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Frontiers of Chemical Science and Engineering 2024年第1期18卷 71-84页

作者： Feng Chen Jianing Huo Liang Zhao Jinsen Gao Chunming Xu State Key Laboratory of Heavy Oil Processing China University of PetroleumBeijing 102249China

To enhance the yields of benzene,toluene,and xylene in tetralin hydrocracking,the effect of the support acid properties of NiMo catalysts on hydrocracking performance of tetralin were investigated in this study.NaY zeolites were modified by hydrothermal treatment to form USY zeolites at different temperatures and adjust the type and amount of acid.In addition,H-Beta was loaded into the USY to further adjust the acidic properties of the catalysts.The result shows that when the total B acid content of the catalyst is maintained between 150 and 200μmol·g^(-1),the total acid amount is maintained between 1.7 and 1.9 mmol·g^(-1),and the L/B(L and B acids)ratio is maintained between 1.5 and 2,the catalysts have favorable performances on tetralin hydrocracking.Under this condition,the catalysts have a yield of benzene,toluene,and xylene higher than 30 wt%and a selectivity for benzene,toluene,and xylene higher than 35%.The tetralin conversion is greater than 85 wt%.The AB6 catalyst obtains the best hydrocracking effect with the conversion of tetralin reaching 90.24 wt%,the yields of benzene,toluene,and xylene reaching 33.58 wt%,and the selectivity of benzene,toluene,and xylene reaching 37.21%,respectively.

关键词： hydrocracking tetralin benzene toluene and xylene acid properties reaction pathways

tetralin Hydrocracking Reaction Network to Single-Ring Aromatics on Bifunctional Catalysts

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China Petroleum Processing & Petrochemical Technology 2022年第2期24卷 14-22页

作者： Ju Xueyan Huang Zhen Zhang Rui Wang Lixin Hu zhihai Li Dadong SINOPEC Research Institute of Petroleum Processing Beijing 100083

Conversion of LCO(light cycle oil)to BTX(benzene,toluene,and xylene)is an economically valuable method for refineries.However,this approach still faces difficulties as the main reactions are not clearly understood.Here we study the detailed hydrocracking pathway of typical reactants,1-methylnaphthalene and tetralin,through molecular simulations and experiments to improve our understanding of the conversion process of LCO to BTX.Molecular simulations demonstrate that the rate-determining step is the isomerization pathway of six-membered ring to five-membered ring in tetralin as its activation energy(ΔEa)is the highest among all the reactions and the order ofΔEa of reactions is isomerization>ring-opening≈side-chain cleavage.The results of experiments show that with the increase in reaction depth,i.e.,through a high temperature(350-370℃)and low LHSV(4.5-6.0 h^(−1)),isomerization,ring-opening,and side-chain cleavage reactions occurred,thus improving the selectivity and yield of alkyl aromatics.

关键词： tetralin hydrocracking network single-ring aromatics

Selective catalytic hydrogenation of naphthalene to tetralin over a NiMo/Al2O3 catalyst

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Chinese Journal of Chemical Engineering 2020年第10期28卷 2566-2576页

作者： Xiaoping Su Pu An Junwen Gao RuchengWang Yujuan Zhang Xi Li Yangkun Zhao Yongqi Liu Xiaoxun Ma Ming Sun School of Chemical Engineering Northwest UniversityInternational Science&Technology Cooperation Base of MOST for Clean Utilization of Hydrocarbon ResourcesChemical Engineering Research Center of the Ministry of Education for Advanced Use Technology of Shanbei EnergyShaanxi Research Center of Engineering Technology for Clean Coal ConversionCollaborative Innovation Center for Development of Energy and Chemical Industry in Northern ShaanxiXi'an 710069China Shaanxi Yanchang Petroleum(Group)Co. Ltd.Xi'an 710069China

