- Synthesis and properties of biodegradable cationic gemini surfactants with diester and flexible spacers
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A series of cationic gemini surfactants with diester and flexible spacers, namely C12-PG-C12, C14-PG-C14 and C16-PG-C16, were synthesized, purified and characterized. The surface properties and aggregation behavior of the gemini surfactants were investigated by surface tension, electrical conductivity, fluorescence and Krafft point. These gemini surfactants possess higher surface activity than the traditional monomeric surfactants. The thermodynamic parameters exhibited that the micellization was a spontaneous and exothermic process in environment. The micellization process became less favorable with the decrease of alkyl chain length and the increase of temperature. Steady-state fluorescence measurements revealed that the micropolarity and aggregation number of micelles decreased with the increase of hydrocarbon chain length. The Krafft points were taken as ?0?°C, which indicated the synthesized gemini surfactants had good water solubility. The biodegradability of the gemini surfactants were evaluated in river water using Closed Bottle tested and showed their high biodegradation ratio in the open environment due to the diester bond inserting in the flexible spacer of surfactant molecules.
- Xu, Dongqing,Ni, Xiaoyue,Zhang, Congyu,Mao, Jie,Song, Changchun
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Read Online
- Micellization of cationic gemini surfactants with various counterions and their interaction with DNA in aqueous solution
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The micellization of six cationic gemini surfactants with various counterions, [C12H25(CH3)2N(CH 2)6N(CH3)2C12H 25]X2, designated as C12C6C 12X2 with X = F-, Cl-, Br -, Ac-, NO3-, and 1/2SO 42- in aqueous solutions has been investigated by isothermal titration microcalorimetry (ITC) and conductivity measurements. The interaction of these surfactants with DNA in aqueous solutions has also been investigated by isothermal titration microcalorimetry. The critical micelle concentration (CMC) and the degree of micellar ionization (?±), the critical aggregation concentration (CAC), the saturation concentration (C 2) of the aggregation, and the associated thermodynamic parameters were determined. The nature of the counterion significantly affects the processes of both micellization and aggregation. The trends for aggregation basically follow the Hofmeister (lyotropic) series, but the pattern of the variation of the enthalpy of aggregation often revealed a more complex behavior. Among the counterions examined, SO42- is the most effective anion for decreasing the CMC (or CAC). Both aggregation processes are mainly entropy-driven since the values of the entropy changes multiplied by temperature are much larger than the absolute values of the enthalpy changes. The binding of micelles to DNA is strongly dominated by the positive entropy gain on release of the small counterions from the micelles and from DNA. The interaction of all of the surfactants with DNA was dependent on the DNA concentration and may be associated with each micelle interacting with more than one DNA molecule.
- Jiang, Nan,Li, Peixun,Wang, Yilin,Wang, Jinben,Haike, Yan,Thomas, Robert K.
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- Chemical synthesis of silver nanowires using N,N-dimethyldodecylamine oxide
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This paper describes a new approach for the synthesis of uniform silver nanowires (AgNWs) using zwitterionic amphiphile, N,N-dimethyldodecylamine oxide (DDAO). Heating of AgCl and DDAO in the presence of silver nanoparticles at 135°C for 3 h produces longer AgNWs. The DDAO serves as a source of both a reducing and capping agent in the process.
- Matsune, Hideki,Kuramitsu, Yudai,Takenaka, Sakae,Kishida, Masahiro
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Read Online
- Modeling of the hydrophobic microenvironment of water-soluble molybdoenzymes in an aqueous micellar solution
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A toluene-soluble molybdenum(vi) complex containing a bulky hydrophobic substituent, (Et4N)2[MoVIO2{1,2-S2-3,6-(RCONH)2C6H2}2] (R = (4-tBuC6H4)3C), was dissolved in the hydrophobic core of a micelle in an aqueous medium and catalyzed the biomimetic reduction of an amine N-oxide by an NADH analog. The kinetic isotope effect of solvent water clearly indicates that water molecules are essential for catalysis and are involved in the rate-determining step.
