CN109251119A - A method of alkylbenzene is produced using supergravity reactor - Google Patents
A method of alkylbenzene is produced using supergravity reactor Download PDFInfo
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- CN109251119A CN109251119A CN201710576857.1A CN201710576857A CN109251119A CN 109251119 A CN109251119 A CN 109251119A CN 201710576857 A CN201710576857 A CN 201710576857A CN 109251119 A CN109251119 A CN 109251119A
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/88—Growth and elimination reactions
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- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
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- C07—ORGANIC CHEMISTRY
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- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
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Abstract
The present invention provides a kind of method using supergravity reactor production alkylbenzene.Benzene is alkylated in the supergravity reactor equipped with alkylation catalyst by this method with alkylating reagent to react, and separates to the product of alkylated reaction, obtains alkylbenzene.Method of the invention can be improved the selectivity and yield of target product, effectively inhibits the carbon distribution inactivation of alkylation catalyst, is conducive to the control of alkylated reaction temperature and the stable operation of alkylated reaction.
Description
Technical field
The present invention relates to a kind of methods for producing alkylbenzene, and in particular to a kind of to produce alkylbenzene using supergravity reactor
Method.
Background technique
Benzene is a kind of widely used chemical products, mainly from catalytic reforming, coal tar, ethylene process, with oil refining
Industrial and coal tar industry to flourish, there is surplus in the production capacity of benzene in the market, therefore develops the more valuable of benzene and utilize on the way
Diameter becomes imperative.Wherein, producing alkylbenzene by benzene alkylation reaction is an approach for realizing benzene effective use, alkyl
Benzene can be used as the raw material of Aromatic Hydrocarbon United Plant increasing yield of p-xylene, have significant economic benefit.
In recent years, the appearance of methanol production capacity is excessive on domestic market, and it is former that methanol becomes a kind of relatively inexpensive chemical industry
Material, therefore alkylbenzene is produced using the alkylated reaction of benzene and methanol.The alkylated reaction of benzene and methanol refers to methanol
For alkylating reagent, increase one or more methyl on phenyl ring, to generate the process of alkylbenzene.It is generally believed that the reaction
Carbonium ion reaction mechanism is followed, methanol activates at catalyst acid center first, forms methyl carbonium ion, and then send out with phenyl ring
Raw electrophilic substitution reaction generates toluene, and methyl carbonium ion continues to generate dimethylbenzene with toluene generation electrophilic substitution reaction, also
A small amount of ethylbenzene and more alkylaromatic hydrocarbons generate, while generating waste water.
Currently, generalling use the alkylated reaction that fixed-bed process carries out benzene.For example, Publication No. CN102101818A
Chinese patent discloses a kind of method for reacting production dimethylbenzene with methanol alkylation using fixed-bed process benzene；Publication No.
The Chinese patent of CN104109065A discloses a kind of using two fixed bed reactors progress benzene and methanol alkylation diformazan
The method of benzene.Above-mentioned fixed-bed process inevitably makes the reaction product from previous area undergo catalyst bed again
Layer increases the degree of side reaction generation, while aromatic hydrocarbons and height to extend reactant in the residence time of catalyst bed
The long-time contact of warm catalyst bed exacerbates the possibility of catalyst carbon deposition, is unfavorable for the long-period stable operation of device.
In addition, the product of abovementioned alkylization reaction is usually the mixture of alkylbenzene, it is difficult to obtain target with high selectivity
Product need to increase subsequent machining technology in order to which alkylbenzene mixture is processed as target product, be unfavorable for promoting and applying.
Summary of the invention
The present invention provides a kind of method using supergravity reactor production alkylbenzene, to the selectivity of target product
It is high.
The present invention provides a kind of method using supergravity reactor production alkylbenzene, and benzene and alkylating reagent are being equipped with
It is alkylated reaction in the supergravity reactor of alkylation catalyst, the product of alkylated reaction is separated, alkane is obtained
Base benzene.
