Method for preparing oxyrane using peroxide compound

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing oxyrane. Method involves reaction of olefin with peroxide compound in the presence of catalyst and a solvent in at least two reactors arranged in series and each reactor contains part of catalyst. Peroxide compound is added to the first reactor only and the next or the following reactors are fed with peroxide compound presenting in medium preparing from the preceding reactor but not with fresh peroxide compound or used in this preceding reactor. Method provides enhancing output and reducing formation of by-side products.

EFFECT: improved method for preparing.

10 cl, 1 dwg, 2 ex

 

The present invention concerns a method of obtaining oxirane by reaction between the olefin and the peroxide compound in the presence of a catalyst and solvent. In particular, it is concerned with the obtaining of propylene oxide (or oxide epichlorohydrin) by epoxidation of propylene (or allylchloride) using hydrogen peroxide in the presence of a catalyst containing TS-1.

From the prior art known to the receiving of propylene oxide by reaction between propylene and hydrogen peroxide in the presence of TS-1. For example, according to patent US 5,849,937 this method is carried out in several consecutive reactors. In this known method, each reactor from the serial number nourish fresh hydrogen peroxide.

The applicant was found that the power of each reactor fresh hydrogen peroxide becomes impossible to convert all the number of the used hydrogen peroxide without significant formation of by-products and, therefore, to ensure optimal performance.

The present invention is designed to eliminate this disadvantage by using a new method, which allows you to convert 100% of the added amount of hydrogen peroxide with little formation of by-products, without compromising responsiveness.

In this spaziosystem of the present invention is a method of obtaining oxirane by the reaction of an olefin with a peroxide compound in the presence of a catalyst and solvent in at least two reactors arranged in series, each of which contains a portion of the catalyst, according to which the first reactor is injected first portion of the olefin, the solvent and the whole amount of peroxide compounds in the reactor to carry out epoxidation first part of the olefin to the formation of the first part of oxirane from this reactor, remove the medium containing the first part formed of oxirane, solvent, unused peroxide compound and possibly unconverted olefin, in the following reactor enter the environment and another part of the olefin, here also carry out epoxidation another part of the olefin using unused peroxide compounds, extracted from the first reactor, with the formation of another part of oxirane and remove the other part thus obtained of oxirane.

One of the essential features of the present invention is that the peroxide compound is introduced only into the first reactor. The next or following the reactors do not cherish, so fresh peroxide compound, and only peroxide compound present in the environment, derived from the previous reactor, and is not used in the previous reactor. As a rule, in the first reactor together with a peroxide compound injected water. The fact that next(s) of the reactor(s) do not add peroxide compound, allow the us to consume 100% of the total number of used peroxide compounds, without affecting the reaction rate compared with the way in which use the same total amount of peroxide compounds, but each reactor is fed with fresh peroxide compound.

In the method according to the present invention is used, the installation comprising at least two of the epoxidation reactor arranged in series and connected to each other, except at least two successive reaction zones, arranged in the same reactor. I.e., using separate reactors. Each reactor feed olefin. The peroxide compound and the solvent is injected only into the first reactor. Each reactor contains a portion of the catalyst which remains in the reactor. If the catalyst is present in the form of a stationary layer, as a rule, there is no need to take precautions to keep the catalyst in the reactor. Alternatively, the catalyst may be present in the form of particles, at least part of which is in a fluid state, and it does so with the help of liquid flow, or mechanical mixing, or using gas. When liquid flow is recommended to provide a zone of discharge above the fluid layer to stop the motion of the catalyst particles and/or to provide a filter at the exit of the reactor.

Once meets, the installation may include more than two serially connected reactors. In this case, the first reactor of the serial number of feed olefin, a peroxide compound and a solvent, and each subsequent reactor feed olefin and the environment from the previous reactor serial number. Preferably use three consecutive reactor.

In the method according to the present invention, as a rule, in the first reactor is consumed at least 50% of the total amount of peroxide compounds introduced into the first reactor. The best performance is achieved by the consumption in the first reactor is at least 70%. Most often in the first reactor is consumed not more than 99%, preferably not more than 85%. The remaining part is consumed in the following(their) reactor(s).

In accordance with the present invention a method is preferably used reactors of the same size. This allows the transfer of functions from one reactor to another, when the deactivated catalyst in the reactor was replaced with fresh or regenerated catalyst without interrupting the plant operation (so-called “carousel” process).

