CN112824365B - Process for disproportionating alkylaromatic hydrocarbons - Google Patents
Process for disproportionating alkylaromatic hydrocarbons Download PDFInfo
- Publication number
- CN112824365B CN112824365B CN201911149411.6A CN201911149411A CN112824365B CN 112824365 B CN112824365 B CN 112824365B CN 201911149411 A CN201911149411 A CN 201911149411A CN 112824365 B CN112824365 B CN 112824365B
- Authority
- CN
- China
- Prior art keywords
- gas
- reaction
- aromatic hydrocarbon
- alkyl aromatic
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 31
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 118
- 239000007788 liquid Substances 0.000 claims abstract description 103
- -1 alkyl aromatic hydrocarbon Chemical class 0.000 claims abstract description 86
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 82
- 238000000926 separation method Methods 0.000 claims abstract description 61
- 238000007323 disproportionation reaction Methods 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 57
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000007791 liquid phase Substances 0.000 claims abstract description 27
- 239000012071 phase Substances 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000011143 downstream manufacturing Methods 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000009825 accumulation Methods 0.000 claims description 5
- 238000010555 transalkylation reaction Methods 0.000 claims description 4
- 238000005265 energy consumption Methods 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000007670 refining Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 80
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102220065736 rs543286136 Human genes 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0292—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds with stationary packing material in the bed, e.g. bricks, wire rings, baffles
-
- 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
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
- B01J8/0446—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical
-
- 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
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
- B01J8/0496—Heating or cooling the reactor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of oil refining chemical industry, and particularly relates to a method for disproportionating alkyl aromatic hydrocarbon. The method comprises the following steps: (1) Mixing alkyl aromatic hydrocarbon and hydrogen to obtain hydrogen-mixed alkyl aromatic hydrocarbon; the molar ratio of hydrogen to alkylaromatic hydrocarbon is from 0.5 to 99.5 to 10; (2) Preheating and heating the hydrogen-mixed alkyl aromatic hydrocarbon in sequence to form a gas-liquid mixed reaction feed; (3) Feeding the reaction feed into a down-flow reactor, wherein the reaction feed enters a catalyst bed layer in the down-flow reactor for disproportionation reaction to generate a product containing p-xylene, and the product or a part of the product is used as a heat exchange medium to exchange heat with the hydrogen-mixed alkyl aromatic hydrocarbon so as to preheat the hydrogen-mixed alkyl aromatic hydrocarbon; (4) And (3) cooling the product after heat exchange, then carrying out gas-liquid separation, and respectively sending a gas-phase separator and a liquid-phase separator obtained by gas-liquid separation to downstream treatment. The method for disproportionating the alkyl aromatic hydrocarbon needs less equipment, has low energy consumption, and has low investment cost and production cost.
Description
Technical Field
The invention belongs to the technical field of oil refining chemical industry, and particularly relates to a method for disproportionating alkyl aromatic hydrocarbon.
Background
Benzene and Paraxylene (PX) are important basic organic chemical raw materials and are widely applied to the fields of daily chemical industry, medicines, chemical fibers, pesticides and the like. Among them, benzene is used to produce various products such as ethylbenzene, styrene, cyclohexane, caprolactam, etc. Para-xylene (PX) is an important raw material for producing resins, polyesters, detergents and medical products, and the demand for the para-xylene (PX) is large, so that the para-xylene (PX) is regarded as one of important products in the petrochemical industry
PX comes from naphtha reforming, ethylene pyrolysis gasoline xylene, toluene, C9A and C10A through disproportionation reaction under the action of catalyst to produce disproportionation and transalkylation reaction, and obtain benzene and mixed xylene (C8A), and the mixed xylene is passed through disproportionation device and separated to obtain target product PX.
Toluene disproportionation is the reaction of 2 moles of toluene over a catalyst to produce 1 mole of benzene and 1 mole of xylene. "transalkylation" is the reaction of 1 mole of toluene with 1 mole of trimethylbenzene (C9A) to produce 2 moles of xylene.
The existing method for disproportionating alkyl aromatic hydrocarbon roughly comprises the steps of mixing the alkyl aromatic hydrocarbon with hydrogen pressurized by a compressor, sending the mixture into a reactor, carrying out disproportionation reaction under the action of a catalyst in the reactor, wherein the reaction temperature is 400-460 ℃, carrying out gas-liquid separation on redundant hydrogen, circularly compressing for use, and sending a generated product to downstream processing. The conversion per pass of the alkylaromatic is not more than 46wt%, and the selectivity per pass of benzene (C6A) and mixed xylenes (C8A) is not more than 85wt%.
In the process of implementing the present invention, the inventors found that, in the process of producing PX by the existing method for disproportionating alkyl aromatic hydrocarbon, the disproportionation reaction temperature is high, and more energy is consumed, and the use of a compressor to compress hydrogen not only consumes high energy, but also the compressor occupies a relatively large space, and more capacity is consumed for compressing hydrogen. In a word, the existing method for disproportionating the alkylaromatic hydrocarbon has the disadvantages of low conversion rate of the alkylaromatic hydrocarbon, high energy consumption and high production cost, and limits the industrial application of the alkylaromatic hydrocarbon for producing PX.
