693-65-2Relevant articles and documents
Catalytic reactions using superacids in new types of ionic liquids
Harmer, Mark A.,Junk, Christopher P.,Rostovtsev, Vsevolod V.,Marshall, William J.,Grieco, Liane M.,Vickery, Jemma,Miller, Robert,Work, Stella
, p. 517 - 525 (2009)
We will describe the use of superacids, in particular 1,1,2,2- tetrafluoroethanesulfonic acid (TFESA) and 1,1,2,3,3,3-hexafluoropropanesulfonic acid (HFPSA) in the presence of ionic liquids for improved chemical processing for a range of industrially important chemical reactions. In a number of cases the reaction mixture starts as a single phase, allowing for high reactivity, then separates into two phases upon completion of the reaction. This allows for ease of product separation P. T. Anastas and T. C. Williamson, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford University Press, 1998.1
Breaking C-O Bonds with Uranium: Uranyl Complexes as Selective Catalysts in the Hydrosilylation of Aldehydes
Monsigny, Louis,Thuéry, Pierre,Berthet, Jean-Claude,Cantat, Thibault
, p. 9025 - 9033 (2019/10/02)
We report herein the possibility to perform the hydrosilylation of carbonyls using actinide complexes as catalysts. While complexes of the uranyl ion [UO2]2+ have been poorly considered in catalysis, we show the potentialities of the Lewis acid [UO2(OTf)2] (1) in the catalytic hydrosilylation of a series of aldehydes. [UO2(OTf)2] proved to be a very active catalyst affording distinct reduction products depending on the nature of the reductant. With Et3SiH, a number of aliphatic and aromatic aldehydes are reduced into symmetric ethers, while iPr3SiH yielded silylated alcohols. Studies of the reaction mechanism led to the isolation of aldehyde/uranyl complexes, [UO2(OTf)2(4-Me2N-PhCHO)3], [UO2(μ-κ2-OTf)2(PhCHO)]n, and [UO2(μ-κ2-OTf)(κ1-OTf)(PhCHO)2]2, which have been fully characterized by NMR, IR, and single-crystal X-ray diffraction.
Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts
Bayguzina,Gimaletdinova,Khusnutdinov
, p. 1148 - 1155 (2018/10/24)
Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.
Solvent- and Metal-free Oxidative Esterification of Aromatic Aldehydes Using Urea-2,2-dihydroperoxypropane as a New Solid Oxidant
Khosravi, Kaveh,Khalaji, Kobra,Naserifar, Shirin
, p. 303 - 309 (2017/03/27)
Urea-2,2-dihydroperoxypropane as a noble and solid gem-dihydroperoxide derivative was used to transform various aromatic aldehydes to their corresponding benzoate derivatives in the presence of HBr under mild conditions at room temperature in high yields and short reaction times.
Cellulose oxidation and the use of carboxyl cellulose metal complexes in heterogeneous catalytic systems to promote suzuki-miyaura coupling and C?O bond formation reaction
Martins, Guilherme B. C.,Dos Santos, Marcelo R.,Rodrigues, Marcus V. R.,Sucupira, Renata R.,Meneghetti, Luisa,Monteiro, Adriano L.,Suarez, Paulo A. Z.
, p. 2064 - 2072 (2017/09/23)
This work shows the modification of microcrystalline cellulose by the selective oxidation of primary hydroxyl groups to carboxylate groups by a 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-mediated system and its application as a heterogeneous ligand by ionic exchange with catalytic metals ions such as palladium, nickel and copper. Afterwards is described the application of the synthesized material as catalyst in coupling reactions such as Suzuki-Miyaura coupling and C?O bond formation reaction in different conditions, which are of great importance for the synthesis of drugs, natural products and new materials such as dendrimers, liquid crystals and polymers with magnetic and optical properties. The carboxyl cellulose matrix shows to have superior catalytic results as a ligand for all coupling reactions. Can be also highlighted the affinity of the carboxyl cellulose ligand in polar solvents such as water and alcohols and its application in mild conditions.
