- Preparation of Stable Single-Compartment Vesicles with Cationic and Zwitterionic Amphiphiles Involving Amino Acid Residues
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Cationic and zwitterionic amphiphiles involving amino acid residues were synthesized as modifications of the phospholipids.Their aggregated structures in both dilute aqueous dispersion and solution were investigated by electron microscopy.Amphiphiles involving an alanine residue or a sarcosine residue, N,N-didodecyl-Nα--L-alaninamide bromide (N+C5Ala2C12), N,N-didodecyl-Nα-hexanoyl>-L-alaninamide bromide (CAC2N+C5Ala2C12), N,N-didodecyl-Nα-sarcosinamide bromide (N+C5Sar2C12), and N,N-didodecyl-Nα-hexanoyl>sarcosinamide bromide (CAC2N+C5Sar2C12), readily form well-developed multiwalled bilayer assemblies (lamellae and vesicles) and stable single-walled vesicles without any additives in dilute aqueous dispersion and sonicated aqueous solution, respectively.On the other hand, those involving one or three leucine residues, N,N-didodecyl-Nα--L-leucinamide bromide (N+C5Leu2C12), N,N-didodecyl-Nα-hexanoyl>-L-leucinamide bromide (CAC2N+C5Leu2C12), and N,N-didodecyl-Nα-α'-α''--L-leucyl>-L-leucyl>-L-leucinamide bromide (N+C5Leu32C12), form partly developed multiwalled bilayer assemblies in aqueous dispersion while stable single- or double-walled vesicles are observable in sonicated aqueous solution.The significance of the tripartite structure in amphiphile assemblies for the formation of stable single-walled bilayer vesicles has been discussed.
- Murakami, Yukito,Nakano, Akio,Ikeda, Hidetsugu
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Read Online
- Serum Compatible Spermine-Based Cationic Lipids with Nonidentical Hydrocarbon Tails Mediate High Transfection Efficiency
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Cationic lipids are widely used as nonviral synthetic vectors for gene delivery as a safer alternative to viral vectors. In this work, a library of L-shaped spermine-based cationic lipids with identical and nonidentical hydrophobic chains having variable carbon lengths (from C10 to C18) was designed and synthesized. These lipids were characterized and the structure-activity relationships of these compounds were determined for DNA binding and transfection ability when formulated as cationic liposomes. The liposomes were then used successfully for the transfection of HEK293T, HeLa, PC3, H460, HepG2, SH-SY5Y and Calu’3 cell lines. The transfection efficiency of lipids with nonidentical hydrocarbon chains was greater than the identical analogue. These reagents exhibited superior efficiency to the commercial reagent, Lipofectamine3000, under both serum-free and 10–40 % serum conditions in HEK293T, HeLa and H460 cell lines. The lipids were not toxic to the tested cell line. The results suggest that L-shaped spermine-based cationic lipids with nonidentical hydrocarbon tails could serve as efficient and safe nonviral vector gene carriers in further in vivo studies.
- Thongbamrer, Chopaka,Roobsoong, Wanlapa,Sattabongkot, Jetsumon,Opanasopit, Praneet,Yingyongnarongkul, Boon-ek
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- MATERIALS COMPRISING CARBON-EMBEDDED COBALT NANOPARTICLES, PROCESSES FOR THEIR MANUFACTURE, AND USE AS HETEROGENEOUS CATALYSTS
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The present invention relates to catalytically active material, comprising grains of non-graphitizing carbon with cobalt nanoparticles dispersed therein, wherein dP, the average diameter of cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 1 nm to 20 nm, D, the average distance between cobalt nanoparticles in the non-graphitizing carbon grains, is in the range of 2 nm to 150 nm, and ω, the combined total mass fraction of metal in the non-graphitizing carbon grains, is in the range of 30 wt% to 70 wt% of the total mass of the non-graphitizing carbon grains, and wherein dP, D and ω conform to the following relation: 4.5 dP / ω > D ≥ 0.25 dP / ω. The present invention, further, relates to a process for the manufacture of material according to the invention, as well as its use as a catalyst.
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Page/Page column 17; 19
(2021/03/13)
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- One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
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The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
- Coeck, Robin,De Vos, Dirk E.
