新型苯乙烯系吸附树脂的研究
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摘要
疏水/亲水互穿聚合物网络(IPN)树脂是由一网疏水、另一网亲水的两类高分子网络通过高分子链缠结而形成的聚合物。天然药物中需分离出来的化合物、废水中需处理的有机污染物等大都既含有疏水基团、又含有亲水基团,当这类分子进入到疏水/亲水IPN组成的树脂中,分子中疏水基团与疏水性聚合物亲合性较强,分子中亲水基团与亲水性聚合物亲合性较强,因而疏水/亲水IPN组成的树脂比单独疏水性或亲水性树脂对这类分子表现出更强的吸附性。本论文将针对选定的模型分子的分子结构,通过IPN技术实现亲水性聚合物和疏水性聚合物共混,获得三种性能较好的疏水/亲水IPN树脂,并研究这类疏水/亲水IPN组成的树脂对模型分子的吸附性能。
后交联树脂有优良的吸附性能,有许多文献报道后交联树脂广阔的应用,相关产品已在不少国家工业化。纵观这些报道,在后交联树脂的制备过程中,普遍使用剧毒致癌物硝基苯作溶剂。为此,本论文的另一个着重点是用二氯乙烷为溶剂,用FeCl_3为催化剂,制备三种性能较好的带极性功能基的后交联树脂,详细研究这类后交联树脂对模型分子的吸附性能。
本论文主要研究的内容:
(1)黄连素为一类季铵型生物碱的代表,针对黄连素中具有疏水性的苯环,合成具有疏水性吸附能力的聚二乙烯基苯(PDVB)为第一网:针对黄连素中具有亲水性的季铵盐,合成具有亲水性离子交换能力的聚丙烯酸钠(PNaA)为第二网的疏水/亲水PDVB/PNaA IPN树脂。测定了树脂两网不同质量比和第二网不同交联度对树脂孔结构、黄连素吸附性能的影响;从合成的两网不同质量比和第二网不同交联度的一系列树脂中选取对黄连素吸附量最大的一种树脂,测定了该树脂对黄连素在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、吸附自由能和吸附熵。动态吸附及脱附实验表明在293 K时湿态PDVB/PNaA IPN树脂对水溶液中黄连素的饱和吸附量达到109.4mg/mL。树脂可以通过0.5%NaCl和80%乙醇混合溶液再生。
(2)水杨酸作为芳香有机酸的代表,选用水杨酸作为模型分子,针对水杨酸分子中含有疏水性的苯环,合成了疏水性具有疏水作用吸附能力的聚二乙烯基苯(PDVB)为第一网;针对水杨酸分子中含有亲水性的酚羟基、羧基,合成亲水性具有氢键作用吸附能力的聚(N-2-氨基乙基丙烯酰胺)(PNAEAM)为第二网的疏水/亲水PDVB/PNAEAM IPN树脂。测定了该树脂的孔结构、含水量、弱碱交换量和溶胀性能;测定了该树脂对水杨酸在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、自由能和熵。PDVB/PNAEAMIPN树脂对水杨酸的吸附量大于NDA-100树脂对水杨酸的吸附量。动态吸附及脱附实验表明在293 K时湿态PDVB/PNAEAM IPN树脂对水溶液中水杨酸的饱和吸附量达到46.1 mg/mL,树脂可以通过4%NaOH溶液再生。
(3)由于很多生物碱分子中含有喹啉单元,选用喹啉作为模型分子,针对喹啉分子中含有疏水性的苯环,合成了疏水性具有疏水作用吸附能力的聚二乙烯基苯(PDVB)为第一网;针对喹啉分子中含有显碱性亲水性的氮原子,合成亲水性具有氢键作用吸附能力的聚丙烯酸(PAA)为第二网的疏水/亲水PDVB/PAA IPN树脂。测定了该树脂的孔结构、含水量、弱酸交换量和溶胀性能;测定了该树脂对喹啉在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、自由能和熵。吸附动力学实验表明PDVB/PAA IPN树脂对喹啉的吸附符合一级速率方程,颗粒内扩散是吸附速率的主要控制步骤,吸附速率同时还受液膜扩散的影响,吸附动力学可采用HSDM模型加以描述。
(4)用二氯乙烷为溶剂,用FeCl_3为催化剂,用乙酰苯胺为后交联剂,详细研究了反应条件对树脂孔结构及对香兰素吸附性能的影响。从后交联反应条件的筛选可以看出,乙酰苯胺修饰的后交联树脂制备的最优条件为:用二氯乙烷为溶剂,反应温度在80℃,加入氯球质量8%的乙酰苯胺,加入氯球质量25%的无水FeCl_3,反应10-12小时。
(5)苯胺与氯球不能直接发生Friedel-Crafts反应,论文用乙酰苯胺修饰的后交联树脂水解制得了性能较好的以苯胺为交联桥的后交联树脂,并研究该后交联树脂对水杨酸的吸附性能。以苯胺为交联桥的后交联树脂对水杨酸的吸附符合Freundlich等温吸附方程。以苯胺为交联桥的后交联树脂对水杨酸的吸附动力学数据符合二级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤。在293K时以苯胺为交联桥的后交联树脂对水杨酸吸附量达到119.9 mg/mL(湿树脂),树脂可以通过6 BV(床体积)的乙醇再生。
