烷基化缩聚型超高交联树脂的制备、修饰及吸附性能研究
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摘要
超高交联吸附树脂作为继凝胶树脂和大孔吸附树脂后的第三代聚合物吸附剂,凭借其优良的微孔结构、较高的比表面积以及良好的吸附性能,在石油化工环境保护、生物医药以及天然产物分离纯化等领域发挥着重要的作用。由于传统的超高交联吸附树脂存在骨架结构单一、制备成本较高的缺点,在某些程度上限制了其应用领域的拓展。不断开发高性能、低成本的超高交联吸附树脂以满足工业化发展对吸附分离材料的新要求,已成为研究人员共同努力的目标和方向。本研究利用Friedel-Crafts烷基化缩聚反应制备了一系列非苯乙烯型超高交联吸附树脂,并对其性能及应用进行了系统的研究。主要内容包括以下四个部分：
(1)通过1,4-二氯甲基苯(XDC)、4,4’-二氯甲基联苯(CMB)自聚或与苯(BE)、联苯(DP)共聚,制备了7种具有不同骨架结构的超高交联吸附树脂。比较了不同单体及其比例对产品比表面积和孔径分布的影响,XDC-XDC. CMB-CMB和XDC-CMB树脂的比表面积分别可达1045.23m2/g、1253、23m2/g、1502.75m2/g。增加单体中二氯甲基化合物的比例或使用氯甲基含量高的单体,可使反应产物的交联度提高,比表面积和孔体积增大。分别用BET法和染料吸附法测定了树脂的干态比表面积和溶胀态下的有效比表面积。结果表明,随着干态比表面积的增加,溶胀态下有效比表面积也增加,在树脂比表面积较接近的情况下,树脂的孔体积与孔径分布会对有效比表面积产生一定的影响。
(2)研究了不同骨架吸附树脂对苯酚、萘酚和亚甲蓝的吸附性能。通过测定树脂对不同分子尺寸化合物的吸附容量和吸附速率,考察了树脂孔结构与吸附质分子尺寸对吸附性能的影响。结果表明,双氯甲基化合物自聚或共聚得到的XDC-CMB、CMB-CMB和XDC-XDC对苯酚、萘酚、亚甲蓝的吸附量都比较大,对有机小分子化合物的吸附,吸附量主要受树脂比表面积的影响,随着树脂比表面积的增大,吸附量也增大。8种吸附树脂对苯酚、萘酚、亚甲蓝的吸附等温线都能很好的用Langmuir方程和Freundlich方程拟合,Freundlich模型中,当n>1时,表明吸附过程易于进行,均为优惠吸附。苯酚、萘酚和亚甲蓝在树脂上的吸附动力学行为可用一级不可逆吸附反应膜扩散方程进行描述；在298K时,CMB-CMB树脂对苯酚、萘酚和亚甲蓝的吸附速率常数K分别为0.035min-1,0.082min-1,0.012min-1,对3神吸附质均有较快的吸附速率和较大的吸附量,适用于对水中酚类和小分子染料污染物的快速吸附。
(3)对BE-XDC树脂进行极性修饰,得到了强酸(-SO3H)型超高交联离子交换树脂。利用红外光谱、元素分析及化学滴定等手段对树脂的物理化学结构和性能进行了分析和表征,并对树脂的合成工艺条件进行优化。在反应温度65℃,反应时间4h,物料物质的量比为1：2(树脂：氯磺酸)时,可得到交换容量为3.89mmol/g的强酸型超高交联离子交换树脂(SBE-XDC)。SBE-XDC树脂对水溶液中Cu2+、Ni2+的吸附量分别可达1.82mmol/g和1.85mmol/g,均略高于理论吸附量1.64mmol/g,说明树脂的微孔结构对Cu2+、Ni2+也有较好的吸附。SBE-XDC树脂对水溶液中Cu2+、Ni2+的吸附过程均符合Langmuir模型,该吸附过程主要是单分子层的化学吸附,并且是一个自发吸热的不可逆过程(△H>0,△G<0,△S>0)。
(4)采用硝基苯-二甲基硅油双油相悬浮聚合体系制备得到球形非苯乙烯型超高交联吸附树脂(SCMB)。采用红外光谱仪、比表面及孔径测定仪以及显微成像系统对ACMB、SCMB和PSCMB树脂的表面基团、微观形貌以及孔性能进行了表征。采用双油相比例01/02=1：5(体积比),苯甲酸正丁酯用量1%(体积比),50℃、60℃、70℃各反应1h后,停止搅拌,升温至80℃保温4h,调节搅拌速度能够得到不同粒径分布的产品。产品的比表面积最高可达1190.02m2/g,孔体积为0.714cm3/g。
Hypercrosslinked resin as the third generation of polymeric adsorbent after the gel resin and macroporous adsorption resin, for the characteristics of excellent micropore structure, higher BET surface areas, and good adsorption properties, has played an important role in petrochemical, environmental protection, biological medicine and separation of plants active ingredient. However, due to the single framework (St-DVB) and high preparation cost of the traditional hypecrosslinked resin, the application was limited to some extent. It has become a common goal for scientific workers of different countries to continuous develop high-performance and low cost hypercrosslinked resin, in order to satisfy the new requirement from the industry. In this paper, non-traditional hypercrosslinked resin with high specific area was prepared by direct Friedel-Crafts alkylation polycondensation. The main content contains four parts.
