树枝状聚合物负载后过渡金属催化剂的制备及其在1-己烯氢甲酰化反应中的回收利用
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摘要
均相催化剂的催化活性虽然较高,但是催化剂与有机小分子反应物及产物的分离以及催化剂的回收再循环利用仍然是制约均相催化剂应用的一大因素。常规的分离方法如蒸馏、萃取等对某些特殊反应不能适用,比如,沸点较高的产物,以及在萃取过程中催化剂的失活再生等。非均相催化剂的回收循环利用较容易,但是由于催化剂与反应物接触受到接触面积的限制,使催化效率及催化活性受到限制。基于此,我们设计制备以树枝状聚合物为载体,通过离子交换将小分子催化剂负载到树枝状聚合物上形成均相催化体系的树枝状负载催化剂。并将此催化剂用于烯烃的甲酰化反应。具体内容如下：
以9,9-二甲基氧杂蒽为原料制备含有磷酸基团或磺酸基团的二苯基氧杂蒽膦配体,并对所合成的产物结构用NMR和IR表征,结果表明,含有磷酸基团的二苯基氧杂蒽膦配体较难合成,而含有磺酸基团的二苯基氧杂蒽膦配体成功合成。
以树枝状聚甘油为原料,经一锅法与1,2-二甲基咪唑、6-溴己酰氯反应制备端基含阳离子的树枝状聚合物。将合成的含磺酸钠的二苯基氧杂蒽膦配体、小分子铑络合物与树枝状聚合物经离子交换负载在聚合物上形成树枝状聚合物负载膦铑催化剂。并对二苯基氧杂蒽膦配体键合到聚合物上的条件进行了优化,结果表明,配体与聚合物摩尔数之比为1：2时,配体键合到聚合物上的效果最好。
将制备的树枝状聚合物负载的膦铑催化剂用于1-己烯的均相催化甲酰化反应,经超滤回收研究该催化剂的回收循环对催化活性及选择性的影响。结果表明,树枝状聚合物负载膦铑催化剂与小分子催化剂对1-己烯的甲酰化反应相比,树枝状负载催化剂的催化活性较高,但选择性较低。树枝状聚合物负载的膦铑催化剂经4次回收循环催化实验,其对1-己烯的催化活性降低很少,但是其催化选择性降低较多。
Although the catalytic activity of homogeneous catalysts is higher, but the catalyst and organic small molecules of reactant and product separation and catalyst recycling recycling is still a major factor restricting the application of homogeneous catalysts. Conventional separation methods such as distillation, extraction can not be applied to some special effects, for example, the product of a higher boiling point, and the deactivation of the catalyst in the extraction process of regeneration. Easier to recycle and reuse of the heterogeneous catalyst, but limited contact by the contact area due to the catalyst and reactants, the catalytic efficiency and catalytic activity is restricted. Based on this, we designed and fabricated to the dendrimer as a carrier, catalyst loading of small molecules to the dendrimers on the formation of homogeneous catalytic system, dendritic supported catalysts by ion exchange. And catalyst for the hydroformylation reaction of olefins. Details are as follows:
Containing phosphoric acid groups or sulfonic acid groups of the two phenyl xanthene phosphine ligand was prepared from9,9-dimethyl-xanthene, synthesis and structure of the product by NMR and IR characterization results show that, contain phosphate groups, two phenyl xanthene phosphine ligand is more difficult synthesis of diphenyl xanthene phosphine ligands containing sulfonic acid groups were successfully synthesized.
Dendritic polyglycerol as raw material, one-pot1,2-dimethyl imidazole,6-bromhexine chloride prepared by the reaction end groups containing cationic dendrimers. Synthesis containing sodium diphenyl xanthene phosphine ligands and rhodium complexes with dendrimers of small molecules by ion-exchange load in the formation of the dendrimer polymer load phosphine rhodium catalyst. And diphenyl the xanthene phosphine ligand bonded to the polymer on the conditions were optimized, the results show that the ligand and the number of polymer mole ratio of1:2ligand bonded to the polymer the best results.
