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CHEMICAL ENGINEERING SCIENCE · 2023 · IF 4.7

Understanding the catalytic behavior of ionic liquids in tetralin alkylation with α-olefins through experiment and COSMO-RS model

Chen Chen,Xudong Zhang,Qiong Tang,Mingxing Tang,Xuekuan Li,Lei Liu,Jinxiang Dong

Using coal-based feedstocks to produce chemicals is of importance for the high value-added utilization of coal and the reduction of petroleum consumption. Alkyltetralins similar to naphthenic oil were successfully obtained through tetralin alkylation with various olefins. Various ionic liquids (ILs) were applied to catalyze alkylations, and Et 3 NHCl-AlCl 3 IL exhibited high catalytic activity under mild reaction temperature (80 °C), the selectivity of multi-alkyltetralins higher than 70% could be achieved at >99% tetralin conversion. Such catalyst was shown to be robust in the presence of trace water and oxygenated chemicals. COSMO-RS model was applied to predict the mutual solubility and interaction of tetralin, olefins and alkyltetralins in ILs. The experimental and calculated results demonstrated that the favorable interactions of shorter-chain olefins and ILs benefited to produce multi-alkyltetralins, and the low mutual solubility of reactants and products in ILs was helpful to the rapid separation of products in the system.

研究领域: 化学工程 · 催化科学 · 煤化工
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Lubricants · 2022 ·Vol. 10 ·期 11 ·287 · IF 3.584

Alkylation of Tetralin with Butene/Propylene Catalyzed by Ionic Liquid and Its Lubricating Properties

Jiajia Fu,Chen Chen,Qiong Tang,Hong Xu,Lei Liu,Jinxiang Dong

Alkyltetralins similar to naphthenic base oil were successfully synthesized by Friedel–Crafts alkylation of tetralin with short-chain α-olefins (C3/C4), where the applied chemical feedstock could be obtained from coal chemical industry with ease. The Et3NHCl-AlCl3ionic liquid (IL) as catalyst exhibited excellent catalytic performance for alkylation of tetralin withn-butene or propylene. The reaction conditions were investigated in detail to achieve the high selectivity toward multi-alkyltetralins, and the selectivity for multi-alkyltetralins could reach as high as 90% with the complete conversion of tetralin. For comparison, three alkyltetralins with various side-chain alkyl groups and number of side-chains on tetralin were isolated, which behaved as lubricating base oils for investigation. The synthetic oils exhibited an excellent low temperature fluidity, and good potential for compatibility with additives. Di-propyltetralins (DPT) and di-butyltetralins (DBT) displayed the lower friction and wear values than mono-butyltetralins (MBT), which had comparable tribological properties to the commercial naphthenic base oil 4006 (N4006).

研究领域: 化学工程 · 催化 · 润滑科学
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JOURNAL OF POROUS MATERIALS · 2024 ·Vol. 31 ·期 3 ·913-922 · IF 2.5

Synthesis of CuI-modified thiol-functionalized MCM-41 silica-based materials and their catalytic tetralin performance

Wu Chengqiang,Li Yingping,Ma Yongping,Lei Yuexiang,Wang Meijing,Chen Zhen

A novel loaded copper ion catalyst, Cu/MCM-41-SH, was synthesized using CuI-modified thiol-functionalized MCM-41 silica-based materials, and the prepared catalysts were characterized by XPS, FT-IR, SEM and N 2 adsorption–desorption techniques. The XPS results indicated that the chemical valence of the copper that adsorbed on the CuI/MCM-41-SH surface was + 1 valence. N 2 adsorption–desorption showed that the adsorption–desorption isotherms of both MCM-41 and CuI/MCM-41-SH materials were type IV with H4-type hysteresis loops, and the pore size and specific surface area of the materials were reduced. This work demonstrates that that when the reaction time was 2 h, the reaction temperature was 80 ℃ and the catalyst dosage was 100 mg, the conversion of tetralin was obtained as 92.63% and the selectivity of α-tetralone was 84.84%. The catalyst showed good reusability in the three recovery experiments. These results show that the catalyst has potential applications for green and sustainable development.

