The way to obtain methyl ester dichloracetic acid

 

(57) Abstract:

Use: in the production of pharmaceuticals, dyes and pesticides. The inventive product methyl ether dichloracetic acid. B. F. C3O2H4C12. Reagent 1: oxide trichloroethylene. Reagent 2: methanol. Reaction conditions: at 25 - 45oWith the content in the original mass of 0.5 - 5.0 wt.% methyl ester dichloracetic acid. 1 C. p. F.-ly, 1 table.

The invention relates to the production of alilovic esters dichloracetic acid, and more particularly to methods of producing methyl ester dichloracetic acid.

Methyl ether dichloracetic acid is an important intermediate for obtaining medicines, dyes, pesticides and other products.

A method of obtaining methyl ester dichloracetic acid by esterification of Chlorella [1]

The disadvantage of this method is the low yield of the target product and the formation of large quantities of toxic waste.

Closest to the claimed method is methyl ether dichloracetic acid (hereinafter MADUK) by reacting oxide trichloroethylene, which can b is s, with methanol with continuous heat dissipation, while the process is conducted at a speed equal to the speed of the heat sink [2]

The process of obtaining MADUK flows through reaction

l2OCl+CH3HE>>Cl2COOCH3+ +HCl

According to the method the reaction is carried out at room temperature, in a large excess of methanol and washing the reaction product from methanol-water.

The disadvantage of this method is the high consumption of methanol, great time of the process, and hence low productivity.

The aim of the invention is to reduce the consumption of methanol and increasing the speed of the process.

This goal is achieved by carrying out the process of interaction between the oxide trichloroethylene with methanol at 25-45aboutWith the presence in the original reaction mass of 0.5-5 wt. MEDOC.

The oxide trichloroethylene can be used in the form of a product of oxidation of trichloroethylene, which includes the oxide trichloroethylene and trichloroethylene.

Typically, the oxidation product of trichloroethylene contains 65-70 wt. oxide trichloroethylene, because the maximum output of the oxide trichloroethylene (when the synthesis of the latter) is achieved when its concentration in cheese is to be a pure oxide trichloroethylene, and use in the synthesis of MADOC raw from the stage oxidation: a mixture of oxide trichloroethylene and trichloroethylene. This technology due to the fact that trichloroethylene is not involved in any reactions when receiving MADUK and much easier is separated from MADUK than oxide trichloroethylene. Selected trichloroethylene at the stage of obtaining MADUK returns to the stage of oxidation.

Based on the foregoing and in the prototype and examples of the claimed method was used, the oxidation product of trichloroethylene, the exact composition of which corresponds to: 67 wt. oxide trichloroethylene and 33 wt. trichloroethylene.

P R I m e R 1 (known way). In a glass reactor equipped with a jacket to remove heat of reaction, stirrer and reflux condenser, download 1115 g oxidation products of trichloroethylene, consisting of 67% oxide trichloroethylene and 33% trichloroethylene, and gradually added with vigorous stirring 272 g of methyl alcohol. Evolved hydrogen chloride absorbs water.

The process is carried out with continuous heat and conduct it at a speed equal to the speed of the heat sink, i.e., under isothermal conditions at a temperature loading of reagents 20aboutC.

After the reactions the cops and the results are presented in the table.

P R I m m e R 2. Under the conditions described in example 1, carried out the reaction of the receipt of MADOC, using as raw materials 747 g oxide trichloroethylene.

The test conditions and the results obtained are presented in the table.

P R I m e R 3. In a glass reactor equipped with a jacket to remove heat of reaction, stirrer and reflux condenser load 1115 g oxidation products of trichloroethylene, consisting of 67% oxide trichloroethylene and 33% of trichloroethylene and containing different amounts of MADOC gradually added with vigorous stirring methyl alcohol. Evolved hydrogen chloride absorb water. The process is carried out with continuous dissipation at 25aboutC. After the reaction (reaction time 4 h) determine the mass of the mixture in the reactor and the contents in it, MADUK, the output MADOC was, 723,6

P R I m e R s 3-16. The process is carried out analogously to example 2, but other values of temperature and carbon concentration MADUK in the original reaction mass. Data examples are given in the table.

