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Revision as of 15:19, 28 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit Revision as of 15:30, 28 January 2011 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user taNext edit →
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{{chembox {{chembox
| verifiedrevid = 402498108 | verifiedrevid = 410572798
| Name = Methylpyrrolidone | Name = Methylpyrrolidone
| ImageFile = N-Methylpyrrolidone Structural Formulae.png | ImageFile = N-Methylpyrrolidone Structural Formulae.png
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = JR9CE63FPM | UNII = JR9CE63FPM
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11118 | KEGG = C11118
| InChI = 1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 | InChI = 1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
| InChIKey = SECXISVLQFMRJM-UHFFFAOYAL | InChIKey = SECXISVLQFMRJM-UHFFFAOYAL
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 12543 | ChEMBL = 12543
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}

Revision as of 15:30, 28 January 2011

Methylpyrrolidone
Names
IUPAC name 1-Methyl-2-pyrrolidone
Other names N-Methyl-2-pyrrolidone
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.662 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3Key: SECXISVLQFMRJM-UHFFFAOYSA-N
  • InChI=1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3Key: SECXISVLQFMRJM-UHFFFAOYAL
SMILES
  • CN1CCCC1=O
Properties
Chemical formula C5H9NO
Molar mass 99.13 g/mol
Density 1.028 g/cm
Melting point −24 °C
Boiling point 202-204°C
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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
1 2 1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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.

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.

See also

References

  1. ^ "Products: N-Methylpyrrolidone". BASF. Retrieved 2007-11-11.
  2. ""Pharmasolve"" (PDF). International Specialty Products. Retrieved 2008-04-15.
  3. Reisch, Mark (July 21, 2008). "Solvent users look to replace NMP". Chemical & Engineering News: 32.
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