CN103121910A - Method for disproportionation and transalkylation of toluene heavy aromatics - Google Patents
Method for disproportionation and transalkylation of toluene heavy aromatics Download PDFInfo
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- CN103121910A CN103121910A CN201110367325XA CN201110367325A CN103121910A CN 103121910 A CN103121910 A CN 103121910A CN 201110367325X A CN201110367325X A CN 201110367325XA CN 201110367325 A CN201110367325 A CN 201110367325A CN 103121910 A CN103121910 A CN 103121910A
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- catalyzer
- transalkylation
- heavy aromatics
- disproportionation
- toluene
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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Abstract
The invention relates to a method for disproportionation and transalkylation of toluene heavy aromatics and mainly solves the problems that aromatic ring loss rate is high, reaction hydrogen consumption is high and the like during reaction in the prior art. Catalyst used in the method includes: (a) at least one of platinum or palladium metals; and (b) at least one of ZSM-12, mordenite and zeolite. The catalyst is preprocessed in a way that the catalyst is contacted with sulfur compounds at 200-600 DEG C to allow sulfur content of the catalyst to be not larger than metal absorption saturation value. The problems that aromatic ring loss rate is high, reaction hydrogen consumption is high and the like are solved. The method is applicable to industrial production of disproportionation and transalkylation of toluene heavy aromatics.
Description
Technical field
The present invention relates to the disproportionation of a kind of toluene and heavy aromatics and the method for transalkylation.
Background technology
P-Xylol in C8 aronmatic is one of main basic organic of petrochemical industry, in numerous chemical production field such as chemical fibre, synthetic resins, agricultural chemicals, medicine, purposes is widely arranged.For increasing production of xylol, utilize toluene disproportionation or toluene and carbon nine and above heavy aromatics (C thereof
9 +A) transalkylation reaction generates benzene and C8 aronmatic, reaches the purpose of increasing yield of p-xylene.
Along with day by day becoming heavily of upstream reforming material, the comprehensive utilization of heavy arene becomes the problem that people are concerned about.C9 aromatic (C
9A) the existing more ripe technology of utilizing, by with the transalkylation reaction increasing production of xylol of toluene.And carbon ten and above heavy aromatics (C thereof
10 +A) can only partly be utilized at present, fused ring compound wherein easily aggravates the coking deactivation of catalyzer.For improving the processing power of heavy aromatics, improve the stability of catalyzer, can introduce the hydrogenation metal component on molecular sieve catalyst.But then, because metal has than the strong hydrogenation performance, can promote the hydrogenation hydrogenolysis of aromatic hydrocarbons and discharge a large amount of reaction heat, causing reaction process aromatic ring loss increase, hydrogen consumption to increase, even can cause the startup procedure temperature runaway.Usually metal catalyst is carried out pre-treatment to suppress the hydrogenation side reaction of metal component, be beneficial to its operation steady in a long-term.Document Journal of catalysis, 99,39-52 (1986), Applied catalysis, 10,291-295 (1984) have discussed interaction and the sulfuration mechanism of metal and sulphur, but the sulphur chemisorption suppresses its hydrogenation activity in the metallic surface.CN1013361 discloses a kind of preparation and vulcanization process of dehydrogenation catalyst, and the method adopts the wet method method for pre-sulphuration to introduce the sulphur component after the catalyzer roasting, then reduces with hydrogen, completes simultaneously sulfuration.
US20080221375 discloses a kind of disproportionation and transalkylation catalyst and pretreatment process thereof, and the method is introduced the sulphur component on the rhenium-containing metal catalyst.The introducing of sulphur can suppress the demethylation side reaction, and reduces the reactive hydrogen consumption, but this patent is not revealed concrete sulfidation.
CN1122571 discloses a kind of catalyst for toluene disproportionation and transalkylation that contains precious metal, this catalyzer is with the mordenite of 10～80% (weight) or the ZSM-5 of β zeolite and 0～70% (weight), γ-the Al2O3 of 5～90% (weight) is carrier, load 0.001～0.5 weight part platinum, load 0.01～10.0 weight part tin or 0.01～7.0 weight part lead suppress the hydrogenation activity of platinum simultaneously.This catalyzer can be processed high C
9 +The A raw material, and improved xylol productive rate and catalyst stability.In above-mentioned document, carrying out toluene and C
9 +When A disproportionation and transalkylation reaction, there are the shortcomings such as the aromatic ring rate of loss is higher, the reactive hydrogen consumption is higher, thereby limited its industrial application.
