcohol, the 5.25 g (0.02 Mislata. Upon completion of the discharge of sulfuric acid reaction mass check for the presence of free acid by the reaction of formation of carbanion acetate vitamin A blue-violet color (drip method). In the absence of free acid added to the reactor 6 ,57 g (0.02 mol) of vitamin A acetate, heated the reaction mass to 38 - 40oC in a stream of nitrogen, and maintained at this temperature and stirring for 2 hours, and then analyze the sample by thin layer chromatography in the absence of initial reagents and SF-method for determining the quality of and% of content retinylideneproteins of hydrosulfate.

Get 38,11 g methanolic solution TFF-salt vitamin A content of the basic substance was 31.0% (SF-method), which corresponds to 93.8% of the output on the downloaded acetate vitamin A.

TLC: Rf 0,01; Silufol UV-254. System - hexane-diethyl ether 9:1.

No - acetate vitamin A (Rf = 0.40 in) and triphenylphosphine (Rf = 0.50 in).

Analysis of the dried sample E1%1Cm= 718,5, which corresponds to 95,8% of the content.

Tpl.193-194oC. After recrystallization from acetone TPL194-195oC. UV spectrum: 336 (750) isopropyl alcohol.

Example 2. Carried out analogously to example 1, the Tamina A. The time when education TTF salts of vitamin A to 4 h at a temperature of 38-42oC. Out - of 94.5%, as to 92.4%.

Example 3. Carried out analogously to example 1, except that as the environment of the use of isopropanol. The exposure time in the formation of sulfate triphenylphosphine 30 min, the formation TFF-salt vitamin A - 5 h at a temperature of 37-38oC. Yield reached 91.4%, quality - 96,1%.

Example 4. Carried out analogously to example 1, except that as the environment using a mixture of methanol - isopropanol in a ratio of 1:2. The time when education TTF salts of vitamin A to 3 h at a temperature of 38-40oC. Yield 96.8% of the quality - 96,7%.

Example 5. Carried out analogously to example 1, except that as the environment using a mixture of methanol-ethanol in a ratio of 1: 2. The holding time is 3 hours at a temperature of 40-45oC. Yield of 95.4%, quality - of 94.9%.

Example 6. Carried out analogously to example 1, except that as the environment using ethyl acetate. The time when education TTF salts of vitamin A to 2 h at a temperature of 38-40oC. Output 96,3%, as 97.1 per cent.

Example 7. Carried out analogously to example 1, except that as the environment of the use of chloroform. The time when education TFF-salt vitamin A - 1 h at a temperature of 36-38oC. Yield 93.8% of the quality, the time of exposure in the formation TFF-salt vitamin A - 2 hours at a temperature of 36-40oC. Yield 96%, quality - of 96.5%.

Example 9. Carried out analogously to example 1, except that as the environment of the use of methylene chloride. The time when education TFF-salt vitamin A - 2.5 hours at a temperature of 37-39oC. Yield of 94.9%, as 97 percent.

Example 10. Carried out analogously to example 1, except that as the environment of the use of methylene chloride. The time when education TFF-salt vitamin A - 1.5 hours at a temperature of 25-30oC. Yield 93.8% of the quality is 95.8%.

Example 11. Carried out analogously to example 1, except that as the environment using a mixture of chloroform and methanol in the ratio 1:2, and heating the reaction mass to 38 - 40oC carried out before the addition of vitamin A. the Time when education TFF-salt vitamin A - 2.5 h at 38-40oC. Yield of 92.9%, quality - of 94.9%.

Example 12. Carried out analogously to example 1, except that the acid using p-toluensulfonate, and the environment using a mixture of chloroform and ethanol in the ratio 1:2. The time when education TTF salts, vitamin A, and 3.5 h at 38-40oC. Yield 91.7%, as - 93,8%.

Example 13. Carried out analogously to example 1, except that as the environment using a mixture of chloroform and isopropanol in the ASS="ptx2">

Example 14. Carried out analogously to example 1, except that as the environment using a mixture of chloroform-isobutyl alcohol in a ratio of 1:1. The time when education TFF-salt vitamin A - 3 h at 45-50oC. Yield 95.1% and quality - 94,3%.

Example 15. Carried out analogously to example 1, except that as the environment using a mixture of ethyl acetate: methanol in the ratio of 1:1. The time when education TFF-salt vitamin A - 2.5 hours at 35-36oC. Yield 96%, quality - 95,0%.

Example 16. Carried out analogously to example 1, except that as the environment of the use of isobutyl alcohol is methanol in the ratio of 1:1. The time when education TFF-salt vitamin A - 3 h at 38-40oC. Yield 96.1 per cent, the quality of 94.8%.

Example 17. Carried out analogously to example 1, except that as the environment of the use of ethyl formate. The time when education TTF salts, vitamin A, and 3.5 h at 35-37oC. the Output is 95.2%, quality - 96,0%.

