- PROCESS FOR PRODUCING CYANONORBORNENE
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A process for producing cyanonorbornene of the present invention includes Step 1 of preparing a mixture solution including 0.5% by weight to 28% by weight of methyl bicyclononadiene, with respect to a total amount of 100% by weight of dicyclopentadiene, acrylonitrile, and the methyl bicyclononadiene, in a container, and Step 2 of reacting the bicyclopentadiene with the acrylonitrile in the presence of the methyl bicyclononadiene, in the mixture solution.
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Paragraph 00148-0149
(2020/08/19)
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- Thiocyanate radical mediated dehydration of aldoximes with visible light and air
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We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
- Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
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supporting information
p. 9701 - 9704
(2019/08/15)
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- Process for preparing dicyanonorbornane compound
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The present invention relates to a method for manufacturing a dicyano norbornane isomer compound by hydro-cyanolating a carbon-carbon double bond of 5-norbornenecarbonitrile with a metal cyan compound. According to the present invention, a dicyano norbornane compound can be efficiently manufactured by using a divalent nickel catalyst in an aqueous solution.COPYRIGHT KIPO 2020
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Paragraph 0037-0039
(2019/11/19)
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- Process for the Catalytic Reversible Alkene-Nitrile Interconversion
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The present invention refers to processes for catalytic reversible alkene-nitrile interconversion through controllable HCN-free transfer hydrocyanation.
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Page/Page column 28
(2017/09/02)
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- METHOD FOR PRODUCING ALDEHYDE COMPOUND
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A preparation method of an aldehyde compound of the present invention includes a step of reacting a compound represented by the following general formula (a1) with hydrogen and carbon monoxide in the presence of a metal compound including 0.01 ppmmol to 10 ppmmol of a metal belonging to Groups 8 to 10 with respect to 1 mole of the compound and a phosphorus compound, and in the step, the amount of acrylonitrile included in the compound represented by the general formula (a1) is equal to or less than 200-fold by mole with respect to 1 mole of the metal belonging to Groups 8 to 10.
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Paragraph 0076
(2015/11/09)
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- PURIFICATION METHOD OF ALDEHYDE COMPOUND
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The purification method of an aldehyde compound of the present invention includes a step of neutralizing a reaction solution containing an aldehyde compound by adding water and a base compound to the reaction solution, and a step of distilling the neutralized reaction solution, in which the reaction solution is obtained by reacting a compound represented by the following Formula (a1) or (a2) with hydrogen and carbon monoxide in the presence of a metal compound of groups 8 to 10 and a phosphorus compound, the phosphorus compound is represented by Formula (R1O)3P, and the base compound is at least one kind selected from among carbonate and hydrogen carbonate of metals of group I on the periodic table and carbonate and hydrogen carbonate of metals of group II on the periodic table.
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Paragraph 0139
(2015/11/18)
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- ALDEHYDE COMPOUND PRODUCTION METHOD
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A process for producing an aldehyde compound of the invention comprising: reacting a compound represented by the following formula (a1) or (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2) to synthesize an aldehyde compound; wherein the condition (1) is that a content of a metal included in the compound containing a metal belonging to Groups 8 to 10 is 0.01 ppmmol to 300 ppmmol with respect to 1 mol of the compound represented by the formula (a1) or (a2), and wherein the condition (2) is that a molar ratio represented by the phosphorous compound (mol)/ the metal (mol) is 100 or more;
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Paragraph 0088
(2014/04/03)
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- Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst
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An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.
- Sridhar, Madabhushi,Reddy, Mallu Kishore Kumar,Sairam, Vangipuram Venkata,Raveendra, Jillella,Godala, Kondal Reddy,Narsaiah, Chinthala,Ramanaiah, Beeram China,Reddy, Cirandur Suresh
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experimental part
p. 3421 - 3424
(2012/08/08)
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- Conversion of aldoximes into nitriles with raney nickel in refluxing 2-propanol
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Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol. Copyright Taylor & Francis Group, LLC.
- Zuidema, Daniel R.,Dennison, Ami L.,Park, Elizabeth Y.,Mebane, Robert C.
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p. 3810 - 3815
(2008/12/23)
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- A PROCESS FOR PRODUCING ACETYLNORBORNENE, AN INTERMEDIATE IN THE SYNTHESIS OF BIPERIDEN
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The present invention relates to a novel process for the production of acetylnorbornene, efficiently and industrially useful manner. The process is applicable for the large scale production of acetylnorbornene and consists of preparation of 5-cyanonorbornene and its reaction with appropriate Grignard reagents. The product contains higher proportion of the exo form than the endo form, which is important for the synthesis of biperiden.
