Oxirane compounds preparing

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of oxirane compounds comprising the following steps: (i) oxidation of alkylaryl wherein alkyl substitute comprises from 2 to 10 carbon atoms to yield alkylaryl hydroperoxide; (ii) contacting at least part of alkylaryl hydroperoxide prepared at the step (i) with olefin at the temperature range 0-200°C and under pressure in the range 1-100 x 105 H/m2 in the presence of a catalyst comprising titanium on silicon dioxide and/or silicate to yield oxirane compound and alkylaryl hydroxyl; (iii) optional interaction of at least part of alkylaryl hydroperoxide prepared at the step (i) to yield phenol and ketone; (iv) separation of oxirane compound from the reaction product from the step (ii0, and (v) contacting at least part of the reaction product no containing oxirane with hydrogen at temperature 100-330°C and under pressure 0.1-50 x 105 H/m2 in the presence of the hydrogenation catalyst to yield alkylaryl and at least part of the latter is re-circulated to the step (i) wherein the hydrogenation catalyst represents catalyst comprising copper compound, zinc compound and at least one compound chosen from the group consisting of aluminum, zirconium, magnesium rare-earth metals and their mixtures. Invention provides the possibility for synthesis of oxirane compounds without necessity for simultaneous synthesis of other compounds.

EFFECT: improved method of synthesis.

5 cl, 7 ex

 

The present invention relates to a method for producing compounds of oxirane.

Methods for obtaining compounds of oxirane, such as propylene oxide, known for a long time. US-A-3350422 describes a process involving the interaction refinancing compounds, preferably propylene, with organic hydropredict in the presence of an effective catalytic amount of a soluble vanadium compounds in dissolved form. Stated that during the epoxidation reaction organic Gidropress almost quantitatively converted into the corresponding alcohol. Alcohol can be extracted as a by-product, or may be subjected to reverse transformation into Gidropress as a result of dehydration to olefins, hydrogenation of the olefin and its oxidation to gidroperekisi or hydrogenolysis to hydrocarbons with subsequent oxidation to gidroperekisi.

NL-C-1010372 describes a process involving the interaction of propene with hydropredict ethylbenzene with obtaining propylene oxide and 1-phenylethanol. 1-Phenylethanol then dehydration getting styrene, which is a useful source material for other chemical reactions. NL-C-1012749 describes a similar method, according to which propylene is subjected to interaction with hydropredict cumene, getting probenecid and 2-phenyl-2-propanol. Indicates that the last then, for example, which indicate dehydration in alpha methylsterol, which, as indicated, is industrially applicable connection.

Can often be found suitable outputs for many products, obtained as a by-product in the known methods of producing compounds of oxirane. However, it may be appropriate to receive only one connection oxirane, such as propylene oxide.

In EP-B-609455 describes a method for cresol by (1) oxidation of cumene with obtaining the solution of oxidation products containing tertiary hydropeaking and primary Gidropress, (2) recovery of primary gidroperekisi, (3) decomposition of the reaction mixture with getting cresol and some by-products, and (4) hydrogenation of the decomposed mixture with the transformation of part of the products in the cumene and/or cresol. EP-IN-609455 applies only to obtain cresol.

Developed a method that provides the possibility of obtaining compounds of oxirane without the need to simultaneously obtain other compounds. Despite the fact that some stages of the method in accordance with the present invention in themselves known, per se, in the known methods there is no description or indication of a Union of the specified stages of the way this particular way.

The present invention relates to a method for producing compounds of oxirane, including:

(i) oxidation of alkylaryl, in the cat the rum alkyl substituent contains from 2 to 10 carbon atoms, receiving gidroperekisi of alkylaryl,

(ii) contacting at least part of gidroperekisi of alkylaryl obtained in stage (i), with an olefin at a temperature in the range from 0 to 200°and a pressure in the range from 1 to 100×105N/m2in the presence of a catalyst containing titanium on silica and/or silicate, to obtain the compounds of oxirane and alkylaryl - hydroxyl,

(iii) an optional interaction, at least part of gidroperekisi of alkylaryl obtained in stage (i), with phenol and ketone,

(iv) the branch connection of oxirane from the reaction product of stage (ii)

(v) contacting at least part of the reaction product, which was separated oxiran, with hydrogen at a temperature of from 100 to 330°and a pressure of from 0.1 to 50×105N/m2in the presence of a hydrogenation catalyst, obtaining alkylaryl at least part of which is recycled to stage (i), where the hydrogenation catalyst is a catalyst comprising copper, a compound of zinc and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, rare earth metals and mixtures thereof.

