离子液体液相微萃取乳制品中农兽药残留的研究
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摘要
论文选用乳制品作为样品研究基体，将离子液体选做液相微萃取溶剂，研究了离子液体微波辅助分散液液微萃取、离子液体均相液液微萃取、超声波辅助离子液体/离子液体分散液液微萃取和离子液体/十二烷基硫酸钠双水相系统微萃取的特点、性能及应用。
利用微波辅助分散离子液体微萃取高效液相色谱法对牛奶样品中三嗪类和苯脲类除草剂进行了萃取、富集、分离和检测。随着温度的升高，疏水性离子液体的黏度随之降低，在溶液中的溶解性增加。微波辅助温控法可提高萃取系统的温度，从而降低离子液体的黏度，使其在样品中分散成均匀的微小液滴，扩大萃取剂与目标分析物的接触面积，增加传质速率，进而使目标分析物的萃取回收率得到提高。
采用离子液体-均相液液微萃取高效液相色谱法对牛奶样品中氟喹诺酮类和磺胺类抗生素残留进行分离、富集和检测。利用蛋白质在一定的盐浓度和酸性条件下易沉积的原理去除牛奶样品中的蛋白质和脂肪类等杂质，从而得到澄清溶液。将亲水性离子液体[C_6MIM][BF_4]加入到样品溶液中，再将阴离子配对剂NH_4PF_6加入到溶液中进行均相萃取，得到疏水性离子液体[C_6MIM][PF_6]，而后高速离心得离子液体富集相。
超声辅助离子液体/离子液体液液分散微萃取方法被应用到萃取婴幼儿奶粉中的磺胺类抗生素残留。采用疏水性离子液体[C_6MIM][PF_4]作为萃取剂，亲水性离子液体[C_4MIM][BF_4]作为分散剂。在超声波及亲水性离子液体的作用下，[C_6MIM][PF_4]在样品溶液中分散成均匀的微小液滴，实现对目标分析物的萃取。阴离子配对剂NH_4PF_6的加入增大了离子液体与目标分析物的回收率。
应用离子液体/阴离子表面活性剂双水相微萃取高效液相色谱法检测牛奶样品中的磺胺类抗生素残留。在该双水相体系中，亲水性离子液体[C_6MIM]Cl作为阳离子表面活性剂，十二烷基硫酸钠作为阴离子表面活性剂，在适宜的浓度配比下形成双水相复配体系。依据目标分析物在两相中分配系数的差异性实现对目标分析物的分离和富集。该萃取方法不需要挥发性有机溶剂、操作简易、萃取时间较短、且富集倍数较高。
The dairy products are important nutritional foods, which contain proteins,vitamins and other nutrients, and can provide an essential developmental factor andimmunological components for the aged and infants. However, the dairy productswere polluted due to the abuse of pesticides and veterinary medicines in breeding oflivestock, which can endanger human healths. Some sensitive, simple and reliableanalytical methods were developed to determine the pesticide and veterinary medicineresidues in dairy products. The extraction, separation and concentration of theanalytes in the sample matrices were very important before chromatographic analysis.Liquid-liquid microextraction is a newly developed miniaturized sample pretreatmentmethod, in which the extraction and clean-up can be integrated with concentration.The extraction method has some advantages in respect of extraction efficiency,facility, extraction time and organic solvent consumption. Ionic liquids are a group ofnew “green” organic solvents, which have some unique physical-chemical properties,such as immeasurably low vapor pressure, high thermal stability, moderatedissolvability of organic compounds and structure adjustability. Therefore, ILs areconsidered as replacements for conventional organic solvents and widely applied inchemical fields.
In this thesis, ILs were selected as extraction solvents. The liquid phasemicroextraction coupled with high-performance liquid chromatographic detection wasapplied for the determination of pesticide and veterinary medicine residues in dairyproduces.