Disclosure of Invention
The invention aims to provide a method for disproportionating alkyl aromatic hydrocarbon with low energy consumption and low cost.
In order to achieve the above object, the present invention provides a method for disproportionating alkyl aromatic hydrocarbon, the method comprising the steps of:
(1) Mixing alkyl aromatic hydrocarbon and hydrogen to obtain hydrogen-mixed alkyl aromatic hydrocarbon; the molar ratio of said hydrogen to said alkylaromatic hydrocarbon is from 0.5 to 1;
(2) Sequentially preheating and heating the hydrogen-mixed alkyl aromatic hydrocarbon to form a gas-liquid mixed reaction feed;
(3) Feeding the reaction feed into a downflow reactor, wherein the reaction feed enters a catalyst bed layer in the downflow reactor for disproportionation reaction to generate a product containing p-xylene, and the product or a part of the product is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon, so that the mixed hydrogen alkyl aromatic hydrocarbon is preheated;
(4) And after the heat exchange, cooling the product, and then carrying out gas-liquid separation, wherein a gas-phase separator and a liquid-phase separator obtained by the gas-liquid separation are respectively sent to downstream processing.
In one embodiment of the invention, the disproportionation reaction is carried out at a reaction temperature of 150-350 ℃ and a reaction pressure of 0.5-5.0MPaG in the downflow reactor.
In a preferred embodiment of the present invention, in the downflow reactor, the disproportionation reaction is carried out at a reaction temperature of 200 to 300 ℃ and a reaction pressure of 0.9 to 3.5MPaG.
In a preferred embodiment of the present invention, the liquid hourly space velocity of the reaction feed in the downflow reactor is in the range of from 0.3 to 10h -1 Preferably 0.5 to 8h -1 。
In a preferred embodiment of the present invention, the molar ratio of said hydrogen to said alkylaromatic hydrocarbon is from 1.
In the present invention, the alkyl aromatic hydrocarbon includes: at least one of carbon hepta-arene, carbon nonaarene and carbon decaarene.
In a preferred embodiment of the present invention, the downflow reactor comprises: a first downflow reactor, a second downflow reactor, a cooler, a knock-out pot, a feed line, and a product outlet line;
the feed line, the first downflow reactor, the second downflow reactor, the product outlet line, and the knock-out pot are in serial communication in that order;
the product output by the second downflow reactor is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon; or
The first downflow reactor is in parallel with the second downflow reactor;
the reaction feed enters the catalyst beds in the first downflow reactor and the second downflow reactor through the feed line for disproportionation reaction, and the products output by the first downflow reactor and the second downflow reactor are sent to a product outlet line and exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon as a heat exchange medium;
the cooler is used for cooling the heat-exchanged product.
In a preferred embodiment of the present invention, in step (3), after the reaction feed enters the catalyst bed layer in the downflow reactor for disproportionation reaction to generate a product containing p-xylene, the product containing p-xylene is sent to the upflow reactor, and is distributed sequentially through a gas-liquid distributor arranged inside the upflow reactor, the catalyst bed layer further undergoes disproportionation reaction to generate a product containing p-xylene, and the product is subjected to gas-liquid separation by a gas-liquid separation component to obtain a gas-phase product and a liquid-phase product;
the liquid phase product flows into a liquid phase product outlet pipeline and is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon, so that the mixed hydrogen alkyl aromatic hydrocarbon is preheated and then sent to downstream treatment;
and the gas-phase product flows into the gas-phase product outlet pipeline, is cooled by the cooler and then enters the gas-liquid separation tank for gas-liquid separation.
Further, the gas-liquid separation assembly includes: the device comprises an annular liquid accumulating plate and a cylinder body connected with the inner edge of the liquid accumulating plate;
the gas-liquid separation assembly and the shell positioned above the liquid accumulation plate enclose a gas-liquid separation space; the inside of the cylinder body forms a gas-liquid separation channel.
In a preferred embodiment of the present invention, the upflow reactor further comprises a cover plate disposed over the catalyst bed.
In one embodiment of the present invention, in the upflow reactor, the disproportionation reaction is carried out at a reaction temperature of 150 to 350 ℃ and a reaction pressure of 0.5 to 5.0MPaG.
In a preferred embodiment of the present invention, in the upflow reactor, the disproportionation is carried out at a reaction temperature of 200 to 300 ℃ and a reaction pressure of 0.9 to 3.5MPaG.
In a preferred embodiment of the present invention, the liquid hourly space velocity of the reaction feed in the upflow reactor is in the range of 0.3 to 10h -1 Preferably 0.5 to 8h -1 。
According to the method for disproportionating the alkyl aromatic hydrocarbon, the molar ratio of hydrogen to the alkyl aromatic hydrocarbon is 0.5-99.5-10, the consumption of hydrogen is reduced, the reaction feed is in a gas-liquid mixed state, the alkyl aromatic hydrocarbon is subjected to liquid phase hydrogenation, the generated product is used as a heat exchange medium of the reaction feed, the equipment required by the method for disproportionating the alkyl aromatic hydrocarbon is reduced, and the energy consumption and the cost for disproportionating the alkyl aromatic hydrocarbon to generate PX are reduced.
