Study On Synthesis Of Furan Ester Derivatives And Application In Cigarettes

12 kinds of furan derivatives were synthesized by esterification reaction,and the optimal reaction conditions were researched by orthogonal experiment and single factor experiment.The structures of synthesized compounds were confirmed by IR,1H NMR,13 C NMR and HRMS.Some compounds were analyzed by thermo gravimetric analysis,pyrolysis analysis and the application of the target compounds in cigarette flavoring.The final results showed that:(1)Using alpha-furanacrylic acid as raw material,reacted with anisalcohol,geraniol,cis-3-hexen-1-ol,cis-6-nonen-1-ol,nonanol,n-octyl alcohol,isobutyl alcohol,benzoic alcohol and phenethyl alcohol,9 kinds of esters compounds of alpha-furanacrylic acid were synthesized.Using geraniol and cis-3-hexen-1-ol as representative,the effect of reaction time,reaction temperature and molar ratio of acid to alcohol on reaction yield were studied.The optimal synthesis conditions of ester of alpha-furanacrylic acid was screened out: dichloromethane as solvent,molar ratio of acid to alcohol was 1:1.2,temperature was 25 ℃,reaction time was 6 hours.(2)Using 2,5-furandicarboxylicacid as raw material,3 kinds of esters of 2,5-furandicarboxylicacid were synthesized by esterification catalyzed by concentrated hydrochloric acid and refluxed at 80 ℃.(3)As representative,3b,3c,3d,3i,6b and 6c were studied by TG-DTG-DSC to study their stabilities and the rules of mass weightlessness variation.The result showed that they were stable at 113.3 ℃,92.6 ℃,128.4 ℃,249.3 ℃,231.6 ℃and 212.1 ℃,respectively.(4)Using α-furanacrylic Acid-cis-3-hexen-1-ol ester,α-furanacrylic Acid-cis-6-nonen-1-ol ester,α-furanacrylic Acid nonanol ester,and α-furanacrylic Acid n-octyl alcohol ester as representative,pyrolysis behaviors of α-furanacrylic acid ester compounds under 300 ℃,600 ℃ and 900 ℃ were studied,and the pyrolysis mechanism were discussed.From the perspective of the cracking components,a variety of pyrolysis components were aroma substances,and these substances could effectively improve the cigarette taste,enhance the fragrance of cigarette.(5)Cigarette flavoring and smoking tests were designed on the synthesized compounds(3b,3c,3d,3g).The result showed that: appropriate concentration of furan compounds added in flue cured tobacco could significantly improve cigarettesmoking quality,supplement cigarette aroma,alleviate offensive odor,decrease irritation,improve the quality of cigarette taste,enhance smoking smooth and softness,plenty and coordinate the smoking.The suitable concentration of 3b,3c and 3d added into cigarettes was 0.08‰,and the concentration of 3g was 0.12‰.