The method of obtaining benzamide

 

(57) Abstract:

The inventive product-benzamid. Reagent 1: methyl ester benzoic acid, obtained by the interaction of benzoic acid CH3OH in the presence of a strong cation exchanger in the H+form, followed by exposure of the reaction mass to the equilibrium of the esterification reaction is hydrolysis by heating followed by cooling and separation of the cation. Reagent 2: 25% aqueous NH3. Reaction conditions: aq NH3add in the resulting reaction mass and the process is conducted in a homogeneous medium at a mass ratio of benzoic acid: CH3OH :cation: NH3equal 1:(5-10):(0,5-1):(4,7-7), subsequent removal from the reaction mass NH3and CH3OH and distillation of the unreacted methyl ester of benzoic acid. 2 C.p. f-crystals, 1 table.

The invention relates to chemistry, specifically to an improved method of obtaining benzamide.

Known methods for the synthesis of benzamide-based benzonitrile (1-6). Despite the high outputs of the applicability of these methods are limited by the relatively low availability of the source benzonitrile.

Classical methods of obtaining benzamide by fusing benzoic acid or boe is m (10), urea (11), inorganic salts of phosphoric (12) and sulfuric (13, 14) acids require high temperatures, pressure, equipment for operation in harsh environments and difficult to isolate a target product because of the formation of by-products of acids or salts. The methods described complex in technological design and therefore did not find practical application in industry.

In the most comprehensive modern textbook Comprehensive Organic Chemistry emphasizes that "For the synthesis of esters and amides there are three methodological approaches: direct acid catalyzed reaction of an alcohol with an acid, a preliminary transformation of the acid in the reactive derivative and the activation of the alcohol or amine with respect to nucleophilic attack carboxyl ions" (15).

As described in the most authoritative reference books, industrial methods of getting benzamide are the hydrolysis of benzonitrile (16), which in more detail above, the interaction of benzoyl chloride with ammonium carbonate (17, 18) or ammonia (16, 18). The desired benzoyl chloride is produced by interaction of benzoic acid with inorganic acid chlorides.

Thus, the closest proposed spasim by ammonolysis of the latter with an aqueous solution of ammonia (19) (prototype).

The disadvantage of the prototype method is the need to work with benzoyl chloride, with a strong lachrymatory effect and easy course of hydrolysis of benzoyl chloride and the formation of by-products: an equivalent amount of ammonium chloride, a significant amount of benzoic acid and other Conversion of benzoic acid benzoyl chloride is especially a big environmental hazard. These disadvantages become even more crucial from an environmental standpoint, the enlargement of scale benzamide.

The aim of the invention is to provide an environmentally safe method of obtaining benzamide from benzoic acid.

This goal is achieved by a method of obtaining benzamide, namely, that in a solution of benzoic acid in methanol is placed in a strong cation exchanger in the H+form (preferably KU-2-8) and the reaction mixture is usually maintained at a heated, preferably to equilibrium reactions of esterification-hydrolysis, and after cooling and separation of the cation to the filtrate was added an aqueous solution of ammonia, and the resulting homogeneous reaction mixture containing metrogroove methylbenzoate distilled off from the reaction mass with water vapor, benzamid distinguish conventional techniques. Optimal mass ratio of benzoic acid: methanol:cation:aqueous ammonia 25%, equal to 1:(5-10):(0,5-1):(4,5-7).

Thus, in the proposed method all unreacted reagents can be regenerated and used in subsequent cycles. The cation exchange resin after separation from the reaction mass may be used repeatedly without additional processing. Therefore, the proposed method is environmentally safe.

Although melirovanie esters of carboxylic acids is a common method of obtaining amides in organic chemistry and has repeatedly made attempts to apply it to the esters of benzoic acid, low reaction rate and reversibility of the processes are not allowed to rely on its practical implementation for the synthesis of benzamide. This is illustrated by the work of Gordon and co-authors (20, 21) to study the kinetics of different ammonolysis of esters. Unlike esters of fatty acids of a number of esters of aromatic acids, in particular benzoic acid, are virtually inert in the reactions of ammonolysis. In the same conditions, the relative speed of ammonolysis methylbenzoate is only 8% of the speed of AMTO alcohol residue has little effect on reactivity in the reaction of ammonolysis of esters of benzoic acid (21).

