紫外检测离子色谱法测定咪唑离子液体阳离子的研究
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摘要
建立了用离子色谱-直接紫外检测法对咪唑离子液体阳离子进行分离测定的方法。以甲烷磺酸/乙腈为流动相,羧酸型阳离子交换剂为固定相,实现了咪唑阳离子的分离和直接紫外检测。结果表明,咪唑阳离子的保留是放热过程,其同系物保留符合碳数规律。在柱温45℃,流速1.0 mL·min~(-1),以5.0 mmol·L~(-1)甲烷磺酸/乙腈(91/9,v/v)为流动相的检测条件下,1-乙基-3-甲基咪唑阳离子、1-丙基-3-甲基咪唑阳离子、1-丁基-3-甲基咪唑阳离子、1-戊基-3-甲基咪唑阳离子和1-己基-3-甲基咪唑阳离子在33 min内达到基线分离。检出限是0.09~0.43 mg·L~(-1),相对标准偏差不高于1.5%。将以上这种方法应用于实验室合成的咪唑离子液体样品的分析,加标回收率可以达到97.0%~100.7%。本方法简单、灵敏,具有较好实用性。
A method was established for the separation and detection of imidazolium ionic liquid cations by ion chromatography coupled with ultraviolet detection.The separation of imidazolium cations and direct ultraviolet detection were carried out by using methanesulfonic acid/acetonitrile as mobile phase and carboxylic acid cation exchanger as stationary phase.The results indicated that,the retention process of imidazolium cations was exothermic,the retention of imidazolium cation homologue was consistent with carbon number rules.The successful separation of 1-ethyl-3-methyl-imidazolium,1-propyl-3-methyl-imidazolium,1-butyl-3-methyl – imidazolium,1-amyl-3-methyl-imidazolium and 1-hexyl-3-methyl-imidazolium cations within 33 min was achieved under the conditions of the column temperature 45℃,at a flow rate of 1. 0 mL·min~(-1),using 5. 0 mmol·L~(-1) methanesulfonic acid/acetonitrile( 91/9,v/v)as mobile phase.The detection limits of the cations were 0. 09 ~ 0. 43 mg·L~(-1).The relative standard deviations were less than 1. 5%. The method has been applied to the determination of imidazolium ionic liquid samples synthesized in chemical laboratory with the spiked recovery rates between 97. 0% and 100. 7%. The method is simple,sensitive,and has better practicability.
A method was established for the separation and detection of imidazolium ionic liquid cations by ion chromatography coupled with ultraviolet detection.The separation of imidazolium cations and direct ultraviolet detection were carried out by using methanesulfonic acid/acetonitrile as mobile phase and carboxylic acid cation exchanger as stationary phase.The results indicated that,the retention process of imidazolium cations was exothermic,the retention of imidazolium cation homologue was consistent with carbon number rules.The successful separation of 1-ethyl-3-methyl-imidazolium,1-propyl-3-methyl-imidazolium,1-butyl-3-methyl – imidazolium,1-amyl-3-methyl-imidazolium and 1-hexyl-3-methyl-imidazolium cations within 33 min was achieved under the conditions of the column temperature 45℃,at a flow rate of 1. 0 mL·min~(-1),using 5. 0 mmol·L~(-1) methanesulfonic acid/acetonitrile( 91/9,v/v)as mobile phase.The detection limits of the cations were 0. 09 ~ 0. 43 mg·L~(-1).The relative standard deviations were less than 1. 5%. The method has been applied to the determination of imidazolium ionic liquid samples synthesized in chemical laboratory with the spiked recovery rates between 97. 0% and 100. 7%. The method is simple,sensitive,and has better practicability.
引文
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[10]孟令敏,于泓,黄旭,等.反相硅胶整体柱离子对色谱法快速测定吡啶离子液体阳离子[J].分析化学,2012,40(3):409-414.
[11]Huang X,Yu H,Dong Y J.Rapid and simultaneous determination of imidazolium and pyridinium ionic liquid cations by ion-pair chromatography using a monolithic column[J].Chin Chem Lett,2012,23(7):843-846.
[12]Gao W,Yu H.Determination of homologue imidazolium ionic liquid cations by ion chromatography using a carboxyl acid cation-exchange column with direct conductivity detection[J].Anal Lett,2011,44(5):922-931.
[13]李朦,于泓,刘峰.离子色谱法-间接紫外检测离子液体中三种含氟酸根阴离子[J].化学研究与应用,2015,27(3):251-255.
[14]Onink F,Meindersma W,Burghoff B,et al.Ion chromatography as a novel method to quantify the solubility of pyridinium ionic liquids in organic solvents[J].J Chromatogr Sci,2015,53(1):8-15.
