Laurolactam

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Laurolactam is an organic compound from the group of macrocyclic lactams. Laurolactam is mainly used as a monomer in engineering plastics, such as nylon-12 and copolyamides. Although a derivative of 12-aminododecanoic acid, it is made from cyclododecatriene. The triene is hydrogenated to the saturated alkane, cyclododecane. For the production of laurolactam, cyclododecane is oxidized with air or oxygen in the presence of boric acid and transition metal salts (e.g. cobalt(II) acetate), obtaining a mixture of cyclododecanol and cyclododecanone. This mixture is quantitatively dehydrogenated on a copper contact catalyst to cyclododecanone and this reacted with hydroxylamine to cyclododecanone oxime. The oxime is rearranged to laurolactam in a Beckmann rearrangement in the presence of a strong acid. An alternative process is the photonitrosation of cyclododecane with nitrosyl chloride in the presence of anhydrous hydrogen chloride. The resulting cyclododecanone oxime is extracted with concentrated sulfuric acid and rearranged to laurolactam by heating to 160 °C. The overall yield (photonitrogenation + Beckmann rearrangement) is up to 93%.