CN103120956A - Catalyst for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons to produce more dimethylbenzene and preparation method thereof - Google Patents
Catalyst for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons to produce more dimethylbenzene and preparation method thereof Download PDFInfo
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- CN103120956A CN103120956A CN2011103694646A CN201110369464A CN103120956A CN 103120956 A CN103120956 A CN 103120956A CN 2011103694646 A CN2011103694646 A CN 2011103694646A CN 201110369464 A CN201110369464 A CN 201110369464A CN 103120956 A CN103120956 A CN 103120956A
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Abstract
The invention relates to a catalyst for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons to produce more dimethylbenzene and a preparation method thereof, mainly solving the problems in the prior art that the conversion level of polycyclic aromatic hydrocarbons is low, the dimenthylbenzene yield and selectivity are low and the catalyst deactivation rate is high. The problems are better solved by adopting the catalyst and the preparation method thereof. The catalyst comprises 30-60wt% of mixture of FAU type zeolite and at least one molecular sieve from MOR, BEA, MFI and MCM-22, 38-69.9wt% of at least one of gamma-alumina, eta-alumina and pseudo-boehmite as a binder, 0.04-0.9wt% of at least one metal from Pt, Pd and Ir and 0.1-1wt% of at least one of Zn, Sn, La, Ce and Mo. The catalyst can be used in the industrial production of increasing production of dimethylbenzene by converting heavy polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons.
Description
Technical field
The polycyclic aromatic hydrocarbon that the present invention relates to a kind of voluminous dimethylbenzene is converted into the Catalysts and its preparation method of mononuclear aromatics.
Background technology
Oil is the important earth resource that the mankind depend on for existence, and is closely related with people's clothing, food, lodging and transportion--basic necessities of life.But be subject to petroleum resources limited in world wide and the continuous intensification of exploiting out the oil product degree of heaviness in recent years, force people reasonably to fully utilize these mink cell focuses.In heavy oil product, the annual production of heavy aromatics increases year by year, and except seldom a part is as organic solvent, major part is impregnated in fuel and uses, and no matter from environmental protection or economic angle, Heavy Aromatic Hydrocarbons is not all fully utilized effectively.Consider from the market demand, production cost and environmental requirement equal angles, utilizing the Organic Chemicals of these heavy aromatics exploitation high added values is important developing direction.The light aromatic hydrocarbons such as benzene,toluene,xylene is all important Organic Chemicals, and benzene is the basic material of the products such as preparation styrene, nylon, terylene; And toluene is used as the blending compound of gasoline to improve octane number, also can produce paint, binding agent, organic solvent etc. in industry, agricultural and medically be widely used; Dimethylbenzene more is used to produce the products such as polyester, chemical fibre, and the demand of market paraxylene also grows with each passing day, and its importance is suitable with benzene in aromatic hydrocarbon resource.Therefore developing heavy aromatics rationally transforms the light aromatics technology and has become one of development strategy of 21 century each large petro-chemical corporation of the world.
Uop Inc. has developed the first hydrocracking of arene stream, will be rich in benzene, toluene and C again
9 +The hydrogenation logistics carry out the technique (WP2009008876 that transalkylation is produced dimethylbenzene, open day on January 15th, 2009), the hydrocracking catalyst of this process using is the amorphous silicon aluminium catalyst that contains VIII family or group vib metal, and reaction condition is that 232～468 ℃, 3.5～20.8MPa, LHSV are 0.1～30h
-1Alkylation reaction condition is that 200～525 ℃, LHSV are 0.2～10h
-1, adopt MCM-22, the MOR, the FAU type molecular sieve catalyst that contain non-skeleton metal, wherein molecular sieve accounts for 30～50wt%.
USP4,341,622 disclose a kind of method of utilizing the heavy reformate to produce BTX.The zeolite that the method adopts that restricted index is 1～12, silica/alumina molar ratio (silica alumina ratio) is 12 or more, hang down acid activity is catalyst, reformate is reacted under the condition of 427～540 ℃, then the product separated is obtained benzene, toluene and dimethylbenzene.Described catalyst contains the VIII family noble metal of hydro-dealkylation function, preferred platinum, and the silica alumina ratio of zeolite used is preferably greater than 200, and more preferably greater than 500, preferred zeolite is ZSM-5.Select the zeolite of high silica alumina ratio for reducing zeolite acidity, keep as far as possible dimethylbenzene and be not converted in reaction.