The method for disproportionating the alkyl aromatic hydrocarbon provided by the invention realizes the full mixing of the alkyl aromatic hydrocarbon and the hydrogen by arranging the gas-liquid distributor in the reactor, improves the yield of PX under the action of the catalyst, realizes the primary gas-liquid separation of the product by the gas-liquid separation component, cools the gas-phase product obtained by separation, then carries out the gas-liquid separation, and uses the liquid-phase product as the heat exchange medium of the reaction feed, so the method for disproportionating the alkyl aromatic hydrocarbon not only reduces the energy consumption and the cost for producing the PX, but also improves the yield of the PX.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The above and other objects, features and advantages of the present invention will become more apparent by describing in more detail exemplary embodiments thereof with reference to the attached drawings, in which like reference numerals generally represent like parts throughout.
FIG. 1 shows a schematic diagram of a downflow reactor in a process for the disproportionation of alkylaromatics provided by the present invention.
FIG. 2 is a schematic diagram of another downflow reactor in a process for the disproportionation of alkylaromatics according to the present invention.
FIG. 3 is a schematic diagram of yet another downflow reactor of a process for the disproportionation of alkylaromatic hydrocarbons in accordance with the present invention.
FIG. 4 is a schematic diagram showing the combination of a downflow reactor and an upflow reactor in a method for disproportionating alkyl aromatic hydrocarbon according to the present invention.
Reference numerals are as follows:
1. a downflow reactor;
10. a first downflow reactor;
20. a second downflow reactor;
2. an upflow reactor;
201. a housing;
202. a gas-liquid distributor;
303. a catalyst bed layer;
204. a gas-liquid separation assembly;
2041. an annular effusion plate; 2042. a cylinder body;
w, a feed line;
x, a product outlet line;
x1, a liquid-phase product outlet line;
x2, a gas phase product outlet line;
30. a cooler;
40. a gas-liquid separation tank;
50. a heat exchanger;
60. a heater.
Detailed Description
Preferred embodiments of the present invention will be described in more detail below. While the following describes preferred embodiments of the present invention, it should be understood that the present invention may be embodied in various forms and should not be limited by the embodiments set forth herein.
The invention provides a method for disproportionating alkyl aromatic hydrocarbon. Referring to FIG. 1, FIG. 1 is a schematic diagram of a downflow reactor of a method for disproportionation of alkylaromatic hydrocarbons according to the present invention. The method as shown in fig. 1 comprises the following steps:
(1) Mixing alkyl aromatic hydrocarbon and hydrogen as shown by an arrow to obtain hydrogen-mixed alkyl aromatic hydrocarbon; the molar ratio of said hydrogen to said alkylaromatic hydrocarbon is from 0.5 to 99.5 to 10.
(2) Preheating and heating the hydrogen-mixed alkyl aromatic hydrocarbon in sequence to form a gas-liquid mixed reaction feed;
(3) Feeding the reaction feed into a downflow reactor 1, wherein the reaction feed enters a catalyst bed layer in the downflow reactor 1 to carry out disproportionation reaction to generate a product containing p-xylene, and the product or a part of the product is used as a heat exchange medium to carry out heat exchange with the mixed hydrogen alkyl aromatic hydrocarbon, so that the mixed hydrogen alkyl aromatic hydrocarbon is preheated;
(4) And after the heat exchange, the product is cooled and then subjected to gas-liquid separation, and a gas-phase separator and a liquid-phase separator obtained by the gas-liquid separation are respectively sent to downstream processing.
According to the method for disproportionating the alkyl aromatic hydrocarbon, the molar ratio of hydrogen to the alkyl aromatic hydrocarbon is 1.
With continued reference to FIG. 1, the apparatus for gas-liquid separation may be a gas-liquid separation tank 40. The product containing p-xylene is sent to the gas-liquid separation tank 40 through the product outlet line X for gas-liquid separation, thereby obtaining a gas-phase separator and a liquid-phase separator.
With continued reference to fig. 1, the apparatus used for preheating may be a heat exchanger 50; the device used for heating may be a heater 60. The heat exchanger 50 and the heater 60 sequentially heat the mixed hydrogen alkyl aromatic hydrocarbon to reach the set reaction feeding temperature.
During the reaction, the alkylaromatic hydrocarbon is in a gas-liquid mixed phase, and the reaction temperature and pressure of the disproportionation reaction can be set by those skilled in the art. In view of the energy consumed for the reaction and the reaction efficiency, in a preferred embodiment of the present invention, in the downflow reactor 1, the disproportionation reaction is carried out at a reaction temperature of 150 to 350 ℃, preferably 200 to 300 ℃ and a reaction pressure of 0.5 to 5.0MPaG, preferably 0.9 to 3.5MPaG.
