- Improvement of the phase-transfer catalysis method for synthesis of glycidyl ether
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A convenient procedure for the synthesis of aliphatic alkylglycidyl ether has been studied. It has been found that the improved preparation of the alkylglycidyl ether can be achieved by using fatty alcohol such as octanol and octadecanol with epichlorohydrin in the presence of phase-transfer catalyst (PTC) such as 1-alkyloxypropan-2-ol-3-trimethyl ammonium methylsulfate, 1-alkyloxypropan-2-ol-3-methyldiethanolammonium methylsulfate, alkyloxy-2-hydroxypropyldimethylamine and alkyloxy-2-hydroxypropyldiethanolamine, tetrabutylammonium bromide, etc. without water and other organic solvents. This method, carried out in solid phase/organic phase (reactants and product themselves), has the following merits: (i) producing the solid by-products such as sodium chloride and sodium hydroxide which are easily removed by simple filtration, (ii) saving the amount of reactants used such as sodium chloride and phase-transfer catalyst, and (iii) increasing the yields of glycidyl ethers. The yields of octylglycidyl ether and octadecylglycidyl ether are 92.0 and 91.7%, respectively. The amount of sodium hydroxide used can be saved by from 1.5 to 0.7 molar ratio with respect to octanol in comparison with those in the conventional method using PTC.
- Kang,Byung Min Lee,Yoon,Yoon
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Read Online
- Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate
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The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.
- Fujitani, Tadahiro,Hong, Dachao,Ito, Satoru,Ji, Xinyi,Kon, Yoshihiro,Nakashima, Takuya,Osuga, Ryota,Sato, Kazuhiko,Yokoi, Toshiyuki
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supporting information
(2020/04/15)
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- NOVEL LOW MOLECULAR WEIGHT CATIONIC LIPIDS FOR OLIGONUCLEOTIDE DELIVERY
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The instant invention provides for novel cationic lipids that can be used in combination with other lipid components such as cholesterol and PEG-lipids to form lipid nanoparticles with oligonucleotides. It is an object of the instant invention to provide
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Paragraph 0099
(2015/11/27)
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- Chemo-enzymatic synthesis and antimicrobial evaluation of alkyloxy propanol amine-based cationic ether lipids
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The present study involved the synthesis and antimicrobial evaluation of alkyloxy propanol amine-based cationic lipids N,N-dimethyl-1-octadecylamino-3- alkyloxy-2-propanol (series A, 7a-e) and N-methyl-N,N-di-(2-hydroxy-3-alkyloxy-2 propyl) octadecylamine (series B, 9a-e) and their acetylated derivatives (8a-e and 10a-e). A simple three-step chemo-enzymatic approach was employed for the synthesis of 7a-e and 9a-e in 71-80 and 67-88 % yields, respectively. The first step involved the synthesis of a series of glycidyl ethers from a series of alcohols (C4, C8, C10, C12, C 14) which were opened in the second step with octadecylamine to obtain 1-octadecylamino-3-alkyloxy-2 propanol (5a-e) and N,N-di-(2-hydroxy-3- alkyloxypropyl) octadecylamine (6a-e). In the third step, alkyloxy propanolamines (5a-e, 6a-e) were quaternized using methyl iodide to yield quaternized ammonium salts. The quaternized ammonium salts were enzymatically acetylated using Candida antarctica lipase-B based immobilized enzyme Novozym 435 to obtain their acetylated derivatives. The quaternized salts as well as their acetylated derivatives were evaluated for antibacterial and antifungal properties. The title compounds were found to possess moderate to good antibacterial activities against all the studied bacterial strains namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Klebsiella aerogenes compared to streptomycin and cetyl trimethyl ammonium bromide (CTAB). The title compounds exhibited relatively good antifungal activities against Candida albicans and no significant activities against other fungal strains namely, Saccharomyces cerevisiae, Rhizopus oryzae and Aspergillus niger when compared to amphotericin B and CTAB.
- Reddy,Rao,Karuna,Kumar,Murthy,Prasad
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p. 437 - 448
(2013/07/27)
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- LIPID COMPOUNDS FOR SUPRESSION OF TUMORIGENESIS
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The present invention provides compounds, or pharmaceutically acceptable salts or analogs thereof, which exhibit anti-tumor activity. The present invention also includes methods for inhibiting the growth of cancer cells by contacting an effective amount of a compound of the present invention with the cancer cells in vitro or in vivo.
