16306-39-1Relevant articles and documents
Partial Hydrogenation of Polycyclic Aromatic Hydrocarbons by Electroreduction in Protic Solvents
Anowski,Voss
, p. 337 - 344 (1996)
Polycyclic aromatic hydrocarbons (PAH) such as anthracene (1), phenanthrene (5), acenaphthylene (15), pyrene (17), chrysene (22), and fluoranthene (28) are selectively hydrogenated upon electroreduction at a lead cathode in ethanolic solution. The degree of hydrogenation and the structure of the products depend on the reaction conditions, in particular on the applied reduction potential.
HYDROLIQUEFACTION OF COAL AND HYDROGENATION OF PHENANTHRENE WITH IRON CATALYSTS ACTIVATED BY NEW METHOD
Ogata, Eisuke,Hatakeyama, Kazuya,Kamiya, Yoshio
, p. 1913 - 1916 (1985)
Iron catalysts obtained by the CO pretreatment of iron oxide and iron ore suspended in hydrocarbon solvents presented high catalytic activities for the hydroliquefaction of coal and hydrogenation of phenanthrene.
Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof
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Paragraph 0094-0095; 0106-0113, (2021/05/29)
The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.
Metallic Barium: A Versatile and Efficient Hydrogenation Catalyst
Stegner, Philipp,F?rber, Christian,Zenneck, Ulrich,Knüpfer, Christian,Eyselein, Jonathan,Wiesinger, Michael,Harder, Sjoerd
supporting information, p. 4252 - 4258 (2020/12/22)
Ba metal was activated by evaporation and cocondensation with heptane. This black powder is a highly active hydrogenation catalyst for the reduction of a variety of unactivated (non-conjugated) mono-, di- and tri-substituted alkenes, tetraphenylethylene, benzene, a number of polycyclic aromatic hydrocarbons, aldimines, ketimines and various pyridines. The performance of metallic Ba in hydrogenation catalysis tops that of the hitherto most active molecular group 2 metal catalysts. Depending on the substrate, two different catalytic cycles are proposed. A: a classical metal hydride cycle and B: the Ba metal cycle. The latter is proposed for substrates that are easily reduced by Ba0, that is, conjugated alkenes, alkynes, annulated rings, imines and pyridines. In addition, a mechanism in which Ba0 and BaH2 are both essential is discussed. DFT calculations on benzene hydrogenation with a simple model system (Ba/BaH2) confirm that the presence of metallic Ba has an accelerating effect.
Highly Active Superbulky Alkaline Earth Metal Amide Catalysts for Hydrogenation of Challenging Alkenes and Aromatic Rings
Eyselein, Jonathan,F?rber, Christian,Grams, Samuel,Harder, Sjoerd,Knüpfer, Christian,Langer, Jens,Martin, Johannes,Thum, Katharina,Wiesinger, Michael
supporting information, p. 9102 - 9112 (2020/03/30)
Two series of bulky alkaline earth (Ae) metal amide complexes have been prepared: Ae[N(TRIP)2]2 (1-Ae) and Ae[N(TRIP)(DIPP)]2 (2-Ae) (Ae=Mg, Ca, Sr, Ba; TRIP=SiiPr3, DIPP=2,6-diisopropylphenyl). While monomeric 1-Ca was already known, the new complexes have been structurally characterized. Monomers 1-Ae are highly linear while the monomers 2-Ae are slightly bent. The bulkier amide complexes 1-Ae are by far the most active catalysts in alkene hydrogenation with activities increasing from Mg to Ba. Catalyst 1-Ba can reduce internal alkenes like cyclohexene or 3-hexene and highly challenging substrates like 1-Me-cyclohexene or tetraphenylethylene. It is also active in arene hydrogenation reducing anthracene and naphthalene (even when substituted with an alkyl) as well as biphenyl. Benzene could be reduced to cyclohexane but full conversion was not reached. The first step in catalytic hydrogenation is formation of an (amide)AeH species, which can form larger aggregates. Increasing the bulk of the amide ligand decreases aggregate size but it is unclear what the true catalyst(s) is (are). DFT calculations suggest that amide bulk also has a noticeable influence on the thermodynamics for formation of the (amide)AeH species. Complex 1-Ba is currently the most powerful Ae metal hydrogenation catalyst. Due to tremendously increased activities in comparison to those of previously reported catalysts, the substrate scope in hydrogenation catalysis could be extended to challenging multi-substituted unactivated alkenes and even to arenes among which benzene.
Understanding Ni Promotion of MoS2/γ-Al2O3 and its Implications for the Hydrogenation of Phenanthrene
Schachtl, Eva,Zhong, Lei,Kondratieva, Elena,Hein, Jennifer,Gutiérrez, Oliver Y.,Jentys, Andreas,Lercher, Johannes A.
