CN106608783B - Method for preparing dimethylbenzene from methanol - Google Patents
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- C07—ORGANIC CHEMISTRY
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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
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
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- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
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Abstract
The invention relates to a method for preparing dimethylbenzene from methanol, which mainly solves the problem of low content of p-dimethylbenzene in an aromatic hydrocarbon product prepared from methanol in the prior art. The invention adopts the following steps: 1) the methanol raw material I is converted into a reaction product mainly containing aromatic hydrocarbon in an aromatization reactor; 2) separating the reaction product into a gas phase, an oil phase and a water phase by a three-phase separator; 3) returning the gas phase after removing hydrogen and methane to the aromatization reactor; 4) the oil phase is separated into a non-aromatic material flow and an aromatic material flow in a separation unit I; 5) the aromatic hydrocarbon material flow is separated into a toluene material flow, a xylene material flow, a mixed material flow of benzene, carbon, nine and ten, and material flows of more than eleven carbon in a separation unit II; 6) the benzene carbon nine carbon ten mixed material flow is sent into a transalkylation reactor to be converted into a transalkylation product; 7) the technical scheme that the toluene material flow and the methanol raw material II are sent into a toluene-methanol methylation reactor to be converted into a methylation product better solves the problems and can be used in the industrial production of preparing aromatic hydrocarbon from methanol.
Description
Technical Field
The invention relates to a method for preparing dimethylbenzene from methanol.
Technical Field
Aromatic hydrocarbons, in particular the light aromatic hydrocarbons BTX (benzene, toluene, xylene), are important basic organic chemicals, second only to ethylene and propylene in terms of yield and scale. Among the aromatic hydrocarbons, para-xylene is a product with high added value. Para-xylene is an important feedstock for the polyester industry, primarily for the production of Purified Terephthalic Acid (PTA) or purified dimethyl terephthalate (DMT), from which Polyester (PET) is produced. In recent years, polyester industry in China is rapidly developed, the supply of paraxylene is short, and the situation of supply shortage of paraxylene is alleviated along with the energy expansion of the conventional paraxylene device and the capacity release of a newly-built device. However, as the U.S. shale gas production increases, the trend toward lighter feedstocks for pyrolysis units is more pronounced, resulting in a decrease in worldwide aromatics production, and thus there is still a potential for a worldwide shortage of para-xylene. On the other hand, the petroleum supply is increasingly tense, the crude oil price is high, and the cost pressure of domestic petrochemical enterprises is great. By combining the national conditions of rich coal resources and higher oil dependence in China, the development of the coal chemical industry with the advantage of raw material price is very urgent. The technology for preparing aromatic hydrocarbon from methanol is just one of the new coal chemical technologies developed in recent years in China.
The technology for preparing aromatic hydrocarbon from methanol is a process for producing aromatic hydrocarbon by the steps of dehydrogenation, cyclization and the like under the catalytic action of a bifunctional (acidic and dehydrogenation) active catalyst by taking methanol as a raw material. In the aromatization process, aromatic hydrocarbons such as benzene, toluene and xylene are generated, and by-products comprise hydrocarbons such as methane, ethylene and propylene and hydrogen. At present, except for the completion of industrial tests by the FMTA technology of Qinghua university in China, other technologies are still in the stage of small tests and pilot tests.
