Methylpyrrolidone

Methylpyrrolidone
IUPAC name 1-Methyl-2-pyrrolidone
Other names N-Methyl-2-pyrrolidone
Identifiers
CAS number	872-50-4 Y
PubChem	13387
ChemSpider	12814 Y
UNII	JR9CE63FPM Y
KEGG	C11118 Y
ChEBI	CHEBI:7307 N
ChEMBL	CHEMBL12543 Y
Jmol-3D images	Image 1
SMILES CN1CCCC1=O
InChI InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 Y Key: SECXISVLQFMRJM-UHFFFAOYSA-N Y InChI=1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 Key: SECXISVLQFMRJM-UHFFFAOYAL
Properties
Molecular formula	C5H9NO
Molar mass	99.13 g mol−1
Density	1.028 g/cm3
Melting point	-24 °C, 249 K, -11 °F
Boiling point	202-204 °C, 475-477 K, 396-399 °F
Hazards
NFPA 704	2 1 1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Methyl-2-pyrrolidone (NMP) is a chemical compound with 5-membered lactam structure. It is a clear to slightly yellow liquid miscible with water and solvents like 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-methyl-2-pyrrolidinone, and m-pyrrole, and pharmasolve.

N-Methylpyrrolidone 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] In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.^[2]

N-Methyl-2-pyrrolidone 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 and then by the European Commission in 2003. 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.^[3]

See also

• 2-Pyrrolidone
• 1,3-Dimethyl-2-imidazolidinone (DMI)

References

1. ^ ^{a b} "Products: N-Methylpyrrolidone". BASF. http://www.basf.com/diols/bcdiolsnmp.html. Retrieved 2007-11-11. 
2. ^ ""Pharmasolve"". International Specialty Products. http://www.ispcorp.com/products/pharma/content/brochure/pharmasolve/Pharmasolve%20ver98.pdf. Retrieved 2008-04-15. ^{[dead link]}
3. ^ Reisch, Mark (July 21, 2008). "Solvent users look to replace NMP". Chemical & Engineering News: 32.