In the present invention, supergravity reactor is for making the alkylated reaction of benzene and alkylating reagent under Elevated Gravity
(environment i.e. bigger than terrestrial gravitation acceleration g, terrestrial gravitation acceleration g=9.8m/s2) carry out.The present invention reacts hypergravity
The concrete type of device does not limit strictly, as long as it is horizontal to can be realized required hypergravity.
Specifically, alkylation catalyst can be fixed on the rotor of supergravity reactor, to form catalyst bed
Layer；In alkylation process, catalyst bed is rotated always with rotor with certain speed, thus overweight needed for being formed
Power is horizontal, to ensure that alkylated reaction carries out under Elevated Gravity.Wherein, hypergravity level refers to that supergravity reactor turns
Son rotates the size of generated centrifugal force；It can realize that different hypergravities is horizontal by controlling the revolving speed of rotor.
Method of the invention carries out the alkylated reaction of benzene and alkylating reagent, the hypergravity under Elevated Gravity
Environment can greatly strengthen mass transfer and micro mixing, mass transfer and microcosmic mixing than traditional static state (i.e. under gravitational field)
The mass tranfer coefficient and mixing velocity of process greatly improve；It can effectively reduce or eliminate diffusion process to the shadow of alkylated reaction
It rings, the product generated is enable to speed away reaction environment, be conducive to the selectivity and yield that improve target product, and effectively
The carbon distribution inactivation for inhibiting alkylation catalyst, promotes reactant to accelerate mobile to product direction, to improve reaction efficiency.This
Outside, the alkylated reaction of benzene is exothermic reaction, and in exothermal reaction process, it is most important to exclude reaction heat in time；The present invention exists
Reaction is alkylated in supergravity reactor, since product speeds away catalyst bed under the invigoration effect of hypergravity,
Exothermic heat of reaction is generated object and takes conversion zone, therefore easily controllable reaction temperature out of rapidly, is conducive to stable reaction operation.This hair
The problems such as alkylated reaction side reaction that bright method is able to solve the prior art is more, target product is selectively difficult to control, no
Only space-time yield is high, and target product selectivity is high.
In concrete scheme of the invention, the alkylated reaction is carried out under conditions of hypergravity level is 2-400g.
The present invention does not limit alkylating reagent strictly, such as can be methanol etc., and price is low, is conducive to improve warp
Ji benefit.
It is (1-10) it is possible to further control the molar ratio of the benzene and the alkylating reagent: 1；And it can control
The temperature for making the alkylated reaction is 400-500 DEG C, absolute pressure 0.1-5MPa, mass space velocity 3-30h-1。
The present invention does not limit alkylation catalyst strictly, can be the alkylation catalyst of this field routine；At this
In the concrete scheme of invention, the alkylation catalyst can be in ZSM-5 molecular sieve, MCM-56 molecular sieve and beta-molecular sieve
It is one or more.
Under the above conditions, or mixtures thereof toluene, dimethylbenzene can be generated in the alkylated reaction of benzene and methanol.
In particular, the present invention can by alkylation catalyst, hypergravity is horizontal, alkylated reaction selects, from
And toluene or dimethylbenzene are produced with high selectivity.
In one embodiment, the method property of can choose of the invention produces toluene.Specifically, the alkylbenzene is first
Benzene, and the alkylated reaction is carried out under conditions of hypergravity level is greater than 100g, alternative production toluene；Further
Ground, hypergravity level can be 200-400g.
Furthermore, it is possible to which the absolute pressure for controlling the alkylated reaction is 0.5-5MPa, mass space velocity 3-30h-1；It is described
Alkylation catalyst can be ZSM-5 molecular sieve, MCM-56 molecular sieve or beta-molecular sieve.
Under the above conditions, the selectivity of toluene is greater than 98%.
In another embodiment, being also an option that property of method of the invention produces dimethylbenzene.Specifically, the alkylbenzene
For dimethylbenzene, and the alkylated reaction is carried out under conditions of hypergravity level is 2-100g, alternative production diformazan
Benzene；Further, hypergravity level can be 200-400g.