(6)与乙酰苯胺修饰的后交联树脂相比较,用对乙酰氨基酚为后交联剂,在乙酰氨基的对位引入酚羟基可增加苯环的活性,有利于Friedel-Crafts反应的进行,从而制得比表面积更高的后交联树脂;另一方面,在乙酰氨基的对位引入酚羟基,从而制得带有乙酰氨基和酚羟基两类氢键作用位点的后交联树脂,利用树脂上多氢键作用位点提高吸附容量。用二氯乙烷为溶剂,用FeCl_3为催化剂,用对乙酰氨基酚为后交联剂,制得了性能较好的对乙酰氨基酚修饰的后交联树脂,探讨这类后交联树脂对双酚A、香兰素的吸附性能。树脂对双酚A的吸附量为75%活性炭的聚砜微球对双酚A的饱和吸附量的2.58倍。树脂对双酚A的吸附符合Freundlich等温吸附方程。树脂吸附双酚A时,吸附动力学数据符合一级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤;对乙酰氨基酚修饰的后交联树脂对香兰素的饱和吸附量达到约119.1mg/mL(湿树脂),树脂可以通过80%乙醇溶液再生。树脂吸附香兰素时吸附动力学数据符合Lagergren二级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤。
Hydrophobic-hydrophilic interpenetrating polymer network(IPN) resin is the polymer consisting of one hydrophobic network and another hydrophilic network through permanent entanglement in the macromolecular chains.The compound from the natural drug or organic contaminant in the demand of being put away is always composed of hydrophobic group and hydrophilic group.Because of the affinity of hydrophobic network for hydrophobic group and the affinity of hydrophilic network for hydrophilic group,the hydrophobic-hydrophilic IPN resin adsorb the compound composed of hydrophobic group and hydrophilic group stronger than hydrophobic resin or hydrophilic resin does.One emphasis was studied that three kinds of hydrophobic-hydrophilic IPN resin were synthesized through the compatibility of hydrophobic network and hydrophilic network with the IPN technology according to the model molecular structure.Adsorption performance of these resins for model molecular was studied further.
The hypercrosslinked resin with very good adsorption capacity was reported by a lot of literature.Correlative products of the hypercrosslinked resin have been industrialized.All was reported that poisonous and cancer-causing nitrobenzene was used for solvent in the synthesis of the hypercrosslinked resin.Another emphasis was studied that three kinds of hypercrosslinked resin modified with polarity functional group were prepared by Friedel-Crafts reaction.Dichloroethane was used as solvent and ferric chloride was used as catalyst.Adsorption performance of these resins for model molecular was investigated further.
