The method of obtaining second-butyl acetate

 

(57) Abstract:

The invention relates to chemical technology, in particular to a method for producing sec-butyl acetate (BWA), used as a solvent for paints and varnishes and for the production of sec-butyl alcohol. The method consists in alkilirovaniya acetic acid (CA) n-butenes using butane-butenova fraction in the liquid phase. As catalyst, use fixed layer selfactivity resin in the H+- form. The resulting reaction mass is then cooled to a temperature which is lower than the outlet temperature of the catalyst layer. Part of the cooled reaction product is recycled to the catalyst bed, and synthesis are several reactors. In the presence of a cascade of three reactors keep the temperature at the inlet to the first reactor 90-110oWith the second reactor is 70-100oWith the third reactor 70-75oWith or in the presence of a cascade of two reactors keep the temperature at the inlet to the first reactor 90-110oSince, in the second reactor 70-75oWith and carry out recycle part of the cooled reaction mixture in each reactor. The weight ratio of the amount of recycle stream to the quantity of raw materials is equal to or more mn of the earth with the total amount; n is the number of the reactor; And the molar ratio of acetic acid and n-butenes in the feed fresh raw material in the first reactor; the molar ratio of butane and n-butenes in the feed butane-butenova faction. The technical result is an increase in the yield of the final product. 1 C.p. f-crystals, 1 Il., table 1.

The invention relates to chemical technology, more specifically to a method for producing sec-butyl acetate (BWA). The BWA is used as a solvent for paints and varnishes and as raw material for the production of sec-butyl alcohol. Sec-butyl alcohol can be used as a high-octane component of gasoline and as raw materials for the production of methyl ethyl ketone, a solvent for dewaxing of lubricating oils.

A method of obtaining the BWA alkylation acetic acid (CA) n-butenes at elevated temperatures 70-110oC and a pressure of 9 to 10 ATA in the presence of a catalyst (cation exchange resin) in an amount of 10-40 wt.% with respect to the reaction mass at a molar ratio of n-butenes:MC= (1-3): 1.

The reaction is carried out at a stirring in an autoclave for 1 to 4 hours. Conversion of n-butenes in the process low, slightly above the 30 - 33%.

After completion of the reaction in the autoclave is required catalyst separation fil is x n-butenes (Ed. mon. USSR N 560875, class C 07 C 69/14).

A method of obtaining the BWA liquid-phase esterification of n-butenes of the criminal code in the presence of cation-exchange resins in the acid form, followed by the separation of the air from the acid by azeotropic distillation. The molar ratio of n-butenes and MC withstand 10:1-1:10.

In particular, the process is carried out under stirring in an autoclave at a temperature of 90oC for 10 h using n-butenova fraction with a concentration of 72.6 wt. %. Then the reaction mixture is cooled, the resin is separated by decantation. The output of the BWA is 60%.

The disadvantage of this method is the low output of BWA and problems of a technological nature, consisting in the destruction of the catalyst with stirring and the need for its separation from the reaction mass at the end of each experience (U.S. Pat. France N 2447896, class C 07 C 31/12).

The known method of synthesis of BWA by alkylation of the criminal code of n-butenes in the sulfonic cation exchanger KU-23. Anhydrous criminal code together with butane-butenova fraction served in a tubular reactor, the reaction heat is removed by the refrigerant flowing in the annular space of the reactor. After the reactor of the first reaction mixture is separated by distillation of unreacted hydrocarbons. CBM product of the column separation is Oh. From the bottom of the column anhydrous acid recycle to the reactor.

The disadvantage of this method is the low conversion of n-butenes, which is associated with an excess of n-butenes in the alkylation process, because the ratio of n-butenes: MC = 2:1, and the possibility of catalyst poisoning of the criminal code, recycled from a cube column allocation of BWA in the alkylation reactor. The criminal code contains according to GOST 19814-74, grade 1, heavy metals to 0.0005 wt.%, non-volatile residue to 0.0005 wt. %. These impurities, as well as polymers of n-butenes formed during the alkylation, will concentrate in the bottom liquid and poison the catalyst. n-Butenova fraction may contain higher olefins, C5and above, forming with the criminal code of the high-boiling esters, which will accumulate in the criminal code. Unsaturated hydrocarbons (butenes, pentane) can also dry out. Recycling of polymers will reduce the activity of the catalyst (M. P. Stepanov, V. M. Obukhov, A. C. Bondarenko, M. I. Farberov. ZH, N 3, 1977, pp. 640 - 644).

