- Organic passivation layer on flexible Surlyn substrate for encapsulating organic photovoltaics
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Barrier materials are required for encapsulating organic devices. A simple methodology based on organic passivation layer on a flexible substrate has been developed in this work. Stearyl stearate (SS) was directly coated over the flexible Surlyn film. The barrier films with SS passivation layer exhibited much lower water vapor transmission rates compared to the neat Surlyn films. Moreover, the effect of the process of deposition of organic passivation layer on the resultant water vapor properties of the barrier films was evaluated. The accelerated lifetime studies conducted on encapsulated organic photovoltaics showed that the passivation layer improved the device performance by several fold compared to the non-passivated barrier films.
- Seethamraju, Sindhu,Ramamurthy, Praveen C.,Madras, Giridhar
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- Effect of Zn/Al ratio of Ni/ZnO-Al2O3 catalysts on the catalytic deoxygenation of oleic acid into alkane
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Ni-based catalysts supported on Zn-Al composite oxides have been prepared for the catalytic deoxygenation of oleic acid into diesel-ranged alkanes, and the effects of the Zn/Al ratio on the physico-chemical properties of the supports and the deoxygenation activity of the final catalyst were investigated in detail. The results showed that higher Zn/Al ratios led to lower specific surface area of the supports and weakening of the interaction between Ni species and supports thereby improving the reducibility of Ni species. However, higher Zn/Al ratios may limit the dispersion of Ni species, leading to a decrease in the exposure of metallic Ni. Because the conversion and deoxygenation of the reactants mainly depended on the hydrogenation capability of the catalysts which was controlled by the amount of exposed metallic Ni, the catalyst with a Zn/Al ratio of 2/1 showed the highest hydrogenation rate and alkane yield. Further decreasing the Zn/Al ratio led to strong metal-support interaction, making the Ni species difficult to reduce, which may also inhibit the formation of alkane products. In addition, the change in Zn/Al ratio affected intermediate type, which could affect the yield of alkane products.
- Chen, Lei,Zhang, Feng,Li, Guangci,Li, Xuebing
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- Intramolecular charge-transfer fluorescence of 1-phenyl-4-piperidine (fluoroprobe) as a sensor for phase transitions in the solid state
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As evidenced by temperature-dependent wide-angle X-ray diffraction (WAXD), the thermochromism of the continuous and time-resolved (nanosecond time scale) fluorescence behaviour of 1-phenyl-4-piperidine (fluoroprobe) dissolved in octadecyl octadecanoate is shown to be a highly sensitive probe for a phase transition in the solid state occurring in the latter.
- Jenneskens, Leonardus W.,Verhey, Herman J.,Ramesdonk, Hendrik J. van,Verhoeven, Jan W.,Malssen, Kees F. van,Schenk, Henk
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- Efficient greener methodology for the preparation of bio-based phase change materials from lipids
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In the present work, a new, highly efficient and simple strategy has been developed for the synthesis of long chain esters from fatty acids and fatty alcohols as phase change materials. Equivalent amounts of the selected starting compounds were taken to the esterification reaction at 110 °C in a solventless medium. In order to catalyze the esterification reaction, non-hygroscopic triphenylphosphine-sulfur trioxide adduct was used (0.83 mmol%) which is an easily accessible compound. The relevant reaction was completed in a very short time (2 h) and under optimized esterification conditions, excellent conversion were reached. The targeted mono ester compounds (15 examples) were obtained in good to excellent yields even after a simple crystallization step (72-99%). Additionally, a catalyst reuse investigation and study covering the scale-up production of stearyl stearate was also carried out. The triphenylphosphine-sulfur trioxide catalyzed solvent free process can compete with existing processes and proved to be a cheaper, practical and environmentally-friendly method for the esterification of fatty acids and alcohols.
- Y?ld?r?m, Ayhan,K?raylar, Kaan
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p. 407 - 413
(2020/11/19)
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- PRODUCTION METHOD OF ESTER COMPOUND
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PROBLEM TO BE SOLVED: To produce an ester compound at a high conversion even under mild reaction conditions. SOLUTION: A production method of an ester compound includes a reaction step for reacting a carboxylic acid of 8-22 carbons and an alcohol of 8-22 carbons at a temperature of 50-100°C in an ionic liquid composed of a phosphonium cation or an imidazolium cation and a trifluoromethanesulfonic acid anion or a bis (trifluoromethanesulfonyl) imide anion to obtain an ester compound in a liquid phase different from an ionic liquid phase. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0030; 0033
(2019/10/01)
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- Fatty acid ester-based wax compositions and methods of making thereof
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This invention relates to a wax composition comprising one or more fatty acid diester compounds having the formula of R1 and R2 are each independently a substituted or unsubstituted C4 to C50 alkyl or aryl; and n1 is an integer from 2 to 10. This invention also relates to a wax composition comprising: a) one or more fatty acid monoester or diester compounds having the formula of: and b) one or more hydroxylated fatty acid diester compounds having the formula of In these formulae, R is H or COR1′; R1′ and R2′ are each independently a substituted or unsubstituted C4 to C50 alkyl or aryl; n2 is an integer from 2 to 24; m is an integer from 2 to 12; and .(OH)m represents 2 to 12 hydroxyl groups substituting for 2 to 12 hydrogen atoms in the alkyl groups R1′ and/or R2′. Uses of the compositions are also disclosed.
