Dimethacrylic esters of dimerised fatty acid

FIELD: chemistry.

SUBSTANCE: invention relates to novel dimethacrylic esters of dimerised fatty acid used as binding materials when producing various composite materials, in filling compounds and anaerobic sealants. Dimethacrylic esters of dimerised fatty acid have the structural formula: in which R=CH2CH2OCH2CH2; СН2СН2ОСН2СН2ОСН2СН2; (СН2)4; СН2СН2;

EFFECT: improved method.

2 tbl, 7 ex

 

The invention relates to the chemical industry, namely, to obtain new derivatives dimenisonal fatty acids (DIC), which can be used, for example, as a binder in the manufacture of various composite materials, consisting of potting compounds and anaerobic sealants.

Known derivatives dimenisonal fatty acids, representing

the polyamides used as hot melt adhesives (Application Germany No. 4408276, C08L 77/08, publ. 14.09.1995,, Application Germany No. 4408277, C09J 177/00, publ. 14.09.1995,);

- oligoamine and imidazoline used as curing agents and modifiers for epoxy and phenol-formaldehyde resins (Bobylev VA // Composite the world. 2006. No. 4. p.20-24);

- oligoamine used in coatings, lacquers and dyes (Popova T.A., žilina, NV, Radivilov L.A. and other Production oligoimide abroad. Survey information. Ser. "Plastics and synthetic resins". M: niitekhim, 1979, p.32);

- 4-hexyl-3-(octene-2-yl)-5-cyclohexen-1,2-di[N,N-di(2-alkyl/cyclooctylamino)ethyl]deptname used as a hardener and epoxy plasticizer compositions (Patent RF №2331633, SS 251/14, publ. 20.08.2008,);

- 4-hexyl-3-(octene-2-yl)-5-cyclohexen-1,2-di[N,N-di(2-amino-ethyl)]deptname used as a hardener and epoxy plasticizer compositions (Patent RF №2333197, SS 37/16, publ. 10.09.2008,);

- esters dimenisonal fatty acids and alcohols containing From3-C24alkyl groups used as plasticizers thermoplastic polymers (U.S. Patent No. 7285588, SC 5/101, publ. 23.10.2007).

It is also known the use of dimethacrylate ethers of triethylene glycol, diethylene glycol and tetraethyleneglycol in anaerobic compositions (USSR Author's certificate No. 1206271, SS 67/08, publ. 23.01.1986 year). These dimethacrylate esters when used in the composition of the anaerobic sealant compositions do not provide a high strength connection on oily surfaces. For example, anaerobic sealant "Anyterm-8K (TU 2257-338-00208947-2000)containing dimethacrylate, triethylene glycol, has a moment of loosening after 24 hours at 20°C low fat surfaces of 5.3 N·m, and the oily surfaces of 2.6 N·m where durability after unscrewing on the oiled surface is not more than 49%.

Inventive task was to provide new compounds derived dimenisonal fatty acids, which when used, for example, in the composition of anaerobic sealants for engineering would provide a high strength on oily surfaces.

The problem is solved dimethacrylate esters dimenisonal fatty acid which you formula

where R=CH2CH2OCH2CH2; CH2CH2OCH2CH2OCH2CH2; (CH2)4; CH2CH2;

.

Starting materials for the synthesis and properties obtained dimethacrylate esters dimenisonal fatty acids are presented in table 1.

Table 1
Characteristics dimethacrylate esters GK
ExampleSource components for synthesisProperties
The appearance of productThe saponification number, mg KOH/g of productEssential number, mg KOH/g of product
1234567
1Diarizonae fatty acid Diethylene glycol
Methacrylic acid
Viscous liquid brownish color267,10266,381,47991,0023
2Diarizonae fatty acid triethylene glycol
Methacrylic acid
258,58256,421,47901,0106
3Diarizonae fatty acid Butyleneglycol
Methacrylic acid
256,75255,391,48250,9794
4Diarizonae fatty acid Monomethacrylate of ethylene glycol233,40227,621,48240,9981
5Dichlorohydrin dimenisonal fatty acids
Monomethacrylate of ethylene glycol
275,0272,601,48511,0082
6Diarizonae fatty acid Monometer the lat propylene glycol 283,70281,721,47990,9938
7Dichlorohydrin dimenisonal fatty acids
Monomethacrylate propylene glycol
270,85268,221,47820,9922

The structure of the synthesized dimethacrylate esters dimenisonal fatty acids proven data of IR - and NMR-spectroscopy.