P R I m e R 17. Under the conditions described in example 2, the process of becoming MADUK analogously to example 2, but using as feedstock 747 g oxide what s the process temperature and other concentrations of MADOC in the original reaction mass.

The data of examples 17-19 also given in the table.

As follows from the data presented in the table, in the temperature range of 25-45aboutAnd when the content in the original reaction mixture of 0.5-5.0 wt. methyl ester dichloracetic acid reduces the rate of the process from 4.5 to 4-1,5 h, and the amount of methanol with 272 g to 170-162 g while maintaining a high output DHUK (not worse than in the known method). Increasing the temperature up to 25-45aboutWith no introduction in the original reaction mixture of 0.5-5.0 wt. MADUK increases the speed of the process (the time of the reaction is reduced), but the output MADUK reduced in comparison with the known method.

With the introduction of MADOC less than 0.5. and a temperature of 25-45aboutAlso there is an increase in the speed of the process, but also slightly reduces the yield of the target product.

The increase in the concentration of MADOC more than 5 wt. already have no significant impact on the process and not make sense.

Increasing the temperature to 50aboutWith leads to further increase the speed of the process, but significant decrease of output MEDOC.

Therefore, only the process in the temperature range of 25-45aboutAnd concentration is, i.e., to achieve the goal.

Physico-chemical constants obtained MADUK: d 20about/4about1,379-1,381 n20about/D 1,4421

In the case of use as the source of the substance is not pure oxide trichloroethylene, and the product of oxidation of trichloroethylene described above, the product consists of MADOC, methyl alcohol, trichloroethylene and some other substances.

This product is analyzed on the GC Color-500" on the content of MADOC, and then calculate its output.

The allocation of the same MADUK possible in various ways, for example, by distillation.

Distinctive features of the proposed method to obtain methyl ester dichloracetic acid is processing at 25-45aboutWith the content in the original reaction mass (oxidation products of trichloroethylene) 0.5 to 5.0 wt. methyl ester dichloracetic acid.

1. The WAY to OBTAIN METHYL ESTER DICHLORACETIC ACID by the interaction of the oxide trichloroethylene and alcohol, wherein the process is conducted at 25 - 45oWith the content in the original reaction mass of 0.5 - 5.0 wt.% methyl ester dichloracetic acid.

2. The method according to p. 1, characterized in that CTA and trichloroethylene.

 

Same patents:

The invention relates to an improved process for the preparation of diethyldichlorosilane starting compounds to obtain the quinoline-2,3-dicarboxylic acid
The invention relates to organic chemistry, specifically to methods of producing 2-hydroxy-4-(meth)acryloylmorpholine (OMF or OABF)

FIELD: organic chemistry, in particular polymers.

SUBSTANCE: invention relates to new method for production of vic-dichlorofluoroanhydride useful as intermediate of starting monomer for fluorinated polymers with good yield from available raw material. Claimed method includes fluorination of starting material (I): (RH1-EH1-)CRH2RH3CH2-0CORHB in liquid phase to form compound of formula (II): (CF2ClCFCl-EF1-)CRF2RF3CF2-OCORFB; ester bond splitting of formula (II) in gaseous phase under solvent absence to form compound of formula (III): (CF2ClCFCl-EF1-)CRF2RF3COF or compound of formula (III) and compound of formula (IV): FCORFB, wherein RH1 is CX1X2ClCX3Cl- or CClX4=CCl, wherein each X1-X4 independently is hydrogen; RH2 and RH3 independently are hydrogen or linear or branched alkyl, optionally substituted with one or more oxygen; EH1 is alkylene, optionally substituted with one or more oxygen; EF1 = EH1 wherein perfluoroalkylene group is optionally substituted with one or more oxygen; RHB = RFB and are linear or branched perfluoroalkyl group, optionally substituted with chlorine one or more oxygen; RF2 is fluorinated RH2; RF3 is fluorinated RH3; with the proviso, that RF2 is fluorinated RH2; RF3 is fluorinated RH3, i.e. RF2 and RF3 represent RH2 or RH3 with at least one fluorinated hydrogen. Also disclosed are new compounds, represented in claims of invention.