The main contents and conclusions in this thesis are followed as:
The hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(sodium acrylate) IPN(PDVB/PNaA IPN) was prepared at the aim of adsorption for quaternary ammonium type alkaloids such as berberine.On the one hand the hydrophobic PDVB in the PDVB/PNaA IPN resin has the ability of adsorption for berberine using hydrophobic interaction,and on the other hand the hydrophilic PNaA in the PDVB/PNaA IPN resin has the ability of adsorption for berberine using ion exchange interaction.The effects of different mass ratio of the two networks and the effects of different cross-linking degree of the second network on the pore structure and adsorption capacity of PDVB/PNaA EPN resin were studied.The PDVB/PNaA IPN resin whose adsorption quantity was the biggest was chosen to study further.The pore structure,the weak acid exchange capacity,the water retention capacity,and the swelling ability of PDVB/PNaA IPN resin were measured.The study focused on the adsorption isotherms of berberine at different temperatures.Isosteric adsorption enthalpy,adsorption Gibbs free energies could be calculated according to thermodynamic functions.The results show that the saturated adsorption quantity of berberine was up to 109.4mg·mL~(-1)(wet resin) by the way of dynamic adsorption and desorption experiment at 293 K.The resin could be reused by the mixture with 0.5% sodium chloride and 80%ethanol.
For the adsorption studies salicylic acid was chosen as the representative of aromatic acids,because there is a hydrophobic benzene ring and a hydrophilic hydroxyl group in the molecule.The hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(N-2-aminoethylacrylamide) interpenetrating polymer (PDVB/PNAEAM IPN) was prepared at the aim of adsorption for salicylic acid.The hydrophobic PDVB part in PDVB/PNAEAM IPN resin has the ability of adsorption through hydrophobic interaction;on the other hand the hydrophilic PNAEAM part has the ability of adsorption by means of hydrogen bond.The pore structure,the weak base exchange capacity,the water retention capacity and the swelling ratio of PDVB/PNAEAM IPN resin were measured.The adsorption isotherms of salicylic acid at different temperatures were studied.Isothermal adsorption enthalpy,Gibbs free energy and entropy were calculated according to thermodynamic equations.The adsorption of salicylic acid onto the PDVB/PNAEAM IPN resin is better than that of NDA-100 resin.The saturated adsorption capacity for salicylic acid was up to 46.1 mg/mL(wet resin) according to the dynamic adsorption and desorption experiments at 293K.The resin can be regenerated by 4%NaOH.
For the adsorption studies quinoline was chosen as the representative,because a lot of alkaloid molecules have the unit of quinoline.Hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(acrylic acid) IPN(PDVB/PAA IPN) was prepared at the aim of adsorption for quinoline,which was composed of two networks, one was hydrophobic PDVB,the other was hydrophilic PAA.The hydrophobic PDVB part in PDVB/PAA IPN resin had the ability of adsorption through hydrophobic interaction;on the other hand the hydrophilic PAA part has the ability of adsorption by means of hydrogen bond.The pore structure,the weak acid exchange capacity,the water retention capacity and the swelling ratio of PDVB/PAA IPN resin were measured.The research focused on the adsorption isotherms of quinoline at different temperatures.Isosteric adsorption enthalpy,adsorption Gibbs free energies and adsorption entropy could be calculated according to thermodynamic functions.The adsorption kinetic date fitted to the Lagerren first order rate equation.Intrapartical diffusion was the rate controlling step and could be described by HSDM model.
The hypercrosslinked resin modified with acetylaniline was synthesised with chloromethylated polystyrene and acetylaniline by Friedel-Crafts reaction. Dichloroethane was used as solvent and ferric chloride was used as catalyst.The research focused on the effects of reaction conditions on the pore structures of resin and the adsorption capacity for vanillin.The results showed that the optimum reaction condition was attained as follows:the reaction temperature 80℃,8%mass ratio of acetylaniline to chloromethylated polystyrene,25%mass ratio of ferric chloride to chloromethylated polystyrene,reaction time 10-12h.
