- Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1
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A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.
- Chu, Qingyan,He, Guangke,Xi, Yang,Wang, Ping,Yu, Haoxuan,Liu, Rui,Zhu, Hongjun
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- Green synthesis method for preparing nitroalkanes by oxime oxidation
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The invention belongs to the field of organic chemical industries, and provides a green synthesis method for preparing nitroalkanes by oxime oxidation. At the temperature of 55 to 120 DEG C and under the pressure of 0 to 1.0 MPa, oxime, a solvent and hydrogen peroxide are reacted for 20 to 200min in the presence of certain amounts of nanoporous skeleton metal hybrid catalysts and cocatalysts, a reaction liquid is subjected to membrane separation, the catalysts can be repeatedly used for more than 7 times, and distilled to obtain nitroalkane products, the purity of the products is not less than 99%, and the yield of the products is not less than 95%. Furthermore, the green synthesis method for preparing nitroalkanes by the oxime oxidation disclosed by the invention is a green synthesis method of nitroalkanes, and suitable for large-scale industrialized production.
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Paragraph 0053; 0054
(2017/08/29)
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- BIS-HETEROARYL DERIVATIVES AS MODULATORS OF PROTEIN AGGREGATION
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The present invention relates to certain bis-heteroaryl compounds, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, Parkinson's disease with dementia, fronto- temporal dementia, Huntington's Disease, amyotrophic lateral sclerosis, and multiple system atrophy, and cancer including melanoma.
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Paragraph 0203
(2017/02/24)
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- Organocatalytic enantioselective formal C(sp2)-H alkylation
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An organocatalytic enantioselective formal C(sp2)-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.
- Manna, Madhu Sudan,Mukherjee, Santanu
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supporting information
p. 130 - 133
(2015/01/30)
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- Core-shell palladium nanoparticle@metal-organic frameworks as multifunctional catalysts for cascade reactions
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Uniform core-shell Pd@IRMOF-3 nanostructures, where single Pd nanoparticle core is surrounded by amino-functionalized IRMOF-3 shell, are prepared by a facile mixed solvothermal method. When used as multifunctional catalysts, the Pd@IRMOF-3 nanocomposites exhibit high activity, enhanced selectivity, and excellent stability in the cascade reaction. Both experimental evidence and theoretical calculations reveal that the high catalytic performance of Pd@IRMOF-3 nanocomposites originates from their unique core-shell structures.
- Zhao, Meiting,Deng, Ke,He, Liangcan,Liu, Yong,Li, Guodong,Zhao, Huijun,Tang, Zhiyong
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supporting information
p. 1738 - 1741
(2014/03/21)
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- NITRATED HYDROCARBONS, DERIVATIVES, AND PROCESSES FOR THEIR MANUFACTURE
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Provided is a process for the formation of nitrated compounds by the nitration of hydrocarbon compounds with dilute nitric acid. Also provided are processes for preparing industrially useful downstream derivatives of the nitrated compounds, as well as novel nitrated compounds and derivatives, and methods of using the derivatives in various applications.
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Page/Page column 27-30; 33
(2009/12/02)
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- Synthesis of nitroalkanes from alkylhalides under mild and nonaqueous conditions by using polymer supported nitrites
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Alkyl halides are efficiently converted to their corresponding nitroalkanes under mild and nonaqueous conditions by using polymer supported nitrites. The polymeric reagent is regenerable.
- Zarchi, Mohammad Ali Karimi,Zarei, Amin
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p. 309 - 311
(2007/10/03)
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- Chromium Silicalite-2 (CrS-2): an Efficient Catalyst for the Direct Oxidation of Primary Amines to Nitro Compounds with TBHP
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A chromium-containing medium-pore molecular sieve (Si:Cr > 140:1) having MEL (CrS-2) topology efficiently catalyses the direct oxidation of various primary amines to the corresponding nitro compounds using 70percent tert-butyl hydroperoxide (TBHP) as the oxidant.
- Jayachandran, B.,Sasidharan, M.,Sudalai, A.,Ravindranathan, T.
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p. 1523 - 1524
(2007/10/02)
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- Catalytic selective oxidation of amines with hydroperoxides over molecular sieves: Investigations into the reaction of alkylamines, arylamines, allylamines and benzylamines with H2O2 and TBHP over TS-1 and CrS-2 as the new catalyst
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The liquid phase oxidation of various substituted amines with dil H2O2 and tert-butyl hydroxyperoxide (TBHP) has been investigated over titanium and chromium silicates respectively. While TS-1/H2O2 combination exhibits a remarkable activity and selectivity in the oxidation of arylamines to produce the symmetrical azoxybenzenes, CrS-2 catalyzes the selective oxidation of various substituted amines to the corresponding nitro compounds by oxidation with 70% TBHP. The nature of the reactive intermediates during the oxidation of anilines to nitrobenzenes has been established using cyclic voltammetry experiments. Further, amines possessing α C-H bonds are selectively oxidized to either oximes or the carbonyl compounds on reaction with H2O2 catalyzed by TS-1.
- Suresh,Joseph,Jayachandran,Pol,Vinod,Sudalai,Sonawane,Ravindranathan
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p. 11305 - 11318
(2007/10/02)
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- Action d'un Tetrafluoroborate d'Oxaziridinium sur les Amines et les Imines
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The Oxaziridinium salt 1 derived from dihydroisoquinolin is an oxygen transfer reagent to primary amines leading to nitrosoderivatives (if R = Alkyl) or nitro compounds (if R = Aryl), to tertiary amines leading to N-oxides, and to secondary amines and imines leading to the corresponding nitrone.