- Hasenaka, Yuki,Okamura, Taka-Aki,Onitsuka, Kiyotaka
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Read Online
- Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis
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The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.
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Paragraph 0048-0056; 0058
(2021/03/13)
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- PROCESS FOR CONVERTING AMIDE TO AMINE
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Provided is a process for converting an amide into an amine comprising hydrogenation of the amide at a temperature not higher than 130°C and a hydrogen pressure not higher than 50 bar in the presence of a supported heterogeneous catalyst preparable by a method comprising depositing vanadium on a supported noble metal catalyst by impregnation.
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Page/Page column 12-22
(2021/06/11)
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- SUPPORTED HETEROGENEOUS CATALYST, PREPARATION AND USE THEREOF
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A supported heterogeneous catalyst comprises rhodium and vanadium on a support, wherein the supported heterogeneous catalyst is preparable by depositing vanadium on a supported rhodium catalyst by impregnation. A process for preparing the aforementioned catalyst and a process for converting an amide into an amine in the presence of the aforementioned catalyst are provided.
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Page/Page column 12-21
(2021/06/11)
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- Efficient hydrogenation of aliphatic amides to amines over vanadium-modified rhodium supported catalyst
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This work presents a highly efficient catalytic hydrogenation system developed for the selective transformation of tertiary N,N-dimethyldodecanamide and secondary azepan-2-one amides to the corresponding amines. Industrial hydrogenation catalysts Pd/Al2O3, Pt/Al2O3 and Rh/Al2O3 were modified with vanadium (V) or molybdenum (Mo) species as oxophilic centres. The modified catalysts were prepared by deposition of V or Mo precursor on supported catalysts via impregnation method. The catalysts were characterized by ICP-OES, XRD, XPS, H2-TPR, FTIR, CO-chemisorption, TEM, SEM-EDX and TGA. Modified Rh-V/Al2O3 catalyst displayed the best performance affording high yield and selectivity >95 % to the desired tertiary and secondary amines at moderate reaction conditions of T H2 0 sites and oxophilic Vδ+ sites in the bimetallic Rh-V/Al2O3 catalyst were determined to be beneficial for the selective dissociation of C[dbnd]O bond of the carboxamides into the desired amines.
- Hernandez, Willinton Y.,Kusema, Bright T.,Pennetier, Alex,Streiff, Stéphane
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- N-Methylation of amines and nitroarenes with methanol using heterogeneous platinum catalysts
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We report herein the selective N-methylation of amines and nitroarenes with methanol under basic conditions using carbon-supported Pt nanoparticles (Pt/C) as a heterogeneous catalyst. This method is widely applicable to four types of N-methylation reactions: (1) N,N-dimethylation of aliphatic amines under N2, (2) N-monomethylation of aliphatic amines under 40 bar H2, (3) N-monomethylation of aromatic amines under N2, and (4) tandem synthesis of N-methyl anilines from nitroarenes and methanol under 2 bar H2. All these reactions under the same catalytic system showed high yields of the corresponding methylamines for a wide range of substrates, high turnover number (TON), and good catalyst reusability. Mechanistic studies suggested that the reaction proceeded via a borrowing hydrogen methodology. Kinetic results combined with density functional theory (DFT) calculations revealed that the high performance of Pt/C was ascribed to the moderate metal–hydrogen bond strength of Pt.
