WO2013016396A2 - Fluid bed reactor with staged baffles - Google Patents
Fluid bed reactor with staged baffles Download PDFInfo
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- WO2013016396A2 WO2013016396A2 PCT/US2012/048085 US2012048085W WO2013016396A2 WO 2013016396 A2 WO2013016396 A2 WO 2013016396A2 US 2012048085 W US2012048085 W US 2012048085W WO 2013016396 A2 WO2013016396 A2 WO 2013016396A2
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- fluid bed
- reactor system
- bed reactor
- catalyst
- methanol
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/24—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique
- B01J8/34—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique with stationary packing material in the fluidised bed, e.g. bricks, wire rings, baffles
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/1818—Feeding of the fluidising gas
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/1818—Feeding of the fluidising gas
- B01J8/1827—Feeding of the fluidising gas the fluidising gas being a reactant
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/1872—Details of the fluidised bed reactor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C2/865—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 ether
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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
Definitions
- the invention relates to a process of alkylating aromatic hydrocarbons, and more particularly a process of making paraxylene by alkylation of benzene and/or toluene with methanol, and to an apparatus for carrying out said process.
- paraxylene selectivity means that paraxylene is produced in amounts greater than is present in a mixture of xylene isomers at thermodynamic equilibrium, which at ordinary processing temperatures is about 24 mol%. Paraxylene selectivity is highly sought after because of the economic importance of paraxylene relative to meta- and orthoxylene. Although each of the xylene isomers have important and well-known end uses, paraxylene is currently the most economically valuable, serving as an intermediate in such important and diverse end uses as bottle plastic and polyester fibers.
- toluene and/or benzene are alkylated with methanol, in the presence of a suitable catalyst, to form xylenes in a reactor in a system illustrated schematically in Figure 1, wherein a feed comprising reactants enter fluid bed reactor 11 via conduit 1 and effluent comprising product exits through conduit 5, and the catalyst circulates between fluid bed reactor 11, apparatus 12, which strips fluid from the catalyst, and catalyst regenerator 13, via conduits 2, 3, and 4, respectively.
- Water is typically co-fed with toluene and methanol to minimize toluene coking in the feed lines and methanol self-decomposition.
- Other side reactions include the formation of light olefins, light parafins, as reactions that convert paraxylenes to other xylene isomers or heavier aromatics.
- Gas bubbles formed at the bottom of a fluid bed will grow as they rise through the bed until they reach a maximum stable bubble size. Because the bubbles will grow at different rates, there will be typically a broad distribution of bubble sizes in a fluidized bed.
- a broad bubble size distribution can cause significant gas phase back-mixing both at a local level due to formation of turbulent eddies as well as at the global level due to uneven axial velocity profiles across the horizontal direction. Such gas back- mixing keeps portions of the desired product in contact with active catalyst for longer than the expected plug flow reactor residence time.
- back-mixing increases gas phase residence time, another phenomenon can simultaneously result in decrease of the gas phase residence time.
- staged injection in the presence of a baffle system avoids secondary reactions such as isomerization of the desired paraxylene to its less desirable isomers, and improves selectivity to paraxylene from about 60-70 wt% to above 80 wt%, such as to 80 - 90 wt% in embodiments.
- the present inventors have surprisingly discovered a process and apparatus or system adapted therefore, wherein the combination of reduced gas phase back-mixing and by-pass phenomena can work in concert to improve both conversion and selectivity, as well as increase catalyst utilization, by the use of staging baffles in a deep fluid bed to yield smaller and more uniform, and thus controllable, bubble sizes, and combining staged methanol injection to the reactor bed with the use of structured packing layers as staging baffles selectivity to more efficiently provide the desired products.
- the invention is directed to a process of alkylating aromatic hydrocarbons, and more particularly a process of making paraxylene by alkylation of benzene and/or toluene with methanol and/or dimethylether (DME), and to an apparatus for carrying out said process, the improvement comprising the staged injection of at least one of the reactants, benzene and/or toluene and methanol, wherein plural injection stages are separated by baffle material, preferably structured material, so as to decrease at least one of gas phase back- mixing, by-pass phenomena, and gas bubble size.
- baffle material preferably structured material
- Figure 1 is a schematic of a reactor system including reactor and regenerator and some associated auxiliary devices and transfer piping per se known in the art.
- Figure 2 is a schematic of a reactor system including reactor and regenerator and some associated auxiliary devices and transfer piping according to the present invention.
