CN103664488B - Remove the aromatic hydrocarbons methanol alkylation method of oxygenatedchemicals impurity - Google Patents
Remove the aromatic hydrocarbons methanol alkylation method of oxygenatedchemicals impurity Download PDFInfo
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Abstract
The present invention relates to a kind of aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity, mainly solve in conventional art and there is in aromatic hydrocarbon product the problem that there is oxygenatedchemicals impurity.The present invention is comprised the following steps by employing: a) benzene or toluene, methanol mixed raw material are by composite bed reactor, contacts with composite catalyst, generation stream I; B) stream I through heat exchange and cooling after enter water-and-oil separator, lower floor's byproduct water is disposed to out-of-bounds, upper oil phase overflow to downstream, as stream I I; C) stream I I enters stripping tower, light constituent drains into out-of-bounds by tower top, heavy constituent is as stream I II, be incorporated in Aromatic Hydrocarbon United Plant, isolate the technical scheme of p-Xylol, solve this problem preferably, the alkylated reaction that can be used for the aromatic hydrocarbons such as benzene or toluene and methyl alcohol is produced in the industrial production of xylol or p-Xylol.
Description
Technical field
The present invention relates to a kind of aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity, particularly about a kind of can by the method for by-product alcohols, aldehydes, ketone and the carboxylic-acid impurity removal in benzene or toluene and methyl alcohol methylation reaction product.
Background technology
P-Xylol is very important petrochemical complex basic organic, all has purposes extremely widely in fields such as trevira, medicine, agricultural chemicals, dye well solvents.At present, the PX throughput in the whole world is more than 3,000 ten thousand tons/year, and production capacity is still maintaining sustained and rapid growth, expecting 2011 yearly capacities will more than 4,000 ten thousand ton, wherein the throughput in Asia and consumers demand occupy the first in the world, 2011, Asia estimated to reach nearly 2,400 ten thousand tons to the demand of PX.And conduct most important p-Xylol Production and consumption state in the world of China, will reach 9,920,000 tons to 2011 annual requirements, production capacity then will reach more than 8,800,000 tons.
The most sufficient with the source of toluene in industry triphen, but its industrial use can not show a candle to dimethylbenzene, therefore causes toluene relative surplus; In recent years, domestic Chemical Industry is fast-developing, and Aromatic Hydrocarbon in Gasoline content's index constantly reduces, and superfluous trend has also appearred in benzaldehyde product; And p-Xylol all has purposes extremely widely in fields such as trevira, medicine, agricultural chemicals, dye well solvents, but this product only accounts for 4.2% in pyrolysis gasoline, is 7.5%, C in reformate
8be 22-26% in BTX aromatics, output wretched insufficiency.Therefore, toluene and benzene are changed into greatest extent the market requirement vigorous, the p-Xylol of high added value is an important research direction in petrochemical technology always.
Be dimethylbenzene by toluene conversion, then be this process of p-Xylol by dimethylbenzene by being separated with isomerization conversion, be the main method that p-Xylol is produced always.Be wherein the traditional method of dimethylbenzene by toluene conversion being toluene disproportionation process, developing into toluene disproportionation and heavy aromatics alkyl transfering process to effectively utilize carbon more than nine Heavy Aromatic Hydrocarbons.At present, the disproportionation processes of pure toluene charging has all been abandoned by nearly all producer, and replaces the alkyl transfering process that can process heavy aromatics.Realize industrialized toluene dimethylbenzene technique in recent years, also has selective disproportionation of toluene technique, the advantage of this technology is to produce the xylene product being rich in p-Xylol, therefore significantly reduce energy consumption and the material consumption of separation and isomerization process, be applicable to the enterprise that toluene resource is sufficient and heavy aromatics processing pressure is relatively low.Compared with above-mentioned two kinds of toluene dimethylbenzene processes, toluene or benzene and methanol alkylation are the p-Xylol new process of production that economic benefit is larger, can improve toluene or benzene utilization ratio substantially.And the methylating reagent methyl alcohol used is important Coal Chemical Industry product, and this technology is to the great significance of domestic Chemical Industry in future.