研究领域: 材料科学 · 催化 · 纳米技术 · 环境化学 · 绿色化学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2012 · IF 1.693

Densities, Viscosities, and Refractive Indices of Binary Mixtures of 1,2,3,4-Tetrahydronaphthalene with Some n-Alkanes at T = (293.15 to 313.15) K

Xianjie Gong,Yongsheng Guo,Juan Xiao,Yuzhong Yang,Wenjun Fang

Densities, viscosities, and refractive indices are investigated for binary mixtures of 1,2,3,4-tetrahydronaphthalene with several n-alkanes, namely, octane, nonane, and decane, at different temperatures (293.15 K, 298.15 K, 303.15 K, and 313.15 K) and atmospheric pressure. The values of density (ρ) of the compounds were used to compute excess molar volume (VmE) of the solution. The refractive indices of these binary systems were also determined over the whole concentration range at 293.15 K and 303.15 K.

CAS / MDL: 119-64-2
研究领域: 物理化学 · 热力学
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Journal of Environmental Chemical Engineering · 2018 · IF 0

Poly aromatic hydrocarbon (naphthalene) conversion into value added chemical (tetralin): Activity and stability of MoP/AC catalyst

Muhammad Usman,Dan Li,Rauf Razzaq,Ullah Latif,Oki Muraza,Zain Hassan Yamani,Bassem A. Al-Maythalony,Chunshan Li,Suojiang Zhang

The numerous environmental challenges attributed to polyaromatic hydrocarbons (PAH) recently accounted to search for better valorization options especially, naphthalene upgrading into tetralin is a promising catalytic process which is important for the petrochemical industry due to the widespread applicability and global demand. A key challenge in this process is to design highly efficient, low temperature active, selective, stable, yet cost-effective catalyst. Herein, we employed impregnation and temperature-programmed reduction (TPR) method and developed an activated carbon (AC) supported molybdenum phosphide (MoP) catalyst. The samples were successfully characterized using XRD , XPX, SEM , TEM , EPMA , TGA/DTA, N 2 adsorption, NH 3 -TPD and pyridine FTIR. The catalysts were evaluated for naphthalene conversion under various operational conditions; 240–360 °C, 4.0 MPa, and 3.0–20/h LHSV. Excellent naphthalene conversion of 82% and 99% selectivity to tetralin was achieved with the 10 wt.% MoP/AC catalyst. This promising low temperature performance could be attributed to the moderate acidity of the catalyst inhibiting hydrocracking; and the large surface area of AC that increased MoP dispersion and associated AC-MoP interactions.

研究领域: 石油化工 · 催化化学 · 环境科学
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FUEL · 2023 · IF 7.4

Study on structure and properties of remained solids from liquefaction of Naomaohu coal in tetrahydronaphthalene

Xizhuang Qin,Qingya Liu,Jiachen Yu,Lei Shi,Zhenyu Liu

To understand the main reactions in direct coal liquefaction and to find out the temperature at which condensation reactions become significant, the liquefaction of a vitrinite-rich coal, Naomaohu (NMH), is studied at 380–460 °C in tetrahydronaphthalene (THN). The main focuses are on the trends of products yield and evolution of solid residues’ composition and structure. It is found that NMH is very active at 420 °C with a conversion of >90 wt% and an oil-plus-water yield of 39 wt% in 40 min. The reaction, especially the condensation behaviors at temperatures lower than 420 °C are different from those at higher temperatures as indicated by the trends in products yield and in the residue’s morphology and properties. The residues obtained at 440–460 °C contain mesophase pitch spherules. The changes in residues’ volatiles content, H/C and O/C ratios, FTIR and Raman spectra, and ESR parameters are slow at 380–420 °C but much fast at 440–460 °C. These different trends are clearly evidenced by plotting the residues’ characterization parameters against the decreasing residue yield during the reaction.

