1-Methylpyrrolidone
Title: 1-Methylpyrrolidone
CAS Registry Number: 872-50-4
CAS Name: 1-Methyl-2-pyrrolidinone
Additional Names: N-methyl-a-pyrrolidinone; N-methyl-g-butyrolactone; NMP; 1-methylazacyclopentan-2-one; MP
Trademarks: M-Pyrol (ISP)
Molecular Formula: C5H9NO
Molecular Weight: 99.13
Percent Composition: C 60.58%, H 9.15%, N 14.13%, O 16.14%
Literature References: Dipolar aprotic solvent. Commercially prepd by condensation of butyrolactone with methylamine. Prepn: J. Tafel, O. Wassmuth, Ber. 40, 2831 (1907); E. Späth, J. Lintner, ibid. 69, 2727 (1936). Use in extraction of unsaturated/aromatic compounds: E. Mueller, G. Hoehfeld, Proc. 8th World Pet. Congr. 4 (Applied Sci. Publishers, London, 1971) pp 213-219; H. Klein, H. M. Weitz, Hydrocarbon Process. 47, 135 (November, 1968); A. Sequeira et al., ibid. 58, 155 (September, 1979). Physical properties and solubility: Industrial Solvents Handbook (3rd Ed.) 580-582 (1985). Reference guide to properties and use: M-Pyrol®, N-Methyl-2-Pyrrolidone Handbook, ISP (subsidiary of GAF Corp.), 1988. Acute toxicity: W. Bartsch et al., Arzneim.-Forsch. 26, 1581 (1976). Review: E. V. Hort, L. R. Anderson in Kirk-Othmer Encyclopedia of Chemical Technology vol. 19 (Wiley-Interscience, New York, 3rd ed., 1982) pp 514-520.
Properties: Clear liquid. fp -24.4°. bp760 202°. nD25 1.4690. d425 1.027. Flash point, closed cup: 199°F; open cup: 204°F. Viscosity (25°): 1.65 cP. Surface tension at 25°: 40.7 dynes/cm. Dipole moment at 25°: 4.09 D. Dielectric constant at 25°: 32.2. Vapor pressure at 23.2°, 65°: 0.33, 5 mm Hg. Heat of combustion: 719 kcal/mol; of vaporization: 127.3 kcal/kg. Misc with water, alcohol, ether, acetone, ethyl acetate, chloroform, benzene. LD50 in mice, rats (ml/kg): 3.5, 2.2 i.v.; 4.3. 2.4 i.p.; 7.5, 3.8 orally (Bartsch).
Boiling point: bp760 202°
Flash point: Flash point, closed cup: 199°F; open cup: 204°F
Index of refraction: nD25 1.4690
Density: d425 1.027
Toxicity data: LD50 in mice, rats (ml/kg): 3.5, 2.2 i.v.; 4.3. 2.4 i.p.; 7.5, 3.8 orally (Bartsch)
Use: Industrial solvent primarily used in the extraction of aromatics from lube oils. Other applications include recovery and purification of acetylenes, olefins and diolefins, gas purification, and aromatics extraction from feedstocks. Also, used as polymer solvent.

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