CN117229113A - C synthesized from cyclopentanone and methanol 6 -C 9 Aromatic hydrocarbon method - Google Patents
C synthesized from cyclopentanone and methanol 6 -C 9 Aromatic hydrocarbon method Download PDFInfo
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- CN117229113A CN117229113A CN202311064017.9A CN202311064017A CN117229113A CN 117229113 A CN117229113 A CN 117229113A CN 202311064017 A CN202311064017 A CN 202311064017A CN 117229113 A CN117229113 A CN 117229113A
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- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 186
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 160
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000002808 molecular sieve Substances 0.000 claims abstract description 19
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000008569 process Effects 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 239000002994 raw material Substances 0.000 claims description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012495 reaction gas Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000011835 investigation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000006004 Quartz sand Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002028 Biomass Substances 0.000 description 5
- 238000005882 aldol condensation reaction Methods 0.000 description 5
- 238000005899 aromatization reaction Methods 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000006462 rearrangement reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing C from cyclopentanone and methanol 6 ‑C 9 Aromatic hydrocarbon preparation process with cyclopentanone and methanol as material and molecular sieve catalyst in fixed bed reactor 6 ‑C 9 Aromatic hydrocarbons. The invention has simple process route, is environment-friendly, has cheap and easily obtained catalyst, and realizes the conversion of cyclopentanone and methanol to C 6 ‑C 9 Direct complete conversion of aromatic hydrocarbons.
Description
Technical Field
The invention relates to a method for synthesizing C from cyclopentanone and methanol 6 -C 9 Aromatic hydrocarbon method.
Background
C in aromatic hydrocarbons 6 -C 8 Aromatic benzene, toluene and xylene are used as basic organic chemical raw materials in petrochemical industry, have very wide application, can be used for generating various chemical products such as synthetic rubber, synthetic fiber, synthetic resin and the like, can also be used for producing various fine chemical products,can also be used as additive of high-octane gasoline. C (C) 9 Benzene, toluene, xylene can also be produced from aromatic hydrocarbons by dealkylation, transalkylation, and the like. At present, the aromatic hydrocarbon production in China mainly takes a petroleum route as a main part, C 6 -C 9 Aromatic hydrocarbons are also mainly derived from petroleum and coal tar. In recent years, due to the energy structure characteristics of 'rich coal and lean oil' in China, the technology of preparing aromatic hydrocarbon from coal-based methanol is used for partially replacing petroleum resources, and the technology has become an important mode for increasing the yield of aromatic hydrocarbon in China. But with the increasing social concern for sustainable development and environmental problems, green renewable C was developed 6 -C 9 Aromatic hydrocarbon production techniques are necessary.
Biomass energy is taken as the only organic carbon source carrier in renewable energy sources on the earth, and is expected to replace the current energy supply system in the future. Wherein, lignocellulose is not edible, is cheap and easy to obtain, has rich reserves and is a renewable resource with neutral carbon. Therefore, the lignocellulose and the derivative platform chemicals thereof are used as raw materials to produce the aromatic compounds, so that the dependence on petroleum can be reduced, and the method has outstanding significance for deepening energy safety. The subject group has long been engaged in the work of catalytic conversion of biomass, and developed a series of routes for efficient utilization of biomass and its platform compounds. Cyclopentanone is one of the important biomass platform compounds, which can be obtained by selective hydrogenation of furfural and biomass pyrolysis, and can also be directly prepared by one-step selective hydrogenolysis of hemicellulose, xylan, xylose and arabinose in raw materials (Fuel Process.Technol.,2007,88,591;Green Chemistry,2013,15,1932;CN113968776A). Up to now, no document reports the dehydrogenation/aldol condensation/rearrangement/aromatization synthesis of C by taking cyclopentanone and methanol as raw materials 6 -C 9 Aromatic hydrocarbons.
Disclosure of Invention
The invention aims to provide a method for synthesizing C from cyclopentanone and methanol 6 -C 9 A simple and efficient method for aromatic hydrocarbon. The invention takes cyclopentanone and methanol as raw materials, takes molecular sieve as catalyst, and directly synthesizes C through cascade dehydrogenation/aldol condensation/rearrangement/aromatization reaction in a fixed bed continuous reactor 6 -C 9 Aromatic hydrocarbons.
The invention is realized by the following technical scheme:
c synthesized from cyclopentanone and methanol 6 -C 9 The arene preparing process with cyclopentanone and methanol as material includes the cascade dehydrogenation, aldol condensation, rearrangement and aromatization reaction on molecular sieve catalyst to obtain target product C in one step in fixed bed continuous reactor 6 -C 9 Aromatic hydrocarbons.