- Figures 3A and 3B illustrate schematically embodiments of the reactor system according to the present invention.
- a fluidized bed process for the alkylation of aromatic hydrocarbons by contact of reactants in the presence of a catalyst that promotes said alkylation said process characterized by the generation of gas bubbles within a fluid bed reactor system, the improvement comprising the introduction of at least one of said reactants by injection at plural locations within said reactor system, each location defined as a stage spaced apart from at least one other stage, and wherein at least one stage is separated from the at least one other stage by baffle material, such as structured packing so, as to decrease at least one of gas phase back-mixing, by -pass phenomena, and gas bubble size.
- the invention is also directed to an apparatus for the manufacture of paraxylene selectively by contact of benzene and/or toluene with a suitable molecular sieve catalyst in a fluid bed reactor, the improvement comprising the injection of at least one reactant into said reactor in stages, wherein each stage is separated from the next stage by baffle material, preferably structured packing.
- the stages may be in one or more separate reactors in series, wherein at least one of said stages is adjacent to and upstream of baffle material in order to achieve the purpose of the present invention.
- a fluid bed reactor system for the manufacture of xylene by an alkylation reaction comprising contact of an alkylating agent with benzene and/or toluene in the presence of a catalyst that promotes said alkylation reaction, the improvement comprising the staged injection of at least one of the reactants, benzene and/or toluene and methanol and/or dimethylether, wherein plural injection stages are separated by baffle material, such as structured packing, said baffle material characterized as suitable to decrease at least one of gas phase back-mixing, by-pass phenomena, and gas bubble size in the manufacture of xylene by said alkylation reaction.
- baffle material such as structured packing
- said baffle material characterized as suitable to decrease at least one of gas phase back-mixing, by-pass phenomena, and gas bubble size in the manufacture of xylene by said alkylation reaction.
- baffle material refers to structured and unstructured material, e.g., aggregate or column packing material.
- structured material provides certain additional benefits in the present invention as compared with unstructured material.
- structured material is per se well known in the art and can be defined as packing wherein individual members have specific orientation relative to each other and to the column axis. See U.S. Patent No. 5, 132,056.
- the desired product is an intermediate in the reaction chains, it is important to control gas back-mixing and gas by-pass which a deep fluid bed is usually prone to.
- the selectivity for the desired paraxylene product is maximized by reducing gas phase back- mixing with a few layers of structured packing which function as staging baffles in the fluid bed reactor.
- the staging baffles also have the added beneficial effect of minimizing gas by- pass which, if not controlled, would reduce reactor utilization.
- one or more reactants are provided in stages through plural conduits la - Id to feed plural spargers 102a - 102d in the fluid bed reactor 1011.
- the reactants may be sparged as a gas, as a liquid, or a combination thereof.
- different reactants may be provided through different conduits, so that, by way of example, toluene and/or benzene may be provided through conduit la and methanol may be provided through each of plural conduits lb, lc, and Id.
- water and/or steam may also be provided through one or more of the plural conduits with one or more of the reactants.
- Conduit 1002 represents a transfer line to stripper 1012.
- conduit 3 transfer line to regenerator 13
- conduit 1004 is the transfer line to fluid bed reactor 1011
- 5 is the fluid bed reactor 1011 effluent outlet (i.e., comprising desired product paraxylene)
- element 1012 represents the catalyst stripper apparatus, detailed features of which are per se known in the art and do not form a part of the present invention, except as otherwise explicitly set forth herein
- element 1013 represents the fluid bed regenerator, detailed features of which are also per se known in the art and do not form a part of the present invention, except as otherwise explicitly set forth herein
- conduit 33 is the riser transfer line to regenerator 1013.
- Element 291 is a vent for flue gases (e.g., C0 2 , CO, H 2 0, N 2 , 0 2 ).
- elements 102a - 102d are plural, staged, spargers, which may be of the type known in the art; elements 103a - 103c represent plural structure packing layers, described in more detail below.
- elements 110. 120. 230 and 240 represent cyclones which in certain embodiments are important features of the present invention and are described in more detail below.
- Element 110 is the secondary cyclone for fluid bed reactor 1011; 112 represents the dense bed for catalyst stripper 1002.
- 120 represents the primary cyclone for reactor 1011.
