环糊精聚合物微球及球形聚电解质刷选择性吸附苯酚和重金属离子的研究
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摘要
水污染是人类面临的主要环境污染问题之一。含环糊精的多功能材料是一种可选择性吸附苯酚的理想材料,而含巯基的纳米球形聚电解质刷则能选择性吸附重金属离子,能为吸附废水中的有害重金属开辟一条新的道路。
本文以反相悬浮聚合的方法合成了α-,β-和γ-环糊精聚合物微球,研究了其对苯酚等物质的选择性吸附、脱附及再生性能,并利用动力学及等温吸附模型对环糊精聚合物微球吸附苯酚的数据进行了拟合。球形环糊精聚合物颗粒由于其比表面积大,易于过滤分离的特点,有利于工业化生产和应用。为了增加环糊精聚合物的吸附能力,我们用光乳液聚合的方法制备了纳米球形环糊精刷,并研究了其对苯酚的选择性吸附、脱附及再生性能。为了提高吸附重金属离子的选择性,同样采用光乳液聚合的方法合成了含巯基的纳米球形聚电解质刷,并研究了其对有害重金属离子的选择性吸附、脱附及再生性能。具体研究内容和结果如下：
(1)利用反相悬浮聚合的方法制备了α-,β-和γ-环糊精聚合物微球。三种球形环糊精聚合物颗粒的形状和大小可由反相悬浮聚合反应时加入水及交联剂环氧氯丙烷的量来控制,从而得到性状可控的理想球形环糊精聚合物颗粒。
(2)由于环糊精内疏水空腔能与苯酚形成稳定的包合物,实验发现球形环糊精聚合物颗粒对苯酚表现出理想的选择性吸附性能。苯酚的吸附量可通过紫外-分光光度计测定吸附前后的浓度差来确定。球形环糊精聚合物颗粒吸附苯酚的能力主要是由环糊精的空腔大小与苯酚的匹配度来决定的,其中,β-环糊精球形聚合物颗粒吸附苯酚的效果最好。采用动力学和等温吸附平衡模型拟合了球形环糊精聚合物颗粒在水溶液中吸附苯酚的实验数据,发现其动力学符合Ho and Mckay方程,表明苯酚的吸附过程包括扩散过程和主客体的相互作用。而平衡等温数据可以用Freundlich方程很好地拟合。拟合结果表明：球形环糊精聚合物吸附苯酚的过程中,自由能变化为负值,说明α-,β-和γ-环糊精球形聚合物颗粒吸附苯酚均为自发过程。而其中p-环糊精球形聚合物颗粒的自由能最低,表明其吸附能力最好。还系统研究了α-,β-和γ-球形环糊精聚合物对苯酚、萘、对羟基苯甲酸和联苯胺的吸附,发现被吸附的有机小分子的结构尺寸与环糊精的疏水空腔的匹配度越高,其吸附效果越好。同时,氢键的存在能加强环糊精与苯酚等物质之间的作用,使吸附效果更好。球形环糊精聚合物吸附苯酚后能简单地利用乙醇在室温下进行脱附和再生,并且经过多次再生后,其吸附能力几乎不变。
(3)采用磺酰化、胺化等方法合成了含双键的改性环糊精单体,通过光乳液聚合制备了以聚苯乙烯为核表面接枝环糊精聚合物的纳米球形聚合物刷。利用动态光散射(DLS)的方法测量发现制备的纳米球形环糊精聚合物刷的粒径比聚苯乙烯核明显增大,且粒径分布均匀。由于环糊精可以通过包合作用选择性地吸附苯酚,并能在乙醇中脱附再生,制得的纳米球形环糊精刷可以选择性地吸附和回收水中的苯酚。
(4)纳米球形聚电解质刷由于存在强化的Donnan效应,可大量吸附和富集金属离子。为了提高纳米球形聚电解质刷吸附重金属离子的选择性,将巯基引入到纳米球形聚电解质刷中,采用光乳液聚合的方法合成了含巯基的多功能纳米球形聚电解质刷。利用动态光散射(DLS)和透射电镜(TEM)表征了纳米球形聚电解质巯基刷的核壳结构。吸附前后水中重金属的浓度由电感偶合等离子体原子发射光谱法(ICP-AES)测定。实验结果表明,巯基的加入不但可以提高对金属离子的吸附能力,同时还显著提高了其选择性,其对金、汞离子的吸附性比对铜、镍离子的吸附性更强。因此纳米球形共聚巯基刷可通过Donnnan效应和巯基与重金属离子的协同作用选择性吸附水中的重金属。在酸性溶液中,纳米球形共聚巯基刷吸附重金属离子后可再生,因而也可实现对贵金属离子的回收利用。含巯基的纳米球形聚电解质刷将是选择性吸附回收废水中重金属离子的理想材料。
Water pollution is one of the most serious environmental pollution problems. Cyclodextrin multifunctional materials have been widely used in the phenols adsorption and for the adsorption of heavy metal ions. Nano-sized spherical polyelectrolyte brushes containing mercapto group have opened a new path to selectively remove heavy metal ions,
a-, β-and y-Cyclodextrin (CD) spherical polymer particles were prepared by suspension polymerization. The selective adsorption and recovery of phenol and aromatic compounds by these CD spherical polymer particles were studied. The kinetics and isothermal equilibrium models were used to fit the experimental data of phenol removal. Due to the large specific surface area and ease to be separated of the CD polymer particles by filtration, they were conducive to the industrial production and application. To improve the adsorption capacity of phenol, the nano-sized spherical cyclodextrin brushes were synthesized by photo-emulsion polymerization. The selective adsorption and recovery of phenol by nano-sized spherical cyclodextrin brushes were studied. For selective removal of heavy metal ions, the nano-sized spherical thiol polyelectrolyte brushes were prepared by photo-emulsion polymerization. The selective adsorption and recovery of heavy metal ions by the nano-sized spherical thiol polyelectrolyte brushes were studied. Details for this thesis are listed as follows:
(1) Spherical particles of a-,β-and γ-CD polymers were prepared by suspension polymerization in liquid paraffin using epichlorohydrin as crosslinker. The shape and size of the polymerized CD particles were controlled by the amounts of water and crosslinker.
