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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.
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| Names | |||
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| 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) |
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| ChemSpider | |||
| ECHA InfoCard | 100.001.637 | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| 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] | ||
Refractive index (nD) |
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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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]
Starting from γ-Butyrolactone, 2-pyrrolidone is synthesized by treatment with ammonia.[3] Subsequently, acetylene is used to introduce the vinyl group.[2][4]
- Methylpyrrolidone (NMP)
- 2-Pyrrolidone (2-Py)
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