556-52-5Relevant articles and documents
Synthesis of glycidol from glycerol and dimethyl carbonate using ionic liquid as a catalyst
Gade, Swapna M.,Munshi, Mudassir K.,Chherawalla, Batul M.,Rane, Vilas H.,Kelkar, Ashutosh A.
, p. 184 - 188 (2012)
Transesterification of dimethyl carbonate with glycerol has been investigated using various ionic liquids as catalysts. Synthesis of glycidol with high selectivity (78%) has been achieved using tetramethylammonium hydroxide ([TMA][OH]) as a catalyst at 80°C. Effect of various reaction conditions on the activity and selectivity was investigated and catalyst concentration had a significant influence on conversion as well as selectivity to glycidol. Activity as well as selectivity of the catalyst decreased significantly with increase in moisture content. Recycle experiment indicated slight drop in glycerol conversion and selectivity to glycidol because of dilution of reaction mixture and also the presence of products from the initial experiment.
Reaction of glycidyl methacrylate at the hydroxyl and carboxylic groups of poly(vinyl alcohol) and poly(acrylic acid): Is this reaction mechanism still unclear?
Reis, Adriano V.,Fajardo, Andre R.,Schuquel, Ivania T. A.,Guilherme, Marcos R.,Vidotti, Gentil Jose,Rubira, Adley F.,Muniz, Edvani C.
, p. 3750 - 3757 (2009)
(Chemical Equation Presented) Transesterification and epoxide ring-opening reactions are two mechanism routes that explain chemical modifications of macromolecules by glycidyl methacrylate (GMA). Although the coupling reaction of the GMA with macromolecul
Aerobic oxidation of methyl p-Tolyl sulfide catalyzed by a remarkably labile heteroscorpionate Ru(II)-aqua complex, fac-[RuII(H2O)(dpp)(tppm)]2+
Huynh, My Hang V.,Witham, Laura M.,Lasker, Joanne M.,Wetzler, Modi,Mort, Brendan,Jameson, Donald L.,White, Peter S.,Takeuchi, Kenneth J.
, p. 308 - 309 (2003)
fac-[RuII(Cl)(dpp)(L3)]+ (L3 = tris(pyrid-2-yl)methoxymethane (tpmm) = [1A]+ and tris(pyrid-2-yl)pentoxymethane (tppm) = [1B]+ and dpp = di(pyrazol-1-yl)propane) rapidly undergo ligand substitution with water to form fac-[RuII(H2O)(dpp)(L3)]2+ (L3 = tpmm = [2A]2+ and tppm = [2B]2+). In the structure of [2A]2+, the distorted octahedral arrangement of ligands around Ru is evident by a long Ru(1)-O(40) of 2.172(3) A and a large (40)-Ru (1)-N(51) of 96.95(14)° The remarkably short distance between O (40) of H 2O and H (45a) of dpp confirms the heteroscorpionate ligand effect fo dpp H 2O [2B] 2+ aerobically catalyzes methl p-toyl sulfide to methyl p-toyl sulfoxide in 1,2 dichlorobenzene at 25.0 ± 0.1 ° C under 11.4 psi of O2.Experimental facts in support of this aerobic sulfide oxidation are the absence of H 2O2 and the oxidative readctive of the putative Ru(IV)-oxo intermediate toward methl p-tolyl Sulfide, 2- propanol, and allyl alcohal This study provides the first documented example of aerobic-sulfide oxidation catalyzed by the remarkably labile heteroscorpionate Ru (III)- aqua complex without the formation of a highly reactive peroxide as an intemediate. Copyright
A novel titanosilicate with MWW structure III. Highly efficient and selective production of glycidol through epoxidation of allyl alcohol with H2O2
Wu, Peng,Tatsumi, Takashi
, p. 317 - 326 (2003)
The catalytic properties of Ti-MWW in the epoxidation of allyl alcohol (AAL) with hydrogen peroxide to glycidol (GLY) have been studied in detail by a comparison with those of TS-1 and pure silica Ti-Beta, and mechanical considerations have been given to the relation between the catalytic performance and the structural, acidic, and hydrophilic/hydrophobic nature of titanosilicates. Ti-MWW catalyzed the AAL epoxidation more actively and selectively than TS-1 and Ti-Beta in the presence of H2O or MeCN, and exhibited a conversion of 95% for AAL and a selectivity of 99% for GLY when the AAL epoxidation was carried out at 333 K for 30 min and at 12 wt% of catalyst to substrate. Ti-MWW proved to be a reusable and sustainable catalyst as it stood up to Ti leaching and maintained the catalytic activity and the product selectivity in the reaction-regeneration cycles. The acidic character due to the boron framework was very weak, and thus contributed negligibly to the solvolysis of GLY. The AAL epoxidation proceeded mainly within the intralayer sinusoid 10-MR channels which supplied more steric fitness to the substrate molecules than the tunnel-like channels of TS-1 ad Ti-Beta. Ti-MWW was more hydrophilic than TS-1, but much more hydrophobic than Ti-Beta. The hydrophilicity of Ti-MWW was presumed to derive mainly from the defect sites due to the incomplete dehydroxylation between the layers and partially as a result of deboronation. The sinusoidal 10-MR channels serving as the reaction space for the AAL epoxidation were considered to be hydrophobic, thus rendering the Ti-MWW catalyst applicable to the substrates and solvents, both of a polar nature.