Because Aniline can not react with chloromethylated polystyrene,The hypercrosslinked resin with aniline as crosslinked bridge was synthesised by the hydrolysis of the hypercrosslinked resin modified with acetylaniline.Adsorption performance of the resin for salicylic acid was studied further.The research focused on the adsorption isotherms of salicylic acid at different temperatures,which fitted well into Freundlich adsorption equation.The adsorption kinetic date fitted to the Lagerren second order rate equation.Intrapartical diffusion was the main rate-controlling step.The results showed that the saturated adsorption quantity of salicylic acid was up to 119.9mgmL~(-1)(wet resin) at 293K.The resin could be reused by 6BV ethanol.
Compared with the hypercrosslinked resin modified with acetylaniline,the hypercrosslinked resin modified by acetaminophen could be enhanced the surface area because the phenolic hydroxyl group of acetaminophen could improve the action of benzene ring;The hypercrosslinked resin modified by acetaminophen could be enhanced the adsorption capacity because of the hydrogen bond site of acetamino group and hydroxyl group.The hypercrosslinked resin modified with acetaminophen was synthesised with chloromethylated polystyrene and acetaminophen by Friedel-Crafts reaction.Dichloroethane was used as solvent and ferric chloride was used as catalyst.The objective of this work was to study the adsorption thermodynamics and adsorption kinetic of the kind of hypercrosslinked resin.The adsorption capacity for bisphenol A onto the hypercrosslinked resin modified by acetaminophen is 2.58 times as high as that of polysulphone micro-ball embedded with activated carbon.The adsorption isotherms of bisphenol A at different temperatures fitted well into Freundlich adsorption equation.The adsorption kinetic date of bisphenol A fitted to the first order rate equation.The intrapartical diffusion of bisphenol A was the main rate-controlling step.The results showed that the saturated adsorption quantity of vanillin was up to 119.1mg·mL~(-1)(wet resin) at 293K.The resin could be reused by 80%ethanol.The adsorption kinetic date of vanillin fitted to the second order rate equation.The intrapartical diffusion of vanillin was the main rate-controlling step.
后交联树脂有优良的吸附性能,有许多文献报道后交联树脂广阔的应用,相关产品已在不少国家工业化。纵观这些报道,在后交联树脂的制备过程中,普遍使用剧毒致癌物硝基苯作溶剂。为此,本论文的另一个着重点是用二氯乙烷为溶剂,用FeCl_3为催化剂,制备三种性能较好的带极性功能基的后交联树脂,详细研究这类后交联树脂对模型分子的吸附性能。
本论文主要研究的内容:
(1)黄连素为一类季铵型生物碱的代表,针对黄连素中具有疏水性的苯环,合成具有疏水性吸附能力的聚二乙烯基苯(PDVB)为第一网:针对黄连素中具有亲水性的季铵盐,合成具有亲水性离子交换能力的聚丙烯酸钠(PNaA)为第二网的疏水/亲水PDVB/PNaA IPN树脂。测定了树脂两网不同质量比和第二网不同交联度对树脂孔结构、黄连素吸附性能的影响;从合成的两网不同质量比和第二网不同交联度的一系列树脂中选取对黄连素吸附量最大的一种树脂,测定了该树脂对黄连素在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、吸附自由能和吸附熵。动态吸附及脱附实验表明在293 K时湿态PDVB/PNaA IPN树脂对水溶液中黄连素的饱和吸附量达到109.4mg/mL。树脂可以通过0.5%NaCl和80%乙醇混合溶液再生。
