阴离子功能化生物柴油离子液体抗氧化剂[X][C_6H_5COO]的制备
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摘要
设计合成了两种阴离子功能化离子液体抗氧化剂([MI][C_6H_5COO]、[Ch][C_6H_5COO]),采用核磁共振氢谱、傅里叶红外光谱对其结构进行了表征,并研究了两种离子液体抗氧化剂对小桐子生物柴油抗氧化性、铜片腐蚀性和油溶性能的影响。结果表明,离子液体抗氧化剂可有效提高生物柴油氧化稳定性,在添加量为0.3‰时,[MI][C_6H_5COO]的小桐子生物柴油诱导期提高了238%,超过了中国国家标准(6 h),[Ch][C_6H_5COO]的小桐子生物柴油诱导期提高了141%,未达到中国国家标准。进一步研究了两种离子液体抗氧化剂的油溶性,油溶性能从大到小的顺序为[MI][C_6H_5COO]>[Ch][C_6H_5COO]>GA(合成离子液体抗氧化剂的原料)。实验表明,合成的两种离子液体抗氧化剂中含有亲油阳离子的[M I][C_6H_5COO]综合性能明显优于含有亲水阳离子的[Ch][C_6H_5COO]。
Two ionic liquid antioxidants([MI][C_6H_5COO],[Ch][C_6H_5COO])were designed,and synthesized,and measured by nuclear magnetic resonance spectra and Fourier infrared spectra.The effects of two ionic liquid antioxidants on the oxidation resistance,copper corrosion and oil solubility of Jatropha biodiesel were studied.The results show that ionic liquid antioxidants can effectively improve the oxidative stability of biodiesel.When the addition amount of[M I][C_6H_5COO]is 0.3‰,the induction period of Jatropha biodiesel increases by238%,exceeding the national standard(6 h).However,when the addition amount of[Ch][C_6H_5COO]is 0.3‰,the induction period of Jatropha biodiesel increases by 141%,which does not meet the national standard.The order of oil solubility from large to small is[M I][C_6H_5COO]>[Ch][C_6H_5COO]>GA(raw material for synthesizing ionic liquid antioxidants).M oreover,the experiments show that the synthetic properties of[M I][C_6H_5COO]containing lipophilic cations in the two ionic liquid antioxidants are significantly better than those containing hydrophilic cations[Ch][C_6H_5COO].
Two ionic liquid antioxidants([MI][C_6H_5COO],[Ch][C_6H_5COO])were designed,and synthesized,and measured by nuclear magnetic resonance spectra and Fourier infrared spectra.The effects of two ionic liquid antioxidants on the oxidation resistance,copper corrosion and oil solubility of Jatropha biodiesel were studied.The results show that ionic liquid antioxidants can effectively improve the oxidative stability of biodiesel.When the addition amount of[M I][C_6H_5COO]is 0.3‰,the induction period of Jatropha biodiesel increases by238%,exceeding the national standard(6 h).However,when the addition amount of[Ch][C_6H_5COO]is 0.3‰,the induction period of Jatropha biodiesel increases by 141%,which does not meet the national standard.The order of oil solubility from large to small is[M I][C_6H_5COO]>[Ch][C_6H_5COO]>GA(raw material for synthesizing ionic liquid antioxidants).M oreover,the experiments show that the synthetic properties of[M I][C_6H_5COO]containing lipophilic cations in the two ionic liquid antioxidants are significantly better than those containing hydrophilic cations[Ch][C_6H_5COO].
引文
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[9]王文治,刘冉,曹萌萌,武宇,吕建平,赵地顺.功能化离子液体催化酯化反应研究进展[J].应用化工,2018,47(3):593-598.(WANG Wen-zhi,LIU Ran,CAO Meng-meng,WU Yu,LJian-ping,ZHAO Di-shun.Research progress of esterification reaction catalyzed by functionalized ionic liquid[J].Chin J Appl Chem,2018,47(3):593-598.)
[10]王引航,李伟,罗沙,刘守新,马春慧,李坚.离子液体固载型功能材料的应用研究进展[J].化学学报,2018,76(2):85-94.(WANG Yin-hang,LI Wei,LUO Sha,LIU Shou-xin,MA Chun-hui,LI Jian.Research advances on the applications of immobilized ionic liquids functional materials[J].Acta Chim Sin,2018,76(2):85-94.)
[11]KHIRATKAR A G,BALINGE K R,PATLE D S.Transesterification of castor oil using benzimidazolium based Bronsted acid ionic liquid catalyst[J].Fuel,2018,231:458-467.
[12]ZHANG H,WU X Q,YUAN Y N.An io nic liquid functionalized graphene adsorbent with multiple adsorption mechanisms for pipette-tip solid-phase extraction of auxins in soybean sprouts[J].Food Chem,2018,265:290-297.
[13]李法社.小桐子生物柴油的超临界两步法制备及其抗氧化耐低温性的研究[D].昆明:昆明理工大学,2011.(LI Fa-she.Preparation of Jatropha biodiesel by supercritical two-step method and its anti-oxidation and low temperature resistance[D].Kunming:Kunming University of Science and Technology,2011.)
