Synthesis of aromatic triols and triacids from oleic and erucic acid: separation and characterization of the asymmetric and symmetric isomers.
Hexasubstituted benzene derivatives, aromatic triols 4, 9 and triacids 5, 10 have been synthesized from oleic and erucic acid derivatives followed by a cyclotrimerization step catalyzed by palladium-on-carbon (Pd/C) and chlorotrimethylsilane (TMSCl). The asymmetric isomer, which is the main product, was isolated from its symmetric isomer by flash chromatography. All the products were fully characterized by IR, (1)H NMR, (13)C NMR and mass spectrometry. The products are suitable monomers for the production of polyurethanes, polyesters and polyamides.
Alberta Lipid Utilization Program, Department of Agricultural Food and Nutritional Science, 4-10 Agriculture/ Forestry Centre, University of Alberta, Edmonton, Alberta, Canada T6G 2P5.
Jin
J
Yue
Suresh S
SS
Narine
D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000302:isolation & purification; D004883:Erucic Acids / Q000138:chemical synthesis* / Q000302:isolation & purification; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D009829:Oleic Acids / Q000138:chemical synthesis* / Q000302:isolation & purification; D013237:Stereoisomerism
D001555:Benzene Derivatives; D004883:Erucic Acids; D005233:Fatty Alcohols; D009829:Oleic Acids