Methylbenzene methanol methylation reaction (MTX) refers to methyl alcohol to be raw material for alkylation, and toluene aromatic ring increases a methyl, thus generates the process of dimethylbenzene.Phenylcarbinol methylation reaction (BTX) refers to methyl alcohol to be raw material for alkylation, and the aromatic ring of benzene increases a methyl, thus generates the process of toluene and dimethylbenzene.MTX reaction is a St reaction in benzene undertaken by carbonium ion mechanism, process is: methyl alcohol is activated in catalyst B acid site, with the toluene of methyl carbonium ion attack weakly stable, due to the inducing action of methyl on phenyl ring, main generation o-Xylol and p-Xylol, less m-xylene, produces another product water simultaneously.BTX reaction is also the St reaction in benzene undertaken by carbonium ion mechanism, and target product is toluene and dimethylbenzene.Meanwhile, due to the introducing of methyl alcohol, also can there is the side reactions such as carbonylation, Olefination and etherificate in methyl alcohol self.
The methylation techniques feature of domestic Dalian Inst of Chemicophysics, Chinese Academy of Sciences is to produce low-carbon alkene by methyl alcohol side reaction richness while production dimethylbenzene, patent CN1721378 and CN101417233 describes the fluidized-bed of co-producing light olefins and the technique of moving-bed and catalyzer, and the problem for catalyzer shape selectivity loss in reaction process also proposed the modified technique that the online silicon of reaction is modified.
External each large petrochemical enterprise, as GTC company of the U.S., ExxonMobil company, Saudi Aribian Basic Industry Company, British Petroleum Company p.l.c. etc. have carried out large quantifier elimination to toluene methylation technology.The research work coverage of ExxonMobil company in toluene methylation is the widest, enumerates catalyzer and reaction process.In catalyzer, the said firm adopts high silica ZSM-5 molecular sieve as active main body in its patent CN97198340, then through P Modification, and by high-temperature water vapor process, catalyzer shape selectivity is significantly improved, in dimethylbenzene, Selectivity for paraxylene is more than 90%, and now toluene conversion is about 30%, and use ratio of methanol is 60%; Its another section of patent US5563310 then adopts the modification of IVB family metal oxide to obtain high activated catalyst, the generation Mixed XYLENE that methylates is carried out under toluene and methanol mol ratio is 4-8/1 and 200-235 DEG C of cold condition, toluene conversion is up to 11.8%, and dimethylbenzene yield is up to 9.7%.Process aspect the said firm has carried out multiple trial, relates to fluidized-bed process, reaction distillation technique and adopts synthetic gas and toluene to be the recombining process of raw material.
The catalyst technology of Saudi Aribian Basic Industry Company (SABIC), also based on ZSM-5 molecular sieve, adopts P Modification, and thinks that this catalyzer is also able to take aqueous reaction technique and dealuminzation hardly without steam-treated.Its patent CN200410068466 also describes the driving technique of its uniqueness, i.e. the process of high-speed, low hydrogen hydrocarbon when progressively temperature raising, and claims that catalyst stability is more than 500 hours.
But there is multiple reaction in methanol feedstock, also can bring a series of problem under the high temperature conditions with after catalyst exposure.From aromatic hydrocarbon product quality control, the carboxylic-acid impurity such as the ketones such as the aldehydes such as methyl alcohol and by-product acetaldehyde, by-product acetone, by-product acetic acid are dissolved in liquid phase aromatic product, threaten the normal running of the adsorption separation unit in the Aromatic Hydrocarbon United Plant of downstream, disproportionation unit and isomerization unit.
Summary of the invention
Technical problem to be solved by this invention is the problem containing oxygenatedchemicals impurity in aromatic hydrocarbon product, provides a kind of aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity newly.The method is used for toluene or phenylcarbinol methylates in industrial production, has aromatic hydrocarbon product quality not by the advantage of oxygenatedchemicals impurity effect.
In order to solve the problems of the technologies described above, the technical solution used in the present invention comprises the following steps: a kind of aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity, comprises the following steps:
A) it is 0.5 ~ 5 hour at temperature 350 DEG C ~ 480 DEG C, weight space velocity
-1, pressure is under 0.1 ~ 3MPa condition, benzene or toluene and methanol mixed raw material, by composite bed reactor, contact with composite catalyst, resultant of reaction stream I;
B) stream I through heat exchange and cooling after enter water-and-oil separator, the lower floor's by-product aqueous phase after separation is disposed to out-of-bounds, upper oil phase overflow to downstream, as stream I I;
C) stream I I enters stripping tower, the C of separation
6light constituent drained into out-of-bounds by tower top in the past, the C that tower reactor obtains
6and later heavy constituent, as stream I II, be incorporated in Aromatic Hydrocarbon United Plant, isolate p-Xylol;
Wherein, composite catalyst is methylation catalyst and oxygenatedchemicals Removal of catalyst.