In US-A-3350422 indicated that alcohol can be subjected to reverse transformation into his Gidropress by dehydration to olefins, hydrogenation OLE the ins and oxidation to gidroperekisi, or hydrogenolysis to hydrocarbons with subsequent oxidation to gidroperekisi. However, in US-A-3350422 there is no specific information about how alcohol can be subjected to reverse transformation into his Gidropress technically and commercially attractive way.

It was unexpectedly found that the application of the method in accordance with the present invention hydroxide alkylaryl can be turned into alkylaryl with hydrogen and in the presence of a hydrogenation catalyst. In many cases, unwanted side products formed in the previous phase, also turn in the desired alkylaryl. The latter is attractive because it increases the overall output method.

Despite the fact that ethylbenzene is a alcylaryl connection, currently the most widely used in the preparation of the compounds of oxirane, it was found that stage (i) of the method can be carried out with a greater degree of conversion and higher selectivity if applicable alcylaryl connection represents an alkyl benzene in which the alkyl substituent is a branched alkyl substituent comprising from 3 to 10 carbon atoms. More preferred alcylaryl compound contains 1 or 2 alkyl substituent. Alcylaryl soy is inania, containing several deputies, has the advantage that it can contain multiple hydropeaking groups. However, due to possible side reactions it is preferred that no more than 3 substituents, more preferably not more than 2 substituents. Most preferably alcylaryl connection is a cumene and/or di(isopropyl)benzene. Despite the possibility of using mixtures of different alcylaryl compounds, it is preferable to use one type of connection, in order to be able to optimize the process conditions for this particular connection.

Oxidation of alkylaryl can be carried out in any suitable way known in this field. The oxidation can be carried out in the liquid phase in the presence of a diluent. Such a diluent is preferably a compound that is liquid under reaction conditions and does not react with the starting materials and the resulting product. However, the diluent may also be a connection, necessarily present during the interaction. For example, if alkylaryl is a cumene, the diluent may also be a cumene.

The product obtained in stage (i), can be used as such in stage (ii), or may be a preference for the equipment compartment of some compounds or using only part of the obtained product and use the remaining part in another process.

Part of the product from step (i) preferably used in stage (iii), namely at the interface between the gidroperekisi of alkylaryl for the production of phenol and ketone. The resulting ketone may contain substituents. The interaction of gidroperekisi of alkylaryl can be made in the contact of gidroperekisi of alkylaryl with acid catalyst, such as acid catalysts containing sulfur. As the acid catalyst can be used sulfuric acid, hydrochloric acid, perchloric acid, sulfur dioxide and sulfur trioxide; organic acids, such as benzolsulfonat acid, p-toluensulfonate acid, cresolsulfonephthalein acid and Chloroacetic acid; solid acids such as silica, alumina, alumina and acidic ion-exchange resin; heteroalicyclic, such as wolframalpha acid, wolframalpha acid and molybdophosphoric acid. Preferably the use of sulfuric acid and/or cresolsulfonephthalein acid. The amount used of the catalyst is usually in the range of from 0.0001 to 1 wt.% in calculating the treated reaction mixture. The reaction temperature is usually in the range from 30 to 150°C.

Alkylaryl may be subjected to interact after separation of other compounds from the reaction product of stage (i). is, however, preferable to expose a portion of the reaction product of stage (i) directly decomposition reaction in stage (iii).

The reaction in stage (iii) is usually formed by-products. Often formed as by-products are ethylbenzene and 1-methylsterol. To further enhance the yield of this method, the desired products is phenol and the ketone may be separated from the reaction product of stage (iii), after which the remainder of the reaction product or part is subjected to hydrogenation in stage (v). Therefore, the method in accordance with the present invention preferably includes separating at least part of the phenol and ketone from the reaction product of stage (iii) and contacting the remaining reaction product or part thereof with hydrogen at stage (v). The compounds obtained in stage (iii) and preferably directed to the step (v), are ethylbenzene and 1-methylsterol. Therefore, any fraction of the reaction product of stage (iii)is directed to the step (v), preferably contains ethylbenzene and/or 1-methylsterol. The reaction product of stage (iii) can be directed to the step (v) as received, or prior to the step (v) the reaction product of stage (iii) is combined with the reaction product of stage (iv), from which it was separated connection of oxirane.

