119-64-2Relevant articles and documents
Magnetically separable mesoporous silica-supported palladium nanoparticle-catalyzed selective hydrogenation of naphthalene to tetralin
Yang, Yonghui,Xu, Bolian,He, Jie,Shi, Jianjun,Yu, Lei,Fan, Yining
, (2019)
A novel magnetically separable mesoporous silica-supported palladium catalyst was designed and prepared for the selective hydrogenation of naphthalene to tetralin, which is an important transformation from a practical viewpoint. In the catalyst, Pd nano grains were dispersed uniformly and protected within the mesoporous silica shells being coated on the Fe3O4 core, so that the durability of the catalyst could be significantly improved.
Treatment of naphthols with B(C6F5)3: Formation and characterization of the Lewis acid adducts of their keto isomers
Vagedes, Dominik,Froehlich, Roland,Erker, Gerhard
, p. 3362 - 3365 (1999)
With the strong Lewis acid B(C6F5)3, the keto tautomers from a variety of naphthol derivatives are obtained (e.g. α- naphthol, see scheme). The adducts of the tautomers were characterized by X-ray structure analysis, and the first attempts at hydrozirconation of the adducts were made.
Hydrogenation of Aromatics in Diesel Fuels on Pt/MCM-41 Catalysts
Corma,Martinez,Martinez-Soria
, p. 480 - 489 (1997)
The hydrogenation activity of Pt supported on two mesoporous MCM-41 samples differing in their chemical composition has been studied by following the kinetics of the hydrogenation of naphthalene at 225-275°C reaction temperature and 5.0 MPa total pressure and by comparing the kinetic parameters obtained with Pt supported on a mesoporous amorphous silica-alumina (MSA) and other conventional supports, such as commercial amorphous silica-alumina (ASA), zeolite USY, γ-alumina, and silica. The two mesoporous MCM-41 and MSA materials having very high surface areas allowed for a better dispersion of the Pt particles, and they showed a superior overall hydrogenation activity as compared to the other supports. However, Pt/USY displayed the highest turnover (activity per exposed surface Pt), owing to the interaction of small Pt aggregates in the supercage of the zeolite with the strong Broensted acid sites associated to framework aluminum forming electron-deficient Pt species of known enhanced activity. Moreover, both the Al-MCM-41 and USY-based catalysts presented the highest sulfur tolerance during the hydrogenation of a naphthalene feed containing 200 ppm sulfur added as dibenzothiophene. The high metal dispersion and the interaction of the small Pt clusters with the mildly acidic sites present in Al-MCM-41 may account for its high sulfur tolerance. The superior hydrogenation activity and sulfur tolerance of Pt-MCM-41 catalyst observed in the naphthalene experiments were further confirmed during the hydrogenation of a hydrotreated light cycle oil (LCO) feed containing ca 70 wt% aromatics and 400 ppm sulfur.
Mechanisms of Decomposition of the Ene Adducts of Some 1,3-Cyclohexadienes to Benzene or Tetralin and Dihydroenophile.
Jacobson, Barry M.,Gerhard, Daniela,Jackson, Cynthia,Smallwood, Joan
, p. 3344 - 3347 (1980)
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THE SILICON-MODIFIED METAL AMMONIA REDUCTION OF AROMATIC COMPOUNDS
Rabideau, Peter W.,Karrick, Gregory L.
, p. 2481 - 2484 (1987)
A trimethylsilyl substituent is used to control regiochemistry in the metal-ammonia reduction of several naphthalenes, and is subsequently removed resulting in a " Misoriented Birch Reduction."
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Friedman et al.
, p. 1287 (1959)
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The hydrogenation of aromatic compounds under mild conditions by using a solid Lewis acid and supported palladium catalyst
Zhang, Peng,Wu, Tianbin,Hou, Minqiang,Ma, Jun,Liu, Huizhen,Jiang, Tao,Wang, Weitao,Wu, Congyi,Han, Buxing
, p. 3323 - 3327 (2014)
Al2O3 or SiO2 particles with abundant surface hydroxyl groups can prevent side reactions of aromatic compounds with AlCl3 completely; this Lewis acid can potentially destroy the stable structure of aromatic comp
Catalyses of Fe and FeS2 on the Reaction of Di(1-naphthyl)methane
Wei, Xian-yong,Ogata, Eisuke,Niki, Etsuo
, p. 2199 - 2202 (1991)
Reactions of di(1-naphthyl)methane (DNM) over Fe and FeS2 at 300 deg C were carried out to investigate the catalytic activities and selectivities of the two catalysts.Both catalysts showed high activities for the reaction of DNM but Fe catalyzed DNM hydrogenation whereas FeS2 catalyzed DNM hydrocracking.This difference can be ascribed to the presence of sulfur.
