环己酮异VC缩酮的合成及其抗氧化性能研究  

Synthesis and Its Antioxidation Activity of Cyclohexanone D-Isoascorbic Acid Ketal

作　　者：郑大贵[1] 余衍文[2] 

机构地区：[1]上饶师范学院江西省普通高校应用有机化学重点实验室,江西上饶334001 [2]南昌大学化学系,江西南昌330031

出　　处：《化学世界》2008年第12期727-730,共4页Chemical World

基　　金：江西省普通高校重点实验室科技计划项目(赣教技字[2006]302号)

摘　　要：以对甲苯磺酸为催化剂，N，N-二甲基乙酰胺（DMAc）为溶剂，环己烷为带水剂，由环己酮与异VC反应合成环己酮异VC缩酮。用正交实验获得了较优的合成条件：环己酮0．9814g（10mmol），异VC2．8179g（16mmol），对甲苯磺酸0．3804g（2mmol），DMAc 8mL，环己烷9mL，反应温度120～125℃，反应时间2．5h，标题化合物的收率为84．82％。用^1H NMR，FTIR和EI—MS确定了标题化合物的结构。参照我国规定的食品抗氧化剂最高允许浓度，将异VC、没食子酸丙酯（PG）、环己酮异VC缩酮和叔丁基对苯二酚（TBHQ）分别应用于新鲜茶籽油中进行抗氧化试验，结果表明，环己酮异VC缩酮是一种良好的油溶性抗氧化剂。例如，当异VC、PG、环己酮异VC缩酮和TBHQ添加量分别为茶籽油质量的0．02%、0．01％、0．029％和0．02％时，60℃下抗氧化试验8天后，油样的过氧化值（POV）分别为27．60、24．97、8．10和9．01meq／kg。Cyclohexanone D-isoascorbic acid ketal was synthesized from the reaction of D-isoascorbic acid and cyclohexanone with p-toluene-sulfonic acid as catalyst, N, N-dimethyl acetamide （DMAe） as solvent and cyclohexane as water carrying agent. The optimal reaction conditions determined by orthogonal experiment were as follows, cyclohexanone 0. 9814 g（10 mmol）, D-isoascorbic acid 2. 8179 g（16 mmol）, p-toluene sulfonic acid 0. 3804 g（2 mmol）, DMAc 8 mL, cyclohexane 9 mL, reaction temperature 120- 125 ℃ and reaction time 2.5 h. The yield was 84.82% under these optimal conditions. The title compound was characterized by ^1H NMR, FT IR and ELMS. The antioxidation activity of the title compound for fresh tea seed oil was evaluated by peroxide value （POV） determination. For example, when the added mass percent was 0. 02 % for D-isoascorbic acid, 0. 01% for propyl gallate （PG）, 0.029% for cyclohexanone D-isoascorbic acid ketal and 0. 020% for tert-butyl hydoquinone （TBHQ）, the POV：of the tea seed oil added D-isoascorbic acid, PG, cyclhoexanone D-isoascorbic acid ketal and TBHQ was 27.60, 24.97, 8.10 and 9.01 meq/kg, respectively, after 8 days＇ heating at 60 ℃.

关 键 词：环己酮异VC缩酮 环己酮 异VC 过氧化值 正交试验 

分 类 号：O621.256.4[理学—有机化学]