- Jamil, Md.A.R.,Touchy, Abeda S.,Rashed, Md. Nurnobi,Ting, Kah Wei,Siddiki, S.M.A. Hakim,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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- Cationic linear chloramine antibacterial agent and synthesis method thereof
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The invention belongs to the technical field of synthesis and application of chloramine antibacterial agents, and provides a synthesis method of a cationic linear chloramine antibacterial agent. N-tert-butyl-chloroalkylamide II and a compound IV are used as raw materials to prepare a chloramine precursor compound III, then to be reacted with tert-butyl hypochlorite at a room temperature to preparea chloramine compound I; and the compound IV is one of a tertiary amine compound IV1 with different alkyl chains, a pyridine compound IV2 with different alkyl chains and tributyl phosphine. Accordingto the preparation method, when use of potassium cyanide is avoided, different cation structures are introduced into linear chloramine molecules to improve water solubility and improve the antibacterial activity; moreover, the structure of long alkyl chains and the chloramine structure introduced into the cation center can produce the strong synergistic antibacterial effect, and the antibacterialactivity is significantly improved compared with hydantoin like chloramine; and the theoretical basis is hopefully provided for preparation of high-efficiency cationic chloramine antibacterial materials .
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Paragraph 0078-0080
(2019/11/12)
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- End group type macromolecular quaternary ammonium salt and preparation method thereof
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The invention discloses an end group type macromolecular quaternary ammonium salt and a preparation method thereof. Polyhydric alcohols and chlorinated carboxylic acid are dehydrated to produce a macromolecular skeleton in the presence of a catalyst and an appropriate solvent, and the prepared macromolecular skeleton is reacted with tertiary amine so as to obtain the end group type macromolecularquaternary ammonium salt. The macromolecular quaternary ammonium salt is novel in structure and low in toxicity, has strong bacteria inhibiting and resisting effects, and is capable of adjusting the structure according to needs so as to achieve corresponding physical properties. The macromolecular quaternary ammonium salt has wide application prospects in the fields of polymer emulsion, personal care, dry-film preservation, coatings, adhesives, household supplies and the like. The macromolecular quaternary ammonium salt disclosed by the invention is simple and controllable in preparation process, high in operability, mild in conditions, green, environmental-friendly and suitable for industrial production.
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Paragraph 0017
(2019/03/29)
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- COPPER CONTAINING CATALYST FOR PREPARATION OF ALIPHATIC AMINES
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Provided is a process of reacting an aliphatic alcohol with an aminating agent for obtaining an aliphatic amine, wherein the reaction is carried out in a catalyst comprising from 68wt% to 100wt% of a copper oxide and from 0wt% to 0.1wt% of a metal co-catalyst, and optionally from 0wt% to 32wt% of a catalyst support, weight percentage is based on the total weight of the catalyst.
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Paragraph 0045-0046
(2017/12/27)
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- Synthesis, surface activity and thermodynamic properties of cationic gemini surfactants with diester and rigid spacers
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A group of cationic gemini surfactants with diester and rigid spacers, 12-Ph-12, 14-Ph-14, 16-Ph-16, were synthesized and confirmed by IR, 1H NMR and elemental analysis. The surface parameters of the synthesized gemini surfactants including: the critical micelle concentration (CMC), the surface tension value at CMC (γCMC), effectiveness (πCMC), efficiency (pC20), maximum surface excess (Γmax) and minimum surface area (Amin), were obtained from surface tension measurements. These gemini surfactants showed higher surface activity than the traditional monomeric surfactants. The thermodynamic parameters of micellization process from conductivity measurements showed that the micellization was a spontaneous and exothermic process in environment, and the micellization process becomes less favorable with the decrease of alkyl chain length and increase in temperature. The micropolarity was evaluated from steady fluorescence spectra, and the dye solubilization was investigated by using UV–visible spectroscopy. The results revealed that the micropolarity of surfactant micelles is very low and these gemini surfactants can really enhance the solubility of water insoluble dyes.
