新型多环芳烃功能高分子中间体的制备及其机理研究
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摘要
芳香族聚合物由于具有热稳定性高、化学稳定性好、质地轻且牢固以及良好的加工成型性等优点,受到人们的日益重视。然而其推广应用受到多环芳烃单体制备困难的限制。由芳香族化合物的选择性酰基化、烷基化及偶联等反应,可得到主链型芳香族高分子的中间体,这是功能高分子材料的重要研究方向。较之单环芳烃,多环芳烃中间体电子云密度更高,相应的聚合物热稳定性、化学稳定性更好、质地更为牢固。但目前对芳烃的Friedel-Crafts酰基化、Friedel-Crafts烷基化和偶联等反应的研究主要集中在苯环和萘环,更多环芳香族的研究则显得很薄弱。
本研究首次研究了不同催化剂(金属卤化物、离子液体、杂多酸等)作用下,多环芳烃蒽的Friedel-Crafts酰基化、Friedel-Crafts烷基化反应和苊的偶联反应,得到1,2-蒽乙二酮、9-苯甲酰蒽、2-异丙蒽和3,3'-联苊等多种新型多环芳烃功能高分子中间体。根据各因素对反应的影响结果,蒽、苊及催化剂的结构特点,并结合GC/MS、FT-IR和~1H NMR谱图分析,探讨了上述各反应的反应机理,合理解释了几种新型多环芳烃高分子中间体的生成,取得了如下结果:
1)以[Bmim]Cl-AlCl_3离子液体为催化剂和溶剂,利用蒽与草酰氯的Friedel-Crafts酰基化反应,在温和条件下成功合成了新型功能高分子中间体1,2-蒽乙二酮,用萃取、重结晶等方法得到了1,2-蒽乙二酮纯品,对其用GC、GC/MS、FT-IR和~1H NMR等分析测试手段确认了其结构;根据GC测试结果考察了不同反应条件对1,2-蒽乙二酮产率和选择性的影响,当AlCl_3在[Bmim]Cl-AlCl_3离子液体中的摩尔分数为0.67,n{[Bmim]Cl-AlCl_3}:n(蒽)=2∶1,n(草酰氯):n(蒽)=2∶1,反应温度45℃,反应时间6h时,1,2-蒽乙二酮收率为88.2%,选择性可达98.2%;离子液体表现出了其突出的优势,催化活性高、具有催化剂和溶剂的双重功能、可以重复使用及环境友好等;根据不同反应条件对蒽与草酰氯的Friedel-Craft酰基化的影响,以及蒽和[Bmim]Cl-AlCl_3离子液体的结构特点,探讨了在[Bmim]Cl-AlCl_3离子液体催化作用下,蒽与草酰氯Friedel-Craf酰基化反应的机理,反应属于由草酰氯与离子液体相互作用产生的酰基正离子作为亲电试剂与蒽发生的亲电取代反应机理。
2)用杂多酸型催化剂钨酸铝(AlPW_(12)O_(40))催化了蒽和苯甲酰氯的Friedel-Craft酰基化反应,合成了功能高分子中间体9-苯甲酰蒽,提纯得到其纯品,用GC/MS、FT-IR和~1H NMR等分析测试结果确认了其结构;考察了各种反应条件对9-苯甲酰蒽收率和选择性的影响,得到9-苯甲酰蒽的优化合成条件为:反应温度90℃,反应时间为5h,n(蒽):n(苯甲酰氯):1.0∶1.5,催化剂百分含量为4.5%,溶剂为环己烷。上述条件下,9-苯甲酰蒽的收率和选择性分别可以达到47.4%和91.8%;实验结果表明,AlPW_(12)O_(40)具有对目标产物选择性高、无环境污染且可以回收利用等优点;根据实验结果探讨了杂多酸型磷催化剂钨酸铝催化蒽与苯甲酰氯的Friedel-Craf酰基化的反应机理,通过电子云密度、空间位阻等因素的讨论,对9-苯甲酰蒽的合成做了科学的解释。
3)研究了无水AlCl_3、[Bmim]Cl-AlCl_3离子液体或AlPW_(12)O_(40)催化蒽与2-氯丙烷的Friedel-Craf烷基化反应。温和条件下,合成了高分子中间体2-异丙蒽,萃取、重结晶得到其纯品,GC/MS、FT-IR和~1H NMR等分析测试结果确认了其结构;实验研究了各催化剂作用下的优化反应条件,离子液体的催化效果最好,[Bmim]Cl-AlCl_3催化的优化反应条件下,2-异丙蒽收率和选择性分别为69.2%和为77.1%;对在无水AlCl_3、[Bmim]Cl-AlCl_3离子液体及AlPW_(12)O_(40)催化下,蒽与氯代异丙烷Friedel-Craf烷基化反应制备2-异丙蒽,分别从反应热力学控制与动力学控制等方面对2-异丙蒽的亲电取代机理进行了讨论。
4)分别研究了在BF_3、AlCl_3、FeCl_3等常用无机盐Lewis酸和[Bmim]Cl-AlCl_3、[Bmim]Cl-FeCl_3离子液体催化作用下,苊在温和条件或微波下的偶联反应。实验成功合成了功能高分子中间体3,3'-联苊,并利用旋转蒸发、薄层层析、重结晶等多种提纯方法得到3,3'-联苊纯品。根据提纯物的GC/MS、FT-IR、~1H NMR等谱图确定了其结构。研究了各种催化剂作用下合成3,3'-联苊的最佳反应条件,比较了各类催化剂对3,3'-联苊合成的催化活性的高低。结果表明,[Bmin]Cl-FeCl_3离子液体对3,3'-联苊合成的催化效果最好,在其催化的最佳反应条件下,3,3'-联苊收率为38.5%,选择性达99.1%;利用加入自由基猝灭剂的方法和对反应产物的GC/MS、FT-IR、~1H NMR等谱图分析探讨了各催化剂作用下苊的偶联反应的机理,苊在BF_3·OEt_2和AlCl_3催化作用下的偶联反应,属典型的自由基机理,根据自由基中间的稳定性及链反应的特征,合理解释了3,3'-联苊的生成。而FeCl_3及[Bmin]Cl-AlCl_3和[Bmin]Cl-FeCl_3离子液体催化的苊偶联反应是通过碳正离子历程催化苊得到3,3'-联苊。
In recent years,aromatic polymers are now invoking more and more interests because of their many advantages,such as good thermal and chemical stabilities,low density but robustness and facility to process,but their wider application is limited by the preparation of aromatic monomers(i.e,macromolecule intermediate).Such macromolecule intermediates can be synthesized by selective acylation,alkylation or coupling of aromatics,which is an important research direction of functional macromolecule intermaterials.