In a preferred embodiment of the invention, the liquid hourly space velocity of the reaction feed as it is fed to the downflow reactor is in the range of from 0.3 to 10h -1 Preferably 0.5 to 8h -1 。
The temperature of the hydrogenated alkyl aromatic hydrocarbon after heating can be set by those skilled in the art according to actual needs, and the invention is not particularly limited. It will be understood that the elevated temperature of the mixed hydrogen alkylaromatic hydrocarbon, i.e., the temperature of the reaction feed, is suitably slightly less than or equal to the reaction temperature in the downflow reactor. For example, the temperature of the reaction feed is from 150 to 350 ℃ and preferably from 200 to 300 ℃.
In the invention, hydrogen does not need to be recycled, so that the usage amount of hydrogen is not large, and the molar ratio of the hydrogen to the alkyl aromatic hydrocarbon is 1.
The catalyst of the present invention is not particularly limited in its components, shape and size as long as it can achieve disproportionation reaction and transalkylation reaction of alkylaromatic hydrocarbon.
Referring to FIG. 2, FIG. 2 is a schematic diagram of another downflow reactor of a process for the disproportionation of alkylaromatic hydrocarbons in accordance with the present invention. As shown in fig. 2, in the present invention, the downflow reactor comprises: a first downflow reactor 10, a second downflow reactor 20, a cooler 30, a knockout drum 40, a feed line W, and a product outlet line X; the feed line W, the first downflow reactor 10, the second downflow reactor 20, the product outlet line X, and the knock-out pot 40 are connected in series in this order; the product output by the second downflow reactor 20 is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon; the cooler 30 is used for cooling the heat-exchanged product. Improving the yield of PX. The first downflow reactor and the second downflow reactor are arranged in series and are suitable for the working conditions with higher requirements on the conversion rate of raw materials.
In the case where the first downflow reactor and the second downflow reactor are connected in series, the reaction temperature, the reaction pressure, and the liquid hourly space velocity of the reaction feed for the disproportionation reaction in the first downflow reactor and the second downflow reactor may be the same or different. The disproportionation reactions in the first downflow reactor and the second downflow reactor each independently have a reaction temperature of 150 to 350 ℃, each independently preferably 200 to 300 ℃, and a reaction pressure of 0.5 to 5.0MPaG, each independently preferably 0.9 to 3.5MPaG.
Referring to FIG. 3, FIG. 3 is a schematic diagram of a downflow reactor of a method for disproportionation of alkylaromatic hydrocarbon according to the present invention. As shown in fig. 3, the downflow reactor comprises: a first downflow reactor 10, a second downflow reactor 20, a cooler 30, a knockout drum 40, a feed line W, and a product outlet line X; said first downflow reactor 10 is in parallel with said second downflow reactor 20; the reaction feed enters the catalyst beds in the first downflow reactor 10 and the second downflow reactor 20 through the feed line W for disproportionation reaction, and the products output from the first downflow reactor 10 and the second downflow reactor 20 are sent to the product outlet line X and exchange heat with the hydrogen-mixed alkyl aromatic hydrocarbon as a heat exchange medium; the cooler 30 is used to cool the heat exchanged product in the product outlet line X. The increase of the processing amount of the alkyl aromatic hydrocarbon correspondingly increases the yield of PX.
In the case where the first downflow reactor and the second downflow reactor are connected in parallel, the reaction temperature of the disproportionation reaction in the first downflow reactor and the second downflow reactor,The reaction pressure and the liquid hourly space velocity of the reaction feed may be the same or different, preferably the same. Specifically, the reaction temperature of the disproportionation reaction is 150-350 ℃, preferably 200-300 ℃; the reaction pressure is 0.5-5.0MPaG, preferably 0.9-3.5MPaG; the liquid hourly space velocity of the respective reaction feed is 0.3-10h -1 Preferably 0.5 to 8 hours -1 。
In the invention, after the disproportionation reaction of the reaction feed in the downflow reactor, the generated product containing the paraxylene can further enter the upflow reactor with the reaction and separation functions for further disproportionation reaction. Referring to fig. 4, fig. 4 is a schematic diagram illustrating a combination of a downflow reactor and an upflow reactor in a method for disproportionating alkyl aromatic hydrocarbon according to the present invention. As shown in fig. 4, in step (3), after the reaction feed enters the catalyst bed layer in the downflow reactor 1 for disproportionation reaction to generate a product containing p-xylene, the product containing p-xylene is fed into the upflow reactor 2, and is distributed sequentially through a gas-liquid distributor 202 arranged inside the upflow reactor 2, the catalyst bed layer 203 further undergoes disproportionation reaction to generate a product containing p-xylene, and the product is subjected to gas-liquid separation by a gas-liquid separation module 204 to obtain a gas-phase product and a liquid-phase product; the liquid phase product flows into a liquid phase product outlet pipeline X1 and is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon, so that the mixed hydrogen alkyl aromatic hydrocarbon is preheated and then is sent to downstream treatment; the gas-phase product flows into the gas-phase product outlet pipeline X2, is cooled by the cooler 30, and then enters the gas-liquid separation tank 40 for gas-liquid separation. The downflow reactor and the upflow reactor with reaction and separation functions are connected in series, so that the method is suitable for the working condition with higher requirement on the conversion rate of the raw materials, and can reduce the energy consumption, the operation cost and the investment cost of disproportionated alkyl aromatic hydrocarbon.