The selective catalytic hydrogenation of naphthalene to high-value tetralin was systematically investigated.A series of Al2O3 catalysts containing different active metals(Co,Mo,Ni,W)were prepared by incipient wetness impregnation.The effects of different active metals forms(oxidation,reduction,sulfuration)and reaction conditions on naphthalene hydrogenation were investigated and the catalysts were characterized by XRD,XPS,BET,NH3-TPD and SEM.Especially,Ni-Mo/Al2O3 was first used in this reactive system.The results show that the oxidative4%Ni O-20%MoO3/Al2O3 is the best catalyst for the preparation of tetralin.The conversion of naphthalene and the selectivity of tetralin can reach 95.62%and 99.75%respectively at 200℃,8 h and 6 MPa.Compared with reduced and sulfureted 4%Ni O-20%MoO3/Al2O3 catalysts,oxidative 4%Ni O-20%MoO3/Al2O3 has a well dispersed and uniform monolayer of the active metals,larger pore volume and size,and larger total acidity.NiO-MoO3/Al2O3 has a synergistic effect between NiO activity and MoO3 selectivity.

关键词： Naphthalene tetralin Ni-Mo/Al2O3 catalysts

Preparation of a highly efficient Pt/USY catalyst for hydrogenation and selective ring-opening reaction of tetralin

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Petroleum Science 2018年第3期15卷 605-612页

作者： Qi Wang Zhang-Gui Hou Bo Zhang Jian Liu Wei-Yu Song De-Sheng Xue Li-Zhi Liu Dong Wang Xin-Guo Chen State Key Laboratory of Heavy Oil Processing and Beijing Key Laboratory of Oil and Gas Pollution Control China University of Petroleum Beijing 102249 China CNOOC Research Institute of Oil and Petrochemicals Beijing 102249 China

Ultrastable Y zeolite（USY）-supported Pt catalyst was prepared by gas-bubbling-assisted membrane reduction. The influence of reaction conditions and the metal and acid sites of catalysts on the catalytic performance of catalyst in hydrogenation and selective ring opening of tetralin, 1,2,3,4-tetrahydronaphthalene（THN）, was studied. It was found that the optimal reaction conditions were at a temperature of 280 °C, hydrogen pressure of 4 MPa, liquid hourly space velocity of 2 h^-1 and H2/THN ratio of 750. Under these optimal conditions, a high conversion of almost 100% was achieved on the 0.3 Pt/USY catalyst. XRD patterns and TEM images revealed that Pt particles were highly dispersed on the USY, favorable to the hydrogenation reaction of tetralin. Ammonia temperature-programmed desorption and Py-IR results indicated that the introduction of Pt can reduce the acid sites of USY, particularly the strong acid sites of USY. Thus, the hydrocracking reaction can be suppressed.

关键词： Hydrogenation and selective ring opening Reaction conditions Supported Pt catalyst tetralin

Effects of some Nitrogen Bases on the Oxygenation of tetralin with Sodium Periodate Catalyzed by Manganese（Ⅲ）meso- Tetraphenylporphyrin as a Model Compound of Cytochrome P-450

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Chinese Journal of Chemistry 2007年第7期25卷 1031-1035页

作者： REZA, Tayebee Department of Chemistry Sabzevar Teacher Training University Sabzevar 397 Iran

The effect of some nitrogen bases on the oxygenation of tetralin by sodium periodate, catalyzed by Mn（TPP）OAc, was evaluated. A series of eight bases, including imidazole, pyridine, and quinuclidine, was used. Binding of axial ligand to the four-coordinate Mn（Ⅲ）-center influenced the efficiency and selectivity of the catalytic oxygenation system.