So far,the studies of Friedel-Craft acylation,Friedel-Craft alkylation or coupling of aromatics are mainly focused on benzene and naphthalene or their ramifications,while few reports have been found in the literatures on the researchs of polycyclic aromatic hydrocarbons.
In the present dissertation,the Friedel-Craft acylation and Friedel-Craft alkylation of anthracene and the coupling of acenaphthene catalysed by different catalysts(metal halid,ionic liquids and heteropoly acid)were firstly investigated.Several new functional macromolecule intermediates such as 1,2-aceanthrylenedione,9-Benzoylanthracene, 2-isopropylanthracene and 3,3'-biacenaphthene were selectively synthesized.The mechanisms of above reactions were explored by corresponding experimental results,the structure characteristics of anthracene,acenaphthene and catalysts as well as analysis of MS,FT-IR and ~1H NMR.Thus,reasonable analysises of all reaction products were realized.Some significant results are as follows:
1)[Bmim]Cl-AlCl_3 ionic liquid was used as catalyst and solvent in the Friedel-Crafts acylation of anthracene with oxalyl chloride to synthesize the new functional macromolecule intermediates 1,2-aceanthrylenedione, Pure 1,2-aceanthrylenedione was prepared by extraction and recrystalling and the structure of 1,2-aceanthrylenedione was identified by GC/MS, FT-IR and ~1H NMR analysis.The effects of various reaction comditions on the the yield and selectivity of 1,2-aceanthrylenedione were studied by GC analysis.The results showed that the optimum synthesis conditions of the acylation reaction are as follow:the molar fraction of AlCl_3 in [Bmim]Cl-AlCl_3 being 0.67,n{[Bmim]Cl-AlCl_3}:n(anthracene)=2:1, n(oxalyl chloride):n(anthracene)= 2:1,the reaction temperature 45℃and the reaction time 6 h.Under those conditions,the yield of 1,2-aceanthrylenedione is 88.2%and selectivity is 98.2%.Farther more, [Bmim]Cl-AlCl_3 ionic liquid not only shows excellent catalysis activity, dual role as catalyst and solvent,but also can be reuse and has little pollution to environment.The mechanism of the Friedel-Craft acylation of anthracene with oxalyl chloride in the presence of[Bmim]Cl-AlCl_3 was explored by examining effects of various reaction conditions on the yield and selectivity of 1,2-aceanthrylenedione and the structure characteristic of anthracene as well as[Bmim]Cl-AlCl_3 Ionic Liquid.The results show that acylium cation as electrophilic reagent produced by oxalyl chloride interaction with[Bmim]Cl-AlCl_3 ionic liquid attack anthracene.It is belong to electrophilic substitution mechanism.