The invention allows to achieve the following advantages: the use of dimethacrylate esters dimenisonal fatty acid composition of the anaerobic adhesive and sealant compositions increases the strength clearsilver connections on oily surfaces, while providing high durability on oily surfaces compared to free of grease.

To implement ways to obtain methacrylic esters GC using the following ingredients:

diarizonae fatty acid "Pripol 1013" (dimers of linoleic acid is not less than 97%) - CAS # 61788-89-4;

Dichlorohydrin dimenisonal fatty acids [Fomin E.V., Kursk Y.A., Chervyakova GN. and others Receive dichlorohydrin dimenisonal fatty acids and oligoamine based methods nicotine attorney polycondensation // Journal go active. chemistry. 2008. - T.81. - 4. - S-626];

methacrylic acid - TU 6-01-914-79;

diethylene glycol - GOST 10136-77;

triethylene glycol - TU 6-01-5-88 with ISM. 1, 2;

butyleneglycol (1,4-butanediol) - TU 64-5-105-86;

monomethacrylate ether of ethylene glycol - TU 6-01-1240-80;

monomethacrylate ether of propylene glycol - STP 70-2005 (Federal state unitary enterprise "Institute of polymers");

toluene - GOST 5789-78;

hydroquinone - GOST 2549-60;

n-methoxyphenol - TU 6-09-1248-71;

n-toluensulfonate - TU 6-09-3668-77;

the triethylamine - GOST 9966-88;

sodium hydroxide - GOST 4328-77 with ISM. 1, 2;

sodium chloride - GOST 4233-77;

distilled water - GOST 6709-72.

Getting dimethacrylate esters JC conducted in three ways:

1. Interaction JK with glycol and methacrylic acid.

2. Interaction JK with monoglycol methacrylic acid.

3. The interaction of dichlorohydrin JK with monoglycol methacrylic acid.

where R=CH2CH2OCH2CH2; CH2CH2OCH2CH2OCH2CH2; (CH2)4.

where X=OH or C1; R=CH2CH2;

Example 1. Synthesis of dimethacrylate-based GC, diethylene glycol and methacrylic acid.

In a flask equipped with a stirrer and a nozzle Dean-stark with fridge, placed 100 g (0,18 mol) dimenisonal fatty acid is you, 42 g (0.4 mole) of diethylene glycol, of 34.1 g (0.4 mol) of methacrylic acid, 0.36 g (0,0032 mole) of hydroquinone, 4,4 g (0,0256 mole) n-toluenesulfonic acid and 250 ml (2,35 mole) of toluene, 15 ml in the attachment.

The reaction mixture is heated at a temperature of 120-130°C in the bath and 100-120°C in the reactor for 5-6 hours before the termination of the allocation of water. Several times during the synthesis process, and at the end determine the acid number of the reaction mass of n-toluensulfonate and dimenisonal fatty acid. The contents of the flask at the end of the synthesis poured into a separating funnel, diluted with 300 ml of toluene and 2-3 times washed with 10%aqueous solution of sodium chloride. Then the synthesized product is neutralized calculated amount of sodium hydroxide, then washed with 10%sodium chloride solution and then with distilled water until neutral. The resulting product is filtered through a cloth, add in a 0.06 g (of 0.0005 mole) of hydroquinone and distilled in vacuum toluene at 60-10 mm Hg and a temperature of 50-60°C. After distillation of the toluene, the product was evacuated at 10-5 mm Hg and 50-60°C for 1-2 hours.

The output of the dimethacrylate-based dimenisonal fatty acid, diethylene glycol and methacrylic acid is 78,4%.

;.

The saponification number 267,10 mg KOH/g product is A.

Essential number 266,38 mg KOH/g of product.

Molecular mass 872.

Found, %: C 71,28; N 9,84.

Calculated, %: C 71,60; N 10,10. C52H88O10.

IR-spectrum: characteristic bands of stretching vibrations of ester C-O-C-groups when 1350-1100 cm-1; C=C-bonds at 1640 cm-1C=O-groups associated with a connection (1720 cm-1) and unpaired (band in region ~1740 cm-1); the absorption band deformation vibrations (CH2)ngroups of aliphatic chain at ~725 cm-1.

