6134. Methyl Vinyl Ketone

Nomenclature

CAS number: 78-94-4
3-Buten-2-one; Δ3-2-butenone; methylene acetone; acetyl ethylene; δ-oxo-α-butylene; vinyl methyl ketone.
C4H6O; mol wt 70.09.
C 68.54%, H 8.63%, O 22.83%.

Description and references

Prepn by condensation of acetone and formaldehyde to 3-ketobutanol and dehydration to methyl vinyl ketone: Merling, Khler, J. Soc. Chem. Ind. 29, 1037 (1910); White, Haward, J. Chem. Soc. 1943, 25. Prepn from vinylacetylene: Conaway, US 1967225 (1934 to DuPont). For review and polymerization characteristics see “Vinyl Ketone Polymers” in Encyclopedia of Polymer Science and Technology vol. 14 (Interscience, New York, 1971) pp 617-636.

Chemical structure

Properties

Liquid with pungent odor. bp760 81.4°. nD20 1.4086. d420 0.8636; d425 0.8407. Poisonous; flammable; corrosive. Easily soluble in water, methanol, ethanol, ether, acetone, glacial acetic acid. Slightly sol in hydrocarbons. Forms a binary azeotrope with water, bp760 75° (12% water). uv spectrum and electric moments: Rogers, J. Am. Chem. Soc. 69, 2544 (1947). Polymerizes on standing.

Caution

Readily absorbed through skin causing general poisoning of the organism. Irritating to mucous membranes and respiratory tract.

Use

Alkylating agent; commercial starting material for plastics; as intermediate in the synthesis of steroids and vitamin A.