[14]王乐乐.生物柴油氧化安定性及其抗氧化剂[D].杭州:浙江工业大学,2015.(WANG Le-le.Oxidative stability of biodiesel and its antioxidants[D].Hangzhou:Zhejiang University of Technology,2015.)
[15]李法社,李明,包桂蓉,王华,杜威,苏成帅,王峥.添加剂对橡胶籽油生物柴油氧化稳定性的改进[J].过程工程学报,2014,14(1):145-150.(LI Fa-she,LI Ming,BAO Gui-rong,WANG Hua,DU Wei,SU Cheng-shuai,WANG Wei.Improvement of oxidative stability of rubber seed oil biodiesel with additives[J].Chin J Process Eng,2014,14(1):145-150.)
[16]单郑帅,李法社,包桂蓉,申加旭.8种生物柴油常温氧化稳定性的测定与优化研究[J].中国油脂,2017,42(10):106-109.(SHAN Zheng-shuai,LI Fa-she,BAO Gui-rong,SHEN Jia-xu.Determination and optimization of oxidation stability of eight kinds of biodiesels at room temperature[J].China Oils Fats,2017,42(10):106-109.)
[17]苏成帅,李法社,李明,杨学毅,包桂蓉,王华,杜威.10种抗氧化剂在生物柴油中的抗氧化和油溶性能研究[J].中国粮油学报,2015,30(5):53-57.(SU Cheng-shuai,LI Fa-she,LI Ming,YANG Xue-yi,BAO Gui-rong,WANG Hua,DU Wei.Oil-solubility property of 10 kinds of antixoidants in biodiesel[J].J Chin Cereals Oils Assoc,2015,30(5):53-57.)
[18]秦海林,于德泉.分析化学手册7A氢-1核磁共振波谱分析[M].北京:化学工业出版社,2016,10.(QIN Hai-lin,YU De-quan.Handbook of Analytical Chemistry[M].Beijing:Chemical Industry Press,2016,10.)
[19]FAZAL M A,JAKERIA M R,HASEEB A S M A.Effect of antioxidants on the stability and corrosiveness of palm biodiesel upon exposure of different metals[J].Energy,2017,135:220-226.
[20]FAZAL M A,JAKERIA M R,HASEEB A S M A.Effect of copper and mild steel on the stability of palm biodiesel properties:Acomparative study.Indus[J].Crops Prod,2014,58(0):8-14.
[21]李萍,刘国琴.几种油溶性抗氧化剂在不同油品中的抗氧化研究[J].农产品加工(创新版),2012,(6):50-55.(LI Ping,LIU Guo-qin.study on antioxidant activity and mechanism of several oil-soluble anti-oxidants in the different oils[J].Agric Prod Process,2012,(6):50-55.)
[22]陈晓迪,刘飞,徐虹.脂溶性天然抗氧化剂的研究进展[J].食品科学,2017,38(3):299-304.(CHEN Xiao-di,LIU Fei,XU Hong.State of the art of the study of natural liposoluble antioxidants[J].Food Sci,2017,38(3):299-304.)
[2]KAINAR P,王铁.柴油机燃用0#柴油、F-T柴油、生物柴油的燃烧和排放差异分析[J].科学技术与工程,2018,18(8):203-208.(KAINAR P,WANG Tie.Analysis of combustion and emission differences of 0#diesel,F-T diesel and biodiesel fueled by diesel engines[J].Sci Technol Eng,2018,18(8):203-208.)
[3]单郑帅.生物柴油氧化稳定性的测定与优化[D].昆明:昆明理工大学,2017.(SHAN Zheng-shuai.Determination and optimization of oxidative stability of biodiesel[D].Kunming:Kunming University of Science and Technology,2017.)
[4]隋猛,王霜,李法社,聂子成,刘作文,周黎,申加旭.酚胺类抗氧化剂复配对生物柴油抗氧化性能影响研究[J].中国油脂,2018,43(4):88-91.(SUI Meng,WANG Shuang,LI Fa-she,NIE Zi-cheng,LIU Zuo-wen,ZHOU Li,SHEN Jia-xu.Effect of phenolic antioxidant compound amine antioxidant on antioxidant property of biodiesel[J].China Oils Fats,2018,43(4):88-91.)
[5]李法社,李明,包桂蓉,王华,李一哲,杜威,王峥.10种抗氧化剂对小桐子生物柴油氧化稳定性的影响[J].中国油脂,2014,39(1):50-54.(LI Fa-she,LI Ming,BAO Gui-rong,WANG Hua,LI Yi-zhe,DU Wei,WANG Zheng.Effects of ten antioxidants on oxidation stability of Jatropha curcas L.biodiesel[J].China Oils Fats,2014,39(1):50-54.)
[6]李法社,包桂蓉,王华.生物柴油氧化稳定性的研究进展[J].中国油脂,2009,34(2):1-5.(LI Fa-she,BAO Gui-rong,WANG Hua.Research advance in oxidative stability of biodiesel[J].China Oils Fats,2009,34(2):1-5.)