Selective hydrogenation of 1-naphthol on USY-supported NiB nanocatalyst
Wang, Bo,Liu, Hui
, p. 3197 - 3204 (2017)
Selective hydrogenation of 1-naphthol to 5,6,7,8-tetrahydro-1-naphthol was investigated over several Ni- and Pd-based supported catalysts such as supported Ni/γ-Al2O3, Pd/C, and NiB/ultrastable Y zeolite (USY). It was found that USY-
Water as an additive to enhance the ring opening of naphthalene
Wang, Qian,Fan, Honglei,Wu, Suxiang,Zhang, Zhaofu,Zhang, Peng,Han, Buxing
, p. 1152 - 1158 (2012)
Use of water as a reaction medium or additive to enhance reaction efficiency is an important topic in green chemistry, and ring opening and contraction reactions of aromatics are crucial for upgrading diesels. In this work, we investigated the effect of water on the yields of ring opening and contraction reactions of naphthalene. A series of catalysts, such as Rh 2O3/HY zeolite, Mo-Ni oxide and their physical mixtures, were used as the catalysts. The influences of the amount of water, hydrogen pressure, reaction temperature and reaction time on the yields of the ring opening and contraction products (ROCP) were studied. It was found that Rh 2O3/HY and Mo-Ni oxide showed an excellent synergistic effect for catalyzing the reaction, and water could be used as a green and efficient additive for enhancing the yield of the ROCP. At the optimized conditions, the yield of the ROCP could be as high as 63.3%. The mechanism for the effect of water on the reactions was discussed on the basis of control experiments.
Hydrodearomatization catalysts based on molybdenum hexacarbonyl Mo(CO)6 supported on mesoporous aromatic frameworks
Maksimov,Karakhanov,Kulikov,Terenina
, p. 589 - 594 (2017)
A method for synthesizing fine hydrodearomatization catalysts based on the immobilization of molybdenum carbonyl into the pores of mesoporous aromatic frameworks is proposed. It is shown that the amount of the deposited metal and the average size of the resulting particles depend on the support and the deposition method characteristics. The catalytic activity of the synthesized materials in the hydrogenation of bicyclic hydrocarbons at a hydrogen pressure of 5.0 MPa in a temperature range of 330–500°C is studied using the example of naphthalene, methylnaphthalenes, and biphenyl as model substrates.
Iterative Preparation of Platinum Nanoparticles in an Amphiphilic Polymer Matrix: Regulation of Catalytic Activity in Hydrogenation
Hamasaka, Go,Osako, Takao,Srisa, Jakkrit,Torii, Kaoru,Uozumi, Yasuhiro
, p. 147 - 152 (2020)
We demonstrate that iteration of the seeded preparation of platinum nanoparticles dispersed in an amphiphilic polystyrene-poly(ethylene glycol) resin (ARP-Pt) regulates their catalytic activity in the hydrogenation of aromatic compounds in water. The catalytic activity of the fifth generation of ARP-Pt [G5] prepared through four iterations of the seeded preparation was far superior to that of the initial ARP-Pt [G1] in the hydrogenation of aromatic compounds in water.
Preparation of Ni - W aromatic hydrocarbon hydrogenation catalysts by breaking reverse emulsions or suspensions of a precursor in hydrocarbon feedstock
Sizova,Serdyukov,Maksimov
, p. 131 - 137 (2016)
Reverse emulsions (hydrocarbon feedstock)/(aqueous precursor solution) for synthesizing aromatic hydrocarbon hydrogenation catalysts have been prepared using the water-soluble salts (NH4)2WS4 and Ni(NO3)2·6 H2O as precursors. It has been found that the optimum stabilizer for the emulsions is the nonionic surfactant SPAN-80. The resulting emulsions exhibit low catalytic activity in the hydrogenation of aromatic hydrocarbons; it has been shown that the activity of the systems in hydrodearomatization reactions is adversely affected by the presence of water. A procedure for preparing suspensions of solid precursor particles in a hydrocarbon feedstock by the removal of water from the resulting reverse emulsions has been developed. The catalytic activity of the resulting suspensions in the hydrogenation of aromatic hydrocarbons has been studied using naphthalene, 1-methylnaphthalene, and 2-methylnaphthalene as examples. It has been shown that the catalytic activity of the suspensions is higher than that of the reverse emulsions of the same composition. It has been found that the feedstock should be subjected to additional sulfurization with elemental sulfur for further sulfiding the surface of the nickel - tungsten catalyst. The W: Ni molar ratio of 1: 1 has been found to be optimum.