关键词： nitrogen donor sodium periodate oxidation manganese porphyrin tetralin

Diffusion and Adsorption of tetralin Hydrocracking Reaction on Different Zeolites by Molecular Simulation

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China Petroleum Processing & Petrochemical Technology 2021年第1期23卷 1-9页

作者： Sun Lijie Fan Yaming Dong Songtao Xian Ce Long Xiangyun Li Dadong SINOPEC Research Institute of Petroleum Processing Beijing 100083

Three different zeolite catalysts with different pore sizes(MFI-type,BEA-type,and FAU-type zeolites)have been prepared.The influence of different zeolite catalysts on reactivity and product shape selectivity of tetralin is investigated.Clear differences are observed in the reactivity of tetralin and distribution of products achieved by different catalysts.The diffusion and adsorption behavior of the reactant tetralin and its intermediates,n-butylbenzene and 1-methylindane under the reaction conditions are simulated using molecular simulation methods.Upon combining simulation results and experimental observations,it is shown that the difference in diffusion coefficient and competitive adsorption capacity can explain the reactivity of tetralin and the selectivity of products.The steric hindrance of the MFI-type zeolite mainly limits the key step of ring opening of tetralin,leading to lower selectivity of ring-opening products.n-Butylbenzene molecules can diffuse sufficiently fast in the large pores of FAU-type zeolite and the weak adsorption capacity of n-butylbenzene leads to its insufficient cracking.In addition,it also explains the reason that the BEA-type zeolite has the best BTX selectivity,because it can satisfy both good ring-opening activity and sufficient butylbenzene cracking depth.

关键词： hydrocracking tetralin molecular simulation diffusion competitive adsorption.

Research Progress in Catalytic Cracking Reaction of tetralin and Decalin

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China Petroleum Processing & Petrochemical Technology 2017年第4期19卷 47-54页

作者： Li Xiao Xie Chaogang Wei Xiaoli SINOPEC Research Institute of Petroleum Processing Beijing 100083

The integrated catalytic hydrogenation and catalytic cracking process has been gradually adopted by refineries to satisfy the requirements for manufacture of light and clean petroleum products. To explore the reaction laws of hydrogenated aromatics in hydrotreated oil, the catalytic cracking reaction laws of hydrogenated aromatics have been reviewed by taking tetralin and decalin as examples of different degrees of hydrogenated aromatics. Moreover, the reaction mechanism of tetralin and decalin has been analyzed emphatically. The effects of zeolite pore structure, acid properties and process parameters on reaction laws have been analyzed carefully. It is considered that the catalytic cracking performance of hydrogenated aromatics with different hydrogen saturation degrees is quite different. It is necessary to control the hydrogenation depth, optimize the hydrocarbon composition of catalytic cracking feed materials for maximizing the yield of target products.

关键词： tetralin decalin catalytic cracking reaction mechanism zeolite process parameters

[Cu(2,2'-bpy)Cl_2]和[Cu(1,10-phen)Cl_2]在多金属氧酸盐上的多相化:选择性氧化四氢化萘的新催化剂(英文)

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催化学报 2011年第5期32卷 807-811页

作者： M. BOLTZ A. BLANC G. LAUGEL P.PALE B. LOUIS Laboratoire de Synthkse et Reactivite Organiques Institut de Chimie UMR 7177 CNRS Universitd de Strasbourg 4 rue Blaise Pascal 67000 Strasbourg Cedex France

Mononuclear Cu(II)bipyridine(1)and phenantroline complexes(2)were synthesized and immobilized by different procedures on H3PW12O40 polyoxometalate(POM).Characterization by XRD and SEM-EDX were performed to assess the preservation of the Keggin structure and stoichiometry of the complex.The immobilized complexes were tested as heterogeneous catalysts for the partial oxidation of tetralin(1,2,3,4-tetrahydronaphthalene)using hydrogen peroxide as oxidant in acetonitrile/water as solvent.[Cu(2,2'-bpy)Cl][H2PW12O40] and[Cu(1,10-phen)Cl][H2PW12O40]oxidized tetralin at room temperature,with 16%conversion with(2),to 1-tetralone and 2-tetralone with 83%selectivity.However,the selectivity for 1-tetralone was only 56%.Different preparation methods for the heterogenization of these complexes on the POM Keggin unit were compared and used to enhance the selectivity to 1-tetralone to 75%.

关键词： tetralin partial oxidation Cu(II)complexes 2,2’-bipyridine 1,10-phenantroline hydrogen peroxide polyoxometalate