Emil Fischer (22) shows that many hours heating ethylbenzoic with a large excess saturated at 0aboutWith alcoholic ammonia at 125aboutWith leads to the formation of benzamide with 5%, and of 17.5aboutC - 17%. In effect described the positive effect of the proposed method is unexpected, and the way to obtain benzamide by ammonolysis methylbenzoate in aqueous ammonia at room temperature could not be offered a priori.

Selection of optimal process conditions, the repeated reuse of the regenerated catalysts unexpectedly allowed to get benzamid with high yield and high quality environmentally friendly and essentially waste-free way.

The interaction of benzoic acid with methanol in the presence of a strong cation exchanger, preferably carried out at boiling reactional mixture, at room temperature, this process takes a long time. Naturally the maximum yield of the target product will take place at equilibrium of the esterification reaction, however, in practice, a balance is unlikely to be reasonable and sufficient 25-35 hours boiling. The mass ratio of benzoic acid: nationals significantly on the speed of the process.

At the stage of ammonolysis temperature increase process certainly increases the speed of ammonolysis, however, even more significantly increased rate of adverse reactions and to obtain the pure target product is not immediately successful, and additional procedures are required to clean it.

Distinctive features of the proposed method to obtain benzamide of benzoic acid is the interaction of benzoic acid with methanol in the presence of a strong cation exchanger and ammonolysis of the resulting methyl ester concentrated aqueous ammonia in a homogeneous reaction medium, it is best at room temperature, the removal of excess amounts of ammonia, methanol and methylbenzoate better when the mass ratio of benzoic acid:methanol:cation:aqueous ammonia 25%, equal to 1:(5-10):(0,5-1):(4,5-7).

P R I m e R s 1-9. To a solution of 30 g of benzoic acid in methanol was added to the resin KU-2-8 and the reaction mixture is boiled for 25-35 h (formation of the methyl ester of benzoic acid can be monitored by titration of unreacted benzoic acid alkali solution). Then the reaction mixture is cooled, the resin is separated, and to the solution was added 25% ammonia solution in water. After vigorously methylbenzoate is distilled off with steam, until the distillate becomes completely transparent. Upon cooling, benzamid crystallizes. Get benzamid with so pl. 127-129aboutC.

After recrystallization from water get benzamid with the content of the basic substance to 99.6 99.8% (the titrimetric after decomposition with alkali followed by distillation of ammonia), the content of benzoic acid is not higher than 0.1% (TLC, titrimetric). The data given in the table.

1. The METHOD of OBTAINING BENZAMIDE interaction of activated derivative of benzoic acid and an aqueous solution of ammonia, characterized in that as an activated derivative of benzoic acid using methyl ester benzoic acid, obtained by the interaction of benzoic acid with methanol in the presence of a strong cation exchanger in the H+form, followed by exposure of the reaction mass to the equilibrium reactions of esterification-hydrolysis by heating and subsequent cooling and separation of the cation exchange resin, the aqueous solution of ammonia is added to the reaction mass and the process is conducted in a homogeneous medium at a mass ratio of benzoic acid : methanol : cation : aqueous ammonia(25%) 1 : 5 - 10 : 0,5 - 1 : 4,5 - 7 accordingly, with the subsequent removal isogeny steam.

2. The method according to p. 1, characterized in that the cation exchange resin used resin KU-2 in the N+form.

3. The method according to PP.1 and 2, characterized in that the process of ammonolysis is carried out at room temperature.