Synthesis of glycerol carbonate by transesterification of glycerol and dimethyl carbonate over KF/γ-Al2O3 catalyst
Liu, Zhenmin,Wang, Junwei,Kang, Maoqing,Yin, Ning,Wang, Xinkui,Tan, Yisheng,Zhu, Yulei
, p. 152 - 160 (2014)
Series of KF/γ-Al2O3 solid base catalysts were prepared by a wet impregnation method and applied to the synthesis of glycerol carbonate (GC) from glycerol and dimethyl carbonate. The influences of KF loading and calcination temperature of catalyst on the synthesis were investigated. The results showed that KF/γ-A12O3 catalysts could promote glycerol conversion to GC efficiently. The structure and properties of the catalysts were studied by means of X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), N2-adsorption, CO2-temperature programmed desorption (TPD), X-ray photoelectron spectroscopy (XPS) and Hammett indicator method. It was found that several types of basic centers such as KF, KAlO2, KOH and possibly coordinately unsaturated F-ion existed on the catalysts. The strong basic centers could not only accelerate the conversion of glycerol, but also enhance the formation of glycidol from the decomposition of GC. The recycling of KF/γ-A1 2O3 revealed that deactivation of catalyst was strengthened with the reuse times, which was mainly caused by the partial leaching of active potassium species. High calcination temperature favored the transformation of KF to KAlO2 and alleviated the deactivation of the catalyst. Based on the product distribution and obtained results, a possible reaction mechanism on reaction of glycerol with dimethyl carbonate was proposed.
Consecutive carbonylation and decarboxylation of glycerol with urea for the synthesis of glycidol via glycerol carbonate
Endah, Yohana Kurnia,Kim, Min Soo,Choi, Jisik,Jae, Jungho,Lee, Sang Deuk,Lee, Hyunjoo
, p. 136 - 141 (2017)
Zn(OAc)2-catalyzed carbonylation and decarboxylation of glycerol and urea for the synthesis of glycidol were conducted at 150?°C, 2.7?kPa for 2?h and 170?°C, 2.0?kPa for 1.5?h, respectively. When the reaction conducted in a one-pot consecutive way, the yield of glycidol was 20%. However, when the formed zinc glycerolate (Zn(C3H6O3)) was filtered out after the carbonylation, the yield increased to 50% with respect to the amount of glycerol, whereas the yields of glycidol were very low when other zinc salts such as ZnCl2, ZnSO4 and Zn(NO3)2, were used as catalysts. The high catalytic activity of Zn(OAc)2 for this carbonylation and decarboxylation of glycerol and urea could be ascribed to the formation of Zn(NH3)x(OAc)2, which was determined from IR and TOF-SIMS studies.
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Achrem et al.
, p. 3165,3166 - 3169 (1974)
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Catalytic epoxidation by perrhenate through the formation of organic-phase supramolecular ion pairs
Cokoja, Mirza,Markovits, Iulius I. E.,Anthofer, Michael H.,Poplata, Saner,P?thig, Alexander,Morris, Danny S.,Tasker, Peter A.,Herrmann, Wolfgang A.,Kühn, Fritz E.,Love, Jason B.
, p. 3399 - 3402 (2015)
Organic-phase supramolecular ion pair (SIP) host-guest assemblies of perrhenate anions (ReO4-) with ammonium amide receptor cations are reported. These compounds act as catalysts for the epoxidation of alkenes by aqueous hydrogen peroxide under biphasic conditions and can be recycled several times with no loss in activity.