Part One:A series of hypercrosslinked resin with different framework was prepared by self-condensation of1,4-bis(chloromethyl)-benzene (XDC) and4,4'-bis-(chloromethyl)-l,1'-biphenyl (CMB) or co-polycondensation with benzene (BE) and biphenyl (DP). The effects of different monomer and the ratio on the surface areas and pore size distribution of the products were compared. The surface areas of XDC-XDC. CMB-CMB and XDC-CMB resin were1045.23m2/g,1253.23m2/g and1502.75m2/g, respectively. The pore radiuses were centralized below20nm. The degree of the crosslink, surface area and pore volume were increased with the increasing the ratio of dichloromethyl compound or using monomer with high chloromethyl content. The surface areas under dry state and swell state were determined by BET method and dye adsorption method, respectively. The results indicated that, the surface area under swell state is to some extent in proportional to the surface area under dry state, as well as affected by the pore structure and the pore size distribution.
Part Two:The adsorption performance of resins with different framework on phenol, naphthol and methylene blue were investigated. The effect of pore structure of the resins and molecular size of the adsorbors on the adsorption performance were reviewed, the adsorption capacity and adsorption rate of compounds with varies size on different resins were determined. The results show that resins which obtained by self-condensation or co-polymerization of dichloromethyl compound have higher surface area, and the adsorption capacities on phenol, naphthol and methylene blue were also higher. To the adsorption of small size compound, the adsorption capacity was mainly affected by the surface area of the resin; it was increased with the surface area of the resin. The thermodynamic adsorption data showed that Langmuir and Freundlich isotherms were found to fit well the adsorption data of three adsorbor onto the eight resins. The exponent factor n>1in Freundlich isotherms equations, the adsorption is thus favorable. Kinetic study showed that the adsorption performance of these resins for phenol, naphthol and methylene blue can be described by a first-order irreversible adsorption rate equation. The rate constants of adsorptions of phenol, naphthol and methylene blue at298K are0.034min-1,0.082min-1,0.011min-1respectively. CMB-CMB resin possesses a quick adsorption rate and high adsorption capacity, and it has good potential for treating the contamination in the water with high removal efficiency.
Part Three:Strong acidic (-SO3H) ion exchange hypercrosslinked resins were prepared via introduce sulfonic group on BE-XDC resin. The physic-chemical structure and properties were characterized by FT-IR, elementary analysis and chemical titration respectively. Various factors affecting the sulfonation reaction such as reactive temperature, reactive time and the mole ratio of the sulfonation reagent were optimized. The exchange capacity of the sulfonated resin is up to3.89mmol/g. The adsorption capacities of SBE-XDC resin for Cu2+、Ni2+in aqueous solution were114.97mg/g (1.82mmol/g) and109.09mg/g (1.85mmol/g) respectively, both slightly higher than the theoretic adsorption capacity, it indicate that the micropore of the resin can absorb Cu2+、Ni2+to same extent. The thermodynamic adsorption data showed that Langmuir isotherms were found to fit well with the adsorption data of Cu2+、Ni2+onto the SBE-XDC resin. The adsorption progress was mainly mono layer chemical adsorption, adsorption enthalpy ΔH>0, adsorption free energy ΔG<0and adsorption entropy ΔS>0, it indicate that the adsorption progress was a spontaneous, endothermal and irreversible progress.