The desired phenol and the ketone may be separated from the reaction product of stage (iii) in any manner known to the expert in this area is. The phenol and the ketone is preferably essentially removed from the reaction product of stage (iii), while at least part of the reaction product comprising phenol and a ketone, send it back for inclusion in the integrated process.

If necessary, turning part of gidroperekisi of alkylaryl in the phenol and ketone preferably, alkylaryl was a cumene, producing phenol and acetone in the stage (iii).

At stage (ii) hydropeaking of alkylaryl obtained in stage (i), is subjected to contact with the olefin in the presence of a catalyst, receiving the connection oxirane and hydroxyalkylated. The catalyst suitable for use in this method includes titanium on silica and/or silicate. The preferred catalyst described in EP-B-345856. This catalyst contains titanium in chemical combination with solid silica and/or inorganic silicate and can be obtained by (a) impregnating silicon compound with a stream of gaseous titanium tetrachloride, (b) calcination of the product of the interaction obtained in stage a), and (C) hydrolysis of the product from step b). The interaction usually takes place at a moderate temperature and pressure, in particular at a temperature in the range from 0 to 200°C, preferably in the range from 25 to 200°C. the Exact amount of pressure the e matter as long until it is able to maintain the reaction mixture in the liquid state. Sufficient may be atmospheric pressure. In General, the pressure may be in the range from 1 to 100×105N/m2.

The olefin used in the method in accordance with the present invention, depends on the received connection oxirane. The olefin preferably contains from 2 to 10 carbon atoms, more preferably from 2 to 8 carbon atoms. Most preferably, the olefin is a propene.

At the end of the epoxidation reaction liquid mixture containing the desired product separated from the catalyst. Then the connection of oxirane can be separated from the reaction product by any suitable method known to the person skilled in the art. The liquid reaction product can be finished with the use of fractional distillation, selective extraction and/or filtration. The catalyst, any present solvent and any unreacted olefin or Gidropress of alkylaryl can be recycled for further use.

Stage (ii) of the method can be carried out with the catalyst in the form of mist, moving or fluidized bed. However, for large-scale industrial applications, it is preferable to the fixed layer. The method can be carried out in the first is methodological, semi-continuous or continuous mode. The liquid containing the reagents can then be filtered through a layer of catalyst, in order resulting from the reaction zone of the flow was essentially free of catalyst.

Then at least part of the reaction product containing hydroxyalkylated from which it was separated connection of oxirane, is subjected to hydrogenation. Used the hydrogenation treatment includes contacting the reaction product with hydrogen at a temperature of from 100 to 330°C, preferably from 140 to 330°C, preferably from 180 to 330°C, preferably from 180 to 320°C and a pressure of from 0.1 to 100×105N/m2, more preferably from 0.1 to 50×105N/m2most preferably from 0.1 to 30×105N/m2. The ratio (mol./mol.) hydrogen to the hydroxide alkylaryl provided in contact with the catalyst, is preferably at least 0.5, and more preferably, at least, 1,0, most preferably, at least, 1,4.

Catalysts suitable for the hydrogenation of at least part of the reaction product containing hydroxyalkylated from which it was separated connection of oxirane, are the catalysts described in US 5475159. Such catalysts are catalysts comprising a compound of the honey is, the connection of zinc and at least one compound selected from the group comprising aluminum, zirconium, magnesium, rare earth metal, and mixtures thereof. It was found that such catalysts provide good results at a relatively low temperature. At stage (v) of this method such catalysts are preferably used at a temperature of from 100 to 250°C. Such catalysts preferably include from about 10 to 80 wt.% copper in the calculation of the oxide of the total mass of the catalyst. In addition, such catalysts preferably contain from about 10 to 80 wt.% zinc in the calculation of the oxide of the total mass of the catalyst. The preferred catalyst contains from about 10 to 80 wt.% copper in the calculation of the oxide by weight of the total catalyst, from about 10 to 80 wt.% zinc in the calculation of the oxide by weight of the total catalyst and from about 0.1 to 20 wt.% rare earth metal based on the oxide of the total mass of the catalyst. The following preferred catalyst contains from about 10 to 80 wt.% copper in the calculation of the oxide by weight of the total catalyst, from about 10 to 80 wt.% zinc in the calculation of the oxide by weight of the total catalyst and from about 0.05 to 30 wt.% aluminum on the oxide basis by weight of the total catalyst. The following preferred catalyst contains approximately is about 10 to 80 wt.% copper in the calculation of the oxide of the total mass of the catalyst, from about 10 to 80 wt.% zinc in the calculation of the oxide by weight of the total catalyst and from about 0.05 to 30 wt.% zirconium in the calculation of the oxide of the total mass of the catalyst. Another preferred catalyst contains from about 10 to 80 wt.% copper in the calculation of the oxide by weight of the total catalyst, from about 10 to 80 wt.% zinc in the calculation of the oxide by weight of the total catalyst, from about 0.05 to 30 wt.% zirconium in the calculation of the oxide by weight of the total catalyst and from about 0.05 to 30 wt.% aluminum on the oxide basis by weight of the total catalyst. And the following preferred catalyst contains from about 10 to 80 wt.% copper in the calculation of the oxide by weight of the total catalyst, from about 10 to 80 wt.% zinc in the calculation of the oxide by weight of the total catalyst, from about 0.05 to 30 wt.% magnesium in the calculation of the oxide by weight of the total catalyst and from about 0.1 to 20 wt.% rare earth metal based on the oxide of the total mass of the catalyst.

