Styrene production process

FIELD: industrial organic synthesis.

SUBSTANCE: production of styrene is effected via gas-phase dehydration of 1-phenylethanol at elevated temperature in presence of dehydration catalyst including molded particles of alumina-based catalyst having BET surface area 80 to 140 m2/g and pore volume (Hg) above 0.65 ml/g.

EFFECT: reduced amount of by-products and prolonged service cycle of catalyst.

3 cl, 1 tbl, 5 ex

 

The present invention relates to a method for producing styrene, including gas-phase dehydration of 1-phenylethanol at elevated temperature in the presence of a dehydration catalyst.

The usual way styrene production is joint production of propylene oxide and styrene from ethylbenzene. Generally speaking, this method involves the following stages: (i) interaction of ethylbenzene with oxygen or air to form ethylbenzene hydroperoxide, (ii) interaction thus obtained of hydroperoxide ethyl benzene with propene in the presence of an epoxidation catalyst to obtain propylene oxide and 1-phenylethanol (also known as α-phenylethanol or methylphenylcarbinol), and (iii) the conversion of 1-phenylethanol in styrene by dehydration using a suitable dehydration catalyst.

In itself, the use of catalysts based on aluminum oxide in the dehydration of 1-phenylethanol well known in the prior art.

For example, in the document US-A-3526674 described the use of a catalyst based on aluminum oxide in the liquid-phase dehydration of 1-phenylethanol in styrene, with the specified catalyst based on aluminum oxide is in an appropriate case, the surface area according to BET of from 40 to 250 m2/g and is used in finely dispersed form, i.e. in the form of particles with a size of 0.15 mm (100 mesh) or less.

The document is the US A-3658928 described by way of gas-phase dehydration of 1-phenylethanol in styrene in the presence of a controlled amount of added steam and in the presence of a catalyst, which in a suitable case is available for purchase by the catalyst based on aluminum oxide, such as Harshaw Al-0104.

The catalyst Harshaw Al-0104 has a pore volume of about 0.35 ml/g, the Method of dehydration, using catalysts based on aluminum oxide (alumina: Al2About3), especially suitable for such a method was described in document WO 99/58480. The use of such catalysts makes it possible beneficial conversion of 1-phenylethanol in styrene without many of the disadvantages of using catalysts of the prior art. However, even the use of these improved catalysts still leads to the formation of heavy by-products, typically up to 5% of oligomers and polymers of styrene. These heavy by-products not turn on and, therefore, reduce the total yield of the target styrene. In addition, these high molecular weight by-products tend to occupy the pores of the catalyst, then the catalyst can no longer be used for the conversion of 1-phenylethanol in styrene. This requires a stage of regeneration of the catalyst, which adversely increases the cost of the process.

Thus, the purpose of the present invention is to find a catalyst for gas-phase dehydration of 1-phenylethanol in styrene, in which the styrene is obtained with improved selectivity and conversion of 1-phenylethanol you to the Sarafovo time to maintain at a high level. This means that to regenerate the catalyst you need less.

In the context of this application, the term "styrene" also includes substituted styrene, which refers to styrene containing one or as alternates related to the aromatic cycle or vinyl group. Such substituents generally include alkyl groups such as methyl or ethyl groups. Similarly, the term "1-phenylethanol" also includes substituted 1-phenylethanol having the same substituents as the corresponding substituted styrene.

It was found that the dehydration catalyst based on aluminum oxide, whose surface area by the BET ranges from 80 to 140 m2/g and a pore volume (Hg) exceeds that of 0.65 ml/g, suitable for producing styrene by gas-phase dehydration of 1-phenylethanol at elevated temperatures along with the fact that the dehydration of 1-phenylethanol maintained at a high level for a long time. In addition, it was found that this method produces less heavy by-products than with catalysts of the prior.

Pore volume (Hg) catalyst for use in the present invention is greater than 0.65 ml/g, Preferably the pore volume is not more than 1.0 ml/g, More precisely, the catalyst preferably has a pore volume (Hg) from 0.75 to 0.85 ml/year

The area of the surface of the and BET can be measured in any way, which is known as suitable for any specialist in this field. The terms "pore volume (Hg)" means a pore volume, measured by mercury. Suitable methods of measuring porosity using mercury is also well-known specialist in this field.

