新型交联高分子载体材料的设计、制备及在催化反应中的应用
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摘要
有效的催化反应是实现绿色化学的切实有效的方法之一,聚合物负载催化剂具有易操作、易分离、易于实现工业化连续生产,一直以来是人们不断努力的方向之一。聚合物载体的结构与性能对催化剂的各项性能都有影响,因此设计、制备新型的聚合物载体,更充分地发挥催化剂的作用,是负载型催化剂研究的热点之一。本文主要工作内容如下：
制备了三种不同氯甲基化程度的交联聚苯乙烯微球,颗粒大小均匀,粒径在500-600nm左右,元素分析表明其中C1最高含量可达21.1%。以高度氯甲基化的聚苯乙烯微球为母体,对其进行咪唑功能化,然后以配位键固定CuI制备得PS-imCuI催化剂,用于催化咪唑类氮源和α,β-不饱和物的氮杂偶联加成反应(AMR),对于咪唑和丙烯腈的反应,和其他Cu化合物催化剂相比,在比较温和的条件下4h之内,即可获得92%收率,它还可以有效催化苯并咪唑、4-硝基咪唑和2-甲基-5-硝基咪唑为氮源的反应AMR反应,催化剂可通过简单的过滤进行回收,可重复利用5次以上。对PS-imCuI催化机理进行了探讨。
制备了三种不同负载量(离子液体)的PS-[SO3H-PMIM][HSO4]催化剂,将其用于催化甲苯等芳烃和68%硝酸的反应,均能获得较好的效果,且目标产物产率随离子液体负载量的增加而增加；负载催化剂对于取代基较小的芳烃有较好的区域选择性。研究推测有[NO3-][NO2+]和[N02+] PS-[SO3--PMIM][SO42-][N02+]两种硝酰离子对共存,后一种由于其体积较大使得催化剂催化效果有了一定的区域选择性,在不同的微环境下,两种硝化机理同时存在,相互竞争,形成了PS-[SO3H-PMIM][HSO4]特有的催化效果。该反应以68%的硝酸为硝化试剂,与传统的混酸硝化相比具有节能、安全、环保、高效的优点。将PS-[SO3H-PMIM][HSO4]用于催化乙酸和丁醇的反应,92℃下反应1.5h反应完毕,乙酸丁酯收率可达98%。
采用间接合成法,制备了两种凝胶负载离子液体催化剂,即PNIPAm-[SO3H-PMIM][HSO4]和PAAM-[SO3H-PMIM][HSO4],将之用于乙酸和丁醇的反应,催化效果一般。
设计并合成了五种可聚合光、或光/pH敏感单体,三种温度/光敏感水凝胶、两种温度/光/pH敏感水凝胶,并对其性能进行了深入的、全面的研究,筛选出三种综合性能较好的智能水凝胶,即GelNDEP、GelNAEP0.01和GelNAP0.01,这三种凝胶的紫外光响应速率分别为1.25×10-2S-1、6.2×10-3s-1和4.3×10-3s-1。紫外光照后,LCST最大分别增加1.6℃、2.6℃和1.4℃,平衡溶胀比(SR)最大分别增加3、2和1.5左右。紫外光调节范围宽,有良好的实际应用潜力。
在前面研究的基础上,合成了五种多孔互穿复合水凝胶GelNIPAm/PHEMA、 GelNIPAm/PAEMA、GelNDEP/PAEMA、GelNAEP/PAEMA和GelNAP/PAEMA,以这五种凝胶为载体,利用NIPAm的在水中的可逆低温相转变对糖化酶进行吸附,然后以戊二醛为交联剂,通过共价键结合法、交联法对糖化酶进行固定。后四种固定化糖化酶效果较好,固定糖化酶活性回收率为11.4%-15.3%,4℃贮存30天,酶活保留率在90%左右。对其催化淀粉水解的条件进行了考察,相对于自由糖化酶,固定化糖化酶的适宜pH向弱酸性偏移至约4.5,适宜温度从40℃向低温转移至30℃,在最佳使用范围内酶活力可以用紫外光进行一定量的调节。
Efficient catalytic reaction is a good method to realize green chemistry. Polymer supported catalyst is easy to use, separate and advantage to industrialize, so the preparation of good performance polymer catalyst is always the direction that people efforts to. The property and structure of polymer carriers can greatly influence the polymer supported catalyst. So the design and preparation of novel polymer supporters, which are good to catalysis, become a research focus for polymer supported catalysts. The major research works of this paper were below.
