硅胶固定化离子液体富集分离天然产物中的活性成分
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摘要
本论文分为四个部分。
第一章综述了近年来固定化离子液体(supported ionic liquids, SIL s)在各领域中的应用进展情况,阐明了课题研究的意义及方向。
第二章制备了三种阴离子不同的硅胶固定化离子液体SiO2·Im+.Cl-Si02·Im+·PF6-和SiO2·Im+·BF4-,并对合成的固定化离子液体进行红外、元素分析、热重分析等结构表征。
第三章以合成的固定化离子液体SiO2·Im+·Cl-作为吸附剂,采用紫外分光光度法研究了吸附时间、固液比、样品浓度、上样流速对N-甲基咪唑键合硅胶固定化离子液体(SiO2·Im+·Cl-)吸附黄酮类化合物性能的影响。结果表明,受试化合物在30min内均达到吸附平衡;吸附效率随固液比增大而增大,随样品浓度增大而降低;吸附等温线与拟合的Langmuir模型吻合良好。SiO2·Im+·Cl-对染料木素、木犀草素及槲皮素的饱和吸附量分别为：47.7 mg·g-1、52.5 mg·g-1、63.2mg·g-1,上样流速在0.5～1.5 mL·min-1范围内吸附效率达90%以上；甲醇洗脱染料木素、木犀草素及槲皮素的解吸率分别为86.1%、83.3%、84.6%;解吸顺序为：染料木素、木犀草素、槲皮素。SiO2·Im+.Cl-对三种受试黄酮类化合物具有较强吸附和分离能力,有望用于黄酮类天然产物的分离纯化。
第四章研究了硅胶固定化离子液体SiO2·Im+.Cl-、SiO2·Im+.BF4-和SiO2·Im+·PF6-对金边瑞香中活性成分的富集分离特性。主要考察了固相吸附最佳富集分离条件、固定化离子液体在最佳富集分离活性组分中的残留量以及固定化离子液体的循环使用等。试验结果表明SiO2·Im+.Cl-的最佳洗脱条件为先用甲醇与乙酸乙酯混合溶剂1：5洗脱,再用甲醇洗脱；SiO2·Im+·BF4-的最佳洗脱条件为甲醇与乙酸乙酯混合溶剂1：20。SiO2·Im+·Cl-除对双白瑞香素具有较高的选择性外,对其它四种瑞香黄烷类化合物的富集效果也与SiO2·Im+·BF4-相当,SiO2·Im+·PF6-对金边瑞香提取物中主要活性成分富集效果却很弱。SiO2-Im+·Cl-和SiO2·Im+·BF4-对双黄酮和双白瑞香素的总富集率最高分别可达66.7%、65.8%,但两者之间无显著性差异。固定化离子液体在最佳洗脱组分中的残留量很低,并且该类固定化离子液体可以循环使用两次,其富集分离能力无明显变化。
There are four parts in this paper.
Chapter 1 In this section, the application of silica supported ionic liquids in various fields were reviewed.And the significance and direction of the research were also elucidated.
Chapter 2 Three kinds of silica supported ionic liquids possessing of different anions SiO2·Im+·Cl-, SiO2·Im+·PF6- and SiO2·Im+·BF4- were synthesized, and were characterized by IR, ICP, thermogravimetric analysis and elemental:analysis.
Chapter 3 Using the silica supported ionic liquid SiO2·Im+·Cl- synthesized above as absorbent, the effects of adsorption time, solid-liquid ratio, sample concentration, flow rate on the adsorption properties of silica supported ionic liquids SiO2-Im+·Cl-for flavonoids were investigated in this paper. The results indicated that the adsorption equilibrium for tested compounds was achieved within 30 min, the adsorption efficiencies of these three compounds were found to improve with the increase of solid-liquid ratio, and decrease with the increase of their concentrations. Moreover, the adsorption isotherm data of the three tested compounds were in good concordance with the Langmuir model. The saturated adsorption capacity of SiO2·Im+·Cl- for genistein, luteolin and quercetin was 47.7 mg·g-1,52.5 mg·g-1,63.2 mg·g-1 respectively. Adsorption efficiency of SiO2·Im+·Cl- could reach more than 90% at a sample flow rate of 0.5-1.5 mL·min-1. Using methanol as eluent, the saturated desorption efficiencies of genistein, luteolin and quercetin were 86.1%, 83.3%,84.6% respectively. The elution order of the three tested flavonoids was genistein, luteolin and quercetin. SiO2·Im+·Cl- had strong adsorption and separation capacity for three tested flavonoids, which was hopeful to be applied in separation and purification of naturally occurring flavonoids.
Chapter 4 The concentration and separation of silica supported-ionic liquids SiO2·Im+·Cl-, SiO2·Im+·BF4- and SiO2·Im+·PF6- for the activity components of Daphne odora var.marginata were studied, and the optimum separation condition of different silica supported-ionic liquids, residues and recycling use of the ionic liquid-modified silica were mainly investigated. The results indicated that the optimum elute conditions was methanol to ethyl acetate 1:5 and methanol in turns for SiO2·Im+·Cl-, while it was methanol to ethyl acetate 1:20 for SiO2-Im+-BF4-. They both had a certain degre concentration separation capacity to biflavones and there was only a little difference between them except that SiO2·Im+·Cl- had fairly good effect to concentration separation daphnoretin However SiO2·Im+·PF6- almost had no concentration separation capacity to activity components of Daphne odora var.marginat. The highest total concentration rate of SiO2·Im+·Cl-/BF4- could still reach 66.7%,65.8% for biflavones and daphnoretin respectively, but there was no significant difference between them. The residues of ionic liquid-modified silica in optimum elute components are low arid the ionic liquids-modified silica was recycled two times without obvious loss in the concentration separation capacity.