NMR spectrum: NMR1N (δ, ppm): 0.88 (m, CH3); 1.26 (s, - (CH2)n-); 1.62 (m, CH2); 1.95 (s, OS(O)N3C=CH2); 2.33 (t, CH2C(O)O); 3.61÷3.79 (m, OCH2CH2O); 4.23 and 4.31 (both t, CH2OC(O)); 5.58 and 6.14 (both s,- C=CH2).

Example 2. Synthesis of dimethacrylate-based GC, triethylene glycol and methacrylic acid.

In a flask equipped with a stirrer and a nozzle Dean-stark with fridge, placed 100 g (0,18 mol) dimenisonal fatty acid, 60 g (0.4 mol) of triethylene glycol, of 34.1 g (0.4 mol) of methacrylic acid, 0.36 g (0,0032 mole) of hydroquinone, 4,85 g (0,0282 mole) n-toluenesulfonic acid and 250 ml (2,35 mole) of toluene, 15 ml in the attachment.

Synthesis and further extraction of the product was carried out as described in example 1.

The output of the dimethacrylate-based dimenisonal fatty acid, triethylene glycol and methacrylic acid is 7.2%.

;.

The saponification number 258,58 mg KOH/g of product.

Essential number 256,42 mg KOH/g of product.

Molecular weight of 960.

Found, %: C 69,72; N 9,76.

Calculated, %: C 70,00; N And 10.0. C56H96O12.

IR-spectrum: characteristic absorption bands of C-O-C-groups (1350-1100 cm-1); C=O groups(~1730 cm-1).

NMR spectrum: NMR1N (δ, ppm): 3.66 (s, OCH2CH2(O) and (3.60÷3.77 (m); 4.22 and 4.30 (t, CH2OC(O)).

Example 3. Synthesis of dimethacrylate-based GC, butyleneglycol and methacrylic acid

In a flask equipped with a stirrer and a nozzle Dean-stark with fridge, placed 100 g (0,18 mol) dimenisonal fatty acids, 36,0 g (0.4 mole) of butyleneglycol, to 34.1 g (0.4 mol) of methacrylic acid, 0.36 g (0,0032 mole) of hydroquinone, of 4.25 g (0,0379 mole) n-toluenesulfonic acid and 250 ml (2,35 mole) of toluene, 15 ml in the attachment.

Synthesis and further extraction of the product was carried out as described in Example 1.

The output of the dimethacrylate-based dimenisonal fatty acids, butyleneglycol and methacrylic acid is 84.3%.

;.

The saponification number 256,75 mg KOH/g of product.

Essential number 255,39 mg KOH/g of product.

Molecular weight 840.

Found, %: C 73,93; N 10,19.

Calculated, %: C 74,29; N 10,48. C52H88O8.

IR-spectrum: characteristic for the wasps absorption of C-O-C-groups (1340-1100 cm -1); C=O groups (1730-1715 cm-1).

NMR spectrum: NMR1N (δ, ppm): 0.88 (m, CH3); 1.26 (s, -(CH2)n-);1.62 (m, CH2); 1.70÷1.81 (m, C(O)OCH2CH2CH2CH2O(O)); 1,94 (s, OS(O)CH3C=CH2); 2.29 (t, CH2C(O)O); 4.09-4.21 (m, CH2OC(O)); 5,55 and 6.10 (both s, C=CH2); 4.95÷5.46 and 6.68÷7.10 (both m, CH=CH).

Example 4. Synthesis of dimethacrylate-based GC and monomethacrylates of ethylene glycol.

In a flask equipped with a stirrer and a nozzle Dean-stark with fridge, placed 100 g (0,18 mol) dimenisonal fatty acids, 56,16 g (0,432 mole) of monomethacrylate of ethylene glycol, 0.56 g (0,005 mol) of hydroquinone, 3,90 g (0,0227 mole) n-toluenesulfonic acid and 250 ml (2,35 mole) of toluene, 15 ml in the attachment.

Synthesis and further extraction of the product was carried out as described in example 1.

The output of the dimethacrylate-based dimenisonal fatty acids and monomethacrylates of ethylene glycol is 88.1 percent.