The first preferred embodiment of the method in accordance with the present invention is to use a catalyst in the form of particles, at least cha is th which is in a fluid state, as described in the patent application filed by the applicant on the same day as the present patent application, titled “Method of obtaining oxirane in the presence of a catalyst in the form of particles” (the contents of which are cited as references). In this case, it is recommended to provide a filter through which passes the environment, leaving the first reactor, before its introduction into the next reactor. This embodiment provides a homogeneous dispersion of the catalyst in epoxygenase reaction medium, normal heat transfer and, therefore, easier to control the reaction temperature.

In the second variant implementation of the method in accordance with the present invention included the following reactor environment is subjected to expansion before its introduction into the next reactor. This option is most applicable when the epoxidation carried out under pressure or in the presence of compounds in the gaseous state. This gaseous compound can be the same olefin (e.g. propylene) or inert gas that is injected into epoxydiols reaction medium to provide movement of oxirane and removal from the reactor, as described in patent application WO 99/48883 filed on behalf of the applicant.

In the third variant of the method in accordance with the present invention included in the following reaction the op environment is first processed for separation formed of oxirane before its introduction into the next reactor. The purpose of this alternative implementation is as fast as possible Department of oxirane from epoxygenase reaction medium immediately after its formation, in order to avoid the formation of by-products by hydrolysis or alcoholysis (methanolysis, if the solvent used methanol) educated oxirane. An advantage of these embodiments is the provision of high selectivity. Separating processing is preferably distillation, as described in a patent application filed in the name of the applicant on the same day as the present patent application, and entitled “Method of obtaining oxirane, including the Department of oxirane from the reaction environment” (the content of which is attached as reference).

A preferred variant of the method in accordance with the present invention is shown schematically in figure 1. In this preferred embodiment, the first reactor 1 contains a portion of the catalyst, preferably in the form of a fluidized bed 2. The reactor 1 is fed by the first part of the olefin via line 3, and then through a pipeline 4 (peroxide connection through the pipe 5, and then through a pipeline 4*and solvent through line 4 from another part of the installation, which will be described below. In the first reactor, the first part of the olefin reacts with the peroxide with whom the Association in the presence of a catalyst with the formation of the first part of oxirane. Go through the pipe 6 of the reactor 1 medium contains a solvent, the first part of oxirane, unused percoidei connection and unconverted olefin. This medium passes through the filter 7 and fed through pipe 8 into the tank 9, where it undergoes expansion. Then through the pipeline 10, this medium is fed to a distillation column 11. At the top of this distillation column 11 remove mixture of oxirane and non-converted olefin. This mixture through the pipeline 12 is served in the condenser 13, where axiron is separated from the unconverted olefins. Unconverted olefin return to the reactor 1 through the piping 14, 3, and 4. The first part of oxirane in the form of the final product is extracted through line 15. In the lower part of the distillation column 11 selected medium containing a solvent is not used in the reactor 1 of peroxide compound and possibly part of the unconverted olefins. This environment, part of which may be, if necessary, recycled to the reactor 1 via line 30, and serves on the pipeline 16 to the second reactor 17, containing another portion of the catalyst, preferably in the form of a fluidized bed 18. The second reactor 17 is fed by the second part of the olefin via line 19. In the second reactor 17 the second part of the olefin reacts with the peroxide compound is not used in the first is auctore, in the presence of a catalyst 18 with the formation of the second part of oxirane. Preferably in the second reactor 17 conditions are such to use all of the amount of peroxide compounds received from the first reactor. Emerging from reactor 17 through the pipeline 20 medium contains in this case, the solvent, the second part of oxirane and unconverted olefin. This medium passes through the filter 21 and line 22 is fed into the tank 23 where it is expanding. After that, through the pipe 24 Wednesday sent to the second distillation column 25. At the top of this distillation column 25 receive the mixture of the second part of oxirane and non-converted olefin. This mixture through the pipe 26 serves to the condenser 27, where the separation of oxirane from non-converted olefin. Unconverted olefin return to the reactor 1 through the piping 28, 14, 3, and 4. The second part of oxirane in the form of the finished product is taken by pipeline 29. In the lower part of the distillation column 25 selected solvent, which is in line 4 returns in the first reactor 1, and waste water, which are removed through the conduit 31.