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Wooster,Smith
, p. 179 (1931)
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Facile in situ Encapsulation of Highly Dispersed Ni@MCM-41 for the Trans-Decalin Production from Hydrogenation of Naphthalene at Low Temperature
Song, Xiaoyun,Guan, Qingxin,Shu, Yu,Zhang, Xiaojing,Li, Wei
, p. 1286 - 1294 (2019)
Ni@MCM-41 catalyst that has uniformly distributed, highly dispersed Ni nanoparticles (about 2.3 nm) was designed and successfully synthesized by in situ encapsulation of Ni in the channels of MCM-41. This catalyst exhibits excellent thermal stability and hydrogenation activity. Water insoluble nickel acetylacetonate (Ni(acac)2) was first dissolved aqueous solution of cetyltrimethyl ammonium bromide (CTAB) and encapsulated in micelles of CTAB. Sodium silicate was used as a silicon source to rapidly hydrolyze and then wrap on the micelle surface to synthesize the MCM-41 zeolite. The MCM-41 zeolite encapsulating Ni(acac)2 was synthesized within a short time (4 h) at 120 °C. Compared with conventional supported catalysts, thus 3 wt.% Ni@MCM-41 has ultra-small uniformly distributed Ni nanoparticles and exhibits improved activity for the hydrogenation of naphthalene to decalin at very low reaction temperatures. The TOF and the apparent activation energy of Ni@MCM-41 and the conventional catalysts (Ni/MCM-41 and Pt/MCM-41) were evaluated and compared. And the catalysis mechanism was analyzed. Furthermore, this Ni@MCM-41 catalyst offers an additional advantage of selectivity in decalin isomerization; 92 % trans-decalin selectivity was achieved at a wide temperature range.
FeS2-Catalyzed Hydrocracking of Di(1-naphthyl)methane. Effects of Hydrogen Pressure, Catalyst Feed and Reaction Temperature, and Kinetic Study
Wei, Xian-Yong,Ogata, Eisuke,Niki, Etsuo
, p. 987 - 990 (1992)
Hydrocracking of di(1-naphthyl)methane (DNM) in the temperature range of 150-300 deg C was studied.In the presence of FeS2 and pressurized hydrogen, DNM hydrocracking took place over 175 deg C.FeS2 selectively catalyzed the cleavage of C-C linkage in DNM to give 1-methylnaphthalene and naphthalene.The rate for DNM hydrocracking strongly depended on hydrogen pressure, FeS2 feed and reaction temperature.Kinetic study indicates that DNM hydrocracking in the temperature range of 200-300 deg C could be considered as a first order reaction.Under the reaction condition (DNM 7.5 mol, decalin 30 ml, FeS2 0.5 g, sulfur 0.05 g, initial hydrogen pressure 10 MPa), the activation energy and frequency factor for DNM hydrocracking were 19 kcal mol-1 and 5.3*107 h-1, respectively.
MoCx species embedded in ordered mesoporous silica framework with hierarchical structure for hydrogenation of naphthalene
Pang, Min,Chen, Xiaozhen,Xu, Qinying,Liang, Changhai
, p. 146 - 152 (2015)
An integrated route to accomplish the incorporation of MoCx species into ordered mesoporous silica framework (OMSF) was presented. The MoVI-melamine hybrids were used as the single-source precursors for molybdenum carbides and partic
Synthesis of cyclo-1,3-dien-5-ynes
Hopf, Henning,Krueger, Anke
, p. 4378 - 4385 (2001)
Cyclo-1,3-dien-5-ynes with ring sizes from 10 to 14 (6a-e) have been prepared for the first time by using a five-step synthesis starting from the alkynols 7a-e. The final ring-closure was achieved by McMurry coupling of the α,ω-dialdehydes 12a-e with the complex TiCl3(DME)1.5. Thermal isomerization of the cyclodienynes leads to the corresponding benzocycloalkenes, and it has been shown that the ring size has a considerable influence on the temperature necessary for thermocylization.
