中空纤维膜液相微萃取技术及其在气相色谱中的分析应用
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摘要
在实际样品分析过程中,通常会面临因样品基质复杂而造成的干扰以及目标分析物的浓度过低或存在状态不适于直接测定等问题,必须选择合适的样品前处理技术对样品进行分离、富集、纯化,并使目标分析物转化成适合于分析测定的形式。所以,样品前处理技术已成为目前分析化学研究中的热点和难点之一。传统样品前处理技术存在有机溶剂消耗量大、费时、操作步骤繁琐等缺点。为了克服这些缺点,近年来,分析化学家们提出了一系列新型样品前处理技术。液相微萃取(Liquid-phase Microextraction, LPME)是在液-液萃取(Liquid-liquid Extraction, LLE)的基础上发展起来的一种集采样、萃取和浓缩于一体的新型样品前处理技术,具有灵敏度和富集倍数高,操作简便、快捷和消耗有机溶剂少等优点,已迅速成为样品前处理技术领域中的热点研究方向之一。中空纤维膜液相微萃取(HF-LPME)是LPME的一种操作模式,具有操作方便、重现性好、可承受高速搅拌等优点；并且纤维膜上的微孔可阻止样品溶液中的大分子和各种干扰物、杂质等进入纤维孔,还具有微滤和除杂的作用,其应用前景非常广阔。
气相色谱(Gas Chromatography, GC)具有分离性能高、选择性好、灵敏度高、操作简单、分析速度快及适用性广等优点,已成为痕量组分分析中普遍使用的分离检测工具。LPME微升级的萃取溶剂与GC微升级的进样量十分匹配,使两者的联用易于实现,在痕量有机物及无机物的分析中具有极大的应用潜力。
本论文的研究目的是,以GC为后续分离检测手段,系统地研究影响HF-LPME的主要因素并探讨其规律性；详细考察不同性质的目标分析物(中性、碱性及酸性)在微萃取体系中的萃取行为；比较不同萃取模式的优缺点；建立一系列HF-LPME与GC-火焰离子化检测器(FID)/火焰光度检测器(FPD)/质谱(MS)联用分析环境、食品和生物样品中的痕量/超痕量组分的新方法。主要研究内容包括：
(1)建立了HF-LPME-GC-FID同时测定环境水样中氯苯和溴苯类化合物的新方法。对影响HF-LPME萃取效率的因素如萃取溶剂、萃取时间、萃取温度、搅拌速度及离子强度等进行了详细考察和优化。在最佳的萃取条件下,该方法对氯苯、溴苯、间氯甲苯、1,2-二氯苯、1,2,4-三氯苯和1,3,5-三溴苯的检出限和富集倍数分别为2.38-9.48μg/L和101.7-146.1倍；各物质的线性范围达3个数量级；相对标准偏差(RSDs, n=5)为8.7-12.2%(无内标)和8.4-11.8%(内标法)。将该方法应用于东湖水和长江水中氯苯和溴苯类化合物的分析,均没有检测到目标分析物,加标回收的回收率为81.5-107.7%。
(2)建立了HF-LPME-GC-FID测定尿样中苯丙胺类、咖啡因及氯胺酮等六种新型毒品的新方法,为公、检、法、医疗部门取用尿样进行吸毒检查提供了一种新颖的技术平台。在最佳的萃取条件下,该方法对苯丙胺(AP)、甲基苯丙胺(MA)、3,4-亚甲基二氧基-N-苯丙胺(MDA)、3,4-亚甲基二氧基-N-甲基苯丙胺(MDMA)、咖啡因(Caffeine)以及氯胺酮(KT)的富集倍数和检出限分别为5-227倍和8-82μg/L,RSDs (n=7)为6.9-14.1%,方法的灵敏度足以满足实际样品中的新型毒品的分析检测要求。该方法已被成功用于吸毒嫌疑人的尿样分析,加标回收的回收率为75.2-119.3%。与毒品分析中常用的样品前处理技术(如LLE和固相萃取)相比,该方法具有操作简捷、省时和有机溶剂耗量少等优点。
(3)采用正交实验设计考察并优化了影响HF-LPME萃取七种有机防腐剂(山梨酸(SA)、苯甲酸(BA)、脱氢乙酸(DA)、对羟基苯甲酸甲酯(MP)、对羟基苯甲酸乙酯(EP)、对羟基苯甲酸丙酯(PP)以及对羟基苯甲酸丁酯(BP))萃取效率的因素,建立了HF-LPME-GC-FID测定酱油和饮料中有机防腐剂的新方法。该方法应用于酱油、可乐、柚子茶以及果啤中七种有机防腐剂的分析,其富集倍数和检出限分别为26-124倍和0.03-0.52 mg/L；线性范围达2至3个数量级。与其它用于防腐剂分析的方法相比,该方法基体耐受能力强,操作简便、分析速度快(萃取时间仅需20 min),灵敏度高。
(4)以GC-FPD为后续分离/检测手段,对HF-LPME和分散液液微萃取(DLLME)两种样品前处理方法用于六种有机硫农药(马拉硫磷,毒死蜱,噻嗪酮,三唑磷,丁硫克百威和哒螨酮)分析的最佳萃取条件、分析性能及实际样品分析等进行了考察和全面比较。结果表明,DLLME和HF-LPME两种微萃取方法均具有操作方便快速、装置简单廉价、无需复杂的样品预处理步骤、仅需微升级的有机溶剂、无交叉污染、环境友好等优点。与HF-LPME相比,DLLME在分析基体成分简单的样品时,萃取时间短、富集倍数和灵敏度高,在较短的时间内可以同时完成多个样品萃取分离的过程,适合于批量样品的处理；但相对标准偏差较大。而HF-LPME抗样品基质能力强,在分析基体成分复杂的样品时,样品无需稀释,加标回收率及重现性较好。相对而言,DLLME适合批量快速分析简单基体的样品,HF-LPME对复杂基体样品的分析具有更大优势。