In technique scheme, containing alcohols, ketone, aldehydes and carboxylic-acid oxygenatedchemicals in stream I, the weight content of the alcohols in stream I II, ketone, aldehydes and carboxylic-acid oxygenatedchemicals is all less than 0.5ppm; The weight content of the ketone in stream I I and carboxylic-acid oxygenatedchemicals is all less than 0.5ppm; The tower top temperature of stripping tower is 110 ~ 130 DEG C, and tower top pressure is 0.4 ~ 0.6MPa.
Preferred technical scheme, in step c), the C of separation
6light constituent was C in the past
1~ C
5alkane, alkene, and the oxygenatedchemicals such as acetaldehyde, methyl alcohol, in step c), the C that tower reactor obtains
6and heavy constituent comprises C later
6~ C
14aromatic hydrocarbons, alkane and alkene.Methylation catalyst is: at least one of (a) 40% ~ 90% in ZSM-5 zeolite or MCM-22 zeolite molecular sieve; MgO, La of (b) 0.01 ~ 5.0%
2o
3, CaO and SiO
2in at least one; The binding agent of (c) 15 ~ 80%.Oxygenatedchemicals Removal of catalyst is: (a) 10% ~ 95% La
2o
3, ZnO, ZrO
2, CaO, MgO, TiO
2and Cr
2o
3in at least one; The binding agent of (b) 5 ~ 90%.
Using toluene or benzene and methyl alcohol as raw material, High-efficient Production can be rich in the BTX aromatics of p-Xylol by alkylated reaction, reach adjustment aromatic hydrocarbon product structure, increase the object of p-Xylol output.Remove in bed at oxygenatedchemicals, carboxylic-acid impurity generation de-carbonyl reaction, the boiling point of reaction product is lower than benzene; Ketone impurity generation decomposition reaction generates hydro carbons, carbonic acid gas, and the boiling point of reaction product is also significantly reduced to below benzene boiling point.In stripping tower, the lower boiling alcohols, aldehydes and the ketone that only contain in aromatic hydrocarbon oil drain into out-of-bounds from stripper top, ensure that entering alcohols in the BTX aromatics of Aromatic Hydrocarbon United Plant, ketone, aldehydes and carboxylic-acid weight oxygenate content is all less than 0.5ppm.Operational path of the present invention, with the p-Xylol of toluene or benzene and the industrial urgent need of methanol production, can turn eliminate the disadvantageous effect that oxygenatedchemicals produces aromatics quality and equipment safety, facility investment and running cost low, achieve good technique effect.
Accompanying drawing explanation
Fig. 1 is the methylbenzene methanol methylation process schematic flow sheet eliminating oxygenatedchemicals impact.
In Fig. 1,1 for methylating/oxygenatedchemicals removes composite bed reactor, and 2 is water-and-oil separator, and 3 is stripping tower.
Below by embodiment, the invention will be further elaborated.
Embodiment
[embodiment 1]
The preparation method of methylation catalyst: at least one in 40% ~ 90% ZSM-5 zeolite or MCM-22 zeolite molecular sieve and the γ-Al of 15 ~ 80%
2o
3after binding agent fully mixes, add suitable quantity of water kneading and compacting, drying and 550
onamely catalyst body is obtained after C roasting.By the pickling process, ion exchange method and the chemical deposition that extensively adopt by MgO, La of 0.01 ~ 5.0%
2o
3, CaO and SiO
2in at least one load in catalyst body and namely obtain methylation catalyst.
The preparation method of oxygenatedchemicals Removal of catalyst: 10% ~ 95% La
2o
3, ZnO, ZrO
2, CaO, MgO, TiO
2and Cr
2o
3at least one in oxide compound and 5 ~ 90% γ-Al
2o
3, after silicon oxide or clay bond fully mix, add suitable quantity of water kneading and compacting, dry and 450
onamely oxygenatedchemicals Removal of catalyst is obtained after C roasting.