EFFECT: new intermediates useful in polymer fluorination.

11 cl, 7 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to industrially useful fluorine-containing compounds such as fluorinated ester compounds and acyl fluoride compounds. Invention, in particular, provides ester compound wherein all C-H groups are fluorinated and which is depicted by general formula RAFCFR1FOCORBF (4), where RAF, CFR1, and RBF are specified elsewhere. Preparation of the ester compound comprises fluorination of ester (4), which has hydroxyl group(s), acyl fluoride group(s) and which has a structure allowing compound to be fluorinated in liquid phase, fluorination being effected in mixture of ester compound and compound having acyl fluoride group(s). Method does not involve environmentally unfriendly solvent such as, for instance, R-113.

EFFECT: enabled fluorination requiring no specific solvent for each reaction and which can be carried out without separation of solvent before next stage.

9 cl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to synthesis of 1,3-dicarboxylic compounds, specifically to a method for synthesis of ethyl ethers of 2-alkyl-4-aryl-3-oxobutanoic acids of general formula:

,

where for R=3,5-Me2C6H3, R1=Me, Et, i-Pr; for R=2,6-Cl2C6H3, R1=Me; for R=2- CI-6-FC6H3, R1=Me, involving acylation of di(bromine-magnesium)salt of ethyl ether of 2-alkyl-3,3-dihydroxyacrylic acid, selected from a group comprising di(bromine-magnesium)salt of ethyl ether of 2-methyl-3,3-dihydroxyacrylic acid, di(bromine-magnesium) salt of ethyl ether of 2-ethyl-3,3-dihydroxyacrylic acid and di(bromine-magnesium) salt of ethyl ether of 2-isopropyl-3,3-dihydroxyacrylic acid, obtained in situ from isopropyl magnesium bromide and the corresponding 2-(carbethoxy)alkanoic acid, arylacetyl chloride, selected from 3,5-dimethylphenylacetyl chloride, 2,6-dichlorophenylacetyl chloride and 2-fluoro-6-chlorophenylacetyl chloride, in molar ratio of arylacetyl chloride: di(bromine-magnesium) salt of ethyl ether of 2-alkyl-3,3-dihydroxyacrylic acid equal to 1: 1.6-2.2, in a medium of anhydrous tetrahydrofuran with subsequent treatment of the reaction mass with aqueous solution of citric acid and extraction of the end product.

EFFECT: high output and purity of disclosed compounds.

7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing low-molecular substituted phenylbenzoates of general formula: , where R1=C3H7O-, C7H15O-, C8H17O-, C7H|5-, R2=-CHO, -CN, -C3H7, X=H-, HO-, through condensation of an acyl chloride of benzoic acid and substituted phenol in a solvent and subsequent separation of the end product, the acyl chloride of benzoic acid used being a compound of formula: , where R1=C3H7O-, C7H15O-, C8H17O-, C7H15-, the substituted phenol used is a compound of formula: , where R2=-CHO, -CN, -C3H7, X=H-, HO-, the solvent used is methylene chloride; condensation is carried out in the presence of triethylamie while exposing the reaction solution to ultrasound at frequency of 25-30 kHz for 1-1.5 hours at room temperature. The end product is obtained with such high purity that it can be used to modify polymer materials without purification. Recrystallisation from ethanol is sufficient to purify the end product when used as a component of liquid crystal compositions.

EFFECT: invention has the following advantages: 3-5 times shorter duration of the condensation process; 1,6 times increase in output of the product; avoiding preparatory operations associated with absolutisation of pyridine; considerably shorter duration and labour input in purification.

