CN111777487B - Method for preparing coronene compound from alcohol raw material - Google Patents
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Abstract
The invention relates to a method for preparing coronene compounds from alcohol raw materials. The method of the invention comprises the following steps: the raw material containing the alcohol compound and a catalyst are contacted and reacted in a reactor to obtain the coronene compound; wherein the catalyst comprises an activated silicon-aluminum molecular sieve.
Description
Technical Field
The application relates to a method for preparing coronene compounds, belonging to the field of organic chemistry.
Background
The coronene compound is a condensed ring aromatic compound with highly symmetrical structure, and has a larger conjugated system, a strong rigid structure and coplanarity. Coronene has a maximum absorption wavelength of 255nm and a maximum emission wavelength of 520nm, and has extremely high fluorescence quantum efficiency, and therefore, it occupies an extremely important position in the field of fluorescent materials, particularly ultraviolet fluorescent materials. The coronene compound is an excellent material for preparing an Ultraviolet Charge Coupled Device (UV-CCD), and the Ultraviolet CCD image sensor has wide application in the fields of nuclear explosion, medicine, astronomy, military (radar) and the like.
At present, the preparation method of coronene mainly comprises three methods, namely a Wurtz-Fittig reaction synthesis method, a Diels-Alder reaction synthesis method and an anion reaction synthesis method.
Wurtz-Fittig reaction synthesis method in 1951, Wilson Baker et al synthesized coronene from 2, 7-dimethylnaphthalene under the reduction of Na and palladium black. The synthetic route is shown below. In this preparation method, the final yield of coronene is 4%, the reaction time is long, the conditions are severe and the product isolation is difficult, and thus it is not suitable for mass production.
Diels-Alder reaction synthesis in addition to the Wurtz-Fittig reaction, Diels-Alder reaction is also an important and efficient method for preparing polycyclic compounds. In 1957, e.clar and e.zander produced coronene with a total reaction yield of 25% using a two-step Diels-Alder reaction and a two-step decarboxylation reaction. Their synthetic routes are shown below. However, the raw material perylene of the method is expensive, and the reaction process involves operations such as high temperature, vacuum decarboxylation, sublimation purification and the like for many times, and the conditions are harsh, so the method is still quite inconvenient in actual operation.
3. Anion reaction synthesis method: in 1996, Van Dijk et al published a method for the synthesis of coronene using the anion of a polycyclic aromatic hydrocarbon, the synthetic route of which is shown below. They still start from perylenes, whose anions are obtained ultrasonically under the action of Na in THF and subsequently produced in 44% overall yield under the action of concentrated sulfuric acid and ultrasoundCoronene. They also address the mass production of perylenes starting from 3,4,9, 10-perylene tetracarboxylic anhydride in Ba (OH)2Under the action of the organic solvent, a large amount of perylene can be obtained under the condition of 400 ℃ for several days. Although the method overcomes the defect of expensive price of the raw material perylene, the process involves multiple anhydrous and anaerobic and low-temperature operations, and the intermediate product is extremely unstable, which brings inconvenience to industrialization.
Disclosure of Invention
The invention aims to provide a novel method for preparing coronene compounds, which adopts alcohol raw materials and takes a silicon-aluminum molecular sieve as a catalyst to synthesize the coronene compounds.
To this end, the present invention provides a process for the preparation of a coronene compound, said process comprising the steps of:
the raw material containing the alcohol compound and a catalyst are contacted and reacted in a reactor to obtain the coronene compound;
wherein the catalyst comprises an activated silicon-aluminum molecular sieve.
In a preferred embodiment, the catalyst consists of an activated aluminosilicate molecular sieve.
In a preferred embodiment, the reaction is followed by a post-treatment to obtain the coronene compound.
In a preferred embodiment, the post-treatment comprises: purifying the product obtained by the reaction in an inorganic strong acid solution to obtain the coronene compound;
preferably, the purification comprises: extracting with an organic solvent;
preferably, the organic solvent comprises one of dichloromethane, chloroform, tetrachloromethane, petroleum ether and diethyl ether.
Preferably, the product is kept stand in inorganic strong acid for 0.5-5 h.
In a preferred embodiment, the strong inorganic acid comprises: at least one of hydrogen fluoride, hydrochloric acid and nitric acid.