(5)建立并比较了直接HF-LPME和氯甲酸乙酯原位衍生HF-LPME分别与GC联用测定尿样中海洛因及其代谢产物的新方法。在各自最佳的实验条件下,直接HF-LPME-GC-FID和原位衍生HF-LPME-GC-FID对可待因、吗啡、乙酰可待因、6-单乙酰吗啡以及海洛因的富集倍数和检出限分别为17.5-139.1倍,1.5-72.9μg/L以及4.9-22.3倍,6.5-24.8μg/L。以氯甲酸乙酯为衍生试剂的衍生反应能在室温的条件下于水相中快速地实现对海洛因代谢产物(吗啡和6-单乙酰吗啡)中酚羟基的衍生,具有操作简单、快捷的优点；但是吗啡和6-单乙酰吗啡的检出限并没有因衍生而得到明显的改善,可能是由于衍生效率不高所致。最后,将所建立的直接HF-LPME-GC-FID应用于吸毒嫌疑人尿样中海洛因及其代谢产物的分析并进行了加标回收实验,结果满意。
In real-world sample analysis, some problems are often encountered:(i) the concentration of the target analytes in samples is extremely low; (ii) the original existing forms of samples are unsuitable for direct analysis by the subsequent analytical instrument, and (iii) the possible interference results from the complex sample matrix. To solve above-mentioned problems, various sample pretreatment techniques have been employed and the development of novel sample pretreatment techniques has arose great interest and become a hot topic in the field of analytical sciences. At present, sample pretreatment techniques is towards the direction of miniaturization, simplification and extremely low solvent consumption. Liquid phase microextraction (LPME) is one of such novel sample pretreatment techniques, which integrates extraction, preconcentration and sample introduction into a single step with simple apparatus, easy operation and little solvent consumption. As one of the operation modes of LPME, hollow fiber (HF)-LPME utilizes a hollow fiber to stabilize and protect the extraction solvent, exhibiting an extra good clean-up ability of sample matrix because the micro-pores of the fiber prevent large molecules and particles from entering into the extraction phase. Besides, it can shorten the extraction time due to higher stirring rate allowed in HF-LPME. Therefore, HF-LPME has attracted more and more attention in analytical community.
Gas chromatography (GC) is one of the most powerful techniques for trace/ultratrace analysis due to its significant advantages including good separation efficiency, high selectivity, low detection limits and simple operation. Additionally, it is worthy to mention that the injection volume of GC matches the volume of extraction solvent in LPME, which makes the combination of GC with LPME very convenient.