Patent CN101823929 of the university of qinghua discloses a system and a process for preparing aromatic hydrocarbon by converting methanol or dimethyl ether. The raw material methanol or dimethyl ether is firstly reacted in a raw material aromatization reactor, and the product after the reaction is separated into gas-phase light hydrocarbon, oil phase mainly containing aromatic hydrocarbon and water by a three-phase separation unit. In order to improve the selectivity and yield of aromatic hydrocarbon, the patent provides three technical schemes. In the first embodiment, C is separated from the reaction product2And the non-aromatic hydrocarbons are firstly subjected to aromatization reaction in the low-carbon olefin aromatization reactor, then the aromatic hydrocarbons and the light hydrocarbons are separated, then the hydrogen methane product is separated from the light hydrocarbons, the rest light hydrocarbons are sent into the low-carbon hydrocarbon aromatization reactor, and the product returns to the three-phase separation unit. In addition, benzene, toluene, and part C9+ hydrocarbons are sent to an aromatics disproportionation reactor to produce C8 aromatics, which are also returned to the three-phase separation unit. Hydrogen, methane, mixed C8Aromatic hydrocarbons and fraction C9+ hydrocarbons as product export system. The process scheme comprises four reactors, and the flow is relatively complex. The second solution of the patent provides a simplified process flow, C2After separating out the hydrogen and methane products from the non-aromatic hydrocarbon, sending the hydrogen and methane products into a low-carbon hydrocarbon aromatization reactor, and returning the reaction products to a three-phase separation unit, namely not arranging the low-carbon olefin aromatization reactor. The third technical proposal of the patent is further simplified on the basis of the former technical proposal, and the benzene, the toluene and part C are separated from the oil phase aromatic hydrocarbon9The hydrocarbons are directly returned to the raw material aromatization reactor, and an aromatic hydrocarbon disproportionation reactor is omitted. The third technical proposal of the patent can obtain higher yield of the aromatic hydrocarbon. According to the examples, under preferred operating conditions, C is mixed8The carbon-based yield of aromatic hydrocarbons was 81.96 WT%. However, this patent does not disclose the yield of xylenes, especially para-xylene, in aromatic hydrocarbons.
Patent CN200910090002 discloses a method for preparing ethylene and propylene and co-producing p-xylene by methanol/dimethyl ether conversion. The method adopts a silanization modified molecular sieve catalyst, the methanol is converted to prepare ethylene and propylene, and simultaneously the coproduction of aromatic hydrocarbon mainly comprises p-xylene, the total selectivity of ethylene, propylene and p-xylene in hydrocarbon products is more than 80 WT%, and the selectivity of p-xylene in xylene isomers is more than 99 WT%. The selectivity of p-xylene in aromatic hydrocarbon in the method is high, but the total yield of the aromatic hydrocarbon is low and is less than 25 WT%.
The prior art has the problem of low selectivity of p-xylene in aromatic hydrocarbon, and the invention aims to solve the problem.
Disclosure of Invention
The invention aims to solve the technical problem of low content of paraxylene in aromatic hydrocarbon products prepared from methanol in the prior art, and provides a novel method for preparing dimethylbenzene from methanol. The device has the advantages of high aromatic hydrocarbon yield, high p-xylene content in aromatic hydrocarbon and easy separation of p-xylene.
In order to solve the problems, the technical scheme adopted by the invention is as follows: a method for preparing xylene from methanol, comprising the steps of: 1) the methanol raw material I is converted into a reaction product mainly containing aromatic hydrocarbon in an aromatization reactor; 2) separating the reaction product into a gas phase, an oil phase and a water phase by a three-phase separator; 3) returning the gas phase after removing hydrogen and methane to the aromatization reactor; 4) the oil phase is separated into a non-aromatic material flow and an aromatic material flow in a separation unit I; 5) the aromatic hydrocarbon material flow is separated into a toluene material flow, a xylene material flow, a mixed material flow of benzene, carbon, nine and ten, and material flows of more than eleven carbon in a separation unit II; 6) the benzene carbon nine carbon ten mixed material flow is sent into a transalkylation reactor to be converted into a transalkylation product; 7) returning the transalkylation product to the separation unit II; 8) feeding the toluene material flow and the methanol raw material II into a toluene methanol methylation reactor to be converted into a methylation product; 9) the methylated product is returned to the three-phase separator.
In the technical scheme, the aromatization reactor is a fluidized bed reactor, aromatization reaction is carried out on a ZSM-5 molecular sieve catalyst, the reaction temperature is 450-550 ℃, and the reaction pressure is 0.1-0.5 MPAG.
In the technical scheme, the transalkylation reactor is a fixed bed reactor, transalkylation reaction is carried out on a solid acid catalyst, a metal oxide catalyst or a molecular sieve catalyst, preferably a bismuth-containing large-pore zeolite catalyst, the reaction temperature is 300-450 ℃, and the reaction pressure is 1-5 MPAG.
In the technical scheme, the toluene-methanol methylation reactor is a fixed bed reactor, the methylation reaction is carried out under the action of a modified ZSM-5 molecular sieve catalyst, the reaction temperature is 300-500 ℃, and the reaction pressure is 0-3 MPAG.
In the technical scheme, the molar ratio of the toluene material flow to the methanol raw material II is 4: 1-1: 2.