 

Same patents:

The invention relates to methods for new therapeutically active derivatives of benzanilide General formulawhere R1- alkyl WITH4-C18with a linear or branched alkyl group which may have a double bond,

R2is hydrogen, methyl or ethyl,

R3- halogen, alkyl WITH1-C5with a linear or branched alkyl group, N(CH3)2, OS or SY, where Y1-C4alkyl linear or branched chain,

R4and R5each independently is hydrogen, alkyl WITH1-C6with a linear or branched alkyl group or a group -(CH2)m-Z, in which Z is a group of the formula och3, -S(O)qСН3or N(CH3)2q= 0,1 or 2, and m= 2,3 or 4, or Z is a 5 - or 6-membered heterocycle containing nitrogen atom, oxygen or sulfur

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to compounds of the formula (I): wherein Ar represents phenyl substituted with a group taken among isobutyl, benzoyl, isopropyl, styryl, pentyl, (2,6-dichlorophenyl)-amino-group, α-hydroxyethyl, α-hydroxybenzyl, α-methylbenzyl and α-hydroxy-α-methylbenzyl; R represents hydrogen atom; X means linear (C1-C6)-alkylene, (C4-C6)-alkenylene, (C4-C6)-alkynylene optionally substituted with group -CO2R3 wherein R3 means hydrogen atom, group (CH2)m-B-(CH2)n wherein B means oxygen atom; m = 0; n means a whole number 2; or B means group -CONH; m means a whole number 1; n means a whole number 2 and so on; R1 and R2 are taken independently among group comprising hydrogen atom, linear (C1-C4)-alkyl, hydroxy-(C2-C3)-alkyl and so on. Invention proposes a method for preparing compounds of the formula (I). Invention proposes inhibitors of C5-induced hemotaxis of polymorphonuclear leukocytes and monocytes representing (R)-2-arylpropionic acid omega-aminoalkylamides of the formula (I). Also, invention relates to a pharmaceutical composition possessing inhibitory activity with respect to hemotaxis of polymorphonuclear leukocytes and monocytes and comprising compounds of the formula (I) in mixture with suitable carrier. Proposes (R)-2-arylpropionic acid omega-alkylamides are useful for inhibition of hemotaxic activation induced C5a and other hemotaxic proteins.

EFFECT: improved preparing method, valuable medicinal properties of compounds and composition.

18 cl, 3 tbl, 23 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to methods for preparing N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine (nateglinide). Method for preparing nateglinide crystals of H-type is carried out by addition of inorganic acid to reaction mixture containing nateglinide to provide its acidification. The reaction mixture is prepared by interaction of trans-4-isopropylcyclohexylcarbonyl chloride with D-phenylalanine in a mixed solvent consisting of a ketone solvent and water in the presence of alkali. The ratio of water to ketone solvent is from 10:1 to 0.5:1. Temperature of the mixture is brought about to 58-72°C and concentration of ketone solvent - up to value above 8 wt.-% and less 22 wt.-% for carrying out precipitation of nateglinide crystals. Invention proposes variant for preparing nateglinide crystals of H-type. Also, invention proposes crystals of nateglinide of H-type showing average value of longitudinal axis from 1 to 5 mm and that for transverse axis from 0.1 to 0.5 mm. Invention provides enhancing effectiveness in isolation of nateglinide crystals.

EFFECT: improved preparing methods.

10 cl, 1 tbl, 13 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention provides a simple method for preparing high-purity acylphenylalanine useful as starting material for pharmaceutical products. Process comprises Schotten-Bauman reaction stage wherein acid chloride reacts with phenylalanine in mixed solvent consisting of water-miscible organic solvent and water, while maintaining alkali pH (>10) of solvent medium with the aid of potassium hydroxide.

EFFECT: prevented formation of impurities.

13 cl, 4 tbl, 12 ex

FIELD: organic chemistry, detergents.

SUBSTANCE: claimed method includes interaction of ethylene diamine with tetraacetic acid. Obtained reaction mixture is treated with acetic anhydride at elevated temperature and N,N,N',N'-tetraacetylethylene diamine is isolated from reaction mass by crystallization. Reagent interaction is carried out in system of two continuous reactors acting in mixing-displacement regime at continuous raw material feeding such as ethylene diamine into top of the first reactor and acetic anhydride into top of the second reactor. Molar ratio of fresh acetic anhydride to ethylene diamine is 2.05-2.1. Temperature difference between top and bottom parts is maintained from 20 to 30°C for the first reactor and from 20 to 40°C for the second one. Compound of present invention is useful in detergent compositions.