Load toluene methylation catalysts and oxygenatedchemicals Removal of catalyst respectively from top to bottom in reactor, the mass ratio of upper and lower bed is 5:1.Toluene: methyl alcohol (mol ratio)=2:1, toluene by weight air speed 1 hour
-1, temperature of reaction 370 DEG C, reaction pressure 0.5MPa; Liquid product is after water-and-oil separator is separated, and oil phase enters stripping tower and carries out light constituent separation, stripping tower top temperature 118 DEG C, stripping tower pressure on top surface 0.45MPa.As shown in schematic flow sheet, stream I, the Containing serum results such as the acetaldehyde in II and III, methyl alcohol, acetone, butanone and acetic acid are as shown in table 1:
Table 1
| Stream I (wtppm) | Stream I I (wtppm) | Stream I II (wtppm) | |
| Acetaldehyde | 8 | 8 | ≤0.5 |
| Methyl alcohol | 510 | 41 | ≤0.5 |
| Acetone | ≤0.5 | ≤0.5 | ≤0.5 |
| Butanone | ≤0.5 | ≤0.5 | ≤0.5 |
| Acetic acid | ≤0.5 | ≤0.5 | ≤0.5 |
Remove the toluene methylation product of reactor, water-and-oil separator and stripping tower through oxygenatedchemicals, the content of acetaldehyde, methyl alcohol, acetone, butanone and acetic acid is all reduced to below 0.5wtppm.
[embodiment 2]
Load Benzylation catalyzer and oxygenatedchemicals Removal of catalyst respectively from top to bottom in reactor, the mass ratio of upper and lower bed is 1:4.Toluene: methyl alcohol (mol ratio)=3:1, benzene weight space velocity 2 hours
-1, temperature of reaction 400 DEG C, reaction pressure 1MPa; Liquid product is after water-and-oil separator is separated, and oil phase enters stripping tower and carries out light constituent separation, stripping tower top temperature 124 DEG C, stripping tower pressure on top surface 0.51MPa.As shown in schematic flow sheet, stream I, the Containing serum results such as the acetaldehyde in II and III, methyl alcohol, acetone, butanone and acetic acid are as shown in table 2 below.
Table 2
| Stream I (wtppm) | Stream I I (wtppm) | Stream I II (wtppm) | |
| Acetaldehyde | 15 | 13 | ≤0.5 |
| Methyl alcohol | 806 | 65 | ≤0.5 |
| Acetone | ≤0.5 | ≤0.5 | ≤0.5 |
| Butanone | ≤0.5 | ≤0.5 | ≤0.5 |
| Acetic acid | ≤0.5 | ≤0.5 | ≤0.5 |
Remove the toluene methylation product of reactor, water-and-oil separator and stripping tower through oxygenatedchemicals, the content of acetaldehyde, methyl alcohol, acetone, butanone and acetic acid is all reduced to below 0.5wtppm.
[embodiment 3]
Load methylbenzene selective methylation catalyst and oxygenatedchemicals Removal of catalyst respectively from top to bottom in reactor, the mass ratio of upper and lower bed is 1:1.Toluene: methyl alcohol (mol ratio)=2:1, toluene by weight air speed 4 hours
-1, temperature of reaction 450
oc, reaction pressure 0.6MPa; Liquid product is after water-and-oil separator is separated, and oil phase enters stripping tower and carries out light constituent separation, stripping tower top temperature 120 DEG C, stripping tower pressure on top surface 0.50MPa.As shown in schematic flow sheet, stream I, the Containing serum results such as the acetaldehyde in II, III and IV, methyl alcohol, acetone, butanone and acetic acid are as shown in table 3 below.
Table 3
| Stream I (wtppm) | Stream I I (wtppm) | Stream I II (wtppm) | |
| Acetaldehyde | 9 | 7 | ≤0.5 |
| Methyl alcohol | 106 | 18 | ≤0.5 |
| Acetone | ≤0.5 | ≤0.5 | ≤0.5 |
| Butanone | ≤0.5 | ≤0.5 | ≤0.5 |
| Acetic acid | ≤0.5 | ≤0.5 | ≤0.5 |
Remove the toluene methylation product of reactor, water-and-oil separator and stripping tower through oxygenatedchemicals, the content of acetaldehyde, methyl alcohol, acetone, butanone and acetic acid is all reduced to below 0.5wtppm.