In the above technical scheme, the selectivity of p-xylene in the methylated product is not less than 80 WT%.
In the above technical solution, the xylene content in the transalkylation product is not less than 10 WT%.
By adopting the method, after light hydrocarbons in the methanol aromatization reaction product, including ethylene, propylene, ethane, propane and the like, are separated from the three-phase separator, methane and hydrogen are removed firstly and are extracted as products, and the rest hydrocarbons return to the methanol aromatization reactor for further aromatization, thereby improving the total yield of aromatic hydrocarbon. Since the conversion of alkanes in the aromatization reaction is low, a partial discharge system is required in order to avoid accumulation in the system.
By adopting the method, the toluene and the methanol in the methanol aromatization reaction product are further subjected to methylation reaction to generate the paraxylene and the water. The conversion rate of the reaction toluene is 20-50%, but the selectivity of p-xylene in the methylation product is high and is more than 80%. Thus by returning the methylated product to the three-phase separator, the content of p-xylene in the separated oil phase is at least 10 WT% higher than that in the case where no methylation reactor is provided, and the separated water phase contains unreacted methanol and is recovered in a methanol recovery column, thereby increasing the overall methanol conversion of the plant.
By adopting the method, benzene and carbon nonadeca-arene react in the transalkylation reactor to generate a transalkylation product with toluene and carbon octa-arene as the main components. The generated toluene is separated from the oil phase through rectification separation and is sent to a methylation reactor to generate a methylation product with high p-xylene content. The yield of the xylene is further improved by converting the carbon nine and ten into the carbon octa-arene.
By adopting the method, the content of the p-xylene in the mixed xylene stream separated by the aromatic hydrocarbon rectification separation unit is not less than 60 WT%. As is known, the high p-xylene content in the xylene stream is beneficial to separating p-xylene by means of crystallization separation and the like, and the energy consumption for separation is low. Because light hydrocarbon, benzene, toluene, carbon nine carbon ten and other components in the aromatization reaction product are further converted into the target product xylene, the yield of the xylene is improved, the yield of the xylene is more than 80 WT%, and a better technical effect is achieved.
Drawings
FIG. 1 is a schematic flow diagram of the process of the present invention.
In FIG. 1, 1 is a methanol feedstock I; 2 is the aromatization reactor feed; 3 is a reaction product; 4 is a gas phase; 5 is hydrogen methane; 6 is circulating light hydrocarbon; 7 is an oil phase; 8 is a water phase; 9 is a non-aromatic stream; 10 is an aromatic hydrocarbon stream; 11 is the separation unit II feed; 12 is a toluene stream; 13 is a xylene stream; 14 is a stream of carbon eleven and above; 15 is a benzene carbon nine carbon ten mixed material flow; 16 is a transalkylation product; 17 is a methanol raw material II; 18 is a methylation product; a is an aromatization reactor; b is a three-phase separator; c is a gas separation unit; d is a separation unit I; e is a separation unit II; f is a transalkylation reactor; g is a toluene methanol methylation reactor.
The methanol raw material I is converted into a reaction product mainly containing aromatic hydrocarbon in an aromatization reactor; separating the reaction product into a gas phase, an oil phase and a water phase by a three-phase separator; returning the gas phase after removing hydrogen and methane to the aromatization reactor; the oil phase is separated into a non-aromatic material flow and an aromatic material flow in a separation unit I; the aromatic hydrocarbon material flow is separated into a toluene material flow, a xylene material flow, a mixed material flow of benzene, carbon, nine and ten, and material flows of more than eleven carbon in a separation unit II; the benzene carbon nine carbon ten mixed material flow is sent into a transalkylation reactor to be converted into a transalkylation product; returning the transalkylation product to the separation unit II; feeding the toluene material flow and the methanol raw material II into a toluene methanol methylation reactor to be converted into a methylation product; the methylated product is returned to the three-phase separator.
The present invention will be further illustrated by the following examples, but is not limited to these examples.
