4918. Iminodisuccinic Acid

Nomenclature

CAS number: 7408-20-0; 70543-06-5 (unspecified stereo)
N-[(1S)-1,2-Dicarboxyethyl]-l-aspartic acid; 2,2′-iminodisuccinic acid.
C8H11NO8; mol wt 249.17.
C 38.56%, H 4.45%, N 5.62%, O 51.37%.

Description and references

Synthesis of ester from fumaric acid, ammonia and water: G. Stadnikoff, Ber. 44, 44 (1911). Industrial processes: GB 1306331 (1971 to Pfizer); T. Groth et al., US 6107518 (2000 to Bayer). Synthesis and complex forming properties: E. D. Malakhaev et al., J. Gen. Chem. USSR 48, 2361 (1978). Thermochemical study: V. P. Vasil'ev et al., Russ. J. Phys. Chem. 63, 1566 (1989). Formation constants with metal cations: C. K. Gangoda, D. R. Williams, Chem. Speciation Bioavailability 9, 101 (1997).

Chemical structure

Properties

White solid, mp 206-208°. pK1 2.96 ±0.05; pK2 3.84 ±0.02; pK3 4.83 ±0.05; pK4 10.12 ±0.04 (25°). Heat of combustion: 2974.3 ±0.6 kJ/mol. Sol in water; insol in alcohol, ether, acetone, benzene.

Derivative

Tetrasodium salt.

Nomenclature

CAS number: 144538-83-0
Baypure CX 100 (Bayer).

Description and references

Review of commercial product: NICNAS New chemical assessment: Aspartic acid, N-(1,2-dicarboxyethyl)-tetrasodium salt, (Sydney, Nat. Ind. Chem. Notif. Assess. Scheme, 2002) 22 pp.

Properties

White solid, mp >300°. Bulk density (kg/m3): ≈740. Vapor pressure at 20°: 1.5×10-16 kPa. Sol at 20° (g/l): water 564 (pH 13.1). LD50 in rats (mg/kg): >2000 orally; >2000 dermally (NICNAS).

Use

Biodegradable metal chelator in detergents, cleaners and personal care products; in photographic applications; in trace nutrient agricultural fertilizers. In mfr of textiles and newspaper. Scale deposit remover, water softener, bleaching agent stabilizer.