After hydrogenation the hydrogenation product can be recycled completely or partially. When recycling is only part of the hydrogenated product of the desired fraction can be separated by any suitable method known to the expert in this field.

The method in accordance with the present invention is illustrated in the following is the reamers.

Example 1

The epoxidation catalyst is a catalyst containing titanium on silicon dioxide, obtained in accordance with the description given in example EP-A-345856.

The catalyst hydrogenization is a catalyst containing copper, zinc and zirconium, obtained in accordance with example 3 in US-A-5475159.

Fresh cumene and recycled cumene served in the reactor. Within 8 hours through the lower part of the reactor bubbled air produced in the upper part of the reactor. The resulting reaction product contains 28 wt.% the gidroperekisi hydroperoxide, 70 wt.% cumene and 2 wt.% other compounds.

The reaction mixture containing about 6 mol of 1-octene per mole of gidroperekisi cumene, served in the reactor containing the above-described fresh epoxidation catalyst at a temperature of 40°C. octene Oxide is separated. It was found that 55 wt.% 1-octene was converted into the oxide, octene.

A mixture containing 17 wt.% 2-phenyl-2-propanol and 83 wt.% cumene, is subjected to contact with hydrogen in the presence of the above catalyst for the hydrogenation at a temperature of 140°and a pressure of 20×105N/m2within 2 hours. The resulting product does not contain ISO-propylcyclohexane and contains 86 wt.% cumene, 10 wt.% 2-phenyl-2-propanol and 4 wt.% 1-methylstyrene.

Example 2 (comparative)

A mixture containing 17 wt.% -phenyl-2-propanol and 83 wt.% cumene, subjected to contact with hydrogen in the presence of the above-described hydrogenation catalyst comprising 5 wt.% palladium on the carrier from coal, at a temperature of 225°and a pressure of 20×105N/m5within 2 hours. The resulting product contains 1 wt.% 2-phenyl-2-propanol, 94 wt.% cumene, 3 wt.% ISO-propylcyclohexane and 2 wt.% other compounds.

Example 3 (comparative)

Repeat the experiment of example 2, except that the temperature is 280°C. the resulting product does not contain 2-phenyl-2-propanol and contains 89 wt.% cumene, 10 wt.% ISO-propylcyclohexane and 1 wt.% other compounds.

Example 4

Fresh ethylbenzene and recycled ethylbenzene fed into the reactor. Within 8 hours through the lower part of the reactor bubbled air produced in the upper part of the reactor. During the reaction the reactor is cooled due to the exothermic nature of the oxidation. The resulting reaction product contains 10 wt.% the gidroperekisi ethylbenzene, 88 wt.% ethylbenzene and 2 wt.% other compounds.

The reaction mixture containing about 6 mol of 1-octene per mole of gidroperekisi ethylbenzene, served in a reactor containing described in example 1 fresh epoxidation catalyst at a temperature of 40°C. octene Oxide is separated. It was found that 41 wt.% 1-octene was converted into the oxide, octene.

Example 5

Cheese is e, used in examples 5-7, has the following composition:

the cumene74,78%
1-methylsterol0,8%
2-phenyl-2-propanol24,5%

According to analysis by gas chromatography raw materials do not contain heavy compounds comprising at least 10 carbon atoms (C10+ material).

