N-Methyl-2-pyrrolidone

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(Redirected from Methylpyrrolidone) 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-methyl2-pyrrolidone, N-methylpyrrolidone, Nmethylpyrrolidinone and the brand name Pharmasolve. NMP is used to recover pure hydrocarbons while processing petrochemicals (such as the recovery of 1,3butadiene 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]

N-Methyl-2-pyrrolidone

IUPAC name 1-Methyl-2-pyrrolidone Other names N-Methylpyrrolidone; N-methylpyrrolidinone; NMP

Identifiers CAS number PubChem UNII KEGG ChEBI ChEMBL Jmol-3D images 872-50-4 13387 JR9CE63FPM C11118 CHEBI:7307 CHEMBL12543 Image 1 (http://chemapps.stolaf.edu/jmol/jmol.php? model=CN1CCCC1%3DO) SMILES InChI Properties Molecular formula Molar mass 99.13 g mol1 Density Melting point Boiling point NFPA 704 1.028 g/cm3 -24 C, 249 K, -11 F 202-204 C, 475-477 K, 396-399 F Hazards C5H9NO

ChemSpider 12814

See also

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

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References

1. ^ a b "Products: N-Methylpyrrolidone" Infobox references (http://www.basf.com/diols/bcdiolsnmp.html) . BASF. http://www.basf.com/diols/bcdiolsnmp.html. Retrieved 2007-11-11. 2. ^ "Pharmasolve Drug Solubilizer" (http://online1.ispcorp.com/Brochures/Pharma/PharmaGuide.pdf) . PharmaGuide (International Specialty Products, a division of Ashland Inc.): Page 9. http://online1.ispcorp.com/Brochures/Pharma/PharmaGuide.pdf. Retrieved 2012-06-06. 3. ^ "List of Chemicals as Known to the State of California to Cause Cancer or Reproductive Toxicity" (http://www.oehha.ca.gov/prop65/prop65_list/files/P65single091009.pdf) . California OEHHA. http://www.oehha.ca.gov/prop65/prop65_list/files/P65single091009.pdf. Retrieved 4 December 2012. 4. ^ Reisch, Mark (July 21, 2008). "Solvent users look to replace NMP". Chemical & Engineering News: 32.

Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa)

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