- Zhang, Ting,Cao, Xianfei,Wang, Xuchun,Song, Changchun
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p. 505 - 510
(2017/02/05)
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- METHOD OF CONVERTING ALCOHOL TO HALIDE
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The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
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- Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature
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A series of TiO2 supported nano-Pd catalysts (Pd/TiO2) were prepared and used for the N,N-dimethylation of different amines and nitro compounds with methanol under UV irradiation at room temperature. A wide range of N,N-dimethyl amines were one-pot synthesized with up to 98% by applying aliphatic secondary amines, aromatic primary amines, aliphatic primary amines and aromatic nitro compounds as starting materials. It is noteworthy that up to 90% yield of 4-chloro-N,N-dimethylaniline was obtained by adjusting the Pd loadings on the TiO2 and the dehalogenation reaction was inhibited. Finally, a reaction mechanism is discussed, involving PhN = CH2 and PhNHCH3 as reaction intermediates.
- Zhang, Lina,Zhang, Yan,Deng, Youquan,Shi, Feng
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p. 14514 - 14521
(2015/03/05)
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- Room temperature N-alkylation of amines with alcohols under UV irradiation catalyzed by Cu-Mo/TiO2
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It is highly desirable to develop efficient heterogeneous photocatalysts for organic reactions. Here, we show the preparation and catalytic performance of a novel TiO2 (P25) supported Cu and Mo photocatalyst (Cu-Mo/TiO2) for N-alkylation of amines with alcohols under UV irradiation at room temperature. A variety of aromatic and aliphatic amines were selectively converted into the corresponding secondary amines or tertiary amines in moderate to excellent yields without the addition of any co-catalysts such as bases and organic ligands. Noteworthy, this catalytic system is feasible in the alkylation of anilines containing halogen substituents with alcohols and the yields of the desired products are up to 95%.
- Zhang, Lina,Zhang, Yan,Deng, Youquan,Shi, Feng
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p. 3226 - 3234
(2015/06/08)
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- Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system
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A series of acyclic symmetrical and asymmetrical quaternary ammonium chlorides of the general formula R1R2R3N+AR4Cl- (R1 = Me, Bu; R2 = n-C12H25, PhCH2, C n H2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2; R3 = n-C12H25, PhCH2, HOCH2CH2,-OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) was synthesized by the alkylation of tertiary amines in a two-phase system containing water. A convenient method for the synthesis of the initial symmetrical and asymmetrical tertiary amines of the general formula MeNR1R2 (R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2) in an organic phase-aqueous phase heterogeneous system, which allows the use of aqueous solutions of alkali and amines, was developed. The improved method for the preparation of intermediate ethylene glycol and diethylene glycol monoethers is monoalkylation of glycols in dioxane using solid KOH in a two-phase system.
- Kharlamov,Artyushin,Bondarenko
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p. 2445 - 2454
(2015/08/03)
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- Methylformate as replacement of syngas in one-pot catalytic synthesis of amines from olefins
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A new general approach for the one-pot hydroaminomethylation of olefins using methylformate as formylating agent instead of synthesis gas (syngas) has been proposed. Herein we report that a Ru-Rh catalytic system demonstrates high activity in a tandem conversion of a series of n-alkenes into amines using methylformate with yields 58-92% (6 h). The selectivity for the normal amine reached 96% with catalysis by the Ru carbonyl complex Ru3(CO) 12, with an overall yield of 55% with respect to amine in this instance. The addition of the Rh complex to Ru catalytic system, sharply increased the hydroaminomethylation rate of both the terminal and internal alkenes and increased the yield of amines to 82-93% (6-12 h). The Royal Society of Chemistry.