CN1934058A discloses a kind of with dihydroindene and C
10Be C Deng polycyclic aromatic hydrocarbon conversion and transalkylation
8The method of aromatic hydrocarbons, the catalyst that the method is used comprises solid acid carrier (as: modenite) and metal component (as: rhenium), can produce valuable dimethylbenzene by the method.
CN200580009162 discloses a kind of method that polycyclic aromatic hydrocarbon is catalytically conveted to dimethylbenzene, and the catalyst carrier that the method is used is selected from modenite, mazzite, β zeolite, ZSM-11, ZSM-12, ZSM-22, ZSM-23, MFI topology zeolite, NES topology zeolite, EU-1, MAPO-36, MAPSO-31, SAPO-11, SAPO-41 and silica-alumina and their combination.This catalyst can be used for processing the feed stream that contains high boiling substance, can also to a certain degree reduce the terminal point of the 99.5wt% of feed stream when generating dimethylbenzene.
Summary of the invention
One of technical problem to be solved by this invention is that the polycyclic aromatic hydrocarbon conversion level is low in order to overcome the catalyst that exists in prior art and to be used for the heavy polycyclic aromatic hydrocarbon and to be converted into the mononuclear aromatics reaction, the dimethylbenzene yield is low and selectively low, the problem that catalyst deactivation rate is fast provides a kind of new polycyclic aromatic hydrocarbon that is used for voluminous dimethylbenzene to be converted into the catalyst of mononuclear aromatics.This catalyst is used for the reaction that polycyclic aromatic hydrocarbon is converted into mononuclear aromatics, has a polycyclic aromatic hydrocarbon conversion level high, and the dimethylbenzene yield is high and selective high, the advantage that catalyst deactivation rate is slow.
The polycyclic aromatic hydrocarbon that two of technical problem to be solved by this invention is to provide a kind of voluminous dimethylbenzene corresponding with one of technical solution problem is converted into the preparation method of mononuclear aromatics catalyst.
For one of solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of polycyclic aromatic hydrocarbon of voluminous dimethylbenzene is converted into the catalyst of mononuclear aromatics, comprises by weight percentage following component:
A) 30～60%FAU type zeolite and the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22;
B) 38～69.9% be selected from least a for binding agent in gama-alumina, η-aluminium oxide or boehmite;
C) 0.04～0.9% at least a metal or its oxide that is selected from Pt, Pd or Ir;
D) 0.1～1% at least a metal or its oxide that is selected from Zn, Sn, La, Ce or Mo.
In technique scheme, FAU type zeolite and be selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 and be the sodium weight content lower than 2% Hydrogen or ammonium type zeolite during used catalyst forms; In mixture by weight percentage the amount preferable range of FAU type zeolite be 50～70%, the amount preferable range that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 is 30～50%.
For solve the problems of the technologies described above two, the technical solution used in the present invention is as follows: a kind of polycyclic aromatic hydrocarbon of voluminous dimethylbenzene is converted into the preparation method of the catalyst of mononuclear aromatics, comprises the following steps:
1. with after being selected from least a binding agent in gama-alumina, η-aluminium oxide or boehmite and carrying out kneading, moulding, drying of the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 of the FAU type zeolite of aequum and aequum and aequum, obtain catalyst carrier at 450～650 ℃ of roasting 0.5～24h;
2. be impregnated into 0.5～24h on catalyst carrier in 30～50 ℃ after the precursor solution that is selected from least a metal in Zn, Sn, La, Ce or Mo or its oxide of the precursor solution that is selected from least a metal in Pt, Pd or Ir or its oxide of aequum and aequum being mixed, obtain finished catalyst at 300～450 ℃ of roasting 0.5～24h after drying.
In technique scheme, preferred version can add the extrusion aid that calculates 2～5% weight by the carrier butt, for example sesbania powder in the catalyst carrier preparation process; Can add at least a and water volume ratio acid solution of 1: 1～1: 5 that is selected from hydrochloric acid, nitric acid, acetic acid, tartaric acid, citric acid or oxalic acid by carrier butt calculating 3～6% weight is gelatinizing agent.