2)The Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by AlPW_(12)O_(40)heteropolyacid was studied.9-Benzoylanthracene was determined by GC/MS analysis and pure 9-benzoylanthracene was prepared.The structure of 9-benzoylanthracene was confirmed by GC/MS,FT-IR and ~1H NMR,and the effects of various reaction comditions on the the yield and selectivity of 9-benzoylanthracene was studied.The results showed that the most suitable synthesis conditions are solvent cyclohexane,n(benzoyl chloride):n(anthracene)= 2:1,catalyst mass fraction 4.5%,reaction temperature 90℃and reaction time 5 hour.Under those conditions,the yield of 9-benzoylanthracene is 47.4%and the selectivity towardes 9-benzoylanthracene is 91.8%.Additionally, AlPW_(12)O_(40)has no pollution to environment and can be easily recovered after the reaction for reused.Preparation of 9-benzoylanthracene was scientific discussed by studying the mechanism of the Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by AlPW_(12)O_(40) through analyzing the density of electron cloud and interspace obstacle of anthracene,characteristic of AlPW_(12)O_(40)and experimental results.
3)The Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by anhydrous AlCl_3,[Bmim]Cl-AlCl_3 ionic liquid and AlPW_(12)O_(40)heteropolyacid was studied.2-isopropylanthracene,which was used as new macromolecule intermediate was determined by GC/MS. Pure 2-isopropylanthracene was obtained by extraction and recrystalling the reaction mixture and its strcture was determined through GC/MS, FT-IR and ~1H NMR.Optimum synthesis conditions were gained by examining the effects of various reaction comditions on the yield and selectivity of 2-isopropylanthracene.Among the three catalysts, [Bmim]Cl-AlCl_3 ionic liquid has the highest catalysis activity on the Friedel-Craft acylation of anthracene with oxalyl chloride.Under the optimum reaction conditions catalysed by[Bmim]Cl-AlCl_3,yield and selectivity of 2-isopropylanthracene is 47.4%and 91.8%.The reaction mechanisms of the preparation of 2-isopropylanthracene were explained with electrophilic substitution,which was discussed from the aspect of thermodynamics control and kinetics control,erespectively.
4)The coupling reaction of acenaphthene catalyzed by Lewis acids (AlCl_3,FeCl_3,BF_3-OEt_2)and ionic liquids([Bmim]Cl-AlCl_3,[Bmim]Cl-FeCl_3) were investigated at room temperature,ambient atmosphere or under microwave radiation.3,3'-biacenaphthenyls,which canbe used as new intermediate of function aromatic polymer material,was successfully synthesized.Pure 3,3'-biacenaphthenyls was purified by rotary evaporation,recrystallization and chromatography,and its structure was characterized by GC /MS,FT-IR,~1H NMR.The optimun reaction conditions were studied and the catalysis activity of different catalysts were compared.The results showed that[Bmim]Cl-FeCl_3 ionic liquid is the best effective catalysis among above of them on the preparation of 3,3'-biacenaphthenyls and under the optimum reaction conditions catalysed by[Bmim]Cl-FeCl_3,the yield of 3,3'- biacenaphthenyls is 38.5%and the selectivity towardes 3,3'- biacenaphthenyls is 99.1%.The mechanism of coupling reaction was discussed through the method of adding free radical scavenger and the analysis of MS,FTIR and ~1H NMR.The resuts suggest that the coupling reaction catalyzed by AlCl_3 and BF_3·OEt_2 are belong to typical free radical mechanism,while those of catalyzed by FeCl_3, [Bmin]Cl-AlCl_3 and[Bmin]Cl-FeCl_3 are proceed along carbonium mechanism to produce 3,3'-biacenaphthenyls.
