Caprolactam

Title: Caprolactam
CAS Registry Number: 105-60-2
CAS Name: Hexahydro-2H-azepin-2-one
Additional Names: e-caprolactam; 2-oxohexamethylenimine; 2-ketohexamethylenimine; aminocaproic lactam
Molecular Formula: C6H11NO
Molecular Weight: 113.16
Percent Composition: C 63.68%, H 9.80%, N 12.38%, O 14.14%
Literature References: Prepn: Wallach, Ann. 312, 187 (1900); 343, 43 (1905); Ruzicka et al., Helv. Chim. Acta 4, 477 (1921); Eck, Marvel, J. Biol. Chem. 106, 387 (1934); Marvel, Eck, Org. Synth. coll. vol. II, 371 (1943); Lazier, Rigby, US 2234566 (1941 to du Pont); Schlack, US 2249177 (1941 to I. G. Farben); DE 739953 (1943); DE 745224 (1943); P. Smith, J. Am. Chem. Soc. 70, 320 (1948); E. Schmitz et al., J. Prakt. Chem. 319, 274 (1977). Environmentally benign synthesis from cyclohexanone: J. M. Thomas, R. Raja, Proc. Natl. Acad. Sci. USA 102, 13732 (2005). Purification: Kampschmidt, US 2786052 (1957 to Stamicarbon N. V.). Stabilization with alkalies: Indest et al., US 2884414 (1959 to Vereinigte Glanzstoff-Fabriken). Toxicity study: H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969). Reviews: CIOS Repts. no. 22 and 31, File XXXIII/Synthetic Fiber Developments in Germany, parts I & II; K. Kahr et al. in Ullmanns Encyklopädie der technischen Chemie vol. 9, E. Bartholome et al., Eds. (Verlag Chemie, Weinheim, 4th ed., 1975) pp 96-114.
Properties: Hygroscopic leaflets from petr ether, mp 70°. d475 (liq) 1.02. bp50 180°; bp3 100°. Viscosity (78°): 9 cP. Flash pt, open cup: 257°F (125°C). Freely sol in water, methanol, ethanol, ether, tetrahydrofurfuryl alcohol, dimethylformamide. Also sol in chlorinated hydrocarbons, cyclohexene, petroleum fractions. A 70% aq soln has d425 1.05; nD31 1.4965; nD40 1.4935. LD50 orally in rats: 2.14 g/kg (Smyth).
Melting point: mp 70°
Boiling point: bp50 180°; bp3 100°
Flash point: Flash pt, open cup: 257°F (125°C)
Index of refraction: nD31 1.4965; nD40 1.4935
Density: d475 (liq) 1.02; d425 1.05
Toxicity data: LD50 orally in rats: 2.14 g/kg (Smyth)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; epistaxis; dermatitis, skin sensitization; asthma; irritability, confusion, dizziness, headache; abdominal cramps, diarrhea, nausea, vomiting; liver and kidney injury. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 50.
Use: Manuf of synthetic fibers of the polyamide type (Perlon); solvent for high mol wt polymers; precursor of nylon-6, q.v.
Capromab Caproyl Chloride Caprylene Caprylic Acid Caprylic Aldehyde

Caprolactam
Caprolactam-2D-skeletal.png Caprolactam-3D-vdW.png
Identifiers
CAS number 105-60-2 YesY
PubChem 7768
ChemSpider 7480 YesY
UNII 6879X594Z8 YesY
EC number 203-313-2
KEGG C06593 YesY
ChEBI CHEBI:28579 YesY
ChEMBL CHEMBL276218 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H11NO
Molar mass 113.16 g/mol
Appearance white solid
Density 1,01 g/cm3
Melting point 69,2 °C
Boiling point 270,8°C at 1013.25 hPa
Solubility in water 4560 g/L (20 °C)
Hazards
R-phrases R20, R22, R36/37/38
Flash point 125 °C; 257 °F; 398 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam or a cyclic amide of caproic acid. Approximately 4.5 billion kilograms are produced annually. Caprolactam is the precursor to Nylon 6, a widely used synthetic polymer.[1]