Method of production of styrene

FIELD: petrochemical industry; methods of production of styrene.

SUBSTANCE: the invention is pertaining to the field of petrochemical industry, in particular, to the method of production of styrene. The invention provides for dehydrogenation of the ethylbenzene charge gained after mixing of the fresh ethylbenzene with the recycled ethylbenzene on the ferrioxide catalytic agent at presence of the steam at the mass ratio of the raw to the steam of no less than 1:2, at the temperature of 580-640°С and the volumetric speed of feeding of the ethylbenzene charge of 0.23-0.45 m3/h. The hydrocarbon condensate (the product of the dehydrogenation) containing styrene, the unreacted ethylbenzene, the by-products including the phenyl acetylene impurity before the stage of the rectification is hydrogenated using the palladium-containing catalytic agents at the temperature of 20-30°С, the volumetric speed of 4.5-5.0 m3/h-1 and at the volumetric ratio of the hydrogen : raw - 35-45. The technical result of the invention is the increased purity of the produced styrene without reduction of productivity of the whole process of the marketable styrene.

EFFECT: the invention ensures the increased purity of the produced styrene without reduction of productivity of the whole process of the marketable styrene.

1 tbl, 8 ex

 

The invention relates to the field of catalytic processes, namely the obtaining of styrene by catalytic dehydrogenation of ethylbenzene, and can be used in the petrochemical industry.

Known methods for producing styrene by catalytic dehydrogenation of ethylbenzene on micaceous iron catalysts at temperatures 560-640°in the presence of water vapor, followed by separation of styrene from the products of dehydrogenation of ethylbenzene by multistage distillation with sequential allocation benzatropine faction, return ethylbenzene and styrene-rectified. CBM product of the column selection styrene-rectified subjected to additional distillation with return of distilled styrene in the column selection styrene-rectified (Kirpichnikov P.A. and other "Album of technological schemes of the main production of the synthetic rubber industry", HP, "Chemistry", 1980, p.100; Oil, gas and petrochemicals abroad, 1991, 8, p.100-102; U.S. Patent No. 3326996, CL 260-669, 1967; Amiwin and other "styrene", M, Tsniiteneftehim, 1996, ñ.38).

The well-known "Method of producing styrene (Patent RF №2120933, class C 07 C 15/46, 1998), whereby obtaining a styrene-based process for the catalytic dehydrogenation of ethylbenzene in the environment of water vapor, where acibenzolar the mixture obtained after mixing of the fresh and return (retic is a) ethylbenzene, styrene content in the mixture at no more than about 0.15 wt.% subjected to dehydrogenation at micaceous iron catalyst. The process is carried out at a temperature of 600-640°C, the mass ratio of raw materials:water vapor equal to 1:2, and a space velocity of etilbenzene charge 1 hour-1. The conversion of ethylbenzene is to 67.9 wt.% when the selectivity of the conversion of ethylbenzene to styrene 96,7%.

Simultaneously with the main reaction is the conversion of ethylbenzene to styrene

by free-radical mechanism under the action of high temperatures is formed from styrene - product phenylacetylene

which adversely affects the quality of commercial styrene.

In accordance with GOST 10003-90 trademark mixture of styrene phenylacetylene (wt.%) in the styrene is highly regulated:

top gradenot more than 0.01
I sortnot more than 0.02

A disadvantage of the known methods of obtaining styrene is a high content of impurities phenylacetylene in the styrene-rectified (commodity styrene), which is often not possible to produce it with quality indicators corresponding to the highest grade, and therefore, it is not possible to export this product.

The most effective is m to the technical essence and the achieved result of the present invention is a method of producing styrene by catalytic dehydrogenation of ethylbenzene (technological regulations styrene production shop №46 JSC "Salavatnefteorgsintez" prototype, see the electronic version of the source you specified in the Annex to the present description).

According to the prototype of the main industrial method of producing styrene is the catalytic dehydrogenation of ethylbenzene. Process for the catalytic dehydrogenation of ethylbenzene to styrene is carried out in the adiabatic reactors filled with micaceous iron catalyst, in the presence of water vapor in the reaction equation

The possible limits of the process of dehydrogenation:

temperature, °580-640
volumetric speed feed
etilbenzene charge, h-10,23-0,45
pressure (abs.), kgf/cm2of 0.45 to 0.75
the mass ratio etilbenzene
mixture and water vapor of not less than1:2

In addition to the main reaction dehydrogenation occurring adverse reactions. Adverse reactions occur as part of the raw materials and compounds produced in the dehydrogenation process, and the impurities contained in raw materials.