The aim of this dissertation is to systematically investigate the effect of various parameters (such as extraction solvent, stirring rate and extraction temperature, etc.) on HF-LPME; to study the extraction behaviors of various target analytes (neutral and ionizable compounds) in HF-LPME procedure; to make a comparison of the characteristics of different extraction modes of LPME; and to develop a series of new methods by combining HF-LPME with GC for the analysis of environmental pollutants, illegal drugs and food additives in environmental, biological and food samples. The major contents are described as follows:
(1) A method based on HF-LPME-GC-flame ionization detection (FID) was developed for the determination of trace chloro-and bromobenzene compounds in environmental water samples. Type of extraction solvent, extraction time, extraction temperature, stirring rate and ionic strength were investigated and optimized to obtain the best extraction efficiency for target analytes. Under the optimal conditions, the limits of detection (LODs, S/N=3) for the six target compounds (chlorobenzene, bromobenzene, m-chlorotoluene,1, 2-dichlorobenzene,1,2,4-trichlorobenzene and 1,3,5-tribromobenzene) were in the range of 2.38-9.48μg/L with the enrichment factors (EFs) of 101.7-146.1 folds. To validate the proposed method, real water samples collected from East Lake and Yangtze River were analyzed and the recoveries of 81.5-107.7% were obtained.
(2) Taking amphetamine (AP), methamphetamine (MP), methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA), caffeine and ketamine (KT) as the target analytes, a novel method of HF-LPME-GC-FID was proposed for illegal drug analysis in urine samples. Under the optimal conditions, the LODs for the six target analytes were ranged from 0.008 mg/L (AP and KT) to 0.082 mg/L (MDA) and the RSDs (n=7) were in the range of 6.9-14.1% with the EFs of 5-227 folds. The proposed method is simple, effective, sensitive and low-cost, and provides a much more accurate and sensitive detection platform over commonly used techniques (such as immunological assay) for drug abuse analysis.
(3) The simultaneous determination of seven preservatives including sorbic acid (SA), benzoic acid (BA), dehydroacetic acid (DA) and p-hydroxybenzoic acid methyl, ethyl, propyl and butyl esters (MP, EP, PP and BP) in beverage samples was realized by the means of HF-LPME-GC-FID. Orthogonal array design (OAD) was applied to optimize the extraction conditions of HF-LPME including type of organic solvent, extraction time, extraction temperature, stirring speed and salt concentration. Under the optimal conditions, the RSDs (n=7) of 5.2-12.5% with EFs of 26-124 was obtained for target analytes, and the LODs ranging from 0.03 mg/L (PP) to 0.52 mg/L (SA) demonstrated the application feasibility of the proposed method in real sample analysis. The method of HF-LPME-GC-FID was applied to sauce and beverage samples analysis and the recoveries ranging from 73.0-115.7% with RSDs of 0.1-15.4% were obtained.
(4) Two methods of HF-LPME and dispersive liquid-liquid microextraction (DLLME) have been critically compared for the analysis of organosulphur pesticides (OSPs) in environmental and beverage samples followed by GC-flame photometric detection (FPD). Both methods were found to be simple, fast, efficient, and inexpensive. Compared with HF-LPME, DLLME exhibited less extraction time, suitability for simultaneous batch analysis and higher enrichment factors for simple samples such as water samples. While for the analysis of complicated matrix samples such as soil and beverage samples, HF-LPME was demonstrated to be more robust and more suitable. Both methods were applied to the analysis of six OSPs in different waters, soil and beverage samples, and no target OSPs was found in these samples. The recoveries of 81.7-114.4% were obtained for HF-LPME-GC-FPD and 78.5-117.2% for DLLME-GC-FPD.
