111-13-7Relevant articles and documents
Selective ruthenium-catalyzed oxidation of 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose and other alcohols with NaOCl
Gonsalvi, Luca,Arends, Isabel W. C. E.,Sheldon, Roger A.
, p. 1659 - 1661 (2002)
Matrix presented The asymmetric epoxidation catalyst 1,2:4,5-di-O-isopropylidene-β-D-erythro-2,3-hexadiulo-2,6-pyranose 2 was obtained in high yield from 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose 1 via a recyclable ruthenium-catalyzed hypochlorite oxidation protocol under biphasic conditions (MTBE/water) in the presence of an alkaline buffer (pH 9.5). Other secondary alcohols were also oxidized selectively to the correspondinq ketones.
Promoting effect of water for aliphatic primary and secondary alcohol oxidation over platinum catalysts in dioxane/aqueous solution media
Frassoldati, Antonio,Pinel, Catherine,Besson, Michle
, p. 81 - 88 (2011)
In the selective oxidation with air of 1-octanol and 2-octanol in 1,4-dioxane at 100 °C and 10 bar in the presence of carbon supported platinum catalysts, the catalytic activity could be impressively boosted by substitution of pure dioxane by increasing amounts of water. Changing the polarity of the solvent strongly influences the adsorption equilibrium of substrates and products at the catalyst surface and hence plays an influential role on the reaction rate.
Engineering of P450pyr hydroxylase for the highly regio- and enantioselective subterminal hydroxylation of alkanes
Yang, Yi,Liu, Ji,Li, Zhi
, p. 3120 - 3124 (2014)
Terminal-selective cytochrome P450pyr has been successfully engineered through directed evolution for the subterminal hydroxylation of alkanes with excellent regio- and enantioselectivity. A sensitive colorimetric high-throughput screening (HTS) assay was developed for the measurement of both the regioselectivity and the enantioselectivity of a hydroxylation reaction. By using the HTS assay and iterative saturation mutagenesis, sextuple-mutant P450pyrSM1 was created for the hydroxylation of n-octane (1) to give (S)-2-octanol (2) with 98 % ee and >99 % subterminal selectivity. The engineered P450 is the first enzyme for this type of highly selective alkane hydroxylation, being useful for the Ci-H activation and functionalization of alkanes and the preparation of enantiopure alcohols. Molecular modeling provided structure-based understanding of the fully altered regioselectivity and the excellent enantioselectivity. Another sextuple-mutant P450pyrSM2 catalyzed the hydroxylation of propylbenzene (3) to afford (S)-1-phenyl-2-propanol (4) with 95 % ee and 98 % subterminal selectivity. Get a handle on it: Highly regio- and enantioselective subterminal hydroxylation of n-octane and propylbenzene was observed with P450 enzymes obtained by the directed evolution of terminal-selective P450pyr hydroxylase (see scheme). The engineered enzymes with their fully altered selectivities are useful for the functionalization of alkanes and the preparation of enantiomerically pure alcohols.
A novel heteropolyanion-based amino-containing cross-linked ionic copolymer catalyst for epoxidation of alkenes with H2O2
Leng, Yan,Zhang, Weijie,Wang, Jun,Jiang, Pingping
, p. 306 - 311 (2012)
A heteropolyanion-based cross-linked ionic copolymer was prepared by the anion-exchange of a newly task-specific designed amino-containing ionic copolymer with a Keggin heteropolyacid, and characterized by FT-IR, SEM, TG, XRD, UV-vis, ESR, 1H NMR, and elemental analysis. Its catalytic activity was evaluated in the epoxidation of alkenes with aqueous H 2O2. The resultant heteropolyanion-based ionic copolymer is revealed to be a highly efficient heterogeneous catalyst for epoxidation of alkenes with H2O2, adding the advantages of convenient recovery and steady reuse.
Microstructured Au/Ni-fiber catalyst for low-temperature gas-phase selective oxidation of alcohols
Zhao, Guofeng,Hu, Huanyun,Deng, Miaomiao,Lu, Yong
, p. 9642 - 9644 (2011)
Galvanic deposition of Au onto a thin-sheet sinter-locked 8 μm Ni-fiber delivers a high-performance Au/Ni-fiber catalyst for alcohol oxidation, due to the unique combination of excellent heat conductivity, remarkable low-temperature activity, and good stability/regenerability. The special NiO@Au ensembles formed during the reaction contribute to promoting the low-temperature activity. The Royal Society of Chemistry 2011.
