A two step, one pot procedure, for the preparation of methyl-9-(or 12)-aminooctadecanoate and l-hydroxy-9-(or 12)-aminooctadecane was developed. This procedure is based on the oximation followed by hydrogenation of methyl-9-oxooctadecanoate, l-hydroxy-9oxooctadecane and the C-12-0x0 isomers. For the oximation of the keto compounds (la-d) two methods were used. In the first method NH,OH.HCI as aminodonor and Et,N as HC1-acceptor has been used. One of the major problems in this reaction sequence is the formation of Et3N.HCI. Experimentally it became clear that in an one pot reaction without separation of the Et,N.HCI, the catalytic reduction of the oximes (2a-d) to their corresponding amines was inhibited. This problem could be solved by using free NH20H. In the second method free NHIOH was used for the oximation. For the catalytic reduction of the oxime derivatives mild (room temperature and 40 psi), and therefore industrial interesting, hydrogenation conditions were used.
Hydrogenierung von Methyi-9-(hydroxyimino)octadecanoat und
Derivaten bei niedriger Temperatur und Druck in ihre entsprb chenden Aminoderivate. Eine zweistufige Eintopfreaktion wurde zur Darstellung von Methyl-9(oder 12)-Aminostearinsaureester und l-Hydroxy-9(oder 12)-Aminooctadecan entwickelt. Dieser ProzeD basiert auf der Oximierung und anschlieDenden Hydrierung von Methyl-9-Oxostearinsaureester, 1-Hydroxy-9-0x0-decan und den C-12-Derivaten. Zur Oximierung der Ketokomponenten (la-d)