(2)水杨酸作为芳香有机酸的代表,选用水杨酸作为模型分子,针对水杨酸分子中含有疏水性的苯环,合成了疏水性具有疏水作用吸附能力的聚二乙烯基苯(PDVB)为第一网;针对水杨酸分子中含有亲水性的酚羟基、羧基,合成亲水性具有氢键作用吸附能力的聚(N-2-氨基乙基丙烯酰胺)(PNAEAM)为第二网的疏水/亲水PDVB/PNAEAM IPN树脂。测定了该树脂的孔结构、含水量、弱碱交换量和溶胀性能;测定了该树脂对水杨酸在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、自由能和熵。PDVB/PNAEAMIPN树脂对水杨酸的吸附量大于NDA-100树脂对水杨酸的吸附量。动态吸附及脱附实验表明在293 K时湿态PDVB/PNAEAM IPN树脂对水溶液中水杨酸的饱和吸附量达到46.1 mg/mL,树脂可以通过4%NaOH溶液再生。
(3)由于很多生物碱分子中含有喹啉单元,选用喹啉作为模型分子,针对喹啉分子中含有疏水性的苯环,合成了疏水性具有疏水作用吸附能力的聚二乙烯基苯(PDVB)为第一网;针对喹啉分子中含有显碱性亲水性的氮原子,合成亲水性具有氢键作用吸附能力的聚丙烯酸(PAA)为第二网的疏水/亲水PDVB/PAA IPN树脂。测定了该树脂的孔结构、含水量、弱酸交换量和溶胀性能;测定了该树脂对喹啉在不同温度下的吸附等温线,利用热力学函数关系计算出了吸附焓、自由能和熵。吸附动力学实验表明PDVB/PAA IPN树脂对喹啉的吸附符合一级速率方程,颗粒内扩散是吸附速率的主要控制步骤,吸附速率同时还受液膜扩散的影响,吸附动力学可采用HSDM模型加以描述。
(4)用二氯乙烷为溶剂,用FeCl_3为催化剂,用乙酰苯胺为后交联剂,详细研究了反应条件对树脂孔结构及对香兰素吸附性能的影响。从后交联反应条件的筛选可以看出,乙酰苯胺修饰的后交联树脂制备的最优条件为:用二氯乙烷为溶剂,反应温度在80℃,加入氯球质量8%的乙酰苯胺,加入氯球质量25%的无水FeCl_3,反应10-12小时。
(5)苯胺与氯球不能直接发生Friedel-Crafts反应,论文用乙酰苯胺修饰的后交联树脂水解制得了性能较好的以苯胺为交联桥的后交联树脂,并研究该后交联树脂对水杨酸的吸附性能。以苯胺为交联桥的后交联树脂对水杨酸的吸附符合Freundlich等温吸附方程。以苯胺为交联桥的后交联树脂对水杨酸的吸附动力学数据符合二级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤。在293K时以苯胺为交联桥的后交联树脂对水杨酸吸附量达到119.9 mg/mL(湿树脂),树脂可以通过6 BV(床体积)的乙醇再生。
(6)与乙酰苯胺修饰的后交联树脂相比较,用对乙酰氨基酚为后交联剂,在乙酰氨基的对位引入酚羟基可增加苯环的活性,有利于Friedel-Crafts反应的进行,从而制得比表面积更高的后交联树脂;另一方面,在乙酰氨基的对位引入酚羟基,从而制得带有乙酰氨基和酚羟基两类氢键作用位点的后交联树脂,利用树脂上多氢键作用位点提高吸附容量。用二氯乙烷为溶剂,用FeCl_3为催化剂,用对乙酰氨基酚为后交联剂,制得了性能较好的对乙酰氨基酚修饰的后交联树脂,探讨这类后交联树脂对双酚A、香兰素的吸附性能。树脂对双酚A的吸附量为75%活性炭的聚砜微球对双酚A的饱和吸附量的2.58倍。树脂对双酚A的吸附符合Freundlich等温吸附方程。树脂吸附双酚A时,吸附动力学数据符合一级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤;对乙酰氨基酚修饰的后交联树脂对香兰素的饱和吸附量达到约119.1mg/mL(湿树脂),树脂可以通过80%乙醇溶液再生。树脂吸附香兰素时吸附动力学数据符合Lagergren二级吸附速率方程,颗粒内扩散是吸附速率的主要控制步骤。
Hydrophobic-hydrophilic interpenetrating polymer network(IPN) resin is the polymer consisting of one hydrophobic network and another hydrophilic network through permanent entanglement in the macromolecular chains.The compound from the natural drug or organic contaminant in the demand of being put away is always composed of hydrophobic group and hydrophilic group.Because of the affinity of hydrophobic network for hydrophobic group and the affinity of hydrophilic network for hydrophilic group,the hydrophobic-hydrophilic IPN resin adsorb the compound composed of hydrophobic group and hydrophilic group stronger than hydrophobic resin or hydrophilic resin does.One emphasis was studied that three kinds of hydrophobic-hydrophilic IPN resin were synthesized through the compatibility of hydrophobic network and hydrophilic network with the IPN technology according to the model molecular structure.Adsorption performance of these resins for model molecular was studied further.