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Page/Page column 22; 23; 27
(2019/07/29)
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- Solid Wax Composition and Solid Oily Cosmetic
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The present invention provides a composition that has an excellent hardness adjustment action, can be used as a solidifying agent for various cosmetics, and when added to cosmetics, can impart those cosmetics with excellent shape retention properties, an oil oozing suppression effect during use, a favorable texture and good storage stability, and also provides an oily solid cosmetic to which the composition has been added. Specifically, the invention provides a solid wax composition containing a component (A):candelilla wax, and a component (B): a monoester having a total of 40 to 48 carbon atoms, wherein the mass ratio between the component (A) and the component (B) in the solid wax composition satisfies component (A):component (B)=45:55 to 95:5, and the monoester is a monoester of a monovalent fatty acid and a monohydric alcohol.
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Paragraph 0091
(2019/10/20)
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- Oxidative esterification of primary alcohols at room temperature under aqueous medium
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Oxidative esterification of aliphatic primary alcohols with bromide and bromate couple in aqueous acidic medium at room temperature is reported with a wide range of substrate scope for both aliphatic and cyclic alcohols and obtained excellent yields of products.
- Reddy, N. Naresh Kumar,Ravi, Chitrakar,Adimurthy, Subbarayappa
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p. 1663 - 1670
(2018/06/15)
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- Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst
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The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. α-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.
- Ullrich, Johannes,Breit, Bernhard
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p. 785 - 789
(2018/02/14)
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- Manganese Pincer Complexes for the Base-Free, Acceptorless Dehydrogenative Coupling of Alcohols to Esters: Development, Scope, and Understanding
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Aliphatic PNP pincer-supported earth-abundant manganese(I) dicarbonyl complexes behave as effective catalysts for the acceptorless dehydrogenative coupling of a wide range of alcohols to esters under base-free conditions. The reaction proceeds under neat conditions, with modest catalyst loading and releasing only H2 as byproduct. Mechanistic aspects were addressed by synthesizing key species related to the catalytic cycle (characterized by X-ray structure determination, multinuclear (1H, 13C, 31P, 15N, 55Mn) NMR, infrared spectroscopy, inter alia), by studying elementary steps connected to the postulated mechanism, and by resorting to DFT calculations. As in the case of related ruthenium and iron PNP catalysts, the dehydrogenation results from cycling between the amido and amino-hydride forms of the PNP-Mn(CO)2 scaffold. For the dehydrogenation of alcohols into aldehydes, our results suggest that the highest energy barrier corresponds to the hydrogen release from the amino-hydride form, although its value is close to that of the outer-sphere dehydrogenation of the alcohol into aldehyde. This contrasts with the ruthenium and iron catalytic systems, where dehydrogenation of the substrate into aldehyde is less energy-demanding compared to hydrogen release from the cooperative metal-ligand framework.
- Nguyen, Duc Hanh,Trivelli, Xavier,Capet, Frédéric,Paul, Jean-Fran?ois,Dumeignil, Franck,Gauvin, Régis M.
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p. 2022 - 2032
(2017/08/14)
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- Controlling Hydrodeoxygenation of Stearic Acid to n-Heptadecane and n-Octadecane by Adjusting the Chemical Properties of Ni/SiO2–ZrO2 Catalyst
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A series of SiO2–ZrO2 mixed oxides with varying SiO2 concentrations were hydrothermally synthesized and used as support for Ni in the hydrodeoxygenation of stearic acid. ZrO2 provides a relatively low surface area and only Lewis acid sites, and Ni supported on ZrO2 produces n-heptadecane from stearic acid through hydrogenation and decarbonylation. The SiO2–ZrO2 mixed oxides have a higher specific surface area than ZrO2 as well as an unprecedented spherical and nanolayered morphology. Br?nsted acid sites were created by the incorporation of SiO2 into ZrO2, promoting the hydrodeoxygenation activity of Ni and specifically opening a new reaction route to n-octadecane through the dehydration of 1-octadecanol intermediate into 1-octadecene with subsequent hydrogenation.
- Foraita, Sebastian,Liu, Yue,Haller, Gary L.,Baráth, Eszter,Zhao, Chen,Lercher, Johannes A.
