N-Vinylcaprolactam Chemical Properties

Melting point:

35-38 °C (dec.) (lit.)

Boiling point:

128 °C/21 mmHg (lit.)

Density 

1.029 g/mL at 25 °C (lit.)

vapor pressure 

3Pa at 20℃

refractive index 

1.

Flash point:

214 °F

storage temp. 

2-8°C

form 

powder to lump to clear liquid

pka

-0.91±0.20(Predicted)

color 

White or Colorless to Light orange to Yellow

Odor

Faint specific odor

Water Solubility 

Soluble in water (partly).

FreezingPoint 

34

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChI

1S/C8H13NO/c1-2-9-7-5-3-4-6-8(9)10/h2H,1,3-7H2

InChIKey

JWYVGKFDLWWQJX-UHFFFAOYSA-N

SMILES

C=CN1CCCCCC1=O

LogP

1.2 at 25℃

CAS DataBase Reference

2235-00-9(CAS DataBase Reference)

EPA Substance Registry System

2H-Azepin-2-one, 1-ethenylhexahydro- (2235-00-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41-36/37/38

Safety Statements 

26-39-36

WGK Germany 

3

TSCA 

TSCA listed

HS Code 

29337900

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Sens. 1
STOT RE 1

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Vinylcaprolactam Usage And Synthesis

Chemical Properties

N-Vinylcaprolactam is a pale yellow crystalline solid. It is a versatile reactive diluent for free radical radiation curable coatings, inks, and adhesives which are used on a wide variety of substrates such as flooring, paper, plastics and more.

Uses

N-Vinyl-e-caprolactam (cas# 2235-00-9) is a compound useful in organic synthesis.

benefits

N-Vinylcaprolactam serves as a diluent when coating plastics, as it softens the surface thereby aiding adhesion of the cured film. The monomer N-Vinyl caprolactam provides fast curing and low viscosity and is relatively safe in radiation curable ink. Commercial uses of this chemical have also been reported to include use as a kinetic inhibitor for natural gas hydrates when integrated as a polymer.

General Description

N-Vinylcaprolactam (NVCL) is an organo-soluble amphiphilic material that is soluble in solvents like benzene, isobutanol, and isopropanol. It can be used in the preparation of poly(NVCL) by free-radical polymerization at a temperature higher than its melting point.

Flammability and Explosibility

Non flammable

Safety Profile

The acute oral LD50 of vinylcaprolactam was determined to be 1114mg/kg in rats. The acute oral LD50 was determined to be 1236mg/kg in male rats and 1049mg/kg in female rats.

Synthesis

Caprolactam and potassium hydroxide were added proportionally in a four-necked flask, evacuated and heated up to 140 ??, and the potassium salt of caprolactam was produced while dehydrating. The caprolactam raw material, caprolactam potassium salt, polymerization inhibitor and co-catalyst crown ether were added into a four-necked flask heated by an electric heating jacket or a tower glass reactor (500 mL) with a diameter of 50 mm and a height of 300 mm, and the material was stirred by a magnetic stirrer in combination with a nitrogen air stream, and the mixture of nitrogen and acetylene from the steel cylinder was measured by a mass flow meter. When the material was warmed up to the specified temperature of 90-170 ??, acetylene was passed into the reactor, bubbled, maintained for 2-8 h, cooled down, stopped the gas, and unloaded. The obtained material, first simple distillation, and then after distillation separation that is the pure N-vinyl caprolactam.

Potential Exposure

Consumer: N-vinylcaprolactam is used as a reactive diluent for UV-coatings, -inks and -adhesives as well as a building block for synthesis of paper coatings and will be almost exclusively incorporated into the polymer matrix within consumer products. Therefore, due to the extremely low levels of residual monomer present in consumer products, exposure and subsequent risk is unlikely.
Worker: In industrial settings, N-vinylcaprolactam is manufactured and handled primarily in closed processes which limit exposure. Based on good manufacturing processes and industrial hygiene the occupational health risk associated with N-vinylcaprolactam is low.
Environmental Exposures: N-vinylcaprolactam is inherently biodegradable and has low potential for bioaccumulation. It is soluble in water and has low potential for volatilization. Based on its physical and chemical properties, if n-vinyl caprolactam was released into the environment, it is expected to partition between water and soil. Volatilization from water surfaces is not expected.

Purification Methods

Distil it under vacuum and with 0.0015% of 4-tert-butylcatechol as stabilizer. [Beilstein 21 III/IV 3207.]

N-Vinylcaprolactam(2235-00-9)Related Product Information

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• NYLON 6
• N-Methylcaprolactam
• Caprolactam
• poly-N-vinylcaprolactam
• Polyquaternium 46, Poly[(3-methyl-1-vinylimidazolium methyl sulfate)-co-(1-vinylcaprolactam)-co-(1-vinylpyrrolidone)]
• ETIZOLAM
• dimethylaminoethyl methacrylate/ PVP/ N-vinylcaprolactam
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• 3-(PYRIDIN-3-YLCARBONYL)-1-VINYLAZEPAN-2-ONE
• 3-(PYRIDINE-4-CARBONYL)-1-VINYL-AZEPAN-2-ONE
• 3-BENZOYL-1-VINYL-AZEPAN-2-ONE
• 3-(2-PHENYL-QUINOLINE-4-CARBONYL)-1-VINYL-AZEPAN-2-ONE
• 1-[1-(2-BROMO-PHENYL)-VINYL]-AZEPAN-2-ONE