Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions.

Title Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions.
Authors T. Dai; C. Li; L. Li; Z.Kent Zhao; B. Zhang; Y. Cong; A. Wang
Journal Angew Chem Int Ed Engl
DOI 10.1002/anie.201710074
Abstract

Tungsten carbide was employed as the catalyst in an atom-economic and renewable synthesis of para-xylene with excellent selectivity and yield from 4-methyl-3-cyclohexene-1-carbonylaldehyde (4-MCHCA). This intermediate is the product of the Diels-Alder reaction between the two readily available bio-based building blocks acrolein and isoprene. Our results suggest that 4-MCHCA undergoes a novel dehydroaromatization-hydrodeoxygenation cascade process by intramolecular hydrogen transfer that does not involve an external hydrogen source, and that the hydrodeoxygenation occurs through the direct dissociation of the C=O bond on the W2 C surface. Notably, this process is readily applicable to the synthesis of various (multi)methylated arenes from bio-based building blocks, thus potentially providing a petroleum-independent solution to valuable aromatic compounds.

Citation T. Dai; C. Li; L. Li; Z.Kent Zhao; B. Zhang; Y. Cong; A. Wang.Selective Production of Renewable para-Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions.. Angew Chem Int Ed Engl. 2018;57(7):18081812. doi:10.1002/anie.201710074

Related Elements

Tungsten

See more Tungsten products. Tungsten (atomic symbol: W, atomic number: 74) is a Block D, Group 6, Period 6 element with an atomic weight of 183.84. The number of electrons in each of tungsten's shells is [2, 8, 18, 32, 12, 2] and its electron configuration is [Xe] 4f14 5d4 6s2. Tungsten Bohr ModelThe tungsten atom has a radius of 139 pm and a Van der Waals radius of 210 pm. Tungsten was discovered by Torbern Bergman in 1781 and first isolated by Juan José Elhuyar and Fausto Elhuyar in 1783. In its elemental form, tungsten has a grayish white, lustrous appearance. Elemental TungstenTungsten has the highest melting point of all the metallic elements and a density comparable to that or uranium or gold and about 1.7 times that of lead. Tungsten alloys are often used to make filaments and targets of x-ray tubes. It is found in the minerals scheelite (CaWO4) and wolframite [(Fe,Mn)WO4]. In reference to its density, Tungsten gets its name from the Swedish words tung and sten, meaning heavy stone.

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