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2-Pyrrolidone

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2-Pyrrolidone
Structural formula of 2-Pyrrolidone
Structural formula of 2-Pyrrolidone
Names
Preferred IUPAC name Pyrrolidin-2-one
Other names
  • 2-Pyrrolidone
  • 2-Pyrrolidinone
  • Aminobutyrolactam
  • Butyrolactam
  • γ-Butyrolactam
  • 2-Ketopyrrolidine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.531 Edit this at Wikidata
EC Number
  • 210-483-1
Gmelin Reference 49671
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)Key: HNJBEVLQSNELDL-UHFFFAOYSA-N
  • InChI=1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)Key: HNJBEVLQSNELDL-UHFFFAOYAP
SMILES
  • O=C1NCCC1
Properties
Chemical formula C4H7NO
Molar mass 85.106 g·mol
Density 1.116 g/cm
Melting point 25 °C (77 °F; 298 K)
Boiling point 245 °C (473 °F; 518 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H319
Precautionary statements P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Flash point 129 °C (264 °F) (open cup)
138 °C (280 °F) (closed cup)
Related compounds
Related compounds 2-Pyrrolidone-5-carboxylic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is an organic compound consisting of a 5-membered lactam, making it the simplest γ-lactam. It is a colorless liquid that is miscible with water and most common organic solvents.

2-Pyrrolidone itself and it various derivatives, especially N-methylpyrrolidone, have a variety of industrial uses.

Production

2-Pyrrolidone is produced industrially almost exclusively by treating aqueous gamma-butyrolactone with ammonia at a temperature of 250–290 °C and pressures ranging from 0.4–1.4 MPa over solid magnesium silicate catalysts.

Reaction of γ-butyrolactone with ammonia to form 2-pyrrolidone (γ-butyrolactam) and water in the presence of a solid magnesium silicate catalyst

The reaction is carried out in a tubular reactor which is packed with the solid catalyst. The latter is arranged as a fixed bed and the reaction is carried out in the vapor phase. Product yields of 75–85% are reached. After subsequent distillation and purification, the desired 2-pyrrolidone is obtained with a purity of 99.5%.

Alternative routes include the catalytic or electrochemical reduction of succinimide, the carbonylation of allylamine, the hydrogenation of succinonitrile under hydrolytic conditions, and the reaction of maleic or succinic anhydride in aqueous ammonia with Pd–Ru-catalysts.

In 2010, the worldwide demand for 2-pyrrolidone was estimated to be 32.000 t. Important manufacturers of 2-pyrrolidone are BASF and ISP (International Speciality Products, now Ashland Inc.).

Uses

2-Pyrrolidone itself is used in inkjet cartridges.

A variety of pharmaceutical drugs are 2-pyrrolidone derivatives, including cotinine, doxapram, povidone, and ethosuximide, and the racetams.

The chemical is an intermediate in the production of the polyvinylpyrrolidone precursor vinylpyrrolidone.

Safety

2-Pyrrolidone is relatively innocuous with an LD50 in the range of grams per kilogram (rats, oral). It is not mutagenic. It can be an eye irritant.

References

  1. ^ Merck Index, 11th Edition, 8027
  2. ^ Record of 2-Pyrrolidone in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 16 March 2020.
  3. ^ Albrecht Ludwig Harreus; R. Backes; J.‐O. Eichler; R. Feuerhake; C. Jäkel; U. Mahn; R. Pinkos; R. Vogelsang (2011). "2‐Pyrrolidone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_457.pub2. ISBN 978-3527306732.
  4. Krähling, Ludger; Krey, Jürgen; Jakobson, Gerald; Grolig, Johann; Miksche, Leopold (2000). "Allyl Compounds". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_425. ISBN 978-3-527-30385-4.
  5. ^ "Safety Data Sheet" (PDF). HP website. HP. 7 October 2014. Archived from the original (PDF) on 16 October 2014. Retrieved 11 October 2014.

External links

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