Preparation Of Cyclohexyl Methyl Fumarate And Its Antibacterial Effect

α,β-unsaturated carbonyl is regarded as an effective group of antimicrobial activity. Fumarate was effect preservatives containing such group. The purpose of this thesis is to synthesize fumarate which is of high performance, broad-spectrum, low toxicity and low hypersusceptibility .This article focused on developing a practical and economical synthesis route for preparating mono-butyl fumarate and momo-cyclohexyl fumarte through maleic anhydride. Aluminum trichloride is used as isomerize catalyzer. The temperature of esterification, isomerization and isomerize time were investigated. As a result, the yield of mono-butyl fumarate(MBF), and the yield of mono-cyclohexyl fumarate (MCHF) is about 88.4%. The product structure was confirmed by MS and ~1H-NMR. Synthesis of dialkyl fumarate(butyl methyl fumarate(BMF), cyclohexyl methyl fumarate(CHMF)) from mono-alkyl fumarate was further conducted. The reflux time , the proportion of reagents were studied as well as the dosing way of reactant and how to add thionyl chloride which had effects on the synthsis of alkyl fumaryl chloride. The best synthetic condition was obtained. The yield of (E)-butyl-4-chloro-4-oxobut-2-enoate is 93.8%. The yield of BMF is 89.6%, and the yield of CHMF is 88.4% . Structures of CHMF and BMF were confirmed by ~1H-NMR.Antimicrobial activity of MBF, BMF, MCHF and CHMF is systematically studied and the results showed that they can suppress the growth of bacteria. Their antibacterial activitives were all good in the mediums of pH from 3 to 9. The antibacterial activity decreased in this order MCHF > CHMF > MBF > BMF. It is also proved that CHMF and MCHF are thermally stable up to 120℃, whereas the other two products are thermally unstable.Skin tests showed that MCHF and CHMF did stimulate skin less than dimethyl fumarate does, so it may be used in food as a kind of effective, broad-spectrum and low toxicity food preservative.