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Page/Page column 3-4
(2008/12/06)
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- Enhanced Diels-Alder reactions: on the role of mineral catalysts and microwave irradiation in ionic liquids as recyclable media
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This manuscript explores in detail the combined effect of solid supports or microwave irradiation in ionic liquids on a series of Diels-Alder reactions involving 1,3-cyclopentadiene and numerous dienophiles.
- López, Ignacio,Silvero, Guadalupe,Arévalo, María José,Babiano, Reyes,Palacios, Juan?Carlos,Bravo, José Luis
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p. 2901 - 2906
(2007/10/03)
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- Synthesis, characterisation of carbon-bridged (diphenolato)lanthanide complexes and their catalytic activity for Diels-Alder reactions
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The synthesis and structures of new lanthanide complexes supported by the carbon-bridged diphenolato ligand 2,2′-methylenebis(6-tert-butyl-4- methylphenolato) (MBMP2-) are described. Reactions of anhydrous lanthanide trichlorides with Na2MBMP in a 1:2 molar ratio in THF at room temperature afforded the corresponding "ate" (diphenolato) lanthanide complexes [(THF)nLn(MBMP)2Na(THF)2] [Ln = Nd (1), Sm (2), n = 2; Ln = Yb, n = 1 (3)]. Recrystallisation of complexes 1-3 from toluene in the presence of DME gave the discrete ion-pair complexes [(MBMP)2Ln(THF)2][Na(DME) 2(THF)2] [Ln = Nd (4), Sm (5), Yb (6)]. These complexes have been fully characterised. The single-crystal structural analyses of 1, 3 and 6 revealed that the coordination geometries of the lanthanide ions can be best described as distorted octahedral in complexes 1 and 6 and distorted trigonal-bipyramidal in complex 3. It was found that these lanthanide complexes are able to act as Lewis acids to catalyse the Diels-Alder reactions of cyclopentadiene with substituted dienophiles with good activity and stereoselectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Xu, Xiaoping,Ma, Mengtao,Yao, Yingming,Zhang, Yong,Shen, Qi
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p. 676 - 684
(2007/10/03)
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- An in-depth look at the effect of Lewis acid catalysts on Diels-Alder cycloadditions in ionic liquids
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The present work explores in detail the Diels-Alder reaction between cyclopentadiene and a series of dienophiles, performed in an innovative medium such as an ionic liquid. The potential activation of different Lewis acid catalysts and their load effect when used in combination with this solvent have been explored, in order to settle the improvement on rates and selectivities.
- Silvero, Guadalupe,Arévalo, María José,Bravo, José Luis,ávalos, Martín,Jiménez, José Luis,López, Ignacio
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p. 7105 - 7111
(2007/10/03)
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- Diels-Alder reaction in air- and moisture-stable zinc-containing ionic liquids
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Diels-Alder reactions in a number of air- and moisture-stable dialkylimidazolium halide-ZnCl2 ionic liquids are reported. High yields and high endo selectivities have been observed. The ionic liquids could then be recyclable without loss of reactivity.
- Sun, I.-Wen,Wu, Shin-Yi,Su, Chia-Hao,Shu, Yu-Lin,Wu, Pei-Lin
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p. 367 - 370
(2007/10/03)
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- Entrapment of cyclopentadiene in zeolite NaY and its application for solvent-free Diels-Alder reactions in the nanosized confined environment
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Nonpolar cyclopentadiene was stably entrapped as a monomer in the hydrophilic supercages of zeolite NaY. A monomer form of cyclopentadiene in the supercages was confirmed by 13C MAS NMR spectroscopy. The adsorbed cyclopentadiene in the confined cavities performed the Diels-Alder reaction with typical dienophiles under solvent-free conditions more effectively than in organic and water media.
- Imachi, Shouhei,Onaka, Makoto
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p. 4943 - 4946
(2007/10/03)
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- Experimental evidence to support viscosity dependence of rates of Diels-Alder reactions in solvent media
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This note is aimed at ascertaining whether rates of Diels-Alder reactions depend on the viscosity of solvent media in which the reactions are performed. On the basis of the data collected from the literature and in this laboratory, it is seen in general that the rates increase in the solvents with their viscosities ranging up to ~1.2 cP. In solvents possessing viscosities above 1.2 cP, a drop in the reaction rates is observed in all cases. The effect of temperature on the above phenomena is also examined.