Detailed Description
[ example 1 ]
The methanol raw material I enters an aromatization reactor to carry out aromatization reaction under the action of a ZSM-5 molecular sieve catalyst, the reaction temperature is 460 ℃, the reaction pressure is 0.1MPAG, and the weight space velocity is 0.3/HR. The reaction product is cooled to 40 ℃ and then sent into a three-phase separator to be separated into a gas phase, an oil phase and a water phase. Wherein the gas phase is sent into a demethanizer, methane and hydrogen are separated from the top of the tower and discharged out of the system, and low-carbon hydrocarbons above the carbon dioxide in the tower bottom are used as circulating light hydrocarbons and returned to the aromatization reactor. An oil phase of the three-phase separator is separated into an aromatic hydrocarbon material flow and a non-aromatic hydrocarbon material flow in a separation unit I by adopting an aromatic hydrocarbon extraction method, and the non-aromatic hydrocarbon material flow is discharged out of the system. The aromatic hydrocarbon material flow is sent to a separation unit II for further separation into benzene, toluene, xylene, hydrocarbons with nine carbon atoms, ten carbon atoms, eleven carbon atoms and above hydrocarbons. And C eleven and above material flows are discharged from the system. The toluene material flow and the methanol raw material II are mixed according to the molar ratio of 1:2 and then are sent into a toluene methanol methylation reactor, the reaction temperature is 300 ℃, the reaction pressure is 0.1MPAG, and the weight space velocity is 7/HR. The toluene conversion for the toluene methylation reaction was 47.8% with a selectivity to para-xylene of 81.5%. The methylated product returns to a three-phase separator to separate water and aromatic hydrocarbon. And the unreacted methanol in the methanol raw material II is dissolved in water, recovered by a methanol recovery tower and returned to the aromatization reactor. And mixing the benzene and the carbon nine-carbon ten components separated from the separation unit II to form a benzene carbon nine-carbon ten mixed material flow, and sending the mixed material flow into a transalkylation reactor. The transalkylation reaction temperature was 325 deg.C, the reaction pressure was 1.5MPAG, the weight space velocity was 0.8/HR, and the xylene selectivity in the transalkylation product was 13.1%. The transalkylation product is returned to separation unit II. The xylene stream from separation unit II was withdrawn from the system as product with a para-xylene mass content of 62.1%. The yield of the xylene carbon group in the process is 83.3 percent, and the yield of the p-xylene carbon group is 51.7 percent.
[ example 2 ]
The process conditions were varied for each reactor according to the procedure described in example 1. The aromatization reaction temperature is 500 ℃, the reaction pressure is 0.25MPAG, and the weight space velocity is 0.15/HR. The toluene material flow and the methanol raw material II are mixed according to the molar ratio of 1:1 and then are sent into a toluene methanol methylation reactor, the reaction temperature is 400 ℃, the reaction pressure is 1MPAG, and the weight space velocity is 2/HR. The toluene conversion of the toluene methylation reaction was 30.3% and the selectivity to para-xylene was 82.3%. The transalkylation reaction temperature was 380 deg.C, the reaction pressure was 3MPAG, the weight space velocity was 2/HR, and the xylene selectivity in the transalkylation product was 16.2%. The mass content of p-xylene in the xylene stream was 62.5%. The yield of the xylene carbon group in the process is 84.2 percent, and the yield of the p-xylene carbon group is 52.6 percent.
[ example 3 ]
The process conditions were varied for each reactor according to the procedure described in example 1. The aromatization reaction temperature is 540 ℃, the reaction pressure is 0.4MPAG, and the weight space velocity is 0.15/HR. The toluene material flow and the methanol raw material II are mixed according to the molar ratio of 1:2 and then are sent into a toluene methanol methylation reactor, the reaction temperature is 500 ℃, the reaction pressure is 3MPAG, and the weight space velocity is 2/HR. The toluene conversion of the toluene methylation reaction was 28.3% and the selectivity to para-xylene was 91.2%. The transalkylation reaction temperature was 420 deg.C, the reaction pressure was 3MPAG, the weight space velocity was 3/HR, and the xylene selectivity in the transalkylation product was 18.6%. The mass content of p-xylene in the xylene stream was 65.7%. The yield of the xylene carbon group in the process is 82.7 percent, and the yield of the p-xylene carbon group is 54.3 percent.
