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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.531 Edit this at Wikidata
EC Number
  • 210-483-1
49671
UNII
  • InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6) checkY
    Key: HNJBEVLQSNELDL-UHFFFAOYSA-N checkY
  • InChI=1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
    Key: HNJBEVLQSNELDL-UHFFFAOYAP
  • O=C1NCCC1
Properties
C4H7NO
Molar mass 85.106 g·mol−1
Density 1.116 g/cm3[1]
Melting point 25 °C (77 °F; 298 K)[2]
Boiling point 245 °C (473 °F; 518 K)[2]
Hazards
GHS labelling:
GHS07: Exclamation mark[2]
Warning
H319[2]
P305+P351+P338[2]
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)[1]
138 °C (280 °F) (closed cup)[2]
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[3]

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

Production

[edit]

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.[3]

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%.[3]

Alternative routes include the catalytic or electrochemical reduction of succinimide, the carbonylation of allylamine,[4] the hydrogenation of succinonitrile under hydrolytic conditions, and the reaction of maleic or succinic anhydride in aqueous ammonia with Pd–Ru-catalysts.[3]

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.).[3]

Uses

[edit]

2-Pyrrolidone itself is used in inkjet cartridges.[5]

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.[3]

Safety

[edit]

2-Pyrrolidone is relatively innocuous with an LD50 in the range of grams per kilogram (rats, oral). It is not mutagenic.[3] It can be an eye irritant.[5]

References

[edit]
  1. ^ a b Merck Index, 11th Edition, 8027
  2. ^ a b c d e f Record of 2-Pyrrolidone in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 16 March 2020.
  3. ^ a b c d e f g 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. ^ a b "Safety Data Sheet" (PDF). HP website. HP. 7 October 2014. Archived from the original (PDF) on 16 October 2014. Retrieved 11 October 2014.
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