Part Four:The suspension polymerization with two organic phases was successful adopted to prepare spherical hypercrosslinked resin by self-polycondensation of4,4'-bis-(chloromethyl)-1,1'-biphenyl (CMB). The chemical structure, morphology and pore characteristics of the novel spherical resin were characterized with Fourier transform infrared spectroscopy (FTIR), micrograph and Brunauer-Emmett-Teller (BET). Keep the volume ratio of the two organic phases (nitrobenzene/dimethyl silicon oil)1:5(V/V), dispersant amount1%(V/V),50℃(1h),60℃(1h),70℃(1h) and80℃(4h), adjust the stirring speed, appropriate size products can be obtained. The maximum surface area of the resin bead was1190.02m2/g, and the pore volume was0.714cm3/g.
(1)通过1,4-二氯甲基苯(XDC)、4,4’-二氯甲基联苯(CMB)自聚或与苯(BE)、联苯(DP)共聚,制备了7种具有不同骨架结构的超高交联吸附树脂。比较了不同单体及其比例对产品比表面积和孔径分布的影响,XDC-XDC. CMB-CMB和XDC-CMB树脂的比表面积分别可达1045.23m2/g、1253、23m2/g、1502.75m2/g。增加单体中二氯甲基化合物的比例或使用氯甲基含量高的单体,可使反应产物的交联度提高,比表面积和孔体积增大。分别用BET法和染料吸附法测定了树脂的干态比表面积和溶胀态下的有效比表面积。结果表明,随着干态比表面积的增加,溶胀态下有效比表面积也增加,在树脂比表面积较接近的情况下,树脂的孔体积与孔径分布会对有效比表面积产生一定的影响。
(2)研究了不同骨架吸附树脂对苯酚、萘酚和亚甲蓝的吸附性能。通过测定树脂对不同分子尺寸化合物的吸附容量和吸附速率,考察了树脂孔结构与吸附质分子尺寸对吸附性能的影响。结果表明,双氯甲基化合物自聚或共聚得到的XDC-CMB、CMB-CMB和XDC-XDC对苯酚、萘酚、亚甲蓝的吸附量都比较大,对有机小分子化合物的吸附,吸附量主要受树脂比表面积的影响,随着树脂比表面积的增大,吸附量也增大。8种吸附树脂对苯酚、萘酚、亚甲蓝的吸附等温线都能很好的用Langmuir方程和Freundlich方程拟合,Freundlich模型中,当n>1时,表明吸附过程易于进行,均为优惠吸附。苯酚、萘酚和亚甲蓝在树脂上的吸附动力学行为可用一级不可逆吸附反应膜扩散方程进行描述；在298K时,CMB-CMB树脂对苯酚、萘酚和亚甲蓝的吸附速率常数K分别为0.035min-1,0.082min-1,0.012min-1,对3神吸附质均有较快的吸附速率和较大的吸附量,适用于对水中酚类和小分子染料污染物的快速吸附。
(3)对BE-XDC树脂进行极性修饰,得到了强酸(-SO3H)型超高交联离子交换树脂。利用红外光谱、元素分析及化学滴定等手段对树脂的物理化学结构和性能进行了分析和表征,并对树脂的合成工艺条件进行优化。在反应温度65℃,反应时间4h,物料物质的量比为1：2(树脂：氯磺酸)时,可得到交换容量为3.89mmol/g的强酸型超高交联离子交换树脂(SBE-XDC)。SBE-XDC树脂对水溶液中Cu2+、Ni2+的吸附量分别可达1.82mmol/g和1.85mmol/g,均略高于理论吸附量1.64mmol/g,说明树脂的微孔结构对Cu2+、Ni2+也有较好的吸附。SBE-XDC树脂对水溶液中Cu2+、Ni2+的吸附过程均符合Langmuir模型,该吸附过程主要是单分子层的化学吸附,并且是一个自发吸热的不可逆过程(△H>0,△G<0,△S>0)。
(4)采用硝基苯-二甲基硅油双油相悬浮聚合体系制备得到球形非苯乙烯型超高交联吸附树脂(SCMB)。采用红外光谱仪、比表面及孔径测定仪以及显微成像系统对ACMB、SCMB和PSCMB树脂的表面基团、微观形貌以及孔性能进行了表征。采用双油相比例01/02=1：5(体积比),苯甲酸正丁酯用量1%(体积比),50℃、60℃、70℃各反应1h后,停止搅拌,升温至80℃保温4h,调节搅拌速度能够得到不同粒径分布的产品。产品的比表面积最高可达1190.02m2/g,孔体积为0.714cm3/g。
Hypercrosslinked resin as the third generation of polymeric adsorbent after the gel resin and macroporous adsorption resin, for the characteristics of excellent micropore structure, higher BET surface areas, and good adsorption properties, has played an important role in petrochemical, environmental protection, biological medicine and separation of plants active ingredient. However, due to the single framework (St-DVB) and high preparation cost of the traditional hypecrosslinked resin, the application was limited to some extent. It has become a common goal for scientific workers of different countries to continuous develop high-performance and low cost hypercrosslinked resin, in order to satisfy the new requirement from the industry. In this paper, non-traditional hypercrosslinked resin with high specific area was prepared by direct Friedel-Crafts alkylation polycondensation. The main content contains four parts.