;.

The saponification number 233,40 mg KOH/g of product.

Essential number 227,62 mg KOH/g of product.

Molecular weight of 784.

Found, %: C 73,22; N To 9.93.

Calculated, %: C 73,47; N 10,20. C48H80O8.

IR-spectrum: characteristic frequency C-O-C-groups (1150-1080 cm-1); C=O groups (1730-1715 cm-1).

NMR spectrum: NMR1N (δ, ppm): 0.88 (m, CH3); 1.26 (s, -(HE2)n-); 1.62 (m, With the 2); 1.95 (s, OS(O)N3C=CH2); 2.33 (t, CH2C(O)Oh); 2.53 (m, CH2CH); 4.34 (s, OCH2CH2O); 5.59 and 6.13 (both s, -C=CH2); 6.73÷7.01 (m, CH=CH).

Example 5. Synthesis of dimethacrylate-based GC and monomethacrylate propylene glycol.

In a flask equipped with a stirrer and a nozzle Dean-stark with fridge, placed 100 g (0,18 mol) dimenisonal fatty acids, 62,21 g (0,432 mole) of monomethacrylate propylene glycol, and 0.62 g (0,0055 mole) of hydroquinone, 4,06 g (0,0236 mole) n-toluenesulfonic acid and 250 ml (2,35 mole) of toluene, 15 ml in the attachment.

Synthesis and further extraction of the product was carried out as described in example 1.

The output of the dimethacrylate-based dimenisonal fatty acids and monomethacrylate propylene glycol is 94,5%.

;.

The saponification number 283,70 mg KOH/g of product.

Essential number 281,72 mg KOH/g of product.

Molecular weight 812.

Found, %: C 73,58; N 10,06.

Calculated, %: C 73,89; N 10,34. C50H84O8.

IR-spectrum: characteristic frequency C-O-C-groups (1300-1150 cm-1); C=O groups (1750-1735 cm-1).

NMR spectrum: NMR1N (δ, ppm): 0.88 (m, CH3); 1.26 (s, -(CH2)n-); 1.62 (m, CH3); 1.94 and 1.96 (both s, OS(O)N3C=CH2); 2.33 (t, CH2C(O)O); 2.53 (m, CH2CH=C); 4.00÷4.25 (m, OSN2SNSN3Oh); 5.0÷5.40 (m, OCH2 CHCH3O); 5.59÷5.60 (m, C=CH2); 6.10 and 6.15 (both s, -C=CH2); 6.70÷7.25 (m, CH=CH).

Example 6. Synthesis of dimethacrylate-based dichlorohydrin GC and monomethacrylates of ethylene glycol.

In a flask equipped with stirrer and thermometer, is placed 14.3 g (of 0.11 mol) of monomethacrylate of ethylene glycol dissolved in 260 ml of 2.45 mole) of toluene, and 12.6 g (a 0.125 mole) of triethylamine and with stirring, dropwise, add a solution of 30 g (0.05 mole) of dichlorohydrin dimenisonal fatty acid in 200 ml of 1.9 mole) of toluene. Synthesis is carried out while stirring the reaction mass for 3 hours (the first hour at 20°C, and then 2 hours at the temperature of the water bath 40°C). The formed salt is separated on a filter, SCHOTT, and the filtrate is transferred into a separating funnel and washed several times with water and 20%sodium chloride solution. The resulting product is filtered, add in a 0,197 g (0,0016 mole) of n-methoxyphenol and distilled toluene under vacuum 80-85 mm Hg and a temperature of 50-55°C. After distillation of the toluene, the product was evacuated at 3 mm Hg and 60-65°C for 2-3 hours.

The output of the dimethacrylate-based dichlorohydrin dimenisonal fatty acids and monomethacrylates of ethylene glycol is 87,06%.

;.

The saponification number 275,0 mg KOH/g of product.

Essential number 272,60 mg KOH/g of product.

Molecular weight of 784.

Nage is about, %: 73,18; N 9,94.

Calculated, %: C 73,47; N 10,20. C48H80O8.

IR-spectrum: characteristic frequency C-O-C-groups when 1150-1070 cm-1; C=O groups at 1745-1715 cm-1.