- element 130 is the catalyst cooler, which is also per se known in the art, the detailed features of which do not form a part of the present invention, except as otherwise explicitly set forth herein. Additional features include 145. the secondary cyclone dipleg; 146. the primary cyclone dipleg; 151. the regenerator gas sparger (regenerator gas is, at the inlet, advantageously air or oxygen); 191. the stripper gas outlet; 210.
- Cyclones per se are often used in fluid-solid systems. In the present system they are used for separation of the catalyst particles from the gas flow, so that the gas (either reactor effluent, or regenerator flue gas) can leave the vessel, and the catalyst can be returned back to the fluid bed.
- the gas-solids mixture would first go through the primary cyclone (120. 240). with the majority of the solids separated and returned to the fluid bed through the dipleg (146. 246). Then the gas flow with a much lower solids fraction goes through a secondary cyclone (110. 230). further separating the solids from the gas stream, returned to the fluid bed through the dipleg (145. 245).
- Figure 3a represents schematically a configuration analogous to Figure 2, that is, with plural injection of, for instance, toluene and/or benzene through conduits 1001a, and methanol through conduits 1002a, 1002b, and 1002c.
- the structured packing is represented by elements 1103a, 1103b, and 1103c.
- structured packing illustrated in Figure 2 at plural staged positions 103a - 103c in a single reactor, in Figure 3a at plural staged positions 1103a - 1103c in a single reactor, or in Figure 3b at plural stages positions 1103a - 1103b in reactors in series, numerous structured packing material is known in the art, such as those structured packings used in distillation columns.
- multiple layers of Koch-GlitschTM KFBETM IIB, such as 1-foot (30-31 cm) are particularly useful to separate the dense fluid bed into multiple stages.
- This type of packing has been found particularly useful for a fluid bed reactor for the alkylation of benzene and/or toluene using methanol as an alkylating agent and a catalyst comprising a molecular sieve, such as ZSM-5, because of its high open area for both gas and catalyst solids to pass through and its capability to control bubble sizes.
- a catalyst comprising a molecular sieve, such as ZSM-5
- each stage of structured packing 103a - 103c may be, for instance, 5-35 cm thick, such as 5 cm, 10 cm, 18 cm, 27 cm, 30 cm, 31 cm, 35 cm, etc.) with each layer individually selected, or they may be of uniform thickness, or a mixture of uniform and non-uniform thickness, of structured packing of the type discussed above, wherein the whole dense bed (210 in Figure 2; not shown in Figures 3A or 3B) has a height of from 300-1000 cm, such as about 350 cm, or 450 cm, or 600 cm, or 700 cm, or 900 cm).
- the maximum height for bubbles to grow can be reduced, minimizing the forming of large bubbles and gas by -pass.
- the toluene main sparger is located at the bottom of the first lower stage and three to five smaller spargers inject methanol into each of the dense bed stages. Each methanol sparger is located below a layer of packing for optimal distribution of methanol gas injected into the fluid bed.
- the toluene injected at the bottom of the reactor has a separate sparger from the bottom level methanol injection, instead of a single sparger for the mixture of toluene and methanol.
- This separate sparger configuration provides flexibility in both apparatus construction and operation. For instance, a separate toluene sparger allows reduced water co-feed level for the toluene sparger to minimize the amount of inert steam fed into the reactor. Separating methanol from the toluene feeding lines also allows a higher feed temperature for toluene in order to provide more heat to maintain the reactor energy balance.
- the methanol sparger(s) may be lined with refractory to reduce heat transfer from the hot fluid bed into the methanol in the sparger. This avoids methanol heating up to decomposition temperature prior to contacting toluene and catalyst.
- selectivity to paraxylene can be increased from about 60 - 70 wt% to 80 wt% or above, such as 90 wt%, using a reactor and process according to the present invention, when compared to a reactor without the staged baffles.
- the configuration of a deep fluid bed with structure packing as staging baffles and staged methanol injection may be characterized by the following:
- Catalyst holdup means the height of the reactor dense bed level (210 in Figure 2), which can be altered up or down by varying the catalyst withdrawal rate.
- Catalyst activity can be controlled by several methods, including changing the weight hourly space velocity and/or catalyst regeneration conditions. It is beneficial to control these aspects of operation with a goal of decreasing fluctuations in methanol conversion, to keep constant reactor effluent composition to minimize the impact on downstream material separation and recycling as well as on the overall process productivity.