The hydrogenation catalyst is a catalyst used in example 1, containing copper, zinc and zirconium and obtained in accordance with example 3 in US-A-5475159.

Fixed bed of hydrogenation catalyst is subjected to contact with the raw material with volume and mass the average hourly feed rate (WHSV) of 1.0 h-1(33,64 g of material per hour), the temperature in the reactor 200°C, working pressure in the reactor 20x105N/m2and 0.8 mol of hydrogen per mole of the supplied 2-phenyl-2-propanol. Receive a product having the following composition:

the cumene93.1%of
1-methylsterol0,7%
2-phenyl-2-propanol5,9%
C10+ material0,3%

Example 6

Example 5 is repeated, except that the amount of hydrogen is 1.6 mol of hydrogen per mole of the supplied 2-phenyl-2-p is OpenAL. Other reaction conditions are as follows: volume-mass average hourly feed rate of 1.0 h-1(33,64 g of material per hour), the temperature in the reactor 200°and the operating pressure in the reactor 20x105N/m2. The resulting product has the following composition:

the cumene97,3%
1-methylsterol0,3%
2-phenyl-2-propanol0,1%
C10+ material2,3%

Example 7

Example 6 is repeated, except that the temperature in the reactor was raised to 220°C. Other reaction conditions are as follows: the flow rate of hydrogen to 1.6 mol of hydrogen per mole of the supplied 2-phenyl-2-propanol, WSHV 1,0 h-1(33,64 g of material per hour) and the working pressure in the reactor 20x105N/m2. The resulting product has the following composition:

the cumeneof 97.8%
1-methylsterol0,0%
2-phenyl-2-propanol0,0%
C10+ material2,2%

1. The method of obtaining compounds of oxirane, including

(i) oxidation of alkylaryl, in which the alkyl substituent contains from 2 to 10 carbon atoms, with taking the gidroperekisi alkilani is and,

(ii) contacting at least part of gidroperekisi of alkylaryl obtained in stage (i), with an olefin at a temperature of from 0 to 200°and a pressure of from 1 to 100×105N/m2in the presence of a catalyst containing titanium on silica and/or silicate, to obtain the compounds of oxirane and alkylarylsulfonate,

(iii) an optional interaction, at least part of gidroperekisi of alkylaryl obtained in stage (i), with phenol and ketone,

(iv) the branch connection of oxirane from the reaction product from stage (ii) and

(v) contacting at least part of the reaction product, which was separated oxiran, with hydrogen at a temperature of from 100 to 330°and a pressure of from 0.1 to 50×105N/m2in the presence of a hydrogenation catalyst to obtain alkylaryl at least part of which is recycled to stage (i), where the hydrogenation catalyst is a catalyst comprising copper, a compound of zinc and at least one compound selected from the group consisting of aluminum, zirconium, magnesium, rare earth metals and mixtures thereof.

2. The method according to claim 1, in which alcylaryl connection represents an alkyl benzene in which the alkyl substituent is a branched alkyl substituent containing from 3 to 10 and the Ohm carbon.

3. The method according to claim 1 or 2, in which alcylaryl connection is a cumene and/or di(isopropyl)benzene.

4. The method according to any one of claims 1 to 3, in which at least part of the phenol and the ketone is separated from the reaction product of stage (iii) and either all of the remaining reaction product, or part thereof is brought into contact with hydrogen at stage (v).

5. The method according to any one of claims 1 to 3, wherein in stage (ii) hydropeaking of alkylaryl lead in contact with propene.



 

Same patents:

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of oxirane compounds comprising the following steps: (i) oxidation of alkylaryl to yield alkylaryl hydroperoxide; (ii) contacting at least lesser part of alkylaryl hydroperoxide prepared at the step (i) with olefin in the presence of catalyst to yield oxirane compound and alkylaryl hydroxyl; (iii) separation of oxirane compound from the reaction product from the step (ii), and (iv) contacting at least part of the reaction product no containing oxirane compound with hydrogen to yield alkylaryl and at least of part of the latter is re-circulated to the step (i) and wherein alkylaryl means an alkylaryl compound representing di-(isopropyl)-benzene. Invention provides the possibility for preparing oxirane compound without the necessity for preparing other compounds and reducing the amount of the parent alkylaryl.