NMR spectrum: NMR1N (δ, ppm): 2.34 (t, CH2C(O)O); 2.55 (m,N2CH=C); 4.33 (s, O(CH2)2O); 5.57 and 6.12 (both s, -C=CH2); 6.69÷7.0 (m, CH=CH).

Example 7. Synthesis of dimethacrylate-based dichlorohydrin GC and monomethacrylate propylene glycol.

In a flask equipped with stirrer and thermometer, is placed 15,84 g (of 0.11 mol) of monomethacrylate propylene glycol dissolved in 260 ml of 2.45 mole) of toluene, and 12.6 g (a 0.125 mole) of triethylamine and with stirring, dropwise, add a solution of 30 g (0.05 mole) of dichlorohydrin dimenisonal fatty acid in 200 ml of 1.9 mole) of toluene.

Synthesis and further extraction of the product was carried out as described in example 6.

The output of the dimethacrylate-based dichlorohydrin dimenisonal fatty acids and monomethacrylate propylene glycol is 85,4%.

;.

The saponification number 270,85 mg KOH/g of product.

Essential number 268,22 mg KOH/g of product.

Molecular weight 812.

Found, %: C 73,66; N 10,10.

Calculated, %: C 73,89; N 10,34. C50H84O8.

IR-spectrum: characteristic absorption bands of C-O-C-groups (1350-1150 cm-1); C=O groups (1740-1715 cm-1).

NMR spectrum: I have R 1N (δ, ppm): 1.95 and 1.97 (both s, OC(O)CH3C=H2); 2.33 (t, CH2C(O)O); 2.54 (m,N2CH=C); 4.00÷4.28 (m, OSN2SNSN3O); 4.99÷5.50 (m, OSN2NCH3O); 5.58÷5.59 (m, -C=OH2); 6.10 and 6.15 (both s, -C=CH2); 6.71÷7.25 (m, CH=CH).

Below are examples of specific applications of the proposed new chemical compounds. However, these examples do not exhaust other possible applications.

The obtained compositions containing synthesized dimethacrylate esters dimenisonal fatty acids, was investigated in anaerobic adhesive compositions in the threaded connection of the bolt-nut. The composition was applied on a fat-free toluene and oily (5%solution engine oil M63G in hexane) screw pair and replaced the nut. After curing of the compositions was measured by the time of unscrewing the threaded connection when compared with industrial sealant manufactured brand "Anyterm-8K (TU 2257-338-00208947-2000)containing triethylene glycol dimethacrylate.

Anyterm-8K
Table 2
The results of tests of anaerobic compositions based dimethacrylate esters dimenisonal fatty acids
ExampleThe time of unscrewing, N is m, after 24 hours at 20°C low fat surfacesThe time of unscrewing, N·m, after 24 hours at 20°C on oily surfacesThe indicator save time unscrewing on oily surfaces compared with fat, %
According to the invention
15,2a 3.975
24,43,784
34,54,089
46,14,066
56,04,676
65,95,280
7the 5.74,274
To compare
5,32,649

Studies have shown that anaerobic compositions containing dimethacrylate esters dimenisonal fatty acids, possess high strength on oily surfaces. Time unscrewing of such compositions is 3.7-5.2 N·m, which is 1.4-2.0 times higher than the "Anathema-8K", obtained on the basis of known dimethacrylate of alkalophiles. Maintaining the strength of the moment unscrewing anaerobic compositions containing dimethacrylate esters dimenisonal fatty acids, oily surfaces compared to fat is 66-89%, which is 1.3-1.8 times higher than the "Anathema-8K".

Dimethacrylate esters dimenisonal fatty acid formula

where R is CH2CH2OCH2CH2; CH2CH2Och2CH2Och2CH2; (CH2)4;
CH2CH2;



 

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SUBSTANCE: invention relates to chemical and pharmaceutical industry and specifically to an agent which is ethyl ether (±)-11,15-dideoxy-16-methyl-16-hydroxyprostaglandin E1 of formula (I), which exhibits uterotonic activity. This compound relates to the family of 11-deoxyprostaglandines and has a chemical structure similar to misoprostol.

EFFECT: agent, which is more chemically stable and is twice less toxic, surpasses misoprostol on uterotonic activity which, along with synthetic availability and absence of side effects, makes it exceptionally promising in practical use for replacing misoprostol in gynaecological binary preparations.