Ben-Bassat,Ginsburg
, p. 483,490 (1974)
Naphthalene hydrogenation over nickel–tungsten sulfide catalysts synthesized in situ from DMSO–hydrocarbon medium emulsions
Sizova,Antonov,Serdyukov,Maksimov
, p. 66 - 70 (2017)
A method for synthesizing unsupported nickel–tungsten sulfide hydrodearomatization catalysts by breaking SPAN-80 surfactant-stabilized nonaqueous emulsions of solutions of different precursors in dimethyl sulfoxide (DMSO) in situ in a hydrocarbon medium h
Properties of Nanosized Cobalt-Molybdenum Sulfide Catalyst Formed In Situ from Sulfonium Thiosalt
Knyazeva,Panyukova,Maximov
, p. 504 - 510 (2019)
Abstract: A cobalt-molybdenum-containing sulfonium thiosalt is prepared; when decomposed in situ, it forms the catalyst active in hydrogenation and hydrodesulfurization. The possibility of catalyst isolation and reuse in several hydrogenation cycles is shown. It is found that a lower selectivity for naphthalene hydrogenation products in catalyst recycling is associated with decrease in the dispersity of molybdenum sulfide nanoparticles and reduction in the degree of their promotion by cobalt atoms.
Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide
Darensbourg, Donald J.,Kyran, Samuel J.
, p. 5421 - 5430 (2015)
Poly(1,4-dihydronaphthalene carbonate) has been prepared via the catalytic coupling of carbon dioxide and 1,4-dihydronaphthalene oxide using chromium(III) catalysts. The copolymer formation is found to be greatly dependent on the steric environment around the metal center. Traditional (salen)CrIIIX/cocatalyst systems bearing bulky t-butyl groups hinder the approach of the large monomer, significantly diminishing polymer chain growth and providing the entropically favored cyclic byproduct in excess. In contrast, employing the sterically unencumbered azaannulene-derived catalyst, (tmtaa)CrIIIX/cocatalyst system (tmtaa = tetramethyltetraazaannulene) shows polymer selectivity close to 90% with three times the activity (TOF = 20-30 h-1). With the use of a bifunctional (salen)CrIII catalyst, even higher polymer selectivity (>90%) can be observed. The complete synthesis of a new bifunctional tetraazaannulene ligand for a more effective catalyst is also described herein.
Pentacyclo1,6.07,9.08,10>decane: A Cyclopropane Edge-Bridged Prismane and Its Rearrangement to a Fulvene
Kostermans, Gerardus B. M.,Hogenbirk, Marijke,Turkenburg, Lucas A. M.,Wolf, Willem H. de,Bickelhaupt, Friedrich
, p. 2855 - 2857 (1987)
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From lignocellulosic biomass to renewable cycloalkanes for jet fuels
Zhang, Xuesong,Lei, Hanwu,Zhu, Lei,Wu, Joan,Chen, Shulin
, p. 4736 - 4747 (2015)
A novel pathway was investigated to produce jet fuel range cycloalkanes from intact biomass. The consecutive processes for converting lignocellulosic biomass into jet fuel range cycloalkanes principally involved the use of the well-promoted ZSM-5 in the process of catalytic microwave-induced pyrolysis and RANEY nickel catalysts in the hydrogen saving process. Up to 24.68% carbon yield of the desired C8-C16 aromatics was achieved by catalytic microwave pyrolysis at 500 °C. We observed that solvents could assist in the hydrogenation reaction of naphthalene; and the optimum result for maximizing the carbon selectivity (99.9%) of decalin was obtained from the reaction conducted in the n-heptane medium. The recovery of organics could reach ～94 wt% after the extraction process. These aromatics in the n-heptane medium were eventually hydrogenated into jet fuel range cycloalkanes. Various factors were analyzed to determine the optimal result under mild conditions. An increased catalyst loading, reaction temperature, and prolonged time could enhance the hydrogenation reactions to improve the selectivity of jet fuel range cycloalkanes. Three types of hydrogenation catalysts (NP Ni, RANEY Ni 4200, home-made RANEY Ni) were chosen to evaluate the catalytic performance. The results indicated that the home-made RANEY nickel is the optimal catalyst to obtain the highest selectivity (84.59%) towards jet fuel range cycloalkanes. These cycloalkanes obtained can be directly used as additives to synthesize the desired jet fuels by blending with other hydrocarbons. Hence integration of catalytic processes and conversion of lignocellulosic biomass paved a new avenue for the development of green bio-jet fuels over inexpensive catalysts under mild conditions.
