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.
Cp?Ir-Catalyzed Acceptorless Dehydrogenation of Carbon-Carbon Single Bonds
Ando, Hideaki,Kusumoto, Shuhei,Wu, Weiwei,Nozaki, Kyoko
, p. 2317 - 2322 (2017)
Pentamethylcyclopentadienyl (Cp?) iridium(III) chloride catalyzed acceptorless dehydrogenation of α-tetralone is reported. Cp? iridium chloride showed higher activity in comparison to other Cp? iridium complexes having bromide, iodide, or hydride or complexes without a Cp ring. The desired product, naphthol, was obtained in up to 71% yield from α-tetralone. The dehydrogenation by Cp? iridium catalyst could be applied to not only α-tetralone but also dihydrocoumarin, dihydroquinolinone, dimethylcyclohexanone, dihydrobenzofuran and 1-isochromanone, although the conversion stayed moderate. The catalytic turnover was not limited by the increased concentration of the product but by catalyst decomposition.
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.
Synthesis of Ni–W aromatic hydrocarbon hydrogenation catalysts by the ex situ and in situ decomposition of a precursor based on a dendrimer network
Sizova,Kulikov,Zolotukhina,Serdyukov,Maksimov,Karakhanov
, p. 1107 - 1113 (2016)
A Ni–W precursor supported on a dendrimer-containing crosslinked polymer (42 wt % of a third-generation polypropylenimine dendrimer) has been first synthesized. The precursor has been subjected to the ex situ and in situ decomposition in a hydrocarbon feedstock to prepare an unsupported Ni–W sulfide catalyst. The activity of the resulting catalyst in the hydrogenation of aromatic hydrocarbons has been studied using the example of naphthalene. The process has been conducted in an autoclave-type reactor in a temperature range of 350–400°C at a hydrogen pressure of 5.0 MPa. It has been shown that the in situ synthesis of a Ni–W catalyst leads to the formation of particles exhibiting higher activity in the hydrogenation of naphthalene. The in situ synthesized Ni–W particles have been characterized by TEM and XPS.
The cyclization of parent and cyclic hexa-1,3-dien-5-ynes - A combined theoretical and experimental study
Prall, Matthias,Krueger, Anke,Schreiner, Peter R.,Hopf, Henning
, p. 4386 - 4394 (2001)
The thermal cycloisomerization of both parent and benzannelated hexa-1,3-dien-5-yne, as well as of carbocyclic 1,3-dien-5-ynes (ring size 7-14), was investigated by using pure density functional theory (DFT) of Becke, Lee, Yang, and Parr (BLYP) in connection with the 6-31G* basis set and the Brueckner doubles coupled-cluster approach [BCCD(T)] with the cc-pVDZ basis set for the parent system. The initial cyclization product is the allenic cyclohexa-1,2,4-triene (isobenzene), while the respective biradical is the transition structure for the enantiomerization of the two allenes. Two consecutive [1,2]-H shifts further transform isobenzene to benzene. For the benzannelated system, the energetics are quite similar and the reaction path is the same with one exception: the intermediate biradical is not a transition state but a minimum which is energetically below isonaphthalene. The cyclization of the carbocyclic 1,3-dien-5-ynes, which follows the same reaction path as the parent system, clearly depends on the ring size. Like the cyclic enediynes, the dienynes were found to cyclize to products with reduced ring strain. This is not possible for the 7- and 8-membered dienynes, as their cyclization products are also highly strained. For 9- to 11-membered carbocycles, all intermediates, transition states, and products lie energetically below the parent system; this indicates a reduced cyclization temperature. All other rings (12- to 14-membered) have higher barriers. Exploratory kinetic experiments on the recently prepared 10- to 14-membered 1,3-dien-5-ynes rings show this tendency, and 10- and 11-membered rings indeed cyclize at lower temperatures.
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."
Reduction of polycyclic aromatic hydrocarbons promoted by cobalt or manganese nanoparticles
Nador, Fabiana,Moglie, Yanina,Vitale, Cristian,Yus, Miguel,Alonso, Francisco,Radivoy, Gabriel
, p. 4318 - 4325 (2010)
A new methodology for the partial reduction of polycyclic aromatic and heteroaromatic hydrocarbons under mild reaction conditions is presented, the process being a reasonable alternative to the catalytic hydrogenation or the Birch reaction. The reduction protocol described is based on the use of cobalt or manganese nanoparticles generated in situ in a simple and economic way, by reduction of commercially available CoCl2·6H2O or MnCl2·2H2O in the presence of lithium sand and the corresponding PAH, acting itself as an electron carrier. The use of a deuterium-oxide-containing cobalt(II) salt allows the simple preparation of deuterium labeled products. The regiochemistry and degree of reduction in the case of 1-substituted naphthalene derivatives markedly depends on the nature of the metal-NPs used.
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.
