全氟辛基磺酰亚胺及其盐的制备及应用
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摘要
本课题研究了由全氟辛基磺酰氟与氨反应制得全氟辛基磺酰胺,全氟辛基磺酰胺与全氟辛基磺酰氟在三乙胺中回流,得到全氟辛基磺酰亚胺的三乙胺盐,再经过酸性离子交换树脂得到全氟辛基磺酰亚胺。将全氟辛基磺酰亚胺与金属氯化物或醋酸盐在水或有机溶剂中加热制得全氟辛基磺酰亚胺金属盐,并以ICP、IR、19F NMR和元素分析等手段进行表征。
以全氟辛基磺酰亚胺金属盐(M(NPf2)n,M=Yb,Sc,Hf,Sn.n=3,4)为催化剂与全氟萘烷(C10F18)为全氟溶剂组成氟相,反应物和共溶剂组成有机相,研究了氟两相体系中合成二苯甲烷及取代二苯甲烷、14-取代-14H-二苯并[a,j]氧杂蒽类化合物、1-(芳基,酰胺基)甲基-2-萘酚类化合物、苯亚甲基环戊烷并[d]嘧啶酮衍生物、六氢喹啉衍生物、5-氧代-4H-四氢苯并[b]吡喃衍生物、meso-四苯基卟啉衍生物。考察了反应温度、催化剂及其用量、共溶剂种类等因素对合成上述有机物的影响。研究表明,M(NPf2)n为催化剂能有效的催化上述反应的进行,并且反应条件温和、后处理简单、反应速度快、产率高。含有催化剂的氟相通过简单的相分离,就可回收利用,氟相重复使用4次,其催化活性无明显降低。共溶剂的加入方便了产物的分离,使反应物混合均匀有利于反应的进行；但同时降低了反应物浓度,反而使反应受限。
同时本课题研究了用氟硅胶固载氟代催化剂的方法。氟硅胶是一种含有氟烷基的硅胶。利用氟-氟相互作用,可以将带有氟尾的催化剂或配体固定在氟硅胶上。本课题制备了氟硅胶负载的全氟辛基磺酰亚胺及其盐,并以IR、吡啶-FTIR和TGA等手段进行表征。研究了氟硅胶负载全氟辛基磺酰亚胺催化合成缩醛,氟硅胶负载全氟辛基磺酰亚胺铪催化合成N-甲酰胺衍生物和9-芳基-十氢吖啶-1,8-二酮衍生物,反应产率较高,催化剂通过简单的过滤,就可循环利用,催化剂可循环使用数次,催化效果无明显降低。
In this dissertation, the preparation of (C8F17SO2)2NH was performed in three steps. For the first step, perfluorooctanesulfonyl fluoride reacted with ammonia at -20℃to give C8F17SO2NH2. The second step, the mixture of perfluorooctanesulfonamide and perfluorooctanesulfonyl fluoride was refluxed in Et3N to afford (C8F17SO2)2N HNEt3. The last step, (C8F17SO2)2N HNEt3 was introduced into acid ion exchange resins column to give (C8F17SO2)2NH. And metal bis(perfluorooctanesulfonyl)imides were prepared from metal chloride or acetate and bis(perfluorooctanesulfonyl)imide in water or organic solvent. The catalysts obtained were characterized by ICP, IR, 19F NMR and Elemental Analysis.
The mixture of metal bis(perfluorooctanesulfonyl)imide and perfluorinated solvent composed the fluorous phase. The reactants and co-solvent composed the organic phase. In fluorous biphasic system the catalysis efficiency of metal bis(perfluorooctanesulfonyl)imides for synthesis of many useful organic compounds was investigated in details. These model reactions include synthesis of substituted diphenylmethane, 14-substituted-14H-dibenzo[a,j]xanthenes, hexahydroquinoline derivatives, benzylidene cyclopenta[d]pyrimidinone derivatives,5-oxo-4H-terahydrobenzo[b]pyrans, 1-(aryl, amido)methyl-2-naphthols, meso-tetraarylporphyrins. The reaction conditions such as reaction temperature, reaction time, amount of catalyst, co-solvent were optimized. The results show that the aboved mentioned synthesis can be effectively promoted by using metal bis(perfluorooctanesufonyl)imides as catalysts. Generally, the introduction of metal bis(perfluorooctanesulfonyl)imides can offer the synthesis with milder reaction conditions, simpler experimental procedure while higher yields. By simple phase separation the fluorous phase containing catalyst could be reutilized up to four times with consistent reactivity. The addition of co-solvent make the reaction more accessable and the reactants concentration uniform to benefit the reaction. But the concentration of reactants was diluted with the addition of co-solvent which confined the reaction.
At the same time, the method of immobilization fluorous catalysts on fluorous silica gel was studied. Fluorous silica gel has a perfluoroalkyl bonding phase and high affinity toward fluorous compounds. So fluorous catalyst can be absored on fluorous silica gel. In this dissertation, fluorous catalysts were immobilized on fluorous silica gel, and the supported catalysts were characterized by IR, pyridine-FTIR and TGA. Fluorous silica gel supported bis(perfluorooctanesulfonyl)imide or metal bis(perfluorooctanesulfonyl)imide exhibited effective catalytic performances when employed for synthesis of acetals and ketals, formamide derivatives and 9-aryl-1,8-dioxo-decahydroacridines. And the supported catalysts recovered by simple filtration recycled several times (ca 3 times) with consistent reactivity.
