Unsaturated aliphatic primary amine and production method...

Details Unsaturated aliphatic primary amine and production method... Unsaturated aliphatic primary amine and production method...

C - Chemistry, Metallurgy

07

C

C07C 209/48 (2006.01) C07B 61/00 (2006.01) C07C 211/21 (2006.01)

Patent

CA 2621396

Disclosed is a process for producing an unsaturated aliphatic primary amine which can prevent the by-production of a saturated aliphatic primary amine, can yield a product having no turbidness or no precipitate, and can produce an unsaturated aliphatic primary amine having a low coagulation point with good efficiency. Also disclosed is an unsaturated aliphatic primary amine produced by the process. A process for producing an unsaturated aliphatic primary amine comprising the step of performing the hydrogen reduction of an unsaturated aliphatic nitrile having 16 to 22 carbon atoms with a hydrogenation catalyst in the presence of ammonia, wherein the hydrogen reduction is performed under the conditions where an aromatic carboxylic acid amide is added in an amount of 0.01 to 1.0 part by mass based on 100 parts by mass of the unsaturated aliphatic nitrile and the ratio of the fractional pressure of ammonia to that of hydrogen [(ammonia)/(hydrogen)] is adjusted within the range from 8/2 to 6/4; and an unsaturated aliphatic primary amine produced by the process, which has an amine conversion rate as defined by the formula (1) of 95% or higher, and has an iodine value retention rate as defined by the formula (2) of 95% or higher. [Formula 10] (1) AA Amine conversion rate (%) BB (found amine value of unsaturated aliphatic primary amine) CC (calculated amine value of the amine) [Formula 11] (2) DD Iodine value retention ratio (%) EE (iodine value of unsaturated aliphatic primary amine) ~ (molecular weight of the amine) FF (iodine value of unsaturated aliphatic nitrile) ~ (molecular weight of the nitrile)

L'invention concerne un procédé de production d'une amine primaire aliphatique insaturée qui permet de prévenir la formation de sous-produits d'amine primaire aliphatique saturée, d'obtenir un produit dépourvu de turbidité et de précipité, et de produire avec un bon rendement une amine primaire aliphatique insaturée à point de coagulation bas. L'invention concerne aussi l'amine primaire aliphatique insaturée produite à l'aide du procédé. Le procédé comporte l'étape consistant à soumettre un nitrile aliphatique insaturé comportant de 16 à 22 atomes de carbones à une réduction d'hydrogène avec un catalyseur d'hydrogénation, en présence d'ammoniac, la réduction d'hydrogène étant mise en oeuvre dans des conditions permettant l'addition d'un amide d'acide carboxylique à raison de 0,01 à 1,0 parties en poids pour 100 parties en poids du nitrile aliphatique insaturé, et le rapport entre la pression partielle de l'ammoniac et celle de l'hydrogène [(ammoniac)/(hydrogène)] est réglée de manière à se situer entre 8/2 et 6/4. L'invention concerne aussi l'amine primaire aliphatique insaturée obtenue à l'aide du procédé, qui présente un taux de conversion d'amine, défini par la formule (1), supérieur ou égal à 95 %, et un taux de maintien d'indice diode, défini par la formule (2), supérieur ou égal à 95 %.

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