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p. 195 - 203
(2017/01/17)
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- METHOD FOR PRODUCING ALCOHOL BY HYDROGENATION OF CARBOXYLIC ACID COMPOUND, AND RUTHENIUM COMPLEX FOR USE IN THE PRODUCTION METHOD
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PROBLEM TO BE SOLVED: To provide a method of obtaining an alcohol by efficiently hydrogenating a variety of carboxylic acid compounds under mild conditions using a homogeneous catalyst. SOLUTION: The present invention provides a method of hydrogenating a carboxylic acid compound, in the presence of a ruthenium complex represented by RuXnYpZq, in an atmosphere of hydrogen [X is a group represented by the following formula; Y is a phosphine ligand having a substituted/unsubstituted alkyl group or a substituted/unsubstituted aryl group; Z is a ligand other than X and Y; n is 1 or 2; p is an integer of 1-4; q is an integer of 0-2] {R1 is H, a substituted/unsubstituted alkyl group or a substituted/unsubstituted aryl group; A1 and A2 independently represent O, NR4 (R4 is H, a substituted/unsubstituted alkyl group or a substituted/unsubstituted aryl group) or S; m is an integer of 1 or more; a solid line and a dashed line both represent a single bond or a double bond}]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0133; 0137; 0138
(2017/02/02)
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- Highly Selective Hydrodecarbonylation of Oleic Acid into n-Heptadecane over a Supported Nickel/Zinc Oxide-Alumina Catalyst
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The production of second-generation biodiesel with triglycerides or their derivatives through hydroprocessing is considered as a promising approach to make transportation fuels. In this study, a series of Ni-based catalysts supported on basic composite oxides (MO-Al2O3, M=Mg, Ca, Ni, Cu, Zn) were prepared for the catalytic deoxygenation of oleic acid in the presence of H2. Ni/ZnO-Al2O3 exhibited the highest deoxygenation activity and alkane selectivity, which depended on its moderate basicity. Investigations of the reaction conditions, which include reaction time, reaction temperature, H2 pressure, and Ni loading, suggested that n-heptadecane was the predominant product and its content increased with reaction temperature. The reaction temperature was more important than H2 pressure in the catalytic deoxygenation of oleic acid. Additionally, the overall reaction pathways for the conversion of oleic acid were proposed based on the product distribution for different durations and reaction rates of stearic acid, 1-octadecanol, and stearyl stearate, in which the oxygen atoms in the oleic acid were mainly removed in the form of CO through a hydrogenation-dehydrogenation-decarbonylation reaction route. If glycerol trioleate was used instead of oleic acid, Ni/ZnO-Al2O3 exhibited a high hydrodecarbonylation activity and selectivity to n-heptadecane.
- Li, Guangci,Zhang, Feng,Chen, Lei,Zhang, Chuanhui,Huang, He,Li, Xuebing
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p. 2646 - 2653
(2015/09/15)
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- Unprecedented reductive esterification of carboxylic acids under hydrogen by reusable heterogeneous platinum catalysts
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Supported metal catalysts have been tested for an unprecedented reductive dimerization of carboxylic acids to esters under 8 bar hydrogen in solvent-free conditions. Among various metal-loaded tin oxide catalysts, platinum-loaded tin dioxide (Pt/SnO2) shows the highest ester yield for the reaction of dodecanoic acid. Among Pt catalysts on various supports, Lewis acidic oxides, especially SnO2, show high activity. The most active catalyst, 5 wt% Pt/SnO2 reduced at 100°C, is effective for the reductive esterification of various carboxylic acids, and the catalyst is reusable for nine cycles, demonstrating the first successful example for the title reaction. Infrared (IR) studies of a model compound (formic acid) on some metal oxides indicate a strong Lewis acid-base interaction between SnO2 and the carbonyl oxygen. For Pt/SnO2 catalysts with different Pt particle sizes, the activity increases with decreasing size of Pt metal. A cooperative catalysis of the Pt metal nanoparticles and the Sn4+ Lewis acid sites is proposed.
- Touchy, Abeda S.,Kon, Kenichi,Onodera, Wataru,Shimizu, Ken-Ichi
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p. 1499 - 1506
(2015/05/19)
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- Effects of Si/Al ratio and Pt loading on Pt/SAPO-11 catalysts in hydroconversion of Jatropha oil
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A series of Pt/SAPO-11 catalysts were prepared with various Si/Al ratios and Pt loadings and characterized by using BET, XRD, XRF, and CO pulse adsorption, as well as 29Si NMR and NH3-TPD techniques. Their catalytic performances in hydroconversion of Jatropha oil were tested with a fixed-bed flow reactor system. The isomerization activity increased with the Si/Al ratio because there were more medium acidic sites on the SAPO-11 supports. Pt/SAPO-11 catalysts with a Si/Al ratio of 0.4 demonstrated high activity for both deoxygenation and isomerization among catalysts with the same Pt loading. The deoxygenation, isomerization and cracking activities strongly depended on the Pt loading. The best activity was observed for the sample with a 3 wt% Pt loading, which generated an 83% yield of iso-C15-18 hydrocarbons under the LHSV of 0.5 h-1. Based on the mechanistic study of hydroconversion of methyl oleate, a reaction network for the hydroconversion of Jatropha oil was suggested.