Under the influence of high temperature non-catalytic zones by free-radical mechanism, the formation of the following major impurities, which affect the quality of commercial styrene:

Hydrocarbon condensate (product of dehydrogenation)containing styrene, unreacted ethylbenzene, by-products, including mixed phenylacetylene and water vapor, is subjected to multi-stage distillation for separation of styrene-rectified, return ethylbenzene, benzatropine fraction and a bottoms distillation of styrene. The concentration of the basic substance (styrene) styrene-rectified at least 99.8 wt.%. The concentration of impurities phenylacetylene in the styrene-rectified - not more than 0.01 wt.% (the highest grade).

The disadvantage of this method is the high content of impurities phenylacetylene in the styrene-rectified (commodity styrene), which is a catalytic poison in the process of obtaining polystyrene and the contents of which commodity styrene is highly regulated (higher grade GOST 10003-90).

The aim of the proposed izobreteniya improving the efficiency of the production of styrene by the catalytic dehydrogenation of ethylbenzene by improving the quality of styrene-rectified (commodity styrene) by reducing the content of impurities phenylacetylene.

This goal is achieved by the proposed method to obtain styrene, which is carried out by catalytic dehydrogenation of ethylbenzene in the presence of water vapor, followed by distillation of the hydrocarbon condensate to highlight styrene-rectified (commodity styrene), return ethylbenzene, benzatropine fraction and a bottoms distillation of styrene by introducing a new stage of the process - before the stage of distillation of the hydrocarbon condensate previously subjected to catalytic hydrogenation. The hydrogenation process is carried out on palladium catalysts at a temperature of 20-30°C, flow rate of feed of 4.5-5.0 h-1and a volume ratio of hydrogen:feedstock equal 35-45.

Comparative analysis of the proposed method with the prototype allows to conclude that the claimed method differs from the known switching in the process of obtaining styrene, at the stage of rectification, the new stage - stage hydrogenation of hydrocarbon condensate. The hydrogenation is carried out on palladium catalysts at a temperature of 20-30°C, flow rate of feed of 4.5-5.0 h-1and a volume ratio of hydrogen:feedstock equal 35-45. These techniques allow to conclude that the proposed solution meets the criterion of "novelty".

Analysis of izvestnyh ways to obtain styrene showed what stage hydrogenation of hydrocarbon condensate product stage dehydrogenation of etilbenzene mixture in the process of obtaining styrene was not previously known. Accordingly, not previously considered the catalysts and the conditions necessary for carrying out this stage. However, only the inclusion of this stage in the process of obtaining styrene ensures styrene-rectified (trade styrene) content of impurities phenylacetylene less than 0.01 wt.%.

The essence of the invention consists in the following. Acibenzolar the mixture obtained by the mixing of fresh ethylbenzene and benzene recycle, is subjected to dehydrogenation at micaceous iron catalyst in the presence of water vapor in the reaction equation

The possible limits of the process of dehydrogenation:

temperature, °580-640
volumetric speed feed
etilbenzene charge, h-10,23-0,45
pressure (abs.), kgf/cm2of 0.45 to 0.75
the mass ratio etilbenzene
mixture and water vapor of not less than1:2

Under the influence of high temperatures on the freedoms of the Oh-radical mechanism, the formation of impurities phenylacetylene, which adversely affects the quality of commercial styrene

Hydrocarbon condensate (product of dehydrogenation)containing styrene, unreacted ethylbenzene, by-products, including mixed phenylacetylene, is subjected to catalytic hydrogenation on palladium catalysts G-58E or swtc at a temperature of 20-30°C, flow rate of feed of 4.5-5.0 h-1and a volume ratio of hydrogen:feedstock equal 35-45.

The hydrogenation catalyst G-58E - granules (extrudates), the palladium content 0,039 wt.%, silver 0.25 wt.%. The catalytic hydrogenation STUCK - fiberglass woven catalyst in the form of a grid (cell size 2-2 .5 mm, the thread diameter 1 mm); the palladium content of 0.2 wt.%.

The hydrogenation takes place in the reaction equation

Simultaneous hydrogenation parts of styrene contained in the hydrocarbon condensate in the reaction equation

Hydrogenation of hydrocarbon condensate, although significantly improves the quality of commercial styrene, but due to hydrogenation parts of styrene in ethylbenzene reduces the performance of the whole process trademark styrene. So made the selection of the catalyst and the process conditions of the hydrogenation of hydrocarbon condensate was sent to Kennon selective hydrogenation of phenylacetylene and minimizing hydrogenation of styrene.