本研究首次研究了不同催化剂(金属卤化物、离子液体、杂多酸等)作用下,多环芳烃蒽的Friedel-Crafts酰基化、Friedel-Crafts烷基化反应和苊的偶联反应,得到1,2-蒽乙二酮、9-苯甲酰蒽、2-异丙蒽和3,3'-联苊等多种新型多环芳烃功能高分子中间体。根据各因素对反应的影响结果,蒽、苊及催化剂的结构特点,并结合GC/MS、FT-IR和~1H NMR谱图分析,探讨了上述各反应的反应机理,合理解释了几种新型多环芳烃高分子中间体的生成,取得了如下结果:
1)以[Bmim]Cl-AlCl_3离子液体为催化剂和溶剂,利用蒽与草酰氯的Friedel-Crafts酰基化反应,在温和条件下成功合成了新型功能高分子中间体1,2-蒽乙二酮,用萃取、重结晶等方法得到了1,2-蒽乙二酮纯品,对其用GC、GC/MS、FT-IR和~1H NMR等分析测试手段确认了其结构;根据GC测试结果考察了不同反应条件对1,2-蒽乙二酮产率和选择性的影响,当AlCl_3在[Bmim]Cl-AlCl_3离子液体中的摩尔分数为0.67,n{[Bmim]Cl-AlCl_3}:n(蒽)=2∶1,n(草酰氯):n(蒽)=2∶1,反应温度45℃,反应时间6h时,1,2-蒽乙二酮收率为88.2%,选择性可达98.2%;离子液体表现出了其突出的优势,催化活性高、具有催化剂和溶剂的双重功能、可以重复使用及环境友好等;根据不同反应条件对蒽与草酰氯的Friedel-Craft酰基化的影响,以及蒽和[Bmim]Cl-AlCl_3离子液体的结构特点,探讨了在[Bmim]Cl-AlCl_3离子液体催化作用下,蒽与草酰氯Friedel-Craf酰基化反应的机理,反应属于由草酰氯与离子液体相互作用产生的酰基正离子作为亲电试剂与蒽发生的亲电取代反应机理。
2)用杂多酸型催化剂钨酸铝(AlPW_(12)O_(40))催化了蒽和苯甲酰氯的Friedel-Craft酰基化反应,合成了功能高分子中间体9-苯甲酰蒽,提纯得到其纯品,用GC/MS、FT-IR和~1H NMR等分析测试结果确认了其结构;考察了各种反应条件对9-苯甲酰蒽收率和选择性的影响,得到9-苯甲酰蒽的优化合成条件为:反应温度90℃,反应时间为5h,n(蒽):n(苯甲酰氯):1.0∶1.5,催化剂百分含量为4.5%,溶剂为环己烷。上述条件下,9-苯甲酰蒽的收率和选择性分别可以达到47.4%和91.8%;实验结果表明,AlPW_(12)O_(40)具有对目标产物选择性高、无环境污染且可以回收利用等优点;根据实验结果探讨了杂多酸型磷催化剂钨酸铝催化蒽与苯甲酰氯的Friedel-Craf酰基化的反应机理,通过电子云密度、空间位阻等因素的讨论,对9-苯甲酰蒽的合成做了科学的解释。
3)研究了无水AlCl_3、[Bmim]Cl-AlCl_3离子液体或AlPW_(12)O_(40)催化蒽与2-氯丙烷的Friedel-Craf烷基化反应。温和条件下,合成了高分子中间体2-异丙蒽,萃取、重结晶得到其纯品,GC/MS、FT-IR和~1H NMR等分析测试结果确认了其结构;实验研究了各催化剂作用下的优化反应条件,离子液体的催化效果最好,[Bmim]Cl-AlCl_3催化的优化反应条件下,2-异丙蒽收率和选择性分别为69.2%和为77.1%;对在无水AlCl_3、[Bmim]Cl-AlCl_3离子液体及AlPW_(12)O_(40)催化下,蒽与氯代异丙烷Friedel-Craf烷基化反应制备2-异丙蒽,分别从反应热力学控制与动力学控制等方面对2-异丙蒽的亲电取代机理进行了讨论。
4)分别研究了在BF_3、AlCl_3、FeCl_3等常用无机盐Lewis酸和[Bmim]Cl-AlCl_3、[Bmim]Cl-FeCl_3离子液体催化作用下,苊在温和条件或微波下的偶联反应。实验成功合成了功能高分子中间体3,3'-联苊,并利用旋转蒸发、薄层层析、重结晶等多种提纯方法得到3,3'-联苊纯品。根据提纯物的GC/MS、FT-IR、~1H NMR等谱图确定了其结构。研究了各种催化剂作用下合成3,3'-联苊的最佳反应条件,比较了各类催化剂对3,3'-联苊合成的催化活性的高低。结果表明,[Bmin]Cl-FeCl_3离子液体对3,3'-联苊合成的催化效果最好,在其催化的最佳反应条件下,3,3'-联苊收率为38.5%,选择性达99.1%;利用加入自由基猝灭剂的方法和对反应产物的GC/MS、FT-IR、~1H NMR等谱图分析探讨了各催化剂作用下苊的偶联反应的机理,苊在BF_3·OEt_2和AlCl_3催化作用下的偶联反应,属典型的自由基机理,根据自由基中间的稳定性及链反应的特征,合理解释了3,3'-联苊的生成。而FeCl_3及[Bmin]Cl-AlCl_3和[Bmin]Cl-FeCl_3离子液体催化的苊偶联反应是通过碳正离子历程催化苊得到3,3'-联苊。
In recent years,aromatic polymers are now invoking more and more interests because of their many advantages,such as good thermal and chemical stabilities,low density but robustness and facility to process,but their wider application is limited by the preparation of aromatic monomers(i.e,macromolecule intermediate).Such macromolecule intermediates can be synthesized by selective acylation,alkylation or coupling of aromatics,which is an important research direction of functional macromolecule intermaterials.