(5) Direct HF-LPME and in-situ derivatization HF-LPME combined with GC were proposed and compared for the determination of trace heroin and its metabolites (including codeine, morphine, acetylcodeine,6-monoacetylmorphine) in urine samples. Under the optimal conditions, the LODs for target analytes obtained by direct HF-LPME-GC-FID and direct HF-LPME-GC-MS were 1.5-72.9μg/L and 1.4-24.5μg/L with EFs of 17.5-139.1, respectively. The LODs and the EFs of target analytes obtained by in-situ derivatization HF-LPME-GC-FID were 5.3-24.8μg/L and 4.9-22.3 folds, respectively. In-situ derivatization HF-LPME-GC-FID was simple, fast and no special equipment required, while the provided LODs for target analytes were not obviously improved over those obtained by direct HF-LPME-GC-FID, possibly due to low derivatization efficiency. Direct HF-LPME-GC-FID was applied for the determination of heroin and its metabolites in urine samples from abused suspects, and the recoveries of 68.1-99.1% were obtained.
气相色谱(Gas Chromatography, GC)具有分离性能高、选择性好、灵敏度高、操作简单、分析速度快及适用性广等优点,已成为痕量组分分析中普遍使用的分离检测工具。LPME微升级的萃取溶剂与GC微升级的进样量十分匹配,使两者的联用易于实现,在痕量有机物及无机物的分析中具有极大的应用潜力。
本论文的研究目的是,以GC为后续分离检测手段,系统地研究影响HF-LPME的主要因素并探讨其规律性；详细考察不同性质的目标分析物(中性、碱性及酸性)在微萃取体系中的萃取行为；比较不同萃取模式的优缺点；建立一系列HF-LPME与GC-火焰离子化检测器(FID)/火焰光度检测器(FPD)/质谱(MS)联用分析环境、食品和生物样品中的痕量/超痕量组分的新方法。主要研究内容包括：
(1)建立了HF-LPME-GC-FID同时测定环境水样中氯苯和溴苯类化合物的新方法。对影响HF-LPME萃取效率的因素如萃取溶剂、萃取时间、萃取温度、搅拌速度及离子强度等进行了详细考察和优化。在最佳的萃取条件下,该方法对氯苯、溴苯、间氯甲苯、1,2-二氯苯、1,2,4-三氯苯和1,3,5-三溴苯的检出限和富集倍数分别为2.38-9.48μg/L和101.7-146.1倍；各物质的线性范围达3个数量级；相对标准偏差(RSDs, n=5)为8.7-12.2%(无内标)和8.4-11.8%(内标法)。将该方法应用于东湖水和长江水中氯苯和溴苯类化合物的分析,均没有检测到目标分析物,加标回收的回收率为81.5-107.7%。
(2)建立了HF-LPME-GC-FID测定尿样中苯丙胺类、咖啡因及氯胺酮等六种新型毒品的新方法,为公、检、法、医疗部门取用尿样进行吸毒检查提供了一种新颖的技术平台。在最佳的萃取条件下,该方法对苯丙胺(AP)、甲基苯丙胺(MA)、3,4-亚甲基二氧基-N-苯丙胺(MDA)、3,4-亚甲基二氧基-N-甲基苯丙胺(MDMA)、咖啡因(Caffeine)以及氯胺酮(KT)的富集倍数和检出限分别为5-227倍和8-82μg/L,RSDs (n=7)为6.9-14.1%,方法的灵敏度足以满足实际样品中的新型毒品的分析检测要求。该方法已被成功用于吸毒嫌疑人的尿样分析,加标回收的回收率为75.2-119.3%。与毒品分析中常用的样品前处理技术(如LLE和固相萃取)相比,该方法具有操作简捷、省时和有机溶剂耗量少等优点。
(3)采用正交实验设计考察并优化了影响HF-LPME萃取七种有机防腐剂(山梨酸(SA)、苯甲酸(BA)、脱氢乙酸(DA)、对羟基苯甲酸甲酯(MP)、对羟基苯甲酸乙酯(EP)、对羟基苯甲酸丙酯(PP)以及对羟基苯甲酸丁酯(BP))萃取效率的因素,建立了HF-LPME-GC-FID测定酱油和饮料中有机防腐剂的新方法。该方法应用于酱油、可乐、柚子茶以及果啤中七种有机防腐剂的分析,其富集倍数和检出限分别为26-124倍和0.03-0.52 mg/L；线性范围达2至3个数量级。与其它用于防腐剂分析的方法相比,该方法基体耐受能力强,操作简便、分析速度快(萃取时间仅需20 min),灵敏度高。