研究领域: 化学工程 · 能源科学
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Journal of Energy Storage · 2020 · IF 3.762

Development of composite phase change cold storage material and its application in vaccine cold storage equipment

Yi Zhao,Xuelai Zhang,Xiaofeng Xu,Shihua Zhang

According to the temperature requirements of pharmaceutical cold chain logistics, the aim is to develop phase change materials with a phase transition temperature of 2 °C ~ 8 °C. In this study, a mixed solution of tetradecane (TD) and lauryl alcohol (LA) was selected as the base liquid. In view of the low thermal conductivity of organic phase change materials, expanded graphite (EG) was added to TD-LA to improve the thermal conductivity. This study also developed a new type of cold storage equipment for vaccine, which can monitor the temperature of the vaccine in real time on the user's mobile phone. The cold storage equipment is equipped with a special cold storage box of vaccine. The vaccine reagent tube can be placed in the storage hole of the cold storage box. It can ensure that the cold storage agent in the cold storage box releases and transmits the cold quantity more evenly among the goods. Coupling the developed low temperature phase change material with the cold storage equipment can ensure that the vaccine is always in the required low temperature environment in the process of transportation for a long time to ensure its quality.

CAS / MDL: 112-53-8 629-59-4
研究领域: 材料科学 · 生物医药工程
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2023 ·Vol. 34 ·期 7 ·987-991 · IF 1.4

Effect of Different Al2O3 Supports on the Synthesis of Tetralin by Selective Catalytic Hydrogenation of Naphthalene

Su Xiao-Ping,Zhao Le,Wang Xiang-Tong,Wang Zhao,Wang Zhi-Chao,Shen Tao,Zhang Ping

Different Al2O3 carriers were synthesized by co-precipitation and sol-gel method. From them, 4%NiO-20%MoO3/Al2O3 catalysts were prepared by incipient wetness impregnation. The catalysts were characterized by X-ray diffraction analysis (XRD), N2 adsorption-desorption, NH3 temperature programmed desorption (TPD) and H2-temperature programmed reduction (TPR) and subsequently used for selective hydrogenation of naphthalene to high-value tetralin. The results showed that Ni-Mo/so-ge Al2O3 (900) exhibited better catalytic performance than Ni Mo/commercial Al2O3, achieving 99.56% naphthalene conversion and 99.43% tetralin selectivity.

研究领域: 催化化学 · 材料科学
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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2022 · IF 3.898

Tribological and rheological performance of lithium grease with poly-α-olefin and alkyl-tetralin as base oils

Chen Chen,Yujie Liu,Qiong Tang,Hong Xu,Mingxing Tang,Xuekuan Li,Lei Liu,Jinxiang Dong

A new category of lithium greases was synthesized by using poly- α -olefin (PAO8) and alkyl-tetralin as base oil, where the alkyl-tetralins were synthesized by the alkylation of tetralin and olefins. The influence of thickener concentration, alkyl-tetralin content and type of blend oils on the rheological and tribological performance of lithium grease was investigated. The microstructures of soap fibers were measured to reveal the structure–property correlations. The concentration of thickener and alkyl-tetralin content obviously affect the lubricating performance of lithium grease, while the molecular structure of alkyl-tetralin has no obvious impact on their properties. It was found that alkyl-tetralin could significantly enhance the thickening ability of PAO8 base oils, and decrease the amount of thickeners by 1.5% (mass). Lithium greases prepared using 20% (mass) alkyl-tetralin as co-base oil exhibited high colloidal stability, excellent rheological behaviors and tribological properties.

CAS / MDL: 1310-66-3
研究领域: 材料科学 · 化学工程 · 机械工程
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FUEL PROCESSING TECHNOLOGY · 2022 · IF 8.129

Unpredictable properties of industrial HY zeolite for tetralin hydrocracking

Jiayao Qi,Yanni Guo,Hanqiong Jia,Binbin Fan,Hang Gao,Bo Qin,Jinghong Ma,Yanze Du,Ruifeng Li