The disproportionation reactions in the downflow reactor and upflow reactor may be carried out at the same reaction temperature, the same reaction pressure, and the same or different liquid hourly space velocities of the reaction feeds. Specifically, in the upflow reactor, the disproportionation reaction is carried out at a reaction temperature of 150 to 350 ℃, preferably 200 to 300 ℃, and a reaction pressure of 0.5 to 5.0MPaG, preferably 0.9 to 3.5MPaG.
Further, the upflow reactor 2 also comprises a cover plate disposed on the catalyst bed 203. The cover plate may be a grid plate. In the process that gas-liquid materials flow from bottom to top, the catalyst is prevented from moving up and down, and smooth flow of gas-liquid materials in the upflow reactor can be ensured.
With continuing reference to FIG. 4 for the structure of the gas-liquid separation assembly, the gas-liquid separation assembly 204 includes: the liquid collecting device comprises an annular liquid collecting plate 2041 and a cylinder 2042 connected with the inner edge of the liquid collecting plate 2041; the gas-liquid separation assembly 204 and the shell 201 above the liquid accumulation plate 2041 enclose a gas-liquid separation space a; a gas-liquid separation passage B is formed inside the cylinder 2042.
It is understood that three or four reactors may be connected in series, and the third reactor or the third and fourth reactors may be configured as a downflow reactor. The configuration of the downflow reactor may be that of downflow reactor 2 shown in FIG. 4.
The method for disproportionating alkyl aromatic hydrocarbon provided by the invention also comprises the following steps: a liquid level detection element for detecting the liquid level in the gas-liquid separation space of the upflow reactor and/or the downflow reactor, a liquid level control valve arranged on the liquid phase product outlet pipeline, a pressure detection element and a pressure control valve arranged on the gas phase outlet pipeline of the gas-liquid separation tank.
Further, the method further comprises: a liquid level detection element and a liquid level control valve for detecting the liquid level in the gas-liquid separation tank.
Example 1
This example provides a process for the disproportionation of alkylaromatic hydrocarbons. Referring to fig. 1, the method includes the following steps:
(1) Hydrogen and the alkylaromatic hydrocarbon were mixed in a molar ratio of 0.08 (i.e., hydrogen-to-oil ratio) in a feed line W as indicated by an arrow to obtain a hydrogen-mixed alkylaromatic hydrocarbon.
(2) The mixed hydrogen alkyl aromatic hydrocarbon is preheated by a heat exchanger 50 by taking a liquid-phase product as a heat exchange medium, and then the mixed hydrogen alkyl aromatic hydrocarbon is heated by a heater 60 until the temperature of the mixed hydrogen alkyl aromatic hydrocarbon is 220 ℃, so that a reaction feed in a gas-liquid mixed state is formed.
(3) The reaction feed, having a liquid hourly space velocity of 4.5h, was fed to the downflow reactor 1 via feed line W -1 Entering a catalyst bed layer for disproportionation reaction at the reaction temperature of 250 ℃ and the reaction pressure of 3.2MPaG to generate a product containing p-xylene.
(4) The product is heat exchanged by a heat exchanger 50 through a product outlet pipeline X, then cooled by a cooler 30, and then enters a gas-liquid separation tank 40 for gas-liquid separation, and gas-phase separators and liquid-phase separators obtained by the gas-liquid separation are respectively sent to downstream processing.
The single-pass conversion of the alkyl aromatic hydrocarbon is detected to be 50wt%, and the single-pass selectivity of the C6A and the C8A is detected to be 91wt%.
Examples 2 and 3
This example provides a process for the disproportionation of alkylaromatic hydrocarbons. Examples 2 and 3 differ from example 1 only in the reaction conditions, which are specified in table 1.
TABLE 1 reaction conditions for examples 2 and 3
Therefore, the method for disproportionating the alkyl aromatic hydrocarbon is suitable for the raw materials with high ethylbenzene content or high ethylbenzene content in C8A.
Comparative example 1
Compressing hydrogen to 3.0MPaG by a compressor, mixing the hydrogen with alkyl aromatic hydrocarbon according to the mol ratio of 3, and heating the mixed hydrogen and alkyl aromatic hydrocarbon to 420 ℃ by a heating furnace to form gaseous reaction feed.
Feeding the reaction feed into a reactor, feeding the reaction feed into a catalyst bed layer for disproportionation reaction, wherein the reaction temperature is 440 ℃, the reaction pressure is 2.4MPaG, and the liquid hourly space velocity of the reaction feed is 3.5h -1 To produce a product containing p-xylene; the reactor outlet product also contains a large amount of unreacted hydrogen and unconverted alkylAromatic hydrocarbon, and reaction by-products of toluene, o-xylene, m-xylene, C9A and the like.
