2-羟基-3-叔丁基-5-甲基苄醇的制备及性能
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摘要
以2-叔丁基对甲酚、多聚甲醛为原料,乙二醇二甲醚和二甲苯为混合溶剂制备了2-羟基-3-叔丁基-5-甲基苄醇。得到的最优合成工艺条件为:反应温度为150℃,反应时间为20 h,2-叔丁基对甲酚与多聚甲醛的物质的量比为1∶20,2-叔丁基对甲酚与乙二醇二甲醚的物质的量比为1∶1.5。采用熔点测试、FTIR、~1HNMR、~(13)CNMR、HRMS、单晶测试对合成产物进行了表征和结构确定,并采用HPLC对其纯度进行了分析,采用热重分析对其热稳定性进行了评价。对2-羟基-3-叔丁基-5-甲基苄醇进行了抗氧化性能测试,结果表明:2-羟基-3-叔丁基-5-甲基苄醇具有对超氧阴离子O~(3-)、·OH及DPPH·较好的清除能力。
2-Hydroxy-3-tert-butyl-5-methylbenzyl alcohol was synthesized from 2-tert-butyl-p-cresol and paraformaldehyde using ethylene glycol dimethyl ether and xylene as mixed solvent. The optimal synthesis conditions of 2-hydroxy-3-tert-butyl-5-methylbenzyl alcohol were obtained as follows: reaction temperature 150 ℃, reaction time 20 h, molar ratio of 2-tert-butyl-p-cresol to paraformaldehyde 1∶20 and molar ratio of 2-tert-butyl-p-cresol to ethylene glycol dimethyl ether 1∶1.5. The synthetic product was characterized by melting point test, FTIR, ~1HNMR, ~(13)CNMR, HRMS and single crystal test. The purity of the synthesized product was analyzed by HPLC. The thermal stability was also investigated by using thermogravimetric analysis(TGA). The antioxidant properties of 2-hydroxy-3-tert-butyl-5-methylbenzyl alcohol were tested. The results showed that the synthesized product had good scavenging ability to superoxide O~(3-) anion, ·OH and DPPH· radical.
2-Hydroxy-3-tert-butyl-5-methylbenzyl alcohol was synthesized from 2-tert-butyl-p-cresol and paraformaldehyde using ethylene glycol dimethyl ether and xylene as mixed solvent. The optimal synthesis conditions of 2-hydroxy-3-tert-butyl-5-methylbenzyl alcohol were obtained as follows: reaction temperature 150 ℃, reaction time 20 h, molar ratio of 2-tert-butyl-p-cresol to paraformaldehyde 1∶20 and molar ratio of 2-tert-butyl-p-cresol to ethylene glycol dimethyl ether 1∶1.5. The synthetic product was characterized by melting point test, FTIR, ~1HNMR, ~(13)CNMR, HRMS and single crystal test. The purity of the synthesized product was analyzed by HPLC. The thermal stability was also investigated by using thermogravimetric analysis(TGA). The antioxidant properties of 2-hydroxy-3-tert-butyl-5-methylbenzyl alcohol were tested. The results showed that the synthesized product had good scavenging ability to superoxide O~(3-) anion, ·OH and DPPH· radical.
引文
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[3]Scott G.Atmospheric oxidation and antioxidants[M].Newyork:Elsevier Publisher,1993:10-23.
[4]Xin Mingliang(辛明亮),Zheng Bingfa(郑炳发),Ma Yujie(马玉杰),et al.Mechanisms of action and development of antioxidants[J].China Plastics(中国塑料),2011,25(8):86-90.
[5]Xue Weiguo(薛卫国),Fu Xisheng(伏喜胜),Zhou Xuguang(周旭光).Mechanism of lubricants antioxidants[J].Synthestic Lubricants(合成润滑材料),2015,42(2):42-46.
[6]Ma Yujie(马玉杰),Yu Shasha(俞莎莎),Cai Tao(蔡涛),et al.Synthesis and performance of a new type tri-hindered phenolic antioxidants[J].China Synthetic Resin and Plastics(合成树脂及塑料),2016,33(6):32-37.
[7]Lin Keyu(林科宇),Shi Yonggang(史永刚),He Yuekang(贺越康),et al.Reseach progress of antioxidants and friction improvers of lubricant[J].Contemporary Chemical Industry(当代化工),2018,42(2):372-378.
[8]Li Jie(李杰),Sun Shushi(孙书适),Xia Fei(夏飞),et al.Structure and function feature with application technique of non-symmetrical hindered phenol antioxidantal[J].Fine and Specialty Chemicals(精细与专用化学品),2011,19(9):9-13.
[9]Wang Lijuan(王立娟),Wang Jian(王鉴),Wang Yanpeng(王焱鹏),et al.Study on synthesis and properties of ester-phenolic antioxidant[J].Advances in Fine Petrochemicals(精细石油化工进展),2009,10(4):44-46.
[10]Bei Mann S,Stiftinger M,Grabmayer K,et al.Monitoring the degradation of stabilization systems in polypropylene during accelerated aging tests by liquid chromatography com bined with atmospheric pressure chemical ionization mass spectrometry[J].Polymer Degradation and Stability,2013,98(9):1655-1661.
[11]Li Peijun(李培军),Wu Manjiang(吾满江),Ai Li(艾力),et al.Synthesis and properties of 2,2’-methylenebis(4-methyl-6-α-methyl-benzyl phenol)[J].Applied Chemical Industry(应用化工),2010,39(4):554-557.
[12]Zhu Yongguo(朱永国),Wang Wenju(王文举),Huang Donghua(黄东华).Preparation of antioxidant 736 and application in PP resin[J].China Plastics Industry(塑料工业),2009,37(5):50-52.
[13]Beibmann S,Reisinger M,Reimann A,et al.High-throughput quantification of stabilizers in polymeric materials by flow injection tandem mass spectrometry[J].Rapid Communications in Mass Spectrometry Rcm,2014,28(8):939-947.
[14]Susanne B,Martin S,Klemens G,et al.Monitoring the degradation of stabilization systems in polypropylene during accelerated aging tests by liquid chromatography combined with atmospheric pressure chemical ionization mass spectrometry[J].Polymer Degradation and Stability,2013,98(9):1655-1661.
[15]Yu S,Wang Y,Ma Y,et al.Structure,thermal stability,antioxidant activity and DFT studies of trisphenols and related phenols[J].Inorganica Chimica Acta,2017,468(1):159-170.
[16]Wang Limin(王立敏),Cui Jianlan(崔建兰),Wang Shengpei(王声培),et al.Synthesis and performance of phenolic amine complex as antioxidant[J].Fine Chemicals(精细化工),2017,34(6):696-702.
[17]Casiraghi G,Casnati G,Puglia G,et al.Selective reaction between phenols and formaldehyde.a superior synthesis of salicyl alcholols[J].Cheminform,1980,11(22):124-125.
[18]Sheldrick G M.SHELXS-97:Program for crystal structure solution[D].University of G?ttingen:Germany,1997.
[19]American Society for Testing and Materials.Standard test method for thermal stability by thermogravimetry:ASTM E2550-2007[S].2007.