Example 18. Carried out analogously to example 1, except that as the environment of the use of isobutyl alcohol is methanol in the ratio 2:1, and reagents - triphenylphosphine - sulfuric acid - technical vitamin A-acetate 88.4% of the content, the content retroporn - 6.3% are taken in the ratio of 1.10 : 1,14 : 1. The time when education TTF salts of vitamin A for 1.5 h at 38-40oPut a mixture of ethyl acetate - the methanol in the ratio of 1:1, and reagents triphenylphosphine - sulfuric acid - technical vitamin A (88.4% of the content, the content retroporn 6,3%) taken in the ratio of 1.10 : 1,14 : 1. The time when education TFF-salt vitamin A - 2.5 h at 38-40oC. Output 106,1%, quality - 94,3%.

Example 20. Carried out analogously to example 1, except that the medium used is a mixture of Isobutanol and methanol in the ratio of 1:1, and reagents triphenylphosphine - sulfuric acid - technical vitamin (70% content, content retroporn 6,9%) taken in the ratio of 1.12 : 1,15 : 1. The time when education TFF-salt vitamin A - 3 h at 38-39oC. the Output of 105.2%, quality - of 94.8%.

Examples 21 to 27 held in conditions different from the claims.

Example 21. Charged to the reactor 30 ml of methyl alcohol; the 5.25 g (0,02 mol) of triphenylphosphine and slowly poured under stirring at room temperature to 1.96 g (0,02 mol) of sulfuric acid. Analyze as in example 1 and contribute to 6.57 g (0,02 mol) of vitamin A acetate, after which withstand the weight at 18 - 20oC for 18 h, controlling the end of the process by TLC (absence of initial reagents). Get 38,12 g methanolic solution TFF-salt vitamin A content of the basic substance 28,43% (SF-method), is - is 90.2%.

Example 22. Carried out analogously to example 21, just as the environment of the use of a mixture of methanol-isopropanol in a ratio of 1:2, keeping the temperature TTF salts 15oC for 18 h Yield 88%, as TFF-salt vitamin A - 88,2%.

Example 23. As the environment of the use of a mixture of methanol-isopropanol in a ratio of 1:2. Getting sulfate triphenylphosphine carried out analogously to example 1, at a time when education TTF salts, vitamin A mass is heated to a temperature of 52 to 54oC. Yield of 84.0%, as 90%.

Example 24. As the environment of the use of chloroform. Getting sulfate triphenylphosphine carried out analogously to example 1. Education TFF-salt vitamin A is carried out at 52-54oC. Yield 84.4 per cent, as 86%.

Example 25. As the environment of the use of isopropanol. When getting sulfate triphenylphosphine sulfuric acid is drained quickly. Next, the process carried out analogously to example 1. The output of 86.2 per cent, as 90,9%.

Example 26. Mixed simultaneously in methanol triphenylphosphine, n-toluensulfonate and acetate of vitamin A. the Mass is stirred and incubated for 3 h at 38 - 40oC analyze the lack of initial reagents. On the plate Silufol marked degradation products of vitamin A (the size is. 2 shows the results of experiments on the synthesis of carotene from solutions TTF salts, vitamin A, obtained by the claimed method in different solvents or their mixtures (experiments 1-10).

In experiment 11 shows the synthesis of carotene from a solution of p-toluensulfonate retinylideneproteins obtained with the prototype (example 26). Output technical and pharmacopoeial-carotene is lower than in the claimed method, and its quality does not meet the modern requirements of the Pharmacopoeia.

Thus, the new process conditions for the synthesis of salt retinylideneproteins helped to reduce the duration of the process to 1-5 h and increased the yield of the target product up to 96.8% for vitamin A and quality up to 97.1%, which made it possible to use it without releasing the synthesis of carotene.

Bibliography

1. Patent Germany N 1068709, CL 12 25, 07,1960.

2. U.S. patent N 3466335, CL 260-606, 1969.

3. Patent Germany N 1158505, CL 12 25, 07 ,1964.

4. A. Nurrenbach, J. Paust, H. Pommer, Liebigs. Ann.Chem, 1146-1159 (1977).

U.S. patent N3294844, CL 260-606. 5, 1966.

1. The method of obtaining salts retinylideneproteins from vitamin a acetate, triphenylphosphine and sulfuric or n-toluenesulfonic acid in the environment organicheskie at room temperature is slowly added sulfur or n-toluensulfonate, then the reaction mass is injected vitamin a-acetate and condensation of vitamin a-acetate from the resulting salt triphenylphosphine carried out at 25 - 50oC.

2. The method according to p. 1, characterized in that the heating of the reaction mass 25 - 50oC is carried out before or after the addition of vitamin a acetate in the reaction medium.