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supporting information
p. 5105 - 5114
(2020/08/25)
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- Sustainable hydrogenation of aliphatic acyclic primary amides to primary amines with recyclable heterogeneous ruthenium-tungsten catalysts
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The hydrogenation of amides is a straightforward method to produce (possibly bio-based) amines. However current amide hydrogenation catalysts have only been validated in a rather limited range of toxic solvents and the hydrogenation of aliphatic (acyclic) primary amides has rarely been investigated. Here, we report the use of a new and relatively cheap ruthenium-tungsten bimetallic catalyst in the green and benign solvent cyclopentyl methyl ether (CPME). Besides the effect of the Lewis acid promotor, NH3 partial pressure is identified as the key parameter leading to high primary amine yields. In our model reaction with hexanamide, yields of up to 83% hexylamine could be achieved. Beside the NH3 partial pressure, we investigated the effect of the catalyst support, PGM-Lewis acid ratio, H2 pressure, temperature, solvent tolerance and product stability. Finally, the catalyst was characterized and proven to be very stable and highly suitable for the hydrogenation of a broad range of amides.
- Coeck, Robin,Berden, Sarah,De Vos, Dirk E.
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supporting information
p. 5326 - 5335
(2019/10/11)
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- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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- Conversion of Primary Amines to Symmetrical Secondary and Tertiary Amines using a Co-Rh Heterobimetallic Nanocatalyst
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Symmetrical tertiary amines have been efficiently realized from amine and secondary amines via deaminated homocoupling with heterogeneous bimetallic Co2Rh2/C as catalyst (molar ratio Co:Rh=2:2). Unsymmetric secondary anilines were produced from the reaction of anilines with symmetric tertiary amines. The Co2Rh2/C catalyst exhibited very high catalytic activity towards a wide range of amines and could be conveniently recycled ten times without considerable leaching. (Figure presented.).
- Chung, Hyunho,Han, Seulgi,Chung, Young Keun,Park, Ji Hoon
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supporting information
p. 1267 - 1272
(2018/02/12)
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- ANIONIC-CATIONIC-NONIONIC SURFACTANT,PRODUCTION AND USE THEREOF
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This invention relates to an anionic-cationic-nonionic surfactant as substantially represented by the formula (I), production and use thereof in tertiary oil recovery. The anionic-cationic-nonionic surfactant of this invention exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced. In the formula (I), each group is as defined in the specification.
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Paragraph 0268
(2017/11/16)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 77
(2016/05/02)
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- Development of new estradiol-cationic lipid hybrids: Ten-carbon twin chain cationic lipid is a more suitable partner for estradiol to elicit better anticancer activity
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The present study illustrates the synthesis and anticancer evaluation of six, ten, twelve and fourteen carbon chain containing cationic lipidated-estradiol hybrids. Previously, we have established the lipidation strategy to introduce anticancer activities in various pharmacophores including estradiol (ES). In this structure activity study the length of the carbon chain is narrowed down between C6-C14 to screen out the most potent anticancer molecule among the class. Among the newly developed ES-cationic lipid conjugates, ten-carbon chain containing derivative, ES-C10 (5c) exhibited 4-12 folds better anticancer activity than the previously established derivative, ES-C8 (5b) in various cancer cells of different origin. Moreover cytotoxicity of this molecule was not observed in non-cancer cells. Notably, in spite of bearing estrogenic moiety, ES-C10 exhibited anticancer activity irrespective of estrogen receptor (ER) expression status. ES-C10 exhibited prominent sub-G0 arrest of cancer cells with concomitant induction of apoptosis and demonstrated significant inhibition of tumor growth in mouse melanoma model. Collectively, ES-C10 exemplifies the development of an anticancer agent with broader activity against cancer cells of different origins.
