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]
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| Preferred IUPAC name
Pyrrolidin-2-one | |||
Other names
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| Identifiers | |||
3D model (JSmol)
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| ECHA InfoCard | 100.009.531 | ||
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PubChem CID
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CompTox Dashboard (EPA)
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| 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: | |||
 [2]
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| Warning | |||
| H319[2] | |||
| P305+P351+P338[2] | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 129 °C (264 °F) (open cup)[1] 138 °C (280 °F) (closed cup)[2] | ||
| Related compounds | |||
Related compounds
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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).
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2-Pyrrolidone itself and it various derivatives, especially N-methylpyrrolidone, have a variety of industrial uses.
Production
edit2-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]
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
edit2-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
edit2-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- ^ a b Merck Index, 11th Edition, 8027
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
External links
edit- Pyrrolidinones at the U.S. National Library of Medicine Medical Subject Headings (MeSH)