The hypercrosslinked resin with very good adsorption capacity was reported by a lot of literature.Correlative products of the hypercrosslinked resin have been industrialized.All was reported that poisonous and cancer-causing nitrobenzene was used for solvent in the synthesis of the hypercrosslinked resin.Another emphasis was studied that three kinds of hypercrosslinked resin modified with polarity functional group were prepared by Friedel-Crafts reaction.Dichloroethane was used as solvent and ferric chloride was used as catalyst.Adsorption performance of these resins for model molecular was investigated further.
The main contents and conclusions in this thesis are followed as:
The hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(sodium acrylate) IPN(PDVB/PNaA IPN) was prepared at the aim of adsorption for quaternary ammonium type alkaloids such as berberine.On the one hand the hydrophobic PDVB in the PDVB/PNaA IPN resin has the ability of adsorption for berberine using hydrophobic interaction,and on the other hand the hydrophilic PNaA in the PDVB/PNaA IPN resin has the ability of adsorption for berberine using ion exchange interaction.The effects of different mass ratio of the two networks and the effects of different cross-linking degree of the second network on the pore structure and adsorption capacity of PDVB/PNaA EPN resin were studied.The PDVB/PNaA IPN resin whose adsorption quantity was the biggest was chosen to study further.The pore structure,the weak acid exchange capacity,the water retention capacity,and the swelling ability of PDVB/PNaA IPN resin were measured.The study focused on the adsorption isotherms of berberine at different temperatures.Isosteric adsorption enthalpy,adsorption Gibbs free energies could be calculated according to thermodynamic functions.The results show that the saturated adsorption quantity of berberine was up to 109.4mg·mL~(-1)(wet resin) by the way of dynamic adsorption and desorption experiment at 293 K.The resin could be reused by the mixture with 0.5% sodium chloride and 80%ethanol.
For the adsorption studies salicylic acid was chosen as the representative of aromatic acids,because there is a hydrophobic benzene ring and a hydrophilic hydroxyl group in the molecule.The hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(N-2-aminoethylacrylamide) interpenetrating polymer (PDVB/PNAEAM IPN) was prepared at the aim of adsorption for salicylic acid.The hydrophobic PDVB part in PDVB/PNAEAM IPN resin has the ability of adsorption through hydrophobic interaction;on the other hand the hydrophilic PNAEAM part has the ability of adsorption by means of hydrogen bond.The pore structure,the weak base exchange capacity,the water retention capacity and the swelling ratio of PDVB/PNAEAM IPN resin were measured.The adsorption isotherms of salicylic acid at different temperatures were studied.Isothermal adsorption enthalpy,Gibbs free energy and entropy were calculated according to thermodynamic equations.The adsorption of salicylic acid onto the PDVB/PNAEAM IPN resin is better than that of NDA-100 resin.The saturated adsorption capacity for salicylic acid was up to 46.1 mg/mL(wet resin) according to the dynamic adsorption and desorption experiments at 293K.The resin can be regenerated by 4%NaOH.
