HPLC Determination of the Imidazole and 2 Impurities of 2-Methylimidazole and 4-Methylimidazole in Reaction Solutions in Production Process of Imidazole
摘 要
建立了高效液相色谱(HPLC)外标定量分析咪唑生产工艺中反应液中咪唑及杂质2-甲基咪唑和4-甲基咪唑含量的方法。在色谱分析中,选用Supersil-ODS-B色谱柱为固定相;选用体积比为40∶60的乙腈-离子对试剂(溶液pH为3.5,内含16 mmol·L-1十二烷基硫酸钠和17 mmol·L-1磷酸二氢钾)溶液为流动相进行等度洗脱;采用二极管阵列检测器进行检测,检测波长为210 nm。结果显示:咪唑、2-甲基咪唑及4-甲基咪唑标准曲线的线性范围均为10~100 mg·L-1,检出限(3S/N)分别为0.02,0.02,0.03 mg·L-1。咪唑在20 mg·L-1和100 mg·L-1添加水平下的平均加标回收率分别为100%,99.2%,相对标准偏差(n=8)为0.27%。用本方法对同一批反应液不同反应阶段的9个样品中咪唑进行了测定,测定值为10.11%~10.71%;杂质2-甲基咪唑有检出,但低于测定下限;杂质4-甲基咪唑未检出。与气相色谱法进行了比对,两者测定结果基本一致。试验结果表明,该方法准确度好、灵敏度高、重现性好,能够准确测定咪唑生产工艺中反应液中咪唑、2-甲基咪唑及4-甲基咪唑的含量。
Abstract
A HPLC external standard method for quantitative analysis of imidazole and the 2 impurities of 2-methylimidazole and 4-methylimidazole in reaction solutions in the production process of imidazole was established. In the HPLC analysis, Supersil-ODS-B column was selected as stationary phase, and mixture of iacetonitrile and ionic reagent solution (pH 3.5) containing 16 mmol·L-1 of sodium dodecyl sulfate and 17 mmol·L-1 of potassium dihydrogen phosphate at a volume ratio of 40:60 was used as mobile phase in isocratict elution. Diode array detector was used for detection, and the detection wavelength was 210 nm. As shown by the results, linearity ranges of standard curves of imidazole, 2-methylimidazole and 4-methylimidazole were same in the range of 10-100 mg·L-1, and detection limits (3S/N) found was 0.02, 0.02, 0.03 mg·L-1 respectively. The average recoveries found at the addition levels of 20 mg·L-1 and 100 mg·L-1 were 100% and 99.2% respectively, and RSDs (n=8) of the determined values was 0.27%. The imidazole in 9 samples of different reaction stages of the same batch of reaction solution was determined by the present method, giving determined values ranged from 10.11% to 10.71%. The impurity of 2-methylimidazole was detected, but its content was less than the lower limit of determination. 4-methylimidazole was not detected. This method was compared with the gas chromatography method, giving a consistent result. The introduced method was accurate, sensitive and reproducible, which was applied to rapidly determine imidazole, 2-methylimidazole and 4-methylimidazole in the reaction solution in the production process of imidazole.
中图分类号 O667.7 DOI 10.11973/lhjy-hx202006012
所属栏目 工作简报
基金项目
收稿日期 2019/10/21
修改稿日期
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联系人作者项曙光(xsg@qust.edu.cn)
备注王冰玉,硕士,研究方向为过程系统工程
引用该论文: WANG Bingyu,ZHAO Wenying,CAO Xiaorong,XIANG Shuguang. HPLC Determination of the Imidazole and 2 Impurities of 2-Methylimidazole and 4-Methylimidazole in Reaction Solutions in Production Process of Imidazole[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2020, 56(6): 692~695
王冰玉,赵文英,曹晓荣,项曙光. 高效液相色谱法测定咪唑生产工艺中反应液中咪唑及2种杂质2-甲基咪唑和4-甲基咪唑[J]. 理化检验-化学分册, 2020, 56(6): 692~695
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【3】姚曦.HPLC法测定唑来膦酸原料药中的有关物质[J].今日药学, 2019,29(4):231-233.
【4】吴晓伟,李芬,温静,等.高效液相色谱法测定咪唑中2-甲基咪唑和4-甲基咪唑[J].理化检验-化学分册, 2014,50(9):1146-1148.
【5】林晓珊,杭义萍,吴惠勤,等.气相色谱-串联质谱法测定焦糖色素中2-甲基咪唑和4-甲基咪唑[J].分析试验室, 2011,30(11):85-88.
【6】王颖,黄璐瑶,余晓琴,等.高效液相色谱-串联质谱法测定豆制品中3种甲基咪唑类化合物[J].中国卫生检验杂志, 2018,28(4):415-418.
【7】王春,顾传坤,马强,等.超分子溶剂分散液液微萃取/超高效液相色谱-串联质谱法测定鱼血中13种硝基咪唑类药物残留[J].分析测试学报, 2019,38(3):263-269.
【8】庞美蓉,林钦,戴明,等.超高效液相色谱-串联质谱法同步检测食品中的2-甲基咪唑及4-甲基咪唑[J].分析测试学报, 2016,35(8):943-948.
【9】WANG L Y, REN B B, LIU Y P, et al. 2-Acetyl-4-tetrahydroxybutylimidazole and 4-methylimidazole in caramel colours,vinegar and beverages in China[J]. Food Additives& Contaminants:Part B, 2015,8(3):163-168.
【10】丁涛,徐锦忠,沈崇钰,等.高效液相色谱-串联质谱联用测定蜂蜜中3种硝基咪唑类残留[J].分析化学, 2006,34(8):1206-1206.
【11】XU X B, LIU D B, YU S J, et al. Separation and determination of 4-methylimidazole, 2-methylimidazole and 5-hydroxymethylfurfural in beverages by amino trap column coupled with pulsed amperometric detection[J]. Food Chemistry, 2015,169:224-229.
【12】刘泽坤,张雪,孙晓娇,等.紫外检测离子色谱法测定咪唑离子液体阳离子的研究[J].化学研究与应用, 2018,30(6):881-886.
【13】DA SILVEIRA PETRUCI J F, PEREIRA E A, CARDOSO A A. Determination of 2-methylimidazole and 4-methylimidazole in caramel colors by capillary electrophoresis[J]. Journal of Agricultural and Food Chemistry, 2013,61(9):2263-2267.
【14】ONG C P, NG C L, LEE H K, et al. Separation of imidazole and its derivatives by capillary electrophoresis[J]. Journal of Chromatography A, 1994,686(2):319-324.
【15】刘娜,谢子立,吴小英,等.HPLC法测定克霉唑阴道片中咪唑含量的方法研究[J].广州化工, 2017,45(18):92-94.
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