- STEREOCHIMIE-LV. ETUDE CINETIQUE DE L'HYDROCYANATION D'ENONES CYCLIQUES
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Kinetics of hydrocyanation of various enones are reported.The different behaviour of testosterone and 19-nor-testosterone towards hydrocyanation is explained by a slower partial rate factor on the α-face of testosterone.
- Agami, C.,Fadlallah, M.,Levisalles, J.,Cayzergues, P.
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- PROCESS FOR MANUFACTURING AN ALKYL SUBSTITUTED CYCLOHEXANECARBONITRILE
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A process for manufacturing an alkyl substituted cyclohexanecarbonitrile, said process comprising the following steps: - reaction of cyanoisophorone with an organometallic compound comprising an alkyl group in order to transform the ketone moiety into its corresponding alcohol; - reduction of the alcohol in order to obtain the alkyl substituted cyclohexanecarbonitrile.
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Page/Page column 8-9
(2021/03/19)
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- Method for preparing IPDI (isophorone diisocyanate)
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The invention discloses a method for preparing IPDI (isophorone diisocyanate). The method comprises the following steps: (1) isophorone and hydrogen cyanide are subjected to a reaction in the presenceof a catalyst to obtain isophorone nitrile; (2) isophorone nitrile obtained in step (1), ammonia and hydrogen are subjected to a reaction in the presence of a catalyst to obtain isophorone diamine; (3) isophorone diamine is subjected to a phosgenation reaction to obtain IPDI, wherein the content of impurities containing secondary amine groups in isophorone diamine subjected to the phosgenation reaction in step (3) is smaller than or equal to 0.5wt%, preferably smaller than or equal to 0.3wt%, and more preferably smaller than or equal to 0.1wt%. By means of the method, content of hydrolyzed chlorine in the IPDI product can be effectively reduced, the yellowing resistance of the product is effectively improved, and the harm that downstream products are unqualified due to existence of hydrolyzed chlorine in the product is reduced.
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Paragraph 0076-0078
(2019/06/13)
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- Method for continuously preparing isophorone nitrile
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The invention discloses a method for continuously preparing isophorone nitrile. Existing tubular homogeneous phase continuous synthesis method and fixed bed continuous synthesis method respectively cause side reaction due to nonuniform HCN concentration. The method disclosed by the invention is characterized in that isophorone and hydrocyanic acid are heated for reaction in presence of an alkaline catalyst to obtain isophorone nitrile, the used reactor is a multi-kettle series continuous operation type reactor comprising more than or equal to 7 kettles, the used alkaline catalyst is alcoholic solution of alkali metal cyanide, the used reactant hydrocyanic acid is isophorone solution of hydrocyanic acid, the reactant isophorone is added from a first kettle, and the isophorone solution of hydrocyanic acid and the alkaline catalyst are added in a multi-kettle continuous dropwise adding manner. The method disclosed by the invention has the advantages of continuous and stable operation, good procedural security, high reaction yield, recyclable solvent and catalysts and clean production process and is applicable to industrial production.
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Paragraph 0043; 0044; 0045
(2016/12/22)
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- A method for improved processing trimethylcyclohexen-2-one-1 nitrile reaction solution
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The invention provides a method for treatment of a reaction solution obtained in preparation of isophoronenitrile from raw materials, namely isophorone and hydrocyanic acid under the catalysis of an alkaline catalyst. By adopting a two-step neutralization method, the reaction solution of isophoronenitrile is relatively stable, the influence of a salt produced in a neutralization process on a subsequent separation system is avoided and the stability in operation of a device is increased; furthermore, decomposition and polymerization reactions of isophoronenitrile and the reaction speed of polymerization of isophorone in the neutralization process and subsequent rectification separation of the reaction solution of isophoronenitrile are greatly reduced, the product yield is further improved, the unit consumption of materials is reduced by above 5%, the solid and waste content in a high polymer is reduced by above 80%, and a series of production, safety, environmental production and other problems caused by production of hydrocyanic acid in a rectification system are avoided.
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Paragraph 0045-0052
(2017/02/23)
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- PROCESS FOR PREPARING 3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE
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The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or, in abbreviated form, IPDA, by: I. preparation of isophorone by catalyzed aldol condensations with acetone as reactant; II. reaction of isophorone with HCN to form isophoronenitrile (IPN, 3-cyano-3,5,5-trimethylcyclohexanone); III. catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminative hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, hereinafter called isophoronenitrile or, in abbreviated form, IPN, to give the isophoronediamine.
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Paragraph 0215 - 0231
(2013/10/07)
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- COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFLUENZA
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A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R4 and Ar are as defined in description and in claims, can be used as a medicament.
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Page/Page column 35
(2011/09/14)
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- COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFLUENZA
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A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R4 and Ar are as defined in description and in claims, can be used as a medicament.
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Page/Page column 35
(2011/09/14)
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- COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFLUENZA
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A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R4 and Ar are as defined in description and in claims, can be used as a medicament.
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Page/Page column 20
(2011/08/22)
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- IMPROVED NEUTRALIZATION OF ISOPHORONE NITRILE SYNTHESIS PRODUCTS
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The invention relates to a method for producing 3-cyano-3,5,5- trimethylcyclohexanone (isophorone nitrile) by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst. A special sulfonic acid or a special carboxylic acid is added to the resulting raw isophorone nitrile product which is then distilled. The invention further relates to the use of a special sulfonic acid or a special carboxylic acid as a neutralizing agent prior to distilling a raw isophorone nitrile product which is obtained by reacting isophorone with hydrogen cyanide in the presence of a base as a catalyst in order to prevent precipitations during neutralization of the base used as a catalyst with an acid.
