162. Adipic Acid

Nomenclature

CAS number: 124-04-9
Hexanedioic acid; 1,4-butanedicarboxylic acid.
C6H10O4; mol wt 146.14.
C 49.31%, H 6.90%, O 43.79%.

Description and references

Found in beet juice. Prepn from cyclohexanol: Bouveault, Locquin, Bull. Soc. Chim. [4] 3, 438 (1908); Ellis, Org. Synth. coll. vol. I, 18 (2nd ed., 1941); Feagen, Copenhaver, J. Am. Chem. Soc. 62, 869 (1940) DOI; US 2191786 (1940); US 2196357 (1940); Zilberman et al., J. Appl. Chem. USSR 29, 621 (1956). Convenient lab prepn from cyclohexanone: L. F. Fieser, Organic Experiments (Heath, Boston, 1964) pp 106-108. Prepn by one-step oxidation of cyclohexane: Onopchenko, Schulz, J. Org. Chem. 38, 3729 (1973) DOI; Tanaka, 167th Am. Chem. Soc. Meet. (Los Angeles, March-April, 1974) Abstracts of Papers, p 29. Manuf: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 50-54. Review: D. E. Danly, C. R. Campbell in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (Wiley-Interscience, New York, 3rd ed., 1978) pp 510-531.

Chemical structure

Properties

Monoclinic prisms from ethyl acetate, from water or from acetone + petr ether. d425 1.360. mp 152°. bp760 337.5°; bp100 265°; bp40 240.5°; bp20 222°; bp10 205.5°; bp5 191°; bp1.0 159.5°. K1 (25°) = 3.90 × 105; K2 = 5.29 × 106. Absorption spectrum: Ramart-Lucas, Salmon-Legagneur, Compt. Rend. 189, 916 (1929). Freely sol in methanol, ethanol. Sol in boiling water, acetone. Slightly sol in water, cyclohexane. Practically insol in benzene, petr ether. 100 ml of a satd aq soln contains 1.44 g; 100 ml of boiling water dissolves 160 g; 100 parts of ether dissolve 0.633 parts (w/w) at 19°. pH of satd aq soln (25°) 2.7; pH of 0.1% soln 3.2.

Derivative

Dimethyl ester.
C8H14O4; mol wt 174.19.
C 55.16%, H 8.10%, O 36.74%.

Properties

Liquid, solidifies at 0°, bp10 112°.

Derivative

Diethyl ester.

Nomenclature

Ethyl adipate.
C10H18O4; mol wt 202.25.
C 59.39%, H 8.97%, O 31.64%.

Properties

Liquid, bp 240-245°. d20 1.009. Insol in water. Sol in alcohol and many other organic solvents.

Use

Manuf artificial resins, plastics (nylon), urethan foams. Buffering agent. Used as acidulant in baking powders instead of tartaric acid, cream of tartar, and phosphates because adipic acid is not hygroscopic. As an intermediate in lubricating oil additives.