So far,the studies of Friedel-Craft acylation,Friedel-Craft alkylation or coupling of aromatics are mainly focused on benzene and naphthalene or their ramifications,while few reports have been found in the literatures on the researchs of polycyclic aromatic hydrocarbons.
In the present dissertation,the Friedel-Craft acylation and Friedel-Craft alkylation of anthracene and the coupling of acenaphthene catalysed by different catalysts(metal halid,ionic liquids and heteropoly acid)were firstly investigated.Several new functional macromolecule intermediates such as 1,2-aceanthrylenedione,9-Benzoylanthracene, 2-isopropylanthracene and 3,3'-biacenaphthene were selectively synthesized.The mechanisms of above reactions were explored by corresponding experimental results,the structure characteristics of anthracene,acenaphthene and catalysts as well as analysis of MS,FT-IR and ~1H NMR.Thus,reasonable analysises of all reaction products were realized.Some significant results are as follows:
1)[Bmim]Cl-AlCl_3 ionic liquid was used as catalyst and solvent in the Friedel-Crafts acylation of anthracene with oxalyl chloride to synthesize the new functional macromolecule intermediates 1,2-aceanthrylenedione, Pure 1,2-aceanthrylenedione was prepared by extraction and recrystalling and the structure of 1,2-aceanthrylenedione was identified by GC/MS, FT-IR and ~1H NMR analysis.The effects of various reaction comditions on the the yield and selectivity of 1,2-aceanthrylenedione were studied by GC analysis.The results showed that the optimum synthesis conditions of the acylation reaction are as follow:the molar fraction of AlCl_3 in [Bmim]Cl-AlCl_3 being 0.67,n{[Bmim]Cl-AlCl_3}:n(anthracene)=2:1, n(oxalyl chloride):n(anthracene)= 2:1,the reaction temperature 45℃and the reaction time 6 h.Under those conditions,the yield of 1,2-aceanthrylenedione is 88.2%and selectivity is 98.2%.Farther more, [Bmim]Cl-AlCl_3 ionic liquid not only shows excellent catalysis activity, dual role as catalyst and solvent,but also can be reuse and has little pollution to environment.The mechanism of the Friedel-Craft acylation of anthracene with oxalyl chloride in the presence of[Bmim]Cl-AlCl_3 was explored by examining effects of various reaction conditions on the yield and selectivity of 1,2-aceanthrylenedione and the structure characteristic of anthracene as well as[Bmim]Cl-AlCl_3 Ionic Liquid.The results show that acylium cation as electrophilic reagent produced by oxalyl chloride interaction with[Bmim]Cl-AlCl_3 ionic liquid attack anthracene.It is belong to electrophilic substitution mechanism.