[ example 4 ]
The process conditions were varied for each reactor according to the procedure described in example 1. The aromatization reaction temperature is 500 ℃, the reaction pressure is 0.15MPAG, and the weight space velocity is 0.1/HR. The toluene material flow and the methanol raw material II are mixed according to the molar ratio of 1:2 and then are sent into a toluene methanol methylation reactor, the reaction temperature is 300 ℃, the reaction pressure is 0.3MPAG, and the weight space velocity is 2/HR. The toluene conversion of the toluene methylation reaction was 36.2% and the selectivity to para-xylene was 81.3%. The transalkylation reaction temperature was 420 deg.C, the reaction pressure was 3MPAG, the weight space velocity was 3/HR, and the xylene selectivity in the transalkylation product was 18.6%. The mass content of p-xylene in the xylene stream was 62.3%. The yield of the xylene carbon group in the process is 83.5 percent, and the yield of the p-xylene carbon group is 52.0 percent.
[ COMPARATIVE EXAMPLE 1 ]
Patent CN101823929B discloses a system and process for preparing aromatic hydrocarbons by converting methanol or dimethyl ether. The yield of carbon base of mixed C8 is 73-81.9% when the method of the patent is used for preparing aromatic hydrocarbon.
Comparing the xylene carbon based yields of examples 1 to 4 and comparative example 1, it is clear that a higher xylene carbon based yield can be obtained by the method of the present invention for two reasons. Firstly, more carbon nonadeca-arene is converted into dimethylbenzene in a transalkylation reactor by adopting the method; secondly, by adopting the method of the invention, the methyl utilization rate of the methanol in the toluene-methanol methylation reaction is higher than that of the methanol aromatization reaction, namely more methanol is converted into methyl rather than light hydrocarbons.
[ COMPARATIVE EXAMPLE 2 ]
The procedure of example 1 was followed essentially by replacing the toluene methylation reactor of the present invention with a toluene disproportionation reactor. In theory, toluene disproportionation reaction can obtain one benzene molecule and one xylene molecule from two toluene molecules, and in practice, the benzene/xylene molar ratio in the reaction product is 1.3, which is due to the presence of other side reactions, resulting in the conversion of a small amount of toluene into light hydrocarbons and hydrocarbons with carbon nine and above. The benzene generated by the toluene shape selective disproportionation reaction is used as the raw material of benzene carbon nine carbon ten alkyl transfer reaction, and is merged with carbon nine carbon ten hydrocarbons generated by the reaction of preparing aromatic hydrocarbon from methanol, and then the merged mixture is converted into xylene and toluene in an alkyl transfer reactor, wherein the toluene returns to the toluene shape selective disproportionation reactor. The toluene shape-selective disproportionation reaction temperature was 420 ℃, the reaction pressure was 2.1MPAG, and the weight space velocity was 2/HR. The toluene conversion for this reaction was 30%, the benzene/xylene molar ratio was 1.3, and the total yield of benzene and xylene was 94.7 wt%. The temperature of the benzene carbon nine-carbon deca-transalkylation reaction is 420 ℃, the reaction pressure is 3MPAG, the weight space velocity is 3/HR, and the selectivity of dimethylbenzene in the transalkylation product is 15.9%. The mass content of p-xylene in the xylene stream was 61.7%. The yield of the xylene carbon group in the process is 80.5 percent, and the yield of the p-xylene carbon group is 51.8 percent.
As a comparison, the xylene yield of comparative example 2 was lower than that of examples 1 to 4 of the present invention.
Claims (6)
1. A method for preparing xylene from methanol comprises the following steps: 1) the methanol raw material I is converted into a reaction product mainly containing aromatic hydrocarbon in an aromatization reactor; 2) separating the reaction product into a gas phase, an oil phase and a water phase by a three-phase separator; 3) returning the gas phase after removing hydrogen and methane to the aromatization reactor; 4) the oil phase is separated into a non-aromatic material flow and an aromatic material flow in a separation unit I; 5) the aromatic hydrocarbon material flow is separated into a toluene material flow, a xylene material flow, a mixed material flow of benzene, carbon, nine and ten, and material flows of more than eleven carbon in a separation unit II; 6) the benzene carbon nine carbon ten mixed material flow is sent into a transalkylation reactor to be converted into a transalkylation product; 7) returning the transalkylation product to the separation unit II; 8) feeding the toluene material flow and the methanol raw material II into a toluene-methanol methylation reactor to be converted into a methylated product, wherein the molar ratio of the toluene material flow to the methanol raw material II is 1: 1-1: 2; 9) the methylation product returns to the three-phase separator;
wherein the aromatization reactor conditions comprise: the reaction temperature is 460 to 540 ℃, and the reaction pressure is 0.1 to 0.4 MPAG;
the toluene methanol methylation reactor conditions include: the reaction temperature is 300 to 500 ℃, and the reaction pressure is 0.1 to 3 MPAG;
the transalkylation reactor conditions include: the reaction temperature is 325 to 420 ℃ and the reaction pressure is 1.5 to 3 MPAG.