Will prepared dendrimers load the phosphine rhodium catalysts for the reaction of1-hexene homogeneous catalytic hydroformylation, ultrafiltration recovery study of recovery and recycling of the catalyst on the catalytic activity and selectivity. The results showed that the dendrimer load phosphine rhodium catalyst with small molecule catalyst compared to the1-hexene hydroformylation reaction, the catalytic activity of dendritic load high, but low selectivity. Dendritic polymer supported phosphine rhodium catalyst after four times recycling loop catalytic experiments, the lower the catalytic activity of1-hexene little, but its catalytic selectivity greater reductions.
以9,9-二甲基氧杂蒽为原料制备含有磷酸基团或磺酸基团的二苯基氧杂蒽膦配体,并对所合成的产物结构用NMR和IR表征,结果表明,含有磷酸基团的二苯基氧杂蒽膦配体较难合成,而含有磺酸基团的二苯基氧杂蒽膦配体成功合成。
以树枝状聚甘油为原料,经一锅法与1,2-二甲基咪唑、6-溴己酰氯反应制备端基含阳离子的树枝状聚合物。将合成的含磺酸钠的二苯基氧杂蒽膦配体、小分子铑络合物与树枝状聚合物经离子交换负载在聚合物上形成树枝状聚合物负载膦铑催化剂。并对二苯基氧杂蒽膦配体键合到聚合物上的条件进行了优化,结果表明,配体与聚合物摩尔数之比为1：2时,配体键合到聚合物上的效果最好。
将制备的树枝状聚合物负载的膦铑催化剂用于1-己烯的均相催化甲酰化反应,经超滤回收研究该催化剂的回收循环对催化活性及选择性的影响。结果表明,树枝状聚合物负载膦铑催化剂与小分子催化剂对1-己烯的甲酰化反应相比,树枝状负载催化剂的催化活性较高,但选择性较低。树枝状聚合物负载的膦铑催化剂经4次回收循环催化实验,其对1-己烯的催化活性降低很少,但是其催化选择性降低较多。
Although the catalytic activity of homogeneous catalysts is higher, but the catalyst and organic small molecules of reactant and product separation and catalyst recycling recycling is still a major factor restricting the application of homogeneous catalysts. Conventional separation methods such as distillation, extraction can not be applied to some special effects, for example, the product of a higher boiling point, and the deactivation of the catalyst in the extraction process of regeneration. Easier to recycle and reuse of the heterogeneous catalyst, but limited contact by the contact area due to the catalyst and reactants, the catalytic efficiency and catalytic activity is restricted. Based on this, we designed and fabricated to the dendrimer as a carrier, catalyst loading of small molecules to the dendrimers on the formation of homogeneous catalytic system, dendritic supported catalysts by ion exchange. And catalyst for the hydroformylation reaction of olefins. Details are as follows:
Containing phosphoric acid groups or sulfonic acid groups of the two phenyl xanthene phosphine ligand was prepared from9,9-dimethyl-xanthene, synthesis and structure of the product by NMR and IR characterization results show that, contain phosphate groups, two phenyl xanthene phosphine ligand is more difficult synthesis of diphenyl xanthene phosphine ligands containing sulfonic acid groups were successfully synthesized.
Dendritic polyglycerol as raw material, one-pot1,2-dimethyl imidazole,6-bromhexine chloride prepared by the reaction end groups containing cationic dendrimers. Synthesis containing sodium diphenyl xanthene phosphine ligands and rhodium complexes with dendrimers of small molecules by ion-exchange load in the formation of the dendrimer polymer load phosphine rhodium catalyst. And diphenyl the xanthene phosphine ligand bonded to the polymer on the conditions were optimized, the results show that the ligand and the number of polymer mole ratio of1:2ligand bonded to the polymer the best results.
Will prepared dendrimers load the phosphine rhodium catalysts for the reaction of1-hexene homogeneous catalytic hydroformylation, ultrafiltration recovery study of recovery and recycling of the catalyst on the catalytic activity and selectivity. The results showed that the dendrimer load phosphine rhodium catalyst with small molecule catalyst compared to the1-hexene hydroformylation reaction, the catalytic activity of dendritic load high, but low selectivity. Dendritic polymer supported phosphine rhodium catalyst after four times recycling loop catalytic experiments, the lower the catalytic activity of1-hexene little, but its catalytic selectivity greater reductions.
引文
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