Method of obtaining esters of amyl alcohols

FIELD: chemistry.

SUBSTANCE: invention relates to methods of obtaining esters of amyl alcohols and simplest carboxylic acids C1-C4. Alcohol-containing wastes of caprolactam production are used as raw material. Method includes etherification of alcohol-containing wastes of caprolactam wastes with simplest carboxylic acids C1-C4 in presence of acidic catalyst. Process of etherification is carried out with continuous azeotropic distillation of water with reaction mixture components, as catalyst, sulfuric or orthophosphoric acid is used, catalyst is loaded in amount 0.1-2.5% of the total weight of initial substances, reaction mixture is cooled to 20-30°C and neutralised with water-alkaline solution with mixing to water layer pH 7-8, water phase is separated, organic phase is washed one-two times with water, final purification of esters is carried out by fractional distillation of organic phase. Obtained products are suitable for application as solvents for paints and varnishes, raw material for organic synthesis, as component of complex fuel additives.

EFFECT: obtaining esters of amyl alcohols and simplest carboxylic acids C1-C4, characterised by high purity without catalyst admixtures, low water content - not more than 0,1%, and residual organic acids - not more than 0,01 without application of secondary rectification, as absence of acid facilitates purification of esters.

9 ex

 

The invention is directed to the development of a method of producing esters amyl alcohols and simple carboxylic acids (C1-C4using as raw material alcohol-containing waste caprolactam production, namely by-products of the production of cyclohexanone and caprolactam containing amyl alcohols in the amount of 30-80%, for example, sold under the trade name "Flotation SFC (amyl alcohol) (TU 6-03-465-79) or SFPR (TU 113-03-10-5-85). The resulting esters can be used as components of composite or individual solvents in the paint industry as a solvent in the manufacture of explosives, as a component of comprehensive fuel additives as raw materials for organic synthesis, deep cleaning as fragrances in perfumes and household chemicals.

A method of obtaining esters of dicarboxylic acids With2-C6and alcohols (Patent RU 2373188, publ. 20.11.2009, SS 69/02, SS 67/03), according to which the process is carried out by esterification of a mixture of mono - and dicarboxylic acids With2-C6(containing adipic acid 53-60%) obtained by the process of evaporation of water is acidic effluent from the production of caprolactam, acid catalysts, in the presence of a third component (benzene) at a temperature of 80-90°C until the complete termination of allocation of water to last the subsequent neutralization of the catalyst and unreacted acid, the washing water from the formed salts, separating the organic layer from the water allocation esters by distillation, consisting of distillate benzene fraction, distillate fractions of alcohols, vacuum distillation fractions of volatile esters with the production of esters as VAT residue, characterized in that as tarifitsiruemih agent is used cyclohexyloxy alcohol (purity of at least 99.8%) or alcohol fraction containing 70-75% of a mixture of amyl, isoamyl and cyclohexylamin alcohols, which is also a waste of caprolactam production.

The disadvantage of this method is the use of the third toxic component (benzene), which leads to additional complexity of the technological scheme.

A method of obtaining esters of carboxylic acids (Patent RU 283299, publ. 2003.06.27, SS 87/08, SS 69/80). The proposed method lies in the interaction of di - or polycarboxylic acids or their anhydrides with alcohols, and the reaction water is removed by azeotropic distillation, the liquid is removed from the reaction by azeotropic distillation, fully again replaced by alcohol. This method shows good results in the output esters, and also leads to a reduction of the time of esterification due to the replacement fluid removed by distillation, pure alcohol.

The disadvantages of the top the way are used as raw materials of pure alcohols and acid anhydride, which significantly increases the cost of ester obtained, and the process at sufficiently high temperatures 160-240°C due to the use of titanium catalysts.