Summary of the invention
Technical problem to be solved by this invention is to have the problem that the aromatic ring rate of loss is higher, the reactive hydrogen consumption is higher in existing toluene and heavy aromatics disproportionation and transalkylation catalyst technology.A kind of new toluene and the method for heavy aromatics disproportionation and transalkylation are provided.The method is used for toluene and heavy aromatics disproportionation and transalkylation reaction, has advantages of effectively to reduce reaction process aromatic ring rate of loss and reactive hydrogen consumption.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method of toluene and heavy aromatics disproportionation and transalkylation, wherein catalyzer used contains
(a) be selected from least a in platinum or metallic palladium;
(b) be selected from least a in ZSM-12, mordenite, zeolite;
The described catalyzer of pre-treatment in the following manner: be under 200～600 ℃ in temperature, sulfocompound is contacted with catalyzer, make the sulphur content on catalyzer be less than or equal to the metal adsorption saturation value.
In technique scheme, in weight hundred deals, the amount that catalyzer contains platinum or palladium is 0.01～0.5%, and catalyzer contacts with sulfocompound after reduction activation again, and Contact Temperature is 350～500 ℃.The sulfocompound injection mode is, with sulfocompound be blended in contact with catalyzer in the charging medium or sulfocompound with contact with catalyzer again after hydrogen mixes, the amount of sulfocompound used should make that in gas mixture, sulphur content reaches 50～1000ppm (w).Sulfocompound is selected from least a in hydrogen sulfide, Dimethyl sulfide, dimethyl thioether, dimethyl disulfide, methylethyl sulphur, diethyl sulfide, ammonium sulfide.When sulfidation finished, on catalyzer, the mol ratio of absorption sulphur and loaded metal was 0.05～1.5, preferred 0.1～0.8.Catalyzer contacts with the material that contains toluene/benzene and heavy aromatics after sulfidizing again disproportionation and transalkylation reaction occurs.
The method of the toluene in the present invention and heavy aromatics disproportionation and transalkylation, take toluene and carbon nine and above heavy aromatics thereof as raw material, wherein the part by weight of toluene and carbon nine and above heavy aromatics thereof is 100: 0～20: 80, it is 200～500 ℃ in temperature, pressure is 1.5～4.0MPa, and the charging weight hourly space velocity is 1.0～5.0h
-1, hydrogen hydrocarbon molecule ratio is under 2.0～5.0 conditions, and raw material contacts with catalyzer, and reaction generates benzene, dimethylbenzene effluent.
In the present invention, by metal-modified catalyzer is carried out sulfidizing, make the sulphur selective adsorption in the defective locations of metal grain, on the one hand large metallic particles is carried out physical segmentation, suppressed to occur such as multidigit catalyzed reactions such as carbon deposit reactions on metal; On the other hand, thereby the electron donation that transfer transport has weakened atoms metal also can occur in sulphur and intermetallic, has weakened its Hydrogenation, reduces the aromatic hydrocarbons loss.By controlling the state of vulcanization of metal, alternative weakens the saturated performance of hydrogenation of metal, but does not have influence on the stability of catalyzer.
The disproportionation and the transalkylation reaction that method of the present invention are used for toluene and heavy aromatics can significantly reduce aromatic hydrocarbon ring loss rate and reactive hydrogen consumption, keep simultaneously stability preferably, have improved the economical in reaction performance, have obtained technique effect preferably.
The present invention is further elaborated below by embodiment.
Embodiment
[embodiment 1]
With Na
2O content is less than 0.1% (weight), SiO
2/ Al
2O
3Molecular ratio is 30 ammonium type β zeolite 66.7 grams and Na
2O content is less than the γ-Al of 0.1% (weight)
2O
3H
2O 57.1 grams evenly mix, and then add a certain amount of rare nitric acid, field mountain valley with clumps of trees and bamboo powder to mediate evenly, and carrier is made in extruded moulding, roasting, and pelletizing is placed in steeper.With a certain amount of platinum acid chloride solution impregnated carrier, 4 hours, 500 ℃ roastings of 120 ℃ of dryings were reduced under 400 ℃ after 3 hours, made catalyst A (0.1wt%Pt/ β).
