8415. Sebacic Acid

Nomenclature

CAS number: 111-20-6
Decanedioic acid; 1,8-octanedicarboxylic acid.
C10H18O4; mol wt 202.25.
C 59.39%, H 8.97%, O 31.64%.

Description and references

Obtained on a large scale by heating castor oil or ricinoleic acid with sodium hydroxide. Convenient lab procedures: Topchiev, Pavlov, C.A. 47, 8002h (1953); Dominguez et al., J. Chem. Educ. 29, 446 (1952). Also prepd by ozonization of undecylenic acid: Noorduyn, Rec. Trav. Chim. 38, 326 (1919); Verkade et al., ibid. 385. Toxicity study: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). Review and bibliography: Jones, Chimia 5, 169-173 (1951).

Chemical structure

Properties

Monoclinic prismatic tablets, leaflets from acetone + petr ether (commercial product is a white, free-flowing powder having a mild fatty acid odor). d420 1.207. mp 134.5°. bp100 294.5°; bp50 273°; bp15 243.5°; bp10 232°. Sp heat (solid) 0.48 cal/g; sp heat (liq) 0.53 cal/g. Sublimes slowly at 750 mm when heated to mp. nD134 1.422. pK1 4.59; pK2 5.59. Aq solns are neutral to methyl orange. Soly in water: 0.004% at 0°; 0.10% at 20°; 0.42% at 65°; 2.0% at 100°. Freely sol in alcohols, esters, ketones. Soly in ether: 0.1% at 17°. Sparingly sol in hydrocarbons and chlorinated hydrocarbons.

Derivative

Diethyl ester.

Nomenclature

CAS number: 110-40-7
Diethyl sebacate; ethyl sebacate.
C14H26O4; mol wt 258.35.
C 65.09%, H 10.14%, O 24.77%.

Properties

Colorless to yellowish fluid. d420 0.965. bp ≈307° with some decompn. nD20 1.4369. Sol in about 700 parts cold, 50 parts boiling water; misc with alc, ether and other organic solvents. LD50 orally in rats: 14470 mg/kg (Jenner).

Use

Raw material in the manuf of synthetic resins of the alkyd or polyester type, non-migrating plasticizers, polyester rubbers, synthetic fibers of the polyamide type.