2)The Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by AlPW_(12)O_(40)heteropolyacid was studied.9-Benzoylanthracene was determined by GC/MS analysis and pure 9-benzoylanthracene was prepared.The structure of 9-benzoylanthracene was confirmed by GC/MS,FT-IR and ~1H NMR,and the effects of various reaction comditions on the the yield and selectivity of 9-benzoylanthracene was studied.The results showed that the most suitable synthesis conditions are solvent cyclohexane,n(benzoyl chloride):n(anthracene)= 2:1,catalyst mass fraction 4.5%,reaction temperature 90℃and reaction time 5 hour.Under those conditions,the yield of 9-benzoylanthracene is 47.4%and the selectivity towardes 9-benzoylanthracene is 91.8%.Additionally, AlPW_(12)O_(40)has no pollution to environment and can be easily recovered after the reaction for reused.Preparation of 9-benzoylanthracene was scientific discussed by studying the mechanism of the Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by AlPW_(12)O_(40) through analyzing the density of electron cloud and interspace obstacle of anthracene,characteristic of AlPW_(12)O_(40)and experimental results.
3)The Friedel-Craft acylation of anthracene with oxalyl chloride catalysed by anhydrous AlCl_3,[Bmim]Cl-AlCl_3 ionic liquid and AlPW_(12)O_(40)heteropolyacid was studied.2-isopropylanthracene,which was used as new macromolecule intermediate was determined by GC/MS. Pure 2-isopropylanthracene was obtained by extraction and recrystalling the reaction mixture and its strcture was determined through GC/MS, FT-IR and ~1H NMR.Optimum synthesis conditions were gained by examining the effects of various reaction comditions on the yield and selectivity of 2-isopropylanthracene.Among the three catalysts, [Bmim]Cl-AlCl_3 ionic liquid has the highest catalysis activity on the Friedel-Craft acylation of anthracene with oxalyl chloride.Under the optimum reaction conditions catalysed by[Bmim]Cl-AlCl_3,yield and selectivity of 2-isopropylanthracene is 47.4%and 91.8%.The reaction mechanisms of the preparation of 2-isopropylanthracene were explained with electrophilic substitution,which was discussed from the aspect of thermodynamics control and kinetics control,erespectively.
4)The coupling reaction of acenaphthene catalyzed by Lewis acids (AlCl_3,FeCl_3,BF_3-OEt_2)and ionic liquids([Bmim]Cl-AlCl_3,[Bmim]Cl-FeCl_3) were investigated at room temperature,ambient atmosphere or under microwave radiation.3,3'-biacenaphthenyls,which canbe used as new intermediate of function aromatic polymer material,was successfully synthesized.Pure 3,3'-biacenaphthenyls was purified by rotary evaporation,recrystallization and chromatography,and its structure was characterized by GC /MS,FT-IR,~1H NMR.The optimun reaction conditions were studied and the catalysis activity of different catalysts were compared.The results showed that[Bmim]Cl-FeCl_3 ionic liquid is the best effective catalysis among above of them on the preparation of 3,3'-biacenaphthenyls and under the optimum reaction conditions catalysed by[Bmim]Cl-FeCl_3,the yield of 3,3'- biacenaphthenyls is 38.5%and the selectivity towardes 3,3'- biacenaphthenyls is 99.1%.The mechanism of coupling reaction was discussed through the method of adding free radical scavenger and the analysis of MS,FTIR and ~1H NMR.The resuts suggest that the coupling reaction catalyzed by AlCl_3 and BF_3·OEt_2 are belong to typical free radical mechanism,while those of catalyzed by FeCl_3, [Bmin]Cl-AlCl_3 and[Bmin]Cl-FeCl_3 are proceed along carbonium mechanism to produce 3,3'-biacenaphthenyls.