(2) Due to the selective inclusion associations between CDs and phenol, these CD polymer particles are suitable for phenol removal. The adsorption amount of phenol by CD polymers was determined by the UV spectrum. The phenol adsorption capacity of CD polymers was found to depend on host-guest interactions and the size match of the inner cavity of CD molecular. The β-CD polymer particles showed the best result to adsorb phenol, attributed to the best size matching. The kinetics and isothermal equilibrium models were used to fit the experimental data of phenol removal from aqueous solution using these CD polymer particles. It was found that kinetics followed the Ho and Mckay equation, suggesting that the adsorption process of phenol controlled by diffusion and the host-guest interaction between CD and phenol. Equilibrium isothermal data can be well fitted by Freundlich equation. The negative free energy change indicated the spontaneous nature of adsorption of phenol by a-, β-and y-CD spherical polymer particles, while the lowest one for β-CD polymer reflected its best adsorption ability, compared to a-and γ-CD polymer particles. The adsorption results of phenol, naphthalene, hydroxy benzoic acid and benzidine by a-,(3-and y-CD spherical polymer particles are quite different. The better size match between the structure of aromatic compounds and the cavity of the cyclodextrin match better, the higher adsorption results. The CD polymer particles can be easily recovered by extraction with ethanol at room temperature. The adsorption abilities keep almost unchanged after several cycles of regeneration.
(3) The6A-(methacryloyl)-6A-1,6-ethylenediamine-6A-deoxy-β-cylcodextrin was prepared and the nano-sized spherical β-cyclodextrin (β-CD) brushes were synthesized by photo-emulsion polymerization. The nano-sized spherical P-CD brushes were with narrow size distribution were prepared and confirmed by monitoring the size increase of polymer particles using dynamic light scattering (DLS). Since β-CD can selectively form host-guest association with phenol, the obtained nano-sized spherical brushes contain β-CD should be ideal candidate for removal or recovery of phenols from wastewater.
(4) Nano-sized spherical polyelectrolyte brush has a well-defined core-shell structure. It can absorb and concentrate heavy metals from aqueous solutions due to the enhanced Donnan effect, which is thus suitable for removing heavy metal ions in wastewater. In order to improve the selectivity of absorption of heavy metal ions by the nano-sized spherical polyelectrolyte brushes, the mercapto groups were introduced in the nano-sized spherical polyelectrolyte brushes. The nano-sized spherical thiol polyelectrolymte brushes consisting of a polystyrene core and a poly(N-acrylcysteamine-co-acrylic acid) brush shell were prepared by photo-emulsion polymerization. They have well defined core-shell structure as determined by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The amount of heavy metal ions absorbed by these thiol brushes were determined by inductively coupled plasma atomic emission spectrometry (ICP-AES). Nano-sized spherical polyelectrolyte thiol brushes showed the higher adsorption capacity to gold and mercury ions, compared to copper and nickel ions. Due to the selective coordination of mercapto group with heavy metal ions and electrostatic interactions, they were used to adsorb and concentrate heavy metal ions from aqueous solutions. They can be easily regenerated and the adsorption abilities keep almost unchanged after several cycles of regeneration. The adsorbed heavy metal ions can be recovered. Therefore, the nano-sized spherical polyelectrolyte thiol brushes are ideal candidates for selective remove heavy metal ions from wastewater.