Part One:A series of hypercrosslinked resin with different framework was prepared by self-condensation of1,4-bis(chloromethyl)-benzene (XDC) and4,4'-bis-(chloromethyl)-l,1'-biphenyl (CMB) or co-polycondensation with benzene (BE) and biphenyl (DP). The effects of different monomer and the ratio on the surface areas and pore size distribution of the products were compared. The surface areas of XDC-XDC. CMB-CMB and XDC-CMB resin were1045.23m2/g,1253.23m2/g and1502.75m2/g, respectively. The pore radiuses were centralized below20nm. The degree of the crosslink, surface area and pore volume were increased with the increasing the ratio of dichloromethyl compound or using monomer with high chloromethyl content. The surface areas under dry state and swell state were determined by BET method and dye adsorption method, respectively. The results indicated that, the surface area under swell state is to some extent in proportional to the surface area under dry state, as well as affected by the pore structure and the pore size distribution.
Part Two:The adsorption performance of resins with different framework on phenol, naphthol and methylene blue were investigated. The effect of pore structure of the resins and molecular size of the adsorbors on the adsorption performance were reviewed, the adsorption capacity and adsorption rate of compounds with varies size on different resins were determined. The results show that resins which obtained by self-condensation or co-polymerization of dichloromethyl compound have higher surface area, and the adsorption capacities on phenol, naphthol and methylene blue were also higher. To the adsorption of small size compound, the adsorption capacity was mainly affected by the surface area of the resin; it was increased with the surface area of the resin. The thermodynamic adsorption data showed that Langmuir and Freundlich isotherms were found to fit well the adsorption data of three adsorbor onto the eight resins. The exponent factor n>1in Freundlich isotherms equations, the adsorption is thus favorable. Kinetic study showed that the adsorption performance of these resins for phenol, naphthol and methylene blue can be described by a first-order irreversible adsorption rate equation. The rate constants of adsorptions of phenol, naphthol and methylene blue at298K are0.034min-1,0.082min-1,0.011min-1respectively. CMB-CMB resin possesses a quick adsorption rate and high adsorption capacity, and it has good potential for treating the contamination in the water with high removal efficiency.
Part Three:Strong acidic (-SO3H) ion exchange hypercrosslinked resins were prepared via introduce sulfonic group on BE-XDC resin. The physic-chemical structure and properties were characterized by FT-IR, elementary analysis and chemical titration respectively. Various factors affecting the sulfonation reaction such as reactive temperature, reactive time and the mole ratio of the sulfonation reagent were optimized. The exchange capacity of the sulfonated resin is up to3.89mmol/g. The adsorption capacities of SBE-XDC resin for Cu2+、Ni2+in aqueous solution were114.97mg/g (1.82mmol/g) and109.09mg/g (1.85mmol/g) respectively, both slightly higher than the theoretic adsorption capacity, it indicate that the micropore of the resin can absorb Cu2+、Ni2+to same extent. The thermodynamic adsorption data showed that Langmuir isotherms were found to fit well with the adsorption data of Cu2+、Ni2+onto the SBE-XDC resin. The adsorption progress was mainly mono layer chemical adsorption, adsorption enthalpy ΔH>0, adsorption free energy ΔG<0and adsorption entropy ΔS>0, it indicate that the adsorption progress was a spontaneous, endothermal and irreversible progress.
Part Four:The suspension polymerization with two organic phases was successful adopted to prepare spherical hypercrosslinked resin by self-polycondensation of4,4'-bis-(chloromethyl)-1,1'-biphenyl (CMB). The chemical structure, morphology and pore characteristics of the novel spherical resin were characterized with Fourier transform infrared spectroscopy (FTIR), micrograph and Brunauer-Emmett-Teller (BET). Keep the volume ratio of the two organic phases (nitrobenzene/dimethyl silicon oil)1:5(V/V), dispersant amount1%(V/V),50℃(1h),60℃(1h),70℃(1h) and80℃(4h), adjust the stirring speed, appropriate size products can be obtained. The maximum surface area of the resin bead was1190.02m2/g, and the pore volume was0.714cm3/g.
引文
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