The determination of phenylurea and triazine herbicides in milk based onmicrowave-assisted ionic liquid microextraction (MAILME) coupled withhigh-performance liquid chromatographic separation and detection was described.The experimental parameters of the MAILE, including type and amount of ionic liquid, microwave extraction power, extraction time and salt concentration in sample,were evaluated by a univariate method and orthogonal screening. When60μLof[C_6MIM][PF_6] was used as extraction solvent the target compounds can be isolatedfrom the4mL of milk. The MAILME is quick (7min) and simple. The detectionlimits for isoproturon, monolinuron, linuron, propazine, prometryne, terbutryn andtrietazine are0.46,0.78,1.00,1.21,1.96,0.84and1.28μg·L1, respectively. Thepresent method was applied to the analysis of milk samples and the recoveries of theanalytes ranged from88.4to115.5%and relative standard deviations were lowerthan8.01%.
Ionic liquid-based homogeneous liquid–liquid microextraction (IL-basedHLLME) high-performance liquid chromatography (HPLC) was developed andapplied to the extraction, separation and determination of some antibiotics in milk.The proteins and lipids were removed by adding salt and adjusting the pH value. Thehomogeneous extraction was applied to the improvement of recoveries for IL phaseand analytes. The experimental parameters of the IL-based HLLME, including saltconcentration in sample solution, pH value of sample solution, volume of[C_6MIM][BF_4], amount of ion-pairing agent (NH_4PF_6), and extraction time, wereevaluated. The limits of detection for enoxacin, pefloxacin, norfloxacin, enrofloxacin,sulfamethoxazole and sulfadimethoxine were15.8,7.07,5.13,4.00,7.79and8.33μg·L1, respectively. When the present method was applied to the analysis of milksamples the recoveries of the analytes ranged from92.5to118.6%and relativestandard deviations were lower than6.96%.
Ultrasound-assisted ionic liquid/ionic liquid-dispersive liquid-liquidmicroextraction (UA-IL/IL-DLLME) HPLC was developed and applied to theextraction, separation and determination of sulfonamides in infant formula powderedmilk samples. The hydrophobic IL and hydrophilic IL were used as extraction solventand dispersion solvent, respectively. The extraction procedure was induced by theformation of cloudy solution, which was composed of fine drops of [C_6MIM][PF_6]dispersed entirely into sample solution with help of [C_4MIM][BF_4]. The purificationof sample and concentration of target analytes were performed simultaneously. Theintroduction of ion-pairing agent (NH_4PF_6) was beneficial to the improvement ofrecoveries for IL phase and analytes. The experimental parameters of theUA-IL/IL-DLLME, including concentration of [C_6MIM][PF_6] and [C_4MIM][BF_4] insample solution, ultrasound extraction time, pH value of sample solution and amount of ion-pairing agent (NH_4PF_6), were evaluated. The limits of detection forsulfamerazine, sulfamethizole, sulfachlorpyridazine, sulfamonomethoxine,sulfmethoxazole and sulfisoxazole were2.94,9.26,16.7,5.28,3.35and6.66μg·kg-1,respectively. When the present method was applied to the analysis of infant formulamilk powder samples, the recoveries of the analytes ranged from90.4to114.8%andrelative standard deviations were lower than7.5%. The present method wascompared with IL-based HLLME, ionic liquid-ultrasound-assistedemulsification-microextraction and ionic liquid-temperature-controlled-DLLME. Theresults indicated that the present method is more effective for the extraction of thesulfonamides in milk powder samples.
Ionic liquid/anionic surfactant-based aqueous catanionic two-phasemicroextraction (IL/AS-ACTPME) HPLC was developed and applied to theextraction, separation and determination of some antibiotics in milk. The surfactantconcentrations/compositions play an important role in the formation of this system.Meanwhile, the partition behavior of analytes was closely related to the choice ofphase system, pH for separation, and composition of salts. The experimentalparameters of the IL/AS-ACTPME, including concentration of anionic surfactants, thetype and amount of ILs, amount of Na_2HPO_4·12H_2O and (NH_4)2SO_4, samplesolutionpH value, extraction time and temperature and salt concentration wereinvestigated. The limits of detection for sulfamerazine, sulfamethizole,sulfamonomethoxine and sulfamethoxazole were4.13,3.15,3.50and3.38μg·L~(-1),respectively. When the present method was applied to the analysis of milk samples,the recoveries of the analytes ranged from93.6to112.9%and relative standarddeviations were lower than6.9%.