1 tbl, 13 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and particularly to a method of producing (2E,4E)-dodeca-2,4-diene-1-ylisovalerate, involving hydroalumination-halogenation of 1-nonyne to obtain (1E)-1-halogennon-1-ene, cross-coupling (1E)-1-halogennon-1-ene with methyl acrylate to obtain methyl ether of (2E,4E)-dodeca-2,4-dienic acid, reducing methyl ether of (2E,4E)-dodeca-2,4-dienic acid with lithium aluminium hydride to obtain (2E,4E)-dodeca-2,4-diene-1-ol, acylating (2E,4E)-dodeca-2,4-dien-1-ol with an acyl chloride of isovaleric acid to obtain (2E,4E)-dodeca-2,4-dien-1-ylisovalerate, where synthesis of methyl ether of (2E,4E)-dodeca-2,4-dienic acid is carried out in by reacting (1E)-1-iodonon-1-ene, which is obtained by hydroalumination-iodination of 1-nonyne, with methyl acrylate in the presence of Pd(OAc)2, K2CO3, Bu4NCl in the medium of N-methyl pyrrolidone with the following molar ratio [(1E)-1-iodonon-1-ene] : [methyl acrylate] : [Pd(OAc)2] : [K2CO3] : [Bu4NCl] : [N-methyl pyrrolidone] = 1:2: 0.02 : 2.5 : 1 : 5.5 for 8 hours in the atmosphere of argon at 18-25C.

EFFECT: method has the following advantages: higher output of (2E,4E)-dodeca-2,4-dien-1-ylisovalarate, and conducting the cross-coupling reaction without heating at 18-25C prevents isomerisation of the (2E,4E)-diene system and increases stereochemical purity of the product.

4 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to application of ester compounds of benzoic acid, taken from group, which includes 1-phenylvinyl 4-methoxybenzoate; 1-(4-methoxyphenyl)-vinyl 4-tert-butyl benzoate, 1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate, 1-phenylvinyl 4-tert-butyl benzoate, 4-benzoyloxy-2-methoxybenzolsulphonic acid, 3-diethylaminophenyl benzoate and 3-(1-pyrrolidinyl) phenyl benzoate and 3-methoxy salicylate, as component for preparing composition for protection of human organism or animal or material from ultraviolet radiation, containing effective quantity at least one of claimed compounds, as component for preparing composition, which is characterised by progressive protection from UV radiation, depending on duration of sun influence and level of sun radiation, as component for preparing composition for individual hygiene, which is characterised by progressive protection from UV radiation, depending on duration of sun influence and level of sun radiation, as component for preparing industrial composition, which is characterised by progressive protection from UV radiation, depending on duration of sun influence and level of sun radiation, and as component for preparing composition, which at photo-regrouping shows quantity of obtained UV-B radiation.

EFFECT: invention also relates to composition for protecting human or animal organism or protection of material from ultraviolet radiation, contains effective quantity of at least one above mentioned ester compound of benzoic acid.

40 cl, 6 dwg, 33 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and particularly to a method of producing (4E)-tridec-4-en-1-ylacetate. (4E)-tridec-4-en-1-ylacetate is a sex pheromone for tomato moth (Keiferia lycopersicella), which is a dangerous pest for solanaceae. Results of the invention can be useful in chemistry and agriculture. The method of producing (4E)-tridec-4-en-1-ylacetate includes alkylating malonic ester with (E)-1,3-dichloropropene to obtain diethyl[(2E)-3-chloroprop-2-en-1-yl]propanedioate, decarbalkoxylating diethyl[(2E)-3-chloroprop-2-en-1-yl]propanedioate to obtain ethyl(4E)-5-chloropent-4-enoate, Fe-catalysed cross-coupling of the ethyl(4E)-5-chloropent-4-enoate with octylmagnesium bromide to obtain ethyl(4E)-tridec-4-enoate, reducing the ethyl(4E)-tridec-4-enoate to obtain (4E)-tridec-4-en-1-ol, acetylation of the (4E)-tridec-4-en-1-ol to obtain (4E)-tridec-4-en-1-ylacetate. According to the invention, Fe-catalysed cross-coupling of ethyl(4E)-5-chloropent-4-enoate with octylmagnesium bromide to obtain ethyl(4E)-tridec-4-enoate is carried out in the presence of a Fe(acac)2Cl catalyst in a mixture of tetrahydrofuran and N-methylpyrrolidone, wit the following molar ratio of reactants [(ethyl(4E)-5-chloropent-4-enoate]:[octylmagnesium bromide]:[Fe(acac)2Cl]:[tetrahydrofuran ]:[N-methylpyrrolidone]=1:1.15:0.01:12:7 for 30 min at 0-5C.