The closest in technical essence of the present invention is a method for the BWA described in U.S. patent 5457228, CL 560-241, according to which a mixture of MC and n-butenes is injected in parallel through the reactor, loaded by a continuous layer of kationoobmennuyu from 1.0 to 2.0, the volumetric rate of the criminal code regarding the catalyst is 0.1 - 10 h-1the temperature at the inlet to the catalyst bed is 80-120oC. the resulting reaction mixture is cooled to a lower temperature, but not below 80oC, and carry out recycling of the reaction mixture after cooling in the beginning of the process; the weight ratio of the amount of recycle stream to the quantity of raw material shall be determined in accordance with equation

< / BR>
where X is the weight ratio of the amount of recycle stream to the amount of raw materials;

A is the molar ratio of the criminal code and n-butenes in the feed to the reactor with fresh raw materials.

The disadvantage of the process is the low conversion of n-butenes in the BWA 68,6 - to 82.9% in low selectivity to 89.5 - 96,6%. In the process used concentrated n-butenes, which significantly increases the price received by BWA. In addition, it is known that the introduction of n-butane, which is an inert solvent, increases the selectivity of the reaction of formation of the BWA, reducing the yield of dimers of n-butene (C. M. Obukhov, I. P. Stepanova, A. C. Bondarenko, M. I. Farberov. Petrochemicals, T. XVII, No. 2, pp. 262 - 267).

On the other hand, the control process proposed in patent formula is impossible when using butane-butenova fra the Oia is to increase the yield of the target product The BWA.

This goal is achieved by a method of obtaining the BWA by alkylation of the criminal code of n-butenes using BBF. The method includes a step of entering the criminal code and n-butenes in the liquid phase in parallel through a fixed bed cation exchange resin stirolsulfokisloty type, in particular selfactivity resin in the H+form, followed by cooling the reaction mass to a temperature which is lower than the outlet temperature of the catalyst layer, and recycling part of the cooled reaction product in the catalyst layer, and is characterized by the fact that the synthesis are several reactors and in the presence of a cascade of three reactors keep the temperature at the inlet to the first reactor 90 - 110oC, in the second reactor 70 - 100oC, in the third reactor - 70 - 75oC or in the presence of a cascade of two reactors keep the temperature at the inlet to the first reactor 90 - 110oC, in the second reactor 70 - 75oC and perform recycle part of the cooled reaction mixture in each reactor, and the weight ratio of the amount of recycle stream to the quantity of raw materials is equal to or more than the value of X defined by the equation

< / BR>
where X is the weight ratio of the amount of recycle stream to the amount of si is>B - the molar ratio of butane and n-butenes in the feed butane-butenova faction.

The drawing shows a scheme for the BWA in the presence of a cascade of three reactors. The mixture of the criminal code and BBF with a concentration of n-butenes at least 30 wt.%, containing small amounts of isobutene, butadiene and propene in a molar ratio of the criminal code: n-butenes = 1.5 to 2.5:1 is directed through the heater 1 in the cascade adiabatic reactors 2A, 2B, 2C, loaded selfactivity resin in the H+-form. The inlet temperature in these reactors is supported in the following range: reactor 2A - 90-110oC, the reactor 2B - 70-100oC, the reactor 2B-70-75oC. Heat the reaction of alkylation remove chilled respectively in refrigerators 4A, 4B, 4C by reciclada served in the reactor circulation pumps 3A, 3b, 3C. The alkylation process is conducted so that the conversion of n-butenes in the reactor 2A, 2B, 2C respectively 60 - 85%, 85 - 92%, 95 - 98%. In the presence of a cascade of two reactors, the inlet temperature in the first reactor is maintained within the range of 90 - 110oC, the second 70 - 75oC. the alkylation Process is conducted so that the conversion of n-butenes were respectively 81-83% 92-95%.

Selection BA and the criminal code. In the Packed column 6 is the azeotropic separation of BWA from the criminal code.

To avoid poisoning of the cation recycled MC generated in the column azeotropic allocation of BWA, is taken from 3-4 plates exhaustive part of the column and its bottom liquid of the column devoted to Stripping for further cleaning of the criminal code of polymers.

The present invention allows to solve several problems:

- increase the conversion of n-butenes in the BWA;

to increase the selectivity of the conversion of n-butenes in the BWA;

- increase the life of the alkylation catalyst is a cation exchange resin;

- to reduce the process of getting the BWA due to the use of BBF.