- Sudhakar, Godeshala,Bathula, Surendar Reddy,Banerjee, Rajkumar
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p. 653 - 663
(2015/01/16)
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- METHOD FOR PRODUCING N-SUBSTITUTED AMINE COMPOUNDS THROUGH CATALYZED ALKYLATION
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The invention relates to a method for producing a N-substituted amine compound by catalyzed alkylation. The method uses amine and alcohol or two kinds of amines as the reaction materials, employs composite metal oxides catalyst at a reaction temperature of 80-180° C. to catalyze the reaction for 6-36 hours, so as to produce the N-substituted amine compound. The reaction condition of the method of the invention is relatively moderate, using a catalyst made of cheap non-noble metals, which is non-caustic and easy to be separated and reused. The reaction does not need any medium and has relatively high conversion rate and selectivity.
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Paragraph 0046
(2014/02/16)
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- Unexpected selectivity in ruthenium-catalyzed hydrosilylation of primary amides: Synthesis of secondary amines
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Selective ruthenium-catalyzed reductive coupling of primary amides under hydrosilylation conditions is achieved using an one pot procedure. Using 3 equiv. of phenylsilane and [RuCl2(mesitylene)]2 (1-2 mol%) as the catalyst at 100 °C under neat conditions, secondary symmetric amines were obtained in good yields and with high chemoselectivities. The Royal Society of Chemistry 2013.
- Li, Bin,Sortais, Jean-Baptiste,Darcel, Christophe
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supporting information
p. 3691 - 3693
(2013/05/21)
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- Heterogeneously catalyzed self-condensation of primary amines to secondary amines by supported copper catalysts
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Self-condensation of primary amines to symmetrically substituted secondary amines could efficiently be promoted by an inexpensive supported copper catalyst, Cu/Al2O3, easily prepared by the reduction of the hydroxide precursor, Cu(OH)x/Al2O3. Various kinds of structurally diverse primary amines including benzylamine, picolylamine, and aliphatic amine derivatives could selectively be converted into the corresponding secondary amines in moderate to excellent yields without any cocatalysts such as bases and stabilizing ligands in 1 atm of Ar or H 2. The reactions in H2 showed higher selectivities to desired secondary amines than those in Ar. The roles of H2 are the promotion of hydrogenation of N-alkylimines and the stabilization of active Cu(0) species. In addition, in the presence of Cu/Al2O3, unsymmetrically substituted secondary amines could efficiently be synthesized by N-alkylation of primary amines with alcohols and reductive amination of aldehydes. The observed catalysis was truly heterogeneous, and the retrieved Cu/Al2O3 catalyst could be reused for self-condensation without a significant loss of its catalytic performance. The reaction mechanism involving dehydrogenation of primary amines and condensation to N-alkylimines followed by hydrogenation, the so-called "borrowing hydrogen pathway", has been proposed. The Royal Society of Chemistry 2013.
- Kim, Insu,Itagaki, Shintaro,Jin, Xiongjie,Yamaguchi, Kazuya,Mizuno, Noritaka
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p. 2397 - 2403
(2013/09/02)
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- Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system
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The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac)3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained.
- Pehlivan, Leyla,Métay, Estelle,Laval, Stéphane,Dayoub, Wissam,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
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scheme or table
p. 1971 - 1976
(2011/04/22)
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- Surface properties of Ni/MgO catalysts for the hydrogenation of lauronitrile
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60%Ni/MgO (wt%) catalysts were prepared by the co-precipitation method and the influence of n-butanol treatment was investigated. The results showed that the treatment with n-butanol improved the dispersion and reducibility of supported nickel, resulted in an increase of H2 uptake from 410 to 582 μmol/g, corresponding to an increase of active Ni surface area from 32 to 46 m2/g (increased by 42%). Accordingly, the catalytic activity for the hydrogenation of toluene to methyl cyclohexane was significantly increased. Microcalorimetric adsorption of H2 and CO indicated that the treatment with n-butanol increased the amount of active metal sites on the surface, without the change of electron densities of supported nickel surface. Microcalorimetric adsorption of CO2 and NH3 revealed the strong surface basicity and weak surface acidity for the Ni/MgO catalysts, especially for the reduced ones. The initial heat for the adsorption of acetonitrile was measured to be about 130 kJ/mol on the Ni/MgO catalysts, indicating the strong interaction between acetonitrile and the supported nickel, which might be an important factor determining the activity of nickel for the hydrogenation of aliphatic nitriles. The surface basicity of the Ni/MgO catalysts might play a role in inhibiting the formation of secondary and tertiary amines and therefore improved the selectivity to primary amine during the hydrogenation of lauronitrile to laurylamine. In addition, the Ni/MgO-B catalyst prepared with n-butanol treatment seemed more active for the hydrogenation of lauronitrile.