- stages of methanol injection there are three, four, five, six, etc., stages of methanol injection and the amount of methanol introduced at each stage is from 0 - 99 mol%, or 0 - 40 mol%, or from 0 - 33 mol%, based on the total amount of methanol injected.
- the system may also be operated with one or more or the plural injection stages and baffle stages in separate reactors in series.
- all stages operate with substantially similar amounts of methanol injection, e.g., three sparger stages each injecting between about 30 - 35 mol% of the total methanol injected, such as each about 33 mol%, or four sparger stages each injecting between about 20 - 30 mol%, such as each about 25 mol% of the total methanol injected.
- three sparger stages each injecting between about 30 - 35 mol% of the total methanol injected, such as each about 33 mol%
- four sparger stages each injecting between about 20 - 30 mol%, such as each about 25 mol% of the total methanol injected.
- the uppermost sparger stage (which could be the third, or fourth or fifth stage) would be adjusted within that range, or even shut down, so that the other three sparger stages (in the case of four total sparger stages) operated at about 33 mol% of the total methanol injected, until normal operating conditions can be reestablished.
- there are at least two stages of methanol injection with each injection stage introducing at least 5 wt% of the total amount of all methanol injected at all injection stages.
- One or more catalysts that promotes the alkylation reaction may be used in the present invention.
- ZSM-5 zeolite such as disclosed in WO 98/14415 or any of the prior art patents set forth in the Background section above, is suitable for the present invention.
- a phosphorus-containing ZSM-5 zeolite that has been steam-treated is preferred.
- the catalyst also preferably comprises clay as a binder.
- Suitable reaction conditions may be readily determined by one of ordinary skill in the art in possession of the present disclosure.
- Such suitable reaction conditions may include the following ranges: (a) Temperature-about 500° to about 700°C, and preferably between about 500° to about 600°C; (b) Pressure— about 1 atmosphere to about 1000 psig (about 100 to about 7000 kPa), and preferably about 10 psig to about 200 psig; (c) moles toluene/moles methanol (in the reactor charge)— at least about 0.2, and preferably from about 0.2 to about 20; and (d) a weight hourly space velocity ("WHSV") for total hydrocarbon feed to the reactor(s) of about 0.2 to about 1000, preferably about 0.5 to about 500 for the aromatic reactant, and about 0.01 to about 100 for the combined alkylating reagent stage flows, based on total catalyst in the reactor(s).
- WHSV weight hourly space velocity
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Abstract
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12817575.9A EP2736630B1 (en) | 2011-07-27 | 2012-07-25 | Fluid bed reactor with staged baffles |
ES12817575.9T ES2666456T3 (en) | 2011-07-27 | 2012-07-25 | Fluid bed reactor with graduated baffles |
JP2014522960A JP6162117B2 (en) | 2011-07-27 | 2012-07-25 | Fluidized bed reactor with multistage baffle |
BR112014001830A BR112014001830A2 (en) | 2011-07-27 | 2012-07-25 | fluid bed reactor with stepped baffles |
KR1020147001932A KR101602076B1 (en) | 2011-07-27 | 2012-07-25 | Fluid bed reactor with staged baffles |
SG2014002232A SG2014002232A (en) | 2011-07-27 | 2012-07-25 | Fluid bed reactor with staged baffles |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US201161512271P | 2011-07-27 | 2011-07-27 | |
US61/512,271 | 2011-07-27 |
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WO2013016396A2 true WO2013016396A2 (en) | 2013-01-31 |
WO2013016396A3 WO2013016396A3 (en) | 2013-04-25 |
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PCT/US2012/048085 WO2013016396A2 (en) | 2011-07-27 | 2012-07-25 | Fluid bed reactor with staged baffles |
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US (1) | US9095831B2 (en) |
EP (1) | EP2736630B1 (en) |
JP (2) | JP6162117B2 (en) |
KR (1) | KR101602076B1 (en) |
CN (2) | CN202909704U (en) |
BR (1) | BR112014001830A2 (en) |
ES (1) | ES2666456T3 (en) |
MY (1) | MY179930A (en) |
PT (1) | PT2736630T (en) |
SG (1) | SG2014002232A (en) |
TW (1) | TWI495511B (en) |
WO (1) | WO2013016396A2 (en) |