The raw materials of cyclopentanone, methanol and target product C 6 -C 9 The chemical structural formula of the arene is shown in table 1.
Structural formula of the compound of Table 1
Based on the above scheme, preferably, the molar ratio of cyclopentanone to methanol in the raw material is 1:0.5-10, preferably the molar ratio of cyclopentanone to methanol is between 1:0.75-8, more preferably the molar ratio of cyclopentanone to methanol is between 1:1-6.
Based on the foregoing, preferably, the molecular sieve catalyst comprises one or more of H-ZSM-5, H-USY, H-Y, H-beta, H-MOR, H-ZSM-35, H-MCM-22, H-ZSM-22, and H-ZSM-11.
Based on the above scheme, the molecular sieve preferably has a molar silicon to aluminum ratio of 2 to 500, preferably a molar silicon to aluminum ratio of 2 to 400, more preferably a molar silicon to aluminum ratio of 2 to 300.
Based on the above scheme, the reaction temperature in the fixed bed reactor is preferably 300-600 ℃, preferably 350-550 ℃, and more preferably 400-500 ℃.
Based on the above scheme, the reaction gas in the fixed bed reactor is preferably nitrogen, the pressure is 0.0001-1MPa, the reaction pressure is preferably 0.0001-0.5MPa, and the reaction pressure is more preferably 0.0001-0.1MPa.
Based on the above scheme, the molar ratio of nitrogen to cyclopentanone in the fixed bed reactor is preferably 10-400:1, preferably the molar ratio of nitrogen to cyclopentanone is between 20-300:1, more preferably the molar ratio of nitrogen to cyclopentanone is between 30-200:1.
Based on the above scheme, preferably, the hourly space velocity of cyclopentanone in the fixed bed reactor is 0.01-10h -1 Preferably cyclopentanone, has an hourly space velocity of from 0.05 to 8h -1 More preferably, the cyclopentanone hourly space velocity is in the range of 0.1 to 6h -1 Between them.
The method can realize the one-step high-efficiency conversion of cyclopentanone and methanol into C 6 -C 9 Aromatic hydrocarbons.
The beneficial effects of the invention are as follows: the invention takes cyclopentanone and methanol as raw materials for the first time, and in a fixed bed continuous reactor, C is directly synthesized in one step through cascade dehydrogenation/aldol condensation/rearrangement/aromatization reaction under the action of a molecular sieve catalyst 6 -C 9 Aromatic hydrocarbon, cyclopentanone and methanol to C 6 -C 9 Direct complete conversion of aromatic hydrocarbons; the reaction condition is mild, the catalyst is cheap and easy to obtain, the performance is good, the stability (the reaction for 24 hours is not deactivated) and the regeneration performance are good, the cyclopentanone conversion rate is more than 90%, C 6 -C 9 The aromatic hydrocarbon selectivity is more than 80 percent. The invention has the advantages of simple process route, convenient operation, low energy consumption and environmental protection, is a green and efficient new catalytic route, and can be used for actual industrial production. Up to now, there is no one-step direct synthesis of C from cyclopentanone and methanol by cascade dehydrogenation/aldol condensation/rearrangement/aromatization reactions 6 -C 9 Relevant reports of aromatic hydrocarbons.
Drawings
FIG. 1 shows cyclopentanone and methanol synthesis C 6 -C 9 Gas chromatograms of the products of aromatic hydrocarbons.
FIG. 2 shows the target product C 6 -C 9 Mass spectrum control diagram of aromatic hydrocarbon.
Detailed Description
The technical scheme of the present invention is described in further detail below with reference to specific embodiments, but the scope of the present invention is not limited to these embodiments.
Preparation of C from cyclopentanone and methanol 6 -C 9 Aromatic hydrocarbon experiment, reactor is fixedPumping cyclopentanone/methanol solutions with different molar ratios by a liquid chromatographic pump, and reacting at a set temperature, nitrogen pressure, molar ratio of nitrogen to cyclopentanone and cyclopentanone hourly space velocity by using a molecular sieve as a catalyst.
Examples 1 to 33
Synthesis of C from cyclopentanone and methanol by different catalysts 6 -C 9 Investigation of aromatic reactivity: uniformly mixing 0.45g of one or more catalysts and 2g of quartz sand (40-70 meshes), filling the mixture into a fixed bed continuous reactor, heating the mixture to 450 ℃ at the speed of 10 ℃/min, wherein the molar ratio of cyclopentanone to methanol in the raw material is 1:1, the nitrogen pressure is 0.01MPa, the molar ratio of nitrogen to cyclopentanone is 100:1, and the cyclopentanone hourly space velocity is 0.6h -1 The reaction was carried out under the conditions and the experimental results are shown in Table 2.