The catalyst used in the method according to the present invention preferably contains as the active element of the zeolite, preferably of titanium-containing zeolite. Under Titus is nesteriak zeolite understand solid, containing silica with a microporous crystalline zeolite structure type, in which some of the silicon atoms are replaced by titanium atoms. Titanium-containing zeolite preferably has a crystalline structure of ZSM-5, ZSM-11, ZSM-12, MCM-41, ZSM-48. He may also have a crystalline structure of beta zeolite type, preferably not containing aluminum. Suitable zeolites with a range of infrared absorption, constituting approximately 950-960 cm-1. The preferred titanium-containing zeolites silicalite type. The most preferred of them correspond to the formula xTiO2(1-x)SiO2where x is from 0.0001 to 0.5, preferably from 0.001 to 0.05. Materials of this type are known under the name of TS-1 are microporous crystalline zeolite a structure similar to the structure of zeolite ZSM-5.

Used in the method according to the present invention, the catalyst preferably has the shape of particles obtained by extrusion as described in patent application WO 99/24164 filed on behalf of the applicant, or by using spray technology, as described in patent application WO 99/241164 filed on behalf of the applicant. The contents of these two applications is incorporated into the present application by reference.

Used in the method according to the present invention, the solvent may be selected from linear or branched feast upon the R aliphatic alcohols. Alcoholic solvent preferably contains up to 10 carbon atoms, preferably from 1 to 6 carbon atoms. As examples can be mentioned methanol and ethanol. Preferred is methanol.

The number used in the first reactor solvent, as a rule, is at least 25 wt.% the weight of the liquid reaction medium present in the first reactor, in particular at least 40 wt.%, for example, at least 50 wt.%. Usually this number is greater than 99 wt.%, in particular 95 wt.%.

The molar ratio of the olefin and the amount of peroxide compounds, involved in the method according to the present invention, typically, is at least of 0.1, in particular at least 0.2 and preferably at least 0.5 in. Most often, this molar ratio is not more than 100, in particular not more than 50, and preferably not more than 25.

The method in accordance with the present invention can be performed in continuous or batch mode.

When the method in accordance with the present invention is carried out in a continuous mode, as a rule, peroxide compound used in the first reactor in a quantity of at least 0,005 mol per hour and per gram of catalyst present in the first reactor, in particular at least 0.01 mol. To icesto peroxide compounds typically less than or equal to 25 mol, and in particular, less than or equal to 10 mol. The preferred amount of peroxide compounds greater than or equal to 0.03 mol and less than or equal to 2.5 mol.

In the method according to the present invention, the peroxide compound is used preferably in aqueous solution. Typically, the aqueous solution contains at least 2 wt.% peroxide compounds, in particular at least 5 wt.%. Most often it contains not more than 90 wt.% peroxide compounds, in particular 70 wt.%.

The temperature of the reaction between the olefin and the peroxide compound can vary from 10 to 125°C. In the preferred embodiment, described in patent application EP 99/08703 filed on behalf of the applicant, it exceeds 35°to compensate for the gradual deactivation of the catalyst. The temperature can be less than or equal to 40°and preferably be less than or equal to 45°C. the Most preferred temperature is greater than or equal to 50°C. the reaction Temperature is preferably less than 100°C.

In the method according to the present invention, the reaction between the olefin and the peroxide compound may be carried out at atmospheric pressure. It can also be carried out under pressure. Typically, this pressure does not exceed 40 bar. In practice, the most preferred is a pressure of 20 bar.

Peroxide is soedineniya, which can be used in the method according to the present invention are peroxide compounds containing one or more peroxide functional groups (-UN), which can release active oxygen and capable of epoxidation. Good results can be obtained when using inorganic peroxide compounds. For a method suitable hydrogen peroxide and peroxide compounds that can form hydrogen peroxide under the reaction conditions of the epoxidation. More preferred hydrogen peroxide.

If using hydrogen peroxide, the method in accordance with the present invention use an aqueous solution of hydrogen peroxide in the raw, that is, in crude form. For example, you can use the solution obtained by simple extraction of almost pure water from the mixture obtained by oxidation of at least one alkylanthraquinones (a method called “method JSC auto-oxidation”) without subsequent washing and/or cleaning. These initial solutions of hydrogen peroxide, usually contain from 0.001 to 10 g/l of organic impurities, expressed as TOC (total organic carbon). They usually contain metal cations (such as alkaline or alkaline-earth metals, for example, sodium) and anions (such as phosphates, nitrates) with soda is a content of from 0.01 to 10 g/L.

