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96-48-0Relevant articles and documents
Production of γ-butyrolactone from biomass-derived 1,4-butanediol over novel copper-silica nanocomposite
Hwang, Dong Won,Kashinathan, Palraj,Lee, Jong Min,Lee, Jeong Ho,Lee, U-Hwang,Hwang, Jin-Soo,Hwang, Young Kyu,Chang, Jong-San
, p. 1672 - 1675 (2011)
γ-Butyrolactone was produced highly selectively from biomass-derived 1,4-butanediol by vapor-phase dehydrocyclization over novel copper-silica nanocomposite catalyst. Compared with usual Cu(12)/SiO2, the highly Cu-loaded SiO2 nanocomposite (80 wt%) exhibited high catalyst performance with 98% yield on 400 h stream without significant deactivation even in the absence of H2.
Light-Promoted Minisci Coupling Reaction of Ethers and Aza Aromatics Catalyzed by Au/TiO2 Heterogeneous Photocatalyst
Li, Zhanchong,Wu, Liangying,Guo, Jiabao,Shao, Yifei,Song, Yang,Ding, Yuzhou,Zhu, Li,Yao, Xiaoquan
, p. 3671 - 3678 (2021)
In this paper, Au/TiO2 nanocomposite was synthesized and utilized as highly efficient and green photocatalyst for organic reactions. A sheet-like anatase titanium dioxide material with a highly active (001) crystal plane was prepared via a solvothermal method. Gold nanoparticles were then loaded on the surface of TiO2 by a liquid-phase reduction method to give an Au/TiO2 material with good photocatalytic activity. The Au/TiO2 nanocomposite was utilized as a photocatalyst to develop a light-promoted Minisci oxidative coupling reaction of ether and aza aromatics by using oxygen as green oxidant and only catalytic amount of acid as additive. The protocol shows a good functional group tolerance as well as good to excellent yields for various substrates. With mechanistic studies, Au/TiO2 nanocomposite proved to be an efficient photocatalyst to activate C?H bond via a SEO approach of heteroatoms. Moreover, the solid semiconductor photocatalyst shows good recycling performance, could be easily recovered and reused without significant decrease in yield.
Synthesis and metal binding properties of N-alkylcarboxyspiropyrans
Perry, Alexis,Kousseff, Christina J.
, p. 1542 - 1550 (2017)
Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using 1H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M2+ binding affinity correlated with increased alkycarboxylate tether length.
Peroxyl Radical Reactions in Water Solution: A Gym for Proton-Coupled Electron-Transfer Theories
Amorati, Riccardo,Baschieri, Andrea,Morroni, Gloria,Gambino, Rossana,Valgimigli, Luca
, p. 7924 - 7934 (2016)
The reactions of alkylperoxyl radicals with phenols have remained difficult to investigate in water. We describe herein a simple and reliable method based on the inhibited autoxidation of water/THF mixtures, which we calibrated against pulse radiolysis. With this method we measured the rate constants kinh for the reactions of 2-tetrahydrofuranylperoxyl radicals with reference compounds: urate, ascorbate, ferrocenes, 2,2,5,7,8-pentamethyl-6-chromanol, Trolox, 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid, 2,6-di-tert-butyl-4-methoxyphenol, 4-methoxyphenol, catechol and 3,5-di-tert-butylcatechol. The role of pH was investigated: the value of kinh for Trolox and 4-methoxyphenol increased 11- and 50-fold from pH 2.1 to 12, respectively, which indicate the occurrence of a SPLET-like mechanism. H(D) kinetic isotope effects combined with pH and solvent effects suggest that different types of proton-coupled electron transfer (PCET) mechanisms are involved in water: less electron-rich phenols react at low pH by concerted electron-proton transfer (EPT) to the peroxyl radical, whereas more electron-rich phenols and phenoxide anions react by multi-site EPT in which water acts as proton relay. Radical kinetics: A simple and reliable method to measure the kinetics of peroxyl radical reactions in water is described (see figure). The proton-coupled electron transfer from a variety of compounds was investigated. Electron-poorer phenols react by concerted electron-proton transfer (EPT or CPET), whereas electron-richer phenols and phenoxide anions react by multi-site EPT (separated CPET) in which water acts as proton relay, similarly to the chemistry of radical enzymes.
