CN105732251A - Method of catalytic conversion to produce aromatic hydrocarbon from methanol - Google Patents

Method of catalytic conversion to produce aromatic hydrocarbon from methanol Download PDF

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Publication number
CN105732251A
CN105732251A CN201410768814.XA CN201410768814A CN105732251A CN 105732251 A CN105732251 A CN 105732251A CN 201410768814 A CN201410768814 A CN 201410768814A CN 105732251 A CN105732251 A CN 105732251A
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zsm
methanol
aromatic hydrocarbons
molecular sieve
converts
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CN105732251B (en
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徐亚荣
徐新良
冯丽梅
展江宏
许磊
贺春梅
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China Petroleum and Natural Gas Co Ltd
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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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • 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
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/40—Ethylene production

Abstract

The invention relates to a method of catalytic conversion to produce aromatic hydrocarbon from methanol and mainly relates to a method of producing the aromatic hydrocarbon through a fixed bed two-step method. The method includes the following steps: in a first-section reaction, with methanol as a raw material and a ZSM-5/ZSM-11 eutectic molecular sieve as catalyst, producing a first-section reaction product mainly including ethylene, propylene and C4 olefins, performing condensation separation to the first section reaction product, feeding a gas-phase product containing low-carbon olefins into a second-section reactor, and preparing the aromatic hydrocarbon in the presence of a modified ZSM-5 molecular sieve catalyst. In a first first-section reactor, methanol is converted into the product mainly including the low-carbon olefins, which are subjected to aromatization in the second-section reactor to obtain the aromatic hydrocarbon. The method effectively increases the selectivity and yield of conversion of the methanol into the aromatic hydrocarbon.

