天然高分子金属络合物在不对称水合及Heck反应催化性能的研究
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摘要
本论文对多种天然高分子金属络合物(如蚕丝、田菁胶、纤维素、羊毛、腐植酸、金鸡纳碱、壳聚糖等载体)在催化应用领域中的研究进展做了较详细的文献总结,并重点介绍了壳聚糖载体催化不对称反应与Heck反应的研究进展。在此基础上制备了多种壳聚糖希夫碱负载单金属与双金属的配合物,并考察了它们在不对称水合与Heck反应中的催化性能。
首先,以含有大量羟基和氨基的壳聚糖为原料,用水杨醛对其进行适当的化学改性得到壳聚糖希夫碱配体,再通过简单的反应得到一系列壳聚糖希夫碱负载单金属与双金属的配合物。利用傅立叶红外、X-射线粉末衍射和X-射线光电子能谱对壳聚糖希夫碱负载单金属钯配合物和壳聚糖希夫碱负载双金属钴钯配合物进行了表征。结果表明:壳聚糖席夫碱中的氮、氧原子均与金属钴、钯原子间形成了配位键。
其次,研究了壳聚糖希夫碱负载单金属与双金属的配合物对不饱和酸的不对称水合反应的催化性能。这些催化剂均能催化2-甲基丙烯酸的不对称水合。比较发现,壳聚糖希夫碱负载双金属配合物具有比壳聚糖希夫碱负载单金属配合物更好的催化性能,其中壳聚糖希夫碱负载双金属钴钯配合物的催化性能最好。并对催化剂中不同的钯/钴摩尔比、钯和钴的总负载量、反应温度和反应时间进行了考察,得出了最佳的反应条件为:钯/钴摩尔比为1/1,钯和钻的总负载量为0.18mmol/g,阻聚剂对苯二酚0.01g,90℃下反应24h,在上述反应条件下(S)-(+)-α-甲基-β-羟基丙酸产率和光学收率分别为90.6%和91.8%。并且该催化剂重复使用5次,催化活性仍然较高。
最后,考察了壳聚糖希夫碱负载双金属配合物对碘代苯与丙烯酰胺反应的催化性能。比较发现,壳聚糖希夫碱负载双金属钴钯配合物的催化性能最好,该催化剂在钯/钻摩尔比为1/3,催化剂用量为0.125g,碘代苯/丙烯酰胺的摩尔比为1/1.8,三乙胺为缚酸剂、用量为18mmol,回流温度110℃下反应1h,肉桂酰胺的产率就可达93.7%,而且还具有很好的重复使用性,可重复使用10次。此外,还用于了其它底物(卤代苯及碘苯衍生物)的催化,结果表明该催化剂对于吸电子取代基的碘苯具有较高的催化活性。
In this thesis, the recent progress about some natural polymer-metal complexes (carriers such as: silk, sesbania gum, fibrin, wool, humic acid, cinchona, chitosan and so on) in the catalytic application field was reviewed in detail. And the recent progress about chitosan carrier in the asymmetric reaction and Heck reaction was highlighted. On the basis, the chitosan-schiff base supported monometallic and bimetallic complexes were prepared and their catalytic performances in the asymmetric hydration and Heck reaction were studied.
Firstly, containing a large number of hydroxy and amino of chitosan as raw material, chitosan was appropriate chemical modified with salicylaldehyde to obtain chitosan-schiff base ligand. And then we got a series of chitosan-schiff base supported monometallic and bimetallic complexes by the simple reaction. Chitosan-schiff base supported Pd monometallic and chitosan-schiff base supported Pd/Co bimetallic complexes were characterized with FT-IR, XRD and XPS. According to the results of analysis, the coordination bonds were formed by the connection of nitrogen and oxygen atoms of chitosan schiff base with the metal cobalt, palladium atoms.
Secondly, catalytic performance of chitosan-schiff base supported monometallic and supported bimetallic complexes for the asymmetric hydration of unsaturated acid was studied. These complexes were catalyzed for the asymmetric hydration of 2-methacrylic acid. The detailed studies showed that the catalytic performance of chitosan-schiff base supported bimetallic complexes is much more efficient than chitosan-schiff base supported monometallic complexes. It was found that the chitosan-schiff base supported Pd/Co bimetallic complex had the highest catalytic activity. And the influences of the molar ratio of Pd/Co, Pd+Co content, reaction temperature and reaction time on the reaction were investigated. The optimum conditions for the reaction were established as followed: n(Pd)/n(Co)=1/1, n(Pd+Co)=0.18mmol/g, hydroquinone 0.01g and 90℃for 24h. Under the above condition, the yield and optical yield of (S)-(+)-α-methyl-β-hydroxypr-opanoic acid were 90.6% and 91.8%, respectively. The catalyst was recycled for five times still with the good catalytic activity.
Finally, catalytic performance of chitosan-schiff base supported bimetallic complexes for iodobenzene (PhI) with acrylamide (AA) was investigated. The chitosan-schiff base supported Pd/Co bimetallic complex was efficient catalyst for the reaction at the molar ratio of Pd/Co :1/3, the amount of catalyst 0.125g, n (PhI): n (AA) = 1:1.8, Et_3N as base, the amount of base 18mmol and 110℃for 1h, the yield of cinnamamide was up to 93.7%. The catalyst had good reusability in the Heck reaction of PhI with AA, and it could be reused for ten times. The other substrates (phenyl halide and iodobenzene derivatives) were also investigated. The results showed that the catalyst had high activity for the iodobenzene coupling electron-withdrawing groups.
