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C2204

Sigma-Aldrich

ε-Caprolactam

99%

Synonym(s):

epsilon-Caprolactam, 2-Oxohexamethyleneimine, Aza-2-cycloheptanone

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About This Item

Empirical Formula (Hill Notation):
C6H11NO
CAS Number:
105-60-2
Molecular Weight:
113.16
Beilstein/REAXYS Number:
106934
EC Number:
203-313-2
MDL number:
MFCD00006936
UNSPSC Code:
12352100
PubChem Substance ID:
24892472
NACRES:
NA.22

vapor pressure

<0.01 mmHg ( 20 °C)

Quality Level

200

assay

99%

form

crystals

autoignition temp.

707 °F

expl. lim.

8 %

bp

136-138 °C/10 mmHg (lit.)

mp

68-71 °C (lit.)

SMILES string

O=C1CCCCCN1

InChI

1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)

InChI key

JBKVHLHDHHXQEQ-UHFFFAOYSA-N

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Application

ε-Caprolactam can be used as a precursor for the production of nylon-6 by ring-opening polymerization.It is also microwave irradiated with ε caprolactone in the presence of an anionic catalyst to yield poly(ε caprolactam-co-ε-caprolactone).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

305.6 °F - closed cup

flash_point_c

152 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Microwave syntheses of poly (?-caprolactam-co-?-caprolactone)
Fang X, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 38(8), 1379-1390 (2000)
Design of a ?green? one-step catalytic production of ?-caprolactam (precursor of nylon-6)
Thomas JM and Raja R
Proceedings of the National Academy of Sciences of the USA, 102(39), 13732-13736 (2005)
?-Caprolactam: New by-product free synthesis routes
Dahlhoff, G, et al.
Catalysis Reviews: Science and Engineering, 43(4), 381-441 (2001)
Ibrahim I Ozturk et al.
Journal of inorganic biochemistry, 109, 57-65 (2012-03-02)
Three new antimony(III) halide complexes (SbX(3), X=Cl, Br and I) with the heterocyclic thione ω-thiocaprolactam (1-azacycloheptane-2-thione, (Hthcl)) of formulae {[SbCl(2)(μ(2)-Cl)(Hthcl)(2)](n)} (1), {[(SbBr(2)(μ(2)-Br)(Hthcl)(2))(2)]} (2) and {[(SbI(2)(μ(2)-I)(Hthcl)(2))(2)]} (3) were synthesized from the reaction of antimony(III) halides with ω-thiocaprolactam in 1:2 stoichiometry. The
Shaohua Jiang et al.
ACS applied materials & interfaces, 4(5), 2597-2603 (2012-05-03)
The use of nylon-6 electrospun nanofiber mats as reinforcement with synergistic effect in tensile strength and toughness for melamine-formaldehyde (MF) resin is highlighted in this article. Interestingly, there was a drastic effect of the wetting procedure of reinforcing fiber mat
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