EFFECT: target product of increased yield and purity, simplified process.

1 dwg, 1 tbl, 8 ex

FIELD: industrial organic synthesis.

SUBSTANCE: process involves formic acid-methylamine reaction via intermediate methylammonium formate salt, which is dehydrated in presence of molybdenum trioxide catalyst dissolved in aqueous methylamine and added to formic acid in amount 2.0-4.0 wt % based on the latter. Reaction is carried out for 1-2 h in reactor filled with inert packing material having developed surface without cooling of reaction mixture, whereupon volatile products are distilled away at bottom temperature up to 190°C for 60-90 min. Bottom residue containing catalyst, after isolation of desired product, is returned to reactor.

EFFECT: reduced reaction time, reduced power consumption, improved quality of product obtained at increased yield, and diminished production waste.

5 cl, 8 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of aromatic carboxylic acid aminoanilides, such as 21-chloro-4,41-diaminobenzanilide or bis-(2-chloro-4-aminophenol)terephthalamide used in production of thermostable, refractory and highly strength fibers. Method is carried out by acylation of 2-chloro-4-nitroaniline with 4-nitrobenzoic acid chloroanhydride or terephthaloyl chloride, respectively, in organic solvent medium at heating followed by reduction of formed chloro-substituted nitroanilide of aromatic carboxylic acid in a solvent. The acylation process is carried out in the presence of ferric chloride as a catalyst, at chloroanhydride excess with respect to 2-chloro-4-nitroaniline at graduate increase of temperature up to boiling of reaction mass under atmosphere pressure. Ferric chloride is used as anhydrous FeCl3 or crystal hydrate FeCl3 x 6H2O or an aqueous solution. In the reduction process a mixture of water and dipolar aprotonic solvent is used, and mother solutions after isolation of chloro-substituted nitroanilide and chloro-substituted aminoanilide are recovered to recycle at corresponding step of process. Before recovering to recycle at acylation or reduction step, respectively, mother solutions are treated with activated carbon. Invention provides preparing end products of high quality and decreasing amount of waste.

EFFECT: improved method of synthesis.

6 cl, 1 tbl, 22 ex

FIELD: chemistry.

SUBSTANCE: method to manufacture benzyldimethyl[3-(myristoilamino)propyl]ammonium chloride monohydrate-С26Н47ClN2О·Н2О implies two stages, which are reacting myristic acid followed by the end product formation at the second stage. 3-dimethylaminopropylamide is obtained at the first stage by direct reaction of myristic acid with 3-dimethylaminopropylamine in aromatic hydrocarbons, while end product is obtained at the second stage by direct benzylation in alcohols or ketones.

EFFECT: improved purity of end product and process safety.

3 dwg, 1 ex

FIELD: chemistry.

SUBSTANCE: invention refers to the optically active compounds of bisoxazoline of the formula (1) and the method of their preparation, to the new intermediate products and methods of their preparation, it also refers to cooper asymmetric complex on the basis of the bisoxazoline optically active compound of the formula (1) and the method of preparation of cyclopropalcarbon acids using the asymmetric complex. In the compound of the formula (1) , R1 and R2 are equal and each time stand for C1-6 alkoxy group, C1-6 alkyl group substituted by unsubstituted phenyl group or phenyl group substituted by C1-6 alkyl or C1-6 alkoxy group, R1 and R2 with carbon atom of oxazoline ring, to which they are joined and form cykloalkyl ring which has 3-7 carbon atoms, R3 defines unsubstituted 1-naphthyl group or 2-naphthyl group, or 1-naphthyl group or 2-naphthyl group substituted by at least one C1-6 alkyl group or C1-6 alkoxy group; R4 and R5 are equal and each of them stands for hydrogen atom or C1-6 alkyl group or R4 and R5 with carbon atom, to which they are joined, form cykloalkyl ring which has 3-6 carbon atom and * mean asymmetrical center.

EFFECT: usage of the asymmetrical complex allows getting cyclopropanecarboxylic acid in high yields.

16 cl, 11 ex

FIELD: chemistry.

