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| Names | |||
|---|---|---|---|
| Preferred IUPAC name 1-Methylpyrrolidin-2-one | |||
| Other names 1-Methyl-2-pyrrolidone N-Methylpyrrolidone N-Methylpyrrolidinone Pharmasolve | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.011.662 | ||
| KEGG |
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| UNII | |||
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| Properties | |||
| C5H9NO | |||
| Molar mass | 99.133 g·mol−1 | ||
| Density | 1.028 g/cm3 | ||
| Melting point | −24 °C (−11 °F; 249 K) | ||
| Boiling point | 202 to 204 °C (396 to 399 °F; 475 to 477 K) | ||
| Miscible[1] | |||
| Solubility inEthanol,acetone,diethylether,ethyl acetate,chloroform,benzene | Soluble[1] | ||
| logP | −0.40[2] | ||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 91 °C (196 °F; 364 K)[1] | ||
| 245 °C (473 °F; 518 K)[1] | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
N-Methyl-2-pyrrolidone (NMP) is anorganic compound consisting of a 5-memberedlactam. 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 the class of dipolaraprotic solvents such asdimethylformamide anddimethyl sulfoxide. It is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (includingpolyvinylidene difluoride, PVDF).[3] It has a strong dipole moment and hydrogen bonding due to its cis-amide conformation.[4]: Fig. 5(b)
NMP is produced industrially by a typical ester-to-amide conversion, by treatinggamma-butyrolactone withmethylamine. Alternative routes include the partialhydrogenation ofN-methylsuccinimide and the reaction ofacrylonitrile with methylamine followed byhydrolysis. About 200,000 to 250,000 tons are produced annually.[3]
NMP reacts with phosphorus pentasulfide to give its analogous thioamide.
With sodium hydroxide NMP undergoes reversible ring opening, yielding sodium N-methyl-4-aminobutyrate.[5]
NMP is used to recover certainhydrocarbons generated in the processing ofpetrochemicals, such as the recovery of1,3-butadiene andacetylene. Its good solvency properties have also led to NMP's use to dissolve a wide range ofpolymers. Specifically, it is used as a solvent for surface treatment oftextiles, resins, and metal coated plastics or as apaint stripper. NMP is also used as a solvent in the production ofpolyphenylene sulfide.[5]
NMP is used in the production ofaramid fibersTwaron andKevlar. In the pharmaceutical industry,N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.[6] It is also used heavily inlithium ion battery fabrication, as a solvent for electrode preparation, because NMP has a unique ability to dissolvepolyvinylidene fluoride binder.
In thePurisol process, developed byLurgi AG in the 1960s, a cold (ca. −15 °C) aqueous solution of NMP is used to removehydrogen sulfide fromsour gas and fromhydrodesulfurization facilities.[7] It offers some advantages over theSelexol process in that it is more selective for hydrogen sulfide. Furthermore, it promotes the hydrolysis of somecarbonyl sulfide, a common component of sour gas:
This hydrolysis step further enriches the hydrogen sulfide content of the off-gas when the NMP is stripped. The sulfur-rich gas is well suited for aClaus unit, which affords solidelemental sulfur.[8]
N-Methyl-2-pyrrolidone (NMP) is classified as a reproductive toxicant (H360D: May damage the unborn child) and can cause skin and eye irritation and respiratory irritation (H315, H319, H335).[9] Studies show NMP exposure can increase the risk of developmental toxicity, including miscarriage and fetal death.[10][11]: 24 Good ventilation and PPE are recommended for safe handling.[12]
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