2-Pyrrolidone

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

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	616-45-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:36592 Y
ChEMBL	ChEMBL276849 Y
ChemSpider	11530 Y
ECHA InfoCard	100.009.531
EC Number	210-483-1
Gmelin Reference	49671
PubChem CID	12025
UNII	KKL5D39EOL Y
CompTox Dashboard (EPA)	DTXSID8027246
InChI InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6) Y Key: HNJBEVLQSNELDL-UHFFFAOYSA-N Y 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−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:
Pictograms	[2]
Signal word	Warning
Hazard statements	H319[2]
Precautionary statements	P305+P351+P338[2]
NFPA 704 (fire diamond)	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 YN ?) Infobox references

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]