592-90-5Relevant academic research and scientific papers
Silver(I)-Catalyzed Reductive Cross-Coupling of Aldehydes to Structurally Diverse Cyclic and Acyclic Ethers
Dong, Guichao,Li, Chuang,Liang, Ting,Xu, Xin,Xu, Zhou
supporting information, p. 1817 - 1821 (2022/03/16)
A range of medium-sized cyclic ethers (5 to 11 membered) have been effectively synthesized through intramolecular reductive coupling of dialdehydes initiated by 50 ppm to 0.5% of AgNTf2 with hydrosilane at 25 °C. The catalytic system is also suitable for the coupling of two different monoaldehydes to provide unsymmetrical ethers. This protocol features broad functional group compatibility, high product diversity, high efficiency, and utility in the late-stage modification of complex biorelevant molecules.
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.
Synthetic method of epoxide
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Paragraph 0020; 0034; 0035; 0036, (2018/10/11)
The invention discloses a synthetic method of epoxide. Hydrogen peroxide is used as an oxidant, and a catalytic system consisting of a catalyst and solvent is used for catalyzing a reactant comprisinga carbon-carbon double bonds and at least one other functional group to synthesize the epoxide; in the catalytic system, the solvent is a mixture of alcohol and water, and the catalyst is a metal ionmodified mixture consisting of an MWW structure titanium silicon molecular sieve and a carrier; and the weight percent of the titanium silicon molecular sieve in the catalyst is not less than 20 percent of the total weight of the catalyst, the type of metal ions is expressed as MXO by virtue of a molecular expression of metal oxide, wherein X is equal to 1 or 2, the weight percent is 0.05 to 3 percent of the total weight of the catalyst by calculating with the content of metal atoms M, and the carrier is at least one of silicon dioxide, aluminum oxide and aluminum phosphate with the balance weight. By utilizing the catalyst system, the epoxide can be high actively and high selectively synthesized in a catalytic manner; and the reaction process is simple and environment-friendly, the energy consumption is low, and the industrialized production and application are easy.
Remarkably high catalyst efficiency of a disilaruthenacyclic complex for hydrosilane reduction of carbonyl compounds
Tahara, Atsushi,Sunada, Yusuke,Takeshita, Takashi,Inoue, Ryoko,Nagashima, Hideo
supporting information, p. 11192 - 11195 (2018/10/24)
A disilaruthenacyclic complex (1) showed extremely high catalytic activity for hydrosilane reduction of aldehydes and ketones to silyl ethers and secondary and tertiary amides to the corresponding amines. An σ-CAM mechanism was proposed to explain the activity.
Synthesis of cyclic ethers from diols in the presence of copper catalysts
Bayguzina,Gimaletdinova,Khusnutdinov
, p. 1840 - 1843 (2018/02/06)
A number of cyclic ethers, namely tetrahydrofuran, 2,5-dimethyltetrahydrofuran, tetrahydropyran, 1,4-dioxane, oxepane, oxocane, and 1,4-oxathiane, have been synthesized in high yields by intramolecular dehydration of diols in the presence of copper-based catalysts.
Tetrabutylphosphonium Bromide Catalyzed Dehydration of Diols to Dienes and Its Application in the Biobased Production of Butadiene
Stalpaert, Maxime,Cirujano, Francisco G.,De Vos, Dirk E.
, p. 5802 - 5809 (2017/09/15)
We report the use of the ionic liquid tetrabutylphosphonium bromide as a solvent and catalyst for dehydration of diols to conjugated dienes. This system combines stability, high reaction rates, and easy product separation. A reaction mechanism for the model compound 1,2-hexanediol is proposed and experimentally corroborated. This particular mechanism allows for the selective formation of conjugated dienes, in contrast with purely acidic catalysis. Next, the reaction is also performed on various other diols. As a first application, we assessed the biobased production of 1,3-butadiene. With 1,4-butanediol as the starting material, a 94% yield of butadiene was reached at 100% conversion.
Synthesis of common-sized heterocyclic compounds by intramolecular cyclization over halide cluster catalysts
Nagashima, Sayoko,Sasaki, Tomoaki,Kamiguchi, Satoshi,Chihara, Teiji
supporting information, p. 764 - 766 (2015/06/22)
Five- to seven-membered common-sized heterocyclic compounds containing an oxygen, sulfur, or nitrogen were synthesized by the intramolecular condensation of α,ω-hydroxy, mercapto, or amino alkanes, respectively, over halide cluster complexes as a thermally stable molecular solid weak acid catalyst in the gas phase at temperatures ≥150 °C. From ω- mercapto and ω-amino alcohols, cyclic sulfides and amines were obtained, respectively. These unimolecular reactions are thermodynamically and kinetically favored.
Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols
Kim, Junghwa,Lee, Dong-Hwan,Kalutharage, Nishantha,Yi, Chae S.
, p. 3881 - 3885 (2015/01/16)
The cationic ruthenium-hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral nonracemic ethers.
Poly(oxyalkylene) synthesis in Bronsted acid ionic liquids
Zhang, Shaodong,Feret, Aurelie,Lefebvre, Herve,Tessier, Martine,Fradet, Alain
scheme or table, p. 11092 - 11094 (2011/11/06)
The polyetherification of diols with 4-12 methylene units was studied in Bronsted Acid Ionic Liquids (BAILs). High molar mass poly(oxyalkylene)s were obtained at relatively low temperatures (130 °C), except in the cases of 1,4-butanediol and 1,6-hexanediol where cyclic ether formation was observed.
Vapor-phase catalytic dehydration of terminal diols
Abe, Katsutoshi,Ohishi, Yusuke,Okada, Takuto,Yamada, Yasuhiro,Sato, Satoshi
experimental part, p. 419 - 424 (2012/02/03)
Vapor-phase catalytic reactions of several terminal diols were investigated over several rare earth oxides, such as Sc2O3, Y 2O3, CeO2, Yb2O3, and Lu2O3. Sc2O3 showed selective catalytic activity in the dehydration of terminal diols with long carbon chain, such as 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, and 1,12-dodecanediol, to produce the corresponding unsaturated alcohols. In the dehydration of 1,6-hexanediol, 5-hexen-1-ol was produced with selectivity over 60 mol%, together with by-products such as ε-caprolactone and oxacycloheptane. In the dehydration of 1,10-decanediol, 9-decen-1-ol was produced with selectivity higher than 70 mol%. In addition to Sc 2O3, heavy rare earth oxides such as Lu2O 3 as well as monoclinic ZrO2 showed moderate selectivity in the dehydration of the terminal diols.
