1643-20-5Relevant articles and documents
Effect of pH on Carbon-13 NMR Spectra of N-Dodecyl-N,N-dimethylamine Oxide Solution
Brycki, Bogumil,Szafran, Miroslaw
, p. 535 - 543 (1992)
Carbon-13 NMR chemical shifts of the non-ionic-cationic surfactant N-dodecyl-N,N-dimethylamine oxide (C12DAO) were measured and identified by an INADEQUATE experiment.On micellization, downfield chemical shifts were found for all carbon atoms except NCH2.The shifts are most pronounced for the carbon atoms in the central part of the chain.Protonation of the micelles resulted in upfield shifts of all the carbon atoms; the magnitudes decreased with increasing distance from the nitrogen atom.A plot of several chemical shifts against pH gave titration curves and pKa values.The pKa values vary with the carbon atom used in the calculation (from pKa = 5.05 to 5.66).An AM1 calculation of the charge densities suggests that these variations in pKa are caused by the electric field of the OH group.The effect of N-oxidation on the chemical shifts of the carbon atoms in five solvents was estimated. Key Words: 13C NMR - INADEQUATE - Dodecyldimethylamine oxide - Micelles
Aggregation Numbers of Dodecyldimethylamine Oxide Micelles in Salt Solutions
Kaimoto, Hideki,Shoho, Kouki,Sasaki, Shigeo,Maeda, Hiroshi
, p. 10243 - 10248 (1994)
Micellel aggregation number m of dodecyldimethylamine oxide was determined as a function of the micelle composition or the degree of ionization of the micelle αM in 0.1 and 0.2 M NaCl at 25 deg C with light scattering and the steady state fluorescence probe method.The two methods gave consistent results in most cases.The aggregation numbers at the critical micelle concentration (cmc) were nearly identical for both cationic and nonionic micelles: about 70 and 80 in 0.1 and 0.2 M NaCl, respectively.The aggregation number increased as αM approached 0.4-0.5.The maximum values were about 100 and 150 for 0.1 and 0.2 M NaCl.At intermediate compositions, the Rayleight ratio of the scattered light incerased with the concentration, and this increase was interpreted as the increase of micelle size with concentration.Apparent aggregation numbers at a finite concentration were evaluated on the assumption of negligible contribution from the second virial coefficient.The idea of the growth of micelles was supported by dynamic light scattering but not by the fluorescence probe method.From the observed variation of the aggregation number at cmc with αM the width of the aggregation number distribution of nonionic micelles is estimated on the basis of a simple theory.
Novel low viscous, green and amphiphilic N-oxides/phenylacetic acid based Deep Eutectic Solvents
Germani, Raimondo,Orlandini, Matteo,Tiecco, Matteo,Del Giacco, Tiziana
, p. 233 - 239 (2017)
Four novel Deep Eutectic Solvents (DESs) were prepared by mixing phenylacetic acid (which is a natural molecule present in honey) with amine N-oxides, which are molecules easily biodegradable in nature. Three of these N-oxides are amphiphilic. The novel DESs have very low freezing points (from ??34?°C to 20?°C) and they have very low viscosity, much lower than the most common and used DES in literature so far (choline chloride/urea mixture). The conductivity values resulted low and the ionicity analysis showed these DESs to be “super ionic”. Their polarity resulted high enough and it can be compared with other commonly used solvents or ionic liquids.
Kinetics and Preparation of Amine Oxides
Toney, C. Joe,Friedli, F. E.,Frank, P. J.
, p. 793 - 794 (1994)
A kinetic model for the oxidation of dimethyllaurylamine to its amine oxide with hydrogen peroxide was developed.It is a second-order reaction where k=.0250, .0079 and .0037 kg per mol/min at 75, 60 and 50 deg C, respectively.Amine oxides of N-lauryl morpholine, piperidine and 3-methyl piperidine were synthesized, and their rates of formation were determined.Compared to dimethyllaurylamine, the piperidines react slower, while the morpholine reaction is much faster. KEY WORDS: Amine oxides, dimethyllaurylamine, foam stabilizers, hydrogen peroxide, kinetics, morpholine, piperidine.
Reduction of Propellane Ketones in Solution Aggregates
Natrajan, Anand,Sukenik, Chaim N.