At first, three different chloromethylated polystyrene beads were synthesized, and the maximum content of Cl element was21.1%. Take the high chloromethylated degree polystyrene as precursor, it was first functionalized with imidazole, and then anchored CuI by coordinated bond between Cu and N in imidazole, so the PS-imCul complex catalyst was obtained. It could effectively catalyze the aza-Michael reaction of imidazoles and a, β-unsaturated compounds. For the reaction of imidazole and acrylonitrile,93%yield was acquired in75℃and4h, which was some better than the other reported Cu catalysts. PS-imCul was even efficient for the AMR of benzimidazole,4-nitroimidazole and2-methyl-5-nitroimidazole with a, β-unsaturated compounds, which were pharmacology important. It was easy to recover, and could be reused more than5times.
Three PS-[SO3H-PMIM][HSO4] catalysts with different content of ionic liquid,[SO3H-PMIM][HSO4], were prepared by grafting method. They were all efficient for nitration of simple arenes. The yield of aim-product increased with the increasing of IL. The supported IL catalysts presented good regioselectivity for the arenes with little substituent group. It was inferred that two kinds of nitryl cations carriers were existed, i.e.[NO3-][NO2+] and [NO2+]PS-[SO3--PMIM][SO42-][NO2+], and the latter was big enough to produce steric effect during the reaction. The two reaction mechanism were co-existent and competed in the special microenvironment of PS supported IL, and then the special catalytic result of PS-[SO3H-PMIM][HSO4] was formed. In the nitration,68%nitro acid was took as nitrifying reagent, which was low energy cost, safety, environment friendly compared with the traditional mixture acid nitro reaction. In addition, using PS-[SO3H-PMIM][HSO4] catalyze the esterification of acetic acid and butanol,98%yield of butyl acetate was obtained under92℃and1.5h.
Two kinds of hydrogel supported IL, i.e. PNIPAm-[SO3H-PMIM][HSO4] and PAAM-[SO3H-PMIM][HSO4], were prepared by indirect synthesis technique. The catalytic efficient in esterification of acetic acid and butanol were investigated, unfortunately, the catalytic effect were not to be the same as expected.
In the paper, three kinds of photosensitivity and two kinds of photo/pH-sensitivity monomers were designed and synthesized. Introducing the five polymerizable monomers into PNIPAm by copolymerization. Three thermo/light dual-responsive and two thermo/light/pH triply-responsive copolymeric hydrogels were prepared. The property of those hydrogels were researched carefully. Three kinds of hydrogels with good overall performances were screened, i.e. GelNAEP, GelNAEP0.011and GelNAP0.01. The UV-light responsive rate of the three gels were1.25x10-2s-1,6.2x10-3s-1and4.3×10-3s-1respectively, which were all quicker than the other relative reported. The LCST of these hydrogels increased1.6℃,2.6℃and1.4℃respectively, and the SR increased3,2and1.5respectively after UV-light radiation. In addition, GelNAEP0.01and GelNAP0.01were also pH sensitivity. The three hydrogels would have very good using potential.
Five porous IPN complex hydrogels were synthesized based on the above studies, and they were respectively GelNIPAm/PHEMA, GelNIPAm/PAEMA, GelNDEP/PAEMA, GelNAEP/PAEMA and GelNAP/PAEMA. Took the five gels as carriers, the glucoamylase was absorbed by them using the property of phase transformation of PNIPAm in water. The absorbed glucoamylase was then immobilized by covalent bond with gels or cross linking self by glutaraldehyde. The enzyme activity recovery of those immobilized glucoamylases were11.4%-15.3%, which were higher than the other relative reports. The immobilized enzyme activity obtained about90%after keeping in4℃for30days. The hydrolysis of soluble starch catalyzed by those immobilized glucoamylases were researched. It was found that the optimum temperature of immobilized glucoamylase shifted to30℃form40℃for free glucoamylase, and the suitable pH shifted to pH=4.5from neutral. In addition, the enzyme activity could be adjust by UV-light.