EFFECT: advantage of the disclosed method is higher output of (4E)-tridec-4-en-1-ylacetate.

3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for the production of 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate, comprising an interaction under reaction conditions between 5-tert-butyl-3-methylcatechol (BMC) and triethylamine and a member selected from the group consisting of an aromatic carboxylic acid and an aromatic carboxylic acid derivative, where the derivative of the aromatic carboxylic acid is an aromatic acyl halide, an aromatic anhydride, an aromatic carboxylate salt or any combination thereof; and where the aromatic carboxylic acid is benzoic acid; and forming a composition comprising 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate (BMPD). Synthesis pathways for a precursor to 5-tert-butyl-3-methyl-1,2-phenylene dibenzoate are provided. The precursor is 5-tert-butyl-3-methylcatechol.

EFFECT: simple and cost-effective method with high yield.

10 cl, 2 dwg, 6 ex

FIELD: chemistry.

SUBSTANCE: claimed invention relates to substituted aromatic phenylenediether of structure

,

in which groups R1-R14 are similar or different , group R1 does not represent isopropyl or tertiary alkyl group, and each of groups R1 and R3 is selected from the group, consisting of non-substituted alkyl group, containing from 1 to 20 carbon atoms, non-substituted alkenyl group, containing from 1 to 20 carbon atoms, halogenated hydrocarbon group, halogen atom, silicon-containing hydrocarbon group and their combinations; and each of groups R2, R4 and R5-R14 is selected from the group, consisting of hydrogen atom, non-substituted hydrocarbon groups, consisting from 1 to 20 carbon atoms, halogen atom and their combinations, on condition that R2 and R4 do not represent bromine simultaneously. Invention also relates to substituted aromatic phenylenediether of structure (II), in which groups R1-R14 are similar or different, group R2 represents alkyl group, containing from 2 to 20 carbon atoms, and each of groups R5-R14 is selected from the group, consisting of hydrogen atom, non-substituted hydrocarbon group, containing from 1 to 20 carbon atoms, halogenated hydrocarbon group, halogen atom, silicon-containing hydrocarbon group and their combinations; and all groups R2, R7 and R12 do not represent tert-butyl groups simultaneously. Invention also relates to substituted aromatic phenylenediether of structure (II), in which groups R1-R14 are similar or different, each of groups R1, R3, R4 represents hydrogen atom, group R2 represents hydrocarbon group, containing from 1 to 20 carbon atoms, at least, one of groups R7 and R12 is selected from the group, consisting of halogen atom, primary hydrocarbon group, containing from 1 to 20 carbon atoms, which can optionally contain halogen or silicon atoms or alkoxygroup as substituents, and secondary hydrocarbon group, containing from 1 to 20 carbon atoms, which can optionally contain halogen atoms, silicon atoms or alkoxygroup as substituents; and each of groups R5-R6, R8-R11 and R13-R14 is selected from the group, consisting of hydrogen atom, non-substituted hydrocarbon group, containing from 1 to 20 carbon atoms, halogenated hydrocarbon group, halogen atom, silicon-containing hydrocarbon group and their combinations.

EFFECT: said compounds are prospective components of improved catalytic systems for production of polymers, based on olefins, which have improved properties.

7 cl, 1 tbl

FIELD: pharmacology.