以全氟辛基磺酰亚胺金属盐(M(NPf2)n,M=Yb,Sc,Hf,Sn.n=3,4)为催化剂与全氟萘烷(C10F18)为全氟溶剂组成氟相,反应物和共溶剂组成有机相,研究了氟两相体系中合成二苯甲烷及取代二苯甲烷、14-取代-14H-二苯并[a,j]氧杂蒽类化合物、1-(芳基,酰胺基)甲基-2-萘酚类化合物、苯亚甲基环戊烷并[d]嘧啶酮衍生物、六氢喹啉衍生物、5-氧代-4H-四氢苯并[b]吡喃衍生物、meso-四苯基卟啉衍生物。考察了反应温度、催化剂及其用量、共溶剂种类等因素对合成上述有机物的影响。研究表明,M(NPf2)n为催化剂能有效的催化上述反应的进行,并且反应条件温和、后处理简单、反应速度快、产率高。含有催化剂的氟相通过简单的相分离,就可回收利用,氟相重复使用4次,其催化活性无明显降低。共溶剂的加入方便了产物的分离,使反应物混合均匀有利于反应的进行；但同时降低了反应物浓度,反而使反应受限。
同时本课题研究了用氟硅胶固载氟代催化剂的方法。氟硅胶是一种含有氟烷基的硅胶。利用氟-氟相互作用,可以将带有氟尾的催化剂或配体固定在氟硅胶上。本课题制备了氟硅胶负载的全氟辛基磺酰亚胺及其盐,并以IR、吡啶-FTIR和TGA等手段进行表征。研究了氟硅胶负载全氟辛基磺酰亚胺催化合成缩醛,氟硅胶负载全氟辛基磺酰亚胺铪催化合成N-甲酰胺衍生物和9-芳基-十氢吖啶-1,8-二酮衍生物,反应产率较高,催化剂通过简单的过滤,就可循环利用,催化剂可循环使用数次,催化效果无明显降低。
In this dissertation, the preparation of (C8F17SO2)2NH was performed in three steps. For the first step, perfluorooctanesulfonyl fluoride reacted with ammonia at -20℃to give C8F17SO2NH2. The second step, the mixture of perfluorooctanesulfonamide and perfluorooctanesulfonyl fluoride was refluxed in Et3N to afford (C8F17SO2)2N HNEt3. The last step, (C8F17SO2)2N HNEt3 was introduced into acid ion exchange resins column to give (C8F17SO2)2NH. And metal bis(perfluorooctanesulfonyl)imides were prepared from metal chloride or acetate and bis(perfluorooctanesulfonyl)imide in water or organic solvent. The catalysts obtained were characterized by ICP, IR, 19F NMR and Elemental Analysis.
The mixture of metal bis(perfluorooctanesulfonyl)imide and perfluorinated solvent composed the fluorous phase. The reactants and co-solvent composed the organic phase. In fluorous biphasic system the catalysis efficiency of metal bis(perfluorooctanesulfonyl)imides for synthesis of many useful organic compounds was investigated in details. These model reactions include synthesis of substituted diphenylmethane, 14-substituted-14H-dibenzo[a,j]xanthenes, hexahydroquinoline derivatives, benzylidene cyclopenta[d]pyrimidinone derivatives,5-oxo-4H-terahydrobenzo[b]pyrans, 1-(aryl, amido)methyl-2-naphthols, meso-tetraarylporphyrins. The reaction conditions such as reaction temperature, reaction time, amount of catalyst, co-solvent were optimized. The results show that the aboved mentioned synthesis can be effectively promoted by using metal bis(perfluorooctanesufonyl)imides as catalysts. Generally, the introduction of metal bis(perfluorooctanesulfonyl)imides can offer the synthesis with milder reaction conditions, simpler experimental procedure while higher yields. By simple phase separation the fluorous phase containing catalyst could be reutilized up to four times with consistent reactivity. The addition of co-solvent make the reaction more accessable and the reactants concentration uniform to benefit the reaction. But the concentration of reactants was diluted with the addition of co-solvent which confined the reaction.
At the same time, the method of immobilization fluorous catalysts on fluorous silica gel was studied. Fluorous silica gel has a perfluoroalkyl bonding phase and high affinity toward fluorous compounds. So fluorous catalyst can be absored on fluorous silica gel. In this dissertation, fluorous catalysts were immobilized on fluorous silica gel, and the supported catalysts were characterized by IR, pyridine-FTIR and TGA. Fluorous silica gel supported bis(perfluorooctanesulfonyl)imide or metal bis(perfluorooctanesulfonyl)imide exhibited effective catalytic performances when employed for synthesis of acetals and ketals, formamide derivatives and 9-aryl-1,8-dioxo-decahydroacridines. And the supported catalysts recovered by simple filtration recycled several times (ca 3 times) with consistent reactivity.
引文
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