A method of obtaining esters and/or mixtures thereof (Patent RU 2127722, publ. 20.03.1999, SS 67/08, SS 69/14). The present invention provides a method of synthesis of esters of alcohols by esterification with organic acids at a temperature of 60-130°C, in the presence of a catalyst is a cation exchange resin type KU-2, pre-treated with sulfuric acid based 5-20 wt. %. Before the separation of the two phases is cooling down the reaction mixture to a temperature of (-2)-(-5)°C. the feedstock is waste product of vinyl acetate and alcohols.

The disadvantages of this method are the use of expensive catalyst is a cation exchange resin type KU-2, and the presence of stage tahaliyani the reaction mixture to a temperature of (-2)-(-5)°C, which causes an appreciation of the process and the complexity of the technological scheme, through the use of a refrigeration system.

The closest in technical essence is a method of obtaining esters from waste caprolactam production (Patent RU 2422434, publ. 27.06.2011, SS 69/02, SS 67/03, SS 69/06, SS 69/14. The prototype.), according to which the process is carried out by reaction etherip the requirements of organic acid and alcohol in terms of autocatalytic heat, supporting the esterification reaction at a temperature of 40-130°C using as a catalyst cation exchange resin pretreated with sulfuric acid in an amount of 0.4-2% wt. from the mass of the loaded raw cooling down, the reaction mixture before separation of the two phases.

The disadvantages of this method are the use of expensive cation exchange resin, the complexity of its preparation, incomplete conversion and the need for regeneration of raw materials, low purity esters due to the lack of cleansing stage.

The present invention is to develop a method of obtaining cheap amyl esters of alcohols of high purity of the alcohol waste caprolactam production with the aim of expanding the existing resource base for the production of esters of high purity, with the aim of expanding the existing resource base for the production of esters, highly efficient utilization of alcohol waste, increase resource efficiency in the production of caprolactam, get cheap amyl ethers of alcohols.

This object is achieved in that in a method of producing esters amyl alcohols, comprising the etherification alcohol-containing waste caprolactam production simplest carboxylic acids C1-C4in the presence of an acid catalyst, about the ECC esterification is carried out with continuous azeotropic distillation of the water with the components of the reaction mixture, as catalyst, use sulfuric or phosphoric acid, the catalyst was loaded in an amount of 0.1-2.5% of the total mass of the original substances, the reaction mixture is cooled to 20-30°C. and neutralized aqueous-alkaline solution under stirring until the pH of the aqueous layer 7-8, the aqueous phase is washed twice with water, final cleaning esters carried out by fractional distillation of the organic phase.

The amount of organic acid added to the reaction, is determined based on the water content and hydroxyl groups used in alcohol production waste caprolactam. Applies a ratio of 0.95 to 1.2 mol of the organic acid to 1 mol of hydroxyl group of alcohol-containing raw materials (in terms of anhydrous raw materials). The use of a larger excess acid is impractical because it leads to wasteful consumption of the latter, the use of insufficient acid (less than these of 0.95 mol per 1 mol Oh-groups) is also impractical because it is not conducive to full conversion of the alcohols, which, in turn, complicates the process of separation and purification of esters.

The etherification is carried out in the presence of a catalyst, which is non-volatile mineral acid (sulfuric or phosphoric). The catalyst was loaded in an amount of 0.1-2.5% of the total mass of the original substances.

Azeotropic mixture which after condensation are separated and the organic phase is recycled back into the reaction. The process continues until the complete termination of allocation of water from condensation of the vapors. Then the reaction mixture was neutralized with an aqueous solution of caustic soda (sodium hydroxide, potassium hydroxide or other alkali mixtures thereof or deletestream solutions). The neutralization is carried out with stirring until the pH of the aqueous layer 7-8. Neutralization is required to free the reaction mixture from the catalyst residues and organic acids. The absence of organic acid in the reaction products facilitates further purification of esters.

The aqueous phase is separated, the organic phase is washed twice with water and subjected to further distillation or rectification, depending on the required quality of esters.