In a preferred embodiment, the coronenes are at least two of coronene, 8-hydro-phenyl [ bc ] coronene, methyl-8-hydro-phenyl [ bc ] coronene, and dimethyl-8-hydro-phenyl [ bc ] coronene;
the alcohol compound is at least one selected from methanol, ethanol, propanol, butanol, pentanol and hexanol.
In a preferred embodiment, the feedstock also includes water;
the mass ratio of the water to the alcohol compound is 0-5;
preferably, the mass ratio of the water to the alcohol compound is 0 to 3.
In a preferred embodiment, the feedstock is introduced into the reactor by a carrier gas or vaporized and then introduced into the reactor;
preferably, the carrier gas is selected from at least one of inactive gases.
Preferably, the inert gas includes nitrogen, an inert gas, and the like.
The silicon-aluminum molecular sieve comprises at least one of an RHO molecular sieve, an ITQ-29 molecular sieve, an UZM-9 molecular sieve, an ECR-18 molecular sieve, a ZSM-25 molecular sieve and a KFI molecular sieve;
the activation treatment comprises: heating at 500-600 deg.c in non-active atmosphere.
In a preferred embodiment, the method comprises:
(1) loading a silicon-aluminum molecular sieve catalyst into a reactor, and heating to 500-600 ℃ in an inactive atmosphere to activate the silicon-aluminum molecular sieve catalyst;
(2) adjusting the temperature of the reactor to 450-550 ℃, feeding a raw material containing an alcohol compound into the reactor to be converted on the silicon-aluminum molecular sieve catalyst, and generating a product coronene compound remained in the silicon-aluminum molecular sieve catalyst;
(3) dissolving the silicon-aluminum molecular sieve catalyst in the product of the step (2) in an inorganic strong acid solution, and extracting an organic phase in the inorganic strong acid solution by using an organic solvent to obtain the coronene compound.
In a preferred embodiment, the feed mass space velocity of the raw material is 1-10 h-1；
The reaction temperature is 450-550 ℃;
the reaction pressure is 0.1-0.5 MPa;
preferably, the feeding mass space velocity of the raw materials is 2-5 h-1；
Preferably, the pressure of the reaction is 0.1-0.2 MPa.
In a preferred embodiment, the reactor is a fixed bed reactor or a fluidized bed reactor.
The beneficial effects that this application can produce include:
(1) the method for preparing the coronene compound is simple and feasible, and has the advantages of simple preparation process, mild reaction conditions and easy operation;
(2) the required raw materials are easy to obtain and the cost is low, so the method is suitable for large-scale production.
Drawings
FIG. 1 is an X-ray diffraction pattern of a sample of a synthesized RHO molecular sieve;
FIG. 2 is an X-ray diffraction pattern of a sample of synthesized ITQ-29 molecular sieve;
FIG. 3 is an X-ray diffraction pattern of a sample of a synthesized UZM-9 molecular sieve;
FIG. 4 is an X-ray diffraction pattern of a sample of synthesized ECR-18 molecular sieve;
FIG. 5 is an X-ray diffraction pattern of a sample of a synthesized ZSM-25 molecular sieve;
fig. 6 is an X-ray diffraction pattern of a sample of the synthesized KFI molecular sieve.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
In a preferred embodiment of the present invention, the main steps for preparing coronenes from an alcohol feedstock in the presence of a silicoaluminophosphate molecular sieve catalyst in a fixed bed reactor are as follows:
a certain amount of silicon-aluminum molecular sieve catalyst is filled in a fixed bed reactor, and a catalyst bed layer is heated to a certain temperature between 500 ℃ and 600 ℃ for a period of time, for example, 5-60 min, under the atmosphere of inert gas such as nitrogen or helium, so as to complete the catalyst activation process. Adjusting the temperature of the reactor to a certain temperature between 450 ℃ and 550 ℃, introducing inert gas such as nitrogen or helium carrying alcohol steam or mixed steam of alcohol and water into the reactor to contact and react with the catalyst, and cooling the reactor to room temperature after the reaction is finished. After the reaction is completed, the temperature of the reactor is preferably reduced to room temperature, for example, the catalyst (with the product coronene compound remaining inside) is poured out, the catalyst is placed in a strong acid solution such as a hydrogen fluoride solution or a hydrochloric acid solution for a period of time such as 0.5 to 5 hours, and after all solid substances are dissolved, the organic phase is extracted by using an organic solvent such as carbon tetrachloride or petroleum ether to obtain the coronene compound.