For the adsorption studies quinoline was chosen as the representative,because a lot of alkaloid molecules have the unit of quinoline.Hydrophobic-hydrophilic macroporous polydivinylbenzene/poly(acrylic acid) IPN(PDVB/PAA IPN) was prepared at the aim of adsorption for quinoline,which was composed of two networks, one was hydrophobic PDVB,the other was hydrophilic PAA.The hydrophobic PDVB part in PDVB/PAA IPN resin had the ability of adsorption through hydrophobic interaction;on the other hand the hydrophilic PAA part has the ability of adsorption by means of hydrogen bond.The pore structure,the weak acid exchange capacity,the water retention capacity and the swelling ratio of PDVB/PAA IPN resin were measured.The research focused on the adsorption isotherms of quinoline at different temperatures.Isosteric adsorption enthalpy,adsorption Gibbs free energies and adsorption entropy could be calculated according to thermodynamic functions.The adsorption kinetic date fitted to the Lagerren first order rate equation.Intrapartical diffusion was the rate controlling step and could be described by HSDM model.
The hypercrosslinked resin modified with acetylaniline was synthesised with chloromethylated polystyrene and acetylaniline by Friedel-Crafts reaction. Dichloroethane was used as solvent and ferric chloride was used as catalyst.The research focused on the effects of reaction conditions on the pore structures of resin and the adsorption capacity for vanillin.The results showed that the optimum reaction condition was attained as follows:the reaction temperature 80℃,8%mass ratio of acetylaniline to chloromethylated polystyrene,25%mass ratio of ferric chloride to chloromethylated polystyrene,reaction time 10-12h.
Because Aniline can not react with chloromethylated polystyrene,The hypercrosslinked resin with aniline as crosslinked bridge was synthesised by the hydrolysis of the hypercrosslinked resin modified with acetylaniline.Adsorption performance of the resin for salicylic acid was studied further.The research focused on the adsorption isotherms of salicylic acid at different temperatures,which fitted well into Freundlich adsorption equation.The adsorption kinetic date fitted to the Lagerren second order rate equation.Intrapartical diffusion was the main rate-controlling step.The results showed that the saturated adsorption quantity of salicylic acid was up to 119.9mgmL~(-1)(wet resin) at 293K.The resin could be reused by 6BV ethanol.
Compared with the hypercrosslinked resin modified with acetylaniline,the hypercrosslinked resin modified by acetaminophen could be enhanced the surface area because the phenolic hydroxyl group of acetaminophen could improve the action of benzene ring;The hypercrosslinked resin modified by acetaminophen could be enhanced the adsorption capacity because of the hydrogen bond site of acetamino group and hydroxyl group.The hypercrosslinked resin modified with acetaminophen was synthesised with chloromethylated polystyrene and acetaminophen by Friedel-Crafts reaction.Dichloroethane was used as solvent and ferric chloride was used as catalyst.The objective of this work was to study the adsorption thermodynamics and adsorption kinetic of the kind of hypercrosslinked resin.The adsorption capacity for bisphenol A onto the hypercrosslinked resin modified by acetaminophen is 2.58 times as high as that of polysulphone micro-ball embedded with activated carbon.The adsorption isotherms of bisphenol A at different temperatures fitted well into Freundlich adsorption equation.The adsorption kinetic date of bisphenol A fitted to the first order rate equation.The intrapartical diffusion of bisphenol A was the main rate-controlling step.The results showed that the saturated adsorption quantity of vanillin was up to 119.1mg·mL~(-1)(wet resin) at 293K.The resin could be reused by 80%ethanol.The adsorption kinetic date of vanillin fitted to the second order rate equation.The intrapartical diffusion of vanillin was the main rate-controlling step.
引文
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