In another embodiment, the method may be used an aqueous solution of hydrogen peroxide obtained by direct synthesis from oxygen and hydrogen in the presence of methanol.

Oxiran, which can be obtained using the method in accordance with the present invention, is an organic compound that contains the group that meets the General formula

Oxiran typically contains from 2 to 10 carbon atoms, preferably from 3 to 6 carbon atoms. Oxirane, preferably obtained using the method in accordance with the present invention are 1,2-epoxypropane and 1,2-epoxy-3-chloropropane. As oxirane preferred 1,2-epoxypropane.

Most suitable for the method in accordance with the present invention, the olefins are olefins containing, as a rule, from 2 to 10 carbon atoms and preferably from 3 to 6 carbon atoms. For this purpose suitable propylene, butylene and allylchloride. Preferred propylene and allylchloride. Most preferred is propylene.

In the method in accordance with the present invention, it may be necessary to control the pH of the liquid phase. For example, during the reaction between the olefin and the peroxide compound should maintain the pH of the liquid phase in the range from 4.8 to 6.5, for example, by zabavljanjeonline (sodium hydroxide) on Wednesday epoxidation, as recommended in the patent application WO 99/48882, filed in the name of the applicant (the contents of which are incorporated into the present patent application by reference). This ground can only be entered in one reactor (for example, the first reactor or in multiple reactors. Preferably its lead in each reactor.

The reaction between the olefin and the peroxide compound can be performed in the presence of salts such as sodium chloride, as described in patent application WO ER 99/08703 in the name of the applicant (the contents of which are incorporated into the present patent application by reference). This salt, you can enter only one reactor (for example, the first reactor or in multiple reactors. Preferably it is introduced into each reactor.

It may be preferable to introduce the olefin diluted by one or more alkanes. For example, you can type in the epoxidation reactors for liquid containing olefin and at least 10 vol.% (in particular, 20%, for example, at least 30 vol.%) one or more alkanes. For example, in the case of the use of propylene can be mixed with at least 10 vol.% propane, when injected into the reactor recycled unconverted propylene. You can also use the source of propylene, not completely cleared from propane.

The following examples are given to illustrate the present invention b is C limiting its scope.

In examples 1 and 2 the calculations were made using the software ASPEN PLUS®manufactured by the company “ASPEN TECHNOLOGY INC., with the introduction of the kinetic parameters of the reaction, defined on the basis of the described tests and equilibrium liquid-vapour, taken from reference books.

Comparative example 1

In this example, the synthesis of propylene oxide is carried out in two successive reactors with intermediate separation of propylene oxide formed in the first reactor, a distillation column. Half of the H2About2fed to the first reactor and the other half in the second. 326,5 KMOL/h of hydrogen peroxide with 1100 KMOL/h of water, divided into two equal parts, each of which contains 163,5 KMOL/h of hydrogen peroxide and 550 KMOL/h of water; the first part is mixed with 1500 KMOL/h of methanol, 250 KMOL/h of propylene and with a fraction recycled from the bottom of the distillation column under pressure sufficient to dissolve all of propylene at the reaction temperature. Reaction medium continuously served at 70°in research reactor containing 600 kg of catalyst. With the cooling system in the reactor keep the temperature in the 70°C.

From the reactor effluent sent to distillation column containing 50 theoretical plates (including the condenser and IP is Arial); nutrition exercise at the level 10 theoretical plates (counting from the condenser); column operates at 1.1 absolute bar (the pressure in the upper part of the column); the temperature in the upper part of the column is maintained at 40°With (partially vaporized distillate); set the level of the molar irrigation equal to 1; the total consumption of distillate is installed in the $ 600 KMOL/h.

Recoverable in the lower part of the column lean mixture with a low content of propylene is divided into two parts, the first of which, containing 90% of the volume of the mixture, to recycle the power of the first reactor; the second, containing the remainder of the mixture obtained in the lower part of the distillation column, mixed with 200 KMOL/h of propylene under pressure sufficient to dissolve all of propylene at the reaction temperature, and continuously injected at 70°With the second research reactor containing 820 kg of catalyst, while in the second reactor with the cooling system temperature is maintained at 70°C.