In a preferred embodiment of the present invention, the main steps for preparing coronenes from an alcohol feedstock in the presence of a silicoaluminophosphate molecular sieve catalyst in a fluidized bed reactor are as follows:
a certain amount of the silicon-aluminum molecular sieve microspherical catalyst is filled into a fluidized bed reactor, and the reactor is heated to a certain temperature between 500 ℃ and 600 ℃ under the atmosphere of inert gas such as nitrogen or helium and is kept for a period of time such as 5-60 min, so that the catalyst activation process is completed. The reactor temperature is then adjusted to a temperature between 450 c and 550 c and the alcohol feed is introduced into the vaporization furnace, for example, by a feed pump, where it is vaporized and then fed to the fluidized bed reactor to complete the feed. The alcohol raw material contacts with silicon-aluminium molecular sieve catalyst in the reactor and is converted into coronene compound. Preferably, the mass space velocity of the feeding of the alcohol raw material is 1-10 h-1The reaction pressure is 0.1-0.5 MPa. Preferably cooling to room temperature after the reaction is finished, taking out the catalyst, placing the catalyst in a strong acid solution such as a hydrogen fluoride solution or a nitric acid solution for a period of time such as 0.5-5 h, and extracting an organic phase by using carbon tetrachloride or chloroform after the catalyst is completely dissolved to obtain the product, namely the coronene compoundA compound (I) is provided.
In the present invention, for example, the composition of the organic phase obtained by the extraction is analyzed by an Agilent 7890/5975 chromatograph-mass spectrometer and HP-5 chromatographic column in the examples, and the yield of coronene compound is calculated by combining the weight gain of the catalyst after the reaction (the initial catalyst weight and the catalyst weight after the reaction are determined by an integrated thermal analyzer) and the analysis result of the chromatograph-mass spectrometer, wherein the yield is calculated by the formula:
Yi＝(ΔWcat*Ci)/Fj
Ytatal＝∑Yi
i: the produced coronenes, including coronene, 8-hydro-phenyl [ bc ] coronene, methyl-8-hydro-phenyl [ bc ] coronene, dimethyl-8-hydro-phenyl [ bc ] coronene;
j: alcohols as raw materials including methanol, ethanol, propanol, butanol, pentanol;
ΔWcat: catalyst phase weight gain determined by a comprehensive thermal analyzer;
Ci: chromatographically determining the concentration of a coronene compound in the organic phase;
Fj: the feed amount of alcohol as a raw material;
Yi: the yield of certain coronenes;
Ytotal: total yield of coronenes.
Example 1: synthesis of RHO molecular sieve catalyst
Initial gel molar composition ratio 2N-methylbutylamine (as organic structure directing agent): 3Na2O：0.4Cs2O：Al2O3：10SiO2：110H2And O, mixing metered sodium oxide, cesium oxide, pseudo-boehmite, silica sol and deionized water in a beaker, fully stirring to form gel, then putting the gel into a stainless steel autoclave lined with polytetrafluoroethylene, and keeping the temperature at 100 ℃ for 50 hours. After crystallization, the solid product obtained by separation was washed to neutrality with deionized water, and after drying overnight at 120 ℃ in air, the results of XRD analysis are shown in FIG. 1. As can be seen from the results of FIG. 1, the synthesisThe product of (1) is RHO molecular sieve raw powder, and the raw powder is roasted for 5h at 550 ℃ to obtain the RHO molecular sieve which is marked as catalyst 1.
Example 2: synthesis of ITQ-29 molecular sieve catalyst
1.852, 2-dimethyl-2, 3-dihydro-1H-phenyl [ de ] in initial gel molar composition ratio]Isoquinoline (as organic structure directing agent): 0.2SiO2：0.8GeO2：0.06Al2O3: 0.254-methyl-2, 3,6, 7-tetrahydro-1-hydro, 5-hydro-pyridine [3, 2, 1-ij ]]Quinoline: 0.25 Tetramethylamine: 0.5 HF: 6H2And O, mixing metered silica sol, germanium dioxide, aluminum isopropoxide, an organic structure directing agent, hydrofluoric acid and deionized water in a beaker, fully stirring to form gel, then filling the gel into a stainless steel autoclave lined with polytetrafluoroethylene, and crystallizing at the constant temperature of 135 ℃ for 6 d. Centrifuging at 3000 rpm for 3min, washing the solid product with deionized water to neutrality, and drying in air at 100 deg.C overnight to obtain XRD analysis result shown in FIG. 2. From the results in FIG. 2, it can be seen that the synthesized product is ITQ-29 molecular sieve raw powder, which is calcined at 600 ℃ for 5 hours to obtain ITQ-29 molecular sieve, which is marked as catalyst 2.