制备了三种不同氯甲基化程度的交联聚苯乙烯微球,颗粒大小均匀,粒径在500-600nm左右,元素分析表明其中C1最高含量可达21.1%。以高度氯甲基化的聚苯乙烯微球为母体,对其进行咪唑功能化,然后以配位键固定CuI制备得PS-imCuI催化剂,用于催化咪唑类氮源和α,β-不饱和物的氮杂偶联加成反应(AMR),对于咪唑和丙烯腈的反应,和其他Cu化合物催化剂相比,在比较温和的条件下4h之内,即可获得92%收率,它还可以有效催化苯并咪唑、4-硝基咪唑和2-甲基-5-硝基咪唑为氮源的反应AMR反应,催化剂可通过简单的过滤进行回收,可重复利用5次以上。对PS-imCuI催化机理进行了探讨。
制备了三种不同负载量(离子液体)的PS-[SO3H-PMIM][HSO4]催化剂,将其用于催化甲苯等芳烃和68%硝酸的反应,均能获得较好的效果,且目标产物产率随离子液体负载量的增加而增加；负载催化剂对于取代基较小的芳烃有较好的区域选择性。研究推测有[NO3-][NO2+]和[N02+] PS-[SO3--PMIM][SO42-][N02+]两种硝酰离子对共存,后一种由于其体积较大使得催化剂催化效果有了一定的区域选择性,在不同的微环境下,两种硝化机理同时存在,相互竞争,形成了PS-[SO3H-PMIM][HSO4]特有的催化效果。该反应以68%的硝酸为硝化试剂,与传统的混酸硝化相比具有节能、安全、环保、高效的优点。将PS-[SO3H-PMIM][HSO4]用于催化乙酸和丁醇的反应,92℃下反应1.5h反应完毕,乙酸丁酯收率可达98%。
采用间接合成法,制备了两种凝胶负载离子液体催化剂,即PNIPAm-[SO3H-PMIM][HSO4]和PAAM-[SO3H-PMIM][HSO4],将之用于乙酸和丁醇的反应,催化效果一般。
设计并合成了五种可聚合光、或光/pH敏感单体,三种温度/光敏感水凝胶、两种温度/光/pH敏感水凝胶,并对其性能进行了深入的、全面的研究,筛选出三种综合性能较好的智能水凝胶,即GelNDEP、GelNAEP0.01和GelNAP0.01,这三种凝胶的紫外光响应速率分别为1.25×10-2S-1、6.2×10-3s-1和4.3×10-3s-1。紫外光照后,LCST最大分别增加1.6℃、2.6℃和1.4℃,平衡溶胀比(SR)最大分别增加3、2和1.5左右。紫外光调节范围宽,有良好的实际应用潜力。
在前面研究的基础上,合成了五种多孔互穿复合水凝胶GelNIPAm/PHEMA、 GelNIPAm/PAEMA、GelNDEP/PAEMA、GelNAEP/PAEMA和GelNAP/PAEMA,以这五种凝胶为载体,利用NIPAm的在水中的可逆低温相转变对糖化酶进行吸附,然后以戊二醛为交联剂,通过共价键结合法、交联法对糖化酶进行固定。后四种固定化糖化酶效果较好,固定糖化酶活性回收率为11.4%-15.3%,4℃贮存30天,酶活保留率在90%左右。对其催化淀粉水解的条件进行了考察,相对于自由糖化酶,固定化糖化酶的适宜pH向弱酸性偏移至约4.5,适宜温度从40℃向低温转移至30℃,在最佳使用范围内酶活力可以用紫外光进行一定量的调节。
Efficient catalytic reaction is a good method to realize green chemistry. Polymer supported catalyst is easy to use, separate and advantage to industrialize, so the preparation of good performance polymer catalyst is always the direction that people efforts to. The property and structure of polymer carriers can greatly influence the polymer supported catalyst. So the design and preparation of novel polymer supporters, which are good to catalysis, become a research focus for polymer supported catalysts. The major research works of this paper were below.