Effluent from the second reactor contains 24.5 KMOL/HR of unconverted hydrogen peroxide, 209,4 KMOL/h of propylene oxide and 87.7 KMOL/HR-products (mainly methoxypropanol and propandiol); the distillate of the column contains 56.2 KMOL/h of propylene oxide; output3reaches 64,1% when the degree of conversion of the pen is sid hydrogen 92.4 per cent.

Example 2 (according to the invention)

In this example, the synthesis of propylene oxide is carried out in two successive reactors with intermediate separation of propylene oxide formed in the first reactor.

326,5 KMOL/h of hydrogen peroxide in the presence 1100 KMOL/h of water are mixed with 1500 KMOL/h of methanol, 250 KMOL/h of propylene and with a fraction recycled from the bottom of the distillation column, under pressure sufficient to dissolve all of propylene at the reaction temperature. The reaction medium is continuously introduced in the 70°in research reactor containing 600 kg of catalyst. In the reactor, maintain the temperature of 70°using appropriate cooling system.

Effluent from the reactor is sent to a distillation column containing 50 theoretical plates (including condenser and evaporator); nutrition exercise at the level 10 theoretical plates (counting from the condenser); column operates at 1.1 absolute bar (the pressure in the upper part of the column); the temperature in the upper part of the column is maintained at 40°With (partially vaporized distillate); set the level of the molar irrigation equal to 1; the total consumption of distillate is installed in the $ 600 KMOL/h.

Recoverable in the lower part of the column lean mixture with a low content of propylene is divided into two hours and, the first of which, containing 90% of the volume of the mixture, to recycle the power of the first reactor; the second, containing the remainder of the mixture obtained in the lower part of the distillation column, mixed with 200 KMOL/h of propylene under pressure sufficient to dissolve all of propylene at the reaction temperature, and continuously injected at 70°With the second research reactor containing 820 kg of catalyst, while in the second reactor with the cooling system temperature is maintained at 70°C.

Effluent from the second reactor contains 1.9 KMOL/HR of unconverted hydrogen peroxide, 256,5 KMOL/h of propylene oxide and 62.2 KMOL/HR-products (mainly methoxypropanol and propandiol); the distillate of the column contains 88,4 KMOL/h of propylene oxide; output3reaches 78,6% when the degree of conversion of hydrogen peroxide was 99.4%.

1. The method of receiving oxirane by the reaction of an olefin with a peroxide compound in the presence of a catalyst and solvent in at least two reactors arranged in series, each of which contains a portion of the catalyst, according to which the first reactor is injected first portion of the olefin, the solvent and the whole amount of peroxide compounds in the reactor by the epoxidation of the first part of the olefin with the formation of the first hour and oxirane, from this reactor, remove the medium containing the first portion of oxirane, solvent, unused peroxide compound and possibly unconverted olefin, in the following reactor enter the environment and another part of the olefin, here also carry out epoxidation another part of the olefin using unused peroxide compounds, extracted from the first reactor, with the formation of another part of oxirane and remove the other part formed thus oxirane.

2. The method according to claim 1, in which 50 - 99% of the total amount of peroxide compound used in the first reactor is consumed in the first reactor, while the remaining part is used in the following(their) reactor(s).

3. The method according to claim 1 or 2, in which all reactors have the same dimensions.

4. The method according to any one of claims 1 to 3, in which the catalyst is present in each reactor in the form of particles, at least part of which is in a fluid state.

5. The method according to claim 4, in which leaving the first reactor medium passes through the filter before entering the next reactor.

6. The method according to any one of claims 1 to 5, which is a member of the following reactor environment before entering the next reactor is first subjected to extension.

7. The method according to any one of claims 1 to 6, which is a member of the following reactor environment before entering the next reactor is first processed for separation formed of oxirane.

8. The method according to claim 7, in which the dividing processing is by distillation.

9. The method according to any one of claims 1 to 8, in which oxiran represents the epichlorohydrin, the olefin is allylchloride, the peroxide compound is hydrogen peroxide, the solvent is methanol, and the catalyst contains TS-1.

10. The method according to any one of claims 1 to 8, in which oxiran oxide is propylene, the olefin is propylene, the peroxide compound is hydrogen peroxide, the solvent is methanol, and the catalyst contains TS-1.



 

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