, p. 4118 - 4130 (2015/12/26)
The chemical composition and structure of NiMo sulfides supported on γ-Al2O3 and its properties for hydrogenation of polyaromatic compounds is explored. The presence of Ni favors the formation of disperse octahedrally coordinated Mo in the oxide precursors and facilitates its reduction during sulfidation. This decreases the particle size of MoS2 (measured by transmission electron microscopy) and increases the concentration of active sites up to a Ni/(Mo+Ni) atomic ratio of 0.33. At higher Ni loadings, the size of the MoS2 did not decrease further, although the concentration of adsorption sites and accessible Ni atoms decreased. This is attributed to the formation of NiSx clusters at the edges of MoS2. Nickel also interacts with the support, forming separated NiSx clusters, and is partially incorporated into the γ-Al2O3, forming a Ni-spinel. The hydrogenation of phenanthrene follows two pathways; by adding one or two H2 molecules, 9,10-dihydrophenanthrene or 1,2,3,4-tetrahydrophenanthrene are formed as primary products. Only symmetric hydrogenation, leading to 9,10-dihydrophenanthrene, was observed on unpromoted MoS2/γ-Al2O3. In contrast, symmetric and deep hydrogenation (leading to 9,10-dihydrophenanthrene and 1,2,3,4-tetrahydrophenanthrene, respectively) occur with similar selectivity on Ni-promoted MoS2/γ-Al2O3. The rates of both pathways increase linearly with the concentration of Ni atoms in the catalyst. The higher rates for symmetric hydrogenation are attributed to increasing concentrations of reactive species at the surface, and deep hydrogenation is concluded to be catalyzed by Ni at the edge of MoS2 slabs. Well, everybody knows that Ni is the word: In promoted MoS2/γ-Al2O3, Ni substitutes Mo at the perimeter of the MoS2 slabs, forming particles of Ni sulfides with varying sizes at the edges of MoS2 or on the support. The proportions of these species depend on the Ni content. Ni-substituted sites perform faster and deeper hydrogenation of phenanthrene than non-promoted sites.
Quenched skeletal Ni as the effective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons
Liu, Chengyun,Rong, Zeming,Sun, Zhuohua,Wang, Yong,Du, Wenqiang,Wang, Yue,Lu, Lianhai
, p. 23984 - 23988 (2013/11/19)
Quenched skeletal Ni is an active and selective catalyst for selective partial hydrogenation of polycyclic aromatic hydrocarbons (PAHs). The molecular structure of PAHs significantly dominate the hydrogenation process and furthermore, the distribution of hydrogenated products.
Reductive hydrogenation of polycyclic aromatic hydrocarbons catalyzed by metalloporphyrins
Nelkenbaum, Elza,Dror, Ishai,Berkowitz, Brian
, p. 210 - 217 (2008/02/04)
The hydrogenation of polycyclic aromatic hydrocarbons (PAHs) (naphthalene, anthracene, and phenanthrene) catalyzed by metalloporphyrins based on cobalt, nickel or iron was studied in aqueous solutions at room temperature and ambient pressure. Nickel porphyrin (P1) activated by nanosized zero-valent iron (nano-ZVI) and cobalt porphyrins (P2) and (P4) activated by titanium(III) citrate as the electron donor were demonstrated to be promising catalysts for the reductive hydrogenation of PAHs. In particular, partially saturated di-, tetra-, and octahydrogenated products were obtained for anthracene or phenanthrene using a nickel porphyrin activated by nano-ZVI, while naphthalene was transformed to tetralin. Systems containing cobalt porphyrins activated by titanium(III) citrate exhibited a high selectivity and activity toward hydrogenation of anthracene, producing 9,10-dihydroanthracene. However, no formation of hydrogenated hydrocarbons was observed from naphthalene or phenanthrene using cobalt porphyrins.
Recoverable, Reusable, Highly Active, and Sulfur-Tolerant Polymer Incarcerated Palladium for Hydrogenation
Okamoto, Kuniaki,Akiyama, Ryo,Kobayashi, Shu
, p. 2871 - 2873 (2007/10/03)
A new type of immobilized palladium, PI (polymer incarcerated) Pd (2b), from Pd(PPh3)4 and copolymer (1b) has been developed. The excellent activity of PI Pd has been demonstrated in hydrogenation of various olefins, benzyl ethers, and nitro and aromatic compounds. PI Pd is tolerant under high pressure and high temperature and can be recovered and reused several times without loss of activity even under harsh conditions. Moreover, PI Pd is highly resistant to poisoning by sulfur.
Mechanochemistry of some hydrocarbons
Field, Leslie D.,Sternhell, Sever,Wilton, Howard V.
, p. 4051 - 4062 (2007/10/03)
Aromatic hydrocarbons (biphenyl, naphthalene, anthracene and phenanthrene) were subjected to ball milling (SPEX 8000) with approximately ten-fold weight of inorganic materials (alumina or silica). After about 24 h ail of the hydrocarbons were converted largely to carbon (graphite), but at intermediate stages disproportionation products (tetralin, phenylcyclohexane, bicyclohexyl, 9,10-dihydroanthracene, 1,2,3,4-tetrahydroanthracene, 1,2,3,4,4a,9,9a,10-octahydroanthracene, 1,2,3,4,5,6,7,8-actahydroanthracene, 9,10-dihydrophenanthrene, 1,2,3,4-tetrahydrophenanthrene, 1,2,3,4,4a,9,9a,10-octahydrophenanthrene, 1,2,3,4,5,6,7,8-octahydrophenanthrene) were also obtained in significant yields.