The hydrogenation product containing styrene, unreacted ethylbenzene and by-products, is subjected to multi-stage distillation to obtain a styrene-rectified with the concentration of the basic substance (styrene) at least 99.8 wt.% and impurities phenylacetylene less than 0.01 wt.%, return ethylbenzene, benzatropine fraction and a bottoms distillation of styrene. Return ethylbenzene-recycling mixed with fresh ethylbenzene, and received acibenzolar the mixture is again fed to the dehydrogenation unit.

Example 1 (prototype). Acibenzolar the mixture obtained by the mixing of fresh ethylbenzene and benzene recycle, is subjected to dehydrogenation at micaceous iron catalyst in the presence of steam at a mass ratio of raw materials:water vapour 1:2, the temperature of 600°C, the pressure of 0.45 kgf/cm2(abs.) and a space velocity of etilbenzene mixture of 0.25 h-1. Hydrocarbon condensate (product of dehydrogenation)containing styrene, unreacted ethylbenzene, by-products, including mixed phenylacetylene, and water vapor, is subjected to multi-stage distillation for separation of styrene-rectified, return ethylbenzene, benzatropine fraction and a bottoms distillation of styrene. The concentration (content) of impurities phenylacetylene in the styrene-rectified 0,0123 wt.%.

Example 2. Ethylbenzol what I charge, obtained by blending fresh ethylbenzene and benzene recycle, is subjected to dehydrogenation at micaceous iron catalyst in the presence of steam at a mass ratio of raw materials:water vapour 1:2, the temperature of 600°C, the pressure of 0.45 kgf/cm2(abs.) and a space velocity of etilbenzene mixture of 0.25 h-1. Hydrocarbon condensate (product of dehydrogenation)containing styrene, unreacted ethylbenzene, by-products, including mixed phenylacetylene, and water vapor, at the stage of rectification previously subjected to catalytic hydrogenation on palladium catalyst G-58E at a temperature of 20°C, flow rate of feed of 4.5 h-1and a volume ratio of hydrogen:the raw material is equal to about 45./about. The hydrogenation product is fed to the distillation as in example 1. The degree of transformation of phenylacetylene contained in the hydrocarbon condensate, styrene is 32.8 wt.% and is calculated by the formula

where Cf0content phenylacetylene in raw materials (wt.%);

Withf1content phenylacetylene in the hydrogenation product (wt.%).

The degree of reaction (hydrogenation) of styrene in ethylbenzene was 4.0% and is calculated by the formula

where Carticle0content phenylacetic the s in raw materials (wt.%);

Witharticle1content phenylacetylene in the hydrogenation product (wt.%).

The concentration of phenylacetylene in the styrene-rectified 0,0085 wt.%.

The data of the other samples shown in the table.

Example 4 (comparative) shows that with increasing temperature hydrogenation of hydrocarbon condensate increases the degree of phenylacetylene hydrogenation and styrene to ethylbenzene), which reduces the performance of the whole process trademark styrene.

Lowering the temperature of the hydrogenation below 20°requires forced tahaliyani hydrocarbon condensate that is not economically profitable.

Example 5 (comparative) shows that with increasing space velocity of the feedstock is more deep hydrogenation of styrene to ethylbenzene, which reduces the performance of the whole process trademark styrene. To reduce the volumetric rate of less than 4.5 h-1it is not possible technologically.

Example 6 (comparative) shows that at high volume ratios of hydrogen:feedstock is deep hydrogenation of all unsaturated hydrocarbons, as phenylacetylene and styrene to ethylbenzene, which reduces the performance of the whole process trademark styrene. Reducing the volume ratio of hydrogen:the raw material is less than 35 is not technologically possible.

In examples 7, 8 the process of hydrogenation pleva Oronogo condensate carried out in the selected conditions, the palladium catalyst swtc. When it reached deep selective hydrogenation of phenylacetylene with minimal performance degradation of the whole process trademark styrene.