Example 3: synthesis of UZM-9 molecular sieve catalyst
Tetraethylammonium hydroxide in the initial gel molar composition ratio 9: 2 tetramethylammonium hydroxide: 0Na2O：Al2O3：16SiO2：62H2And O, mixing measured tetraethyl ammonium hydroxide, tetramethyl ammonium hydroxide (organic structure directing agent), aluminum isopropoxide, silica sol and deionized water in a beaker, fully stirring to form gel, then filling the gel into a stainless steel autoclave lined with polytetrafluoroethylene, and crystallizing at constant temperature for 6 hours at room temperature. Centrifuging at 3000 rpm for 3min, washing the solid product with deionized water to neutrality, and drying in air at 100 deg.C overnight to obtain XRD analysis result shown in FIG. 3. From the results in FIG. 3, it can be seen that the synthesized product was UZM-9 molecular sieve raw powder, which was calcined at 600 ℃ for 5 hours to give UZM-9 molecular sieve, which was designated as catalyst 3.
Example 4: synthesis of ECR-18 molecular sieve catalyst
At the initial gel molar composition ratio of 0.5K2O：1.3(TEA)2O：0.6Na2O：Al2O3：9SiO2：135H2And O, mixing metered potassium oxide, organic structure directing agent, sodium oxide, pseudo-boehmite, silica sol and deionized water in a beaker, fully stirring to form gel, then filling the gel into a stainless steel autoclave lined with polytetrafluoroethylene, and crystallizing at the constant temperature of 100 ℃ for 22 d. After crystallization, the solid product obtained by separation was washed to neutrality with deionized water and dried overnight in air at 100 ℃ with a centrifuge of 3000 rpm for 3min, and the results of XRD analysis are shown in FIG. 4. From the results in FIG. 4, it can be seen that the synthesized product is ECR-18 molecular sieve raw powder, which was calcined at 600 ℃ for 5 hours to obtain ECR-18 molecular sieve, which was noted as catalyst 4.
Example 5: synthesis of ZSM-25 molecular sieve catalyst
1.9Na in initial gel molar composition ratio2O：1Al2O3: 5.2 bromination of tetraethylene amine: 7.2SiO2：390H2And O, mixing metered sodium oxide, pseudo-boehmite, an organic structure directing agent, silica sol and deionized water in a beaker, fully stirring to form gel, then putting the gel into a stainless steel autoclave lined with polytetrafluoroethylene, and carrying out rotary crystallization for 7d at the constant temperature of 135 ℃ and the rotating speed of 60 r/min. After crystallization, the solid product obtained by separation was washed to neutrality with deionized water and dried overnight at 110 ℃ in air, and the results of XRD analysis are shown in FIG. 5. As can be seen from the results in FIG. 5, the synthesized product is ZSM-25 molecular sieve raw powder, which was calcined at 600 ℃ for 5 hours to obtain ZSM-25 molecular sieve, which was marked as catalyst 5.
Example 6: synthesis of KFI molecular sieve catalyst
10SiO in the initial gel molar composition ratio2：1Al2O3：2.1K2O: 0.10 SrO: 0.8618-crown-6-ether; 197H2O mixing measured silica sol, aluminum isopropoxide, potassium oxide, strontium oxide, 18-crown-6-ether (organic structure directing agent) and water in a beaker, fully stirring to form gel, and then filling the gel into a stainless steel autoclave lined with polytetrafluoroethyleneAnd crystallizing at 130 ℃ for 7 d. After crystallization, the solid product obtained by separation was washed to neutrality with deionized water and dried overnight at 110 ℃ in air, and the results of XRD analysis are shown in FIG. 6. From the results in fig. 6, it can be seen that the synthesized product is KFI molecular sieve raw powder, which was calcined at 600 ℃ for 5h to obtain KFI molecular sieve, which was designated as catalyst 6.
The following examples illustrate the preparation of coronenes using the catalysts 1 to 6 prepared above and an alcohol starting material.
