CN108530247B - Method for preparing cyclohexylbenzene by alkylating cyclohexene and benzene - Google Patents
Method for preparing cyclohexylbenzene by alkylating cyclohexene and benzene Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7007—Zeolite Beta
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The invention relates to a method for preparing cyclohexylbenzene by alkylating cyclohexene and benzene, which comprises the step of contacting benzene and cyclohexene with a molecular sieve catalyst to synthesize cyclohexylbenzene under effective reaction conditions; characterized in that the concentration of the oxygen-containing compound in cyclohexene is controlled such that the concentration of the oxygen-containing compound in cyclohexene is less than 1 wt.%. The method can be used in the industrial production of producing the cyclohexylbenzene from the benzene and the cyclohexene.
Description
Technical Field
The invention relates to a method for preparing cyclohexylbenzene by alkylating cyclohexene and benzene.
Background
The cyclohexylbenzene is an important fine chemical intermediate, has a high boiling point and a condensation point close to room temperature, and has special physical and chemical properties. Cyclohexylbenzene has been widely used in the battery industry as an additive in lithium ion battery electrolytes, has overcharge prevention properties, and can improve the safety of batteries. In addition, cyclohexylbenzene can also be used for synthesizing liquid crystal materials.
The peroxidation of cyclohexylbenzene can produce phenol and cyclohexanone. Phenol is widely used as an important product in the chemical industry. At present, the industrial production mainly adopts the peroxidation and acid decomposition reaction of cumene to prepare phenol, but a large amount of acetone is generated as a byproduct in the reaction process. Compared with the process for preparing phenol by the cyclohexylbenzene oxidation method, the oxidation products of the cyclohexylbenzene are phenol and cyclohexanone. The latter is an important raw material for producing caprolactam and nylon, so the route has no utilization problem of byproducts.
Document US5053571 discloses a process for preparing cyclohexylbenzene by hydroalkylation of benzene over a Ru and Ni loaded Beta molecular sieve. Document US5146024 discloses a process for preparing cyclohexylbenzene by benzene hydroalkylation, using a catalyst of metal Pd supported on an X or Y molecular sieve, the catalyst being modified with an alkali metal or a rare earth metal. The exxonmobil company uses MCM-22 family molecular sieves and catalytic systems of at least one hydrogenation metal (Ni, Pd, Pt and Ru) in a hydrogen atmosphere for hydroalkylation reactions, US6037513, US7579511, US7847128, US7910778, US8084648, US8106243, US8178728, US8329956, US8519194, US20100191017, US20110015457, US20110288341, US20120178969 and CN101687728, CN101754940, CN101796000, CN101925561, CN101998942, CN102015589, CN102177109 and CN 103261126. The reaction conditions are as follows: the temperature is 140-175 ℃, the pressure is 931-1207 KPa, the molar ratio of hydrogen to benzene is 0.3-0.65 and 0.26-1.05 hours-1The weight hourly space velocity of benzene. The highest yield of cyclohexylbenzene was about 40%. The above patents all use noble metal catalysts, so the production cost is high. Patent US20120157718 discloses a method for preparing cyclohexylbenzene by alkylation of benzene and cyclohexene using Y molecular sieve and benzene hydroalkylation reaction of Y molecular sieve loaded with hydrogenation metal (Ni, Pd, Pt and Ru). Among them, the alkylation reaction has a larger benzene-to-olefin ratio (5-30), resulting in a lower cyclohexylbenzene yield and an increase in the cost of product separation.
Documents CN1982264 and CN198226 use a process for the preparation of cyclohexylbenzene by alkylation with benzene and a halocyclohexane or cyclohexanol. However, the price of the halogenated cyclohexane and cyclohexanol is relatively high, and the catalyst used is relatively corrosive to the reaction apparatus. Patent CN101219922 discloses a method for preparing cyclohexylbenzene by using imidazole ionic liquid and metal halide or triacetate ionic liquid and metal halide as catalysts. CN101811924 uses toluene sulfonic acid and pyridine ionic liquid as alkylation catalyst. However, ionic liquids are relatively expensive and not suitable for industrial applications, and the cost of product separation is increased.