2 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing alkoxy-polyoxyalkylene(meth)acrylates. Described is a method of producing alkoxy-polyoxyalkylene(meth)acrylate, in which: a) at least one metal compound of formula MetOR10 is taken, where Met denotes lithium, sodium, potassium, rubidium or caesium, and where R10 denotes hydrogen or a straight or branched alkyl residue, b) at least one alcohol R12OH is added, where R12 denotes a straight alkyl residue, with 1-18 carbon atoms or 2-(2-(2-methoxyethoxy)ethoxy)ethyl, where the molar mass of R12 is less than that of alkoxy-polyoxyalkylenes, c) at least one alkylene oxide of formula (VI) is added and reacts with the metal compound of formula MetOR10, where residues R11 denote, in each case independently from each other, hydrogen or a straight alkyl residue, and d) (meth)acrylic acid anhydride is directly added and reacts with the product from step c) in the presence of a stabiliser or a mixture of stabilisers.

EFFECT: simple and improved method of producing alkoxy-polyoxyalkylene(meth)acrylates.

9 cl, 16 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing (meth)acrylic esters (F) based on alcohols having at least one carbon-carbon triple bond, characterised by that at least one alcohol having at least one carbon-carbon triple bond of formula (1) where R1 denotes hydrogen, alkyl having 1-18 carbon atoms; alkyl having 2-18 carbon atoms, aryl having 6-12 carbon atoms, cycloalkyl having 5-12 carbon atoms, interrupted, if necessary, by one or more oxygen and/or sulphur atoms and/or one or more substituted or unsubstituted amino groups, or a 5-6-member heterocycl having oxygen, nitrogen and/or sulphur atoms, wherein said residues can be substituted with aryl, alkyl, aryloxy, alkyloxy, heteroatoms/or heterocycles, respectively, and R2 denotes alkylene having 1-20 carbon atoms, cycloalkylene having 5-12 carbon atoms, arylene having 6-12 carbon atoms, or alkylene having 2-20 carbon atoms interrupted by one or more oxygen and/or sulphur atoms and/or one or more substituted or unsubstituted amino groups and/or one or more cycloalkyl groups, -(CO)-, -O(CO)O, -(NH)(CO)O-, -O(CO)(NH)-, -O(CO)- or -(CO)O, where the names of the residues can be replaced with aryl, alkyl, aryloxy, alkyloxy, heteroatoms and/or heterocycles respectively, n is a whole number from 0 to 3, preferably from 0 to 2 and more preferably from 1 to 2 and X; for each i=0 to n can be independently selected from a group comprising -CH2-CH2-O-, -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CHVin-O-, -CHVin-CH2-O-, -CH2-CHPh-O- and -CHPh-CH2-O-, preferably from a group comprising -CH2-CH2-O-, -CH2-CH(CH3)-O- and -CH(CH3)-CH2-O-, and more preferably CH2-CH2-O-, where Ph denotes phenyl and Vin denotes vinyl, wherein the hydroxy groups of the alcohol are primary or secondary, esterified in the presence of at least one enzyme (E) with (meth)acrylic acid or re-esterified with at least one (meth)acrylic ester (D).

EFFECT: use of the present method enables to obtain esters of an acid based on alcohols which have carbon-carbon triple bonds with good output and low colour indices.

5 cl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing 11(E)-tetradecen-1-ylacetate, which is sex pheromone of sod webworms, the basic component of pheromones of omnivorous leaf-roller moths, stem moths, fir leaf-roller moths and certain other types of dangerous pests, involving a Grignard reaction of acrolein with ethylmagnesium bromide to obtain 1-penten-3-ol, ortho-ether Claisen rearrangement with participation of 1-penten-3-ol and triethyl ortho-acetate to obtain ethyl ether of 4(E)-heptenoic acid, reduction of the ethyl ether of 4(E)-heptenoic acid to obtain 4(E)-hepten-1-ol, substitution of the hydroxyl group of 4(E)-hepten-1-ol with Br to obtain 1-bromo-4(E)-heptene, cross-coupling reaction of 1-bromo-4(E)-heptene with 7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide in the presence of a catalyst to obtain 11(E)-tetradecen-1-ol, acetylation of 11(E)-tetradecen-1-ol to obtain 11(E)-tetradecen-1-ylacetate, in which cross-coupling of 1-bromo-4(E)-heptene with 7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide to obtain 11(E)-tetradecen-1-ol is carried out in the presence of a Li2CuCl4 in the medium of tetrahydrofuran in the following molar ratio [1-bromo-4(E)-heptene]: [7-[(tetrahydro-2H-pyran-2-yl)oxy]heptylmagnesium bromide]:[ Li2CuCl4]:[tetrahydrofuran]=1:1.2:0.03:20 for 1 hour at temperature of minus 75°C, then for 1 hour at temperature ranging from minus 75°C to 20°C and for 10 hours at 20°C. Since the 1-2% content of the (Z)-isomer already inhibits attractive properties of 11(E)-tetradecen-1-ylacetate, existing methods are not suitable for practical application.