[15]Hawkins C A,Rud A,Guthrie M L,et al.Rapid quantification of imidazolium-based ionic liquids by hydrophilic interaction liquid chromatography:Methodology and an investigation of the retention mechanisms[J].J Chromatogr A,2015,1400:54-64.
[16]Guan C,Yu H.Hydrophilic interaction liquid chromatography with indirect ultraviolet detection for the separation and quantification of pyrrolidinium ionic liquid cations[J].Chin Chem Lett,2015,26(11):1371-1375.
[17]Haddad P R,Brayan J G,Sharp G J,et al.Determination of pyrethroid residues on paddy rice by reversed-phase high-performance liquid chromatography[J].J Chromatogr A,1989,461:337-346.
[18]Ruiz-Angel M J,Berthod A.Reversed phase liquid chromatography of alkyl-imidazolium ionic liquids[J].J Chromatogr A,2006,1113(1-2):101-108.
[19]Yu H,Mou S F.Effect of temperature on the retention of amino acids and carbohydrates in high-performance anion-exchange chromatography[J].J Chromatogr A,2006,1118(1-2):118-124.
[2]王淼煜,孙艺梦,于泓,等.离子液体为流动相的液相色谱法-间接紫外检测吗啉阳离子[J].化学研究与应用,2015,27(9):1343-1348.
[3]田宗明,秦永华,金小平.离子液体催化合成2,2-二苄基取代丙二腈类化合物[J].化学研究与应用,2016,28(7):970-976.
[4]Paszkiewicz M,Stepnowski P.How should ionic liquids be analyzed[J].Curr Org Chem,2011,15(12):1873-1887.
[5]刘峰,于泓,张欣鑫.四丁基铵离子液体阳离子的离子色谱-直接电导检测法分析[J].化学研究与应用,2015,27(8):1185-1189.
[6]李红杏,于泓,张于.整体柱离子对色谱-紫外检测法快速测定对甲苯磺酸根[J].化学研究与应用,2014,26(6):957-960.
[7]Stepnowski P,Muller A,Behrend P,et al.R eversed-phase liquid chromatographic method for the determination of selectedroom-temperature ionic liquid cations[J].J Chromatogr A,2003,993(1-2):173-178.
[8]Buszewski B,Kowalska S,Stepnowski P.Influence of stationary phase properties on the separation of ionic liquid cations by RP-HPLC[J].J Anal Sci,2006,29(8):1116-1125.
[9]Ruiz-Angel M J,Berthod A.Reversed-phase liquid chromatography analysis of alkyl-imidazolium ionic liquids II.Effects of different added salts and stationary phase influence[J].J Chromatogr A,2008,1189(1-2):476-482.
[10]孟令敏,于泓,黄旭,等.反相硅胶整体柱离子对色谱法快速测定吡啶离子液体阳离子[J].分析化学,2012,40(3):409-414.
[11]Huang X,Yu H,Dong Y J.Rapid and simultaneous determination of imidazolium and pyridinium ionic liquid cations by ion-pair chromatography using a monolithic column[J].Chin Chem Lett,2012,23(7):843-846.
[12]Gao W,Yu H.Determination of homologue imidazolium ionic liquid cations by ion chromatography using a carboxyl acid cation-exchange column with direct conductivity detection[J].Anal Lett,2011,44(5):922-931.
[13]李朦,于泓,刘峰.离子色谱法-间接紫外检测离子液体中三种含氟酸根阴离子[J].化学研究与应用,2015,27(3):251-255.
[14]Onink F,Meindersma W,Burghoff B,et al.Ion chromatography as a novel method to quantify the solubility of pyridinium ionic liquids in organic solvents[J].J Chromatogr Sci,2015,53(1):8-15.
[15]Hawkins C A,Rud A,Guthrie M L,et al.Rapid quantification of imidazolium-based ionic liquids by hydrophilic interaction liquid chromatography:Methodology and an investigation of the retention mechanisms[J].J Chromatogr A,2015,1400:54-64.
[16]Guan C,Yu H.Hydrophilic interaction liquid chromatography with indirect ultraviolet detection for the separation and quantification of pyrrolidinium ionic liquid cations[J].Chin Chem Lett,2015,26(11):1371-1375.
[17]Haddad P R,Brayan J G,Sharp G J,et al.Determination of pyrethroid residues on paddy rice by reversed-phase high-performance liquid chromatography[J].J Chromatogr A,1989,461:337-346.
[18]Ruiz-Angel M J,Berthod A.Reversed phase liquid chromatography of alkyl-imidazolium ionic liquids[J].J Chromatogr A,2006,1113(1-2):101-108.
[19]Yu H,Mou S F.Effect of temperature on the retention of amino acids and carbohydrates in high-performance anion-exchange chromatography[J].J Chromatogr A,2006,1118(1-2):118-124.