Synthesis and characterization of oleic succinic anhydrides: Structure-property relations
Abstract: Alkenyl succinic anhydrides (ASA) were prepared by an-ene reaction of n-alkyl (C1 to C5) oleates with maleic anhydride. The purified compounds were characterized by FTIR, 1H NMR, and MS analytical methods to elucidate their structures. Their physicochemical properties were systematically studied and found to depend on the length of the alkyl radical. Structure-property relations were established for viscosity, m.p., and density. The combination of a long hydrophobic chain and a highly polar group with density values close to that of water implied good emulsification properties for some of these molecules. Comparison of the thermal properties of alkyl oleates and their respective ASA demonstrated that the grafting of maleic anhydride allowed the synthesis of compounds with very low melting temperatures (less than −60°C) and good stability at high temperatures (greater than 350°C) under both air and helium atmospheres. All these properties suggest a strong potential for application in the biolubricant or surfactant fields. The combined influences of the succinic part and variable ester moieties imply that each ASA molecule has its own characteristics, based on which applications could be developed.
Summary (1 min read)
- Methyl oleate (>96%) was supplied by Fluka (St Quentin Fallavier, France).
- Density was determined using a 10-mL pycnometer according to ISO standard 279-1981.
RESULTS AND DISCUSSION
- Five oleic acid alkyl esters, from methyl to pentyl, with reasonably high purity (>85%) were required for ASA synthesis.
- The syntheses of butyl and pentyl oleates were based on the complete esterification of oleic acid with the corresponding alcohol.
- The cooled reaction medium was washed with a NaClsaturated aqueous solution and then vacuum distilled.
- ASA appeared to be Newtonian liquids whose viscosities were at least 30 times higher than those of the corresponding alkyl oleates, which ranged from 0.003 to 0.009 Pa⋅s.
- This phenomenon became clearer with the longest alkyl esters.
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...They have essentially been used as monomers for the fabrication of thermosets (14), as the anhydride moiety can react with diamines, diols and polyols, or epoxy resins to yield unsaturated polyester-like resins....
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Their physicochemical properties were systematically studied and found to depend on the length of the alkyl radical. All these properties suggest a strong potential for application in the biolubricant or surfactant fields.