Example 7
The catalyst activation process was completed by charging 600mg of the RHO molecular sieve catalyst of example 1 (catalyst 1) in a fixed bed reactor having an internal diameter of 10mm, and heating the reactor to 550 ℃ and holding it for 30min in a nitrogen stream of 155 ml/min. Then the reaction temperature of the reactor is adjusted to 475 ℃, methanol steam is carried into the reactor from a methanol saturation tube which is kept at 25 ℃ by nitrogen flow of 155ml/min to contact and react with the catalyst, the reaction pressure is 0.1MPa, and the reaction mass space velocity is 4h-1. And stopping the reaction after the reaction time reaches 1h, and cooling the reactor to room temperature. Directly pouring out the reacted catalyst (at the moment, the reaction product is remained in the catalyst), taking 10mg of the catalyst, determining the total amount of the catalyst deposition species by a TA Q-600 type comprehensive thermal analyzer, additionally taking 50mg of the catalyst, putting into 1ml of hydrogen fluoride solution (20 wt%), standing for 1h, adding 0.5ml of carbon tetrachloride after all solid substances are dissolved, extracting the organic phase, standing and layering overnight. Then separating the carbon tetrachloride on the lower layer by using a separating funnel to be detected. The reaction conditions and results are shown in table 1.
Examples 8 to 12
The same procedure as in example 7 was followed, except that the ITQ-29 molecular sieve catalyst (catalyst 2), UZM-9 molecular sieve catalyst (catalyst 3), ECR-18 molecular sieve catalyst (catalyst 4), ZSM-25 molecular sieve catalyst (catalyst 5) and KFI molecular sieve catalyst (catalyst 6) prepared in examples 2 to 6 were used as catalysts, respectively, and the hydrogen fluoride solution was replaced with a hydrochloric acid solution and a nitric acid solution in examples 11 and 12, respectively, to prepare the product coronenes, with the reaction conditions and results shown in Table 1.
Examples 13 to 16
The product coronene was prepared by the same procedure as in example 7 except that the reaction temperature of the reactor was adjusted to 425 deg.C, 450 deg.C, 500 deg.C and 525 deg.C, respectively, and the reaction conditions and results are shown in Table 1.
Example 17
The product coronene was prepared following the same procedure as in example 7, except that a mixture of the RHO molecular sieve catalyst of example 1 (catalyst 1) and the ITQ-29 molecular sieve catalyst prepared in example 2 (catalyst 2) was used as the catalyst, wherein the masses of catalyst 1 and catalyst 2 were 300mg and 300mg, respectively, and the reaction conditions and results are shown in Table 1.
Example 18
The product coronene was prepared following the same procedure as in example 7, except that a mixture of the RHO molecular sieve catalyst of example 1 (catalyst 1), the ITQ-29 molecular sieve catalyst prepared in example 2 (catalyst 2), and the ZSM-25 molecular sieve prepared in example 5 (catalyst 5) was used as the catalyst to prepare the coronene compound, wherein the weights of catalyst 1, catalyst 2, and catalyst 5 were 300mg, 150mg, and 150mg, respectively, and the reaction conditions and results are shown in Table 1.
Example 19
10g of RHO molecular sieve microsphere catalyst is loaded into a fluidized bed reactor and treated for 1h in a helium atmosphere at 600 ℃, and then the reaction temperature of the reactor is adjusted to 475 ℃. Introducing methanol and water into preheater via feed pump, vaporizing raw material in the preheater at 250 deg.C, introducing into fluidized bed reactor, contacting methanol steam and water vapor with catalyst in the reactor and fluidizing the catalyst, wherein methanol feeding space velocity is 2 hr-1The mass ratio of water/methanol was 1.5, and the reaction pressure was 0.1 MPa. And stopping the reaction after the reaction time reaches 1h, and cooling the reactor to room temperature. Directly pouring out the reacted catalyst (at this time, the reaction product is remained in the catalyst), taking 10mg of the catalyst, determining the total amount of the catalyst deposit species by TA Q-600 type comprehensive thermal analyzer, additionally taking 50mg of the catalyst, putting into 1ml of hydrogen fluoride solution (20 wt%), standing for 1h, adding into the solution after the solid matter is completely dissolvedThe organic phase was extracted with 0.5ml carbon tetrachloride and allowed to stand overnight for separation. Then separating the carbon tetrachloride on the lower layer by using a separating funnel to be detected. The reaction conditions and results are shown in table 1.