Description

Methanol oxidation converts the method producing aromatic hydrocarbons
Technical field
The present invention relates to a kind of method with methanol for raw material production aromatic hydrocarbons.
Background technology
Methanol is one of primary product of Coal Chemical Industry, and along with the development of Coal Chemical Industry, the methanol output on market will increase sharply, and the development of methanol industry is had great importance by active development Downstream Products of Methanol.Preparing olefin by conversion of methanol (MTO) is the direction that methanol converts, at present, the passed years of researches of domestic bigization, develop the Technology of the MTO with independent intellectual property right, this technology comes into Industrial demonstration experimental stage.Aromatic hydrocarbons is the basic chemical industry raw material that modern chemical industry demand is only second to ethylene, propylene.Methanol aromatic hydrocarbons (MTA) technology is advantageous for promoting the new technique that China develops with the new industry that coal is raw material substitution Petroleum Production petroleum chemicals.
The industrialization technology of methanol aromatic hydrocarbons still belongs to blank.Aromatization of methanol is under the effect selecting type molecular sieve catalyst, generates alkene through methanol dehydration, and alkene, then through processes such as polymerization, alkylation, cracking, isomerization, cyclisation, hydrogen migrations, is eventually converted into the process of aromatic hydrocarbons.Final products are relevant with the selection of selecting property catalyst, and product is based on xylol.This is the process of a deep conversion, and aromatic device is required height；Technically catalysqt deactivation degree is difficult to grasp simultaneously.
Domestic have been reported about the catalyst of methanol conversion for preparing arene and the research of Technology, Chinese Academy of Sciences's Shanxi coalification patent CN200610012703.1 disclose technique and the method for preparing catalyst of a kind of methanol conversion for preparing arene, with ZSM-5 molecular sieve for catalyst, load La2O3、GaO2Etc. metal oxide modified, adopting the conversion process of two sections of fixing beds, first paragraph converts the product based on aromatic hydrocarbons, and after condensation, a small amount of lower carbon number hydrocarbons enters second stage reactor and continues reaction.A kind of method that the patent CN201010261717.3 of Sinopec Shanghai Petroleum Chemical Engineering Institute discloses methanol conversion for preparing arene, the feature of this patent adopts a segment process by methanol conversion for preparing arene, with ZSM-5 and ZSM-11 or β H molecular sieve mixture for catalyst, load La2O3、P2O5Deng oxide modifying, in course of reaction, C1-C4 product assay is high, and the productivity of aromatic hydrocarbons is relatively low.
By the present invention and Patents relative analysis, both adopt catalyst and technique different.The present invention provides a kind of methanol to convert the technique of high selectivity aromatic hydrocarbons, adopts fixing bed two-stage method to produce aromatic hydrocarbons, and one section of reaction is with methanol for raw material, with the molecular sieve of ZSM-5 and ZSM-11 eutectic for catalyst, and loading ZnO, La2O3、CeO2Etc. metal oxide modified, adopting fixing bed two-stage method to produce aromatic hydrocarbons, change into low-carbon alkene for primary product at first paragraph reactor methanol, low-carbon alkene becomes aromatic hydrocarbons at second segment reactor aromatization.
Showing through document relative analysis, the research of the domestic catalyst about methanol conversion for preparing arene and Technology is it has been reported that but adopt the methanol aromatics process technology of same catalyst to have no report with the present invention.
Summary of the invention
The present invention provides the new technology converting high selectivity aromatic hydrocarbons with coal-based methanol for raw material, the purpose of this technique is to provide a Non oil-based route and produces the route of basic organic chemical industry raw material, the degree of dependence relying on naphtha reforming to produce aromatic hydrocarbons can be reduced, reduce the interdependency that China's oil is external, improve the strategic security of the energy, resource.The advantage that this technique behaviour does mild condition, production cost is low, the market competitiveness is strong.
For achieving the above object, the present invention provides a kind of methanol oxidation to convert the method producing aromatic hydrocarbons, comprises the steps:
A, the fixing bed two-stage method explained hereafter aromatic hydrocarbons of employing, one section of reaction is with methanol for raw material, with ZSM-5 and ZSM-11 eutectic molecular sieve for catalyst, is operating pressure 0.1-1.0MPa, reaction temperature 380-480 DEG C, air speed 0.5-6.0h-1Under, prepare based on ethylene, propylene, C4 alkene one section of product；
B, one section of product is carried out condensation separation, the gas-phase product containing low-carbon alkene is sent in second stage reactor；The operation pressure of second stage reactor is 0.1-1.0MPa, and reaction temperature is 360-480 DEG C, and air speed is 100-5000h-1, under ZSM-5 Type Zeolites agent exists, prepare aromatic hydrocarbons.
Methanol oxidation of the present invention converts the method producing aromatic hydrocarbons, the preferred 0.06-18 of the mass ratio of ZSM-5 and ZSM-11 in the eutectic molecular sieve of wherein said step A.
Methanol oxidation of the present invention converts the method producing alkene, the preferred Al of the mass ratio of each composition in wherein said eutectic molecular sieve2O3:SiO2:TBA+:Seeds:H2O=60～700:1:0.08～0.18:0.5～5:10～20, wherein Seeds represents the crystal seed of ZSM-5 structure, TBA+Represent the alkali liquor of tetrabutyl ammonium bromide.
Methanol oxidation of the present invention converts the method producing aromatic hydrocarbons, the modified zsm-5 zeolite of the preferred silica alumina ratio 30-80:1 of modified zsm-5 zeolite in wherein said step B.