Disclosure of Invention
The invention aims to provide a novel method for preparing cyclohexylbenzene by alkylating cyclohexene and benzene. The method has the characteristic of long service life of the catalyst.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a method for preparing cyclohexylbenzene by cyclohexene and benzene alkylation comprises the step of contacting benzene and cyclohexene with a molecular sieve catalyst under effective reaction conditions to synthesize cyclohexylbenzene; wherein the concentration of the oxygen-containing compound in cyclohexene is controlled such that the concentration of the oxygen-containing compound in cyclohexene is less than 1 wt%.
In one embodiment of the present invention, the concentration of the oxygen-containing compound in cyclohexene is preferably controlled to be 0 to 1% by weight.
In one embodiment of the present invention, the concentration of the oxygen-containing compound in cyclohexene is preferably controlled to be 0 to 0.75% by weight.
In one embodiment of the present invention, the concentration of the oxygen-containing compound in cyclohexene is preferably controlled to be 0 to 0.5 wt%.
In one embodiment of the present invention, the concentration of the oxygen-containing compound in cyclohexene is preferably controlled to be 0.01ppm to 1% by weight.
In the above technical solution, the oxygen-containing compound is derived from a product of a reaction of cyclohexene and oxygen.
In the above technical scheme, the oxygen-containing compound includes at least one of cyclohexene oxide, cyclohexanone, cyclohexanol, cyclohexenol, cyclohexenone, and cyclohexene diol.
In the technical scheme, the molecular sieve catalyst comprises the following components in percentage by weight: a) 40-90% of zeolite molecular sieve; and b) 10-60% of a binder.
In the above technical scheme, the molecular sieve is selected from at least one of molecular sieves with MWW, BEA, MOR and FAU topological structures; at least one of MCM-22, MCM-49, MCM-56, mordenite, Beta molecular sieves and Y-type molecular sieves is preferred.
In the above technical scheme, the molecular sieve has SiO2/Al2O3The molar ratio is 5 to 100, preferably 10 to 80.
In the above technical scheme, the effective reaction conditions include: the reaction temperature is 100-250 ℃, preferably 120-220 ℃, and the reaction pressure is 0.5-4.0 MPa, preferably 1.0-3.0 MPa; the benzene/cyclohexene molar ratio is 1.0-10.0, preferably 2.0-8.0; the weight airspeed of cyclohexene is 0.1-2 hours-1Preferably 0.2 to 1 hour-1。
In the above technical solution, the binder is at least one selected from alumina, titania, zinc oxide and zirconia.
In the above technical solution, the step of rectifying the cyclohexene containing the oxygen-containing compound is performed to control the concentration of the oxygen-containing compound in the cyclohexene to be less than 1 wt%.
In the above solution, cyclohexene comprising an oxygen-containing compound is contacted with a guard bed of activated alumina to control the concentration of the oxygen-containing compound in the cyclohexene to less than 1 wt%.
The inventor researches and discovers that when benzene and cyclohexene are subjected to alkylation reaction under the action of a molecular sieve solid acid catalyst to prepare cyclohexylbenzene, due to the active property of the cyclohexene, oxygen-containing compounds such as cyclohexene oxide, cyclohexanone, cyclohexanol, cyclohexenol, cyclohexenone, cyclohexene glycol and the like are easily generated after the cyclohexene contacts with air. The presence of these oxygenates can poison solid acid catalysts, causing a decrease in catalyst stability. The method controls the concentration of the oxygen-containing compound in the cyclohexene, so that the concentration of the oxygen-containing compound in the cyclohexene is lower than 1 weight percent, the service life of the catalyst can be at least improved by 200 percent, and a better technical effect is achieved.
The invention is further illustrated by the following examples.
Detailed Description
[ example 1 ]
Synthesizing the MCM-56 molecular sieve with the MWW topological structure.
600g of 40 wt% silica sol was taken, and 700 g of water and 38.9g of sodium metaaluminate (Al) were added2O342 wt%) and 2 g of sodium hydroxide, and 125 g of Hexamethyleneimine (HMI) are added after stirring. Aging the mixture at room temperature for 100h, crystallizing at 138 deg.C, crystallizing for 40 hr, washing with distilled water to neutrality, and oven drying. X-ray powder diffraction (XRD) results showed that the synthesized product was MCM-56. Wherein the reaction mixture comprises SiO in terms of molar ratio2/Al2O3Is 25, OH-/SiO2Is 0.093, H2O/SiO2Is 14.72, HMI/SiO2Is 0.32. The obtained MCM-56 molecular sieve has the silica-alumina molar ratio SiO2/Al2O324.5, the crystallinity of the MCM-56 molecular sieve is 99.8%.
