8016. 2-Pyrrolidone

Nomenclature

CAS number: 616-45-5
2-Pyrrolidinone; 2-oxopyrrolidine; α-pyrrolidone; 2-ketopyrrolidine.
C4H7NO; mol wt 85.10.
C 56.45%, H 8.29%, N 16.46%, O 18.80%.

Description and references

Prepd on a large scale from butyrolactone by a Reppe process: DE 1085525 (to BASF). Other prepns: Metzger, Seelert, Angew. Chem. 75, 919 (1963); Copenhaver, Ney, US 3095423 (1963 to Minnesota Mining & Manuf); Lidov, US 3109005 (1963 to Halcon International).

Chemical structure

Properties

Liquid above 25°. bp760 245°; bp9.2 113-114°; bp0.2 76°. d425 1.116. Flash pt, open cup: 265°F (129°C). Viscosity at 25° = 13.3 cP. Dipole moment: 2.3. In the presence of the stoichiometric amount of water a cryst monohydrate, mp 30°, can be formed. Non-corrosive. Good chemical stability. Miscible with water, ethanol, ether, chloroform, benzene, ethyl acetate, carbon disulfide.

Use

Intermediate in the manuf of polyvinylpyrrolidone and polypyrrolidone (a polymer, formed in the presence of alkaline catalysts). Also used as high-boiling solvent in petroleum processing, acrylonitrile manuf. Industrial solvent for polymers, chlordane, DDT, sorbitol, glycerol, iodine, sugars. In specialty printers inks. As plasticizer and coalescing agent for acrylic-styrene emulsion-type floor polishes.