Molded catalysts based on aluminum oxide with the properties required for use in this invention can be prepared according to procedures well known in the prior art, for example, by extrusion of a paste of aluminum oxide or a precursor of aluminum oxide, followed by calcination. Examples of precursors of alumina hydrates are aluminum oxide such trihydrate alumina, Al2O32O (also known as gibbsite or bayerite) and aluminum hydroxide AlOOH (also known as boehmite or pseudoboehmite). These precursors of the oxide of aluminum is converted to aluminum oxide in the process of roasting. Usually in this process the powder of aluminum oxide or powder precursor of alumina is first mixed with powder binder (optional). Suitable binder materials include inorganic oxides, as the oxides of silicon, magnesium, titanium, aluminum, zirconium, and silicon-aluminum. The weight ratio of the binder to the powder of aluminum oxide can range from 0 (no binder) to 90:10. Usually able to ekstradirovan the s a mixture is prepared from the solid (powders of aluminum oxide and, perhaps binder) and water by mixing and stirring the components and passing the mixture in the extruder. This is capable of extruding the mixture looks like a paste. Specialists usual level in this area is able to optimize the procedure of mixing/stirring to obtain capable of extruding the paste and to choose the most suitable conditions astrogirlbunny. In addition to aluminum oxide, optionally a binder and water, extruding the paste usually contains also extrusion additives to improve the extrusion process. Such extrusion additives known in the art and include, for example, baptistery and flocculants. Baptistery contribute to a more dense packing of the particles in the extrusion mixture, and flocculants facilitated the addition of water. Suitable baptistery known in the prior art and include monovalent inorganic acid (e.g. hydrochloric acid and nitric acid) and organic acids, such as aliphatic monocarboxylic acid, an acyclic monocarboxylic acids and fatty acids. Suitable flocculants are also well known and they include polyelectrolytes, such as commercially available under the trademarks of NALCO and SUPERFLOC. Also, to increase the porosity of the final extrudate can be applied viraemia materials. Examples of viharamahadevi are polyethylene oxide, methylcellulose, ethylcellulose, latex, starch, nut shells or flour, polyethylene or any polymeric microspheres or micrococci.

The catalyst is particularly suitable for use in this invention may be made of pseudoboehmite (AlOOH). This powder is available for purchase from the company, Criterion Catalyst.

Suitable for extruding the mixture or paste obtained as described above, then subjected to extrusion processing. This extrusion processing can be carried out in the usual extrusion technique known in the prior art. At the exit of the extruder there is a hole, which gives the extruded mixture selected form when leaving it extruder. If you want to get the extrudate spherical shape, wet extrudate emerged from the extruder before it is subjected to calcination, is first attached to the spherical shape in a suitable device give a spherical shape. The catalyst particles can have any shape, including spherical, cylindrical, trendalicious, chetyrehkolkoy, star, ring, cross, etc. Soft extrudates, obtained as described above, then dried (optional) and then subjected to a stage of annealing. The catalyst with the desired properties can be obtained by drying the extrudates at a temperature from 100 to 140°C for several is the space of a few hours, followed by calcination at high temperature for several hours.

Dehydration of 1-phenylethanol in styrene according to the present invention is carried out in the gas phase at elevated temperature. The term "elevated temperature" preferably means any temperature above 150°C. the Preferred conditions of dehydration, which should be applied, are conditions which are usually used, and include a reaction temperature from 210 to 330°C, more preferably from 280 to 320°C, most preferably about 300°C, and a pressure in the range from 0.1 to 10 bar, most preferably about 1 bar.

In the method according to the present invention it was found that the catalyst described above, has the reaction selectivity to styrene of at least 96% at a conversion of at least 99%, and at a conversion of 99% and above achieved at a selectivity of 97% or higher. In this regard, the reaction selectivity is defined as the number of moles of styrene formed per mole of the compounds of the precursor is transformed into products. Similarly, the selectivity for other compounds, such as heavy fraction, defined as the number of moles of compounds, precursors, turned into a heavy fraction, per mole of the compounds of the precursors are converted into products. Conversion is defined as the complete conversion of 1-phenylethanol, as defined in the test conditions, i.e. the molar percentage of unreacted 1-phenylethanol from p is LEGO the number of moles of 1-phenylethanol, present in the feed. In addition, the selectivity of the catalyst in heavy by-products such as oligomers and ethers, very low selectivity for the esters usually less than 0,8%, more preferably less than 0.3%, and the selectivity to oligomers typically less than 3% and preferably 2% or less.