Synthesis of glycerol 1,2-carbonate by transesterification of glycerol with dimethyl carbonate using triethylamine as a facile separable homogeneous catalyst
Ochoa-Gomez, Jose R.,Gomez-Jimenez-Aberasturi, Olga,Ramirez-Lopez, Camilo,Maestro-Madurga, Belen
, p. 3368 - 3376 (2012)
The synthesis of glycerol 1,2-carbonate (GC) by transesterification of glycerol with dimethyl carbonate (DMC) using triethylamine (TEA) as a facile separable homogeneous catalyst has been studied at different temperatures, DMC/glycerol molar ratios and TE
Deuterium magnetic resonance as a probe for organic reaction mechanisms: Epoxidation of 1(3)-tosylglycerol is a pure SN2 cyclisation
Rabiller,Mesbahi,Levayer
, p. 187 - 190 (1991)
A stereoselective deuteriation of glycerol acetonide is used to prove by means of deuterium NMR spectroscopy that the cyclisation of glycerol tosylate into glycidol is a pure SN2 mechanism.
High-efficiency and low-cost Li/ZnO catalysts for synthesis of glycerol carbonate from glycerol transesterification: The role of Li and ZnO interaction
Song, Xianghai,Wu, Yuanfeng,Cai, Fufeng,Pan, Donghui,Xiao, Guomin
, p. 77 - 85 (2017)
A series of efficient and low-cost Li/ZnO catalysts were prepared by a simple impregnation method and investigated for the synthesis of glycerol carbonate (GC) from the transesterification of glycerol with dimethyl carbonate (DMC). The Li/ZnO catalysts were characterized using XRD, SEM, FT-IR, TG-DSC, TPD and XPS. It was found that the basicity of the catalysts highly depended on the Li loading and calcination temperature. The weak and moderate basic sites on the catalyst surfaces originated from the ZnO and Li+interaction. The strong basic sites were attributed to the substitution of Zn2+by Li+in the ZnO lattice, which led to straining of Zn-O bonds and the formation of [Li+O?] species. It was the strong basic sites rather than the weak and moderate basic sites that catalyzed the transesterification of glycerol with DMC. The highest catalytic activity was observed over the ZnO loaded with 1 wt.% LiNO3and calcined at 500 °C. Glycerol conversion of 97.40% and GC yield of 95.84% were obtained over this catalyst at 95 °C in 4 h.
Role of Organic Fluoride Salts in Stabilizing Niobium Oxo-Clusters Catalyzing Epoxidation
Dai, Sheng,Ding, Bingjie,Gong, Xueqing,Hou, Zhenshan,Li, Difan,Tang, Xuan,Xu, Beibei,Yao, Yefeng,Zhang, Tong,Zheng, Anna,Zhou, Qingqing
, p. 8190 - 8203 (2021/07/26)
We present here that easily available organic salts can stabilize/modify niobium (Nb) oxo-clusters. The as-synthesized Nb oxo-clusters have been characterized by various methods. These Nb oxo-clusters were catalytically active for the epoxidation of allylic alcohols and olefins with H2O2 as an oxidant. Notably, Nb-OC@TBAF-0.5 appeared as highly dispersed nanosized particles and showed the highest catalytic activity, which can be attributed to the following reasons on the basis of characterization. First, the strong coordination of fluorine ions with Nb sites and the steric protection with bulky organic cations led to high stabilization and dispersion of the oxo-clusters in the course of the reaction. Second, a hydrogen-bond interaction between the coordinated fluorine atom and the -OH group of allylic alcohol favored the epoxidation reaction. Third, the electron density of Nb sites decreased due to the strong electron-withdrawing ability of F- adjacent to Nb sites, thus promoting the electrophilic oxygen transfer to the CC bond.
Preparation of zeolitic bismuth vanadomolybdate using a ball-shaped giant polyoxometalate for olefin epoxidation
Hara, Michikazu,Li, Denan,Li, Yanshuo,Ueda, Wataru,Zhang, Zhenxin,Zhu, Qianqian
, p. 21624 - 21630 (2021/12/09)
Zeolitic octahedral metal oxides are interesting materials that have received increasing attention. A bismuth vanadomolybdate-based zeolitic octahedral metal oxide was synthesized using a ball-shaped polyoxovanadomolybdate with different Bi sources. The material was used as a heterogeneous catalyst for olefin epoxidation. Different olefins were converted to their corresponding epoxides by the catalyst under mild conditions. This robust catalyst was reused several times without loss of activity.