SUBSTANCE: present invention pertains to the method of making compounds with formula , involving reaction of but-2-enoic acid with chlorotrimethylsilane, bromination of the obtained trimethylsilylcrotonate with N-bromosuccinimide, reaction of the obtained trimethylsilyl-4-bromocrotonate or methyl or ethyl 4-bromocrotonate with dimethylamine so as to obtain 4-dimethylaminocrotonic acid, its separation in form of hydrochloride and chlorination with oxalyl chloride. The method allows for obtaining 4-dimethylamino-2-butenoylchloride, suitable for use as an intermediate compound in the synthesis of pharmaceutically active protein kinase inhibitors.

EFFECT: obtaining the agent, suitable for use as an intermediate compound in the synthesis of pharmaceutically active protein kinase inhibitors.

1 cl, 2 dwg, 3 ex

FIELD: chemistry; food products.

SUBSTANCE: present invention relates to use of N-isobutylamide 2E,4E-decadienoic acid (trans-pellitorine) as an aromatic substance, with a sialagogue but not burning effect in compositions used for food, oral hygiene or consumed for delectation, where trans-pellitorine is used in amounts of 20 parts/million in terms of the total mass of the composition. The invention also relates to the aromatic composition, with a sialagogue but not burning effect, containing trans-pellitorine in amounts of 20 parts/million in terms of the total mass of the composition, as well as to the method of obtaining trans-pellitorine. The invention also pertains to the method of obtaining N-isobutylamide 2E,4E-decadienoic acid.

EFFECT: obtaining a substance with sialagogue and/or irritant effect, as well as a wide neutral aromatic profile.

6 cl, 7 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes acylated 6,7,8,9-tetrahydro-5H-benzocycloheptenylamines of the general formula (I): wherein R1 and R4 mean independently hydrogen atom (H), (C1-C10)-alkyl monosubstituted with fluorine atom (F); R2 and R3 mean independently H and (C1-C10)-alkyl; A means -CH, -CHOH; each among B, C and D means -CH2; R5 means possibly substituted phenyl or group Hetar. Also, invention describes method for synthesis of indicated compounds and a pharmaceutical preparation designated for stimulation of expression of endothelial NO-synthase. Nitrogen oxide (NO) released by endothelial tissue displays important significance in function of some main mechanisms of cardiovascular system. Nitrogen oxide exerts the vasodilating effect and inhibits platelets aggregation, adhesion of leukocytes to endothelial tissue and proliferation of smooth muscle cells in internal envelope of blood vessels.

EFFECT: valuable medicinal properties of compounds and pharmaceutical preparations.

16 cl, 1 tbl, 152 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: invention relates to novel compounds -acidified arylcycloalkylamins of formula I in any of their stereoisomeric forms or in form of their mixture in any ratio, or their pharmaceutically acceptable salts, where in formula I : R1 represents aryl, not obligatory substituted with one or two similar or different substitutes, selected from group that includes C1-C6-alkyl and halogen; R2 represents aryl or heteroaryl, which represents residue of 5-6-member aromatic monocyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom and/or 1 sulfur atom or oxygen atom, or residue of 9-10-member aromatic bicyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom, each of which is unsubstituted or contains 1-3 similar or different substitutes, selected from group, consisting of halogens, NH2, unsubstituted C1-C10-alkyl, C1-C10 -alcoxy, C1-C10-alkylamino and di(C1-C10-alkyl)amino, and at least monosubstituted C1-C10-alkyl, etc., n represents 1, 2, 3 or 4. Invention relates to pharmaceutical composition, stimulating expression of endothelial NO synthase, based on said compounds, as well as application of compounds of formula I for production of medication for stimulating expression of endothelial NO-synthase and for treatment of such cardiovascular diseases as atherosclerosis, thrombosis, coronary artery disease, hypertension and impaired cardiac function.

EFFECT: invention ensures enhancing composition and treatment method efficiency.

