142-68-7Relevant articles and documents
Adsorptive interaction between 1,5-pentanediol and MgO-modified ZrO2 catalyst in the vapor-phase dehydration to produce 4-penten-1-ol
Duan, Hailing,Unno, Masaki,Yamada, Yasuhiro,Sato, Satoshi
, p. 96 - 102 (2017)
Vapor-phase catalytic dehydration of 1,5-pentanediol (1,5-PDO) was investigated over monoclinic ZrO2 catalysts modified with basic oxides. An unsaturated alcohol, 4-penten-1-ol (4P1OL), was produced together with the formation of tetrahydropyran, δ-valerolactone, 1,4-pentadiene, pentanal, 1-pentanol, and 5-hydroxypentanal, etc. Among the modified ZrO2 catalysts, only ZrO2 modified with MgO enhanced the selectivity to 4P1OL efficiently. The most active modified catalyst was found to have 20 mol% MgO and a calcination at 800 °C (MgO/ZrO2), and the selectivity of 4P1OL exceeded 83% at 400 °C. A pulse adsorption measurement of several chemicals clarified adsorptive interaction between a reactant and a catalyst at 220 °C: the interaction between 1,5-PDO and MgO/ZrO2 was stronger than the other adsorbates and catalysts. Another strong adsorptive interaction between 1,4-butanediol and CaO/ZrO2, which was effective in the dehydration of 1,4-butanediol to produce 3-buten-1-ol, was also observed.
Hydrogenation of 2,3-dihydropyran to tetrahydropyran
Kuplenieks,Kreile,Slavinskaya,Avots
, p. 351 - 354 (1982)
The optimum conditions for the hydrogenation of 2,3-dihydropyran to tetrahydropyran on an industrial nickel-chromium catalyst under flow and periodic conditions were found. A regression model for the process was found. The results of hydrogenation of 2,3-dihydropyran by means of a flow reactor and an autoclave of the Vishnevskii type are compared.
Ring-Closing Metathesis of Aliphatic Ethers and Esterification of Terpene Alcohols Catalyzed by Functionalized Biochar
Kerton, Francesca M.,MacQuarrie, Stephanie L.,Vidal, Juliana L.,Wyper, Olivia M.
supporting information, p. 6052 - 6056 (2021/12/10)
Functionalized biochars, renewable carbon materials prepared from waste biomass, can catalyze transformations of a range of oxygen-containing substrates via hydrogen-bonding interactions. Good conversions (up to 75.2 %) to different O-heterocycles are obtained from ring-closing C?O/C?O metathesis reactions of different aliphatic ethers under optimized conditions using this heterogeneous, metal-free, and easy separable catalyst. The diversity in the sorts of O-containing feedstocks is further demonstrated by the utilization of functionalized biochar to promote the esterification of terpene alcohols, an important reaction in food and flavor industries. Under the optimized conditions, full conversions to various terpene esters are obtained. Moreover, both of the reactions studied herein are performed under neat conditions, thus increasing the overall sustainability of the process described.
Hydrogen-Bonding Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers over Ionic Liquid under Metal-Free Conditions
Wang, Huan,Zhao, Yanfei,Zhang, Fengtao,Wu, Yunyan,Li, Ruipeng,Xiang, Junfeng,Wang, Zhenpeng,Han, Buxing,Liu, Zhimin
, p. 11850 - 11855 (2020/05/16)
O-heterocycles have wide applications, and their efficient and green synthesis is very interesting. Herein, we report hydrogen-bonding catalyzed ring-closing metathesis of aliphatic ethers to O-heterocycles over ionic liquid (IL) catalyst under metal- and solvent-free conditions. The IL 1-butylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3H-BMIm][OTf]) is discovered to show outstanding performance, better than the reported catalysts. An interface effect plays an important role in mediating the reaction rate due to the immiscibility between the products and the IL catalyst, and the products can be spontaneously separated. NMR analysis and DFT calculation suggest that a pair of cation and anion of [SO3H-BMIm][OTf] could form three strong H-bonds with an ether molecule, which catalyze the ether transformation via a cyclic oxonium intermediate. A series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines and dioxane can be obtained from their corresponding ethers in excellent yields (e.g., >99 %). This work opens an efficient and metal-free way to produce O-heterocycles from aliphatic ethers.
Efficient one-pot conversion of furfural into 2-methyltetrahydrofuran using non-precious metal catalysts
Jia, Xinxin,Li, Cuiqing,Liu, Ping,Song, Yongji,Sun, Luyang,Wang, Hong,Zhang, Chen,Zhang, Wei
, (2020/04/29)
2-methyltetrahydrofuran, a biomass-derived chemical, is an important solvent with broad applications in organic chemistry. In this study, one-pot conversion of furfural into 2-methyltetrahydrofuran over non-precious metal catalysts was achieved by two-stage packing in a single reactor. The first stage converted furfural into 2-methylfuran over Co-based catalysts, and the second stage converted 2-methylfuran into 2-methyltetrahydrofuran over Ni-based catalysts. In order to reveal the reaction pathway and mechanism of this process, the hydrogenation reactions of 2-methylfuran, furfuryl alcohol, and tetrahydrofurfuryl alcohol were also carefully investigated. It is discovered that the conversion of furfural into 2-methylfuran could be catalyzed by Lewis acid sites, which was confirmed by a correlation between 2-methylfuran production rate and Lewis acid site density. Also, a mechanism on the direct conversion of furfural into 2-methylfuran without forming furfuryl alcohol as the intermediate is proposed. The experimental results of 2-methylfuran, furfuryl alcohol, and tetrahydrofurfuryl alcohol hydrogenation/hydrodeoxygenation over various catalysts provided valuable information on the future design of 2-methyltetrahydrofuran catalyst.