Examples 20 to 24
The coronene product was prepared by the same procedure as in example 19 except that the reaction raw materials were changed to ethanol, propanol, butanol, pentanol and hexanol, respectively, and the reaction conditions and results were as shown in table 1.
Example 25
The same procedures as in example 19 were repeated except that the mass ratio of water to methanol was adjusted to 1, the reaction pressure was adjusted to 0.2MPa, and the reaction mass space velocity was adjusted to 2h-1To prepare the product coronene compound, the reaction conditions and results are shown in table 1.
Example 26
The same procedures as in example 19 were repeated except that the mass ratio of water to methanol was adjusted to 3, the reaction pressure was adjusted to 0.5MPa, and the reaction mass space velocity was adjusted to 10 hours-1To prepare the product coronene compound, the reaction conditions and results are shown in table 1.
Example 27
The same procedure as in example 19 was followed, except that the mass ratio of water to methanol was adjusted to 5 and the reaction mass space velocity was adjusted to 10h-1To prepare the product coronene compound, the reaction conditions and results are shown in table 1.
TABLE 1 reaction conditions and yield of coronenes prepared
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (17)
1. A method for preparing coronenes from an alcohol raw material, which is characterized by comprising the following steps:
the raw material containing the alcohol compound and a catalyst are contacted and reacted in a reactor to obtain the coronene compound;
wherein the catalyst comprises an activated aluminosilicate molecular sieve;
the silicon-aluminum molecular sieve comprises at least one of an RHO molecular sieve, an ITQ-29 molecular sieve, an UZM-9 molecular sieve, an ECR-18 molecular sieve, a ZSM-25 molecular sieve and a KFI molecular sieve;
the alcohol compound is selected from at least one of methanol, ethanol, propanol, butanol, pentanol and hexanol;
the reaction temperature is 450-550 ℃.
2. The method according to claim 1, wherein the reaction is followed by a post-treatment to obtain the coronene compound.
3. The method of claim 2, wherein the post-processing comprises: and (3) purifying the product obtained by the reaction in an inorganic strong acid solution to obtain the coronene compound.
4. The method of claim 3, wherein the purifying comprises: and (4) extracting with an organic solvent.
5. The method of claim 4, wherein the organic solvent comprises one of dichloromethane, chloroform, tetrachloromethane, petroleum ether, and diethyl ether.
6. The process according to claim 3, wherein the strong inorganic acid comprises: at least one of hydrogen fluoride, hydrochloric acid and nitric acid.
7. The method of claim 1, wherein said coronenes comprise coronene, 8-hydro-phenyl [ bc ] coronene, methyl-8-hydro-phenyl [ bc ] coronene, and dimethyl-8-hydro-phenyl [ bc ] coronene.
8. The method of claim 1, wherein the feedstock further comprises water;
the mass ratio of the water to the alcohol compound is 0-5.
9. The method according to claim 8, wherein the mass ratio of the water to the alcohol compound is 0 to 3.
10. The method of claim 1, wherein the feedstock is introduced into the reactor by a carrier gas or vaporized prior to being introduced into the reactor.
11. The method of claim 10, wherein the carrier gas is selected from at least one of an inert gas.
12. The method of claim 1,
the activation treatment comprises: heating at 500-600 ℃ in an inert atmosphere.
13. The method according to claim 1, characterized in that it comprises:
(1) loading a silicon-aluminum molecular sieve catalyst into a reactor, and heating to 500-600 ℃ in an inactive atmosphere to activate the silicon-aluminum molecular sieve catalyst;
(2) adjusting the temperature of the reactor to 450-550 ℃, feeding a raw material containing an alcohol compound into the reactor to be converted on the silicon-aluminum molecular sieve catalyst, and generating a product coronene compound remaining in the silicon-aluminum molecular sieve catalyst;
(3) dissolving the silicon-aluminum molecular sieve catalyst in the product of the step (2) in an inorganic strong acid solution, and extracting an organic phase in the inorganic strong acid solution by using an organic solvent to obtain the coronene compound.
14. The method according to claim 1, wherein the feed mass space velocity of the raw material is 1-10 h-1；
The reaction pressure is 0.1-0.5 MPa.
15. The method according to claim 1, wherein the feed mass space velocity of the raw material is 2-5 h-1。
16. The method according to claim 1, wherein the pressure of the reaction is 0.1 to 0.2 MPa.
17. The method of claim 1, wherein the reactor is a fixed bed reactor or a fluidized bed reactor.
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