Synthesis and Characterization of Novel Fluoroalkyl Unsaturated Multi-carboxylic Acid Esters

A series of fluorinated unsaturated esters which can be used as fluorine-containing monomers have been synthesized.The esterification of maleic acid,itaconic acid,and trans-aconitic acid with 1,1,2,2-tetrahydroperfluorooctanol and 1,1,5-octafluoropentanol was carried out,respectively.The objective monomers were obtained by using p-toluene sulfonic acid as catalyst,hydroquinone as the anti-polymerizing agent,toluene as solvent and water carrying agent.The objective products were isolated by column chromatography and characterized by Fourier transform infrared spectroscopy (FT-IR),hydrogen-1 nuclear magnetic resonance (1H NMR),fluorine-19 nuclear magnetic resonance (19F NMR),and high resolution mass spectrometry (HRMS).The yield of the objective products was various from 30％ to 85％.The reaction result shows that the esterification of 1,1,5-octafluoropentanol with certain carboxylic acid is more difficult than that of 1,1,2,2-tetrahydroperfluorooctanol.