(4)以GC-FPD为后续分离/检测手段,对HF-LPME和分散液液微萃取(DLLME)两种样品前处理方法用于六种有机硫农药(马拉硫磷,毒死蜱,噻嗪酮,三唑磷,丁硫克百威和哒螨酮)分析的最佳萃取条件、分析性能及实际样品分析等进行了考察和全面比较。结果表明,DLLME和HF-LPME两种微萃取方法均具有操作方便快速、装置简单廉价、无需复杂的样品预处理步骤、仅需微升级的有机溶剂、无交叉污染、环境友好等优点。与HF-LPME相比,DLLME在分析基体成分简单的样品时,萃取时间短、富集倍数和灵敏度高,在较短的时间内可以同时完成多个样品萃取分离的过程,适合于批量样品的处理；但相对标准偏差较大。而HF-LPME抗样品基质能力强,在分析基体成分复杂的样品时,样品无需稀释,加标回收率及重现性较好。相对而言,DLLME适合批量快速分析简单基体的样品,HF-LPME对复杂基体样品的分析具有更大优势。
(5)建立并比较了直接HF-LPME和氯甲酸乙酯原位衍生HF-LPME分别与GC联用测定尿样中海洛因及其代谢产物的新方法。在各自最佳的实验条件下,直接HF-LPME-GC-FID和原位衍生HF-LPME-GC-FID对可待因、吗啡、乙酰可待因、6-单乙酰吗啡以及海洛因的富集倍数和检出限分别为17.5-139.1倍,1.5-72.9μg/L以及4.9-22.3倍,6.5-24.8μg/L。以氯甲酸乙酯为衍生试剂的衍生反应能在室温的条件下于水相中快速地实现对海洛因代谢产物(吗啡和6-单乙酰吗啡)中酚羟基的衍生,具有操作简单、快捷的优点；但是吗啡和6-单乙酰吗啡的检出限并没有因衍生而得到明显的改善,可能是由于衍生效率不高所致。最后,将所建立的直接HF-LPME-GC-FID应用于吸毒嫌疑人尿样中海洛因及其代谢产物的分析并进行了加标回收实验,结果满意。
In real-world sample analysis, some problems are often encountered:(i) the concentration of the target analytes in samples is extremely low; (ii) the original existing forms of samples are unsuitable for direct analysis by the subsequent analytical instrument, and (iii) the possible interference results from the complex sample matrix. To solve above-mentioned problems, various sample pretreatment techniques have been employed and the development of novel sample pretreatment techniques has arose great interest and become a hot topic in the field of analytical sciences. At present, sample pretreatment techniques is towards the direction of miniaturization, simplification and extremely low solvent consumption. Liquid phase microextraction (LPME) is one of such novel sample pretreatment techniques, which integrates extraction, preconcentration and sample introduction into a single step with simple apparatus, easy operation and little solvent consumption. As one of the operation modes of LPME, hollow fiber (HF)-LPME utilizes a hollow fiber to stabilize and protect the extraction solvent, exhibiting an extra good clean-up ability of sample matrix because the micro-pores of the fiber prevent large molecules and particles from entering into the extraction phase. Besides, it can shorten the extraction time due to higher stirring rate allowed in HF-LPME. Therefore, HF-LPME has attracted more and more attention in analytical community.
Gas chromatography (GC) is one of the most powerful techniques for trace/ultratrace analysis due to its significant advantages including good separation efficiency, high selectivity, low detection limits and simple operation. Additionally, it is worthy to mention that the injection volume of GC matches the volume of extraction solvent in LPME, which makes the combination of GC with LPME very convenient.
