Surfactants from oleic, erucic and petroselinic acid: Synthesis and properties

Abstract

Most surfactants are based on C 12 and C 14 chains from fatty acids and contain alkanols obtained from ethylene. Readily available fatty acids with C 18 and C 22 chains are barely used due to their lower water solubility and less suitable structure for micelle formation. To overcome these deficiencies, we attached polar groups to terminal and/or internal positions of oleic, petroselinic and erucic acid. Internal diols were prepared by epoxidation and acid-catalyzed ring opening or by bishydroxylation with catalytic amounts of osmium tetroxide. Terminal alcohols were prepared by reduction of the methyl esters. For the synthesis of the non-ionic surfactants, the alcohols were reacted with the p-toluenesulfonates of di-, tri-and tetraethyleneglycols or the epoxide ring was opened with the corresponding oligoethyleneglycols. This way, ethoxylates free of homologues were obtained. Sodium sulfate surfactants were prepared by reacting the mono-, di-and triols with different equivalents of chlorosulfonic acid. From the purified products, the spectroscopic and the surfactant properties were determined. The latter are in many cases equal or better than those of commercial ionic and non-ionic surfactants based on C 12 and C 14 carbon chains.

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

“…The surfactants with tensidic properties synthesized by the modification of long chain fatty acids were shown to be comparable or with better properties than those of commercial surfactants of C12 and C14 fatty acids (Dierker and Schäfer, 2010).…”

“…As for palm oil that contains longer chain fatty acids, the modification of the fatty acids has been carried out to increase the polarity of the fatty acids. Epoxide can serve as an intermediate to attach the polar groups to internal positions of the fatty acids (Dierker and Schäfer, 2010). Internal diols can be obtained by acid-catalyzed ring opening of the epoxidized fatty acids or by dihydroxylation in the presence of osmium tetroxide as catalyst.…”

Polymer precursors from catalytic reactions of natural oils

“…[15][16][17][18] For instance, the production of surfactants being efficient and presenting interesting properties such as biocompatibility and biodegradability 19,20 is a successful example of industrial conversion of vegetable oils into valuable chemicals. [21][22][23] The area of industrial conversion of oils into chemicals being wide, the reader's attention will now be focused only in the field of polymers. …”

Fette und Öle als nachwachsende Rohstoffe in der Chemie

“…[72] Oberflächenaktive Verbindungen mit Eigenschaften, die denen von laurischen Ölen entsprechen, wurden aus 1 a, 4 a und 7 a durch Epoxidringöffnung erhalten. [73] 3.2. Additionen an die C-C-Doppelbindung unter Knüpfung einer neuen Kohlenstoff-Kohlenstoff-Bindung 3.2.1.…”