At first, three different chloromethylated polystyrene beads were synthesized, and the maximum content of Cl element was21.1%. Take the high chloromethylated degree polystyrene as precursor, it was first functionalized with imidazole, and then anchored CuI by coordinated bond between Cu and N in imidazole, so the PS-imCul complex catalyst was obtained. It could effectively catalyze the aza-Michael reaction of imidazoles and a, β-unsaturated compounds. For the reaction of imidazole and acrylonitrile,93%yield was acquired in75℃and4h, which was some better than the other reported Cu catalysts. PS-imCul was even efficient for the AMR of benzimidazole,4-nitroimidazole and2-methyl-5-nitroimidazole with a, β-unsaturated compounds, which were pharmacology important. It was easy to recover, and could be reused more than5times.
Three PS-[SO3H-PMIM][HSO4] catalysts with different content of ionic liquid,[SO3H-PMIM][HSO4], were prepared by grafting method. They were all efficient for nitration of simple arenes. The yield of aim-product increased with the increasing of IL. The supported IL catalysts presented good regioselectivity for the arenes with little substituent group. It was inferred that two kinds of nitryl cations carriers were existed, i.e.[NO3-][NO2+] and [NO2+]PS-[SO3--PMIM][SO42-][NO2+], and the latter was big enough to produce steric effect during the reaction. The two reaction mechanism were co-existent and competed in the special microenvironment of PS supported IL, and then the special catalytic result of PS-[SO3H-PMIM][HSO4] was formed. In the nitration,68%nitro acid was took as nitrifying reagent, which was low energy cost, safety, environment friendly compared with the traditional mixture acid nitro reaction. In addition, using PS-[SO3H-PMIM][HSO4] catalyze the esterification of acetic acid and butanol,98%yield of butyl acetate was obtained under92℃and1.5h.
Two kinds of hydrogel supported IL, i.e. PNIPAm-[SO3H-PMIM][HSO4] and PAAM-[SO3H-PMIM][HSO4], were prepared by indirect synthesis technique. The catalytic efficient in esterification of acetic acid and butanol were investigated, unfortunately, the catalytic effect were not to be the same as expected.
In the paper, three kinds of photosensitivity and two kinds of photo/pH-sensitivity monomers were designed and synthesized. Introducing the five polymerizable monomers into PNIPAm by copolymerization. Three thermo/light dual-responsive and two thermo/light/pH triply-responsive copolymeric hydrogels were prepared. The property of those hydrogels were researched carefully. Three kinds of hydrogels with good overall performances were screened, i.e. GelNAEP, GelNAEP0.011and GelNAP0.01. The UV-light responsive rate of the three gels were1.25x10-2s-1,6.2x10-3s-1and4.3×10-3s-1respectively, which were all quicker than the other relative reported. The LCST of these hydrogels increased1.6℃,2.6℃and1.4℃respectively, and the SR increased3,2and1.5respectively after UV-light radiation. In addition, GelNAEP0.01and GelNAP0.01were also pH sensitivity. The three hydrogels would have very good using potential.
Five porous IPN complex hydrogels were synthesized based on the above studies, and they were respectively GelNIPAm/PHEMA, GelNIPAm/PAEMA, GelNDEP/PAEMA, GelNAEP/PAEMA and GelNAP/PAEMA. Took the five gels as carriers, the glucoamylase was absorbed by them using the property of phase transformation of PNIPAm in water. The absorbed glucoamylase was then immobilized by covalent bond with gels or cross linking self by glutaraldehyde. The enzyme activity recovery of those immobilized glucoamylases were11.4%-15.3%, which were higher than the other relative reports. The immobilized enzyme activity obtained about90%after keeping in4℃for30days. The hydrolysis of soluble starch catalyzed by those immobilized glucoamylases were researched. It was found that the optimum temperature of immobilized glucoamylase shifted to30℃form40℃for free glucoamylase, and the suitable pH shifted to pH=4.5from neutral. In addition, the enzyme activity could be adjust by UV-light.
引文
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