EFFECT: improved method of synthesis.

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FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of compounds of oxirane, phenol and ketones and/or aldehydes. Proposed method involves the following steps: (i) oxidation of alkylaryl wherein alkyl substitute comprises from 2 to 10 carbon atoms to yield alkylaryl hydroperoxide; (ii) contacting at least part of alkylaryl hydroperoxide prepared at the step (i) with olefin in the presence of catalyst to yield oxirane compound and alkylaryl hydroxyl; (iii) reaction of at least part of alkylaryl hydroperoxide prepared at the step (i) to yield phenol and ketone and/or aldehyde; (iv) separation of oxirane compound from the reaction product from the step (ii), and (v) contacting at least part of the reaction product no containing oxirane with hydrogen to yield alkylaryl and at least part of the latter is re-circulated to the step (i). Invention provides the development of the combined method for synthesis of oxirane, phenol, ketones and/or aldehydes that allows reducing the amount of by-side products due to their conversion to useful compounds.

EFFECT: improved method of synthesis.

8 cl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of organic hydroperoxide comprising the reduced amount of impurities. Method involves the following steps: (a) oxidation of organic compound to yield the reaction product comprising organic hydroperoxide; (b) contacting at least part of the reaction product comprising organic hydroperoxide with the basic aqueous solution; (c) separation of hydrocarbon phase containing organic hydroperoxide from an aqueous phase; (d) washing out at least part of the separated hydrocarbon phase containing organic hydroperoxide, and (e) contacting at least part of hydrocarbon phase containing organic hydroperoxide with a protective layer comprising a solid adsorbent wherein a solid adsorbent shows porosity 50-98% by volume. Except for, invention proposes a method for preparing oxirane compound from hydrocarbon phase obtained at the step (e) by the method described above and containing alkylaryl hydroperoxide. The presence of the protective layer reduces the pressure increment in the catalyst layer that is caused by the declined content of impurities in the raw comprising alkylaryl hydroperoxide.

EFFECT: improved preparing method.

7 cl, 2 ex

FIELD: industrial organic synthesis.

SUBSTANCE: molybdenum is recovered from catalytic olefin epoxidation products using organic hydroperoxides. Method comprises treating heavy epoxidate fraction with alkali solution, treating resultant spent alkali stream with extractant, and subsequent precipitation of molybdenum trisulfide using sulfur-alkali effluents formed in production of olefins by pyrolysis of hydrocarbon feedstock.

EFFECT: increased molybdenum recovery degree and simplified operation.

11 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes method for epoxydation of olefins with ethyl benzene hydroperoxide in the presence of molybdenum-containing catalyst and nitrogen-containing compound. Derivatives of quinolines or Mannich base or their mixtures are used as nitrogen-containing compound and the mole ratio molybdenum : nitrogen-containing compound is maintained = 1:(0.05-0.4). Invention provides enhancing conversion and selectivity of the epoxydation process of olefins with organic hydroperoxides.

EFFECT: improved method for epoxydation.

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The invention relates to a method of producing accelerated, and more particularly to a method of producing accelerated of the alkene, which used the epoxidation reactors operate in such a way that the service life of the catalyst in the epoxidation increases significantly
The invention relates to the field of petrochemicals

The invention relates to an improved method of epoxidation, which uses a titanium-containing catalyst composition

The invention relates to a system for catalytic conversion and the method of carrying out exothermic reactions between, for example, propylene and hydropredict ethylbenzene to obtain propylene oxide using a solid heterogeneous catalyst

The invention relates to the field of reception of diepoxides conjugated aliphatic dienes, which are used as raw materials for epoxy resins, rubbers, adhesives, stabilizers, blowing agents, surface-active substances are used in biotechnology, the leather industry

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes method for epoxydation of olefins with ethyl benzene hydroperoxide in the presence of molybdenum-containing catalyst and nitrogen-containing compound. Derivatives of quinolines or Mannich base or their mixtures are used as nitrogen-containing compound and the mole ratio molybdenum : nitrogen-containing compound is maintained = 1:(0.05-0.4). Invention provides enhancing conversion and selectivity of the epoxydation process of olefins with organic hydroperoxides.

EFFECT: improved method for epoxydation.

3 cl, 15 ex

FIELD: industrial organic synthesis.