- Chen, Ning,Gong, Shaofeng,Shirai, Hisakazu,Watanabe, Toshitaka,Qian, Eika W.
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p. 105 - 115
(2013/08/23)
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- Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions
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A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.
- Chen, Hu,Xu, Xunfu,Liu, Liu,Tang, Guo,Zhao, Yufen
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p. 16247 - 16250
(2013/09/23)
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- Permeable composite membrane as a catalytically active contactor for hydrogenation reactions
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The efficiency of using of the permeable composite membrane (PCM) is demonstrated in the 3-phase reaction of liquid substrate with gaseous hydrogen on solid catalyst (PCM acts as a catalytically active contactor) - hydrogenation of fatty acid triglyceride. PCM provides a good combination of the opposite requirements of mild internal diffusion restrictions, low hydraulic resistance, high thermal conductivity, well-developed gas-liquid interface and high catalyst loading in the reactor volume, and thus assures the control of the course of the catalytic reaction.
- Minyukova, T. P.,Shtertser, N. V.,Khassin, A. A.,Yurieva, T. M.
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p. 107 - 110,4
(2020/08/20)
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- Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols
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(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).
- Chakraborti, Asit K.,Singh, Bavneet,Chankeshwara, Sunay V.,Patel, Alpesh R.
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supporting information; experimental part
p. 5967 - 5974
(2009/12/24)
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- A mild and efficient method for esterification and transesterification catalyzed by iodine
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Iodine, was found to be a practical and useful Lewis acid catalyst for the esterification of carboxylic acids with alcohols. The high catalytic activity of iodine can be used for the transesterification of esters by different alcohols including tertiary alcohols and sterically hindered primary and secondary alcohols. The method presented is especially effective for simultaneous esterification and transesterification reactions.
- Ramalinga,Vijayalakshmi,Kaimal
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p. 879 - 882
(2007/10/03)
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- Hydrogenation of fatty esters over ruthenium-tin catalysts; characterization and identification of active centers
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The selective hydrogenation of methyl oleate into oleyl alcohol was performed over RuSn/alumina catalysts. A maximum yield of unsaturated alcohol was obtained for a bulk atomic ratio to Sn/Ru = 4. The side reaction of the transesterification between methyl oleate and oleyl alcohol leading to oleyl oleate was strongly decreased. The ruthenium-tin catalysts prereduced with NaBH4 have been characterized by TPR and XPS analysis. The addition of tin increased the content of Ru° on the catalyst surface without modification of the total Ru content. When the catalysts were reduced with NaBH4, a decrease of the tin and ruthenium contents on the surface was observed. On the catalyst surface were found two separate tin oxide species which differed in the oxidation state of tin. The proportion and the repartition of each species was a function of the total tin content. Over such catalysts, the reaction scheme involved three steps: (1) the hydrogenation of the methyl oleate into the oleyl alcohol, (2) the transesterification reaction between the methyl oleate and the oleyl alcohol with the formation of the heavy oleyl oleate ester, (3) the hydrogenation of this heavy ester into oleyl alcohol. The first and the third steps could involve mixed ruthenium-tin sites while the second step could require tin species without an interaction with ruthenium. If it is assumed that the rate determining step is the oleyl oleate hydrogenation, the results of this study show that active centers corresponding to a stoechiometry Ru/SnOx = 2 could be involved in this reaction. The activation of esters (methyl oleate and oleyl oleate) would occur via a hemiacetal intermediate over these mixed sites where the more reduced tin species could be close to the ruthenium.
- Pouilloux,Autin,Guimon,Barrault
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p. 215 - 224
(2007/10/03)
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- The synthesis of esters under microwave irradiation using dry-media conditions
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Practical and simple techniques are described for using nonmodified domestic microwave ovens as safe and convenient laboratory devices to obtain numerous esters.High pressures are avoided by conducting reactions with reactants impregnated on solid mineral supports in "dry media" or by phase transfer catalysis (PTC) in the absence of organic solvents.Two kinds of microwave effects are involved: (1) displacement of the equilibrium by evaporation of volatile polar molecules (water or alcohols) in esterfications and transesterfications; (2) acceleration of ionic reactions in carboxylate alkylations.As solvents are avoided, there is no need for sealed vessels and water separators.
- Loupy, Andre,Petit, Alain,Ramdani, Mohamed,Yvanaeff, Celine,Majdoub, Mustapha,et al.
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