Separation processes are carried out under atmospheric pressure and under vacuum, as in intermittent and continuous mode. When the distillation or rectification selected fraction, wikipaedia within the boiling points obtained amyl ethers.

The process of rectification spending, both at atmospheric pressure and under vacuum 5-100 kPa (abs.). Conducting distillation under vacuum allows to reduce the temperature of the process. The pressure range selected on the basis of technological feasibility, creating a vacuum below 5 kPa (abs.) requires the use of expensive vacuum techniques is.

For carrying out the esterification alcohol-containing waste production of caprolactam via the described method is used azeotropically agent, forming a low-boiling azeotropic mixture with water, choose from the list of individual hydrocarbons or their fractions (hexane, heptane, gasoline nefras, and so on), aromatic hydrocarbons or their fractions (toluene, xylene, solvent oil, and so on), halogenated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, dichloroethane, 1,1,2,2-tetrachlorethane and so on). Use osetroobraznykh agents allows to lower the boiling temperature of the reaction mixture and, consequently, the temperature of the reaction. Azeotropically agent is added in amounts of 5-20% of the total mass of the starting materials. After completion of the reaction at the stage of rectification azeotropically agent selected in a separate faction with an appropriate boiling point and re-use.

To reduce the boiling temperature of the reaction mixture of the process of esterification is carried out at reduced pressure (20-100 kPa).

The combination of new features allows you to get esters amyl alcohols and simple carboxylic acids (C1-C4containing up to 96-98% esters, not more than 0.01% of free acid and not more than 0.1% water. In turn, received PR is dehaemer way amyl esters of alcohols can be used as solvents for paints and varnishes as raw material for organic synthesis, and as part of a comprehensive fuel additives.

Example 1

In a heated reactor capacitive type, equipped with a stirrer, reflux condenser and separator, download 5,50 kg alcohol fraction of caprolactam (containing 10% water, a hydroxyl number 365 mg KOH/g), 2.21 kg (36,7 mol) of acetic acid, 0,018 kg of concentrated sulfuric acid. Stage esterification is carried out at boiling and continuous distillation of water, which is removed in the composition of the azeotropic mixture with the other components of the reaction system. Azeotropic mixture after condensation in the refrigerator flows into the separator where it is divided into two phases. The upper organic phase by gravity back into the reaction, the lower the water remains in the separator.

The process continues until the complete termination of allocation of water from condensation of the vapors. Then the reactor is cooled to 20-30°C and neutralized by stirring with 5% aqueous sodium carbonate solution until the pH of the aqueous layer 7-8. The aqueous phase is drained, the organic phase is twice washed with water until neutral wash water. The organic phase is subjected to fractionation at atmospheric pressure in a distillation installation periodic action with irregular nozzle, reflux 1. Select the fraction boiling in the temperature range of 145-150°C. Receive 3,52 kg esters, which is s contain acetates amyl alcohol 96%, including n-amylacetate 89%; water is 0.04%, the residual acetic acid 0,004%.

Example 2

The etherification is conducted analogously to example 1. Use azeotropically agent - toluene in the amount of 0.8 kg per stage rectification additionally selected fraction of toluene (so Kip. 110-120°C). Get 0,74 kg toluene fraction and 3.57 kg esters, which contain acetates amyl alcohol 96%, including n-amylacetate 90%; water of 0.03%, the residual acetic acid 0,006%.

Example 3

The etherification is conducted analogously to example 1. Stage esterification is carried out under vacuum 65-70 kPa (abs.). Get 3,45 kg esters, which contain acetates amyl alcohol 95%, including n-amylacetate 87%; water is 0.04%, the residual acetic acid is 0.005%.

Example 4

The etherification is conducted analogously to example 1. Esters produce a simple distillation under atmospheric pressure. Collect the fraction, wikipaedia in the temperature range 143-152°C. Receive 3.15 kg of esters, which contain: amylacetate 78%, including n-amylacetate 70%; water 0,09%, residual acetic acid 0,003%.