9 cl, 2 tbl, 41 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the compounds of the formula and their pharmaceutically acceptable salts used as inhibiting agent in the relation of fermentative beta-secretase and it also relates to pharmaceutical compositions based on the formula. In general formula one of RN and RN' represents hydrogen, and another represents - C(=O)-(CRR')0-6R100, or where R4 is chosen from the group including H; NH2; -NR50CO2R51; -(C1-C4)-alkyl-NR50CO2R51; where n7 is equal to 0, 1, 2 or 3; R50 represents H or C1-C6alkyl; R51 is chosen from the group including phenyl-(C1-C4)-alkyl and (C1-C6)-alkyl; X is chosen from the group including -(C1-C6)-alkylidenyl optionally substituted with 1, 2 or 3 metal groups; Z is chosen from the group including bond, SO2, SO and S; Y stands for (C1-C10)-alkyl; R1 represents -(C1-C6)-alkylphenyl where phenyl ring is optionally substituted by 1, 2, 3 or 4 halogen atoms; R and R' independently represent hydrogen or (C1-C6)-alkyl; R2 represents hydrogen; R3 represents hydrogen; Rc represents - (CR245R250)0-4-aryl; where aryl is optionally substituted by 1, 2 or 3 R200; R200 is chosen from the group including (C1-C6)-alkyl optionally substituted with 1, 2 or 3 groups R205; halogen; C=N; R205 stands for halogen; R245 and R250 in each case stands for H; either R245 or R250 are taken together with carbon atom whereto attached to form carbocycle from 3, 4, 5, 6 or 7 carbon atoms; R100 represents 5-6-merous heteroaryl with 1-2 heteroatoms chosen from nitrogen and sulphur, -phenyl-W-heteroaryl where heteroaryl is 5-6-merous ring containing 1-2 heteroatoms, chosen from nitrogen and oxygen and where cyclic parts of each group are optionally substituted by 1, 2 or 3 groups independently chosen among C1-C6alkyl, -(CH2)0-4-CO2-NR105R'105, -(CH2)0-4-SO2-NR105R'105, -(CH2)0-4-N(R150)-CO-R105, -(CH2)0-4-N(R150)-SO2-R105; W represents -(CH2)0-4; R105 and R'105 independently represent (C1-C6)-alkyl optionally substituted with -NH2 or halogen; R150 represents hydrogen.

EFFECT: compounds can be applied to prevent and treat diseases mediated by excess activity of beta-secretase such as Alzheimer's disease.

11 cl, 12 tbl, 3 dwg, 1729 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to novel compounds of formula I: ,

to their synthesis method, a pharmaceutical composition based on said compounds and use of said compounds in making medicinal agents. Substitutes R1, R2, R4, R5, as well as values of A, B, D and n are given in the formula of invention.

EFFECT: obtaining novel compounds of formula I: ,

as well as their pharmaceutically acceptable salts which have inhibitory effect on cholesteryl ester transfer protein (CETP).

14 cl, 251 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a new chemical compound - N-1-[(4-fluorophenyl)-2-(1-ethyl-4-piperidyl)-ethyl]-4-nitrobenzamide hydrochloride of formula Also, the invention refers to drugs.

EFFECT: preparation of a new biologically active compound which exhibits antiarhythmic and antifibrillatory activity.

2 cl, 1 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to hot or sweet flavourants in form of a synthetic amide compound or edible salt thereof in amount ranging from approximately 0.001 parts per million to approximately 100 parts per million. The amide compound has formula

where A is a phenyl or a 5- or 6-member heteroaryl ring selected from a group comprising pyridine, pyrazine, pyrazole, thiazole, furan, thiophene, benzofuran and benzothiophene; m equals 1, 2 or 3, each R1 is independently selected from hydroxyl, fluorine, chlorine, SEt, SCH3, methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy and isopropoxy, or alternatively two R1 are bonded to form a saturated C1-C3 alkylenedioxy ring on the phenyl; and R2 is a C3-C10 branched alkyl. The amide compound also has formula

in which substitutes A, B, R50, R60, R70, R80, n and m assume values given in the formula of invention. The amide compound is also a specific chemical compound.

EFFECT: obtaining hot and sweet taste modifiers and boosters for food and medicinal products.

