Hydroxylamine → Benzamide

HRID 1876766Notes

Reaction equation

HRID 1876766 reaction equation
C1(=O)CCCCCCCCCCC1.NO.[C:16]1(=[O:29])[NH:28]CCCCC[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C1C=CC=CC=1>[C:16]([NH2:28])(=[O:29])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 13246CyclododecanoneHCID 13690Laurolactam

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

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%.

Workup

  1. customa result of the operation after 8 hours

Sources & evidence

ORD record
ord-ed4bb19ad6f74a9fab10295b1eacaf40
Source dataset
uspto-grants-2012_11
Patent number
US08309714B2

Reaction notes

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