The aim of this dissertation is to systematically investigate the effect of various parameters (such as extraction solvent, stirring rate and extraction temperature, etc.) on HF-LPME; to study the extraction behaviors of various target analytes (neutral and ionizable compounds) in HF-LPME procedure; to make a comparison of the characteristics of different extraction modes of LPME; and to develop a series of new methods by combining HF-LPME with GC for the analysis of environmental pollutants, illegal drugs and food additives in environmental, biological and food samples. The major contents are described as follows:
(1) A method based on HF-LPME-GC-flame ionization detection (FID) was developed for the determination of trace chloro-and bromobenzene compounds in environmental water samples. Type of extraction solvent, extraction time, extraction temperature, stirring rate and ionic strength were investigated and optimized to obtain the best extraction efficiency for target analytes. Under the optimal conditions, the limits of detection (LODs, S/N=3) for the six target compounds (chlorobenzene, bromobenzene, m-chlorotoluene,1, 2-dichlorobenzene,1,2,4-trichlorobenzene and 1,3,5-tribromobenzene) were in the range of 2.38-9.48μg/L with the enrichment factors (EFs) of 101.7-146.1 folds. To validate the proposed method, real water samples collected from East Lake and Yangtze River were analyzed and the recoveries of 81.5-107.7% were obtained.
(2) Taking amphetamine (AP), methamphetamine (MP), methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA), caffeine and ketamine (KT) as the target analytes, a novel method of HF-LPME-GC-FID was proposed for illegal drug analysis in urine samples. Under the optimal conditions, the LODs for the six target analytes were ranged from 0.008 mg/L (AP and KT) to 0.082 mg/L (MDA) and the RSDs (n=7) were in the range of 6.9-14.1% with the EFs of 5-227 folds. The proposed method is simple, effective, sensitive and low-cost, and provides a much more accurate and sensitive detection platform over commonly used techniques (such as immunological assay) for drug abuse analysis.
(3) The simultaneous determination of seven preservatives including sorbic acid (SA), benzoic acid (BA), dehydroacetic acid (DA) and p-hydroxybenzoic acid methyl, ethyl, propyl and butyl esters (MP, EP, PP and BP) in beverage samples was realized by the means of HF-LPME-GC-FID. Orthogonal array design (OAD) was applied to optimize the extraction conditions of HF-LPME including type of organic solvent, extraction time, extraction temperature, stirring speed and salt concentration. Under the optimal conditions, the RSDs (n=7) of 5.2-12.5% with EFs of 26-124 was obtained for target analytes, and the LODs ranging from 0.03 mg/L (PP) to 0.52 mg/L (SA) demonstrated the application feasibility of the proposed method in real sample analysis. The method of HF-LPME-GC-FID was applied to sauce and beverage samples analysis and the recoveries ranging from 73.0-115.7% with RSDs of 0.1-15.4% were obtained.
(4) Two methods of HF-LPME and dispersive liquid-liquid microextraction (DLLME) have been critically compared for the analysis of organosulphur pesticides (OSPs) in environmental and beverage samples followed by GC-flame photometric detection (FPD). Both methods were found to be simple, fast, efficient, and inexpensive. Compared with HF-LPME, DLLME exhibited less extraction time, suitability for simultaneous batch analysis and higher enrichment factors for simple samples such as water samples. While for the analysis of complicated matrix samples such as soil and beverage samples, HF-LPME was demonstrated to be more robust and more suitable. Both methods were applied to the analysis of six OSPs in different waters, soil and beverage samples, and no target OSPs was found in these samples. The recoveries of 81.7-114.4% were obtained for HF-LPME-GC-FPD and 78.5-117.2% for DLLME-GC-FPD.
(5) Direct HF-LPME and in-situ derivatization HF-LPME combined with GC were proposed and compared for the determination of trace heroin and its metabolites (including codeine, morphine, acetylcodeine,6-monoacetylmorphine) in urine samples. Under the optimal conditions, the LODs for target analytes obtained by direct HF-LPME-GC-FID and direct HF-LPME-GC-MS were 1.5-72.9μg/L and 1.4-24.5μg/L with EFs of 17.5-139.1, respectively. The LODs and the EFs of target analytes obtained by in-situ derivatization HF-LPME-GC-FID were 5.3-24.8μg/L and 4.9-22.3 folds, respectively. In-situ derivatization HF-LPME-GC-FID was simple, fast and no special equipment required, while the provided LODs for target analytes were not obviously improved over those obtained by direct HF-LPME-GC-FID, possibly due to low derivatization efficiency. Direct HF-LPME-GC-FID was applied for the determination of heroin and its metabolites in urine samples from abused suspects, and the recoveries of 68.1-99.1% were obtained.
引文
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