The commercial Y zeolites are widely used in catalytic cracking and hydrocracking in industry, the efficient hydrocracking of polycyclic aromatics is a challenging task in petroleum and coal refining. The acidic zeolite in the hydrocracking bi-functional catalyst dominates largely the product selectivity, so understanding the independent effect of acid sites is favorable to the design of the catalyst. Herein, five industrial HY zeolites with different ratios of Si/Al were applied to tetralin hydrocracking to produce high-value benzene, toluene, and xylenes (BTX) in a high-pressure fixed bed reactor . The result indicated that mesoporous HUSY not only improved the catalytic activity but also exhibited longer-term stability compared with micropore HY. Interestingly, tetralin conversion in the hydrocracking showed a high-similar value when the Si/Al ratio of the zeolites is above 26 with almost identical porous structure , regardless of the distribution of acidity. And the yield of products is associated with the acidity of the HY zeolites, the lower the Si/Al ratio is, the more favorable the monocyclic aromatic hydrocarbons form. Therefore, it is beneficial for the industrial process to reduce the zeolite post-treatment procedure which achieves the high activity and BTX yield in the hydrocracking of tetralin and to abate the cost consumption, although it is still impractical to get rid of the trial-error scheme for the designing of an efficient catalyst in practice.

CAS / MDL: 119-64-2
研究领域: 催化化学 · 石油加工工程
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INTERNATIONAL JOURNAL OF CHEMICAL KINETICS · 2020 ·Vol. 53 ·期 1 ·154-163 · IF 1.531

Unraveling chemical structure of laminar premixed tetralin flames at low pressure with photoionization mass spectrometry and kinetic modeling

Yuyang Li,Jiabiao Zou,Wenhao Yuan,Chuangchuang Cao,Yan Zhang,Fei Qi,Jiuzhong Yang

This work reports an investigation on laminar premixed flames of tetralin at 30 Torr and equivalence ratios of 0.7 and 1.7. Measurements of the chemical structure including identification and mole fraction measurements of free radicals, isomers, and polycyclic aromatic hydrocarbons (PAHs) were performed using synchrotron vacuum ultraviolet photoionization mass spectrometry (SVUV-PIMS). A kinetic model with 296 species and 1 577 reactions was developed and validated against the flame chemical structure data measured in this work. Modeling analysis reveals the key reaction pathways in tetralin decomposition and PAHs formation. The H-atom abstraction reactions by H, O, and OH are found to control the consumption of tetralin in the lean flame, while those by H play the dominant role in the rich flame. Indene and naphthalene have very high concentration levels in the rich tetralin flame due to the existence of direct formation pathways from the decomposition of tetralin. The two bicyclic PAHs and their radicals play significant roles in the PAHs growth process of tetralin combustion, which results in the high sooting tendency of tetralin compared to those of alkylbenzenes with smaller or same carbon atom numbers.

研究领域: 化学动力学 · 燃烧科学
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Nature Communications · 2024 ·Vol. 15 ·期 1 ·1-12 · IF 14.7

Selective production of methylindan and tetralin with xylose or hemicellulose

Zou Zhufan,Yu Zhenjie,Guan Weixiang,Liu Yanfang,Yao Yumin,Han Yang,Li Guangyi,Wang Aiqin,Cong Yu,Liang Xinmiao,Zhang Tao,Li Ning

Indan and tetralin are widely used as fuel additives and the intermediates in the manufacture of thermal-stable jet fuel, many chemicals, medicines, and shockproof agents for rubber industry. Herein, we disclose a two-step route to selectively produce 5-methyl-2,3-dihydro-1 H -indene (abbreviated as methylindan) and tetralin with xylose or the hemicelluloses from agricultural or forestry waste. Firstly, cyclopentanone (CPO) was selectively formed with ~60% carbon yield by the direct hydrogenolysis of xylose or hemicelluloses on a non-noble bimetallic Cu-La/SBA-15 catalyst. Subsequently, methylindan and tetralin were selectively produced with CPO via a cascade self-aldol condensation/rearrangement/aromatization reaction catalyzed by a commercial H-ZSM-5 zeolite. When we used cyclohexanone (another lignocellulosic cycloketone) in the second step, the main product switched to dimethyltetralin. This work gives insights into the selective production of bicyclic aromatics with lignocellulose.

研究领域: 化学工程 · 可再生资源利用
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