N-Methyl-2-pyrrolidone

N-Methyl-2-pyrrolidone
Names
Preferred IUPAC name
1-Methylpyrrolidin-2-one
Other names
1-Methyl-2-pyrrolidone
N-Methylpyrrolidone
N-Methylpyrrolidinone
Pharmasolve
Identifiers
CAS Number
  • 872-50-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:7307 checkY
ChEMBL
  • ChEMBL12543 checkY
ChemSpider
  • 12814 checkY
ECHA InfoCard 100.011.662 Edit this at Wikidata
KEGG
  • C11118 checkY
PubChem CID
  • 13387
UNII
  • JR9CE63FPM checkY
CompTox Dashboard (EPA)
  • DTXSID6020856 Edit this at Wikidata
InChI
  • InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 checkY
    Key: SECXISVLQFMRJM-UHFFFAOYSA-N checkY
  • InChI=1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
    Key: SECXISVLQFMRJM-UHFFFAOYAL
  • CN1CCCC1=O
Properties
Chemical formula
 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)
Solubility in water
 Soluble[1]
Solubility in Ethanol, acetone, diethylether, ethyl acetate, chloroform, benzene Soluble[1]
log P −0.40[2]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
2
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

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 the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide. It is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (including polyvinylidene difluoride, PVDF).[3]

Preparation

NMP is produced industrially by a typical ester-to-amide conversion, by treating gamma-butyrolactone with methylamine. Alternative routes include the partial hydrogenation of N-methylsuccinimide and the reaction of acrylonitrile with methylamine followed by hydrolysis. About 200,000 to 250,000 tons are produced annually.[3]

Applications

NMP is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene. It is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization facilities. Its good solvency properties have led to NMP's use to dissolve a wide range of polymers. Specifically, it is used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper. It is also used as a solvent in the commercial preparation of polyphenylene sulfide. In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.[4] It is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, because NMP has a unique ability to dissolve polyvinylidene fluoride binder. Due to NMP's toxicity and high boiling point, there is much effort to replace it in battery manufacturing with other solvent(s), like water.[5][6]

Safety

N-Methyl-2-pyrrolidone is a relatively innocuous compound with an LD50 of 4150 mg/kg (oral, rats).[7] It is non-mutagenic[3]

See also

References

  1. ^ a b Sigma-Aldrich Co., 1-Methyl-2-pyrrolidinone. Retrieved on 22 March 2022.
  2. ^ "N-Methylpyrrolidone_msds".
  3. ^ a b c Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang"2-Pyrrolidone, R. (2011). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_457.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: numeric names: authors list (link)
  4. ^ "Pharmasolve® Drug Solubilizer" (PDF). PharmaGuide. International Specialty Products, a division of Ashland Inc.: Page 9. Retrieved 2012-06-06.
  5. ^ "Production of batteries made cheaper and safer, thanks to Finnish researchers". Science Daily. Retrieved 7 May 2015.
  6. ^ Wu, F., Liu, M., Li, Y. et al. High-Mass-Loading Electrodes for Advanced Secondary Batteries and Supercapacitors. Electrochem. Energ. Rev. 4, 382–446 (2021). https://doi.org/10.1007/s41918-020-00093-0
  7. ^ "Safety Data Sheet". 2024-03-06. Retrieved 2024-07-31.