Claims (7)
1. remove an aromatic hydrocarbons methanol alkylation method for oxygenatedchemicals impurity, comprise the following steps:
A) it is 0.5 ~ 5 hour at temperature 350 DEG C ~ 480 DEG C, weight space velocity
-1, pressure is under 0.1 ~ 3MPa condition, benzene or toluene and methanol mixed raw material, by composite bed reactor, contact with composite catalyst, resultant of reaction stream I;
B) stream I through heat exchange and cooling after, enter water-and-oil separator, the lower floor's by-product aqueous phase after separation is disposed to out-of-bounds, upper oil phase overflow to downstream, as stream I I;
C) stream I I enters stripping tower, the C of separation
6light constituent drained into out-of-bounds by tower top in the past, the C that tower reactor obtains
6and later heavy constituent, as stream I II, be incorporated in Aromatic Hydrocarbon United Plant, isolate p-Xylol;
Wherein, composite catalyst is methylation catalyst and oxygenatedchemicals Removal of catalyst; Load methylation catalyst and oxygenatedchemicals Removal of catalyst respectively from top to bottom in composite bed reactor, both weight ratios are 1:9 ~ 9:1; Oxygenatedchemicals Removal of catalyst, with weight, comprises following component: (a) 10% ~ 95%La
2o
3, ZnO, ZrO
2, CaO, MgO, TiO
2and Cr
2o
3in at least one; The silicon oxide of (b) 5 ~ 90% or alumina binder.
2. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, is characterized in that the weight content of the alcohols in stream I II, ketone, aldehydes and carboxylic-acid oxygenatedchemicals is all less than 0.5ppm.
3. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, is characterized in that the weight content of ketone in stream I I and carboxylic-acid oxygenatedchemicals is all less than 0.5ppm.
4. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, it is characterized in that the tower top temperature of stripping tower is 110 ~ 130 DEG C, tower top pressure is 0.4 ~ 0.6MPa.
5. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, is characterized in that step c) in, the C of separation
6light constituent comprised C in the past
1~ C
5alkane, alkene, and acetaldehyde and methyl alcohol oxygenatedchemicals.
6. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, is characterized in that step c) in, the C that tower reactor obtains
6and heavy constituent comprises C later
6~ C
14aromatic hydrocarbons, alkane and alkene.
7. the aromatic hydrocarbons methanol alkylation method removing oxygenatedchemicals impurity according to claim 1, it is characterized in that methylation catalyst, with weight, comprise following component: at least one in (a) 40% ~ 90%ZSM-5 zeolite or MCM-22 zeolite molecular sieve; MgO, La of (b) 0.01 ~ 5.0%
2o
3, CaO and SiO
2in at least one; The silicon oxide of (c) 15 ~ 80% or alumina binder.
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| CN106608794B (en) * | 2015-10-22 | 2019-10-11 | 中国石油化工股份有限公司 | The method of oxygen-containing organic compound impurity in Arene removal logistics |
| CN112521244B (en) * | 2019-09-19 | 2023-08-04 | 中国石油化工股份有限公司 | Method and device for reducing byproducts in circulating hydrogen in hydrogen-contacting fixed bed reaction system |
| CN112521243B (en) * | 2019-09-19 | 2023-07-04 | 中国石油化工股份有限公司 | Method and system for long-period running toluene methanol methylation reaction |
| CN112619696B (en) * | 2019-10-09 | 2022-12-09 | 中国石油化工股份有限公司 | Composite bed hydrocracking catalyst system and preparation method and application thereof |
| CN111635780B (en) * | 2020-06-04 | 2021-05-14 | 浙江大学 | Method for producing BTX (benzene-toluene-xylene) from coal tar |
| CN114426456A (en) * | 2020-10-10 | 2022-05-03 | 中国石油化工股份有限公司 | Combined process for benzene and heavy aromatic transalkylation and toluene methylation |
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| CN1231653A (en) * | 1996-10-02 | 1999-10-13 | 美孚石油公司 | Selective para-xylene production by toluene methylation |
| CN102007199A (en) * | 2008-04-17 | 2011-04-06 | 尤尼威蒂恩技术有限公司 | Systems and methods for removing impurities from a feed fluid |
| CN102395544A (en) * | 2009-04-14 | 2012-03-28 | 埃克森美孚化学专利公司 | Process for the purification of paraxylene |
| CN102464559A (en) * | 2010-11-17 | 2012-05-23 | 中国石油化工股份有限公司 | Method for producing alkylated aromatic hydrocarbon |
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|---|---|---|---|---|
| CN1231653A (en) * | 1996-10-02 | 1999-10-13 | 美孚石油公司 | Selective para-xylene production by toluene methylation |
| CN102007199A (en) * | 2008-04-17 | 2011-04-06 | 尤尼威蒂恩技术有限公司 | Systems and methods for removing impurities from a feed fluid |
| CN102395544A (en) * | 2009-04-14 | 2012-03-28 | 埃克森美孚化学专利公司 | Process for the purification of paraxylene |
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