SUBSTANCE: molybdenum is recovered from catalytic olefin epoxidation products using organic hydroperoxides. Method comprises treating heavy epoxidate fraction with alkali solution, treating resultant spent alkali stream with extractant, and subsequent precipitation of molybdenum trisulfide using sulfur-alkali effluents formed in production of olefins by pyrolysis of hydrocarbon feedstock.

EFFECT: increased molybdenum recovery degree and simplified operation.

11 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of organic hydroperoxide comprising the reduced amount of impurities. Method involves the following steps: (a) oxidation of organic compound to yield the reaction product comprising organic hydroperoxide; (b) contacting at least part of the reaction product comprising organic hydroperoxide with the basic aqueous solution; (c) separation of hydrocarbon phase containing organic hydroperoxide from an aqueous phase; (d) washing out at least part of the separated hydrocarbon phase containing organic hydroperoxide, and (e) contacting at least part of hydrocarbon phase containing organic hydroperoxide with a protective layer comprising a solid adsorbent wherein a solid adsorbent shows porosity 50-98% by volume. Except for, invention proposes a method for preparing oxirane compound from hydrocarbon phase obtained at the step (e) by the method described above and containing alkylaryl hydroperoxide. The presence of the protective layer reduces the pressure increment in the catalyst layer that is caused by the declined content of impurities in the raw comprising alkylaryl hydroperoxide.

EFFECT: improved preparing method.

7 cl, 2 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of compounds of oxirane, phenol and ketones and/or aldehydes. Proposed method involves the following steps: (i) oxidation of alkylaryl wherein alkyl substitute comprises from 2 to 10 carbon atoms to yield alkylaryl hydroperoxide; (ii) contacting at least part of alkylaryl hydroperoxide prepared at the step (i) with olefin in the presence of catalyst to yield oxirane compound and alkylaryl hydroxyl; (iii) reaction of at least part of alkylaryl hydroperoxide prepared at the step (i) to yield phenol and ketone and/or aldehyde; (iv) separation of oxirane compound from the reaction product from the step (ii), and (v) contacting at least part of the reaction product no containing oxirane with hydrogen to yield alkylaryl and at least part of the latter is re-circulated to the step (i). Invention provides the development of the combined method for synthesis of oxirane, phenol, ketones and/or aldehydes that allows reducing the amount of by-side products due to their conversion to useful compounds.

EFFECT: improved method of synthesis.

8 cl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of oxirane compounds comprising the following steps: (i) oxidation of alkylaryl to yield alkylaryl hydroperoxide; (ii) contacting at least lesser part of alkylaryl hydroperoxide prepared at the step (i) with olefin in the presence of catalyst to yield oxirane compound and alkylaryl hydroxyl; (iii) separation of oxirane compound from the reaction product from the step (ii), and (iv) contacting at least part of the reaction product no containing oxirane compound with hydrogen to yield alkylaryl and at least of part of the latter is re-circulated to the step (i) and wherein alkylaryl means an alkylaryl compound representing di-(isopropyl)-benzene. Invention provides the possibility for preparing oxirane compound without the necessity for preparing other compounds and reducing the amount of the parent alkylaryl.

EFFECT: improved method of synthesis.

3 cl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes a method for synthesis of oxirane compounds comprising the following steps: (i) oxidation of alkylaryl wherein alkyl substitute comprises from 2 to 10 carbon atoms to yield alkylaryl hydroperoxide; (ii) contacting at least part of alkylaryl hydroperoxide prepared at the step (i) with olefin at the temperature range 0-200°C and under pressure in the range 1-100 x 105 H/m2 in the presence of a catalyst comprising titanium on silicon dioxide and/or silicate to yield oxirane compound and alkylaryl hydroxyl; (iii) optional interaction of at least part of alkylaryl hydroperoxide prepared at the step (i) to yield phenol and ketone; (iv) separation of oxirane compound from the reaction product from the step (ii0, and (v) contacting at least part of the reaction product no containing oxirane with hydrogen at temperature 100-330°C and under pressure 0.1-50 x 105 H/m2 in the presence of the hydrogenation catalyst to yield alkylaryl and at least part of the latter is re-circulated to the step (i) wherein the hydrogenation catalyst represents catalyst comprising copper compound, zinc compound and at least one compound chosen from the group consisting of aluminum, zirconium, magnesium rare-earth metals and their mixtures. Invention provides the possibility for synthesis of oxirane compounds without necessity for simultaneous synthesis of other compounds.

EFFECT: improved method of synthesis.