Example 1. 1.8 l selfactivity resin macroporous structure in the H+form with full static exchange capacity of 1.9 mgecw/cm3download three tubular reactor 2A, 2B, 2C (drawing) with a diameter of 20 mm layer height 2 m 0.6 l each. To prevent heat loss into the environment reactors thermostatic the flow of the coolant in the jacket. Liquid raw material consisting of a mixture of BBF, fresh and circulation of the criminal code, supplied to the heater 1, the heated hot water during start-up, and then enters the first reactor 4A, and the carrying part, equal to the number of incoming raw materials in the reactor 2A is sent to the second reactor cascade 2B. The reaction mixture from the second reactor cascade 2B pump 3b through the fridge 4B partially recycled to the reactor 2B, and mingling with the raw materials supplied to the reactor 2B.

The carrying portion of the reaction mixture is equal to the number of incoming raw materials in the reactor 2B, is given after the refrigerator 4B in the third reactor of the cascade 2B. The reaction mixture leaving the third reactor of the cascade 2B, the pump 3 through the condenser 4B recycle to the reactor inlet 2B and mixed with the raw material into the reactor 2B.

The carrying amount of the reaction mixture enters the Packed column 5 performance 10 theoretical plates for separation of unreacted gases (butane, n-butenes). Department of BBF from a mixture of BWA and MC is conducted at a pressure of 6 to 9 kg/cm2and reflux 3. Stable mixture of BWA and the criminal code throttled to a pressure of 1.5 kg/cm2and enters the Packed column 6 effectiveness 25 theoretical plates. For azeotropic separation of BWA from the criminal code in raw columns 5 water is pumped or injected MC concentration 80-85 wt.%. Water is an azeotropic agent.

Top coloncleanse in razorscale (not shown) in the organic phase is The BWA and the aqueous phase. The aqueous phase is partially recycled to the column 6 as the azeotropic agent, and the carrying amount of water equal to entered into the system with the raw material of the column is withdrawn from the system.

Concentrated criminal code, containing less than 0.08 wt.% water is withdrawn from comprehensive paragraph (2 theoretical plates) and recycle at the site of synthesis, pre-mixed with fresh criminal code.

Its bottom liquid of the column containing 120oC high-boiling products (BCP), corrosion products and the criminal code, is given in the node separating the high-boiling compounds. Tarenna of the criminal code in the reactor recycle system.

The invention is illustrated by table.

1. The method of obtaining second-butyl acetate by alkylation of acetic acid n-butenes, including the state of input acetic acid and n-butenes in the liquid phase in parallel through a fixed bed cation exchange resin stirolsulfokisloty type followed by cooling the reaction mass to a temperature which is lower than the outlet temperature of the catalyst layer, and recycling part of the cooled reaction product in the catalyst layer, characterized in that the synthesis are several reactors and in the presence of CAS With, in the third 70-75oWith or in the presence of a cascade of two reactors at the entrance to the first reactor 90-110oWith the second - 70-75oWith and carry out recycling part of the cooled reaction mixture in each reactor, and the weight ratio of the amount of recycle stream to the quantity of raw materials is determined by the formula:

< / BR>
where X is the weight ratio of recycle stream to the amount of raw materials;

n is the number of the reactor;

And the molar ratio of acetic acid to n-butenes in the feed fresh raw material in the first reactor;

In the molar ratio of butane to n-butenes in the feed butane-butenova faction.

2. The method according to p. 1, characterized in that the alkylation apply recirculation acetic acid, isolated from the reaction mixture by azeotropic distillation and the output side Poonam from exhaustive of the column azeotropic distillation.

 