第一章综述了近年来固定化离子液体(supported ionic liquids, SIL s)在各领域中的应用进展情况,阐明了课题研究的意义及方向。
第二章制备了三种阴离子不同的硅胶固定化离子液体SiO2·Im+.Cl-Si02·Im+·PF6-和SiO2·Im+·BF4-,并对合成的固定化离子液体进行红外、元素分析、热重分析等结构表征。
第三章以合成的固定化离子液体SiO2·Im+·Cl-作为吸附剂,采用紫外分光光度法研究了吸附时间、固液比、样品浓度、上样流速对N-甲基咪唑键合硅胶固定化离子液体(SiO2·Im+·Cl-)吸附黄酮类化合物性能的影响。结果表明,受试化合物在30min内均达到吸附平衡;吸附效率随固液比增大而增大,随样品浓度增大而降低;吸附等温线与拟合的Langmuir模型吻合良好。SiO2·Im+·Cl-对染料木素、木犀草素及槲皮素的饱和吸附量分别为：47.7 mg·g-1、52.5 mg·g-1、63.2mg·g-1,上样流速在0.5～1.5 mL·min-1范围内吸附效率达90%以上；甲醇洗脱染料木素、木犀草素及槲皮素的解吸率分别为86.1%、83.3%、84.6%;解吸顺序为：染料木素、木犀草素、槲皮素。SiO2·Im+.Cl-对三种受试黄酮类化合物具有较强吸附和分离能力,有望用于黄酮类天然产物的分离纯化。
第四章研究了硅胶固定化离子液体SiO2·Im+.Cl-、SiO2·Im+.BF4-和SiO2·Im+·PF6-对金边瑞香中活性成分的富集分离特性。主要考察了固相吸附最佳富集分离条件、固定化离子液体在最佳富集分离活性组分中的残留量以及固定化离子液体的循环使用等。试验结果表明SiO2·Im+.Cl-的最佳洗脱条件为先用甲醇与乙酸乙酯混合溶剂1：5洗脱,再用甲醇洗脱；SiO2·Im+·BF4-的最佳洗脱条件为甲醇与乙酸乙酯混合溶剂1：20。SiO2·Im+·Cl-除对双白瑞香素具有较高的选择性外,对其它四种瑞香黄烷类化合物的富集效果也与SiO2·Im+·BF4-相当,SiO2·Im+·PF6-对金边瑞香提取物中主要活性成分富集效果却很弱。SiO2-Im+·Cl-和SiO2·Im+·BF4-对双黄酮和双白瑞香素的总富集率最高分别可达66.7%、65.8%,但两者之间无显著性差异。固定化离子液体在最佳洗脱组分中的残留量很低,并且该类固定化离子液体可以循环使用两次,其富集分离能力无明显变化。
There are four parts in this paper.
Chapter 1 In this section, the application of silica supported ionic liquids in various fields were reviewed.And the significance and direction of the research were also elucidated.
Chapter 2 Three kinds of silica supported ionic liquids possessing of different anions SiO2·Im+·Cl-, SiO2·Im+·PF6- and SiO2·Im+·BF4- were synthesized, and were characterized by IR, ICP, thermogravimetric analysis and elemental:analysis.
Chapter 3 Using the silica supported ionic liquid SiO2·Im+·Cl- synthesized above as absorbent, the effects of adsorption time, solid-liquid ratio, sample concentration, flow rate on the adsorption properties of silica supported ionic liquids SiO2-Im+·Cl-for flavonoids were investigated in this paper. The results indicated that the adsorption equilibrium for tested compounds was achieved within 30 min, the adsorption efficiencies of these three compounds were found to improve with the increase of solid-liquid ratio, and decrease with the increase of their concentrations. Moreover, the adsorption isotherm data of the three tested compounds were in good concordance with the Langmuir model. The saturated adsorption capacity of SiO2·Im+·Cl- for genistein, luteolin and quercetin was 47.7 mg·g-1,52.5 mg·g-1,63.2 mg·g-1 respectively. Adsorption efficiency of SiO2·Im+·Cl- could reach more than 90% at a sample flow rate of 0.5-1.5 mL·min-1. Using methanol as eluent, the saturated desorption efficiencies of genistein, luteolin and quercetin were 86.1%, 83.3%,84.6% respectively. The elution order of the three tested flavonoids was genistein, luteolin and quercetin. SiO2·Im+·Cl- had strong adsorption and separation capacity for three tested flavonoids, which was hopeful to be applied in separation and purification of naturally occurring flavonoids.
Chapter 4 The concentration and separation of silica supported-ionic liquids SiO2·Im+·Cl-, SiO2·Im+·BF4- and SiO2·Im+·PF6- for the activity components of Daphne odora var.marginata were studied, and the optimum separation condition of different silica supported-ionic liquids, residues and recycling use of the ionic liquid-modified silica were mainly investigated. The results indicated that the optimum elute conditions was methanol to ethyl acetate 1:5 and methanol in turns for SiO2·Im+·Cl-, while it was methanol to ethyl acetate 1:20 for SiO2-Im+-BF4-. They both had a certain degre concentration separation capacity to biflavones and there was only a little difference between them except that SiO2·Im+·Cl- had fairly good effect to concentration separation daphnoretin However SiO2·Im+·PF6- almost had no concentration separation capacity to activity components of Daphne odora var.marginat. The highest total concentration rate of SiO2·Im+·Cl-/BF4- could still reach 66.7%,65.8% for biflavones and daphnoretin respectively, but there was no significant difference between them. The residues of ionic liquid-modified silica in optimum elute components are low arid the ionic liquids-modified silica was recycled two times without obvious loss in the concentration separation capacity.
引文
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