The single-pass conversion rate of the alkyl aromatic hydrocarbon is 45wt%, and the single-pass selectivity of the C6A and the C8A is 85wt%.
Therefore, the method for disproportionating the alkyl aromatic hydrocarbon has low energy consumption, correspondingly, the production cost and the investment cost are low, and the conversion rate of the alkyl aromatic hydrocarbon and the content of PX generated are higher than those of the comparative example 1.
Example 4
This example provides a process for the disproportionation of alkylaromatic hydrocarbons. Referring to fig. 2, the method includes the following steps:
(1) The hydrogen and the alkylaromatic hydrocarbon were mixed in a molar ratio of 0.05 (i.e., hydrogen-to-oil ratio) in a feed line W as indicated by an arrow to obtain a hydrogen-mixed alkylaromatic hydrocarbon.
(2) The mixed hydrogen alkyl aromatic hydrocarbon is preheated by a heat exchanger 50 by taking a liquid-phase product as a heat exchange medium, and then the mixed hydrogen alkyl aromatic hydrocarbon is heated by a heater 60 until the temperature of the mixed hydrogen alkyl aromatic hydrocarbon is 210 ℃ to form a gas-liquid mixed reaction feed.
(3) The reaction feed is fed from the top of the first downflow reactor 10 into the first downflow reactor 10 through a feed line W, the liquid hourly space velocity of the reaction feed being 4h -1 The reaction mixture enters a catalyst bed layer in a first downflow reactor 10 for disproportionation reaction, the reaction temperature is 230 ℃, the reaction pressure is 3.0MPaG, the reaction mixture is discharged from the bottom, and then enters a second downflow reactor 20 from the top of the second downflow reactor 20 for disproportionation reaction in the catalyst bed layer, the reaction temperature is 230 ℃, the reaction pressure is 3.0MPaG, and a product containing p-xylene is generated and discharged from the bottom.
(4) The product is heat exchanged by a heat exchanger 50 through a product outlet pipeline X, then cooled by a cooler 30, and then enters a gas-liquid separation tank 40 for gas-liquid separation, and gas-phase separators and liquid-phase separators obtained by the gas-liquid separation are respectively sent to downstream processing.
The single-pass conversion of the alkylaromatic hydrocarbon was determined to be 61wt%, and the single-pass selectivities of C6A and C8A were determined to be 93wt%.
Example 5
This example provides a process for the disproportionation of alkylaromatic hydrocarbons. Referring to fig. 4, the method includes the following steps:
(1) The hydrogen and the alkylaromatic hydrocarbon are mixed in a molar ratio of 0.05 (i.e., hydrogen-to-oil ratio) in a feed line W as indicated by an arrow to obtain a mixed hydrogen alkylaromatic hydrocarbon.
(2) The mixed hydrogen alkyl aromatic hydrocarbon is preheated by a heat exchanger 50 by taking a liquid-phase product as a heat exchange medium, and then the mixed hydrogen alkyl aromatic hydrocarbon is heated by a heater 60 until the temperature of the mixed hydrogen alkyl aromatic hydrocarbon is 255 ℃ to form a reaction feed in a gas-liquid mixed state.
(3) The reaction feed, having a liquid hourly space velocity of 4h, was fed into the downflow reactor 1 via feed line W -1 The product enters a catalyst bed layer in a down-flow reactor 1 for disproportionation reaction at the reaction temperature of 280 ℃ and the reaction pressure of 3.0MPaG, then enters an up-flow reactor 2, passes through a gas-liquid distributor 202 therein, and then enters a catalyst bed layer 203 for further disproportionation reaction at the reaction temperature of 285 ℃ and the reaction pressure of 2.8MPaG to generate a product containing p-xylene, and the product is subjected to gas-liquid separation by a gas-liquid separation component 204 to obtain a gas-phase product and a liquid-phase product.
(4) The liquid phase product flows into a liquid phase product outlet pipeline X1, is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon, and then is sent to downstream treatment; the gas phase product flows into a gas phase product outlet pipeline X2, is cooled by a cooler 30 and then enters a gas-liquid separation tank 40 for gas-liquid separation, and gas phase separated matter and liquid phase separated matter obtained by gas-liquid separation are respectively sent to downstream processing.
The single-pass conversion of the alkylaromatic hydrocarbon is 68wt% and the single-pass selectivities of C6A and C8A are 91wt%.
Comparative example 2
The hydrogen is compressed to 1.45MPaG by a compressor, mixed with the alkyl aromatic hydrocarbon according to the mol ratio of 3.2, and the mixed hydrogen and the alkyl aromatic hydrocarbon are heated to 400 ℃ by a heating furnace to form gaseous reaction feed.
Feeding the reaction feed into a reactor, and allowing the reaction feed to enter a catalyst bed layer for disproportionation reaction at the reaction temperature of 410 DEG CThe reaction pressure was 1.2MPaG, and the liquid hourly space velocity of the reaction feed was 5h -1 To produce a product containing paraxylene; the outlet product of the reactor also contains a large amount of unreacted hydrogen and unconverted alkyl aromatic hydrocarbon, and reaction byproducts of benzene, toluene, ortho-xylene, meta-xylene, C9A, C10A and the like.