Methanol oxidation of the present invention converts the method producing aromatic hydrocarbons, and the modified zsm-5 zeolite in wherein said step B is by acid-alkali treatment, dry, roasting back loading ZnO, La2O3、CeO2Be modified Deng metal-oxide, load capacity in molecular sieve carrier, ZnO preferred 0.5-3 mass %, La2O3Preferred 0.1-1.5 mass %, CeO2Preferred 0.1-1.5 mass %.
Methanol oxidation of the present invention converts the method producing aromatic hydrocarbons, the preferred 0.1-0.5MPa of operation pressure in wherein said step A.
Methanol oxidation of the present invention converts the method producing aromatic hydrocarbons, the preferred 0.1-0.5MPa of operation pressure in wherein said step B.
Adopting fixing bed two-stage method to produce aromatic hydrocarbons, change into low-carbon alkene for primary product at first paragraph reactor methanol, low-carbon alkene becomes aromatic hydrocarbons at second segment reactor aromatization.Adopt this technique can be effectively improved methanol carbon and be converted into selectivity and the yield of aromatic hydrocarbons.Low-carbon alkene (C2, C3, C4 alkene) content about 80% after one section of conversion provided by the present invention, the C of 13-15%5+Liquid product, all the other are the alkane of C1-C4.The gas-phase product of one section is through two-stage nitration aromatization, and the selectivity of aromatic hydrocarbons reaches more than the 80% of liquid product, adopts two sections of conversion process to be converted into low-carbon alkene aromatization again by methanol, it is thus achieved that the selectivity of target product aromatic hydrocarbons more than 80%, C5+Liquid yield reaches more than 32%, and selectivity and the yield of aromatic hydrocarbons increase substantially.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in further detail, but the present invention is not by the restriction of following embodiment.The change of any design without departing from the present invention and category, is within the scope of the present invention.
Embodiment 1:
With methanol for raw material, first paragraph reactor loading catalyst 6g, catalyst adopts the mass ratio 1:1 of ZSM-5 and ZSM-11, controls reaction pressure 0.1MPa, reaction temperature 475 DEG C, air speed 2h-1The ZSM-5 molecular sieve catalyst that the filling of second segment reactor is modified, modified ZSM-5 molecular sieve adopts silica alumina ratio 50 molecular sieve to carry out acid-alkali treatment, dry, roasting back loading 2%ZnO, reaction pressure 0.1MPa, reaction temperature 400 DEG C, methanol forms such as table 1, table 2 through the liquid and gas product of first stage reactor and second stage reactor.
The liquid product composition of table 1 two reactor
2 one sections of table, second stage reactor gas-phase product composition
Embodiment 2:
With methanol for raw material, first paragraph reactor loading catalyst 10g, catalyst adopts the mass ratio 2:1 of ZSM-5 and ZSM-11, controls reaction pressure 0.5MPa, reaction temperature 450 DEG C, air speed 2h-1The ZSM-5 molecular sieve catalyst that the filling of second segment reactor is modified, modified ZSM-5 molecular sieve adopts silica alumina ratio 50 molecular sieve to carry out acid-alkali treatment, dry, roasting back loading 2%ZnO, reaction pressure 0.5MPa, reaction temperature 400 DEG C, methanol forms such as table 3, table 4 through the liquid and gas product of first stage reactor and second stage reactor.
The liquid product composition of table 3 two reactor
4 one sections of table, second stage reactor gas-phase product composition
Embodiment 3:
With methanol for raw material, with methanol for raw material, first paragraph reactor loading catalyst 10g, catalyst adopts the mass ratio 2:1 of ZSM-5 and ZSM-11, controls reaction pressure 0.1MPa, reaction temperature 475 DEG C, air speed 2h-1The ZSM-5 molecular sieve catalyst that the filling of second segment reactor is modified, modified ZSM-5 molecular sieve adopts silica alumina ratio 50 molecular sieve to carry out acid-alkali treatment, dry, roasting back loading 1%ZnO reaction pressure 0.1MPa, reaction temperature 360 DEG C, methanol forms such as table 5, table 6 through the liquid and gas product of first stage reactor and second stage reactor.
The liquid product composition of table 5 two reactor
The gas-phase product composition of table 6 two reactor
Methane Ethylene Ethane Propylene Propane Iso-butane N-butene Normal butane Anti-butylene Maleic
7.88 4.25 1.49 14.00 16.4 28.66 12.20 7.57 4.87 2.63
Embodiment 4:
With methanol for raw material, first paragraph reactor loading catalyst 10g, catalyst adopts the mass ratio 1:1 of ZSM-5 and ZSM-11, controls reaction pressure 0.5MPa, reaction temperature 470 DEG C, air speed 1.5h-1The ZSM-5 molecular sieve catalyst that the filling of second segment reactor is modified, modified ZSM-5 molecular sieve adopts silica alumina ratio 80 molecular sieve to carry out acid-alkali treatment, dry, roasting back loading 1%ZnO, reaction pressure 0.5MPa, reaction temperature 400 DEG C, catalyst runs 200 hours, and methanol forms such as table 7, table 8 through the liquid and gas product of first stage reactor and second stage reactor.
The liquid product composition of table 7 two reactor
The gas-phase product composition of table 8 two reactor
Methane Ethylene Ethane Propylene Propane Iso-butane N-butene Normal butane Anti-butylene Maleic
7.88 4.25 1.49 14.00 16.4 28.66 12.20 7.57 4.87 2.63
Embodiment 5:
With methanol for raw material, first paragraph reactor loading catalyst 10g, catalyst adopts the mass ratio 2:1 of ZSM-5 and ZSM-11, controls reaction pressure 0.2MPa, reaction temperature 450 DEG C, air speed 2h-1The ZSM-5 molecular sieve catalyst that the filling of second segment reactor is modified, modified ZSM-5 molecular sieve adopts silica alumina ratio 80 molecular sieve to carry out acid-alkali treatment, dry, roasting back loading 2%ZnO, reaction pressure 0.2MPa, reaction temperature 400 DEG C, catalyst runs 360 hours, and methanol forms such as table 9, table 10 through the liquid and gas product of first stage reactor and second stage reactor.
The liquid product composition of table 9 two reactor
The gas-phase product composition of table 10 two reactor
Methane Ethylene Ethane Propylene Propane Iso-butane N-butene Normal butane Anti-butylene Maleic
7.88 4.25 1.49 14.00 16.4 28.66 12.20 7.57 4.87 2.63