Furthermore, it is possible to which the absolute pressure for controlling the alkylated reaction is 0.5-5MPa, mass space velocity 3-30h-1；It is described
Alkylation catalyst can be ZSM-5 molecular sieve or the mixture of ZSM-5 molecular sieve and MCM-56 molecular sieve.
Under the above conditions, the selectivity of dimethylbenzene is greater than 96%.
Further, the product of alkylated reaction is separated, isolates unreacted benzene and waste water, height can be obtained
The toluene or dimethylbenzene of purity, the complete benzene of unreacted, which is recycled into supergravity reactor, continues alkylated reaction.
Implementation of the invention, at least has the advantage that
1, method of the invention carries out the alkylated reaction of benzene and alkylating reagent, under Elevated Gravity to mention
The high selectivity and yield of target product, effectively inhibits the carbon distribution of alkylation catalyst to inactivate, is conducive to alkylated reaction
The control of temperature and the stable operation of alkylated reaction.
2, method of the invention be able to solve the prior art alkylated reaction side reaction is more, target product is selectively difficult to
It the problems such as control, can be by the selection to alkylation catalyst and alkylation reaction condition, to produce with high selectivity
Toluene or dimethylbenzene, wherein the selectivity of toluene is greater than 98%, and the selectivity of dimethylbenzene is greater than 96%.
Detailed description of the invention
Fig. 1 is the process flow chart that alkylbenzene is produced using supergravity reactor of an embodiment of the present invention；
Fig. 2 is the structural schematic diagram of the supergravity reactor of an embodiment of the present invention.
Description of symbols:
1: reaction raw materials entrance；2: alkylation catalyst bed layer；3: rotor；4: reacting product outlet.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with the embodiment of the present invention, to this
Technical solution in inventive embodiments is clearly and completely described, it is clear that described embodiment is that a part of the invention is real
Example is applied, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making creation
Property labour under the premise of every other embodiment obtained, shall fall within the protection scope of the present invention.
Embodiment 1
As shown in Fig. 2, MCM-56 molecular sieve catalyst is mounted in the rotor 3 of supergravity reactor, alkylation is formed
Catalyst bed 2；By the lasting rotation of rotor 3, drives alkylation catalyst bed layer 2 persistently to rotate, form the overweight of 200g
Power is horizontal.
As shown in connection with fig. 1, benzene and methanol are passed through in supergravity reactor with molar ratio 8:1 from reaction raw materials entrance 1, with
Alkylated reaction occurs for the contact of alkylation catalyst bed layer 2 persistently rotated；Wherein, the temperature for controlling alkylated reaction is 350
DEG C, absolute pressure 1.0MPa, mass space velocity 10h-1。
After alkylated reaction, product is discharged by the reacting product outlet 4 of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the toluene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 99.5% in alkylate, and the selectivity of dimethylbenzene is 0.5%；Raw material
The conversion ratio of benzene is 12.4%.
In addition, longtime running the result shows that, the alkylation catalyst bed layer 2 in above-mentioned supergravity reactor is not easy carbon distribution,
Supergravity reactor being capable of long-period stable operation.
Embodiment 2
ZSM-5 molecular sieve catalyst is mounted in the rotor of supergravity reactor, alkylation catalyst bed layer is formed；It is logical
The lasting rotation of rotor is crossed, alkylation catalyst bed layer is driven persistently to rotate, the hypergravity for forming 300g is horizontal.
Benzene and methanol are passed through in supergravity reactor with molar ratio 4:1, the alkylation catalyst bed layer with lasting rotation
Alkylated reaction occurs for contact；Wherein, the temperature for controlling alkylated reaction is 470 DEG C, absolute pressure 0.5MPa, mass space velocity
For 15h-1。
After alkylated reaction, product is discharged by the reacting product outlet of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the toluene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 98.2% in alkylate, and the selectivity of dimethylbenzene is 1.8%；Raw material
The conversion ratio of benzene is 24.0%.
Embodiment 3
Beta-molecular sieve catalyst is mounted in the rotor of supergravity reactor, alkylation catalyst bed layer is formed；By turning
The lasting rotation of son drives alkylation catalyst bed layer persistently to rotate, and the hypergravity for forming 400g is horizontal.
