| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name Pyrrolidin-2-one | |||
Other names
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| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.009.531 | ||
| EC Number |
| ||
| 49671 | |||
| UNII | |||
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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] | |||
| 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 | 2-Pyrrolidone-5-carboxylic acid | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
2-Pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is anorganic compound consisting of a 5-memberedlactam, 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, especiallyN-methylpyrrolidone, have a variety of industrial uses.
2-Pyrrolidone is produced industrially almost exclusively by treating aqueousgamma-butyrolactone withammonia at a temperature of 250–290 °C and pressures ranging from 0.4–1.4 MPa over solidmagnesium silicate catalysts.[3]
The reaction is carried out in atubular reactor which is packed with the solidcatalyst. The latter is arranged as a fixed bed and the reaction is carried out in the vapor phase. Productyields of 75–85% are reached. After subsequentdistillation and purification, the desired 2-pyrrolidone is obtained with a purity of 99.5%.[3]
Alternative routes include the catalytic or electrochemical reduction ofsuccinimide, thecarbonylation ofallylamine,[4] thehydrogenation ofsuccinonitrile under hydrolytic conditions, and the reaction ofmaleic orsuccinic 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 areBASF and ISP (International Speciality Products, nowAshland Inc.).[3]
2-Pyrrolidone itself is used in inkjet cartridges.[5]
A variety of pharmaceutical drugs are 2-pyrrolidonederivatives, includingcotinine,doxapram,povidone, andethosuximide, and theracetams.
The chemical is an intermediate in the production of thepolyvinylpyrrolidone precursorvinylpyrrolidone.[3]
2-Pyrrolidone is relatively innocuous with anLD50 in the range of grams per kilogram (rats, oral). It is not mutagenic.[3] It can be an eye irritant.[5]