- Karakhanov, Eduard,Maksimov, Anton,Kardasheva, Yulia,Runova, Elena,Zakharov, Roman,Terenina, Maria,Kenneally, Corey,Arredondo, Victor
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p. 540 - 547
(2014/02/14)
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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 0044
(2014/02/16)
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- N-Methylation of amine and nitro compounds with CO2/H2 catalyzed by Pd/CuZrOx under mild reaction conditions
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An active Pd/ZrCuOx catalyst was prepared for the reductive amination of CO2. The N-methylation of amines and nitro compounds with CO2/H2 can be realized with up to 97% yield under relatively mild reaction condi
- Cui, Xinjiang,Zhang, Yan,Deng, Youquan,Shi, Feng
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supporting information
p. 13521 - 13524
(2015/01/09)
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- Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia
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The N-alkylation of amines or ammonia with alcohols is a valuable route for the synthesis of N-alkyl amines. However, as a potentially clean and economic choice for N-alkyl amine synthesis, non-noble metal catalysts with high activity and good selectivity are rarely reported. Normally, they are severely limited due to low activity and poor generality. Herein, a simple NiCuFeOx catalyst was designed and prepared for the N-alkylation of ammonia or amines with alcohol or primary amines. N-alkyl amines with various structures were successfully synthesized in moderate to excellent yields in the absence of organic ligands and bases. Typically, primary amines could be efficiently transformed into secondary amines and N-heterocyclic compounds, and secondary amines could be N-alkylated to synthesize tertiary amines. Note that primary and secondary amines could be produced through a one-pot reaction of ammonia and alcohols. In addition to excellent catalytic performance, the catalyst itself possesses outstanding superiority, that is, it is air and moisture stable. Moreover, the magnetic property of this catalyst makes it easily separable from the reaction mixture and it could be recovered and reused for several runs without obvious deactivation. Copyright
- Cui, Xinjiang,Dai, Xingchao,Deng, Youquan,Shi, Feng
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supporting information
p. 3665 - 3675
(2013/03/29)
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- METHOD FOR PRODUCING TERTIARY AMINE
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The present invention discloses the method for producing a tertiary amine, using the column reactor packed with catalyst layers, containing supplying a liquid and a gaseous raw materials from the bottom of the column, reacting these raw materials in the column, and discharging the product from the top of the column, wherein the column reactor includes two or more honeycomb catalyst layers as the catalyst layers, one or more spaces between each honeycomb catalyst layer, and one or more rectifying sections that prevents a partial or whole back flow of the raw materials, arranged in each space without contacting with the honeycomb catalyst layer.
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Paragraph 0196; 0197; 0198
(2013/11/06)
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- METHOD FOR PRODUCING TERTIARY AMINE
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The present invention provides a method for producing a tertiary amine by using a secondary amine and an alcohol as starting materials to obtain a corresponding tertiary amine. The method of the present invention includes reacting a secondary amine with an alcohol in the presence of a catalyst, wherein the catalyst is previously used in the reaction of a primary amine with an alcohol to obtain a tertiary amine.
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Page/Page column 5
(2012/11/08)
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- METHOD FOR PRODUCING TERTIARY AMINE
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The present invention provides a method for producing a tertiary amine by reacting an alcohol with a primary or secondary amine in the presence of a film catalyst containing a thermosetting resin and an active metal, wherein the film catalyst is reduced at 100 to 150° C., and a method for activating the film catalyst containing a thermosetting resin and an active metal, including applying a coating agent containing the thermosetting resin and a powder catalyst onto the surface of a support, drying the resultant, curing it at 80 to 170° C., and reducing the catalyst at 100 to 150° C.
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Page/Page column 5
(2010/09/05)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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The present invention relates to a process for producing a tertiary amine by reducing an amide compound in the presence of a catalyst containing a sponge copper catalyst obtained by leaching alloy particles containing copper and aluminum and drying the thus leached alloy particles. The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products at a high yield by subjecting aliphatic acid amides to hydrogenation reduction under solvent-free moderate conditions.
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Page/Page column 8
(2010/08/03)
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- New deoxygenation method for amine n-oxides using dimethylthiocarbamoyl chloride
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A facile and efficient deoxygenation method for various amine N-oxides to their corresponding amines is described. The experimental procedure is quite simple and the products are obtained in excellent yields. Copyright Taylor & Francis Group, LLC.
