Estolides from meadowfoam oil fatty acids and other monounsaturated fatty acids

Abstract

The formation of estolides was detected during the studies on dimerization of meadowfoam oil fatty acids. By adjusting the reaction conditions, it was possible to produce monoestolides with little dimer or trimer formations. Estm lides have potential use in lubricant, cosmetic and ink formulations and in plasticizers. This paper reports the conditions for production of estolides from mixed meadowfoam fatty acids, commercial oleic acid, high-oleic sunflower oil fatty acids, c/s-5¢e/s-13-docosadienoic acid, petroselinic acid and linoleic aCid. KEY WORDS: c/~5, c/~13<locosadienoic acid, cosmetic, estolide, limnanthes, linoleic acid, lubricant, meadowfoam oil fatty adds, mont-moriUonite, oleic acid, petrosellnic acid, plasticizer. 0 2 HO~/

Production of Fatty Acid Components of Meadowfoam Oil in Somatic Soybean Embryos

“…seed oil also contains significant proportions of erucic acid (22:1⌬ 13 ) (15%-20%) and an unusual diene 22:2 ⌬ 5,13 (10%-20%) (Miller et al, 1964;Phillips et al, 1971). Because of the large distance between its double bonds, 22:2⌬ 5,13 has potential industrial utility in the production of novel estolides and hydroxy fatty acids (Burg and Kleiman, 1991;Erhan et al, 1993). As proposed by Pollard and Stumpf (1980), the pathway of 22:2⌬ 5,13 synthesis appears to involve elongation of 18:1⌬ 9 -CoA to produce 20:1⌬ 11 and 22:1⌬ 13 in a manner similar to that found in Brassicaceae seeds (Kunst et al, 1992;Taylor et al, 1992).…”

“…The close position of the double bond of this fatty acid to the carboxy terminus results in chemical and physical properties that are not found in oleic acid (18:1⌬ 9 ), the primary monounsaturated fatty acid of the seed oil of most plant species. For example, 20:1⌬ 5 is more oxidatively stable than 18:1⌬ 9 (Isbell et al, 1999) and can be used as a precursor for the synthesis of industrial compounds such as ␦-lactones (Erhan et al, 1993). The novel properties associated with 20:1⌬ 5 make the seed oil of Limnanthes sp.…”

Polymeric surfactants based on oleic acid. II. Copolymerization of sodium acrylamidostearate and 10-undecen-1-ol in a lamellar liquid crystal

“…(in g/cm 3 ) and M are the density and average molecular weight of the amphiphile, N A is the Avogadro number, and d 00 (in Å) is the interlayer spacing at zero water content in the absence of hydrocarbons. Taking as 0.90 g/cm, 3 A LLC becomes 41.2 Å 2 per molecule before polymerization, and after polymerization A LLC is 1993 Å 2 per copolymer molecule (the molecular weight of the copolymer as 16,500 is used according to the following viscosity measurement).…”

“…Taking as 0.90 g/cm, 3 A LLC becomes 41.2 Å 2 per molecule before polymerization, and after polymerization A LLC is 1993 Å 2 per copolymer molecule (the molecular weight of the copolymer as 16,500 is used according to the following viscosity measurement). The area occupied by one unit of the copolymer, (NaAAS) 2 / UdOH, in the lamellar liquid crystal is decreased to 110.7 Å 2 after the copolymerization (the copolymerization degree of 54 is used which will be discussed later).…”

“…The polymerization of oleic acid does not yield polymer of very high molecular weight due to an autoinhibition effect resulting from the presence of allylic hydrogen in the molecule. 1 Our previous contribution 2 and other articles 3,4 have shown that only low-molecular-weight oligomer can be formed through the polymerization of oleic acid. Hence, a number of polymerization studies 5,6 have been performed on the chemically modified oleic acid-sodium acrylamidostearate, in which the acrylamide side group is attached to the stearic chain at the carbon atom that has allylic hydrogen present in oleic acid.…”