A50 g sample of the dried powder was taken, exchanged 4 times with 1M ammonium nitrate, filtered and dried. Then fully mixing with 20g of alumina, adding 5 wt% of nitric acid, kneading, extruding into strips with the diameter of 1.6 multiplied by 2mm, drying at 120 ℃ for 12 hours, and roasting at 520 ℃ for 6 hours to prepare the required catalyst.
[ example 2 ]
MCM-22 molecular sieve with MWW topological structure is synthesized.
Sodium aluminate (Al)2O3 35.21wt％，Na2O31.12 wt.%) 14.5 g was dissolved in 990 g of water, 6.18 g of sodium hydroxide was added and dissolved, 49.5 g of hexamethyleneimine, an organic amine template, and silica sol (SiO 1) were added with stirring240 wt%) 150 g, and the material ratio (mol ratio) of the reactants is SiO after uniform stirring2/Al2O3＝20，OH-/SiO2＝0.3，R/SiO2＝0.5，H2O/SiO260. Stirring for 30min, loading into stainless steel reactor, and crystallizing at 150 deg.C for 30 hr while stirring. Then cooling and passingThe crystallized solid product was filtered and the crystallization mother liquor was recovered. And filtering, washing and drying the solid crystallization product. The obtained crystal was MCM-22 as determined by X-ray diffractometry. Obtaining SiO by chemical analysis2/Al2O3The molar ratio was 18.
A50 g sample of the dried powder was taken, exchanged 4 times with 1M ammonium nitrate, filtered and dried. Then, the catalyst is fully mixed with 20g of alumina, 5 wt% of nitric acid is added for kneading, and the mixture is extruded into a bar with the diameter of 1.6 multiplied by 2mm, dried at 120 ℃ for 12 hours and roasted at 520 ℃ for 6 hours to prepare the required catalyst.
[ example 3 ]
Beta molecular sieves with BEA topology were synthesized.
600g of 40 wt.% silica sol, 38.9g of sodium aluminate (alumina content 42 wt.%), 70.6g of 25 wt.% tetraethylammonium hydroxide (TEAOH), 5.0g of Diethylamine (DEA), 168.0g of tetraethylammonium bromide (TEABr), 16.0g of sodium hydroxide, 136.0g of 25 wt.% ammonium hydroxide, and 925.1g of water were mixed and stirred uniformly at normal temperature. Then transferring the mixture into a stainless steel autoclave, and reacting for 50 hours at the crystallization temperature of 155 ℃. After the reaction is finished, the crystallization product is filtered, washed and dried. Wherein SiO is calculated by molar ratio in the reaction mixture2/A12O3＝35，TEAOH/SiO2＝0.05，DEA/SiO2＝0.01，TEABr/SiO2＝0.3，NaOH/SiO2＝0.05，NH4OH/SiO2＝0.2，H2O/SiO225, R1/R2 is 0.2. The crystal product obtained by XRD powder diffraction analysis of the product is Beta zeolite, and the grain diameter of the crystal product is 10-40 nm by transmission electron microscope TEM analysis. Obtaining SiO by chemical analysis2/Al2O3The molar ratio was 20.
A50 g sample of the dried powder was taken, exchanged 4 times with 1M ammonium nitrate, filtered and dried. Then, the catalyst is fully mixed with 20g of alumina, 5 wt% of nitric acid is added for kneading, and the mixture is extruded into a bar with the diameter of 1.6 multiplied by 2mm, dried at 120 ℃ for 12 hours and roasted at 520 ℃ for 6 hours to prepare the required catalyst.
[ example 4 ]
Synthesizing the Y-type molecular sieve with the FAU topological structure.
First, a colloidal directing agent was prepared, and 20.0g H was added2Dissolving 4.0g of NaOH and 2.1g of sodium aluminate (20% solution) solution fully and mixing uniformly, then gradually adding 22.7g of silicic acid into the solution under stirring, fully oscillating for 1h at room temperature, and aging overnight at room temperature; 261.9g H2O, 0.28g NaOH and 20.6g sodium aluminate are fully mixed and dissolved, 284.8g silicic acid is gradually added into the mixed solution in batches under full stirring and is violently shaken for 1 hour, and 50g prepared directing agent is added into the mixed solution and is shaken for 1 hour. The material was then transferred to a stainless steel reaction kettle. Crystallizing at 100 deg.C for 10 hr, filtering, washing, and drying. The crystal product obtained by XRD powder diffraction analysis is Y-type molecular sieve.