5 cl, 7 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for interaction of an organic compound with hydroperoxide. Invention describes a continuous method of interaction of organic compound comprising at least one C-C-double bond with hydroperoxide in the presence of a catalyst. Method involves interaction of organic compound at the reaction step (R1) under the range of the own pressure below 100 bars, temperature in the range 0-120°C and in the molar ratio of reacting organic compound to hydroperoxide in the range 0.7-20 with hydroperoxide in the presence of a zeolite-containing catalyst to yield at least one flow of the product (P1). Then at least one flow of the product (P1) is fed to intermediate treatment (Z1) wherein (Z1) forms at least one the hydroperoxide-containing product flow (PZ1) and wherein the intermediate treatment represents distillation separation of hydroperoxide from at least one the product flow (P1) or addition of a base to at least one the product flow (P1) and at least one the product flow is fed to at least in the reaction step (R2) wherein under pressure in the own pressure up to 100 bars, temperature in the range 0-120°C and in the molar ratio of the reacting organic compound to hydroperoxide in the range 0.7-20 hydroperoxide is subjected for interaction with an organic compound in the presence of a zeolite-containing catalyst to yield at least one the product flow (P2) wherein at least one of reaction steps (R1) and (R2) the method involves using the reactors system comprising at least two reactors joined in parallel. Also, invention describes a device for carrying out the interaction of an organic compound with hydroperoxide.

EFFECT: improved method for interaction.

9 cl

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of alkylaryl hydroperoxides useful as starting material in production of propylene oxide and alkenylaryl. Process of invention comprises following stages: oxidation of alkylaryl compound to form reaction product containing alkylaryl hydroperoxide; contacting at least part of reaction product with basic aqueous solution; separation of hydrocarbon phase containing alkylaryl hydroperoxide from aqueous phase; containing at least part of above hydrocarbon phase with aqueous solution containing waste water, said aqueous solution containing less than 0.2% alkali metal and/or salt (determined as ratio of metal component to total amount of solution); and separation of hydrocarbon phase from aqueous phase. By bringing at least part of above hydrocarbon phase containing alkylaryl hydroperoxide into interaction with propylene and catalyst, alkylaryl hydroxide and propylene oxide are obtained. At least part of propylene oxide is then separated from alkylaryl hydroxide. Dehydration of at least part of alkylaryl hydroxide results in formation of alkenylaryl.

EFFECT: reduced amount of contaminating by-products in alkylaryl hydroperoxide preparation stage.

8 cl, 4 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to method for synthesis of alkylaryl peroxide-containing compound. Method involves the following steps: (a) oxidation of alkylaryl compound to yield the alkylaryl hydroperoxide-containing reaction substance; (b) treatment of at least part of the reaction substance containing alkylaryl hydroperoxide synthesized at the step (a) wherein this the reaction product comprises less 0.05% of sodium (by mass); (c) separation of product synthesized at the step (b) for hydrocarbon phase containing alkylaryl hydroperoxide and an aqueous phase; (d) repeating steps (b) and (c) by one or some time being optionally. Also, synthesis of alkylaryl hydroxide involves the additional treatment step (e) of at least part of hydrocarbon phase containing alkylaryl hydroperoxide synthesized at steps (c) or (d), olefin and a catalyst to yield alkylaryl hydroxide and oxirane compounds, and (f) separation of at least part of oxirane compound from alkylaryl hydroxide. Synthesis of alkenylaryl involves the additional step (g) of dehydration of at least part of alkylaryl hydroxide synthesized at step (f). Invention provides simplifying the technological process resulting to synthesis of improved substance containing alkylaryl hydroperoxide from which alkylaryl hydroxide is prepared followed by preparing alkenylaryl.

EFFECT: improved method of synthesis.

11 cl, 1 tbl, 6 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of styrene. At the first step the method involves interaction of ethylbenzene hydroperoxide with propene in the presence of catalyst to yield propylene oxide and 1-phenylethanol followed by separate treatment of reaction flow and removing propylene oxide. At the second step the method involves interaction of 1-phenylethanol-containing distillate with a heterogenous dehydration catalyst at temperature 150-320°C to obtain styrene. Distillate contains 0.30 wt.-%, not above, compounds of molecular mass at least 195 Da. Invention provides decreasing the content of by-side compounds in styrene and to enhance it's the conversion degree.

EFFECT: improved method of synthesis.

3 cl, 3 tbl

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