Benzene and methanol are passed through in supergravity reactor with molar ratio 2:1, the alkylation catalyst bed layer with lasting rotation
Alkylated reaction occurs for contact；Wherein, the temperature for controlling alkylated reaction is 450 DEG C, absolute pressure 2.5MPa, mass space velocity
For 20h-1。
After alkylated reaction, product is discharged by the reacting product outlet of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the toluene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 98.0% in alkylate, and the selectivity of dimethylbenzene is 2.0%；Raw material
The conversion ratio of benzene is 42.5%.
Embodiment 4
ZSM-5 molecular sieve catalyst is mounted in the rotor of supergravity reactor, alkylation catalyst bed layer is formed；It is logical
The lasting rotation of rotor is crossed, alkylation catalyst bed layer is driven persistently to rotate, the hypergravity for forming 10g is horizontal.
Benzene and methanol are passed through in supergravity reactor with molar ratio 4:1, the alkylation catalyst bed layer with lasting rotation
Alkylated reaction occurs for contact；Wherein, the temperature for controlling alkylated reaction is 390 DEG C, absolute pressure 1.0MPa, mass space velocity
For 20h-1。
After alkylated reaction, product is discharged by the reacting product outlet of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the dimethylbenzene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 0.6% in alkylate, and the selectivity of dimethylbenzene is 99.4%；Raw material
The conversion ratio of benzene is 12.3%.
In addition, longtime running the result shows that, the alkylation catalyst bed layer 2 in above-mentioned supergravity reactor is not easy carbon distribution,
Supergravity reactor being capable of long-period stable operation.
Embodiment 5
The mixed catalyst being made of ZSM-5 molecular sieve and MCM-56 molecular sieve is mounted on to the rotor of supergravity reactor
In, alkylation catalyst bed layer is formed, the mass ratio of ZSM-5 molecular sieve and MCM-56 molecular sieve is 50:50 in mixed catalyst；
By the lasting rotation of rotor, alkylation catalyst bed layer is driven persistently to rotate, the hypergravity for forming 50g is horizontal.
Benzene and methanol are passed through in supergravity reactor with molar ratio 2:1, the alkylation catalyst bed layer with lasting rotation
Alkylated reaction occurs for contact；Wherein, the temperature for controlling alkylated reaction is 470 DEG C, absolute pressure 0.5MPa, mass space velocity
For 15h-1。
After alkylated reaction, product is discharged by the reacting product outlet of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the dimethylbenzene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 0.5% in alkylate, and the selectivity of dimethylbenzene is 99.5%；Raw material
The conversion ratio of benzene is 24.6%.
Embodiment 6
ZSM-5 molecular sieve catalyst is mounted in the rotor of supergravity reactor, alkylation catalyst bed layer is formed；It is logical
The lasting rotation of rotor is crossed, alkylation catalyst bed layer is driven persistently to rotate, the hypergravity for forming 100g is horizontal.
Benzene and methanol are passed through in supergravity reactor with molar ratio 1:1, the alkylation catalyst bed layer with lasting rotation
Alkylated reaction occurs for contact；Wherein, the temperature for controlling alkylated reaction is 420 DEG C, absolute pressure 3.0MPa, mass space velocity
For 10h-1。
After alkylated reaction, product is discharged by the reacting product outlet of supergravity reactor, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
Condensed product can then enter benzene column and be separated, and isolated benzene, which is recycled into supergravity reactor, to be continued
It is alkylated reaction；Isolated product, which can enter in oil water separator, to be removed water, and the dimethylbenzene of high-purity can be obtained.
The result shows that: the selectivity of toluene is 3.2% in alkylate, and the selectivity of dimethylbenzene is 96.8%；Raw material
The conversion ratio of benzene is 41.6%.
Reference examples 1
MCM-56 molecular sieve catalyst is filled in fixed bed reactors, alkylation catalyst bed layer is formed.