39 cl, 7 tbl, 180 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method of producing terephthalic acid diamide, which can be used in synthesis of polymers, involving reaction of terephthalic acid and urea in stoichiometric ratio, wherein reaction of initial reagents is carried out in solid phase with thorough mixing and simultaneous grinding, at temperature 180-240°C and pressure created by urea decomposition products equal to 5-15 kg/cm2 for a time defined from the beginning of the reaction, specifically from the moment given temperature and pressure values are achieved to the moment of spontaneous fall of the reaction pressure, and then holding the reaction mixture for 1-3 hours.

EFFECT: simple, single-step method without use of aggressive reagents, characterised by high output of high-quality diamide and no formation of additional wastes.

1 cl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method of producing terephthalic acid diamide which can be used in production of polymers, involving reaction of terephthalic acid with ammonia, wherein the reaction takes place in a fluidised bed at atmospheric pressure, first at temperature (75-80)°C and ratio acid: gaseous ammonia equal to 1:2-5, while feeding ammonia in amount of 22.05-410.3 l/h and carrying out the reaction for 1.0-2.5 hours until formation of a diammonium salt of terephthalic acid, and then at temperature 240-260°C and ammonia flowrate of 2-5 l/h, while feeding nitrogen in an amount which is sufficient to maintain the fluidised bed and carrying out the reaction for 2-4 hours until release of water ceases.

EFFECT: creating an environmentally safe method by avoiding the need to use volatile reactants, which ensures high output (95-98%) and high quality of the end product.

1 cl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted cyclohexylmethyl derivatives, having serotonin, noradrenaline or opioid receptor inhibiting activity, optionally in form of cis- or trans-diastereomers or mixture thereof in form of bases or salts with physiologically compatible acids. In formula (1): R2 denotes H or OH; R1 and R2 together denote or =N-OH, R3 denotes a phenyl residue which is unsubstituted or monosubstituted with a halogen atom or a heteroaryl residue selected from a five-member sulphur-containing heteroaryl such as a thienyl residue or an unsubstituted phenyl residue bonded through a C1-C4alkyl group, R4 and R5 independently denote an unsubstituted C1-C3alkyl or R4 and R5 together denote (CH2)3-6, R8 denotes a linear saturated C1-C4 alkyl group bonded with an aryl, which is unsubstituted or monosubstituted with halogen atoms, R9 denotes a saturated C1-C8alkyl; values of radicals R1, m, n, R6, R7, R10-R13 are given in the claim. The invention also relates to methods of producing compounds of formula (I), a medicinal agent containing said compounds, use of compounds of formula (I) to prepare a medicinal agent for anaesthetic treatment during sharp, neuropathic or chronic pain and for treating depression, urinary incontinence, diarrhoea and alcoholism.

EFFECT: high efficiency of using the compounds.

32 cl, 501 ex, 21 tbl

FIELD: chemistry.

SUBSTANCE: disclosed is a method of producing terephthalic acid diamide (TPADA) which is suitable for use as raw material for producing p-phenylene diamine which can be used in producing polymers. The method involves reaction of terephthalic acid with ammonia gas, the terephthalic acid being obtained from terephthalic acid production wastes which are terephthalic acid with toluic acid impurities and impurities with an unknown composition; removing impurities via extraction thereof with alcohol-containing wastes from production of food-grade alcohol with concentration of ethyl alcohol of 0.1-92% with weight ratio of terephthalic acid production wastes to ethanol of not less than 1.0:0.5 at temperature ranging from 50°C to the boiling point of the mixture of terephthalic acid production wastes and food-grade alcohol production wastes for 15-30 minutes, to obtain pure terephthalic acid and further reaction thereof with ammonia gas in molar ratio of terephthalic acid to ammonia of 1.0:2.1-10.0 at temperature of 40-70°C and pressure of 10.5-20.0 kg/cm2 until formation of a diammonium salt of terephthalic acid, and then at temperature of 220-240°C in an ammonia current until the release of water ceases.

EFFECT: wider raw material base for producing terephthalic acid diamide and enabling recycling of industrial wastes from production of terephthalic acid and food-grade alcohol.

1 cl, 5 ex

Up!