Claims (8)

1. methanol oxidation converts the method producing aromatic hydrocarbons, comprises the steps:
A, the fixing bed two-stage method explained hereafter aromatic hydrocarbons of employing, one section of reaction is with methanol for raw material, with ZSM-5 and ZSM-11 eutectic molecular sieve for catalyst, is operating pressure 0.1-1.0MPa, reaction temperature 380-480 DEG C, air speed 0.5-6.0h-1Under, prepare based on ethylene, propylene, C4 alkene one section of product；
B, one section of product is carried out condensation separation, the gas-phase product containing low-carbon alkene is sent in second stage reactor；The operation pressure of second stage reactor is 0.1-1.0MPa, and reaction temperature is 360-480 DEG C, and air speed is 100-5000h-1, under ZSM-5 Type Zeolites agent exists, prepare aromatic hydrocarbons.
2. methanol oxidation according to claim 1 converts the method producing aromatic hydrocarbons, it is characterised in that in the eutectic molecular sieve of described step A, the mass ratio of ZSM-5 and ZSM-11 is 0.06-18.
3. methanol oxidation according to claim 2 converts the method producing alkene, it is characterised in that in described eutectic molecular sieve, the mass ratio of each composition is Al2O3:SiO2:TBA+:Seeds:H2O=60～700:1:0.08～0.18:0.5～5:10～20, wherein Seeds represents the crystal seed of ZSM-5 structure, TBA+Represent the alkali liquor of tetrabutyl ammonium bromide.
4. the methanol oxidation according to claims 1 to 3 any one converts the method producing aromatic hydrocarbons, it is characterised in that the modified zsm-5 zeolite in described step B is the modified zsm-5 zeolite of silica alumina ratio 30-80:1.
5. the methanol oxidation according to claims 1 to 3 any one converts the method producing aromatic hydrocarbons, it is characterised in that the modified zsm-5 zeolite in described step B is by acid-alkali treatment, dry, roasting back loading ZnO, La2O3、CeO2Being modified Deng metal-oxide, load capacity is in molecular sieve carrier, ZnO:0.5-3 mass %, La2O3: 0.1-1.5 mass %, CeO2: 0.1-1.5 mass %.
6. methanol oxidation according to claim 4 converts the method producing aromatic hydrocarbons, it is characterised in that the modified zsm-5 zeolite in described step B is by acid-alkali treatment, dry, roasting back loading ZnO, La2O3、CeO2Being modified Deng metal-oxide, load capacity is in molecular sieve carrier, ZnO:0.5-3 mass %, La2O3: 0.1-1.5 mass %, CeO2: 0.1-1.5 mass %.
7. methanol oxidation according to claim 1 converts the method producing aromatic hydrocarbons, it is characterised in that the operation pressure in described step A is 0.1-0.5MPa.
8. methanol oxidation according to claim 1 converts the method producing aromatic hydrocarbons, it is characterised in that the operation pressure in described step B is 0.1-0.5MPa.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106542947A (en) * 2016-10-14 2017-03-29 中国科学院山西煤炭化学研究所 A kind of technique of fixed bed methanol aromatic hydrocarbons
CN106866328A (en) * 2017-01-16 2017-06-20 厦门大学 A kind of method of methyl alcohol high selectivity aromatic hydrocarbons
CN111097337A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Zoned fluidized bed reaction-regeneration device and process for preparing aromatic hydrocarbon through methanol conversion

