芳氧基邻苯二腈的合成、表征及性质研究  

Synthesis, Characterization and Properties of Aryloxy-phthalonitrile

作　　者：尹彦冰[1] 杨杭 张迅 姜海燕[1] 马洁[1] 薛伟剑 Yin Yanbing;Yang Hang;Zhang Xun;Jiang Haiyan;Ma Jie;Xue Weijian(College of Chemistry and Chemical Engineering,Qiqihar University,Qiqihar,Heilongjiang 161006,China)

机构地区：[1]齐齐哈尔大学化学与化学工程学院,黑龙江齐齐哈尔161006

出　　处：《化学世界》2020年第10期669-672,共4页Chemical World

基　　金：黑龙江省自然科学基金(No.QC2016016);黑龙江省教育厅基本业务专项理工面上(No.135309439)资助项目。

摘　　要：以4-硝基邻苯二腈与愈创木酚、间甲酚、对羟基联苯为原料,二甲基亚砜为溶剂,氢氧化锂为催化剂,合成了4-(2-甲氧基-苯氧基)邻苯二腈(β-2MPn)、4-(3-甲基-苯氧基)邻苯二腈(β-MPn)和4-(4-苯基-苯氧基)邻苯二腈(β-BPn),通过1H NMR、FT-IR和13C NMR对产物结构进行表征,并测定了3种化合物的紫外-可见光谱及荧光光谱。结果表明,β-MPn、β-BPn相较于β-2MPn的紫外最大吸收波长和荧光最大发射波长均发生了不同程度的红移。对β-2MPn的合成进行了正交试验研究,得到最优反应条件为:反应温度30℃、反应时间72 h、4-硝基邻苯二腈与愈创木酚物质的量比为1∶1.25,产率82.9%。4-(2-Methoxy-phenoxy)phthalonitrile(β-2 MPn),4-(3-methyl-phenoxy)phthalonitrile(β-MPn)and 4-(4-phenylphenoxy)phthalonitrile(β-BPn)were successfully synthesized via nucleophilic substitution reaction by using 4-nitrophthalonitrile,guaiacol,m-cresol and p-hydroxybiphenyl as raw materials,dimethyl sulfoxide as solvent,and lithium hydroxide as catalyst.The structure of products was characterized by 1H NMR,13C NMR,FT-IR,UV/Vis and fluorescence spectroscopy.The results showed thatβ-MPn andβ-BPn have red-shift in comparison withβ-2 MPn.The orthogonal test was performed by comparing the temperature,time and amount of raw materials so that the optimal reaction conditions were obtained as follows:the reaction temperature was 30℃,the reaction time was 72 h,the mole ratio of 4-nitrophthalonitrile to guaiacol was 1∶1.25 and the yield was 82.9%.

关 键 词：芳氧基邻苯二腈 合成 表征 光谱性质 

分 类 号：O621.3[理学—有机化学]