Example 5

The etherification is conducted analogously to example 1. Esters emit continuous distillation under atmospheric pressure; nozzle irregular, reflux 1. Collect the fraction, wikipaedia in the temperature range of 145-150°C. Receive 4,15 kg esters, which contain acetates is Milovich alcohols 98%, including n-amylacetate 92%; water of 0.02%, the residual acetic acid 0,003%.

Example 6

The etherification is conducted analogously to example 1. As catalyst, use phosphoric acid in amount of 0.15 kg Get 3,51 kg esters, which contain acetates amyl alcohol 96%, including n-amylacetate 89%; water is 0.04%, the residual acetic acid is 0.005%.

Example 7

The etherification is conducted analogously to example 1. Esters are distilled under vacuum to 4.5 kPa (abs.). Collect the fraction, wikipaedia in the temperature range 60-67°C. Receive 3,19 kg esters, which contain acetates amyl alcohols 80%, including n-amylacetate 71%, water 0,07%, residual acetic acid 0,003%.

Example 8

In a heated reactor capacitive type, equipped with a stirrer, reflux condenser and separator, a load of 5.0 kg alcohol fraction of caprolactam (containing 10% water, a hydroxyl number 365 mg KOH/g), 1,50 kg (32,6 mol) of formic acid, 0,018 kg of concentrated sulfuric acid. Stage of esterification and the neutralization is conducted as in example 1. The organic phase is subjected to fractionation at atmospheric pressure in a distillation installation periodic action with irregular nozzle, reflux number of 1.5. Select the fraction boiling in the temperature range 128-135°C, receive 3,02 kg esters, which contain the formate of emilov the x alcohols 92%, including n-ameliorate 82%; water of 0.08%, the residual formic acid 0,007%.

Example 9

In a heated reactor capacitive type, equipped with a stirrer, reflux condenser and separator, a load of 5.0 kg alcohol fraction of caprolactam (containing 10% water, a hydroxyl number 365 mg KOH/g), 2,58 kg (29,3 mol) butyric acid, 0,028 kg of concentrated sulfuric acid. Stage of esterification and the neutralization is conducted as in example 1. The organic phase is subjected to fractionation at a pressure of 5 kPa in a distillation installation periodic action with irregular nozzle, reflux 1. Select the fraction boiling in the temperature range of 85-95°C, receive 3,11 kg esters, which contain butyrate amyl alcohols 86%, including n-livetrace 81%, water of 0.01%, the residual butyric acid 0,008%.

Thus, the proposed method makes it possible to obtain esters of amyl alcohols and simple carboxylic acids (C1-C4high purity, low water content and residual organic acids; suitable for use as solvents for paints, raw materials for organic synthesis, part of a comprehensive fuel additives.

The method of obtaining esters amyl alcohols, comprising the etherification alcohol-containing waste production is as caprolactam simplest carboxylic acids C 1-C4in the presence of an acid catalyst, characterized in that the process of esterification is carried out with continuous azeotropic distillation of the water with the components of the reaction mixture as a catalyst uses sulfuric or phosphoric acid, the catalyst was loaded in an amount of 0.1-2.5% of the total mass of the original substances, the reaction mixture is cooled to 20-30°C and neutralized aqueous-alkaline solution under stirring until the pH of the aqueous layer 7-8, the aqueous phase is separated, the organic phase is washed twice with water, final cleaning esters carried out by fractional distillation of the organic phase.



 

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5 cl, 4 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of general formula (I)

, in which X denotes a CHO, CH2OH or CH2OC(O)R group, where R denotes a straight of branched C1-C5 alkyl chain; as well as to a synthesis method, particularly synthesis of 6,8-dimethylnon-7-enal (1) through hydroformylation of 5,7-dimethylocta-1,6-diene. The invention also relates to fragrant compositions containing formula (I) compounds. Owing to their fragrant properties, these compounds are of great interest in perfumery, particularly cosmetic products and household chemicals.