Through detection, the conversion rate of the alkyl aromatic hydrocarbon is 48%, and the mass ratio of PX/X (xylene) is 23%; the xylene (per pass) loss was 1.3%.
Therefore, the method for disproportionating the alkyl aromatic hydrocarbon has low energy consumption, correspondingly, the production cost and the investment cost are low, and the conversion rate of the alkyl aromatic hydrocarbon and the content of PX generated are higher than those of the comparative example 2.
While embodiments of the present invention have been described above, the above description is illustrative, not exhaustive, and not limited to the disclosed embodiments. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments.
Claims (10)
1. A process for the disproportionation of alkylaromatic hydrocarbons comprising the steps of:
(1) Mixing alkyl aromatic hydrocarbon and hydrogen to obtain hydrogen-mixed alkyl aromatic hydrocarbon; the molar ratio of said hydrogen to said alkylaromatic hydrocarbon is from 0.5 to 0.08;
(2) Preheating and heating the hydrogen-mixed alkyl aromatic hydrocarbon in sequence to form a gas-liquid mixed reaction feed;
(3) Feeding the reaction feed into a downflow reactor, wherein the reaction feed enters a catalyst bed layer in the downflow reactor for disproportionation reaction to generate a product containing p-xylene, and the product or a part of the product is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon, so that the mixed hydrogen alkyl aromatic hydrocarbon is preheated;
(4) After the heat exchange, the product is cooled and then subjected to gas-liquid separation, and a gas-phase separator and a liquid-phase separator obtained by the gas-liquid separation are respectively sent to downstream processing;
the disproportionation reaction in the downflow reactor has a reaction temperature of 150-280 ℃ and a reaction pressure of 0.5-5.0MPaG;
the alkyl aromatic hydrocarbon comprises: at least one of carbon heptaaromatics, carbon nonaaromatics, and carbon decaaromatics;
the catalyst can realize the disproportionation reaction and the transalkylation reaction of the alkyl aromatic hydrocarbon.
2. The method according to claim 1, wherein the disproportionation reaction is carried out at a reaction temperature of 200-280 ℃ and a reaction pressure of 0.9-3.5MPaG.
3. The process of claim 1, wherein the liquid hourly space velocity of the reaction feed is in the range of 0.3 to 10h -1 。
4. The process of claim 3, wherein the liquid hourly space velocity of the reaction feed is in the range of from 0.5 to 8h -1 。
5. The method of claim 1, wherein the downflow reactor comprises: a first downflow reactor (10), a second downflow reactor (20), a cooler (30), a gas-liquid separation tank (40), a feed line (W), and a product outlet line (X);
the feed line (W), the first downflow reactor (10), the second downflow reactor (20), the product outlet line (X), and the knock-out pot (40) are sequentially communicated in series;
the product output by the second downflow reactor (20) is used as a heat exchange medium to exchange heat with the mixed hydrogen alkyl aromatic hydrocarbon; or
Said first downflow reactor (10) being in parallel with said second downflow reactor (20);
the reaction feed enters the catalyst beds in the first downflow reactor (10) and the second downflow reactor (20) through the feed line (W) for disproportionation reaction, and the products output by the first downflow reactor (10) and the second downflow reactor (20) are sent to a product outlet line (X) and exchange heat with the hydrogen-mixed alkyl aromatic hydrocarbon as a heat exchange medium;
the cooler (30) is used for cooling the heat-exchanged product.
6. The method according to claim 1, wherein in the step (3), after the reaction feed enters the catalyst bed in the downflow reactor (1) to carry out disproportionation reaction to generate a product containing p-xylene, the product containing p-xylene is sent to an upflow reactor (2), and is distributed by a gas-liquid distributor (202) arranged inside the upflow reactor (2) in sequence, the catalyst bed (203) further carries out disproportionation reaction to generate a product containing p-xylene, and a gas-liquid separation component (204) carries out gas-liquid separation on the product to obtain a gas-phase product and a liquid-phase product;
the liquid phase product flows into a liquid phase product outlet pipeline (X1) and is used as a heat exchange medium to exchange heat with the hydrogen-mixed alkyl aromatic hydrocarbon, so that the hydrogen-mixed alkyl aromatic hydrocarbon is preheated and then is sent to downstream processing;
and the gas-phase product flows into the gas-phase product outlet pipeline (X2), is cooled by the cooler (30), and then enters the gas-liquid separation tank (40) for gas-liquid separation.
7. The method of claim 6, wherein the gas-liquid separation assembly (204) comprises: the device comprises an annular liquid accumulation plate (2041) and a cylinder (2042) connected with the inner edge of the liquid accumulation plate (2041);
the gas-liquid separation assembly (204) and the shell (201) positioned above the liquid accumulation plate (2041) enclose a gas-liquid separation space (A); the inside of the cylinder (2042) forms a gas-liquid separation channel (B).