首先,以含有大量羟基和氨基的壳聚糖为原料,用水杨醛对其进行适当的化学改性得到壳聚糖希夫碱配体,再通过简单的反应得到一系列壳聚糖希夫碱负载单金属与双金属的配合物。利用傅立叶红外、X-射线粉末衍射和X-射线光电子能谱对壳聚糖希夫碱负载单金属钯配合物和壳聚糖希夫碱负载双金属钴钯配合物进行了表征。结果表明:壳聚糖席夫碱中的氮、氧原子均与金属钴、钯原子间形成了配位键。
其次,研究了壳聚糖希夫碱负载单金属与双金属的配合物对不饱和酸的不对称水合反应的催化性能。这些催化剂均能催化2-甲基丙烯酸的不对称水合。比较发现,壳聚糖希夫碱负载双金属配合物具有比壳聚糖希夫碱负载单金属配合物更好的催化性能,其中壳聚糖希夫碱负载双金属钴钯配合物的催化性能最好。并对催化剂中不同的钯/钴摩尔比、钯和钴的总负载量、反应温度和反应时间进行了考察,得出了最佳的反应条件为:钯/钴摩尔比为1/1,钯和钻的总负载量为0.18mmol/g,阻聚剂对苯二酚0.01g,90℃下反应24h,在上述反应条件下(S)-(+)-α-甲基-β-羟基丙酸产率和光学收率分别为90.6%和91.8%。并且该催化剂重复使用5次,催化活性仍然较高。
最后,考察了壳聚糖希夫碱负载双金属配合物对碘代苯与丙烯酰胺反应的催化性能。比较发现,壳聚糖希夫碱负载双金属钴钯配合物的催化性能最好,该催化剂在钯/钻摩尔比为1/3,催化剂用量为0.125g,碘代苯/丙烯酰胺的摩尔比为1/1.8,三乙胺为缚酸剂、用量为18mmol,回流温度110℃下反应1h,肉桂酰胺的产率就可达93.7%,而且还具有很好的重复使用性,可重复使用10次。此外,还用于了其它底物(卤代苯及碘苯衍生物)的催化,结果表明该催化剂对于吸电子取代基的碘苯具有较高的催化活性。
In this thesis, the recent progress about some natural polymer-metal complexes (carriers such as: silk, sesbania gum, fibrin, wool, humic acid, cinchona, chitosan and so on) in the catalytic application field was reviewed in detail. And the recent progress about chitosan carrier in the asymmetric reaction and Heck reaction was highlighted. On the basis, the chitosan-schiff base supported monometallic and bimetallic complexes were prepared and their catalytic performances in the asymmetric hydration and Heck reaction were studied.
Firstly, containing a large number of hydroxy and amino of chitosan as raw material, chitosan was appropriate chemical modified with salicylaldehyde to obtain chitosan-schiff base ligand. And then we got a series of chitosan-schiff base supported monometallic and bimetallic complexes by the simple reaction. Chitosan-schiff base supported Pd monometallic and chitosan-schiff base supported Pd/Co bimetallic complexes were characterized with FT-IR, XRD and XPS. According to the results of analysis, the coordination bonds were formed by the connection of nitrogen and oxygen atoms of chitosan schiff base with the metal cobalt, palladium atoms.
Secondly, catalytic performance of chitosan-schiff base supported monometallic and supported bimetallic complexes for the asymmetric hydration of unsaturated acid was studied. These complexes were catalyzed for the asymmetric hydration of 2-methacrylic acid. The detailed studies showed that the catalytic performance of chitosan-schiff base supported bimetallic complexes is much more efficient than chitosan-schiff base supported monometallic complexes. It was found that the chitosan-schiff base supported Pd/Co bimetallic complex had the highest catalytic activity. And the influences of the molar ratio of Pd/Co, Pd+Co content, reaction temperature and reaction time on the reaction were investigated. The optimum conditions for the reaction were established as followed: n(Pd)/n(Co)=1/1, n(Pd+Co)=0.18mmol/g, hydroquinone 0.01g and 90℃for 24h. Under the above condition, the yield and optical yield of (S)-(+)-α-methyl-β-hydroxypr-opanoic acid were 90.6% and 91.8%, respectively. The catalyst was recycled for five times still with the good catalytic activity.
Finally, catalytic performance of chitosan-schiff base supported bimetallic complexes for iodobenzene (PhI) with acrylamide (AA) was investigated. The chitosan-schiff base supported Pd/Co bimetallic complex was efficient catalyst for the reaction at the molar ratio of Pd/Co :1/3, the amount of catalyst 0.125g, n (PhI): n (AA) = 1:1.8, Et_3N as base, the amount of base 18mmol and 110℃for 1h, the yield of cinnamamide was up to 93.7%. The catalyst had good reusability in the Heck reaction of PhI with AA, and it could be reused for ten times. The other substrates (phenyl halide and iodobenzene derivatives) were also investigated. The results showed that the catalyst had high activity for the iodobenzene coupling electron-withdrawing groups.
引文
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