SUBSTANCE: ophthalmic composition contains a formula compound, where the values for R1 and R2 groups are given in the claims, and an ophthalmologically acceptable carrier. The invention also relates to a method for dry eye treatment, comprising local administration of a therapeutically effective amount of the ophthalmic composition to the eye of the subject in need.

EFFECT: increased efficiency.

20 cl, 6 dwg, 6 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention provides improved process for production of a fluorine-containing compound useful as starting material for manufacture of a variety of fluoropolymers with high output when performing short process and using inexpensive and easily accessible chemicals. Process comprises: (i) interaction of indicated below compound 1 with indicated below compound 2 to form indicated below desired compound 3, which is a compound, wherein content of fluorine is at least 30 wt % and which has hydrogen atom or multiple bond capable of being fluorinated; and (ii) liquid-phase fluorination of compound 3 to give indicated below compound 4 followed by (iii) cleaving group EF in compound 4 to produce compound 5 and compound 6: E1-RA-E1 (1), E2-RB (2), RB-E-RA-E-RB (3),

RBF-EF-RAF-EF-RBF (4), EF1-RAF-EF1 (5),

and RBF-EF2 (6), where RAF represents fluorine-containing bivalent saturated, linear or branched hydrocarbon group optionally containing halogen atom other than fluorine and optionally containing one or several ether oxygen atoms; RA represents group, which is the same as group RAF or bivalent organic group capable of being converted into group RAF using fluorination reaction; RBF represents fluorine-containing polyvalent saturated, linear or branched hydrocarbon group optionally containing halogen atom other than fluorine and optionally containing one or several ether or carbonyl oxygen atoms; RB represents group, which is the same as group RBF or polyvalent organic group capable of being converted into group RBF using fluorination reaction; E1 and E2 are such that, when group E1 is -CH2OH or Q1-CH2OH group, then group E2 is -COX or -SO2X group and, when group E2 is -CH2OH or -Q2-CH2OH group, then group E1 is -COX or -SO2X group, where X is halogen atom and Q1 and Q2 may be identical or different and represent -CH(CH3)- or -CH2CH2- group; E represents group -CH2OCO-, -CH2OSO2-, -Q1-CH2OCO-, -Q2-CH2OCO-, -Q1-CH2OSO2-, or -Q2-CH2OSO2-; EF represents group, which is the same as group E or group obtained by fluorination if group E on conditions that at least one group RAF, RBF, or EF is a group formed by fluorination reaction and groups EF1 and EF2 are groups formed by cleaving group EF. Invention also relates to novel fluorine-containing compounds of formulas 3-12, 3-13, 3-14, 3-15, 3-16, 4-12, 4-13, 4-14, 4-15, 4-16, 5-16, which are indicated in description.

EFFECT: increased resource of raw materials for production of fluoropolymers.

8 cl, 23 ex

FIELD: organic chemistry, in particular polymers.

SUBSTANCE: invention relates to new method for production of vic-dichlorofluoroanhydride useful as intermediate of starting monomer for fluorinated polymers with good yield from available raw material. Claimed method includes fluorination of starting material (I): (RH1-EH1-)CRH2RH3CH2-0CORHB in liquid phase to form compound of formula (II): (CF2ClCFCl-EF1-)CRF2RF3CF2-OCORFB; ester bond splitting of formula (II) in gaseous phase under solvent absence to form compound of formula (III): (CF2ClCFCl-EF1-)CRF2RF3COF or compound of formula (III) and compound of formula (IV): FCORFB, wherein RH1 is CX1X2ClCX3Cl- or CClX4=CCl, wherein each X1-X4 independently is hydrogen; RH2 and RH3 independently are hydrogen or linear or branched alkyl, optionally substituted with one or more oxygen; EH1 is alkylene, optionally substituted with one or more oxygen; EF1 = EH1 wherein perfluoroalkylene group is optionally substituted with one or more oxygen; RHB = RFB and are linear or branched perfluoroalkyl group, optionally substituted with chlorine one or more oxygen; RF2 is fluorinated RH2; RF3 is fluorinated RH3; with the proviso, that RF2 is fluorinated RH2; RF3 is fluorinated RH3, i.e. RF2 and RF3 represent RH2 or RH3 with at least one fluorinated hydrogen. Also disclosed are new compounds, represented in claims of invention.

