N-Methyl-2-pyrrolidone

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N-Methyl-2-pyrrolidone
IUPAC name

1-Methyl-2-pyrrolidone

Other names

N-Methylpyrrolidone; N-methylpyrrolidinone; NMP

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
2
2
1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

N-Methyl-2-pyrrolidone (NMP) is a chemical compound with 5-membered lactam structure. It is a colorless to slightly yellow liquid miscible with water. It is also miscible with most common solvents such as ethyl acetate, chloroform, benzene and lower alcohols or ketones. It also belongs to the class of dipolar aprotic solvents which includes also dimethylformamide, dimethylacetamide and dimethyl sulfoxide. Other names for this compound are: 1-methyl-2-pyrrolidone, N-methylpyrrolidone, N-methylpyrrolidinone and the brand name Pharmasolve.

NMP is used to recover pure hydrocarbons while processing petrochemicals (such as the recovery of 1,3-butadiene using NMP as an extractive distillation solvent) and in the desulfurization of gases. Due to its good solvency properties N-methyl-2-pyrrolidone is used to dissolve a wide range of chemicals, especially in the polymers field. It also used as a solvent for surface treatment of textiles, resins and metal coated plastics or as a paint stripper.[1] 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]

NMP and its derivatives are used as intermediates for the synthesis of agrochemicals, pharmaceuticals, textile auxiliaries, plasticizers, stabilizers and specialty inks. It is also employed as a nylon precursor. The rubber industry uses it for SBR latex production and the electronics industry for printed circuit board manufacturing.[1]

World production capacity for NMP was 226 million lb in 2006. NMP has desirable properties such as low volatility, low flammability and relatively low toxicity. However, it has been identified as a reproductive toxicant, first by California in 2001[3] and then by the European Commission in 2003.[citation needed] 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]

See also

References

  1. ↑ 1.0 1.1 "Products: N-Methylpyrrolidone". BASF. Retrieved 2007-11-11. 
  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. 
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