TABLE 2 Synthesis of C from cyclopentanone and methanol with different molecular sieve catalysts 6 -C 9 Reactivity of aromatic hydrocarbons
As can be seen from the data in Table 2, the molecular sieve catalysts listed in the table synthesize C for cyclopentanone and methanol 6 -C 9 The reaction of aromatic hydrocarbon has better effect. The silicon-aluminum ratio of different molecular sieves also has a certain influence on the reactivity. Under the action of H-ZSM-5 (21) molecular sieve catalyst, the conversion rate of cyclopentanone is up to 98%, and the target product C 6 -C 9 The aromatic hydrocarbon selectivity also reaches 90 percent.
Examples 34 to 40
Molar ratio of cyclopentanone to methanol in raw materials C 6 -C 9 Investigation of aromatic reactivity: 0.45g of the H-ZSM-5 (21) molecular sieve catalyst used in example 1 above was uniformly mixed with 2g of quartz sand (40-70 mesh), charged into a fixed bed continuous reactor, heated to 450℃at a rate of 10℃per minute, and the nitrogen pressure was controlled to 0.01MPa, the molar ratio of nitrogen to cyclopentanone was 100:1 and the cyclopentanone hourly space velocity was controlled to 0.6H -1 Then, cyclopentanone/methanol solutions with different molar ratios were pumped for reaction, and the experimental results are shown in table 3.
TABLE 3 molar ratio of cyclopentanone to methanol C for cyclopentanone and methanol Synthesis 6 -C 9 Influence of the reactivity of aromatic hydrocarbons
As can be seen from the data in Table 3, the molar ratio of cyclopentanone to methanol in the starting material was compared to the synthesis of C from cyclopentanone and methanol under otherwise identical conditions 6 -C 9 The reactivity of aromatic hydrocarbons has a significant impact. As the proportion of methanol in the raw material increases gradually, the conversion rate of cyclopentanone increases gradually until the cyclopentanone is completely converted, and C 6 -C 9 The aromatic selectivity tends to increase and then decrease.
Examples 41 to 51
Reaction temperature for synthesizing C from cyclopentanone and methanol 6 -C 9 Investigation of aromatic reactivity: 0.45g of the H-ZSM-5 (21) molecular sieve catalyst used in the example above was uniformly mixed with 2g of quartz sand (40-70 mesh), packed in a fixed bed continuous reactor, and heated to the respective temperatures under investigation at a rate of 10 ℃/min, at a cyclopentanone to methanol molar ratio of 1:6, a nitrogen pressure of 0.01MPa, a nitrogen to cyclopentanone molar ratio of 100:1 and a cyclopentanone hourly space velocity of 0.6H -1 The reaction was carried out under the conditions, and the experimental results are shown in Table 4.
TABLE 4 reaction temperature vs. cyclopentanone and methanol Synthesis C 6 -C 9 Influence of the reactivity of aromatic hydrocarbons
As can be seen from the data in Table 4, the reaction temperature was the same for cyclopentanone and methanol to synthesize C 6 -C 9 The reactivity of aromatic hydrocarbons has a significant impact. The reaction temperature increases to some extent to increase the reactivity, but too high a temperature decreases C 6 -C 9 Selectivity to aromatic hydrocarbons.
Examples 52 to 57
Synthesis of C from cyclopentanone and methanol under Nitrogen pressure 6 -C 9 Investigation of aromatic reactivity: 0.45g of the H-ZSM-5 (21) molecular sieve catalyst used in the example above was uniformly mixed with 2g of quartz sand (40-70 mesh), packed in a fixed bed continuous reactor, warmed to 450℃at a rate of 10℃per minute, the molar ratio of cyclopentanone to methanol was controlled to be 1:6, the molar ratio of nitrogen to cyclopentanone was controlled to be 100:1 and the cyclopentanone hourly space velocity was 0.6H -1 The reaction was then carried out under different nitrogen pressures and the experimental results are shown in table 5.
TABLE 5 Nitrogen pressure vs. cyclopentanone and methanol Synthesis C 6 -C 9 Influence of the reactivity of aromatic hydrocarbons
As can be seen from the data in Table 5, the nitrogen pressure had no effect on cyclopentanone conversion, but on C, under otherwise identical conditions 6 -C 9 The aromatic hydrocarbon selectivity has a great influence. With the gradual increase of the nitrogen pressure, C 6 -C 9 The selectivity to aromatics remained almost unchanged and then gradually decreased.