, p. 3559 - 3563 (1988)
The reduction of propellane diones and ketols has been studied in water containing cationic, anionic and zwitterionic surfactants.From the rate and stereochemistry of the reductions done in these media, the binding of neutral substrates and ionic reagents to surfactant aggregates has been probed.Surface interactions of these variously charged aggregates have been studied, and the behavior of aggregates with like charge but different structure (cationic aqueous micells, vesicles, and reverse micelles) has been compared.A picture of charge distribution at the surface of amine oxide zwitterionic micells has emerged.The oriented propellane binding (polymethylene aligned with surfactant tails and fused five-membered rings tangential to the aggregate surface) first proposed for propellanes bound to cationic micelles has been confirmed and extended to cationic vesicles and to amine oxide micelles.
The surface properties of amine oxides with a fluoroether chain
Chen, Qing-Yun,Dai, Longhao,Guo, Yong,Huang, Meiwei,Shen, Qing,Su, Qin,Su, Zhaoben,Wu, Chengying,Zhao, Zhi-Gang
, (2021/06/12)
Persistent organic pollutants (POPs) includes long-chained fluorosurfactants, for instance, perfluorooctanonate (PFOA) and perfluorooctanesulfonate (PFOS). In order to find out alternative fluorosurfactants, we synthesized eight amine oxides with a fluoroether chain. Their surface properties were evaluated and compared with perfluoroalkyl and hydrocarbon analogues. The surface tensions at critical micelle concentration (γcmc) for the eight amine oxides with a fluoroether chain were at a range from 15.5 to 23.0 mN/m, and γcmc of four fluoroether amine oxides were below 17 mN/m comparable to perfluorooctyl analogues (16.4 mN/m) and much lower than perfluorohexyl (20.5 mN/m) and hydrocarbon analogues (24.2 and 24.7 mN/m). The critical micelle concentration (cmc) for the eight amine oxides with a fluoroether chain were 3 to 535 × 10?4 mol/L. The cmc of four fluoroether amine oxides were 3 to 21 × 10?4 mol/L (0.2 to 1.0 g/L) comparable to perfluorooctyl (0.4 g/L) and hydrocarbon analogues (4 and 10 × 10?4 mol/L) and much lower than perfluorohexyl analogue (36.9 g/L). The surface excesses, the limiting molecule areas and the free energies of micellization of amine oxides were calculated. Fluoroether surfactants are promising alternatives for PFOA and PFOS.
A method for preparing an organic amine oxide
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Paragraph 0018, (2019/06/13)
A organic amine oxide preparation method, comprises the following steps: (1) organic amine as the raw material, the organic amine, solvent and the heteropoly acid quaternary ammonium salt catalyst is added to the container, heating (25 - 100 °C); (2) dropping hydrogen peroxide solution, dropping about 1.5 hours, the dropwise insulation reaction; (3) gas chromatographic detection reaction solution, when the organic amine content is reduced to 0.5% when, stopping the reaction, reaction filtering out catalyst, organic phase distillation shall have amine oxide. The invention relates to a method for preparing an organic amine oxide, its production process is simple, low energy consumption, the catalyst can be used repeatedly, can effectively reduce the production cost, and improves the economic benefit.
Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water
Rauchdi, Mariem,Ait Ali, Mustapha,Roucoux, Alain,Denicourt-Nowicki, Audrey
, p. 266 - 273 (2017/12/06)
Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals.
2,2,2-Trifluoroacetophenone as an organocatalyst for the oxidation of tertiary amines and azines to N-oxides
Limnios, Dimitris,Kokotos, Christoforos G.
supporting information, p. 559 - 563 (2014/04/03)
A cheap, mild and environmentally friendly oxidation of tertiary amines and azines to the corresponding Noxides is reported by using polyfluoroalkyl ketones as efficient organocatalysts. 2,2,2-Trifluoroacetophenone was identified as the optimum catalyst for the oxidation of aliphatic tertiary amines and azines. This oxidation is chemoselective and proceeds in high-to-quantitative yields utilizing 10 mol% of the catalyst and H2O2 as the oxidant.
PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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Page/Page column 25-26, (2009/04/25)
The present invention relates to a process for producing a tertiary amine in the presence of a catalyst containing copper and at least one element selected from the group consisting of elements belonging to Groups 2, 3, 7 and 12 of the Periodic Table (long form of the periodic table), said process including the steps of (a) reducing an amide compound in a hydrogen atmosphere; and (b) introducing a dialkyl amine containing a linear or branched alkyl group having 1 to 6 carbon atoms into a reaction product obtained in the step (a), and treating the reaction product with the dialkyl amine. The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by reducing aliphatic acid amides under moderate conditions using a chromium-free catalyst, as well as a process for producing amine derivatives such as amine oxide by using the aliphatic tertiary amines, with a good productivity in an economical manner.
