2-Pyrrolidone

changed changed 477215634 2-Pyrrolidone Structural formula of 2-pyrrolidone.svg skin-invert-image Structural formula of 2-Pyrrolidone Pyrrolidone-3D-vdW.png bg-transparent Pyrrolidin-2-one 2-Pyrrolidone 2-Pyrrolidinone Aminobutyrolactam Butyrolactam γ-Butyrolactam 2-Ketopyrrolidine correct chemspider 11530 49671 12025 1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6) HNJBEVLQSNELDL-UHFFFAOYAP correct EBI 210-483-1 276849 correct chemspider 1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6) correct chemspider HNJBEVLQSNELDL-UHFFFAOYSA-N correct CAS 616-45-5 correct EBI 36592 correct FDA KKL5D39EOL O=C1NCCC1 4 7 1 1 1.116 g/cm3Merck Index, 11th Edition, 8027 25 490258 616-45-5 2-Pyrrolidone 16 March 2020 245 exclamation mark Warning 319 305+351+338 2 1 0 129 C F (open cup)138 C F (closed cup) 2-Pyrrolidone-5-carboxylic acid 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. 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. Albrecht Ludwig Harreus R. Backes J.‐O. Eichler R. Feuerhake C. Jäkel U. Mahn R. Pinkos R. Vogelsang 2011 10.1002/14356007.a22_457.pub2 2‐Pyrrolidone 978-3527306732 400px|upright=2.5|frameless|class=skin-invert-image|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%. Alternative routes include the catalytic or electrochemical reduction of succinimide, the carbonylation of allylamine,10.1002/14356007.a01_425 Allyl Compounds Ullmann's Encyclopedia of Industrial Chemistry 2000 Krähling Ludger Krey Jürgen Jakobson Gerald Grolig Johann Miksche Leopold 978-3-527-30385-4 the hydrogenation of succinonitrile under hydrolytic conditions, and the reaction of maleic or succinic anhydride in aqueous ammonia with Pd–Ru-catalysts. 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.). Uses 2-Pyrrolidone itself is used in inkjet cartridges.Safety Data Sheet http://www.hp.com/hpinfo/globalcitizenship/environment/productdata/Countries/gb/ij_ch562series_gb_eng_v14.pdf HP website HP 11 October 2014 PDF 7 October 2014 16 October 2014 https://web.archive.org/web/20141016193050/http://www.hp.com/hpinfo/globalcitizenship/environment/productdata/Countries/gb/ij_ch562series_gb_eng_v14.pdf dead A variety of pharmaceutical drugs are 2-pyrrolidone derivatives, including cotinine, doxapram, and ethosuximide, and the racetams. The chemical is an intermediate in the production of the polyvinylpyrrolidone precursor vinylpyrrolidone. Safety 2-Pyrrolidone is relatively innocuous with an in the range of grams per kilogram (rats, oral). It is not mutagenic. It can be an eye irritant. References External links Pyrrolidinones Category:Amide solvents Category:Human drug metabolites