本文以反相悬浮聚合的方法合成了α-,β-和γ-环糊精聚合物微球,研究了其对苯酚等物质的选择性吸附、脱附及再生性能,并利用动力学及等温吸附模型对环糊精聚合物微球吸附苯酚的数据进行了拟合。球形环糊精聚合物颗粒由于其比表面积大,易于过滤分离的特点,有利于工业化生产和应用。为了增加环糊精聚合物的吸附能力,我们用光乳液聚合的方法制备了纳米球形环糊精刷,并研究了其对苯酚的选择性吸附、脱附及再生性能。为了提高吸附重金属离子的选择性,同样采用光乳液聚合的方法合成了含巯基的纳米球形聚电解质刷,并研究了其对有害重金属离子的选择性吸附、脱附及再生性能。具体研究内容和结果如下：
(1)利用反相悬浮聚合的方法制备了α-,β-和γ-环糊精聚合物微球。三种球形环糊精聚合物颗粒的形状和大小可由反相悬浮聚合反应时加入水及交联剂环氧氯丙烷的量来控制,从而得到性状可控的理想球形环糊精聚合物颗粒。
(2)由于环糊精内疏水空腔能与苯酚形成稳定的包合物,实验发现球形环糊精聚合物颗粒对苯酚表现出理想的选择性吸附性能。苯酚的吸附量可通过紫外-分光光度计测定吸附前后的浓度差来确定。球形环糊精聚合物颗粒吸附苯酚的能力主要是由环糊精的空腔大小与苯酚的匹配度来决定的,其中,β-环糊精球形聚合物颗粒吸附苯酚的效果最好。采用动力学和等温吸附平衡模型拟合了球形环糊精聚合物颗粒在水溶液中吸附苯酚的实验数据,发现其动力学符合Ho and Mckay方程,表明苯酚的吸附过程包括扩散过程和主客体的相互作用。而平衡等温数据可以用Freundlich方程很好地拟合。拟合结果表明：球形环糊精聚合物吸附苯酚的过程中,自由能变化为负值,说明α-,β-和γ-环糊精球形聚合物颗粒吸附苯酚均为自发过程。而其中p-环糊精球形聚合物颗粒的自由能最低,表明其吸附能力最好。还系统研究了α-,β-和γ-球形环糊精聚合物对苯酚、萘、对羟基苯甲酸和联苯胺的吸附,发现被吸附的有机小分子的结构尺寸与环糊精的疏水空腔的匹配度越高,其吸附效果越好。同时,氢键的存在能加强环糊精与苯酚等物质之间的作用,使吸附效果更好。球形环糊精聚合物吸附苯酚后能简单地利用乙醇在室温下进行脱附和再生,并且经过多次再生后,其吸附能力几乎不变。
(3)采用磺酰化、胺化等方法合成了含双键的改性环糊精单体,通过光乳液聚合制备了以聚苯乙烯为核表面接枝环糊精聚合物的纳米球形聚合物刷。利用动态光散射(DLS)的方法测量发现制备的纳米球形环糊精聚合物刷的粒径比聚苯乙烯核明显增大,且粒径分布均匀。由于环糊精可以通过包合作用选择性地吸附苯酚,并能在乙醇中脱附再生,制得的纳米球形环糊精刷可以选择性地吸附和回收水中的苯酚。
(4)纳米球形聚电解质刷由于存在强化的Donnan效应,可大量吸附和富集金属离子。为了提高纳米球形聚电解质刷吸附重金属离子的选择性,将巯基引入到纳米球形聚电解质刷中,采用光乳液聚合的方法合成了含巯基的多功能纳米球形聚电解质刷。利用动态光散射(DLS)和透射电镜(TEM)表征了纳米球形聚电解质巯基刷的核壳结构。吸附前后水中重金属的浓度由电感偶合等离子体原子发射光谱法(ICP-AES)测定。实验结果表明,巯基的加入不但可以提高对金属离子的吸附能力,同时还显著提高了其选择性,其对金、汞离子的吸附性比对铜、镍离子的吸附性更强。因此纳米球形共聚巯基刷可通过Donnnan效应和巯基与重金属离子的协同作用选择性吸附水中的重金属。在酸性溶液中,纳米球形共聚巯基刷吸附重金属离子后可再生,因而也可实现对贵金属离子的回收利用。含巯基的纳米球形聚电解质刷将是选择性吸附回收废水中重金属离子的理想材料。
Water pollution is one of the most serious environmental pollution problems. Cyclodextrin multifunctional materials have been widely used in the phenols adsorption and for the adsorption of heavy metal ions. Nano-sized spherical polyelectrolyte brushes containing mercapto group have opened a new path to selectively remove heavy metal ions,
a-, β-and y-Cyclodextrin (CD) spherical polymer particles were prepared by suspension polymerization. The selective adsorption and recovery of phenol and aromatic compounds by these CD spherical polymer particles were studied. The kinetics and isothermal equilibrium models were used to fit the experimental data of phenol removal. Due to the large specific surface area and ease to be separated of the CD polymer particles by filtration, they were conducive to the industrial production and application. To improve the adsorption capacity of phenol, the nano-sized spherical cyclodextrin brushes were synthesized by photo-emulsion polymerization. The selective adsorption and recovery of phenol by nano-sized spherical cyclodextrin brushes were studied. For selective removal of heavy metal ions, the nano-sized spherical thiol polyelectrolyte brushes were prepared by photo-emulsion polymerization. The selective adsorption and recovery of heavy metal ions by the nano-sized spherical thiol polyelectrolyte brushes were studied. Details for this thesis are listed as follows:
(1) Spherical particles of a-,β-and γ-CD polymers were prepared by suspension polymerization in liquid paraffin using epichlorohydrin as crosslinker. The shape and size of the polymerized CD particles were controlled by the amounts of water and crosslinker.
