2-Pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

consisting of a 5-membered

lactam A lactam is a Cyclic compound, cyclic amide, formally derived from an amino alkanoic acid through cyclization reactions. The term is a portmanteau of the words ''lactone'' + ''amide''. Nomenclature Greek_alphabet#Letters, Greek prefixes in alpha ...

, 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 ''N''-Methyl-2-pyrrolidone (NMP) is an organic compound consisting of a 5-membered lactam. It is a colorless liquid, although impure samples can appear yellow. It is miscible with water and with most common organic solvents. It also belongs to t ...

, have a variety of industrial uses.

Production

2-Pyrrolidone is produced industrially almost exclusively by treating aqueous gamma-butyrolactone with

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

at a temperature of 250–290 °C and pressures ranging from 0.4–1.4 MPa over solid magnesium silicate catalysts. : Industrial synthesis of 2-pyrrolidone

The reaction is carried out in a tubular reactor which is packed with the solid

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

. 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 Distillation, also classical distillation, is the process of separating the component substances of a liquid mixture of two or more chemically discrete substances; the separation process is realized by way of the selective boiling of the mixt ...

and purification, the desired 2-pyrrolidone is obtained with a purity of 99.5%. Alternative routes include the catalytic or electrochemical reduction of

succinimide Succinimide is an organic compound with the formula (CH2)2(CO)2NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic imide. It may be prepared ...

, the

carbonylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...

allylamine Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable Alkene, unsaturated amine. Production and reactions All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl ...

, the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of succinonitrile under hydrolytic conditions, and the reaction of maleic or

succinic anhydride Succinic anhydride, is an organic compound with the molecular formula (CH2CO)2O. This colorless solid is the acid anhydride of succinic acid. Preparation In the laboratory, this material can be prepared by dehydration of succinic acid. Such dehy ...

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 BASF SE (), an initialism of its original name , is a European Multinational corporation, multinational company and the List of largest chemical producers, largest chemical producer in the world. Its headquarters are located in Ludwigshafen, Ge ...

and ISP (International Speciality Products, now

Ashland Inc. Ashland, Inc., is an American chemical company headquartered in Wilmington, Delaware. The company was founded in the city of Ashland, Kentucky, in 1924, where it was headquartered before moving to Wilmington in 1994. The company has five wholly o ...

Uses

2-Pyrrolidone itself is used in inkjet cartridges. A variety of pharmaceutical drugs are 2-pyrrolidone derivatives, including

cotinine Cotinine is an alkaloid found in tobacco and is also the predominant metabolite of nicotine, typically used as a biomarker for exposure to tobacco smoke. Cotinine is currently being studied as a treatment for depression, post-traumatic stress d ...

doxapram Doxapram is a respiratory stimulant, or analeptic. Administered intravenously, doxapram stimulates an increase in tidal volume, and respiratory rate. Medical uses Doxapram is used in intensive care settings to stimulate the respiratory rate in p ...

, povidone, and

ethosuximide Ethosuximide, sold under the brand name Zarontin among others, is a medication used to treat absence seizures. It may be used by itself or with other antiseizure medications such as valproic acid. Ethosuximide is taken by mouth. Ethosuximide ...

, and the

racetam Racetams, also sometimes known simply as pyrrolidones, are a class of drugs that share a pyrrolidone nucleus. Many, but not all, specifically have a 2- oxo-1- pyrrolidine acetamide (piracetam) nucleus. Some racetams, such as piracetam, aniracet ...

s. The chemical is an intermediate in the production of the

polyvinylpyrrolidone Polyvinylpyrrolidone (PVP), also commonly called povidone, is a water-soluble polymer compound made from the monomer ''N''-vinylpyrrolidone. PVP is available in a range of molecular weights and related viscosities, and can be selected according ...

precursor

vinylpyrrolidone ''N''-Vinylpyrrolidone (NVP) is an organic compound consisting of a 5-membered lactam ring linked to a (2 carbon) vinyl group. It is a colorless liquid although commercial samples can appear yellowish. It is produced industrially by vinylation ...

Safety

2-Pyrrolidone is relatively innocuous with an

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

in the range of grams per kilogram (rats, oral). It is not mutagenic. It can be an eye irritant.

References

External links

* {{DEFAULTSORT:Pyrrolidone, 2- Amide solvents