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, will mix with hydrogen after a certain amount of dimethyl disulfide gasification, in gas mixture, sulphur content is 300ppm.Gas mixture once by beds, is vulcanized under 400 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.5, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer and carries out the reactive behavior investigation.Reaction conditions is: the gross weight air speed is 3.0 hours
-1, 375 ℃ of temperature of reaction, reaction pressure 3.0MPa, the hydrogen hydrocarbon molecule is than 3.0.Reaction raw materials is toluene: C
9 +A=30: 70 (weight), wherein C
9 +Contain 15% (weight) C in A
10 +A。C
9The A raw material weight consists of: propyl benzene 4.2%, the first and second benzene 29.04%, trimethylbenzene 59.6%, C
10 +A weight consists of: diethylbenzene 3.33%, dimethyl ethylbenzene 26.96%, methyl propyl benzene 2.32%, durene 28.84%, methylnaphthalene 14.49%, dimethylnaphthalene 11.16%, other 12.90%.
[embodiment 2]
With Na
2O content is less than 0.1% (weight), SiO
2/ Al
2O
3Molecular ratio is 30 ammonium type mordenite 66.7 grams and Na
2O content is less than the γ-Al of 0.1% (weight)
2O
3H
2O 57.1 grams evenly mix, and then add a certain amount of rare nitric acid, field mountain valley with clumps of trees and bamboo powder to mediate evenly, and carrier is made in extruded moulding, roasting, and pelletizing is placed in steeper.With a certain amount of palladium chloride solution impregnated carrier, 4 hours, 500 ℃ roastings of 120 ℃ of dryings were reduced under 400 ℃ after 3 hours, made catalyst B (0.2wt%Pd/ mordenite).Catalyst vulcanization condition and performance evaluation condition such as embodiment 1.
[embodiment 3]
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, will mix with hydrogen after a certain amount of dimethyl disulfide gasification, in gas mixture, sulphur content is 300ppm.Gas mixture once by beds, is vulcanized under 450 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.3, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 4]
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, a certain amount of hydrogen sulfide is mixed with hydrogen, in gas mixture, sulphur content is 800ppm.Gas mixture once by beds, is vulcanized under 350 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.8, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 5]
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, with a certain amount of dimethyl thioether and aromatic hydrocarbons mixing of materials, in compound, sulphur content is 300ppm.With after compound gasification once by beds, vulcanize under 350 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.2, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 6]
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, with a certain amount of dimethyl thioether and aromatic hydrocarbons mixing of materials, in compound, sulphur content is 300ppm.With after compound gasification by beds, vulcanize under 300 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.3, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 7]
Get the 100ml catalyst B, be placed in tubular reactor, pass into 500ml/min hydrogen, with a certain amount of dimethyl disulfide and aromatic hydrocarbons mixing of materials, in compound, sulphur content is 200ppm.With after compound gasification once by beds, vulcanize under 350 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.2, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 8]
Get the 100ml catalyst B, be placed in tubular reactor, pass into 500ml/min hydrogen, will mix with hydrogen after a certain amount of dimethyl disulfide gasification, in gas mixture, sulphur content is 400ppm.Gas mixture once by beds, is vulcanized under 400 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.3, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[embodiment 9]
Get the 100ml catalyst B, be placed in tubular reactor, pass into 500ml/min hydrogen, will mix with hydrogen after a certain amount of dimethyl disulfide gasification, in gas mixture, sulphur content is 600ppm.Gas mixture once by beds, is vulcanized under 400 ℃, make that on catalyzer, the mol ratio of sulphur content and metal content reaches 0.6, stop injecting sulfide.Pass into and contain toluene and C
9 +The material of A contacts with catalyzer, reacts under certain condition.Pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[Comparative Examples 1]
Get the 100ml catalyst A, be placed in tubular reactor, pass into 500ml/min hydrogen, purge 2 hours under 400 ℃, 3.0MPa, pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
[Comparative Examples 2]
Get the 100ml catalyst B, be placed in tubular reactor, pass into 500ml/min hydrogen, purge 2 hours at 400 ℃, 3.0MPa, pass into and contain toluene and C
9 +The material of A and catalyzer contact reacts, catalyst performance evaluation condition such as embodiment 1.