Table

The influence of process conditions for the hydrogenation of hydrocarbon condensate content phenylacetylene in the commodity situation.
IndicesExamples
1 prototype234 comparative
The conditions of hydrogenation
Temperature, °no203040
The volumetric ratio of N2/raw/about454545
The volumetric feed rate, h-14,54,54,5
Name catalystG-58EG-58EG-58E
Hydrocarbon composition, wt.%Hydrocarbon condensateThe hydrogenation product of the hydrocarbon condensate
waxes0,00140,00120,0030,0039
benzene0,42 0,380,380,38
toluene1,691,651,661,61
ethylbenzene44,6947,0147,4748,57
meta-xylene0,480,340,340,32
isopropylbenzene0,0170,0180,0190,021
ortho-xylene0,0090,00910,00910,009
para-xylene0,0270,0270,0280,29
atitool-0,00450,00420,0045
styrene52,5250,4150,0348,9
α-methylsterol0,1060.104 g0,1050.104 g
phenylacetylene0,00640,00430,00440,0049
benzaldehyde0,00320,00220,0020,0026
the divinylbenzene0,00110,00160,00160,0018
the degree of transformation of phenylacetylene in styrene, %no32,831,2523,4
the degree of conversion of styrene to ethylbenzene, %no4,0the 4.76,9
the content of phenylacetylene in commodity raw materials, wt.%0,01230,00850,00870,01

0,36
Continuation of the table.
IndicesExamples
5 comparative6 comparative78
The conditions of hydrogenation
Temperature, °30202030
The volumetric ratio of N2/raw/about45604035
The volumetric feed rate, h-164,54,55
Name catalystG-58EG-58ESTKSTK
Hydrocarbon composition, wt.%The hydrogenation product of the hydrocarbon condensate
waxes0,00380,00340,0190,0013
benzene0,360,260,35
toluene1,741,471,771,81
ethylbenzene49,6356,7945,6246,27
meta-xylene0,330,310,390,36
isopropylbenzene0,020,0290,0160,016
ortho-xylene0,00930,0090,00980,0093
para-xylene0,0260,030,0250,025
atitool0,00530,00520,00450,0047
styrene47,7340,9451,6551
α-methylsterol0,0970,0990,10,099
phenylacetylene0,00460,00350,000150,0005
benzaldehyde0,00180,0020,00350,0041
the divinylbenzene0,00140,00350,00150,0015
the degree of transformation of phenylacetylene in styrene, %28,145,397,792,2
the extent ol the rotation of styrene, wt.%7,7322,050,151,4
the content of phenylacetylene in commodity raw materials, wt.%0,00960,00860,000290,00098

The method of producing styrene by catalytic dehydrogenation of ethylbenzene in the presence of water vapor, followed by distillation of the hydrocarbon condensate to highlight styrene-rectified, return ethylbenzene, benzatropine fraction and a bottoms distillation of styrene, characterized in that at the stage of distillation of the hydrocarbon condensate previously subjected to catalytic hydrogenation on palladium catalysts at a temperature of 20-30°C, flow rate of 4.5-5.0 h-1and a volume ratio of hydrogen:feedstock equal 35-45.



 

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12 cl, 2 tbl

FIELD: hydrogenation-dehydrogenation catalysts.

SUBSTANCE: invention provides catalytic composition for dehydration of alkylaromatic hydrocarbons optionally combined with ethane comprising: carrier consisting of alumina in δ phase or in θ phase, or in mixed δ+θ or θ+α, or δ+θ+α phase, modified with silicon oxide and having surface area less than 150 m2/g as measured by BET method; 0.1-35% gallium in the form of Ca2O3; 0.01-5% manganese in the form of Mn2O3; 0-100 ppm platinum; and 0.05-4% alkali or alkali-earth metal oxide, all percentages being based on the total weight of composition. Other variants of composition are also covered by invention. Methods of preparing such catalytic composition (options) envisage use of alumina-based carrier in the form of particles corresponding to group A of the Geldart Classification. Process of dehydration of alkylaromatic hydrocarbons optionally combined with ethane comprises: (i) dehydration of hydrocarbon stream optionally mixed with inert gas in fluidized-bed reactor in presence of catalytic composition consisted of alumina-supported and silica-modified gallium and manganese at temperature within a range of 400 to 700°C, total pressure within a range of 0.1 to 3 atmospheres, and gas hourly space velocity from 50 to 10000 h-1; and (ii) regeneration and heating of catalyst caused by catalytic oxidation of fuel in fluidized-bed reactor at temperature above 400°C.

EFFECT: increased activity of catalytic composition and prolonged lifetime thereof.

22 cl, 2 tbl, 16 ex

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