- Caliskan, Hafize,Zaim, Oemer
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experimental part
p. 3078 - 3083
(2010/11/04)
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- METHOD OF PRODUCING NITROGEN-CONTAINING COMPOUND
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The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by using a chromium-free catalyst with a good productivity in an economically advantageous manner. The present invention relates to a process for producing a tertiary amine by reducing an amide compound in the presence of a catalyst containing copper and magnesium at a molar ratio of magnesium to copper (magnesium/copper) of from 0.01 to 20.
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Page/Page column 8-9
(2009/10/01)
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- PROCESS FOR PRODUCING NITROGEN-CONTAINING COMPOUNDS
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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.
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Page/Page column 16-18; 20-21
(2009/04/25)
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- METHOD FOR PRODUCING NITROGEN-CONTAINING COMPOUND
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The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by subjecting aliphatic acid amides to hydrogenation reduction under moderate conditions, as well as a process for producing amine derivatives from the aliphatic tertiary amines, with a good productivity in an economically advantageous manner. The present invention relates to a process for producing an aliphatic tertiary amine by subjecting a specific aliphatic amide to hydrogenation reduction 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 and 7 of the Periodic Table; the catalyst; and a process for producing amine oxide by reacting the tertiary amide obtained by the above production process with hydrogen peroxide.
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Page/Page column 7-8
(2008/12/09)
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- METHOD FOR MANUFACTURING TERTIARY AMINE
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The invention provides a method for manufacturing a tertiary amine, including reacting a tertiary amine with an alcohol and a primary or secondary amine in a reactor loaded with a film type catalyst, controlling the superficial velocity of liquid in the reactor at 0.1 cm/s or more.
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Page/Page column 5-6
(2008/06/13)
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- PROCESS FOR PRODUCING TERTIARY AMINE
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Disclosed is a process for producing a tertiary amine from a primary or secondary amine and alcohol as corresponding starting materials, which includes step (i) of dehydrogenating an alcohol to obtain an aldehyde, step (ii) of reacting the aldehyde with a primary or secondary amine to obtain a primary or secondary amine adduct, and step (iii) of hydrogenating the primary or secondary amine adduct to obtain a tertiary amine, wherein step (ii) is carried out independently of the other steps.
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Page/Page column 41-43; 45
(2010/11/27)
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- FILM CATALYST FOR TERTIARY AMINE PRODUCTION AND METHOD FOR PRODUCING TERTIARY AMINE USING THE SAME
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The invention provides a method of using an alcohol and a primary or secondary amine as the starting material to produce the corresponding secondary amine easily at a high yield and a catalyst used therein. The invention relates to a film-type catalyst for production of a tertiary amine, which is used in producing a tertiary amine from an alcohol and a primary or secondary amine as the starting material, and a process for producing a tertiary amine, which includes reacting an alcohol with a primary or secondary amine in the presence of the film-type catalyst.
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- PROCESS FOR PRODUCTION OF TERTIARY AMINES
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A process for producing a tertiary amine from an alcohol and a primary or secondary amine by use of a film type catalyst, which comprises circulating the reaction fluid through a reaction tank equipped with an external circulation line packed with the film type catalyst at a rate of at least three times/h to conduct the reaction.
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Page/Page column 14-15; 18
(2008/06/13)
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- Process for producing tertiary amine
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The invention relates to a process for producing a tertiary amine, which includes reacting an alcohol with a primary or secondary amine gas in the presence of a catalyst with an agitating vessel under the stirring conditions where the ratio (Pg/P0) of agitating power at the time of the maximum flow rate of an introducing gas (Pg [W]) to agitating power at the time of no introduction of the gas (P0 [W]) becomes 10?1.8Na or more wherein Na is the gas flow number, and Na=Qg/nd3 whereupon Qg [m3/s] is the flow rate of an introducing gas, n [1/s] is the number of revolutions, and d [m] is the diameter of an agitating impeller.