- Kumar, Anil,Deshpande, Suvarna S.
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p. 5411 - 5414
(2007/10/03)
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- The nature of lithium perchlorate and gallium chloride salt effect in cycloaddition reactions
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Comparing the acceleration effects of (4 + 2)-, (3 + 2)- and (2 + 2)-cycloaddition reactions in the presence of the salts of two types: gallium chloride in inert solvents and lithium perchlorate (LP) in diethyl ether (DE) it was observed that in the presence of GaCl3 the acceleration effect is approximately the same (104 times) for the studied reactions, while in LPDE medium for the same reactions strong increase (up to 104 times), weak increase or even decrease of the rate and equilibrium constants take place even with the common dienophile depending on the nature of the second reagent. it was suggested that the acceleration effect of cycloaddition reactions in the presence of such Lewis acids as aluminum, gallium or boron halides is due to the sharp increase of Π-acceptor properties of dienophiles and therefore increasing energy of orbital interaction, whereas LPDE medium demonstrates strong stabilization of static and/or dynamic polar forms and favors reactions with charge control.
- Shtyrlin, Yury G.,Murzin, Dmitry G.,Luzanova, Natalia A.,Iskhakova, Gulnara G.,Kiselev, Vladimir D.,Konovalov, Alexandr I.
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p. 2631 - 2646
(2007/10/03)
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- α-Acetyl- and α-Cyanovinyl 2,4-Dinitrophenyl Carboxylate as Useful Ketene Equivalents for the Diels-Alder Reaction
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Two ketene equivalents (5 and 35) have been developed for use in the Diels-Alder reaction. These dienophiles exhibit a marked increase in reactivity in comparison with the more conventional acetoxyacrylonitrile. Conversions of the cycloadducts to the requisite ketones occurs under mild, and moderate to high yielding conditions.
- MaGee, David I.,Lee, May Ling
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p. 786 - 788
(2007/10/03)
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- BISREAGENTS IN THE DIELS-ALDER REACTION. VII. PRODUCTION OF POLYADDUCTS FROM THE REACTION OF BISPOLYMETHYLCYCLOPENTADIENES AND BISMALEIMIDES AND THEIR PROPERTIES
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Polymethylcyclopentadienes and bisdienes exhibit high reactivity with mono- and bisdienophiles in the Diels-Alder reaction.By reaction calorimetry in solution, differential scanning calorimetry, and derivatography it was found that the mono-, bis-, and polyadducts have high thermal stability.The ionization potentials, determined for a series of dienes by photoelectron spectroscopy and spectrophotometry of charge-transfer complexes, lie in the range of 7.15-8.5 eV.The coefficients of the Kuhn-Houwink equation were calculated from data on the characteristic viscosity of the solutions of the polyadducts.They agree with the spherical shape of the polyadducts.The molecular mass of the new polyadducts is greater than 100000.
- Kiselev, V. D.,Sakhabutdinov, A. G.,Shakirov, I. M.,Zverev, V. V.,Konovalov, A. I.
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p. 1806 - 1813
(2007/10/02)
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- The Kinetic Effects of Water and of Cyclodextrins on Diels-Alder Reactions. Host-Guest Chemistry. Part 18
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The rates of 19 different dienophiles with mostly cyclopentadiene have been measured in a range of solvents.Water, by comparison with methanol, is found to accelerate the cycloadditions by factors ranging from 15-7 680.While there is no simple correlation of the rate enhancement with the hydrophobicity of the substrates, a correlation can be made in the case of acrylates, which show a decreasing rate effect due to water, and with β-cyclodextrin, which is found to lead to inhibition in these and several other cases.Computer analysis of enzyme-like saturation kinetics-observed with some fumarates in the presence of β-cyclodextrin-indicates apparent binding constants for the ternary complex of ca. 102 dm3 mol-1 and catalytic kcat/ko ratios of up to 100.Heptakis-6 piperidino-β-cyclodextrin in the form of its ammonium salt leads to rate retardation in most of the cases investigated; sodium dodecylsulphate also decreases the constants. α-Cyclodextrin generates small effects, rate retardation, or in one case complete inhibition.
- Sangwan, Naresh K.,Schneider, Hans-Joerg
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p. 1223 - 1228
(2007/10/02)
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