[7]蔡镇平.功能化离子液体催化生物质高效转化研究[D].广州:华南理工大学,2016.(CAI Zhen-ping.Study on efficient conversion of biomass by catalytic ionic liquids[D].Guangzhou:South China University of Technology,2016.)
[8]潘明光.新型功能化离子液体的结构设计及其在调控酸性气体捕集的研究[D].杭州:浙江大学,2017.(PAN Ming-guang.Structural design of new functionalized ionic liquids and its research on regulation of acid gas capture[D].Hangzhou:Zhejiang University,2017.)
[9]王文治,刘冉,曹萌萌,武宇,吕建平,赵地顺.功能化离子液体催化酯化反应研究进展[J].应用化工,2018,47(3):593-598.(WANG Wen-zhi,LIU Ran,CAO Meng-meng,WU Yu,LJian-ping,ZHAO Di-shun.Research progress of esterification reaction catalyzed by functionalized ionic liquid[J].Chin J Appl Chem,2018,47(3):593-598.)
[10]王引航,李伟,罗沙,刘守新,马春慧,李坚.离子液体固载型功能材料的应用研究进展[J].化学学报,2018,76(2):85-94.(WANG Yin-hang,LI Wei,LUO Sha,LIU Shou-xin,MA Chun-hui,LI Jian.Research advances on the applications of immobilized ionic liquids functional materials[J].Acta Chim Sin,2018,76(2):85-94.)
[11]KHIRATKAR A G,BALINGE K R,PATLE D S.Transesterification of castor oil using benzimidazolium based Bronsted acid ionic liquid catalyst[J].Fuel,2018,231:458-467.
[12]ZHANG H,WU X Q,YUAN Y N.An io nic liquid functionalized graphene adsorbent with multiple adsorption mechanisms for pipette-tip solid-phase extraction of auxins in soybean sprouts[J].Food Chem,2018,265:290-297.
[13]李法社.小桐子生物柴油的超临界两步法制备及其抗氧化耐低温性的研究[D].昆明:昆明理工大学,2011.(LI Fa-she.Preparation of Jatropha biodiesel by supercritical two-step method and its anti-oxidation and low temperature resistance[D].Kunming:Kunming University of Science and Technology,2011.)
[14]王乐乐.生物柴油氧化安定性及其抗氧化剂[D].杭州:浙江工业大学,2015.(WANG Le-le.Oxidative stability of biodiesel and its antioxidants[D].Hangzhou:Zhejiang University of Technology,2015.)
[15]李法社,李明,包桂蓉,王华,杜威,苏成帅,王峥.添加剂对橡胶籽油生物柴油氧化稳定性的改进[J].过程工程学报,2014,14(1):145-150.(LI Fa-she,LI Ming,BAO Gui-rong,WANG Hua,DU Wei,SU Cheng-shuai,WANG Wei.Improvement of oxidative stability of rubber seed oil biodiesel with additives[J].Chin J Process Eng,2014,14(1):145-150.)
[16]单郑帅,李法社,包桂蓉,申加旭.8种生物柴油常温氧化稳定性的测定与优化研究[J].中国油脂,2017,42(10):106-109.(SHAN Zheng-shuai,LI Fa-she,BAO Gui-rong,SHEN Jia-xu.Determination and optimization of oxidation stability of eight kinds of biodiesels at room temperature[J].China Oils Fats,2017,42(10):106-109.)
[17]苏成帅,李法社,李明,杨学毅,包桂蓉,王华,杜威.10种抗氧化剂在生物柴油中的抗氧化和油溶性能研究[J].中国粮油学报,2015,30(5):53-57.(SU Cheng-shuai,LI Fa-she,LI Ming,YANG Xue-yi,BAO Gui-rong,WANG Hua,DU Wei.Oil-solubility property of 10 kinds of antixoidants in biodiesel[J].J Chin Cereals Oils Assoc,2015,30(5):53-57.)
[18]秦海林,于德泉.分析化学手册7A氢-1核磁共振波谱分析[M].北京:化学工业出版社,2016,10.(QIN Hai-lin,YU De-quan.Handbook of Analytical Chemistry[M].Beijing:Chemical Industry Press,2016,10.)
[19]FAZAL M A,JAKERIA M R,HASEEB A S M A.Effect of antioxidants on the stability and corrosiveness of palm biodiesel upon exposure of different metals[J].Energy,2017,135:220-226.
[20]FAZAL M A,JAKERIA M R,HASEEB A S M A.Effect of copper and mild steel on the stability of palm biodiesel properties:Acomparative study.Indus[J].Crops Prod,2014,58(0):8-14.
[21]李萍,刘国琴.几种油溶性抗氧化剂在不同油品中的抗氧化研究[J].农产品加工(创新版),2012,(6):50-55.(LI Ping,LIU Guo-qin.study on antioxidant activity and mechanism of several oil-soluble anti-oxidants in the different oils[J].Agric Prod Process,2012,(6):50-55.)
[22]陈晓迪,刘飞,徐虹.脂溶性天然抗氧化剂的研究进展[J].食品科学,2017,38(3):299-304.(CHEN Xiao-di,LIU Fei,XU Hong.State of the art of the study of natural liposoluble antioxidants[J].Food Sci,2017,38(3):299-304.)