8724. Sorbitan Esters

Nomenclature

Sorbitan fatty acid esters; SFAE.

Description and references

Nonionic surface active agents; partial esters of the common fatty acids (lauric, palmitic, stearic, and oleic) and hexitol anhydrides derived from sorbitol. Commercial products may be mixtures of fatty acid esters of 1,4- and 1,5 anhydrosorbitol and 1,4,3,6-dianhydrosorbitol, but generally conform to the structure depicted below. Prepn: K. R. Brown, US 2322820 (1943 to Atlas Powder Co.). Improved process: G. J. Stockburger, US 4297290 (1981 to ICI). Comprehensive description: P. Becher, “Polyol Surfactants” in Nonionic Surfactants, M. J. Schick, Ed. (Dekker, New York, 1967) pp 247-299. Description of prepn and uses: L. R. Chislett, J. Walford, Int. Flavours Food Addit. 7, 61 (1976). GLC determn of sorbitan monolaurate in plasma: S. H. Giovanetto, Anal. Lett. 16, 867 (1983). Analysis by HPLC: N. Garti et al., J. Am. Oil Chem. Soc. 60, 1151 (1983). Series of toxicity studies: Food Cosmet. Toxicol. 16, 519-542 (1978). Review: Cosmetic, Toiletry and Fragrance Assoc., J. Am. Coll. Toxicol. 4, 65-121 (1985).

Chemical structure

Derivative

Polyoxyethylene derivatives see Polysorbates.

Derivative

Sorbitan Laurate.

Nomenclature

CAS number: 1338-39-2
Sorbitan monolaurate; Alkamuls SML (Alkaril); Arlacel 20 (ICI); Emsorb 2515 (Henkel); Glycomul L (Lonza); Span 20 (ICI).
C18H34O6; mol wt 346.46.
C 62.40%, H 9.89%, O 27.71%.

Properties

Yellow liquid. Acid value: <8. Saponification value: 150-165. Hydroxyl value: 330-360. Sol in mineral oil, cottonseed oil, methanol, ethanol, isopropyl alc, ethylene glycol. Insol in water, propylene glycol.

Derivative

Sorbitan Stearate.

Nomenclature

CAS number: 1338-41-6
Sorbitan monostearate; Alkamuls SMS (Alkaril); Arlacel 60 (ICI); Glycomul S (Lonza); Span 60 (ICI).
C24H46O6; mol wt 430.62.
C 66.94%, H 10.77%, O 22.29%.

Properties

White to tan waxy solid, mp 49-65°. Acid value: 5-11. Saponification value: 140-157. Hydroxyl value: 230-260. Sol in alcohols, carbon tetrachloride, toluene. Insol in water, acetone, mineral spirits.

Derivative

Sorbitan Oleate.

Nomenclature

CAS number: 1338-43-8
Sorbitan monooleate; Alkamuls SMO (Alkaril); Arlacel 80 (ICI); Capmul O (Capital City Prod.); Emsorb 2500 (Henkel); Glycomul O (Lonza); Span 80 (ICI).
C24H44O6; mol wt 428.60.
C 67.26%, H 10.35%, O 22.40%.

Properties

Yellow to amber colored oily liquid. Acid number: 5-8. Saponification value: 140-160. Hydroxyl value: 193-215. Sol in ethanol, isopropyl alc, mineral oil, vegetable oil. Insol in water, propylene glycol.

Use

use: As emulsifiers, stabilizers, and thickeners in foods, cosmetics, and medicinal products. In the textile industry as fiber lubricants and softeners. Pharmaceutic aid (surfactant).