8. The method according to claim 6, wherein the upflow reactor (2) further comprises a cover plate disposed over the catalyst bed (203).
9. The process according to any one of claims 6 to 8, characterized in that in the upflow reactor (2), the disproportionation is carried out at a reaction temperature of 150 to 285 ℃ and a reaction pressure of 0.5 to 5.0MPaG.
10. The method of claim 9, wherein the disproportionation reaction is carried out at a reaction temperature of 200-285 ℃ and a reaction pressure of 0.9-3.5MPaG.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911149411.6A CN112824365B (en) | 2019-11-21 | 2019-11-21 | Process for disproportionating alkylaromatic hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911149411.6A CN112824365B (en) | 2019-11-21 | 2019-11-21 | Process for disproportionating alkylaromatic hydrocarbons |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112824365A CN112824365A (en) | 2021-05-21 |
| CN112824365B true CN112824365B (en) | 2023-03-10 |
Family
ID=75907600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911149411.6A Active CN112824365B (en) | 2019-11-21 | 2019-11-21 | Process for disproportionating alkylaromatic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112824365B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115301165A (en) * | 2022-03-04 | 2022-11-08 | 陕西北元化工集团股份有限公司 | A kind of device and method for synthesizing vinyl chloride by acetylene method |
| CN115872828B (en) * | 2022-12-12 | 2024-05-31 | 黄河三角洲京博化工研究院有限公司 | Method for separating and purifying mesitylene from reformed C9 aromatic hydrocarbon by using eutectic solvent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1156976A (en) * | 1994-07-26 | 1997-08-13 | 切夫里昂化学公司 | Para-xylene selective reforming/aromatization |
| CN1902147A (en) * | 2003-12-31 | 2007-01-24 | 埃克森美孚化学专利公司 | Alkylation Process for Aromatic Compounds |
| CN104276923A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Method for preparing xylene by shape-selective disproportionation of toluene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6706937B2 (en) * | 2002-06-11 | 2004-03-16 | Fina Technology, Inc. | Conversion of aromatic hydrocarbons |
-
2019
- 2019-11-21 CN CN201911149411.6A patent/CN112824365B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1156976A (en) * | 1994-07-26 | 1997-08-13 | 切夫里昂化学公司 | Para-xylene selective reforming/aromatization |
| CN1902147A (en) * | 2003-12-31 | 2007-01-24 | 埃克森美孚化学专利公司 | Alkylation Process for Aromatic Compounds |
| CN104276923A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Method for preparing xylene by shape-selective disproportionation of toluene |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112824365A (en) | 2021-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101676151B1 (en) | Combined heavy reformate dealkylation-transalkylation process for maximizing xylenes production | |
| CN112824365B (en) | Process for disproportionating alkylaromatic hydrocarbons | |
| EP2252566A2 (en) | Process for liquid phase alkylation | |
| EP3616784A1 (en) | Apparatus and method for preparing para-xylene co-producing low-carbon olefin from methanol and/or dimethyl ether and benzene | |
| CN106608783A (en) | Method for preparing xylene from methanol | |
| CN104557401B (en) | Using moving bed technique propylene enhancing and the method for aromatic hydrocarbons | |
| KR20160105486A (en) | Purification of aromatic carboxylic acids | |
| CN106854135B (en) | Method for preparing p-xylene by alkylating benzene and methanol | |
| CN107226772B (en) | From C9+Method for preparing dimethylbenzene and coproducing durene from heavy aromatics | |
| CN104557426B (en) | The slurry reactor method of alkylating aromatic hydrocarbon | |
| CN110642665B (en) | C9+Process for producing dimethylbenzene from heavy aromatic hydrocarbon | |
| CN112824363B (en) | Method for isomerizing carbon octa-arene | |
| CN112824364B (en) | Process for disproportionating alkyl aromatic hydrocarbon | |
| CN112824362B (en) | Method for isomerizing carbon octa-arene | |
| KR20160104705A (en) | Process for the preparation of terephthalic acid using dehydration tower condensate for the purification of the crude product | |
| CN114716293A (en) | Process system and process method for increasing yield of p-xylene | |
| CN113045374B (en) | Reaction device and reaction method for producing paraxylene by toluene methanol alkylation | |
| CN104276923B (en) | Methylbenzene shape selective disproportionation dimethylbenzene method | |
| WO2009114263A2 (en) | Process for production of ethylbenzene from toluene and methane | |
| CN104109065A (en) | Method of preparing xylene by alkylation of benzene and methanol | |
| CN106608785A (en) | Method for preparing benzene and xylene from methanol | |
| CN111592443A (en) | System and method for increasing yield of p-xylene through combination of toluene methylation and heavy aromatic hydrocarbon lightening | |
| US11680209B1 (en) | Process for converting plastic feed containing polypropylene to aromatics | |
| CN111072445B (en) | Process for synthesizing xylene from toluene and methanol | |
| CN102276410B (en) | Method for synthesizing ethylbenzene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |