821-69-2Relevant academic research and scientific papers
Strategies for synthesis of epoxy resins from oleic acid derived from food wastes
Hayes, Theodore,Hu, Yingxue,Sanchez-Vazquez, Sandra A.,Hailes, Helen C.,Aliev, Abil E.,Evans, Julian R. G.
, p. 3159 - 3170 (2016/10/04)
The use of biomass-sourced chemical feedstocks creates a conflict over land use between food and fuel/chemical production. Such conflict could be reduced by making use of the annual 1.3 Pg food waste resource. Oleic acid is available from seed oils such as pumpkin, grape, avocado and mango. Its esterification with diols 1,3-propanediol, resorcinol and orcinol was used to form diesters and the naturally occurring norspermidine was used to prepare a diamide, all under ambient conditions. These compounds were then epoxidized and polymerized. When esterification was followed by epoxidation and subsequent curing at elevated temperature with p-phenylenediamine or diethylenetriamine, hard insoluble resins were formed. When the sequence was changed such that the epoxidized oleic acid was first reacted with cis-1,2-cyclohexanedicarboxylic anhydride and then esterified with orcinol and resorcinol, insoluble crosslinked polymers were also obtained.
Synthesis and characterization of novel diol, diacid and Di-isocyanate from oleic acid
Raghunanan, Latchmi,Yue, Jin,Narine, Suresh S.
, p. 349 - 356 (2014/03/21)
Novel linear diol 2, diacid 3, and diisocyanate 4 with functional groups located at each end of the chain have been produced from oleic acid via a diester precursor. All the compounds were fully characterized by IR, 1H NMR, 13C NMR and Mass Spectrometry. These unbranched terminally-functionalized compounds are important monomers for the manufacture of biodegradable thermoplastic polyurethanes and polyesters. The general synthetic scheme should also prove useful for the syntheses of diols, diacids and diisocyanates from any unsaturated fatty acid.
Thermoplastic polyester amides derived from oleic acid
Zuo, Jiaqing,Li, Shaojun,Bouzidi, Laziz,Narine, Suresh S.
experimental part, p. 4503 - 4516 (2012/05/19)
Three lipid-based Polyester Amides (PEAs) with varying ratios of ester and amide linkages were synthesized. Oleic acid was used as the starting material to produce the intermediates, characterized by MS and NMR, used for polymerization. PEAs were characterized by FTIR and GPC. The PEAs were constrained to have similar number average molecular weights, in the 2 × 104 range, thereby enabling comparison of their physical properties from a structural perspective. The thermal behavior of the polymers was assessed by DSC, DMA and TGA. Thermal degradation was not affected by ester/amide ratios, but Tg increased non-linearly with decreasing ester/amide ratios and correlated with hydrogen-bond density and repeating unit chain length. Crystallinity was studied by XRD and DSC. Degree of crystallization and multiple melting behavior as a function of cooling kinetics were explained well by hydrogen-bond density, repeating unit chain length and density of ester moieties. Mechanical properties were investigated by DMA and Tensile Analysis, with a non-linear increase of storage and tensile moduli recorded as a function of decreasing ester/amide ratios. The findings suggest how approaches to the synthesis of lipid-based PEAs can be targeted to the delivery of specific physical properties.