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Page/Page column 33-34
(2010/04/03)
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- Preparation and properties of phosphate surfactants containing ether and hydroxy groups
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Phosphate surfactants containing ether and hydroxyl groups were prepared by a simple reaction between the corresponding epoxide and the diethyl phosphate. The relationships between the structure and colloidal properties were evaluated in terms of the critical micelle concentration (CMC), γCMC, foaming ability, and water absorbing and holding abilities. Based on these results, it was concluded that the ether and hydroxy groups synergistically worked together to decrease the CMC and increase the foaming ability. The degree of neutralization remarkably affected the colloidal properties. The highly neutralized states showed a more positive effect on water holding power but an opposite effect on the foaming ability. Copyright
- Osanai, Shuichi,Yamada, Go,Hidano, Ruri,Beppu, Koji,Namiwa, Kimiyoshi
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experimental part
p. 41 - 49
(2011/12/05)
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- Influence of substructures on the spreading ability and hydrolysis resistance of double-tail trisiloxane surfactants
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Four types of novel double-tail trisiloxane surfactants of the general formula Me3SiOSiMeR1 OSiMe3 (R1 = -(CH2)3NR2 CH2CH(OH)CH 2(OCH2CH2)xOCH3; R 2 = -CH2CH(OH)CH2OCH2 (CH 2)yCH3, -CH2 (CH2) 3CH3, -CH2CH2CH(CH3) 2; x = 8.4, 12.9, 17.5, 22; y = 2, 6), have been synthesized. Their structures were characterized by proton and carbon nuclear magnetic resonance. Most of them are able to reduce the surface tension of water to less than 24 mN/m at concentration levels of 10-5 mol/L and 10-4 mol/L. The emphasis was on the influence of substructures on their spreading ability and hydrolysis resistance. The results showed that a weaker hydrophilicity of a surfactant molecule, a larger molar ratio of methyl to methylene in the whole hydrophobic groups, more flexible hydrophobic groups and introduction of a methyl group in the spacer can all improve the spreading ability of the double-tail trisiloxane surfactant solutions on low-energy solid surfaces. The double-tail trisiloxane surfactants 1F and 2F are stable for more than 270 days in a neutral environment (pH 7.0). The hydrolysis resistance of the double-tail trisiloxane surfactants can be improved by a weaker hydrophilicity of the surfactant molecule, and a larger volume of the hydrophobic groups. Copyright
- Peng, Zhongli,Lu, Caifeng,Xu, Minling
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scheme or table
p. 75 - 81
(2012/01/05)
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- NOVEL ALKYLOXY-ETHERS AND ALKOXYLATES THEREOF
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Novel 1,3-dialkyloxy-2-propanol and alkoxylates thereof may be prepared in good yield by a convenient process comprising adding epichlorohydrin to a stoichiometric excess of alcohol, wherein the ratio of alcohol:epichlorohydrin is at least about 3:1, preferably in the presence of a Group 1 A metal hydroxide and a phase transfer catalyst. The result shows excellent selectivity of to the 1,3- substitution positions, and the alkyl chain may be saturated or unsaturated and may contain one or more heteroatoms. The alkoxylates may include repeating alkoxy units in the 2-position. The compositions are useful as surfactants, diluents, and the like.
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Page/Page column 9-10
(2008/12/08)
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- Process for producing glyceryl ether
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A process for producing a glyceryl ether which contains a markedly small amount of organohalogen compounds and therefore can be used even for cosmetics and body detergents. The process comprises reacting an alcohol with an α-epihalohydrin in the presence of an acid catalyst, subjecting the reaction mixture to ring closure to convert it into the corresponding glycidyl ether and then hydrolyzing the glycidyl ether, wherein: (a) the hydrolysis is effected at 140 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound, or (b) the reaction mixture after the hydrolysis is heated at 100 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound.
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- Process for preparing alcohol derivatives
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The present invention provides a process for preparing an alcohol derivative, where the alcohol derivative is an ester, acetal, ketal, ether glycoside, or alkyl glycoside, by reacting an alcohol with a carbonyl compound, alcohol, olefin, epoxy compound or saccharide, where C2-4 vicinal alkylene oxides are excluded, in the presence of (A) an aluminum alkoxide and (B) sulfuric acid or phosphoric acid.
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- Method of synthesizing glycidyl ether compounds in the absence of water and organic solvents
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The present invention relates to a method of synthesizing glycidyl ether compounds without the addition of solvent. In particular, the present invention provides the improved preparation of the glycidyl ethers by using fatty alcohols with epichlorohydrin in the presence of alkali metal hydroxide and phase-transfer catalysts in the appropriate molar ratios of them without water and organic solvents.