利用微波辅助分散离子液体微萃取高效液相色谱法对牛奶样品中三嗪类和苯脲类除草剂进行了萃取、富集、分离和检测。随着温度的升高，疏水性离子液体的黏度随之降低，在溶液中的溶解性增加。微波辅助温控法可提高萃取系统的温度，从而降低离子液体的黏度，使其在样品中分散成均匀的微小液滴，扩大萃取剂与目标分析物的接触面积，增加传质速率，进而使目标分析物的萃取回收率得到提高。
采用离子液体-均相液液微萃取高效液相色谱法对牛奶样品中氟喹诺酮类和磺胺类抗生素残留进行分离、富集和检测。利用蛋白质在一定的盐浓度和酸性条件下易沉积的原理去除牛奶样品中的蛋白质和脂肪类等杂质，从而得到澄清溶液。将亲水性离子液体[C_6MIM][BF_4]加入到样品溶液中，再将阴离子配对剂NH_4PF_6加入到溶液中进行均相萃取，得到疏水性离子液体[C_6MIM][PF_6]，而后高速离心得离子液体富集相。
超声辅助离子液体/离子液体液液分散微萃取方法被应用到萃取婴幼儿奶粉中的磺胺类抗生素残留。采用疏水性离子液体[C_6MIM][PF_4]作为萃取剂，亲水性离子液体[C_4MIM][BF_4]作为分散剂。在超声波及亲水性离子液体的作用下，[C_6MIM][PF_4]在样品溶液中分散成均匀的微小液滴，实现对目标分析物的萃取。阴离子配对剂NH_4PF_6的加入增大了离子液体与目标分析物的回收率。
应用离子液体/阴离子表面活性剂双水相微萃取高效液相色谱法检测牛奶样品中的磺胺类抗生素残留。在该双水相体系中，亲水性离子液体[C_6MIM]Cl作为阳离子表面活性剂，十二烷基硫酸钠作为阴离子表面活性剂，在适宜的浓度配比下形成双水相复配体系。依据目标分析物在两相中分配系数的差异性实现对目标分析物的分离和富集。该萃取方法不需要挥发性有机溶剂、操作简易、萃取时间较短、且富集倍数较高。
The dairy products are important nutritional foods, which contain proteins,vitamins and other nutrients, and can provide an essential developmental factor andimmunological components for the aged and infants. However, the dairy productswere polluted due to the abuse of pesticides and veterinary medicines in breeding oflivestock, which can endanger human healths. Some sensitive, simple and reliableanalytical methods were developed to determine the pesticide and veterinary medicineresidues in dairy products. The extraction, separation and concentration of theanalytes in the sample matrices were very important before chromatographic analysis.Liquid-liquid microextraction is a newly developed miniaturized sample pretreatmentmethod, in which the extraction and clean-up can be integrated with concentration.The extraction method has some advantages in respect of extraction efficiency,facility, extraction time and organic solvent consumption. Ionic liquids are a group ofnew “green” organic solvents, which have some unique physical-chemical properties,such as immeasurably low vapor pressure, high thermal stability, moderatedissolvability of organic compounds and structure adjustability. Therefore, ILs areconsidered as replacements for conventional organic solvents and widely applied inchemical fields.
In this thesis, ILs were selected as extraction solvents. The liquid phasemicroextraction coupled with high-performance liquid chromatographic detection wasapplied for the determination of pesticide and veterinary medicine residues in dairyproduces.