- Hanquet, Gilles,Lusinchi, Xavier
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p. 12185 - 12200
(2007/10/02)
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- SYNTHESIS OF LOW-MOLECULAR NITROPARAFFINS IN IONIC MELTS
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It was shown that pure low-molecular nitroparaffins can be synthesized by the reaction between alkyl sodium sulfates and nitrite ion in ionic melts.The yield of the product is temperature controlled.Because of the ambident nature of nitrite ion, the main side product is alkyl nitrite, subsequent decomposition of which results in formation of a series of organic oxygen-containing compounds.The formal kinetics of the alkylation of nitrite ion by alkyl sodium sulfates was found to be described by the first-order equation.
- Belobrzhetskaya, M. K.,Laskin, B. M.,Malin, A. S.
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p. 105 - 108
(2007/10/02)
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- Spectrochemical analysis of the laser-induced nitration of three cycloalkanes
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The tunable continuous wave carbon dioxide laser-induced reactions of cyclopropane, cyclobutane and cyclopentane with NO2 have been carried out under a variety of reaction conditions.Presented herein is our qualitative Fourier transform infrared spectroscopy and gas chromatography - mass spectroscopy spectrochemical analysis of the product mixtures.Optimal conditions were found for producing nitrocycloalkanes while reducing or eliminating the production of undesirable products.The array of products was found to be highly sensitive to the specific reaction conditions.
- Stanley, Ann E.,Godbey, Susan E.,Bonicamp, Judith M.,Ludwick, Larry M.
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p. 1987 - 1998
(2007/10/02)
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- A Beckmann-Type Dehydration of n-Butyraldoxime Catalyzed by Cytochrome P-450
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n-Butyraldoxime undergoes a unique NADPH-dependent, Beckmann-type dehydration catalyzed by rat liver microsomes to give n-butyronitrile.
- DeMaster, Eugene G.,Shirota, Frances N.,Nagasawa, Herbert T.
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p. 5074 - 5075
(2007/10/02)
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- Tetraphenylphosphonium Nitrites
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Three different forms of tetraphenylphosphonium nitrite have been found to exist: an ionic nitrite, a co-ordinated nitrite, and a molecular species.
- Clark, James H.,Macquarrie, Duncan J.
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p. 229 - 230
(2007/10/02)
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- CHEMICAL MODIFICATION OF POLY-VINYLBENZYLTRIPHENYLPHOSPHONIUM SALTS AND THEIR APPLICATIONS AS REAGENTS IN ORGANIC SYNTHESIS
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Insoluble polymer-bound reagents derived from poly(vinylbenzyltriphenylphosphonium salts) have been prepared and used as reagents in organic synthesis.The polymer-supported borohydride was used as reducing agent towards carbonyl compounds.The reaction of polymer-supported thiocyanate and nitrile anions with alkyl halides in hydrocarbon solvents gave good yields of the corresponding alkyl thiocyanates and nitroalkanes, respectively.In addition, polymer-bound carboxylate, phenoxide, and sulfinate anions were used for the synthesis of esters, ethers, and sulfones by reaction with alkyl halides in non-polar solvents.
- Akelah, Ahmed,Abdel Galil, Fathy M.
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- A NEW SYNTHESIS OF NITRO COMPOUNDS USING DIMETHYLDIOXIRANE
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Dimethyldioxirane oxidizes primary amines to nitro compounds in a facile, mild, high yield process.
- Murray, Robert W.,Jeyaraman, Ramasubbu,Mohan, Lily
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p. 2335 - 2336
(2007/10/02)
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- Formation of Organic Nitro-compounds in Flowing H2O2+NO2+N2+Organic Vapour Systems. Part 2.-H2O2+NO2+N2+Alkane System
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The principal products from the surface-initiated reactions in flowing mixtures of H2O2, NO2,N2 and RH, where RH=ethane, propane, n-butane and n-pentane, have been identified as the nitroalkane, alkyl nitrite and alkyl nitrate.The product yields have been measured; in the case of propane the variation of the yields with total gas pressure has also been studied.Values have been obtained for the relative rates of primary and secondary H-atom abstraction from each alkane by OH and for the rate-constant ratios k3/k4 and k5/k6 at 298 K:.The trends in the product yields with the variation of pressure and change of R indicate that RO radicals are produced via reactions (4)-(6) rather than by a single-step reaction of R with NO2.
- Baulch, Donald L.,Campbell, Ian M.,Chappel, Jonathan M.
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p. 609 - 616
(2007/10/02)
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- FREE RADICAL SUBSTITUTION. PART 34. THE CHLORINATION OF 1- AND 2-NITROBUTANES IN THE GAS AND LIQUID PHASES
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1- and 2-nitrobutanes have been chlorinated in the gas phase and in solution.The intermediate nitrobutyl radicals with the nitro-group in a β-position are unstable and in the gas phase lose NO2 to yield the corresponding butene.The relative rates of attack at the various sites have been determined.The nitro-group proves to be the most deactivating non-ionic substituent studied so far.
- Saeed-y-Atto,Potter, Alan,Singh, Hari,Tedder, John M.
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p. 139 - 142
(2007/10/02)
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- Removal of stannic chloride
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Stannic chloride is removed from organic solvent-based waste streams by precipitating the salt as a dimethyl sulfoxide complex.
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- Preparation of carboxylic acids from salts of nitroketones
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A method of preparing carboxylic acids is provided by contacting an ammonium, Group IA or Group IIA metal salt of a nitroketone in an aqueous medium. The method is preferably undertaken in the presence of an acidic mineral acid salt.
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