Gold supported on a biopolymer (chitosan) catalyzes the regioselective hydroamination of alkynes
Corma, Avelino,Concepcion, Patricia,Dominguez, Irene,Forne, Vicente,Sabater, Maria J.
, p. 39 - 47 (2007)
Gold nanoparticles on a polysaccharide-based support (chitosan) were found to catalyze with very high yields the regioselective hydroamination of alkynes without the need for acid promoters and inert atmosphere. The metal-support interactions were studied by Raman, IR, UV, and NMR spectroscopy. The interaction between gold and the NH and OH groups of chitosan allow good dispersion of the nanocrystals on the biopolymer. The chitosan-silica composite further stabilizes gold nanoparticles against agglomeration or leaching compared with other supports.
New Cleavable Surfactants Derived from Glucono-1,5-Lactone
Kida, Toshiyuki,Morishima, Nobuaki,Masuyama, Araki,Nakatsuji, Yohji
, p. 705 - 710 (1994)
New amido nonionic cleavable surfactants were synthesized in good yields by the acetalization of glucono-1,5-lactone with octanal, 2-octanone or 2-undecanone, followed by amidation with monoethanolamine, diethanolamine or morpholine.These compounds possessed good water solubilities.The compounds derived from 2-octanone showed higher critical micelle concentrations than the compounds from octanal.For the same hydrophobic chain, both the micelle-forming property and the ability to lower surface tension increased with the change in the terminal amide group in the orderdiethanolamide morpholide monoethanolamide.Interestingly, in spite of their relatively short hydrophobic chains, these compounds showed greater ability to lower surface tension than conventional nonionic surfactants, such as alcohol ethoxylates.Furthermore, their acid-decomposition properties were determined.Their decomposition rates were also compared with that of the corresponding carboxylate type of compound derived from glucono-1,5-lactone. KEY WORDS: Acid-decomposition properties, cleavable surfactant, glucono-1,5-lactone, sugar-derived surfactant, surface-active properties.
Selective oxidation of alcohols by orthorhombic Mo-V-O phase with molecular oxygen
Wang, Feng,Ueda, Wataru
, p. 184 - 185 (2008)
We have investigated heterogeneous oxidation of alcohols using crystalline molybdenum vanadium oxide (Mo-V-O) as catalyst with molecular oxygen as oxidant. The major product from primary alcohol was aldehyde, the secondary alcohol was mainly dehydrated to olefin, and the oxidation of cyclic alcohols chiefly afforded ketones. A Hammett plot suggested that hydride abstraction might be involved in the reaction step. We have discussed possible reaction mechanism based on substrate adsorption and activation on catalytically active sites. Copyright
Evaluation of tuned phosphorus cavitands on catalytic cross-dimerization of terminal alkynes
Endo, Naoki,Kanaura, Mao,Schramm, Michael P.,Iwasawa, Tetsuo
, p. 4754 - 4757 (2016)
Synthesis of four new bis-phosphorus cavitands is described, including a description of their catalytic use on cross-dimerization of terminal alkynes. The commercially available P[N(CH2CH3)2]3, PhP[N(CH2CH3)2]2, P(OCH3)3, and in situ generated P(NMeBn)3were reacted with a tetra-ol cavitand platform to provide new phosphorus ligands. These ligands readily formed bis-Au complexes that were examined to generate a reactivity profile for the catalytic cross-dimerization of terminal alkynes. We found that the ligand derived from P[N(CH3)2]3gave best product selectivity.
Application of hydrogen peroxide encapsulated in silica xerogels to oxidation reactions
Bednarz, Szczepan,Rys, Barbara,Bogda, Dariusz
, p. 8068 - 8078 (2012)
Hydrogen peroxide was encapsulated into a silica xerogel matrix by the sol-gel technique. The composite was tested as an oxidizing agent both under conventional and microwave conditions in a few model reactions: Noyori′s method of octanal and 2-octanol oxidation and cycloctene epoxidation in a 1,1,1-trifluoroethanol/Na2WO4 system. The results were compared with yields obtained for reactions with 30% H2O2 and urea-hydrogen peroxide (UHP) as oxidizing agents. It was found that the composite has activity similar to 30% H2O2 and has a several advantages over UHP such as the fact that silica and H2O are the only products of the composite decomposition or no contamination by urea or its derivatives occurs; the xerogel is easier to heated by microwave irradiation than UHP and could be used as both an oxidizing agent and as solid support for microwave assisted solvent-free oxidations.