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Page/Page column 3-4
(2008/06/13)
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- PROCESS FOR OBTAINING AMINES BY REDUCTION OF AMIDES
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Disclosed is a process for the preparation of primary, secondary and tertiary amines via a catalytic hydrogenation of unsubstituted, N- substituted, and N,N- disubstituted amides. The amide is led, together with an auxiliary amine, in vaporised form in a hydrogen containing gas flow over the catalyst. The process can be carried out at relatively low pressures, between 2 and 50 bars, using typical hydrogenation catalysts like CuCr-type catalysts. The amine is obtained with high yield and high selectivity. The process can be carried out in a continuous fixed bed reactor.
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Page/Page column 12
(2008/06/13)
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- Process for obtaining amines by reduction of amides
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Disclosed is a process for the preparation of primary, secondary and tertiary amines via a catalytic hydrogenation of unsubstituted, N-substituted, and N,N-disubstituted amides. The amide is led, together with an auxiliary amine, in vaporised form in a hydrogen containing gas flow over the catalyst. The process can be carried out at relatively low pressures, between 2 and 50 bars, using typical hydrogenation catalysts like CuCr-type catalysts. The amine is obtained with high yield and high selectivity. The process can be carried out in a continuous fixed bed reactor.
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Page/Page column 4,5
(2008/06/13)
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- PROCESS FOR MAKING LONG CHAIN INTERNAL FATTY TERTIARY AMINES
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The invention relates to a process for preparing long chain internal fatty amines, quaternized amines and amine oxides and selected amine oxides having a symmetric alkyl portion.
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Page/Page column 18; 19
(2010/11/30)
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- Studies into reactions of N-methylmorpholine-N-oxide (NMMO) and its hydrates with cyanuric chloride
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The course of the reaction between N-methylmorpholine-N-oxide (NMMO, 1a) and cyanuric chloride (2) is strictly dependent on the hydrate water content of the amine oxide. In solid phase, both substances undergo an explosion-like, extremely exothermic reaction. In solution, this process becomes controllable and leads to a quantitative degradation of NMMO into morpholine and formaldehyde, with 2 only acting as an inducing agent. The reaction can be conducted in a way that a clean deoxygenative demethylation is achieved. The monohydrate of NMMO (1b) is quantitatively converted into N-methylmorpholine and hypochlorous acid by the action of 2. This conversion can be used in synthesis either to deoxygenate tertiary amine N-oxide monohydrates, or to produce chlorohydrins in non-aqueous, organic media in superior yields. The semisesquihydrate of NMMO (1c) reacts with 2 under consumption of water until non-hydrated NMMO is present, which is then further converted into morpholine and HCHO, as in the case of 1a being directly employed as the starting material.
- Rosenau, Thomas,Potthast, Antje,Kosma, Paul
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p. 9809 - 9815
(2007/10/03)
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- 1-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) as a selective reducing agent
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1-Benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate (BAAOTB) 1 generated as white solid from commercially available DABCO and sodium borohydride is found to be a selective and versatile reducing agent. The reagent in t-butanol is very useful for reduction of imines, enamines, oximes, reductive amination of aldehydes and ketones and reductive methylation of amines.
- Hajipour,Mohammadpoor-Baltork,Rahi
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p. 239 - 242
(2007/10/03)
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- Process for purifying tertiary fatty alkylmethylamines
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In the process described, purification and improvement in odor of, in particular, fatty alkyldimethylamines is achieved by exposing, in the liquid phase, the tertiary amine to be treated to a vacuum or an inert gas stream. By means of the process according to the invention, in a relatively short time and in a simple and economical manner, a tertiary fatty alkylmethylamine is obtained which is essentially trimethylamine-free and improved in odor.