3. The method according to PP.1 and 2, characterized in that the quality of the environment to obtain salt retinylideneproteins use of individual organic solvents - alcohols C1- C4or esters or chlorinated solvents.

4. The method according to PP.1 and 2, characterized in that the quality of the environment use of organic solvents is a mixture of alcohols C1- C4or a mixture of one of the alcohols C1- C4and ether, or a mixture of one of the alcohols C1- C4and chlorinated solvent.

 

Same patents:

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to new compounds of the general formula: {[R1]yKt}+-N(CF3)2 (I) representing stable salts used as precursors of organic compounds. In the formula (I) Kt means nitrogen atom (N), phosphorus atom (P); R1 means similar or different values and each means unsubstituted or substituted with phenyl (CnH2n+1)-alkyl, unsubstituted phenyl; groups bound with Kt can be similar or different and wherein n = 1-18; y = 4 with exception for (C2H5)4N+ -N(CF3)2. Also, invention relates to a method for preparing these compounds wherein compound of the formula: D+-N(CF3)2 (II) wherein D is taken among group including alkaline metals, or compound of the formula: GN(CF3)2 (IV) wherein G represents fluorinated sulfonamides are subjected for interaction with salt of the general formula: {[R1]yKt}+-E (III) in polar organic solvent and wherein -E means F-, Cl-, Br-, J-, BF-4, ClO-4, AsF-6, SbF-6 or PF-6.

EFFECT: improved method for preparing.

6 cl, 6 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to a method for preparing complexes of 2-isopropoxy-2-methylvinyl trichlorophosphonium hexachlorometals of the general formula: [(I-PrO-C(CH3)=CHP+Cl3)nMCln-6] wherein M means Sn; n = 2; M means Sb or Bi; n = 3. Method involves interaction of diisopropyl ester with phosphorus pentachloride in the inert solvent medium followed by treatment of formed compound with tin, antimony of bismuth dichloride. Before treatment of formed compound with the corresponding anhydrous metal dichloride nitromethane as a polar solvent is added to its in the amount 1.1-1.25 mole per 1 mole of phosphorus pentachloride, and mixture is heated to temperature above 55°C up to formation of the end product. Method provides increasing yield of the end product.

EFFECT: improved preparing method.

3 ex

FIELD: reduction of ferric sulfide deposits in pipe lines.

SUBSTANCE: proposed method consists in bringing the inner surfaces of pipe in contact with composition prepared from aqueous solution containing the compounds given in formula (I): , where X is anion whose valence "n" is selected from definite group and at least one amine selected from group including alkyl amines, dialkyl amines, alkylen diamines, cycloalkyl amines or their conjugates with acids. According to another version, use is made of composition containing tris(hydroxymnethyl) phosphine, at least one amine or its conjugate with acid and solvent. In presence of composition, fast complexation takes place; as a result, ferric sulfide deposits are dissolved and are removed from pipe.

EFFECT: possibility of using safe, available and inexpensive materials ensuring deposition of polymers.

72 cl, 1 tbl

FIELD: biology, medicine, organic chemistry.

SUBSTANCE: invention proposes compound of the general formula (I): wherein A means effector group; L means a linker link; B represents Skulachev-ion Sk or charged hydrophobic peptide. Compound can be used in preparing a pharmaceutical composition for target (directed) delivery of active substances in mitochondria carried out by electrochemical potential of hydrogen ions into mitochondria. Also, invention can be useful in treatment of diseases and states associated with disturbance of normal function of mitochondria, in particular, diseases associated with increased formation of free radicals and active forms of oxygen. The claimed invention owing to directed accumulation of biologically active substance in mitochondria provides enhancing the effectiveness of substance, to decrease total dose, probability and strength of adverse effects.

EFFECT: improved and valuable properties of method and pharmaceutical composition.

26 cl, 14 dwg, 16 ex

FIELD: chemistry.

SUBSTANCE: in phosphazene, applied on carrier, catalyst for cyclic monomer polymerisation or for substituent substitution in compound or for carrying out reaction with formation of carbon-carbon bond, carrier is insoluble in used solvent and has group, which is able to form bond with group described with general formula (1) where n is integer in interval from 1 to 8 and represents number of phosphazene cations, Zn- is anion of compound, containing atoms of active hydrogen in form obtained as result of release of n protons from compound, which contains atoms of active hydrogen, in which there are , at most, 8 atoms of active hydrogen; each of a, b, c and d represents positive integer equal 3 or less; R represents similar or different hydrocarbon groups, containing from 1 to 10 carbon atoms, and two R, located on each common nitrogen atom, can be bound with each other with formation of ring structure; R1 represents hydrogen atom or hydrocarbon group, containing from 1 to 10 carbon atoms; D represents direct bond or divalent group able to bind N with carrier. Described are phosphazene compound and phosphazene salts and methods of cyclic monomer polymerisation, substitution of substituent in compound and carrying out of reaction with formation of carbon-carbon bond using applied on carrier catalyst. According to invention method polymerisation of cyclic monomers, substitution of substituents, reactions with formation of carbon-carbon bond, etc. can be carried out with extremely high efficiency.

