Method for preparing compounds of oxirane, phenol, ketones and/or aldehydes

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

 

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 of olefin-unsaturated 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 all Laut dehydration in alpha methylsterol, which, as indicated, is industrially applicable connection.

Another way in which the use of gidroperekisi, is the way in which phenol and acetone receive, using cumene. This method usually involves the oxidation of cumene in hydropeaking cumene and the transformation of gidroperekisi hydroperoxide into phenol and acetone, preferably using an acid catalyst. This method is described in EP-A-361755.

It was found that it is expedient to combine the method of obtaining compounds of oxirane and the way to obtain a ketone and/or aldehyde and phenol. Such a combined method not only provides the advantage of reducing the scale of gidroperekisi, but, as it was unexpectedly set, unwanted by-products of one method can be converted into the desired products other way.

Another advantage of combining methods in comparison with the method of obtaining only compounds oxirane is that in the United way's just part of the gidroperekisi of alkylaryl turn back to the original alcylaryl connection that provides education to the smaller amount of by-products compared with the way in which alkylaryl recycle completely. In the methods of the latter species usually requires diverting the flow to prevent excessive formation of side products is mswb. The disadvantage of diverting flow is that of the process also removes the desired connection.

Despite the fact that the components of the method in accordance with the present invention are known per se, in the previous methods, there is no description or indication of the consolidation methods in accordance with the present invention.

The present invention relates to a method for producing compounds of oxirane, phenol and ketones and/or aldehydes, including:

(i) oxidation of alkylaryl receiving gidroperekisi of alkylaryl,

(ii) contacting at least part of gidroperekisi of alkylaryl obtained in stage (i), with an olefin in the presence of a catalyst to obtain the compound of oxirane and alkylaryl-hydroxyl,

(iii) communicating at least part of gidroperekisi of alkylaryl obtained in stage (i), to obtain a phenol and a ketone and/or aldehyde,

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

(iv) contacting at least part of the reaction product, which was separated oxiran, with hydrogen to obtain alkylaryl at least part of which is recycled to stage (i).

Although ethylbenzene is a alcylaryl connection, currently most often used when the connection of oxirane, it was found that stage (i) :the BA can be performed with a higher degree of conversion and higher selectivity in the case if used 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 compound containing several deputies, has the advantage that it can contain multiple hydropeaking groups. However, due to possible adverse reactions it is preferred that no more than 3 substituents, more preferably, not more than 2 substituents. More preferably, alcylaryl connection is a cumene and/or di(isopropyl)benzene. Although there may be used mixtures of different alcylaryl compounds, it is preferable to use one type of connection to ensure optimization of conditions for this particular connection. Most preferably, alcylaryl connection is a hydroperoxide or di(isopropyl)benzene.

Alkylaryl applicable in the present invention, can be obtained by any suitable method known to the person skilled in the art. A suitable method of producing cumene described in EP-A-361755 and in EP-A-371738.

Oxidation of alkylaryl can be carried out in any suitable way known in this about the region. 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) and stage (iii), or it may be preferred separation of some compounds or using only part of the product obtained by the method in accordance with the present invention, and using the remaining part in another process.

Part of the product from step (i) used in stage (iii), namely, the reaction of the gidroperekisi of alkylaryl obtaining phenol and ketone and/or aldehyde. The resulting ketone may contain substituents. The reaction 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, bookish sulfur trioxide and sulfur; organic acids, such as benzolsulfonat acid, p-toluensulfonate acid, cresolsulfonephthalein acid and Chloroacetic acid; solid acids such as ion exchange resins from 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 from 0.0001 to 1% wt. in calculating the treated reaction mixture. The reaction temperature is usually from 30 to 150°C.

Gidropress of alkylaryl can be subjected to the reaction in stage (iii) after the separation of other compounds from the reaction product from step (i). However, it is 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 of the phenol and the ketone and/or aldehyde can be separated from the reaction product of stage (iii), after which the remainder of the reaction product or part is subjected to hiderow is at the stage of (v). Therefore, the method in accordance with the present invention preferably includes separating at least part of the phenol and the ketone and/or aldehyde from the reaction product from step (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 from step (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) in the form as it is, either prior to the step (v) of the reaction product from step (iii) is combined with the reaction product of stage (iv), from which it was separated connection of oxirane.

The desired phenol and a ketone and/or aldehyde can be separated from the reaction product of stage (iii) in any manner known to the person skilled in the art. Preferably, the phenol and the ketone and/or aldehyde essentially removed from the reaction product from step (iii), whereas at least part of reaction products other than the phenol and the ketone and/or aldehyde, sent back for use in the combined process.

There is typically no need for the removal of heavy by-products after the application of the program of the United way in accordance with the present invention, because a sufficient amount of heavy by-products are removed at stage (iii). However, if it is preferred to remove extra heavy by-products, it is preferably carried out by removing the heavy by-products from the reaction product of stage (iii) after removing essentially of phenol and ketone and/or aldehyde and to return at least part of the remaining reaction product back into the process.

If light by-products must be removed from the United way in accordance with the present invention, such removal is preferably carried out until recirculatory reaction products in accordance with the present invention at stage (i) of this method. Light by-products are preferably removed from the reaction product of stage (v) and/or the reaction product of stage (iii), from which was removed at least part of the phenol and the ketone and/or aldehyde.