Examples 58 to 64
Molar ratio of Nitrogen to cyclopentanone C synthesis from cyclopentanone and methanol 6 -C 9 Investigation of aromatic reactivity: uniformly mixing 0.45g of H-ZSM-5 (21) molecular sieve catalyst used in the embodiment and 2g of quartz sand (40-70 meshes), filling the mixture into a fixed bed continuous reactor, heating the mixture to 450 ℃ at the speed of 10 ℃/min, and controlling the mol ratio of cyclopentanone to methanolAt a ratio of 1:6, a nitrogen pressure of 0.001 and a cyclopentanone hourly space velocity of 0.6h -1 The reaction was then carried out under different molar ratios of nitrogen to cyclopentanone, and the experimental results are shown in table 6.
TABLE 6 molar ratio of Nitrogen to cyclopentanone C synthesis of cyclopentanone and methanol 6 -C 9 Influence of the reactivity of aromatic hydrocarbons
As can be seen from the data in Table 6, the molar ratio of nitrogen to cyclopentanone was compared with the conversion of cyclopentanone and methanol to C under otherwise identical conditions 6 -C 9 The reaction of aromatic hydrocarbons has little effect.
Examples 65 to 73
Cyclopentanone hourly space velocity versus cyclopentanone and methanol synthesis C 6 -C 9 Investigation of aromatic reactivity: a quantity of the H-ZSM-5 (21) molecular sieve catalyst used in the above example was uniformly mixed with 2g of quartz sand (40-70 mesh), packed in a fixed bed continuous reactor, heated to 450℃at a rate of 10℃per minute, the cyclopentanone to methanol molar ratio was controlled to 1:6, the nitrogen pressure was 0.001 and the nitrogen to cyclopentanone molar ratio was 100:1, and then reacted at different cyclopentanone hourly space velocities, the experimental results are shown in Table 7.
TABLE 7 cyclopentanone hourly space velocity vs. cyclopentanone and methanol Synthesis C 6 -C 9 Influence of the reactivity of aromatic hydrocarbons
Watch with a watchThe data in 7 shows that the cyclopentanone hourly space velocity converts cyclopentanone and methanol to C under otherwise identical conditions 6 -C 9 The reaction of aromatic hydrocarbons has a large influence. The increase in the cyclopentanone hourly space velocity increases C to a certain extent 6 -C 9 Aromatic selectivity, but excessive cyclopentanone hourly space velocity reduces reactivity, cyclopentanone conversion, and C 6 -C 9 The aromatic selectivity is significantly reduced.
Claims (8)
1. C synthesized from cyclopentanone and methanol 6 -C 9 A process for aromatic hydrocarbons, characterized in that said process comprises: cyclopentanone and methanol are used as raw materials, and are converted in one step in a fixed bed continuous reactor under the action of a molecular sieve catalyst to directly obtain C 6 -C 9 Aromatic hydrocarbons.
2. A method according to claim 1, characterized in that: the molar ratio of cyclopentanone to methanol in the raw material is 1:0.5-10, preferably the molar ratio of cyclopentanone to methanol is 1:0.75-8, more preferably the molar ratio of cyclopentanone to methanol is 1:1-6.
3. A method according to claim 1, characterized in that: the molecular sieve catalyst comprises one or more of H-ZSM-5, H-USY, H-Y, H-beta, H-MOR, H-ZSM-35, H-MCM-22, H-ZSM-22 and H-ZSM-11.
4. A method according to claim 1, characterized in that: the molecular sieve has a molar ratio of silicon to aluminum of 2 to 500, preferably a molar ratio of silicon to aluminum of 2 to 400, more preferably a molar ratio of silicon to aluminum of 2 to 300.
5. A method according to claim 1, characterized in that: the reaction temperature in the fixed bed reactor is 300 to 600 ℃, preferably 350 to 550 ℃, more preferably 400 to 500 ℃.
6. A method according to claim 1, characterized in that: the reaction gas in the fixed bed reactor is nitrogen, the pressure is 0.0001-1MPa, the preferable reaction pressure is 0.0001-0.5MPa, and the more preferable reaction pressure is 0.0001-0.1MPa.
7. The method according to claim 5, wherein: the molar ratio of nitrogen to cyclopentanone in the fixed bed reactor is 10-400:1, preferably the molar ratio of nitrogen to cyclopentanone is 20-300:1, more preferably the molar ratio of nitrogen to cyclopentanone is 30-200:1.
8. A method according to claim 1, characterized in that: the hourly space velocity of cyclopentanone in the fixed bed reactor is 0.01-10h -1 Preferably cyclopentanone, has an hourly space velocity of from 0.05 to 8h -1 More preferably cyclopentanone, has an hourly space velocity of from 0.1 to 6h -1 。
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