Hydroxylamine → Benzamide

Participants

Reaction Steps

The reaction was carried out in a similar manner to Example 1 except that the rearrangement solvent was replaced with benzonitrile. As the passage of operation time benzamidoxime was detected which was generated by reaction of benzonitrile contained in the recycled liquid to the oxime-forming step with hydroxylamine. As this progress, an amount of cyclododecanone increased due to a shortage of hydroxylamine to be used for the oxime-formation reaction. Although the yield of laurolactam until the rearrangement step was initially 96.0%, the yield declined to 82% as a result of the operation after 8 hours. In addition, benzonitrile was hydrolyzed to yield benzamide and the like during the treatment with sodium hydroxide, and the purity of laurolactam obtained by distillation was 85%.

Provenance & Evidence