Benzene and methanol are passed through in fixed bed reactors with molar ratio 8:1, is contacted with alkylation catalyst bed layer and alkane occurs
Glycosylation reaction；Wherein, the temperature for controlling alkylated reaction is 350 DEG C, absolute pressure 1.0MPa, mass space velocity 10h-1。
After alkylated reaction, product is discharged by the reacting product outlet of fixed bed reactors, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
The result shows that: the selectivity of toluene is 46.5% in alkylate, and the selectivity of dimethylbenzene is 39.6%；Raw material
The conversion ratio of benzene is 10.2%.Thus illustrate, the alkylated reaction of benzene and methanol is carried out using fixed bed reactors, not only easily increase
Add the generation of side reaction, furthermore can not obtain target product toluene with high selectivity.
In addition, above-mentioned fixed bed reactors are after running for a period of time, alkylation catalyst bed layer carbon deposition phenomenon is more tight
Weight, and the temperature of alkylated reaction is not easy to control, to be unfavorable for the long-period stable operation of reactor.
Reference examples 2
By ZSM-5 molecular sieve catalyst filling in fixed bed reactors, alkylation catalyst bed layer is formed.
Benzene and methanol are passed through in fixed bed reactors with molar ratio 4:1, is contacted with alkylation catalyst bed layer and alkane occurs
Glycosylation reaction；Wherein, the temperature for controlling alkylated reaction is 390 DEG C, absolute pressure 1.0MPa, mass space velocity 20h-1。
After alkylated reaction, product is discharged by the reacting product outlet of fixed bed reactors, subsequently enters heat exchanger
It is condensed, the composition of collecting and sampling and use gas chromatographic analysis measurement alkylate after condensation.
The result shows that: the selectivity of toluene is 47.8% in alkylate, and the selectivity of dimethylbenzene is 36.8%；Raw material
The conversion ratio of benzene is 14.8%.Thus illustrate, the alkylated reaction of benzene and methanol is carried out using fixed bed reactors, not only easily increase
Add the generation of side reaction, furthermore can not obtain target product dimethylbenzene with high selectivity.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
So be possible to modify the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (10)
1. a kind of method using supergravity reactor production alkylbenzene, which is characterized in that benzene and alkylating reagent to be equipped with
It is alkylated reaction in the supergravity reactor of alkylation catalyst, the product of alkylated reaction is separated, alkane is obtained
Base benzene.
2. the method according to claim 1, wherein described in being carried out under conditions of hypergravity level is 2-400g
Alkylated reaction.
3. the method according to claim 1, wherein the molar ratio for controlling the benzene and the alkylating reagent is
(1-10):1；And the temperature for controlling the alkylated reaction is 400-500 DEG C, absolute pressure 0.1-5MPa, mass space velocity
For 3-30h-1。
4. the method according to claim 1, wherein the alkylation catalyst is selected from ZSM-5 molecular sieve, MCM-
One of 56 molecular sieves and beta-molecular sieve are a variety of.
5. method according to any one of claims 1 to 4, which is characterized in that the alkylbenzene is toluene, and in hypergravity
Level carries out the alkylated reaction under conditions of being greater than 100g.
6. according to the method described in claim 5, it is characterized in that, the absolute pressure for controlling the alkylated reaction is 0.5-
5MPa, mass space velocity 3-30h-1。
7. according to the method described in claim 5, it is characterized in that, the alkylation catalyst is ZSM-5 molecular sieve, MCM-56
Molecular sieve or beta-molecular sieve.
8. method according to any one of claims 1 to 4, which is characterized in that the alkylbenzene is dimethylbenzene, and overweight
Power level carries out the alkylated reaction under conditions of being 2-100g.
9. according to the method described in claim 8, it is characterized in that, the absolute pressure for controlling the alkylated reaction is 0.5-
5MPa, mass space velocity 3-30h-1。
10. according to the method described in claim 8, it is characterized in that, the alkylation catalyst be ZSM-5 molecular sieve or
The mixture of ZSM-5 molecular sieve and MCM-56 molecular sieve.
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