The determination of phenylurea and triazine herbicides in milk based onmicrowave-assisted ionic liquid microextraction (MAILME) coupled withhigh-performance liquid chromatographic separation and detection was described.The experimental parameters of the MAILE, including type and amount of ionic liquid, microwave extraction power, extraction time and salt concentration in sample,were evaluated by a univariate method and orthogonal screening. When60μLof[C_6MIM][PF_6] was used as extraction solvent the target compounds can be isolatedfrom the4mL of milk. The MAILME is quick (7min) and simple. The detectionlimits for isoproturon, monolinuron, linuron, propazine, prometryne, terbutryn andtrietazine are0.46,0.78,1.00,1.21,1.96,0.84and1.28μg·L1, respectively. Thepresent method was applied to the analysis of milk samples and the recoveries of theanalytes ranged from88.4to115.5%and relative standard deviations were lowerthan8.01%.
Ionic liquid-based homogeneous liquid–liquid microextraction (IL-basedHLLME) high-performance liquid chromatography (HPLC) was developed andapplied to the extraction, separation and determination of some antibiotics in milk.The proteins and lipids were removed by adding salt and adjusting the pH value. Thehomogeneous extraction was applied to the improvement of recoveries for IL phaseand analytes. The experimental parameters of the IL-based HLLME, including saltconcentration in sample solution, pH value of sample solution, volume of[C_6MIM][BF_4], amount of ion-pairing agent (NH_4PF_6), and extraction time, wereevaluated. The limits of detection for enoxacin, pefloxacin, norfloxacin, enrofloxacin,sulfamethoxazole and sulfadimethoxine were15.8,7.07,5.13,4.00,7.79and8.33μg·L1, respectively. When the present method was applied to the analysis of milksamples the recoveries of the analytes ranged from92.5to118.6%and relativestandard deviations were lower than6.96%.
Ultrasound-assisted ionic liquid/ionic liquid-dispersive liquid-liquidmicroextraction (UA-IL/IL-DLLME) HPLC was developed and applied to theextraction, separation and determination of sulfonamides in infant formula powderedmilk samples. The hydrophobic IL and hydrophilic IL were used as extraction solventand dispersion solvent, respectively. The extraction procedure was induced by theformation of cloudy solution, which was composed of fine drops of [C_6MIM][PF_6]dispersed entirely into sample solution with help of [C_4MIM][BF_4]. The purificationof sample and concentration of target analytes were performed simultaneously. Theintroduction of ion-pairing agent (NH_4PF_6) was beneficial to the improvement ofrecoveries for IL phase and analytes. The experimental parameters of theUA-IL/IL-DLLME, including concentration of [C_6MIM][PF_6] and [C_4MIM][BF_4] insample solution, ultrasound extraction time, pH value of sample solution and amount of ion-pairing agent (NH_4PF_6), were evaluated. The limits of detection forsulfamerazine, sulfamethizole, sulfachlorpyridazine, sulfamonomethoxine,sulfmethoxazole and sulfisoxazole were2.94,9.26,16.7,5.28,3.35and6.66μg·kg-1,respectively. When the present method was applied to the analysis of infant formulamilk powder samples, the recoveries of the analytes ranged from90.4to114.8%andrelative standard deviations were lower than7.5%. The present method wascompared with IL-based HLLME, ionic liquid-ultrasound-assistedemulsification-microextraction and ionic liquid-temperature-controlled-DLLME. Theresults indicated that the present method is more effective for the extraction of thesulfonamides in milk powder samples.
Ionic liquid/anionic surfactant-based aqueous catanionic two-phasemicroextraction (IL/AS-ACTPME) HPLC was developed and applied to theextraction, separation and determination of some antibiotics in milk. The surfactantconcentrations/compositions play an important role in the formation of this system.Meanwhile, the partition behavior of analytes was closely related to the choice ofphase system, pH for separation, and composition of salts. The experimentalparameters of the IL/AS-ACTPME, including concentration of anionic surfactants, thetype and amount of ILs, amount of Na_2HPO_4·12H_2O and (NH_4)2SO_4, samplesolutionpH value, extraction time and temperature and salt concentration wereinvestigated. The limits of detection for sulfamerazine, sulfamethizole,sulfamonomethoxine and sulfamethoxazole were4.13,3.15,3.50and3.38μg·L~(-1),respectively. When the present method was applied to the analysis of milk samples,the recoveries of the analytes ranged from93.6to112.9%and relative standarddeviations were lower than6.9%.
引文
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