Hereinafter the invention will be illustrated in the following examples, not limiting the scope of the invention these private options for implementation.

Example 1

The catalyst trendalicious form with the physical properties specified in table 1 (Ex-1)was tested on the characteristics of dehydration in the setting with micro currents, consisting of a reactor of ideal displacement with a diameter of 13 mm, installation evaporation 1-phenylethanone raw materials and the installation of condensing vapors of the product. As raw materials 1-phenylethanol used a sample of the process stream in the styrene reactor system serial setup propylene Oxide/styrene Monomer". Raw materials contained 81,2% 1-phenylethanol, 10.6 percent of methylvinylketone and 2% water. The remainder to 100% consisted of impurities and (by -) products of the preceding sections oxidation and epoxidation. Output setup with micro currents of oriali condensation, received a two-phase liquid system was analyzed using gas chromatography analysis.

The experimental is NT by dehydration was conducted under test conditions: pressure of 1.0 bar and a temperature of 300° C. the feed Rate 1-phenylethanol supported at the level of 30 grams per hour, the tube reactor was loaded 20 cm3of the catalyst. The reaction continued for approximately 140 hours, after which the experiment was stopped.

The catalyst activity (conversion) and selectivity for the reaction after 50 hours of operation were determined from gas chromatographic analysis of samples of the reaction products. We measured the activity after 120 hours. The data are shown in table 1. The activity and selectivity were defined above.

Example 2

Repeating the procedure described in example 1, except that used other raw materials containing 81.3% of 1-phenylethanol and 9.9% of methylvinylketone. The data are shown in table 1 (Ex-2).

Comparative example 1

Repeating the procedure described in example 1, except that the catalyst trendalicious form had a surface area according to BET 149 m2. Physical properties are listed in table 1 (Comp-Ex-1). The experiment was controlled by only the conversion of 1-phenylethanol, the experiment was terminated after 98 hours, when the conversion of 1-phenylethanol was 79%.

Comparative example 2

Repeating the procedure described in example 1, except that the used catalyst stellate form with physical properties in the range, which is described in the method according dock is the ment WO 99/58480. The reaction was continued for about 120 hours. Data on activity and selectivity are shown in table 1 (Comp-Ex-2).

Comparative example 3

Repeating the procedure described in example 1, except that used trendology catalyst physical properties within the range described in the method according to the document WO 99/58480. Used a sample of material containing 79,0% 1-phenylethanol and 10.0% of methylvinylketone. The data are shown in table 1 (Comp-Ex-3). The experiment was stopped after 113 hours, when the conversion of 1-phenylethanol was only 91%. Data on activity and selectivity are shown in table 1 (Comp-Ex-3).

Table 1< / br>
Properties and characteristics of the catalyst
Ex-1Ex-2Comp-Ex-1Comp-Ex-2Comp-Ex-3
Surface area (BET, m2/g)11011014910084
Pore volume (Hg, ml/g)0,770,770,840,570,44
Particle diameter (mm)2,52,52,53,62,5
Conversion (%) after 50 h99,999,9 98,099,799,9
The selectivity to styrene (%) after 50 h96,596,5(a)95,995,0
Selectivity for heavy fractions (ethers, + oligomers) (%) after 50 h3,03,0(a)3,54,3
Conversion (%) after 120 h99,799,8(b)97,3(c)
(a) is not defined

(b) the experiment is stopped after 98 hours, when the conversion was equal to 79%

(c) the experiment is stopped after 113 hours, when the conversion was equal to 91%

1. The method of producing styrene, including gas-phase dehydration of 1-phenylethanol at elevated temperature in the presence of a dehydration catalyst in which the catalyst for dehydration includes a molded catalyst particles on the basis of aluminum oxide with a surface area (BET) of from 80 to 140 m2/g and a pore volume (Hg) is more of 0.65 ml/year

2. The method according to claim 1, and pore volume (Hg) of the catalyst is from 0.75 to 0.85 ml/year

3. The method according to claim 1 and/or 2, and a catalyst based on alumina prepared from pseudoboehmite.



 

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