(2) Due to the selective inclusion associations between CDs and phenol, these CD polymer particles are suitable for phenol removal. The adsorption amount of phenol by CD polymers was determined by the UV spectrum. The phenol adsorption capacity of CD polymers was found to depend on host-guest interactions and the size match of the inner cavity of CD molecular. The β-CD polymer particles showed the best result to adsorb phenol, attributed to the best size matching. The kinetics and isothermal equilibrium models were used to fit the experimental data of phenol removal from aqueous solution using these CD polymer particles. It was found that kinetics followed the Ho and Mckay equation, suggesting that the adsorption process of phenol controlled by diffusion and the host-guest interaction between CD and phenol. Equilibrium isothermal data can be well fitted by Freundlich equation. The negative free energy change indicated the spontaneous nature of adsorption of phenol by a-, β-and y-CD spherical polymer particles, while the lowest one for β-CD polymer reflected its best adsorption ability, compared to a-and γ-CD polymer particles. The adsorption results of phenol, naphthalene, hydroxy benzoic acid and benzidine by a-,(3-and y-CD spherical polymer particles are quite different. The better size match between the structure of aromatic compounds and the cavity of the cyclodextrin match better, the higher adsorption results. The CD polymer particles can be easily recovered by extraction with ethanol at room temperature. The adsorption abilities keep almost unchanged after several cycles of regeneration.
(3) The6A-(methacryloyl)-6A-1,6-ethylenediamine-6A-deoxy-β-cylcodextrin was prepared and the nano-sized spherical β-cyclodextrin (β-CD) brushes were synthesized by photo-emulsion polymerization. The nano-sized spherical P-CD brushes were with narrow size distribution were prepared and confirmed by monitoring the size increase of polymer particles using dynamic light scattering (DLS). Since β-CD can selectively form host-guest association with phenol, the obtained nano-sized spherical brushes contain β-CD should be ideal candidate for removal or recovery of phenols from wastewater.
(4) Nano-sized spherical polyelectrolyte brush has a well-defined core-shell structure. It can absorb and concentrate heavy metals from aqueous solutions due to the enhanced Donnan effect, which is thus suitable for removing heavy metal ions in wastewater. In order to improve the selectivity of absorption of heavy metal ions by the nano-sized spherical polyelectrolyte brushes, the mercapto groups were introduced in the nano-sized spherical polyelectrolyte brushes. The nano-sized spherical thiol polyelectrolymte brushes consisting of a polystyrene core and a poly(N-acrylcysteamine-co-acrylic acid) brush shell were prepared by photo-emulsion polymerization. They have well defined core-shell structure as determined by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The amount of heavy metal ions absorbed by these thiol brushes were determined by inductively coupled plasma atomic emission spectrometry (ICP-AES). Nano-sized spherical polyelectrolyte thiol brushes showed the higher adsorption capacity to gold and mercury ions, compared to copper and nickel ions. Due to the selective coordination of mercapto group with heavy metal ions and electrostatic interactions, they were used to adsorb and concentrate heavy metal ions from aqueous solutions. They can be easily regenerated and the adsorption abilities keep almost unchanged after several cycles of regeneration. The adsorbed heavy metal ions can be recovered. Therefore, the nano-sized spherical polyelectrolyte thiol brushes are ideal candidates for selective remove heavy metal ions from wastewater.
引文
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