Structure via PubChem · Public domain (PubChem)
laurolactam
Sign in to saveLaurolactam 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.
Chemical data
- Formula
- C12H23NO
- Molecular weight
- 197.32 g/mol
- IUPAC name
- azacyclotridecan-2-one
- SMILES
- C1CCCCCC(=O)NCCCCC1
- InChIKey
- JHWNWJKBPDFINM-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 197.178
Show 3 more facts
- chemical formula
- C₁₂H₂₃NO
- canonical SMILES
- C1CCCCCC(=O)NCCCCC1
- isomeric SMILES
- C1CCCCC/C(=N\CCCCC1)/O
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Synthesis
- Properties
- Uses
- Drug Use
- References
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.
==Synthesis== 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.center|500px|Formation of laurolactam
Excerpted from Wikipedia’s “laurolactam” article, available under the CC BY-SA 4.0 licence.