N-Methyl-2-pyrrolidone

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N-Methyl-2-pyrrolidone
N-Methylpyrrolidone Structural Formulae.png
Identifiers
CAS number 872-50-4 YesY
PubChem 13387
ChemSpider 12814 YesY
UNII JR9CE63FPM YesY
KEGG C11118 YesY
ChEBI CHEBI:7307 YesY
ChEMBL CHEMBL12543 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H9NO
Molar mass 99.13 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)
Hazards
NFPA 704
Flammability code 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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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 and plastics industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials.[1]

Preparation[edit]

NMP is produced industrially by a typical ester-to-amide conversion, by treating butyrolactone with methylamine. Alternative routes include the partial hydrogenation of N-methylsuccinimide and the reaction of acrylonitrile with methylamine followed by hydrolysis. About 250,000 tons are produced annually.[1]

Applications[edit]

NMP is used to recover certain hydrocarbons generated in the processing petrochemicals, such as the recovery of 1,3-butadiene and acetylene. It is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization facilities. Due to its good solvency properties NMP is used to dissolve a wide range of polymers. It also used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper. It is utilized 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.[2]

Biological aspects[edit]

NMP is on California's list of chemicals known to possess developmental toxicity.[3][1] In the face of increasing regulation, some manufacturers are considering alternative solvents for some applications, especially where worker exposure is difficult to control, such as in paint stripping, graffiti removal, and agriculture.[4]

On the other hand, NMP biodegrades readily and has low toxicity to aquatic life.[1]

See also[edit]

References[edit]

  1. ^ a b c d Albrecht Ludwig Harreus, R. Backes, J.-O. Eichler, R. Feuerhake, C. Jäkel, U. Mahn, R. Pinkos, R. Vogelsang"2-Pyrrolidone” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2011, Weinheim. doi:10.1002/14356007.a22_457.pub2
  2. ^ "Pharmasolve® Drug Solubilizer". PharmaGuide (International Specialty Products, a division of Ashland Inc.): Page 9. Retrieved 2012-06-06. 
  3. ^ "List of Chemicals as Known to the State of California to Cause Cancer or Reproductive Toxicity". California OEHHA. Retrieved 4 December 2012. 
  4. ^ Reisch, Mark (July 21, 2008). "Solvent users look to replace NMP". Chemical & Engineering News: 32.