2. The method for preparing xylene from methanol according to claim 1, characterized in that the aromatization reactor is a fluidized bed reactor and the aromatization reaction is carried out on a ZSM-5 molecular sieve catalyst.
3. The method of methanol to xylene according to claim 1, characterized in that the transalkylation reactor is a fixed bed reactor and the transalkylation reaction is carried out over a solid acid catalyst, a metal oxide catalyst or a molecular sieve catalyst.
4. The method for preparing xylene from methanol according to claim 1, characterized in that the toluene-methanol methylation reactor is a fixed bed reactor, and the methylation reaction is carried out under the action of a modified ZSM-5 molecular sieve catalyst.
5. The method for preparing xylene from methanol according to any one of claims 1 to 4, characterized in that the selectivity for p-xylene in the methylated product is not less than 80 WT%.
6. The method for producing xylene from methanol according to any one of claims 1 to 4, wherein the xylene content in the transalkylation product is not less than 10 WT%.
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| CN106608785B (en) * | 2015-10-22 | 2019-07-09 | 中国石油化工股份有限公司 | The method that methanol prepares benzene and dimethylbenzene |
| CN109694306B (en) * | 2017-10-20 | 2021-11-30 | 中国石油化工股份有限公司 | Method for preparing dimethylbenzene by efficiently converting methanol |
| CN111099944B (en) * | 2018-10-25 | 2022-08-12 | 中国石油化工股份有限公司 | Method for co-producing ethylene, propylene and xylene |
| CN112694378B (en) * | 2019-10-22 | 2023-05-02 | 中国石油化工股份有限公司 | Method for producing dimethylbenzene by taking oxygen-containing compound as raw material |
| CN112707777A (en) * | 2019-10-25 | 2021-04-27 | 中国石油化工股份有限公司 | Method for producing aromatic hydrocarbon by using oxygen-containing compound as raw material |
| CN111592443B (en) * | 2020-05-29 | 2022-07-19 | 中国海洋石油集团有限公司 | System and method for increasing yield of p-xylene through combination of toluene methylation and heavy aromatic hydrocarbon lightening |
| CN113929552B (en) * | 2020-06-29 | 2024-01-09 | 中国石油化工股份有限公司 | Method for producing aromatic hydrocarbon and application thereof |
| CN114436727B (en) * | 2020-10-20 | 2024-01-30 | 中国石油化工股份有限公司 | Device and method for preparing toluene from oxygen-containing compound |
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| CN1340489A (en) * | 2000-08-29 | 2002-03-20 | 中国石油化工集团公司 | Process for preparing p-xylene |
| CN103864565A (en) * | 2014-03-20 | 2014-06-18 | 华电煤业集团有限公司 | System and method of preparing paraxylene by alcohol/ether conversion |
| CN104892346A (en) * | 2014-03-07 | 2015-09-09 | 中石化洛阳工程有限公司 | Method and apparatus for preparing p-xylene from methanol |
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| CN101722033A (en) * | 2008-10-28 | 2010-06-09 | 中国石油化工股份有限公司 | Core-shell type aromatic conversion catalyst, preparation method and application thereof |
| CN101823929B (en) * | 2010-04-14 | 2013-05-22 | 清华大学 | System and process for preparing aromatic hydrocarbon by converting methanol or dimethyl ether |
| US9790139B2 (en) * | 2013-12-20 | 2017-10-17 | Exxonmobil Chemical Patents Inc. | Process for converting oxygenates to aromatic hydrocarbons |
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| CN1340489A (en) * | 2000-08-29 | 2002-03-20 | 中国石油化工集团公司 | Process for preparing p-xylene |
| CN104892346A (en) * | 2014-03-07 | 2015-09-09 | 中石化洛阳工程有限公司 | Method and apparatus for preparing p-xylene from methanol |
| CN103864565A (en) * | 2014-03-20 | 2014-06-18 | 华电煤业集团有限公司 | System and method of preparing paraxylene by alcohol/ether conversion |
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