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CN102078819A (en) * 2009-11-26 2011-06-01 中国石油化工股份有限公司 Light hydrocarbon aromatization catalyst and preparation method thereof
CN102153105A (en) * 2010-12-31 2011-08-17 华东师范大学 Method for preparing MFI/MEL (Mobil Fifth/Mobil Eleven) eutectic molecular sieve
CN102775261A (en) * 2012-07-23 2012-11-14 李小燕 Multifunctional methanol processing method and apparatus
CN103539153A (en) * 2012-07-12 2014-01-29 中国石油化工股份有限公司 Preparation method of nano hierarchical-pore ZSM-11/ZSM-5 eutectic zeolite
CN103694077A (en) * 2013-12-03 2014-04-02 浙江大学 Reaction technology for production of propylene and coproduction of high-octane value gasoline components

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US3911041A (en) * 1974-09-23 1975-10-07 Mobil Oil Corp Conversion of methanol and dimethyl ether
CN102078819A (en) * 2009-11-26 2011-06-01 中国石油化工股份有限公司 Light hydrocarbon aromatization catalyst and preparation method thereof
CN102153105A (en) * 2010-12-31 2011-08-17 华东师范大学 Method for preparing MFI/MEL (Mobil Fifth/Mobil Eleven) eutectic molecular sieve
CN103539153A (en) * 2012-07-12 2014-01-29 中国石油化工股份有限公司 Preparation method of nano hierarchical-pore ZSM-11/ZSM-5 eutectic zeolite
CN102775261A (en) * 2012-07-23 2012-11-14 李小燕 Multifunctional methanol processing method and apparatus
CN103694077A (en) * 2013-12-03 2014-04-02 浙江大学 Reaction technology for production of propylene and coproduction of high-octane value gasoline components

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106542947A (en) * 2016-10-14 2017-03-29 中国科学院山西煤炭化学研究所 A kind of technique of fixed bed methanol aromatic hydrocarbons
CN106542947B (en) * 2016-10-14 2019-04-02 中国科学院山西煤炭化学研究所 A kind of technique of fixed bed methanol aromatic hydrocarbons
CN106866328A (en) * 2017-01-16 2017-06-20 厦门大学 A kind of method of methyl alcohol high selectivity aromatic hydrocarbons
CN106866328B (en) * 2017-01-16 2019-12-10 厦门大学 Method for preparing aromatic hydrocarbon with high selectivity by using methanol
CN111097337A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Zoned fluidized bed reaction-regeneration device and process for preparing aromatic hydrocarbon through methanol conversion
CN111097337B (en) * 2018-10-25 2022-04-05 中国石油化工股份有限公司 Zoned fluidized bed reaction-regeneration device and process for preparing aromatic hydrocarbon through methanol conversion

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