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- Deoxygenation of amine oxides by in situ-generated formic pivalic anhydride
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A novel method for the highly efficient deoxygenation of tertiary and aromatic amine oxides is described. The initial step of the reaction is the O-formylation of the amine oxide by formic pivalic anhydride which is produced in situ. The approach has the advantage of superior convenience in preparation and work-up since all products of the reaction are solids or gases rendering the amine very readily separable.
- Rosenau, Thomas,Potthast, Antje,Ebner, Gerald,Kosma, Paul
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p. 623 - 625
(2007/10/03)
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- Zwitterionic sulfobetaine inhibitors of squalene synthase
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A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC50 = 10 μM and aromatic derivative 35 has IC50 = 2 μM for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.
- Spencer, Thomas A.,Onofrey, Thomas J.,Cann, Reginald O.,Russel, Jonathon S.,Lee, Laura E.,Blanchard, Daniel E.,Castro, Alfredo,Gu, Peide,Jiang, Guojian,Shechter, Ishaiahu
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p. 807 - 818
(2007/10/03)
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- Mild and Efficient Flavin-Catalyzed H2O2 Oxidation of Tertiar Amines to Amine N-Oxides
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A mild and highly effective H2O2 oxidation of tertiary amines has been developed by the use of flavin catalysis. Eight aliphatic amines were oxidized to their corresponding N-oxides in fast and selective reactions. For all substrates a considerable rate enhancement was observed compared to the noncatalyzed reactions. The product N-oxides were isolated in good yields using this mild oxidation system based on the environmentally attractive oxidant H2O2. As the catalyst, an N1N5- dialkylated flavin was used as an analogue of the biologically important flavin redox cofactor. The catalytic cycle proposed for the flavin catalysis accounts for the observation that, in addition to the hydrogen peroxide oxidant, molecular oxygen is required for the initiation of the process.
- Bergstad, Katarina,B?ckvall, Jan-E.
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p. 6650 - 6655
(2007/10/03)
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- Process for the conversion of fatty amides to amines
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Disclosed is a process for the preparation of primary, secondary and tertiary amines with high conversion and high selectivity via low pressure catalytic hydrogenation of unsubstituted, N-substituted, and N,N-disubstituted amides. Amide hydrogenation is conducted using a catalyst system comprising copper chromite and a nucleophilic reagent, in combination with hydrogen gas. The process allows for production of amines which may be directly used as chemical intermediates in the manufacture of surfactants, quaternary ammonium compounds, bactericides, disinfectants, lubricants, petroleum additives, ion exchange resins and the like, without the need of purification, such as distillation.
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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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- 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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- Process for preparing alkylamines
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This invention relates to an improvement in a process for producing an alkylamine from olefin and amine by hydrohalogenating the olefin to form haloalkane then reacting the haloalkane with amine to form an alkylamine. The improvement comprises heat-treating the alkylamine thus formed with an aqueous alkaline or alkaline earth metal hydroxide at a temperature and for a period of time sufficient to minimize the formation of flocculent precipitate during the formation and/or storage of the alkylamine.
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- Polystyrene anion exchange polymers
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Polystyrene polymers bearing a quaternary ammonium group are disclosed. They are useful in the treatment of hypercholesterolaemia and the prevention of atherosclerosis. A compound of the invention is 6-(N,N-dimethyl-N-octylammonio)hexanoylated polystyrene chloride.
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- Characterization of Highly Selective Cu-Ni Amination Catalysts
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The characterization of Cu-Ni amination catalysts has been done by using TEM, XPS, and EXAFS.THe Cu-Ni catalyst whose nickel atoms were hard to be reduced even at high temperatures under a hydrogen atmosphere gave high selectivity in the reaction between dodecyl alcohol and dimethylamine to produce N,N-dimethyldodecylamine.
- Abe, Hiroshi,Hoshi, Satoko,Domen, Kazunari,Maruya, Ken-ichi,Ohtaki, Hitoshi,Onishi, Takaharu
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p. 401 - 404
(2007/10/02)
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