A50 g sample of the dried powder was taken, exchanged 4 times with 1M ammonium nitrate, filtered and dried. Then fully mixing with 20g of alumina, adding 5 wt% of nitric acid, kneading, extruding into strips with the diameter of 1.6 multiplied by 2mm, drying at 120 ℃ for 12 hours, and roasting at 500 ℃ for 6 hours to prepare the required catalyst.
[ example 5 ]
Synthesizing the mordenite type molecular sieve with MOR topological structure.
19g of NaOH are dissolved in 40g H with stirring2In O, mixing 14.3 sodium aluminate with the NaOH solution, and stirring until the sodium aluminate is completely dissolved. Adding 497gH into the above mixed solution2Diluting O, adding 245.5g of 40 wt.% silica sol into the solution, stirring for 30min, transferring the solution into a stainless steel autoclave, crystallizing at 170 ℃, and reacting for 24 h. After the reaction is finished, the crystallization product is filtered, washed and dried. The crystalline product obtained by XRD powder diffraction analysis is mordenite.
A50 g sample of the dried powder was taken, exchanged 4 times with 1M ammonium nitrate, filtered and dried. Then, the catalyst was thoroughly mixed with 20g of alumina, and kneaded with 5 wt% nitric acid, extruded into a rod of phi 1.6X 2mm, dried at 120 ℃ for 12 hours, and calcined at 500 ℃ for 6 hours to prepare the desired catalyst.
[ example 6 ]
4.0g of the catalysts [ examples 1 to 5 ] were packed in each of the fixed bedsIn the bed reactor, a mixture of cyclohexene and benzene was then fed, the cyclohexene mass fraction in the mixture being 19.1%. Wherein the mass fraction of the oxygen-containing compound in the cyclohexene is 0.3 wt%. The reaction conditions are as follows: the weight space velocity of the cyclohexene is 0.4h-1The reaction temperature is 170 ℃ and the reaction pressure is 2.0 MPa. The reaction results are shown in table 1.
TABLE 1
[ example 7 ]
4.0g of the synthesized catalyst [ examples 1-5 ] was charged in a fixed bed reactor, respectively, and then a mixed material of cyclohexene and benzene was fed, the mass fraction of cyclohexene in the mixture was 19.1%, wherein the mass fraction of oxygen-containing compounds in cyclohexene was 0.6 wt%. The reaction conditions are as follows: the weight space velocity of the cyclohexene is 0.4h-1The reaction temperature is 170 ℃ and the reaction pressure is 2.0 MPa. The reaction results are shown in table 2.
TABLE 2
[ COMPARATIVE EXAMPLES ]
4.0g of the synthesized catalyst [ examples 1-5 ] was charged in a fixed bed reactor, respectively, and then a mixed material of cyclohexene and benzene was fed, the mass fraction of cyclohexene in the mixture was 19.1%, wherein the mass fraction of oxygen-containing compounds in cyclohexene was 1.5 wt%. The reaction conditions are as follows: the weight space velocity of the cyclohexene is 0.4h-1The reaction temperature is 170 ℃ and the reaction pressure is 2.0 MPa. The reaction results are shown in Table 3.
TABLE 3
Claims (10)
1. Cyclohexene and phenylalkaneA method for preparing cyclohexylbenzene by alkylation comprises the step of contacting benzene and cyclohexene with a molecular sieve catalyst to synthesize cyclohexylbenzene under effective reaction conditions; the method is characterized in that the concentration of an oxygen-containing compound in cyclohexene is controlled to be 0.01 ppm-0.6 wt%, and the effective reaction conditions comprise: the reaction temperature is 100-250 ℃, and the reaction pressure is 0.5-4.0 MPa; the benzene/cyclohexene molar ratio is 1.0-10.0; the weight airspeed of cyclohexene is 0.1-2 hours-1；
The oxygen-containing compound comprises at least one of cyclohexene oxide, cyclohexanone, cyclohexanol, cyclohexenol, cyclohexenone and cyclohexene diol.
