4,4′-二(羟甲基)联苯的合成、表征与机理探究  

Synthesis,Characterization and Mechanism Exploration of 4,4′-Bis(hydroxymethyl)biphenyl

作　　者：杨涛[1] 唐璇[1] 薛珊 周宛欣 成西涛[2] YANG Tao;TANG Xuan;XUE Shan;ZHOU Wanxin;CHENG Xitao(College of Chemistry and Chemical Engineering,Xi’an Shiyou University,Xi’an 710065,China;Shaanxi Petrochemical Research and Design Institute,Xi’an 710054,China)

机构地区：[1]西安石油大学,陕西西安710065 [2]陕西省石油化工研究设计院,陕西西安710054

出　　处：《合成化学》2023年第8期580-586,共7页Chinese Journal of Synthetic Chemistry

基　　金：2019陕西省工业攻关资助项目(2019SF-263)。

摘　　要：4,4′-二(羟甲基)联苯是一种重要的化工原料,可用于合成高附加值的有机化合物或新型功能性材料。由于其特殊的结构和性质,4,4′-二(羟甲基)联苯在许多领域都具有广泛的应用和重要性。以4,4′-二(氯甲基)联苯为原料,经水解生成苄醇类化合物4,4′-二(羟甲基)联苯。采用1 H NMR,IR和HPLC对产物进行了表征,讨论了溶剂、水解剂、配料比、反应温度、反应时间和催化剂种类对产物含量和收率的影响。优化了4,4′-二(羟甲基)联苯的合成工艺,提出了可能的催化合成反应机理。结果表明:聚乙二醇作为催化剂,可与溶液中的阳离子发生络合,增强了亲核试剂的反应活性,提高了反应速率。在以PEG-600为催化剂,乙腈为溶剂,KOH为水解剂,配料比n(BCMBP)∶n(KOH)=1.0∶3.0,V(乙腈)∶V(H 2 O)=10∶1,78℃反应12 h的优化工艺下,粗产品HPLC含量可达97.2%(质量分数,下同),收率为93.9%。4,4′-bis(hydroxymethyl)biphenyl is an important chemical raw material that can be used to synthesize high value-added organic compounds or new functional materials.Due to its unique structure and properties,it has wide applications and importance in many fields.Through in-depth research on its synthesis methods and reaction mechanisms,we aim to provide technical support and innovative ideas for the development of related fields.Using 4,4′-bis(chloromethyl)biphenyl as raw material,it is hydrolyzed to generate benzyl alcohol compound-4,4′-bis(hydroxymethyl)biphenyl.The obtained product was characterized by 1 H NMR,IR,HPLC.The effects of the reaction conditions and catalysts on product content and yield were discussed.The synthesis process of 4,4′-bis(hydroxymethyl)biphenyl was optimized,and a possible reaction mechanism was proposed.The results show that polyethylene glycol as a catalyst,complexes with cations in the solution,enhancing the reaction reactivity of nucleophiles and improving the reaction rate.After 12 hours of reaction under the optimized conditions,the content of crude product reached 97.2%by HPLC,and the yield was 93.9%.

关 键 词：4 4′-二(氯甲基)联苯 4 4′-二(羟甲基)联苯 合成 表征 催化剂 反应机理 催化酯化 

分 类 号：O625.34[理学—有机化学]