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55 cl, 1 dwg, 7 tbl, 22 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to the improved method for oxidation of (C2-C4)-alkane and preparing the corresponding alkene and carboxylic acid. Method involves addition of this alkane to contact with molecular oxygen-containing gas in oxidative reaction zone and optionally at least one corresponding alkene and water in the presence of at least two catalysts with different selectivity. Each catalyst is effective in oxidation of alkane to corresponding alkene and carboxylic acid resulting to formation of product comprising alkene, carboxylic acid and water wherein the molar ratio between alkene and carboxylic acid synthesized in the reaction zone is regulated or maintained at the required level by regulation the relative amounts of at least two catalyst in the oxidative reaction zone. Also, invention relates to the combined method for preparing alkyl carboxylate comprising abovementioned stage in preparing alkene and carboxylic acid in the first reaction zone. Then method involves the stage for addition of at least part of each alkene and carboxylic acid prepared in the first reaction zone to the inter-contacting in the second reaction zone the presence of at least one catalyst that is effective in preparing alkyl carboxylate to yield this alkyl carboxylate. Also, invention relates to a method for preparing alkenyl carboxylate comprising the abovementioned stage for preparing alkene and carboxylic acid in the first reaction zone and stage for inter-contacting in the second reaction zone of at least part of each alkene and carboxylic acid synthesized in the first reaction zone and molecular oxygen-containing gas in the presence of at least one catalyst that is effective in preparing alkenyl carboxylate and resulting to preparing this alkenyl carboxylate.

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30 cl, 1 dwg, 5 tbl, 14 ex

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FIELD: chemistry.

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43 cl, 1 ex

FIELD: chemistry.

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7 cl, 2 tbl, 17 ex

FIELD: chemistry.

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10 cl, 4 ex, 1 dwg, 1 tbl

FIELD: chemical industry; production of synthesis gas, methanol and acetic acid on its base.

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EFFECT: the invention ensures, that reconstruction of operating installations increases their productivity and expands assortment of produced industrial products.

44 cl, 3 ex, 6 dwg

FIELD: petrochemical processes.

SUBSTANCE: invention relates to improved C2-C4-alkane oxidation process to produce corresponding alkene and carboxylic acid, which process comprises bringing indicated alkane in oxidation reaction zone into contact with molecular oxygen-containing gas and corresponding alkene and optionally with water in presence of at least one catalyst efficient for oxidation of alkane into corresponding alkene and carboxylic acid. Resulting product contains alkene, carboxylic acid, and water, wherein alkene-to-carboxylic acid molar ratio in oxidation reaction zone is controlled or maintained at desired level by way of controlling alkene and optional water concentrations in oxidation reaction zone and also, optionally, controlling one or several from following parameters: pressure, temperature, and residence time in oxidation reaction zone. Invention also relates to integrated process of producing alkyl carboxylate including above-indicated stage of producing alkene and carboxylic acid in first reaction zone and stage of bringing, in second reaction zone, at least part of each of alkene and carboxylic acid obtained in first reaction zone in contact with each other in presence of at least one catalyst effective in production of alkyl carboxylate to produce the same. Invention further relates to production of alkenyl carboxylate including above-indicated stage of producing alkene and carboxylic acid in first reaction zone and stage of bringing, in second reaction zone, at least part of each of alkene and carboxylic acid obtained in first reaction zone plus molecular oxygen-containing gas into contact with each other in presence of at least one catalyst effective in production of alkenyl carboxylate to produce the same.

EFFECT: enhanced process efficiency.

55 cl, 1 dwg, 7 tbl, 22 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to the improved method for oxidation of (C2-C4)-alkane and preparing the corresponding alkene and carboxylic acid. Method involves addition of this alkane to contact with molecular oxygen-containing gas in oxidative reaction zone and optionally at least one corresponding alkene and water in the presence of at least two catalysts with different selectivity. Each catalyst is effective in oxidation of alkane to corresponding alkene and carboxylic acid resulting to formation of product comprising alkene, carboxylic acid and water wherein the molar ratio between alkene and carboxylic acid synthesized in the reaction zone is regulated or maintained at the required level by regulation the relative amounts of at least two catalyst in the oxidative reaction zone. Also, invention relates to the combined method for preparing alkyl carboxylate comprising abovementioned stage in preparing alkene and carboxylic acid in the first reaction zone. Then method involves the stage for addition of at least part of each alkene and carboxylic acid prepared in the first reaction zone to the inter-contacting in the second reaction zone the presence of at least one catalyst that is effective in preparing alkyl carboxylate to yield this alkyl carboxylate. Also, invention relates to a method for preparing alkenyl carboxylate comprising the abovementioned stage for preparing alkene and carboxylic acid in the first reaction zone and stage for inter-contacting in the second reaction zone of at least part of each alkene and carboxylic acid synthesized in the first reaction zone and molecular oxygen-containing gas in the presence of at least one catalyst that is effective in preparing alkenyl carboxylate and resulting to preparing this alkenyl carboxylate.

EFFECT: improved method for oxidation.

30 cl, 1 dwg, 5 tbl, 14 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

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