EFFECT: obtaining novel fragrant compositions.

12 cl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing lower alkyl ether of lower aliphatic alcohol having formula R1-COO-R2, involving reaction of a pre-dried lower alkyl ether having formula R1-O-R2, in which R1 and R2 independently denote C1-C6alkyl groups, provided that the total number of carbon atoms in groups R1 and R2 ranges from 2 to 12, or R1 and R2 together form a C2-C6 alkenyl group, with material which contains carbon monoxide, in the presence of a catalyst which contains mordenite and/or ferrierites in anhydrous conditions. The invention also relates to a method of producing carboxylic acids through hydrolysis of esters obtained using the method given above.

EFFECT: high output and selectivity of end product.

29 cl, 3 tbl, 9 dwg

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to application of compounds with formula R2=R1-X, where R1 and R2 have 23 to 35 carbon atoms in sum, X represents primary alcohol functional group -CH2OH or carboxyl group -COOH, R1 is saturated linear hydrocarbon chain with 9 carbon atoms, and R2 is linear hydrocarbon chain, which is saturated or unsaturated, including 1 to 4 unsaturated double links.

EFFECT: producing formulations suited for application to hypercholesterolemia therapy and prophylaxis.

3 cl, 4 tbl, 6 ex

FIELD: organic chemistry, cosmetics.

SUBSTANCE: invention relates to novel compounds of the formula (I) , wherein a dotted line means a bond or it absent and wherein R1 means: -when a dotted line as a bond is absent: -CHCH3OH or -CHCH3OCOR or -CHCH3XCH2CHOHR' or -CHCH3OCHR'CH2OH or ; -when a dotted line is absent: , -CHCH3OH, -CHCH3OCOR, -COCH3, -CHCH3XCH2CHOHR', -CH2CH2XCH2CHOHR', -CHCH3OCHR'CH2OH, -CHCHCOR', -CHCH2CHR'OH, -CH2CHCHR'OCOR, -CHCHCHOHR' or -CHCHCHR'OCOR wherein R means H, Me, Et, Pr, isoPr, But, isoBut, -CH3(CH2)4, -(CH3)2CHCH2, -CH2=CH or -(CH3)2C=CH; R' means H, Me or Et; X means O, N or S atoms. Owing to their odor proposed compounds can be used in perfume industry, cosmetics and care substances and can be used as aromatizing components for preparing atomatized composition or aromatized article.

EFFECT: valuable properties of compounds.

11 cl, 14 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention, in particular, relates to production of fatty acid alkyl esters via catalytic reesterification of triglycerides/fatty acids mixture. During this reaction, ester phase containing fatty acid alkyl esters and glycerol phase containing fatty acids are formed in reaction mixture. Phases are separated from each other. Fatty acids are isolated from glycerol phase in the form of fatty acid phase. The latter is further combined with triglycerides/fatty acids mixture and fatty acids contained in resulting mixture in amount about 10% are esterified with alcohol to produce esterification mixture containing triglycerides and fatty acid alkyl esters. This mixture is then subjected to reesterification with alcohol to produce additional amount of fatty acid alkyl esters. Esterification is effected in presence of acid catalysts and reesterification in presence of alkali catalysts.

EFFECT: improved economic characteristics of process due to recovery of additional amount of desired product.

7 cl

FIELD: chemistry.

SUBSTANCE: invention relates to improved method of obtaining at least one of acetic acid and methylacetate by carbonylation of capable of carbonylation agent, selected from the group including methanol, methylacetate and dimethyl ether, with carbon monoxide in presence of catalyst, with catalyst being represented by desiliconised mordenite.

EFFECT: method is characterised by improvement of catalytic activity.

15 cl, 3 tbl, 3 ex

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