Adipic Acid

Title: Adipic Acid
CAS Registry Number: 124-04-9
CAS Name: Hexanedioic acid
Additional Names: 1,4-butanedicarboxylic acid
Molecular Formula: C6H10O4
Molecular Weight: 146.14
Percent Composition: C 49.31%, H 6.90%, O 43.79%
Line Formula: HOOC(CH2)4COOH
Literature 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); 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); 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.
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 ´ 10-5; K2 = 5.29 ´ 10-6. Absorption spectrum: Ramart-Lucas, Salmon-Legagneur, Compt. Rend. 189, 916 (1929). Freely soluble in methanol, ethanol; sol in acetone. 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°. Slightly sol in cyclohexane. Practically insol in benzene, petr ether. pH of satd aq soln at 25° = 2.7; pH of 0.1% soln = 3.2.
Melting point: mp 152°
Boiling point: bp760 337.5°; bp100 265°; bp40 240.5°; bp20 222°; bp10 205.5°; bp5 191°; bp1.0 159.5°
Density: d425 1.360
Derivative Type: Dimethyl ester
Molecular Formula: C8H14O4
Molecular Weight: 174.19
Percent Composition: C 55.16%, H 8.10%, O 36.74%
Properties: Liquid, solidifies at 0°, bp10 112°.
Boiling point: bp10 112°
Derivative Type: Diethyl ester
Additional Names: Ethyl adipate
Molecular Formula: C10H18O4
Molecular Weight: 202.25
Percent Composition: 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.
Boiling point: bp 240-245°
Density: d20 1.009
Use: Manuf artificial resins, plastics (nylon), urethan foams. 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.
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