2-Pyrrolidone
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| Template:Longitem | 49671 |
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| Density | 1.116 g/cm3[1] |
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| Template:Longitem | 2-Pyrrolidone-5-carboxylic acid |
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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
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]
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
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
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
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- ↑ a b Merck Index, 11th Edition, 8027
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External links
- Template:Replace at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
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