N-Vinylpyrrolidone

N-Vinylpyrrolidone
Skeletal formula
2-Pyrrolidone
Ball-and-stick model
Names
Preferred IUPAC name
1-Ethenylpyrrolidin-2-one
Other names
1-Vinylpyrrolidin-2-one
1-Ethenyl-2-pyrrolidone
N-Ethenyl-2-pyrrolidone
N-Vinyl-2-pyrrolidone
1-Vinyl-2-pyrrolidone
N-Vinylbutyrolactam
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.637 Edit this at Wikidata
UNII
  • InChI=1S/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2 checkY
    Key: WHNWPMSKXPGLAX-UHFFFAOYSA-N checkY
  • InChI=1/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2
    Key: WHNWPMSKXPGLAX-UHFFFAOYAI
  • O=C1N(C=C)CCC1
Properties
C6H9NO
Molar mass 111.144 g·mol−1
Density 1.04 g/cm3[1]
Melting point 13–14 °C (55–57 °F; 286–287 K)
Boiling point 92–95 °C (198–203 °F; 365–368 K)[1] 11 mmHg
Vapor pressure 0.1 mmHg (24 °C)[1]
1.512[1]
Hazards
Flash point 95 °C (203 °F; 368 K)
685 °C (1,265 °F; 958 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Vinylpyrrolidone (NVP) is an organic compound consisting of a 5-membered lactam ring linked to a (2 carbon) vinyl group. It is a colorless liquid although commercial samples can appear yellowish.

It is produced industrially by vinylation of 2-pyrrolidone, i.e. the base-catalyzed reaction with acetylene.[2] It is the precursor to polyvinylpyrrolidone (PVP), an important synthetic material. The NVP monomer is commonly used as a reactive diluent in ultraviolet and electron-beam curable polymers applied as inks, coatings or adhesives.[2]

Synthesis

Starting from γ-Butyrolactone, 2-pyrrolidone is synthesized by treatment with ammonia.[3] Subsequently, acetylene is used to introduce the vinyl group.[2][4]

Synthesis of N-vinyl-2-pyrrolidone
Synthesis of N-vinyl-2-pyrrolidone

See also

References

  1. ^ a b c d "1-Vinyl-2-pyrrolidinone". Sigma-Aldrich.
  2. ^ a b c Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang"2-Pyrrolidone, R. (2011). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_457.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: numeric names: authors list (link)
  3. ^ Teodorescu, Mirela; Bercea, Maria (23 June 2015). "Poly(vinylpyrrolidone) – A Versatile Polymer for Biomedical and Beyond Medical Applications". Polymer-Plastics Technology and Engineering. 54 (9): 923–943. doi:10.1080/03602559.2014.979506.
  4. ^ Pässler, Peter; Hefner, Werner; Buckl, Klaus; Meinass, Helmut; Meiswinkel, Andreas; Wernicke, Hans-Jürgen; Ebersberg, Günter; Müller, Richard; Bässler, Jürgen; Behringer, Hartmut; Mayer, Dieter (2008). "Acetylene Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_097.pub3. ISBN 3527306730.