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EP3617177A4 (en) * | 2017-04-27 | 2020-05-06 | Dalian Institute Of Chemical Physics, Chinese Academy of Sciences | Fluidized bed reactor and method for producing para-xylene co-produced low-carbon olefin from benzene and methanol and/or dimethyl ether |
EP3628397A4 (en) * | 2017-04-27 | 2021-01-06 | Dalian Institute Of Chemical Physics, Chinese Academy of Sciences | Device and method for preparing para-xylene and co-producing low-carbon olefins from methanol and/or dimethyl ether and toluene |
EP3616783A4 (en) * | 2017-04-27 | 2021-02-17 | Dalian Institute Of Chemical Physics, Chinese Academy of Sciences | Fluidized bed gas distributor, reactor using fluidized bed gas distributor, and method for producing para-xylene and co-producing low-carbon olefins |
US11084765B2 (en) | 2017-04-27 | 2021-08-10 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Device and method for preparing para-xylene and co-producing light olefins from methanol and/or dimethyl ether and benzene |
US11180431B2 (en) | 2017-04-27 | 2021-11-23 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Fluidized bed device and method for preparing para-xylene and co-producing light olefins from methanol and/or dimethyl ether and toluene |
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TWI495511B (en) * | 2011-07-27 | 2015-08-11 | Exxonmobil Chem Patents Inc | Fluid bed reactor with staged baffles |
US9193645B2 (en) | 2012-08-31 | 2015-11-24 | Exxonmobil Chemical Patents Inc. | Xylene isomerization process and catalyst therefor |
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JP6743173B2 (en) * | 2016-03-25 | 2020-08-19 | エクソンモービル・ケミカル・パテンツ・インク | Catalysts and processes for the production of paraxylene |
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US20180155255A1 (en) * | 2016-12-05 | 2018-06-07 | Exxonmobil Chemical Patents Inc. | Process of Producing Paraxylene by The Methylation of Toluene and/or Benzene |
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US10450240B2 (en) * | 2017-11-10 | 2019-10-22 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
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US11192833B2 (en) * | 2018-06-27 | 2021-12-07 | Uop Llc | Processes and apparatuses for toluene and benzene methylation in an aromatics complex |
CN109096041A (en) * | 2018-08-23 | 2018-12-28 | 陕西煤化工技术工程中心有限公司 | A kind of method that toluene mixture produces paraxylene |
US11078133B2 (en) * | 2019-12-06 | 2021-08-03 | Uop Llc | Aromatic alkylation process |
CA3184956A1 (en) | 2020-07-31 | 2022-02-03 | Robert G. Tinger | Processes for producing high-octane-number fuel component |
CN112717839B (en) * | 2020-12-25 | 2022-05-03 | 江苏新河农用化工有限公司 | Fluidized reaction device and method for oxidizing m-xylene by using same |
CN112608837B (en) * | 2020-12-30 | 2022-04-19 | 西北大学 | Biological enzyme catalytic reaction device |
CN113082977B (en) * | 2021-04-06 | 2021-11-30 | 江苏舒源空调制造有限公司 | Efficient waste gas treatment system and process |
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US11084765B2 (en) | 2017-04-27 | 2021-08-10 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Device and method for preparing para-xylene and co-producing light olefins from methanol and/or dimethyl ether and benzene |
US11180431B2 (en) | 2017-04-27 | 2021-11-23 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Fluidized bed device and method for preparing para-xylene and co-producing light olefins from methanol and/or dimethyl ether and toluene |
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Also Published As
Publication number | Publication date |
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CN202909704U (en) | 2013-05-01 |
EP2736630A4 (en) | 2015-04-22 |
TWI495511B (en) | 2015-08-11 |
JP2017125059A (en) | 2017-07-20 |
SG2014002232A (en) | 2014-04-28 |
JP6162117B2 (en) | 2017-07-12 |
CN102895923B (en) | 2016-08-10 |
ES2666456T3 (en) | 2018-05-04 |
US20130165724A1 (en) | 2013-06-27 |
EP2736630A2 (en) | 2014-06-04 |
KR101602076B1 (en) | 2016-03-17 |
MY179930A (en) | 2020-11-19 |
WO2013016396A3 (en) | 2013-04-25 |
PT2736630T (en) | 2018-04-05 |
CN102895923A (en) | 2013-01-30 |
KR20140027512A (en) | 2014-03-06 |
US9095831B2 (en) | 2015-08-04 |
EP2736630B1 (en) | 2018-01-31 |
TW201332657A (en) | 2013-08-16 |
BR112014001830A2 (en) | 2017-02-21 |
JP2014531400A (en) | 2014-11-27 |
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