Synthesis and characterization of dodecenyl succinate derivatives of saccharides
1994
Assempour, H. | Koenig, M.F. | Huang, S.J.
Acid ester derivatives of sucrose, amylose, and corn starch bearing carbon-carbon double bonds were synthesized by reaction of 2-dodecene-1-ylsuccinic anhydride under homogeneous conditions, using a pyridine catalyst. The esters were characterized by FTIR, NMR, elemental analysis, thermal analysis, and solubility tests. The results show that these saccharides can undergo complete or nearly complete substitution in reaction with the anhydride, within the limits of sensitivity of these techniques. The resultant esters possess remarkable solubility in common organic solvents such as THF, methylene chloride, and toluene. Their solubility gradually decreases with time when stored under ambient conditions due to crosslinking through the incorporated double bonds. The esters react with aqueous NaOH to give a solution with pH approximately 8.
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