多乙烯多胺桥联受阻酚类抗氧剂的合成及其清除DPPH·性能  

Synthesis and antioxidant activity of polyethylene polyamine bridged hindered phenolic antioxidants

作　　者：李翠勤[1] 李杨[1] 郭苏月 高宇新 李锋[1] LI Cuiqin;LI Yang;GUO Suyue;GAO Yuxin;LI Feng(Key Laboratory of Oil&Gas Chemical Technology,College of Chemistry and Chemical Engineering,Northeast Petroleum University Daqing 163318,Heilongjiang,China;Daqing Petrochemical Research Center,CNPC,Daqing 163714,Heilongjiang,China)

机构地区：[1]东北石油大学化学化工学院石油与天然气化工省重点实验室,黑龙江大庆163318 [2]中国石油大庆化工研究中心,黑龙江大庆163714

出　　处：《化工进展》2020年第4期1469-1477,共9页Chemical Industry and Engineering Progress

摘　　要：以二乙烯三胺和三乙烯四胺为桥联基,β-(3,5-二叔丁基-4-羟基苯基)丙酰氯为抗氧化功能基团,通过酰胺化缩合反应合成了两类具有不同对位桥联基团的受阻酚类抗氧剂。采用傅里叶红外光谱和核磁共振氢谱证实了合成的多乙烯多胺桥联受阻酚类抗氧剂的化学结构。DPPH法研究了多乙烯多胺桥联受阻酚类抗氧剂清除自由基的性能,并探索了酚羟基个数和对位桥联基结构对受阻酚类抗氧剂清除自由基性能的影响。结果表明,多乙烯多胺桥联受阻酚类抗氧剂具有良好的清除DPPH·能力,且随着抗氧剂分子中酚羟基个数的增加,清除DPPH·的活性增加,分子中含有4个酚羟基的三乙烯四胺受阻酚类抗氧剂的抗氧化效率(AE)达到2.65×10^?2 L/(mol·s)。对位桥联基结构对受阻酚类抗氧剂清除DPPH·能力有较大影响,季戊四醇为桥联基的受阻酚类抗氧剂1010清除DPPH·能力最强,其抗氧化效率(AE)为3.08×10^?2L/(mol·s);乙二胺为核的1.0代树枝状受阻酚类抗氧剂清除DPPH·能力最弱,其抗氧化效率(AE)为2.60×10^?2 L/(mol·s)。Two types of polyethylene polyamine bridged hindered phenolic antioxidants with different number of para-bridged group were synthesized by amidation condensation reaction usingβ-(3,5-di-tertbutyl-4-hydroxyphenyl)propionyl chloride as antioxidant groups and diethylenetriamine and triethylenetetramine as bridged groups,respectively.The structures of polyethylene polyamine bridged hindered phenolic antioxidants had been characterized by FTIR and 1H NMR.The antioxidant properties of polyethylene polyamine bridged hindered phenolic antioxidants were evaluated by the DPPH method,and the relationships between the free radical scavenging properties and the number of phenolic hydroxyl groups or the structure of the para-bridged groups were studied.The results showed that polyethylene polyamine bridged hindered phenolic antioxidants had a good scavenging ability on DPPH radical.As the number of the phenolic hydroxyl groups in hindered phenolic antioxidant increased,the activity of scavenging DPPH·increased.The AE value of triethylenetetramine bridged hindered phenolic antioxidant containing four phenolic hydroxyl groups was 2.65×10^-2L·mol^-1·s^-1.The para-bridged group played an important role in the scavenging DPPH·activity for hindered phenolic antioxidants.The hindered phenolic antioxidant 1010 with pentaerythritol as the bridging group had the strongest ability in scavenging DPPH·,and the AE value was 3.08×10^-2L·mol^-1·s^-1.The 1.0G dendritic antioxidants using ethylenediamine as the nuclear have the weakest DPPH·scavenging ability,and the AE value was 2.60×10^-2L·mol^-1·s^-1.

关 键 词：多乙烯多胺 受阻酚类抗氧剂 构效关系 

分 类 号：O623.738[理学—有机化学]