- Chen, Hui,Xue, Mingwei,Shen, Jianyi
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experimental part
p. 246 - 255
(2010/08/04)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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The present invention relates to a process for producing an aliphatic amine, comprising the step of contacting a linear or branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms with ammonia and hydrogen in the presence of a catalyst formed by supporting at least (A) a ruthenium component produced by hydrolysis of a ruthenium compound on a carrier, or by further supporting, in addition to the component (A), a specific second metal component or a specific third metal component on the carrier. According to the process of the present invention, an aliphatic primary amine can be produced from an aliphatic alcohol with a high catalytic activity and a high selectivity.
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Page/Page column 12
(2008/06/13)
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- Anchor dependency for non-glycerol based cationic lipofectins: Mixed bag of regular and anomalous transfection profiles
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Although detailed structure-activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure-activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1-15) of recently reported non-glycerol based monocationic transfection lipids. The C14 analogues in both series 1 (lipids 1-6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C10 and C14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure-activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane re-organizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1-15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37°C).
- Singh, Rajkumar Sunil,Mukherjee, Koushik,Banerjee, Rajkumar,Chaudhuri, Arabinda,Hait, Samik Kumar,Moulik, Satya Priya,Ramadas, Yerramsetti,Vijayalakshmi, Amash,Rao, Nalam Madhusudhana
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p. 900 - 909
(2007/10/03)
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- Reaction of aliphatic amines with 49% formic acid. 1-hexylamine, di-1-hexylamine, N,N-dimethyl-1-hexylamine, 1-dodecylamine, N,N-dimethyl-1-dodecylamine and N,N-dimethyl-1-butylamine
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Two primary amines, 1-hexylamine 2, 1-dodecylamine 19, one secondary amine, di-1-hexylamine 18, and three tertiary amines, N,N-dimethyl-1-hexylamine 6, N,N-dimethyl-1-butylamine 3, and N,N-dimethyl-1-dodecylamine 22 were each heated at 150°C, 250°C or 350°C with 49% aqueous formic acid for varying periods of time. The aliphatic primary amines underwent easy N-formylation and subsequent reduction to give N-methyl- and N,N-dimethylalkylamines. Especially at higher temperatures, other reactions intervened including elimination of NH3 to the corresponding alkenes followed by partial double bond isomerization. Tertiary amines were more reactive at higher temperatures undergoing hydrolysis and reductive cleavages to secondary and primary amines, which subsequently followed the reaction sequences seen for primary amines. This series of saturated amines showed none of the cleavage into smaller fragments that was observed in the reductive alkylation of pyridine and 4-methylpyridine to a series of N-alkylpiperdines. This result reinforces the bis-aza-retro-Aldol-fragmentation mechanism postulated for the formation of the N-alkylpiperidines. Johann Ambrosius Barth 1997.
- Katritzky, Alan R.,Parris, Roslyn L.,Ignatchenko, Elena S.,Allin, Steven M.,Siskin, Michael
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- Surface-active properties of novel cationic surfactants with two alkyl chains and two ammonio groups
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A series of bis-quaternary ammonium salts was easily prepared by the reaction of a long-chain tert-alkylamine with epichlorohydrin, and their surface-active properties were measured. The prepared amphipathic compounds had good water solubility and showed characteristic surface-active properties, particularly, extremely excellent foaming ability and foam stability for some specific compounds, such as the compound with a dodecyl and a tetradecyl group as the lipophilic chains. Their critical micelle concentration, which decreased with increased alkyl chainlength, is two orders of magnitude lower compared with the conventional mono-quaternary ammonium salts. In comparison with surface-active properties of bis-quaternary ammonium salts, prepared from various organic dichlorides, there are little differences based on the kind of connecting group in the surface-active properties except for foaming. Copyright
- Kim, Tae-Seong,Kida, Toshiyuki,Nakatsuji, Yohji,Hirao, Toshikazu,Ikeda, Isao
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p. 907 - 911
(2007/10/03)
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- Selectivity control in substituted fatty amines synthesis from esters or nitriles in the presence of bifunctional catalysts
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Copper chromite-type catalysts, supported by alumina or graphite and promoted with barium, were used for the one-step synthesis of tertiary fatty amines [R2NCH3 or RN(CH3)2] from ester, acid or nitrile and ammonia, methanol and hydrogen. The surface composition of the catalysts, studied by X-ray photoelectron spectroscopy and by adsorption experiments, showed that there was a correlation between selectivity and the presence of a well-dispersed CuCrO2 phase, stabilized with barium. Moreover, the elements influencing the stability of the copper catalysts were also studied, and the promoter or/and the support increased the copper surface area and the stability of the catalyst in the presence of water or ammonia.
