Structure via PubChem · Public domain (PubChem)
caprolactam
Sign in to saveAlso known as Aminocaproic lactam, epsilon-Caprolactam, Hexahydro-2H-azepin-2-one, 2-Oxohexamethyleneimine, 6-caprolactam, 2-ketohexamethyleneimine, 2-oxohexamethylenimine, Kaprolaktam
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used to make nylon 6 filament, fiber, and plastics.
Chemical data
- Formula
- C6H11NO
- Molecular weight
- 113.16 g/mol
- IUPAC name
- azepan-2-one
- SMILES
- C1CCC(=O)NCC1
- InChIKey
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N
- XLogP
- -0.1
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,728 papers- Caprolactam.IARC monographs on the evaluation of carcinogenic risks to humans · 1999
- Biologic activity of epsilon-caprolactam.Critical reviews in toxicology · 1984
- Caprolactam and nylon 6.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Artificial Caprolactam-Specific Riboswitch as an Intracellular Metabolite Sensor.ACS synthetic biology · 2019
- Epsilon-Caprolactam.British journal of industrial medicine · 1954
via PubMed
Wikidata facts
- Mass
- 113.084
Show 13 more facts
- chemical formula
- C₆H₁₁NO
- Commons category
- Caprolactam
- NIOSH Pocket Guide ID
- 0097
- density
- 1.01
- melting point
- 69.3
- boiling point
- 270
- flash point
- 282
- solubility
- 53
- lower flammable limit
- 1.4
- upper flammable limit
- 8
- vapor pressure
- 0.00000008
- canonical SMILES
- C1CCC(=O)NCC1
- ionization energy
- 9.07
Sources (3)
via Wikidata · CC0
~4 min read
Article
5 sectionsContents
- Synthesis and production
- Uses
- Safety
- Climate impact
- References
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used to make nylon 6 filament, fiber, and plastics.
==Synthesis and production== Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam. World demand for caprolactam was estimated to reach five million tons per year for 2015. 90% of caprolactam produced is used to make filament and fiber, 10% for plastics, and a small amount is used as a chemical intermediate. Due to its commercial significance, many methods have been developed for the production of caprolactam. It was estimated that 90% of all caprolactam is synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam (3): 350px|The Beckmann Rearrangement