PROCESS FOR THE PRODUCTION OF DIPENTYL ETHER FROM LEVULINIC ACID RESULTING FROM BIOMASS
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Page/Page column 17, (2016/09/22)
A process for the production of dipentyl ether from levulinic acid resulting from biomass including at least one polysaccharide comprising the following steps: (a) reacting said levulinic acid in the presence of hydrogen and at least one non-acid hydrogenation catalyst obtaining γ-valerolactone; (b) reacting said γ-valerolactone in the presence of hydrogen and at least one acid hydrogenation catalyst obtaining pentanoic acid; (c) reacting said pentanoic acid in the presence of hydrogen and at least a catalyst comprising platinum (Pt) and tin (Sn) obtaining pentyl alcohol; (d) reacting said pentyl alcohol in the presence of at least one solid acid catalyst thereby obtaining dipentyl ether. The dipentyl ether thus obtained can be advantageously used as an oxygenated component for fuels for diesel engines.
Organohalide-catalyzed dehydrative O-alkylation between alcohols: A facile etherification method for aliphatic ether synthesis
Xu, Qing,Xie, Huamei,Chen, Pingliang,Yu, Lei,Chen, Jianhui,Hu, Xingen
supporting information, p. 2774 - 2779 (2015/05/27)
Organohalides are found to be effective catalysts for dehydrative O-alkylation reactions between alcohols, providing selective, practical, green, and easily scalable homo- and cross-etherification methods for the preparation of useful symmetrical and unsymmetrical aliphatic ethers from the readily available alcohols. Mechanistic studies revealed that organohalides are regenerated as reactive intermediates and recycled to catalyze the reactions.
Magnetic Polystyrene Nanosphere Immobilized TEMPO: A Readily Prepared, Highly Reactive and Recyclable Polymer Catalyst in the Selective Oxidation of Alcohols
Zheng, Zhi,Wang, Jianli,Zhang, Miao,Xu, Lixin,Ji, Jianbing
, p. 307 - 312 (2013/03/13)
The 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical immobilized on the magnetic polystyrene nanospheres (MPNs) was used as a recyclable catalyst in the oxidation of various alcohols. The new and simply prepared heterogeneous TEMPO/MPNs exhibits both similar versatility and efficiency to homogeneous TEMPO under basic Montanari conditions. The excellent stability of the MPNs enables the TEMPO/MPNs to be recycled more than 20times without significant leaching of immobilized TEMPO radicals or degradation of Fe3O4 nanoparticles. Moreover, the magnetic response ensures the rapid separation and quantitative recycling of TEMPO/MPNs by simple magnetic decantation.
Intermolecular dehydration of alcohols by the action of copper compounds activated with carbon tetrabromide. synthesis of ethers
Khusnutdinov, R. I.,Bayguzina, A. R.,Gimaletdinova, L. I.,Dzhemilev, U. M.
, p. 1191 - 1196,6 (2020/10/15)
Copper compounds of the general formula CuXn (X = Cl, Br, I, acac, OAc, C7H4O3, C7H 5O2; n = 1, 2) activated by carbon tetrabromide catalyzed intermolecular dehydration of primary and secondary alcohols with formation of the corresponding ethers.
Copper(II) triflate-catalyzed reduction of carboxylic acids to alcohols and reductive etherification of carbonyl compounds
Zhang, Yin-Jie,Dayoub, Wissam,Chen, Guo-Rong,Lemaire, Marc
experimental part, p. 7400 - 7407 (2012/09/10)
A protocol is described for the reduction of carboxylic acids to primary alcohols using 1,1,3,3-tetramethyldisiloxane (TMDS) and a catalytic amount of Cu(OTf)2. Aliphatic as well as aromatic carboxylic acids are reduced in high selectivity and good yields. TMDS/Cu(OTf)2 has also been found to be an efficient catalytic reducing system for the preparation of symmetrical ethers from carbonyl compounds under mild conditions.