EFFECT: method is distinguished by stereoselectivity.

2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I), where each R1, R2 and R3 is independently selected from a group comprising H, OH, F, Cl, Br, a methoxy group and an ethoxy group; or R1 and R2 together form -OCH2O-, and R3 is selected from a group comprising H, OH, methoxy group, ethoxy group and halogens; R4 denotes OH or o-acetoxybenzoyloxy nicotinoyloxy or iso-nicotinoyloxy; R5 denotes or , and at least one of R1, R2 and R3 is not hydrogen.

EFFECT: method for synthesis of a compound of formula (I) and use of the compound of formula (I) in preparing medicinal agents for preventing or treating cerebrovascular diseases.

17 cl, 14 tbl, 5 dwg, 12 ex

FIELD: chemistry.

SUBSTANCE: method involves reaction of a polyatomic alcohol - neopentyl glycol, trimethylol propane, pentaerythritol with trialkylacetic acid in molar ratio 1:1 in the presence of an acid catalyst which is a sulphonic acid derivative having pKa between -2 and +2, carried out at temperature 180°C or lower.

EFFECT: invention enables to obtain hydrolysis-resistant esters.

8 cl, 3 tbl, 15 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing dialkyl ether of naphthalene dicarboxylic acid used in production of different polymer materials such as polyesters or polyamides from a liquid-phase reaction mixture containing low-molecular alcohol, naphthalene dicarboxylic acid, and material which contains polyethylene naphthalate, in mass ratio of alcohol to acid between 1:1 and 10:1, at temperature between 260°C and 370°C and pressure between 5 and 250 absolute atmospheres.

EFFECT: method enables production of highly pure NDC.

6 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: method of regioselective obtainment of 1-R1-2-R2-3-acetyl-glycerol derivative of the Formula 1 involves the following stages: Obtainment of 1-R1-3-(protective group)-glycerol of Formula 3 by adding protective group to 3rd position in 1-R1-glycerol of Formula 2; obtainment of 1-R1-2-R2-3-(protective group)-glycerol of Formula 4 by adding R2 group to 2nd position of 1-R1-3-(protective group)-glycerol of Formula 3, where R2 group is added by reaction of R2-OH with 1-R1-3-(protective group)-glycerol in the presence of aprotic organic solvent, catalyst and dehydrating medium; aprotic organic solvent is selected out of group consisting of hexane, heptane, dichloromethane, ethyl acetate, tetrahydrofuran and mixes thereof; dimethylaminopyridine is catalyst; and dicyclohexylcarbodiimide is dehydration medium; simultaneous removal of protective group and acetylation of 1-R1-2-R2-3-(protective group)-glycerol of Formula 4, where protective group removal reaction and acetylation reaction are performed using Lewis acid and acetic anhydride or using acetylation agent; Lewis acid is selected out of group including zink chloride (ZnC2), tin chloride (SnCl2), boron trifluoride diethyl ether (BF3Et2O) and mixes thereof; acetylation agent is selected out of group including acetylchloride, acetylbromide and mixes thereof, where compounds of Formulae 1-4 are racemic or optically active; R1 is palmitic acid group, R2 is linoleic acid group; P is trityl or trialkylsilyl as protective group; alkyl in trialkylsilyl is an alkylic group containing 1-5 carbon atoms, so that if the protective group is trityl then 1-R1-3-(protective group)-glycerol is obtained in the presence of pyridine solvent at 40-60°C or in the presence of nonpolar aprotic organic solvent and organic base within 0°C to room temperature range; nonpolar aprotic organic solvent is selected out of group including pyridine, dichloromethane, tetrahydrofuran, ethyl acetate and mixes thereof; organic base is selected out of group including triethylamine, tributylamine, 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) and mixes thereof, and if the protective group is trialkylsilyl then 1-R1-3-(protective group)-glycerol is obtained in the presence of aprotic organic solvent and organic base within 0°C to room temperature range; aprotic organic solvent is selected out of group including dichloromethane, tetrahydrofuran, ethyl acetate, dimethylformamide and mixes thereof; and organic base is selected out of group including imidazole, triethylamine, and mixes thereof. [Formula 1] , [Formula 2] , [Formula 3] , [Formula 4] .