EFFECT: increase of efficiency of carrying out different organic reactions and absence of activity decrease even after removal and re-use of catalyst, economic benefit.

10 cl

FIELD: chemistry.

SUBSTANCE: invention refers to organic chemistry, namely, to method of production of functionally substituted fullerenes to be applied as complexing agents, sorbents, biologically active compounds, as well as for production of new materials with specified electronic, magnetic and optical properties. Substance of the method consists in production of 2,3-fullero[60]-7-phenyl-7-phosphabicycklo[2.2.1]heptanes of formula (I) as resulted from reaction of fullerene C60 and phenylphospholane with catalyst Cp2TiCl2 added in toluol medium at temperature 140-160°C within 4-8 hours.

EFFECT: new method of selective production of functionally substituted fullerenes with end product yield 46-68%.

9 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: present invention concerns the salts containing bis(trifluoromethyl)imide anions and saturated, partially or completely unsaturated heterocyclic cations, method of production and application thereof as ionic liquids.

EFFECT: production of new salts to be used as ionic liquids.

19 cl, 5 ex

FIELD: chemistry.

SUBSTANCE: claimed invention relates to copolymers of diallylaminophosphonium salts with sulphur dioxide demonstrating antimicrobial activity with respect to a number of bacteria, as well as to yeast-like fungi and spores, and can be applied as antiseptic and disinfecting means. Claimed copolymers of diallylaminophosphonium salts with sulphur dioxide aree characterised by general formula where A=Cl- or BF4-. They are soluble in methanol, DMSO, DMFA or if A=Cl- are soluble in water. They are obtained by copolymerisation of equimolar amounts of sulphur dioxide and diallylaminophosphonium salt, selected from tris(diethylamino)diallylaminophosphonium chloride or tris(diethylamino)diallylaminophosphonium tetrafluoroborate.

EFFECT: obtaining novel efficient and low-toxic compounds which do not cause corrosion of processed metals.

2 cl, 3 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to ionic liquids based on a cation of formula (1): where substituting groups R1-R9 are selected from hydrogen, alkyl; any carbon atom in R1-R9 can be substituted with a -O-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2- or -SO3- group; X is S, O or C; R8 and R9 exist only when X is carbon; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(FSO2)3C]-, [RCH2OSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [B(OR)4]-, [N(CF3)2]-, [N(CN)2]-, [AlCl4]-, PF6-, BF4-, SO42-, HSO4-, NO3-; where R is hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, Rf is a fluorine-containing substituting group.

EFFECT: obtaining new ionic liquids with improved electrochemical properties.

15 cl, 18 ex, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to ionic liquid used in electrical energy accumulation devices and as a solvent which contains a cation of general formula where X1, X2 and X3 denote N, O, S or C; R1-R11, X1, R1, R2 and R3, X2, R6, R7 and R8, X3, R9, R10 and R11 can form ring structures; the anion is selected from [RSO3]-, [RfSO3]-, [(RfSO2)2N]-, [(RfSO2)3C]-, [(FSO2)3C]-, [ROSO3]-, [RC(O)O]-, [RfC(O)O]-, [CCl3C(O)O]-, [(CN)3C]-, [(CN)2CR]-, [(RO(O)C)2CR]-, [R2P(O)O]-, [RP(O)O2]2-, [(RO)2P(O)O]-, [(RO)P(O)O2]2-, [(RO)(R)P(O)O]-, [Rf2P(O)O]-, [RfP(O)O2]2-, [B(OR)4]-, [N(CN)2]-, [AlCl4]-, PF6-, [RfPF5]-, BF4-, [RfBF3]-, SO42-, HSO4-, NO3- I-, bis(oxalate)borate; R, R1-R11 are selected from hydrogehn, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl and heterocyclyl, halogen, CN- or NO2-; the carbon in R and R1-R11 can be substituted with O-, -Si(R')2-, -C(O)-, -C(O)O-, -S-, -S(O)-, -SO2-, -SO3-, -N= -N=N-, -NH-, -NR'-, -N(R')2-, -PR'-, -P(O)R4 -P(O)R'-O-, -O-P(O)R'-O- and -P(R')2=N-; where R' denotes alkyl, fluoroalkyl, cycloalkyl, cycloalkenyl, cycloalkynyl, phenyl or heterocyclyl; Rf denotes a fluorine-containing substitute.

EFFECT: obtaining novel ionic liquids which are stable in liquid state in a wide temperature range.

14 cl, 76 ex, 3 dwg

Up!