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- CaO-catalyzed preparation of isophoronenitrile
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The present invention describes a process for preparing isophoronenitrile by adding HCN to isophorone. The catalyst used is CaO which has a BET surface area of >1.5 m2/g. The use of such a catalyst achieves high yields and selectivities.
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- A new route for the convenient synthesis of 3-aminomethyl-3,5,5-trimethyl- cyclohexanol
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There has been a considerable chemical and biological interest in influenza fusion inhibitors namely, 3-aminomethyl-3,5,5-trimethyl-cyclohexanol 5. This compound has been identified as an important inhibitor of influenza virus fusion derivative and a potent and effective surrogate for the quinolizidine moiety. A new convenient route for the synthesis of 5 and for two new intermediates 1,3,3-trimethyl-5-oxo-cyclohexane-carboxylic acid amide 3 and 5-hydroxy-1,3,3-trimethyl-cyclohexane-carboxylic acid amide 4.
- Pandey, Satish C.,Singh, Sudhir S.,Patro, Balaram,Ghosh, Anil C.
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p. 2705 - 2707
(2007/10/03)
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- Preparation of 3-cyano-3, 5, 5-trimethylcyclohexanone
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In a process for preparing 3-cyano-3,5,5-trimethylcyclohexanone by reacting isophorone with hydrogen cyanide at from 80 to 220° C. in the presence of a catalyst, the reaction is carried out in the presence of the betaine 1,3-dimethylimidazolium-4-carboxylate.
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- Synthesis of 3H-labeled 2-hydroxy-N-[(1,3,3-trimethyl-[4,5,6-3H]cyclohexyl)methyl]-5-azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor
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Synthesis of 3H-labeled 2-hydroxy-N-[(1,3,3-trimethyl-[4,5,6-3H]cyclohexyl)methyli]-5-azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor, is reported. Tritiation of a mixture of N-(t-butoxycarbonyl)-1,3,3-trimethylcyclohex-4 (or 5)-enylmethylamine via T2 and Pd/C, followed by coupling of the deprotected tritiated amine with acetyl 5-azidosalicylic acid chloride yielded the penultimate product. Subsequent deprotection and normal phase HPLC purification yielded the target compound with a radiochemical purity > 99% and a specific activity of 63 Ci/mmol.
- Dischino, Douglas D.,Cianci, Christopher,Krystal, Mark,Meanwell, Nicholas A.,Morimoto, Hiromi,Pearce, Bradley C.,Williams, Philip,Yu, Kuo-Long
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p. 965 - 974
(2007/10/03)
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- Preparaion of 3.cyano-3,5,5-trimethylcyclohexanone
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A process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone by the reaction of isophorone with hydrogen cyanide in the presence of quaternary ammonium catalysts at temperatures ranging from 80° to 180° C. and pressures ranging from 0.5 to 20 bar, in which the ammonium catalysts used are salts of the general formula I STR1 in which R1, R2, R3, R4 denote C1 -C18 alkyl, C5 -C8 cycloalkyl, aryl, C7 -C18 aralkyl or C2 -C18 hydroxyalkyl and X denotes HCO3 or STR2 with the proviso that R4 stands for C1 -C8 alkyl when X is STR3
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- Process for producing amines
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A process is disclosed for producing an amine by carrying out a reductive amination of a cyclic ketone or by carrying out a reduction of an imino derivative of a cyclic ketone to the corresponding amine which process is characterized in using a cobalt catalyst containing a carbonate of an alkaline earth metal and/or lanthanum oxide.
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- Process for the preparation of 3-aminomethyl-3,5,5-trialkylcyclohexylamine
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A process for the preparation of a 3-aminomethyl-3,5,5-trialkylcyclohexylamine, which comprises hydrogenating 3-cyano-3,5,5-trialkylcyclohexylamine in the presence of ammonia and a ruthenium-cobalt catalyst.
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- Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone
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A method for the production of 3-cyano-3,5,5-trimethyl cyclohexanone by the reaction of isophorone with hydrogen cyanide in the presence of a quaternary ammonium salt or quaternary phosphonium salt and a basic compound as a catalyst in the form dissolved or dispersed in water or in the absence of water, which method comprises effecting said reaction by using said quaternary ammonium salt or quaternary phosphonium salt in an amount in the range of from 0.001 to 0.1 mol per mol of isophorone and said basic compound and in an amount in the range of from 0.5 to 3.0 mols per mol of said quaternary ammonium salt or quaternary phosphonium salt and, when water is used, using water in an amount in the range of 0.1 to 25% by weight based on the amount of isophorone and introducing hydrogen cyanidehydrocyanic acid at a ratio in the range of from 0.6 to 1.0 mol per mol of isophorone at a temperature in the range of from 90° to 140° C.
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- STEREOCHIMIE-LII. CONTROLE ORBITALAIRE DE LA STEREOCHIMIE DES REACTIONS-III EFFETS DES GROUPES β-FLUORO ET β-CYANO SUR LA STEREOCHIMIE ET LA CINETIQUE DE LA REDUCTION DE CYCLOHEXANONES PAR LE TRITERTIOBUTOXYALUMINOHYDRURE DE LITHIUM
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The respective influences of β-fluoro and β-cyano groups on the reduction of ketones by Li(t-BuO)3AlH on the stereoselectivities of the reduction with and without added cryptands, and with and without added alkyl fluoride and nitrile, were compared with ab initio calculations using the frontier orbitals of analogous carbonyl compounds to give energy values
- Agami, C.,Kazakos, A.,Levisalles, J.,Sevin, A.
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p. 2977 - 2981
(2007/10/02)
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