Study On Synthesis And Antimicrobial Activity Of Furfuryl Fumarates

Preventing food spoilage is an important part of food industry. And it is the focus problem to study effective, low poison and wide range preservatives. In this paper antimicrobial activity of furfuryl fumarate was predicted according to the laws of food preservatives. A new water-soluble compound sodium mono-furfuryl fumarate was prepared. Furthermore methyl-furfuryl fumarte was synthesized using loaed Al resin as esterification catalyst. At the same time antimicrobial activity of methyl-furfuryl fumarte was studied systematically. According to the laws of food preservatives, safe and hydrophobic furfuryl alcohol was attached to a carboxyl of fumaric acid. Another carboxyl attached to methanol or kept dissociative. The antimicrobial activity of furfuryl fumarate was predicted by calculating electron orbit parameters. The results showed that furfuryl fumarate should have better antimicrobial activity and could be the target of further study. Resin catalyst loaded Al was prepared by 732 ion exchange resin and AlCl3. The solvent was ethanol ,and H type resin was dried for 35h. Better preparation technology was AlCl3 dosage of 8%, ethanol volume of 80ml, reaction temperature of 78.3℃and reaction time of 8h. The content of Al3+ in resin was 1.44g/100g. Infra-red spectrums showed that absorption peak of 1020cm-1 of 732 rein devided into two peaks of 1011cm^-1 and 1025cm^-1 of loaded resin. This suggested that 732 resin reacted with AlCl3. Mono-furfuryl maleic ester was acquired by esterification of maleic anhydride and furfuryl alcohol of 1:1 at 90℃for 2.5h. Then isomeric catalyst aluminum chloride anhydrous was added and mono-furfuryl fumarate was prepared by reacting at 90℃for 5h. Sodium mono-furfuryl fumarate was prepared on the basis of mono-furfuryl fumarate. Its better synthesis technology was synthesized by heating mono-furfuryl fumarate and sodium carbonate of 1:0.8. The content of mono-furfuryl fumarate in the product was 95.51%. Infra-red spectrum of the product showed that 1726cm^-1 was the absorption peak of C=O, 1630cm^-1 was the absorption peak of C=C of fumaric acid, 1570cm^-1, 1503cm^-1 and 1432cm^-1 were absorption peaks of furan ring, 1338cm^-1 and 1161cm^-1 were absorption peaks of ester group. These suggested that the product was sodium mono-furfuryl fumarate. Antimicrobial activity of sodium mono-furfuryl fumarate showed that its minimum inhibition concentration was 0.80g/L for Eschericheae coli, 0.90g/L for Bacillus subtilis, 0.80g/L for Staphylococcus aureus, 1.00g/L for Saccharomyces cerivisiae, 0.80g/L for Aspergillus niger. These showed that sodium mono-furfuryl fumarate could inhibit bacteria and mold effectively. At the same time it could inhibit the growth of microorganisms and decrease adaptive capability of microorganisms. Its effect was better than that of sodium benzoate. Sodium mono-furfuryl fumarate was water-soluble and its solubility was 249.26g/L in water. It could be used in more foods. Methy-furfuryl fumarate could be synthesized by methanol first or furfuryl alcohol first. The latter route was better comparing two routes. That is to say methy-furfuryl fumarate was prepared by maleic anhydride, furfuryl alcohol and methanol. This route could save the cost of synthesis, protect solid acid catalyst and simplify the purification of the product. Mono-furfuryl maleic ester was acquired by esterification of maleic anhydride and furfuryl alcohol of 1:1 at 90℃for 2.5h. Then isomeric catalyst aluminum chloride anhydrous was added and mono-furfuryl fumarate was prepared by reacting at 90℃for 5h. Afterwards methanol mol of ten times and loaded resin of 10% were added to the system. The system reacted at boiling state for 6h. The yield of methy-furfuryl fumarate was 79%. The results of kinetics study of esterification showed that surface progression of synthesis reaction of mono-furfuryl maleic anhydride was one. And reaction velocity constant k increased with temperature. The activation energy of this reaction was 12.74kJ/mol. Reaction surface progression of methyl...