EFFECT: new intermediates useful in polymer fluorination.

11 cl, 7 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to industrially useful fluorine-containing compounds such as fluorinated ester compounds and acyl fluoride compounds. Invention, in particular, provides ester compound wherein all C-H groups are fluorinated and which is depicted by general formula RAFCFR1FOCORBF (4), where RAF, CFR1, and RBF are specified elsewhere. Preparation of the ester compound comprises fluorination of ester (4), which has hydroxyl group(s), acyl fluoride group(s) and which has a structure allowing compound to be fluorinated in liquid phase, fluorination being effected in mixture of ester compound and compound having acyl fluoride group(s). Method does not involve environmentally unfriendly solvent such as, for instance, R-113.

EFFECT: enabled fluorination requiring no specific solvent for each reaction and which can be carried out without separation of solvent before next stage.

9 cl, 8 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to a method for preparation of multivalent carbonyl compounds and to a novel polyvalent carbonyl compound, which may be useful, for example, as intermediate in production of various fluorinated compounds. Polyvalent carbonyl compound is prepared through economically advantageous way from inexpensive substances and with no need of using any complex synthesis stage. In particular, polyvalent alcohol, including alcohols with at least two structures selected from primary, secondary, and tertiary structures, is brought into reaction with acid halide to form polyvalent ester, which is then fluorinated in liquid phase to form perfluorinated polyvalent ester, in which ester bonds, provided by reaction with primary and secondary alcohols, are further cleaved.

EFFECT: expanded synthetic possibilities in organofluoric compound area.

8 cl, 3 dwg, 2 ex

FIELD: chemical industry; method of production of the fluorine-containing compounds.

SUBSTANCE: the invention is pertaining to the chemical industry, in particular, to the improved method of production of fluorine-containing compounds from the halogen-containing, compounds, preferably, from chlorine-containing compounds due to an exchange of halogen for fluorine at presence of the HF-additional compound of the mono- or bicyclic amine with at least two atoms of nitrogen. At that at least one atom of nitrogen is built in the cyclic system as the fluorating agent; or at presence of anhydrous hydrogen fluoride - as the fluorating agent and the indicated HF-additional compound of the mono- or bicyclic amine as the catalyst. At usage of the applicable solvents the reaction mixtures can be divided into two phases and thus to simplify the reprocessing of the products. The invention also is pertaining to the HF-additional compounds of 1.5-diazabicyclo[4.3.0]non-5-en and N,N-dialkylaminopiridin, where alkyl represents C1-C4alkyl and where the molar ratio of HF to amine makes 1:1, and to HF- additional compounds 1.8- diazabicyclo[5.4.0]undecyl-7-ene, where the molar ratio of HF to amine compounds more than 1:1.

EFFECT: the invention ensures at usage of the applicable solvents to divide the reaction mixture into two phases and thus to simplify reprocessing of the products.

17 cl, 13 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to chemistry of adamantane derivatives, namely, to a novel method for synthesis of 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes of the general formula: wherein Hal means bromine atom (Br); R means hydrogen atom (H), -CH3, -C2H5, -C3H7; Hal means Br; R means -CH3; R1 means -CH3; Hal means chlorine atom (Cl); R means Cl; R1 means Cl that can be used as intermediate compounds used for synthesis of some biologically active substances. Method involves interaction of 1,3-dehydroadamantane with α-halogenalkane carboxylic acids ethyl esters chosen from the following group: ethyl-2-bromoacetate, ethyl-2-bromopropionate, ethyl-2-bromobutyrate, ethyl-2-bromovalerate, ethyl-2-bromo-2-methylpropionate and ethyl-2,2,2-trichloroacetate taken in the mole ratio = 1:(3-5), respectively, in the parent α-halogenalkane carboxylic acid ethyl esters medium, at temperature 50-60°C for 4-6 h. Invention provides expanding assortment of chemical compounds, in particular, synthesis of novel 3-halogen-1-(ethoxycarbonyl)-alkyladamantanes with the high yield.