Highly dispersed ruthenium nanoparticle-embedded mesoporous silica as a catalyst for the production of γ-butyrolactone from succinic anhydride
Chung, Sang-Ho,Eom, Hee-Jun,Kim, Min-Sung,Lee, Myung Suk,Lee, Kwan-Young
, p. 7701 - 7706 (2013)
In this study, a novel, strategic method was developed for the synthesis of a mesoporous silica catalyst embedded with ruthenium nanoparticles (RuNPs/SiO2) by combining the polyol and modified sol-gel methods. By applying this new procedure, uniformly synthesized ruthenium nanoparticles with an average size of 3.8 nm and 95% spherical shape were highly dispersed in the mesoporous silica support material. Coordinated carbonyl groups of PVP remaining from the synthesis of the RuNPs were effectively removed by the thermal treatment (calcined at 573 K for 4 h) and the sythesized RuNPs/SiO2 catalysts were reduced under hydrogen at 20 bar for 2 h. These catalysts were analyzed using transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), N2 adsorption-desorption, and X-ray diffraction (XRD). After the thermal treatment and the reduction procedure, the size and shape of the embedded RuNPs were nearly unchanged, and the catalyst was active in the liquid-phase hydrogenation of succinic anhydride (SAN) to selectively form γ-butyrolactone (GBL) with a maximum yield of 90.1%. This novel catalyst preparation is a potentially useful method for the synthesis of metal nanoparticles as heterogeneous catalysts. Copyright
Convergent Cascade Catalyzed by Monooxygenase–Alcohol Dehydrogenase Fusion Applied in Organic Media
Huang, Lei,Aalbers, Friso S.,Tang, Wei,R?llig, Robert,Fraaije, Marco W.,Kara, Selin
, p. 1653 - 1658 (2019)
With the aim of applying redox-neutral cascade reactions in organic media, fusions of a type II flavin-containing monooxygenase (FMO-E) and horse liver alcohol dehydrogenase (HLADH) were designed. The enzyme orientation and expression vector were found to influence the overall fusion enzyme activity. The resulting bifunctional enzyme retained the catalytic properties of both individual enzymes. The lyophilized cell-free extract containing the bifunctional enzyme was applied for the convergent cascade reaction consisting of cyclobutanone and butane-1,4-diol in different microaqueous media with only 5 % (v/v) aqueous buffer without any addition of external cofactor. Methyl tert-butyl ether and cyclopentyl methyl ether were found to be the best organic media for the synthesis of γ-butyrolactone, resulting in about 27 % analytical yield.
REARRANGEMENT OF 2-BUTYNE-1,4-DIOL TO BUTYROLACTONE CATALYZED BY RUTHENIUM COMPLEXES
Shvo, Youval,Blum, Yigal,Reshep, Deborah
, p. C79 - C81 (1982)
The isomerization of 2-butyne-1,4-diol to butyrolactone catalysed by ruthenium complexes is described.
Modification of γ-aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines
Glotova, Tatyana E.,Dvorko, Marina Yu.,Ushakov, Igor A.,Shabalin, Dmitrii A.,Schmidt, Elena Yu.,Trofimov, Boris A.
, p. 314 - 316 (2012)
Primary N-C adducts of γ-aminobutyric acid (GABA) to acylacetylenes undergo mild stereoselective C-vinylation by another acylacetylene molecule to afford (2E,4Z)-4-acyl-5-aminoalka-2,4-dien-1-one-type diadducts in 83-92% yields. The latter cyclize to acyl
Au/TiO2 as high efficient catalyst for the selective oxidative cyclization of 1,4-butanediol to γ-butyrolactone
Huang, Jie,Dai, Wei-Lin,Li, Hexing,Fan, Kangnian
, p. 69 - 76 (2007)
Au/TiO2 catalysts prepared by the deposition-precipitation method showed excellent activity and selectivity in the oxidative cyclization of 1,4-butanediol to γ-butyrolactone, with high yields (>99%) under mild conditions (413 K, 1.25 MPa air). Catalysts with 3-8% gold loading and calcined at 573-673 K were all highly active for the formation of γ-butyrolactone, as demonstrated by XRD, TEM, XPS, ICP and UV-vis DRS results. It is concluded that highly dispersed small (2-10 nm) gold particles are formed with the surface enrichment of gold. The ratio of cationic gold to metallic gold depends on the treatment temperature. These findings, combined with those of the activity tests, lead to the conclusion that the surface metallic nanosized gold particles are active sites. The catalyst can be reused with no drop in activity or selectivity.
Microwave-assisted reduction of levulinic acid with alcohols producing γ-valerolactone in the presence of a Ru/C catalyst
Al-Shaal, Mohammad Ghith,Calin, Marc,Delidovich, Irina,Palkovits, Regina
, p. 65 - 68 (2016)
γ-Valerolactone can be synthesized by reduction of levulinic acid and its esters in the presence of secondary alcohols as hydrogen donors and Ru/C as catalyst. The reaction rate increases when using microwave heating. Quantitative formation of γ-valerolactone was observed within 25 min at 160 °C under microwave heating based on levulinic acid and i-propanol. The reaction appears to proceed via a dehydrogenation-hydrogenation sequence.