In technique scheme, the precursor solution preferred version of Pt metal used is chloroplatinic acid; The precursor solution preferred version of metal Pd is at least a in palladium nitrate or palladium bichloride; The precursor solution preferred version of metal Ir is chloro-iridic acid; The predecessor preferred version of Metal Zn used is at least a in zinc oxide, zinc chloride or zinc nitrate; The precursor solution preferred version of metal Sn is at least a in stannous chloride or butter of tin; The precursor solution preferred version of metal La is at least a in lanthanum nitrate or carbonic acid bright-coloured; The precursor solution preferred version of metal Ce is cerous nitrate; The precursor solution preferred version of metal M o is ammonium molybdate.
Catalyst provided by the invention is the catalyst that a kind of polycyclic aromatic hydrocarbon for voluminous dimethylbenzene is converted into mononuclear aromatics, can be used for producing benzene, toluene and dimethylbenzene.
In the present invention due to type zeolite such as the FAU that has selected three-dimensional macropore, BEA as the catalyst acid center, be conducive to the acid site that the large molecule of heavy arene enters in the duct and carry out ring-opening reaction, product molecule after conversion can pass through the duct rapid diffusion, thereby has delayed the deactivation rate of catalyst; The precious metal element that has hydrogenating function by load is controlled its load capacity at a zone of reasonableness, can effectively improve the degree of unsaturation of Polycyclic Aromatic Hydrocarbon Mixture raw material, helps the deep conversion polycyclic aromatic hydrocarbon; The introducing of aided metal can improve the decentralization of carried noble metal, delays accumulation of metal and grows up, and can effectively improve the service life of catalyst; The rational proportion of catalyst acid center and metallic element takes off alkyl, transalkylation and light aromatic hydrocarbons aromatization generation with part during will making the hydrogenation open loop simultaneously, these reactions will improve the yield of dimethylbenzene wherein and selective in original mononuclear aromatics component in keeping feed stream as far as possible, obtained technique effect preferably.
The present invention uses overcritical fixed bed reactors to carry out the reactivity worth investigation that polycyclic aromatic hydrocarbon is converted into mononuclear aromatics, 12 millimeters of reactor inside diameter Ф, 800 millimeters of length, stainless steel.Adopt electrical heating, temperature is controlled automatically.It is supporter that reactor bottom is filled 2～3 millimeters beades of Ф, catalyst filling 5 grams in reactor, and 2～3 millimeters beades of Ф are filled on top, are made for the use of raw material preheating and vaporization.The raw material Polycyclic Aromatic Hydrocarbon Mixture mixes with hydrogen, by beds, makes polycyclic aromatic hydrocarbon be converted into the mononuclear aromatics mixture of voluminous dimethylbenzene from top to bottom.
Polycyclic Aromatic Hydrocarbon Mixture is the autogamy raw material, and experimental data is calculated as follows.
The present invention is further elaborated below by embodiment.
The specific embodiment
[embodiment 1]
Be 25g FAU type zeolite (being purchased Hydrogen), 25g MFI type zeolite (being purchased Hydrogen) and 50g γ-Al with butt
2O
3(industrial goods) add blender to evenly, then add 3g sesbania powder, 1: 1 HNO of 5g volume ratio in mixture
3Solution and 40g deionized water are ground and are evenly made the dough that is suitable for extruding.It is extruded by mould, and shape is elongated cylindrical (diameter 1.7mm), after 120 ℃ of oven dry in 550 ℃ of roasting 4h, then it is cut into consistent size carrier granular (1.7 * 4.0mm), be designated as Z1.
Chloroplatinic acid and zinc oxide wiring solution-forming are flooded carrier granular under 40 ℃, and the amount that contains Pt and Zn in maceration extract is respectively 0.1% and 0.5% of carrier butt weight, and dipping 8h at 450 ℃ of roasting 3h, makes finished catalyst A also after drying.
[embodiment 2～6]
Preparation method and process according to embodiment 1 provides in the process to Z1 carrier granular dipping, have prepared a series of finished catalysts by the kind that changes metal precursor in maceration extract, see Table 1.
Table 1
[embodiment 7～10]
Preparation method and process according to embodiment 1 provides in the process to Z1 carrier granular dipping, have prepared a series of finished catalysts by the pickup that changes metal, see Table 2.
Table 2
[embodiment 11～15]
Preparation method and process according to embodiment 1 provides by changing the contamination of metal precursor in carrier composition and maceration extract, have prepared a series of finished catalysts, see Table 3.
Table 3
Catalyst A～the O that makes with embodiment 1～15 (highest response pressure 10MPa, serviceability temperature are room temperature～600 ℃) on overcritical fixed bed reactors investigates the ability of the mononuclear aromatics such as BTX (B is that benzene, T are that toluene, X are dimethylbenzene) that Polycyclic Aromatic Hydrocarbon Mixture is converted into.Table 4 forms for the Polycyclic Aromatic Hydrocarbon Mixture raw material.Catalyst packing 5g is at 380 ℃ of reaction temperatures, reaction pressure 6MPa, weight (hourly) space velocity (WHSV) degree 2.0hr
-1, contact with catalyst under hydrogen/hydrocarbon mol ratio 5.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 5.
Table 4 raw material forms
| Raw material forms | Non-aromatic | Benzene | Toluene | Ethylbenzene | Dimethylbenzene | Decahydronaphthalene | Naphthane | Naphthalene |
| Content (wt%) | 0.02 | 24.54 | 24.61 | 5 | 0.02 | 14.81 | 15.25 | 15.75 |
Table 5 polycyclic aromatic hydrocarbon conversion results
| The catalyst numbering | Total conversion (wt%) | BTX selective (wt%) | X selective (wt%) |
| A | 70.1 | 41.5 | 22.3 |
| B | 69.3 | 41.4 | 22.0 |
| C | 64.4 | 42.0 | 24.1 |
| D | 64.8 | 42.6 | 24.7 |
| E | 73.8 | 44.6 | 26.7 |
| F | 72.5 | 43.8 | 26.2 |
| G | 76.4 | 46.1 | 27.5 |
| H | 74.1 | 45.2 | 26.4 |
| I | 78.3 | 46.9 | 28.6 |
| J | 78.0 | 46.2 | 28.1 |
| K | 73.8 | 45.3 | 26.3 |
| L | 72.1 | 44.4 | 26.9 |
| M | 73.2 | 44.7 | 26.2 |
| N | 74.0 | 45.5 | 26.0 |
| O | 80.0 | 49.2 | 30.3 |
[comparative example 1～6]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed bed reactors.Catalyst packing 5g is at 380 ℃ of reaction temperatures, reaction pressure 5MPa, weight (hourly) space velocity (WHSV) degree 2.5hr
-1, contact with catalyst under hydrogen/hydrocarbon mol ratio 6.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 6.
Table 6 polycyclic aromatic hydrocarbon conversion results
| The catalyst numbering | Total conversion (wt%) | BTX selective (wt%) | X selective (wt%) |
| A | 69.5 | 43.8 | 24.6 |
| B | 67.6 | 42.9 | 23.9 |
| C | 64.0 | 44.7 | 25.5 |
| D | 67.1 | 45.0 | 26.1 |
| E | 72.0 | 46.3 | 28.0 |
| F | 72.9 | 47.0 | 28.8 |
Claims (8)
1. the polycyclic aromatic hydrocarbon of a voluminous dimethylbenzene is converted into the catalyst of mononuclear aromatics, comprises by weight percentage following component:
A) 30～60%FAU type zeolite and the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22;
B) 38～69.9% be selected from least a for binding agent in gama-alumina, η-aluminium oxide or boehmite;
C) 0.04～0.9% at least a metal or its oxide that is selected from Pt, Pd or Ir;
D) 0.1～1% at least a metal or its oxide that is selected from Zn, Sn, La, Ce or Mo.
2. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 1 is converted into the catalyst of mononuclear aromatics, it is characterized in that FAU type zeolite and be selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 being the sodium weight content lower than 2% Hydrogen or ammonium type zeolite.
3. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 1 is converted into the catalyst of mononuclear aromatics, it is characterized in that in mixture that the amount of FAU type zeolite is 50～70% by weight percentage, the amount that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 is 30～50%.
4. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene claimed in claim 1 is converted into the preparation method of the catalyst of mononuclear aromatics, comprises the following steps:
1. with after being selected from least a binding agent in gama-alumina, η-aluminium oxide or boehmite and carrying out kneading, moulding, drying of the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 of the FAU type zeolite of aequum and aequum and aequum, obtain catalyst carrier at 450～650 ℃ of roasting 0.5～24h;
2. be impregnated into 0.5～24h on catalyst carrier in 30～50 ℃ after the precursor solution that is selected from least a metal in Zn, Sn, La, Ce or Mo or its oxide of the precursor solution that is selected from least a metal in Pt, Pd or Ir or its oxide of aequum and aequum being mixed, obtain finished catalyst at 300～450 ℃ of roasting 0.5～24h after drying.
5. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 4 is converted into the preparation method of the catalyst of mononuclear aromatics, it is characterized in that in the catalyst carrier preparation process, preferred version can add the extrusion aid that calculates 2～5% weight by the carrier butt.
6. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 4 is converted into the preparation method of the catalyst of mononuclear aromatics, it is characterized in that can add at least a and water volume ratio acid solution of 1: 1～1: 5 that is selected from hydrochloric acid, nitric acid, acetic acid, tartaric acid, citric acid or oxalic acid by carrier butt calculating 3～6% weight in the catalyst carrier preparation process is gelatinizing agent.
7. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 4 is converted into the preparation method of the catalyst of mononuclear aromatics, and the precursor solution that it is characterized in that described Pt metal is chloroplatinic acid; The precursor solution of metal Pd is at least a in palladium nitrate or palladium bichloride; The precursor solution of metal Ir is chloro-iridic acid.
8. the polycyclic aromatic hydrocarbon of voluminous dimethylbenzene according to claim 4 is converted into the preparation method of the catalyst of mononuclear aromatics, and the predecessor that it is characterized in that described Metal Zn is at least a in zinc oxide, zinc chloride or zinc nitrate; The precursor solution of metal Sn is at least a in stannous chloride or butter of tin; The precursor solution of metal La is at least a in lanthanum nitrate or carbonic acid bright-coloured; The precursor solution of metal Ce is cerous nitrate; The precursor solution of metal M o is ammonium molybdate.
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|---|---|---|---|---|
| CN104549473A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Catalyst for converting sulphur-containing polycyclic aromatic hydrocarbon into mononuclear aromatic and preparation method of catalyst |
| CN104549469A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Reproducible catalyst for converting polycyclic aromatic hydrocarbon into monocyclic aromatic hydrocarbon and preparation method of reproducible catalyst |
| CN104549465A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Heavy aromatics light catalyst for high-yield production of xylene and preparation method of catalyst |
| CN106582779A (en) * | 2015-10-15 | 2017-04-26 | 中国石油化工股份有限公司 | Polycyclic aromatic hydrocarbon ring-opening catalyst and preparation method thereof |
| CN106582791A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Catalyst for producing ethylbenzene from benzene and ethane |
| CN109126863A (en) * | 2018-10-08 | 2019-01-04 | 中海油天津化工研究设计院有限公司 | A kind of condensed-nuclei aromatics adds the preparation method of the porous Pd composite membrane of hydrogen production mononuclear aromatics |
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| CN104549473A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Catalyst for converting sulphur-containing polycyclic aromatic hydrocarbon into mononuclear aromatic and preparation method of catalyst |
| CN104549469A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Reproducible catalyst for converting polycyclic aromatic hydrocarbon into monocyclic aromatic hydrocarbon and preparation method of reproducible catalyst |
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| CN106582791A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Catalyst for producing ethylbenzene from benzene and ethane |
| CN106582791B (en) * | 2015-10-14 | 2019-04-12 | 中国石油化工股份有限公司 | Catalyst for benzene and ethane ethylbenzene |
| CN106582779A (en) * | 2015-10-15 | 2017-04-26 | 中国石油化工股份有限公司 | Polycyclic aromatic hydrocarbon ring-opening catalyst and preparation method thereof |
| CN106582779B (en) * | 2015-10-15 | 2019-10-11 | 中国石油化工股份有限公司 | Polycyclic aromatic hydrocarbon ring opening catalyst and preparation method thereof |
| CN109126863A (en) * | 2018-10-08 | 2019-01-04 | 中海油天津化工研究设计院有限公司 | A kind of condensed-nuclei aromatics adds the preparation method of the porous Pd composite membrane of hydrogen production mononuclear aromatics |
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