Evaluating catalyst result after the described method of embodiment 1～9 and Comparative Examples 1～2 is processed is as shown in table 1.
Catalyzer can effectively reduce the aromatic ring loss through after suitable pre-treatment.Under more excellent condition, Catalyst Conversion is 46.22wt%, selectivity 87.11wt%, and the aromatic ring rate of loss is 1.13wt%.
Table 1 catalyst vulcanization condition and evaluation result
Claims (10)
1. the method for a toluene and heavy aromatics disproportionation and transalkylation, wherein catalyzer used contains
(a) be selected from least a in platinum or metallic palladium;
(b) be selected from least a in ZSM-12, mordenite, zeolite;
And the described catalyzer of pre-treatment in the following manner: be under 200～600 ℃ in temperature, sulfocompound is contacted with catalyzer, make the sulphur content on catalyzer be less than or equal to the metal adsorption saturation value.
2. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation, is characterized in that with hundred parts of content meters of weight, containing platinum or palladium amount in catalyzer is 0.01～0.5%.
3. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation, is characterized in that catalyzer contacts with sulfocompound again after reduction.
4. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation, is characterized in that catalyzer and sulfocompound Contact Temperature are 300～500 ℃.
5. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation, is characterized in that the sulfide injection mode is, sulfide is blended in and contacts with catalyzer in the charging medium or sulfide and hydrogen contact with catalyzer after mixing again.
6. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation is characterized in that the sulfide injection rate should make that in the sulfur-bearing gas mixture, sulphur content is 10～1000ppm (w).
7. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation is characterized in that sulfide is selected from least a in hydrogen sulfide, Dimethyl sulfide, dimethyl thioether, dimethyl disulfide, methylethyl sulphur, diethyl sulfide, ammonium sulfide.
8. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation is characterized in that on catalyzer, the mol ratio of absorption sulphur and loaded metal is 0.05～1.5.
9. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation is characterized in that on catalyzer, the mol ratio of absorption sulphur and loaded metal is 0.1～0.8.
10. the method for toluene according to claim 1 and heavy aromatics disproportionation and transalkylation, is characterized in that contacting generation disproportionation and transalkylation reaction with the material that contains toluene/benzene and heavy aromatics after catalyst vulcanization again.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104338552A (en) * | 2013-07-31 | 2015-02-11 | 中国石油化工股份有限公司 | Sulfuration modification method of xylene isomerization catalyst |
| CN110180581A (en) * | 2018-02-22 | 2019-08-30 | 中国石油化工股份有限公司 | Catalyst and its in C11+Application in heavy aromatics lighting reaction |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101124186A (en) * | 2005-01-06 | 2008-02-13 | 弗纳技术股份有限公司 | Toluene disproportionation process utilizing mild sulfiding during startup |
-
2011
- 2011-11-18 CN CN201110367325XA patent/CN103121910A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101124186A (en) * | 2005-01-06 | 2008-02-13 | 弗纳技术股份有限公司 | Toluene disproportionation process utilizing mild sulfiding during startup |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104338552A (en) * | 2013-07-31 | 2015-02-11 | 中国石油化工股份有限公司 | Sulfuration modification method of xylene isomerization catalyst |
| CN104338552B (en) * | 2013-07-31 | 2017-07-25 | 中国石油化工股份有限公司 | A kind of sulfide modifier method of xylene isomerization catalyst |
| CN110180581A (en) * | 2018-02-22 | 2019-08-30 | 中国石油化工股份有限公司 | Catalyst and its in C11+Application in heavy aromatics lighting reaction |
| CN110180581B (en) * | 2018-02-22 | 2021-11-30 | 中国石油化工股份有限公司 | Catalysts and their use in C11+Application in reaction for converting heavy aromatics into light aromatics |
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Application publication date: 20130529 |