2. The process for the alkylation of cyclohexene and benzene to produce cyclohexylbenzene as claimed in claim 1, wherein the molecular sieve catalyst comprises the following components in weight percent: a) 40% -90% of zeolite molecular sieve; and b)10% -60% of a binder.
3. The process for the alkylation of cyclohexene and benzene to produce cyclohexylbenzene, as recited in claim 1, wherein said molecular sieve is selected from at least one molecular sieve having MWW, BEA, MOR and FAU topology.
4. The process for the alkylation of cyclohexene and benzene to produce cyclohexylbenzene as claimed in claim 3, wherein the molecular sieve is selected from at least one of MCM-22, MCM-49, MCM-56, mordenite, a Beta molecular sieve and a Y-type molecular sieve.
5. The process for producing cyclohexylbenzene by the alkylation of cyclohexene and benzene according to claim 1, wherein the molecular sieve has SiO in it2/Al2O3The molar ratio is 5 to 100.
6. The process for producing cyclohexylbenzene by the alkylation of cyclohexene and benzene according to claim 5, wherein the molecular sieve has SiO in it2/Al2O3The molar ratio is 10-80.
7. The process for producing cyclohexylbenzene by alkylation of cyclohexene and benzene according to claim 6, wherein the effective reaction conditions include: the reaction temperature is 120-220 ℃, the reaction pressure is 1.0-3.0 MPa, the benzene/cyclohexene molar ratio is 2.0-8.0, and the weight space velocity of the cyclohexene is 0.2-1 hour-1。
8. The process for the alkylation of cyclohexene and benzene to produce cyclohexylbenzene as claimed in claim 2, wherein the binder is selected from at least one of alumina, titania, zinc oxide and zirconia.
9. The process for preparing cyclohexylbenzene by the alkylation of cyclohexene and benzene as claimed in claim 1, wherein the step of rectifying cyclohexene including oxygen-containing compound is carried out to control the concentration of oxygen-containing compound in cyclohexene to be 0.01ppm to 0.6 wt%.
10. The process for the alkylation of cyclohexene and benzene to produce cyclohexylbenzene as claimed in claim 1, wherein cyclohexene containing oxygen-containing compounds is contacted with a guard bed of activated alumina to control the concentration of oxygen-containing compounds in cyclohexene to be in the range of 0.01ppm to 0.6 wt%.
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| CN105585416A (en) * | 2014-10-20 | 2016-05-18 | 中国石油化工股份有限公司 | Method for alkylation reaction between oxygen-containing component and aromatic hydrocarbon |
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| US9233887B2 (en) * | 2010-12-21 | 2016-01-12 | Exxonmobil Chemical Patents Inc. | Process for producing a monocycloalkyl-substituted aromatic compound |
| CN103539600B (en) * | 2012-07-12 | 2015-06-10 | 中国石油化工股份有限公司 | Aromatic hydrocarbon liquid phase alkylation method |
| WO2014028139A1 (en) * | 2012-08-14 | 2014-02-20 | Exxonmobil Chemical Patents Inc. | Process for producing cyclohexylbenzene |
| CN104513122B (en) * | 2013-09-27 | 2016-05-25 | 中国石油化工股份有限公司 | A kind of method of benzene and cyclohexene liquid-phase alkylation synthesizing cyclohexyl benzene |
| CN104513123B (en) * | 2013-09-27 | 2016-05-25 | 中国石油化工股份有限公司 | A kind of method of benzene and cyclohexene liquid-phase alkylation synthesizing cyclohexyl benzene |
| CN105367371B (en) * | 2014-08-27 | 2018-01-09 | 中国石油化工股份有限公司 | The method of liquid-phase alkylation cyclohexyl benzene |
| CN106518600B (en) * | 2015-09-15 | 2020-02-07 | 中国石油化工股份有限公司 | Method for preparing cyclohexylbenzene by liquid phase alkylation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102066291A (en) * | 2008-04-18 | 2011-05-18 | 道达尔石化法国公司 | Alkylation of aromatic substrates and transalkylation process |
| CN105585416A (en) * | 2014-10-20 | 2016-05-18 | 中国石油化工股份有限公司 | Method for alkylation reaction between oxygen-containing component and aromatic hydrocarbon |
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