EFFECT: improved method of synthesis.

6 ex

FIELD: chemistry.

SUBSTANCE: invention pertains to perfection of the method of obtaining alkylsalicylic acids. The method involves reaction of salicylic acid with an olefin, containing at least four carbon atoms, at high temperature in the presence of alkylsulfonic acid as a catalyst. The invention also pertains to a composition for obtaining additives to lubrication oils, containing alkylsalicylic acid obtained using the above mentioned method. The obtained product has low content of alkylphenols and good colour. Its acid number is 60-95% of the theoretical value. The values of the results of PDSC testing (pressure differential scanning calorimetry) and "panel coker" test are comparable with or surpass the corresponding values for the control salicylic detergents produced in the industries.

EFFECT: obtaining a product of alkylation of salicylic acid with low content of alkylphenols and good colour.

20 cl, 12 ex

FIELD: chemistry.

SUBSTANCE: invention relates to field of organic chemistry, namely to additives and/or additions to industrial oils, which are mixtures of fluorine-containing esters of compositions [RFC(O)OCH2C(CH2OH)3:(RFC(O)OCH2)2C(CH2OH)2:(RFC(O)OCH2)3CCH2OH :(RF C(O)OCH2)4C] (at RF= C6F13 component ratio equals 5 : 11 : 15 : 69, at RF=ClC8F16 component ratio equals 4 : 10 : 14 : 72, at RF=C3F7OCF(CF3)CF2OCF(CF3) component ratio equals 2 : 8 : 16 : 74 ); [RFC(O)OCH2C(CH2OH)2C2H5 :(RFC(O)OCH2)2C(CH2OH)C2H5 :(RFC(O)OCH2)3CC2H5] (at RF= C3F7 component ratio equals 3 : 8 : 89, at RF= C4F9 component ratio equals 5 : 10 : 85, at RF= C6F13 component ratio equals 4:10:86, at RF = ClC6F12 ratio equals 6 : 12 : 82, at RF= C8F17 component ratio 4 : 9 : 87, at RF = CIC8F16 component ratio equals 3 : 11 : 86, at R = C3F7OCF(CF3)CF2OCF(CF3) component ratio equals 4 : 12 : 84); [RFC(O)OCH2C(CH2OH)(CH3)2 : (RFC(O)OCH2)2C(CH3)2] (where RF = C3F7 component ratio equals 4 : 96, at R = C4F9 component ratio equals 5 : 95, at RF= C6P13 component ratio equals 3 : 97, at R = CIC6F12 ratio equals 2 : 98, at RF = C8F17 component ratio equals 2 : 98).

EFFECT: simplification of industrial oils with additives and/or additions producing, as well as improvement of those antifriction and antiwear properties.

1 cl, 55 ex, 3 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of regenerating surfactants based on fluorinated acids or their salt from adsorbent particles on which the said surfactants are adsorbed, based on fluorinated acids, involving saturation of adsorbing particles with surfactants based on fluorinated acids or their salt, washing particles of adsorbent on which the surfactant based on fluorinated acid or its salt is adsorbed with water; mixing particles of the adsorbent on which the surfactant based on fluorinated acid or its salt is adsorbed with alcohol or inorganic acid in the presence of water, initiation of etherification of the said surfactant based on fluorinated acid or its salt with the said alcohol to obtain an ether derivative of the said fluorinated surfactant, distillation of the said mixture to obtain a distillate containing the said ether derivative, separation of the said ether derivative from the said distillate and optional return of the remaining distillate to the said mixture and optional conversion of the said ether derivative to the corresponding surfactant based on fluorinated acid or its salt.

EFFECT: efficient method enables use of minimal amount of regenerating liquid and leads to obtaining regenerated particles of adsorbent which can be used repeatedly.

8 cl, 18 ex

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