55. Acetic Acid

Nomenclature

CAS number: 64-19-7
Glacial acetic acid; ethanoic acid; Aci-Jel (Ortho).
C2H4O2; mol wt 60.05.
C 40.00%, H 6.71%, O 53.29%.

Description and references

Obtained in the destructive distillation of wood; from acetylene and water, via acetaldehyde by oxidation with air. Manuf processes: Bhattacharyya, Sourirajan, J. Appl. Chem. 6, 442 (1956); eidem, ibid. 9, 126 (1959); Elce et al., US 2800504 (1957 to Distillers Co.); Wirth, US 2818428 (1957 to British Petroleum); McKusick and Hoover, US 2940913 and US 2940914 (both 1960 to Du Pont); Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 8-15. Toxicity data: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951). Review: F. S. Wagner in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (Wiley-Interscience, New York, 3rd ed., 1978) pp 124-147.

Chemical structure

Properties

Liquid; pungent odor. d16.67 (liq) 1.053; d16.60 (solid) 1.266. d2525 1.049. bp 118°. mp 16.7°. nD20 1.3718. Flash pt, closed cup: 103°F (39°C). Corrosive, flammable. Contracts slightly on freezing. Excellent solvent for many organic compounds; also dissolves phosphorus, sulfur and halogen acids. Miscible with water, alcohol, glycerin, glycerol, ether, carbon tetrachloride. Practically insol in carbon disulfide. Weakly ionized in aq solns: pKa 4.74. pH of aq solns 1.0M = 2.4; 0.1M = 2.9; 0.01M = 3.4. LD50 in rats (g/kg): 3.53 orally (Smyth).
Incompat. Carbonates, hydroxides, many oxides, phosphates.

Caution

Ingestion may cause severe corrosion of mouth and G.I. tract, with vomiting, hematemesis, diarrhea, circulatory collapse, uremia, death. Chronic exposure may cause erosion of dental enamel, bronchitis, eye irritation, cf. Patty's Industrial Hygiene and Toxicology vol. 2C, G. D. Clayton, F. E. Clayton, Eds. (Wiley-Interscience, New York, 3rd ed., 1982) p 4909-4911.

Use

Manuf various acetates, acetyl compounds, cellulose acetate, acetate rayon, plastics and rubber in tanning; as laundry sour; printing calico and dyeing silk; as acidulant and preservative in foods; solvent for gums, resins, volatile oils and many other substances. Widely used in commercial organic syntheses. Aqueous and nonaqueous acid-base titrations. Trace metal analysis. Pharmaceutic aid (acidifier).

Therapeutic Category (Veterinary)

Vesicant, caustic, destruction of warts.