EFFECT: obtainment of glycerol derivative with high efficiency and output.

8 cl, 10 ex

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

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing butylacrylate involving: reaction of acrylic acid with butanol in the presence of water and a catalyst in a reactor; where the starting material is an aqueous solution of acrylic acid which is at least one of: (1) condensed water, obtained from vapour used in a kinetic vacuum pump which transports gas after trapping fluid process medium- vapour which is blown at high speed, (2) water for hydraulic sealing in a liquid ring pump which isolates liquid-water after air is let into the housing, (3) water used for collecting acrylic acid in the device which collects acrylic acid from an acrylic acid-containing gas, and acrylic acid which is not present in the aqueous solution of acrylic acid, where the device used for collecting acrylic acid is one or more devices selected from a group comprising a packed column, a plate-type column, a spray column and a scrubber. The invention also relates to a method of producing a super-absorbing polymer based on acrylic acid, involving the following steps: polymerisation of acrylic acid, in which the aqueous phase used is an emulsified aqueous solution of an acrylic acid monomer and water, dehydration of the obtained mixture during azerotropic distillation, where the starting material is aqueous acrylic acid solution which is at least one of the following: condensed water obtained from vapour used in a kinetic vacuum pump which transports gas after trapping fluid process medium - vapour, which is blown at high speed, water for hydraulic sealing in a liquid ring pump which isolates liquid-water after air is let into the housing, water used for collecting acrylic acid in the device which collects acrylic acid from an acrylic acid-containing gas, and acrylic acid which is not present in the aqueous solution of acrylic acid, where the device used for collecting acrylic acid is one or more devices selected from a group comprising a packed column, a plate-type column, a spray column and a scrubber.

EFFECT: design of an efficient method of using aqueous solution of (meth)acrylic acid with low concentration, formed at the stage for producing/storing (meth)acrylic acid.

13 cl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to organic synthesis, specifically to a method of producing methyl formate, which is used as an intermediate product during synthesis of organic acids such as formic acid, acetic acid, propionic acid and esters thereof, as well as an additive to diesel fuel. The method of producing methyl formate from a gas which contains a mixture of carbon oxide and hydrogen involves treating the mixture of hydrogen and carbon oxide with alkali with formation of an alkali metal formate and purified hydrogen. The obtained alkali metal formate is then dissolved in water and treated with sulphuric acid with formation of formic acid, while separating sulphur impurities, and the formic acid is reduced to methanol with hydrogen using a hydrogenation catalyst. The formic acid is reduced until conversion of 50-90 mol %. The cooled mixture of methanol and formic acid is rectified in the presence of an acid catalyst, while esterifying the reaction to methyl formate.

EFFECT: increased output of high-quality end product while using material with various degree of purity.

7 cl, 2 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing dimethyl-1,5-naphthalene dicarboxylate that is used in preparing polymers based on thereof and articles made of these polymers. The economic and effective method involves the following stages: (1) dehydrogenation of 1,5-dimethyltetraline to yield 1,5-dimethylnaphthalene; (2) oxidation of 1,5-dimethylnaphthalene prepared at dehydrogenation stage to yield 1,5-naphthalene dicarboxylic acid being without accompanying isomerization stage, and (3) esterification of 1,5-naphthalene dicarboxylic acid prepared at oxidation stage in the presence of methanol to yield the final dimethyl-1,5-naphthalene dicarboxylate.

EFFECT: improved preparing method.

9 cl, 3 dwg, 5 ex

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