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- Aluminum compounds and use thereof
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An aluminum compounds represented by the following general formula (1): Al(R1—SO3)1(R2)m(R3)n??(1) wherein R1is a hydrocarbon group which may be substituted, R2is a hydrocarbon group which may be substituted, an aliphatic hydrocarbonoxy group which may be substituted, or a halogen atom, R3is an aromatic hydrocarbonoxy group which may be substituted, and 1, m and n are independently a number of 0 to 3, with the proviso that 1+m+n equals 3, and 1 is not 0, an acid catalyst comprising the aluminum compound, and a process for producing an ester, acetal, ketal, ether or alkyl glycoside making use of the catalyst. The catalyst is suitable for use in a variety of acid-catalyzed reactions of alcohols, i.e., reactions with carbonyl compounds, such as esterification, transesterification, acetalization and ketalization, etherification, ring-opening reactions of epoxy compounds, etc. in addition to the above-described respective reactions, is not deactivated by alcoholysis, has a sufficient activity, can easily control a reaction catalyzed thereby and scarcely causes side reactions. Consequently, the use of the catalyst permits the production of the intended product at a high yield from starting materials used in an almost equimolar proportion.
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- A Halide-Free Method for Olefin Epoxidation with 30% Hydrogen Peroxide
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A catalytic system consisting of sodium tungstate dihydrate, (aminomethyl) phosphonic acid, and methyltrioctylammonium Hydrogensulfate, effects the epoxidation of olefins using 30% hydrogen peroxide with a substrate-to-catalyst molar ratio of 50 - 500. The reaction proceeds in high yield without solvents, or, alternatively, with added toluene under entirely halide-free conditions. Lipophilic ammonium hydrogensulfate, which replaces the conventional chloride, and an (α-aminoalkyl)phosphonic acid are crucial for the high reactivity. This method is operationally simple, environmentally benign, and much more economical than the oxidation with m-chloroperbenzoic acid, allowing for a large-scale preparation of epoxides. Various substrates including terminal olefins, 1,1- and 1,2-disubstituted olefins, cyclic olefins, and tri- and tetrasubstituted olefins as well as allylic alcohols, esters, α,β-unsaturated ketones, and ethers can be epoxidized in high yield. The scope and limitations of this new reaction system are discussed.
- Sato, Kazuhiko,Aoki, Masao,Ogawa, Masami,Hashimoto, Tadashi,Panyella, David,Noyori, Ryoji
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p. 905 - 915
(2007/10/03)
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- Synthesis of alkyloxy (di)alkylamino propanols, hydroxy alkyloxy (di)alkylamino propanols, and the dimer compounds for use as fuel additives
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Alkyl glycidyl ethers and bis glycidyl ethers, synthesized in a heterogeneous weakly hydrous medium, were condensed with primary or secondary amines to obtain 3-alkyloxy propanolaminesor bis alkyloxy propanolamines in a regioselective manner. The compounds were characterized by conventional spectroscopic methods, and complete nuclear magnetic resonance data are given. Their high-temperature stability, their good emulsifying power, their oxidation, and corrosion inhibition make these compounds suitable for solubilizing ethanol-diesel fuel blends.
- Satge De Caro, Pascale,Mouloungui, Zephirin,Gaset, Antoine
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p. 235 - 240
(2007/10/03)
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- Single step etherification of fatty alcohols by an epihalohydrin
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A new, single step synthesis of glycidyl ethers from an epihalohydrin (X = Cl, Br) and seven fatty alcohols is proposed in a poorly hydrated solid/liquid heterogeneous basic medium. The selectivity and the yields of the reaction are high. The structural analysis and the physicochemical characteristics of the synthesized products are reported.
- Najem,Borredon
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p. 3021 - 3030
(2007/10/02)
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- Liquid-Liquid-Extraction of Metal Ions with Lariat Ethers
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Lariat ethers of various ring size and substitution are synthesized and characterized by physical data and chemical analysis.The extraction behaviour of the crown compounds towards Na+, K+, Cs+ and Ag+ in a picric acid solution has been investigated.The extraction constants for 1:1 and 1:2 complexes are determined using the equilibrium distribution data.The results show that the flexible side chain in the investigated compounds has in no case a positive effect on the metal picrate extraction.
- Gloe, K.,Muehl, P.,Beger, J.,Poeschmann, C.,Petrich, M.,Beyer, L.
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p. 413 - 421
(2007/10/02)
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