- Barrault,Brunet,Suppo-Essayem,Piccirilli,Guimon
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p. 1231 - 1238
(2007/10/02)
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- Stereoselective synthesis of cis-4-(substituted) monobactams from ethyl acetoacetate
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The stereoselective synthesis of cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (25) from ethyl acetoacetate is described. Nitrosation of this compound and reduction of the resulting oxime gave the corresponding amine, which after treatment with different acyl halides, yielded the acylamino derivatives (6)-(8). Condensation with p-anisidine gave the enamines (12)-(14), which were then reduced to the β-amino acid esters (15)-(17). Stereoselective cyclization with Grignard reagents as base, and appropriate deprotection and sulphonation of the resulting β-lactams (18)-(20), led to the title compounds.
- Fernandez-Resa, Piedad,Herranz, Rosario,Conde, Santiago,Arribas, Enrique
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- SELECTIVE CONVERSION OF PRIMARY AMINES INRO N,N-DIMETHYLALKYL- OR N,N-DIALKYLMETHYL-AMINES WITH METHANOL AND RuCl2(Ph3P)3
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N,N-dimethylalkyl- or N,N-dialkylmethyl-amines are selectively obtained from the reaction between aliphatic amines and methanol at 180 deg C for 7 h in the presence of RuCl2(Ph3P)3 catalyst.
- Arcelli, Antonio,Khai, Bui-The,Porzi, Gianni
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- ACTIVITY AND SELECTIVITY OF COBALT, NICKEL AND COPPER CATALYSTS FOR HYDROGENATION OF LAURONITRILE
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Cobalt and nickel metal powders possessing various specific surface areas were prepared by decomposition of their salts under hydrogen.The activity of the metals for hydrogenation of lauronitrile was found to be proportional to their specific surface areas.Oxide carriers do not affect the specific activity of the metals.The relative specific activities of the metals are in the ratio Ni:Co:Cu=20:10:1.Pure nickel affords 2.3 times more secondary amine than cobalt; on copper catalyst, secondary amine is formed predominantly.
- Pasek, Josef,Kostova, Nina,Dvorak, Bohumir
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p. 1011 - 1022
(2007/10/02)
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- Cyclization of α,ω Aliphatic Diamines and Conversion of Primary Amines to Symmetrical Tertiary Amines by a Homogeneous Ruthenium Catalyst
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α,ω Aliphatic diamines were cyclized to heterocyclic amines by being heated at 180 deg C for 5 h with RuCl2(Ph3P)3 in diphenyl ether.Primary amines having an α-hydrogen atom are converted to symmetrical tertiary amines by being heated at 185 or 235 deg C for 8 h with RuCl3*3H2O and Ph3P in THF solution.
- Bui-The-Khai,Concilio, Carlo,Porzi, Gianni
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p. 1759 - 1760
(2007/10/02)
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- A FACILE SYNTHESIS OF SYMMETRICAL SECONDARY AMINES FROM PRIMARY AMINES PROMOTED BY THE HOMOGENEOUS CATALYST RuCl2(Ph3P)3
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Primary amines bearing an α-hydrogen atom are quantitatively converted to symmetrical secondary amines by heating at 185 deg C for 5 h in the presence of a catalytic amount of RuCl2(Ph3)3.
- Bui-The-Khai,Concilio, Carlo,Porzi, Gianni
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p. 249 - 251
(2007/10/02)
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