Sorbitan Esters
Title: Sorbitan Esters
Additional Names: Sorbitan fatty acid esters; SFAE
Literature 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).
 
Derivative Type: Polyoxyethylene derivatives see Polysorbates
 
Derivative Type: Sorbitan Laurate
CAS Registry Number: 1338-39-2
Additional Names: Sorbitan monolaurate
Trademarks: Alkamuls SML (Alkaril); Arlacel 20 (ICI); Emsorb 2515 (Henkel); Glycomul L (Lonza); Span 20 (ICI)
Molecular Formula: C18H34O6
Molecular Weight: 346.46
Percent Composition: 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 Type: Sorbitan Stearate
CAS Registry Number: 1338-41-6
Additional Names: Sorbitan monostearate
Trademarks: Alkamuls SMS (Alkaril); Arlacel 60 (ICI); Glycomul S (Lonza); Span 60 (ICI)
Molecular Formula: C24H46O6
Molecular Weight: 430.62
Percent Composition: 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.
Melting point: mp 49-65°
 
Derivative Type: Sorbitan Oleate
CAS Registry Number: 1338-43-8
Additional Names: Sorbitan monooleate
Trademarks: Alkamuls SMO (Alkaril); Arlacel 80 (ICI); Capmul O (Capital City Prod.); Emsorb 2500 (Henkel); Glycomul O (Lonza); Span 80 (ICI)
Molecular Formula: C24H44O6
Molecular Weight: 428.60
Percent Composition: 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).

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