Small et al.
, p. 3151 (1975)
Selective upgrading of biomass-derived benzylic ketones by (formic acid)–Pd/HPC–NH2 system with high efficiency under ambient conditions
Chen, Yuzhuo,Chen, Zhirong,Gong, Yutong,Mao, Shanjun,Ning, Honghui,Wang, Yong,Wang, Zhenzhen
, p. 3069 - 3084 (2021/11/16)
Upgrading biomass-derived phenolic compounds provides a valuable approach for the production of higher-value-added fuels and chemicals. However, most established catalytic systems display low hydrodeoxygenation (HDO) activities even under harsh reaction conditions. Here, we found that Pd supported on –NH2-modified hierarchically porous carbon (Pd/HPC–NH2) with formic acid (FA) as hydrogen source exhibits unprecedented performance for the selective HDO of benzylic ketones from crude lignin-derived oxygenates. Designed experiments and theoretical calculations reveal that the H+/H? species generated from FA decomposition accelerates nucleophilic attack on carbonyl carbon in benzylic ketones and the formate species formed via the esterification of intermediate alcohol with FA expedites the cleavage of C–O bonds, achieving a TOF of 152.5 h?1 at 30°C for vanillin upgrading, 15 times higher than that in traditional HDO processes (～10 h?1, 100°C–300°C). This work provides an intriguing green route to produce transportation fuels or valuable chemicals from only biomass under mild conditions.
Catalyzed transfer hydrogenation by 2-propanol for highly selective PAHs reduction
Philippov,Chibiryaev,Martyanov
, p. 15 - 22 (2020/07/15)
Catalytic hydrogenation of mono-, di- and trinuclear aromatic compounds has been studied under hydrogen transfer conditions at 150 °C and 82 °C in 2-PrOH as a hydrogen donor and with Raney nickel as a catalyst. In contrast to conjugated or condensed aromatic rings, isolated ones demonstrated low reactivity in transfer hydrogenation (TH) that can be used to increase the hydrogenation selectivity of the reaction. So, naphthalene and biphenyl are partially hydrogenated into tetralin and cyclohexylbenzene, respectively, with excellent conversion (≥ 96 %) and selectivity (≥ 98 %) for 5–6 h at 82 °C. Increasing the reaction temperature to 150 °C results expectedly in the hydrogenation of second aromatic ring, which occurs slowly enough. Only 8 % of decaline and 42 % of dicyclohexyl, correspondingly, were obtained after 5 h at 150 °C. At the same time, TH of trinuclear anthracene and phenanthrene at 150 °C resulted in the formation of deeper hydrogenated octahydro-anthracenes and -phenanthrenes, respectively.
Effect of Lanthanum Doping on the reactivity of unsupported CoMoS2 catalysts
Valdes, Carolina,Gonzalez, Diego,Flores, Kenneth,Eubanks,Valle, John,Hernandez, Carlos,Lopez, Jorge,Alcoutlabi, Mataz,Parsons
, (2020/11/24)
In the present study, catalytic systems based on La-doping were developed to improve the activity and performance of CoMoS2 hydrodesulfurization catalysts. Lanthanum-doped at 5, 10, or 25% of the Co content in CoMoS2 hydrodesulfurization catalysts were synthesized through a solvothermal process. X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS) analyses confirmed the catalysts were triphasic consisting of Co9S8, MoS2, and La2S3. The La doped catalysts showed enhanced catalytic activity compared with CoMoS2 synthesized under the same conditions. The CoMoS2 prepared under solvothermal synthesis conditions showed a catalytic activity of 6.80 mol g-1 s-1, however, the La0.05Co0.95MoS2 doping showed a catalytic activity of 6.51 mol g -1 s-1 whereas the La0.1Co0.9MoS2 and La0.25Co0.75MoS2 samples showed catalytic activities of 10.7 mol g-1 s-1. The reaction products indicated the major reaction pathway was direct desulfurization. The La0.25Co0.75MoS2 catalyst after one reaction cycle showed a lower amount of carbon, than the undoped CoMoS2 catalyst.