Alkylaryl used in the method in accordance with the present invention, is preferably cumene, because it leads to a commercially attractive compounds 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, hydroc alkylaryl. The catalyst, which is suitable for use in this method includes titanium on silica and/or silicate. The preferred catalyst described in EP-B-345856. Such a catalyst includes titanium in chemical combination with solid silica and/or inorganic silicalite and may be obtained (a) application of silicon compound flow of gaseous titanium tetrachloride, (b) calcining the reaction product 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°preferably in the range from 25 to 200°C. the Exact pressure value does not matter as long as it is capable of maintaining the reaction mixture in the liquid state. Sufficient may be atmospheric pressure. In General, the pressure can be from 1 to h5N/m2.

The olefin used in stage (ii) of 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 is separated from the catalysis of the Torah. 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 and any solvent which may be present, and any unreacted olefin or Gidropress of alkylaryl can be recycled for further use.

Stage (ii) of the method can be carried out using 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 a periodic, 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°, predpochtitel is about 180 to 330° C, preferably from 180 to 320°C and a pressure of from 0.1 to h5N/m2more preferably, from 0.1 to h5N/m2most preferably, from 0.1 to h5N/m2. Processing the hydrogenation is preferably carried out in the presence of a hydrogenation catalyst. Typically, the catalyst contains a metal on a solid medium, with the specified metal catalyzes the hydrogenation. The preferred catalysts are the catalysts containing from 0.5 to 5% wt. metal or its compounds on the media. The metal present in the form of a metal or its compounds, preferably represents one or more metals selected from groups 1b, 2b, 3a, 4a, 4b, 5b, 6b, 7b and 8 of the Periodic table of the elements described in the Handbook of Chemistry and Physics, 63rdEdition. Most preferably, the metal present in the form of a metal or its compound is a palladium. Solid carrier preferably is a coal.

Other catalysts, preferably applicable to 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 copper, a compound of zinc and at least the bottom connection, 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, calculated on the oxide basis, of the total weight of the catalyst. In addition, such catalysts preferably contain from about 10 to 80 wt.%. zinc, calculated on the oxide basis, of the total weight of the catalyst. The preferred catalyst contains from about 10 to 80 wt.%. copper, based on the oxide, by weight of the total catalyst, from about 10 to 80 wt.%. zinc, based on the oxide, by weight of the total catalyst and from about 0.1 to 20% wt. rare earth metal, calculated on an oxide basis, of the total weight of the catalyst. The following preferred catalyst contains from about 10 to 80 wt.%. copper, based on the oxide, by weight of the total catalyst, from about 10 to 80 wt.%. zinc, based on the oxide, by weight of the total catalyst, and from about 0.05 to 30 wt.%. aluminum, based on the oxide, by weight of the total catalyst. The following preferred catalyst contains from about 10 to 80 wt.%. copper, based on oxide, from which the total mass of the catalyst, from about 10 to 80 wt.%. zinc per oxide, by weight of the total catalyst and from about 0.05 to 30 wt.%. zirconium, calculated on the oxide basis, of the total weight of the catalyst. Another preferred catalyst contains from about 10 to 80 wt.%. copper, based on the oxide, by weight of the total catalyst, from about 10 to 80 wt.%. zinc, based on the oxide, by weight of the total catalyst, from about 0.05 to 30 wt.%. zirconium, based on the oxide, by weight of the total catalyst and from about 0.05 to 30 wt.%. aluminum, based on the oxide, by weight of the total catalyst. And the following preferred catalyst contains from about 10 to 80 wt.%. copper, based on the oxide, by weight of the total catalyst, from about 10 to 80 wt.%. zinc, based on the oxide, by weight of the total catalyst, from about 0.05 to 30 wt.%. magnesium, based on the oxide, by weight of the total catalyst and from about 0.1 to 20% wt. rare earth metal, calculated on an oxide basis, of the total weight of the catalyst.

After interaction with hydrogen at stage (v) the obtained 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.

1. The method of obtaining compounds is of kirana, phenol and ketones and/or aldehydes, including

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

(ii) contacting at least part of gidroperekisi of alkylaryl obtained in stage (i), with an olefin in the presence of a catalyst to obtain the compound of oxirane and alkylarylsulfonate,

(iii) reaction of at least part of gidroperekisi of alkylaryl obtained in stage (i), with phenol and ketone and/or aldehyde,

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

(v) contacting at least part of the reaction product, which was separated oxiran, with hydrogen with getting alkylaryl at least part of which is recycled to stage (i).

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 carbon atoms.

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

4. The method according to any one of claims 1 to 3, in which the by-products of the decomposition obtained in stage (iii), serves on stage (v).

5. The method according to any one of claims 1 to 4, in which in stage (ii) Hydra is a peroxide alkylaryl lead in contact with propene at a temperature of from about 0 to 200° C and a pressure of from 1 to 100×105N/m2in the presence of a catalyst containing titanium on silica and/or silicate.

6. The method according to any one of claims 1 to 5, in which the hydrogenation in stage (v) of the method is carried out at a temperature of from 180 to 330°and a pressure of from 0.1 to 50×105N/m2in the presence of a hydrogenation catalyst.

7. The method according to any one of claims 1 to 6, in which at least part of the phenol and the ketone and/or aldehyde is separated from the reaction product of stage (iii) and the remainder of the reaction product or part is brought into contact with hydrogen at stage (v).

8. The method according to any one of claims 1 to 7, in which in stage (v), at least part of the reaction product, which was separated connection of oxirane obtained at stage (iv), lead into contact with hydrogen and a catalyst containing a compound of copper, a compound of zinc and at least one compound selected from the group comprising aluminum, zirconium, magnesium, rare earth metal, and mixtures thereof.



 

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