引文
[1]Song C,Schobert H H.Opportunities for developing specialty chemicals and advanced materials from coals[J].Fuel Processing Technology,1993,34:157-196
[2]孙永周.开展我国聚醚酮酮研究的建议[J].塑料工业,1990(2):25-29
[3]Song C S,Schobert H H.Prepri hydrogen-transferring pyrolysis of cyclic and straight-chain hydrocarbons[3].Am Chem Soc Div Fuel Chem Prepr,1992,37(2):524-532
[4]Scindvasan R,Farora M F.Polymerization of poly(Q-phenylenevinylene)and polyaniline.polymBull[J],1988,20:359-363
[5]Rose J B.Br P,1558671.1976
[6]张伟亚,张少文,吴采樱,等.杯芳烃衍生聚合物用作毛细管气相色谱固定相的研究[J].高等学校化学学报,1997,18(8):1296-1299
[7]Jaime C,Mendoza J D,Prados P,et al.~(13)C NMR chemical shifts:A single rule to determ ine the confo rmation of calix[4]arenes[J].J Org Chem,1991,56(10):3372-3376
[8]钟振林,李建森,卢雪然,等.逐步法合成杯[4]芳烃关环反应的改进[J].高等学校化学学报,1998,19(1):83-85
[9]Miller T M,Neenan T X.Ritic D.Analogues of engineering Plastics:A general one-step synthesis of dendritic polyaryl ethers[3].J Am Chem Soc,1993,115(1):356-357
[10]Miller T M,Neenan T X,Zayas R,et al.X,Zayas R et al.Synthesis and characterization of a series of monodisperse 1,3,5-phenlene-based hydrocarbon dendritic including C_(276)H_(186)and their Fluo rinated a nalogues[J].J Am Chem Soc,1992,114(3):1018-1025
[11]Moore J S.P Reparation of soluble starburst polymer with 127 benzalcyclics containing ethynylenzene unit angew[J].Chem,Int Ed Engl,1993,32:246-251
[12]Serrone S,Denti G,Gap istran S.Synthesis of denddrners containing 22 ruthenium ions and 22'-bipyddine on the surface angew[J].Chem Int Ed Engl,1992,31:1493-1499
[13]石高全,薛奇,金士.萘在三氟化硼乙醚溶液中的电化学聚合[J].高等学校化学学报,1993,14(11):1623-1624
[14]王长松,周本濂.可溶性聚吡咯复合导电薄膜的研制[J].高等学校化学学报,1999,20(2):315-317
[15]Jovanovic S V,Morris D G,Pliva C N.Laser flash photolysis of dinaphthyl ketones[J].Journal of photochemistry and photohiology.A:chemistry,1997,107(1):153-158
[16]魏贤勇,宗志敏,陈茺,等.面向21世纪的煤化工[J].华北地质矿产杂志,1996,11(1):1-8
[17]Pearson D E,Calvin A.Friedel-Crafts acylations with little or no catalyst[J].Synthesis,1972,55(8):533-542
[18]邓建元.芳酮聚合物[J].化工新型材料,1997,3:13-17
[19]胡文祥,恽榴红,张连锋.芳香稠环取代酰氯的合成[J].药学学报,1997,32(9):699-703
[20]李鸿州,高天星.光引发剂的发展概况[J].甘肃化工,2000,2:54.
[21]程其时,马永国.二苯甲酮类紫外吸收剂的发展趋势[J].中国塑料,1996,6:3-11
[22]Singn R P,Kamble R M,Chandra K L,et al.An efficient method for aromatic Friedel-crafts alkylation,acylation,benzoylation,and sulfonylation reactions[J].Tetrahedron,2001,57:241-247
[23]何志荣,张莉霞,朱凌皓.2,6—萘二甲酸及其酯的制备和应用[J].煤化工,2001(1):51-54
[24]王月梅,沈健.苯与长链烯烃烷基化反应催化剂的研究进展[J].广州化工,2004,32(4):4-6
[25]赵仁殿.芳烃工学[M].北京:化学工业出版社,1994,234
[26]徐克勋.精细有机化工原料及中间体[M].北京:化学工业出版社,2002
[27]梁锋,徐丙根,施小红,等.湿式氧化法脱硫的技术进展[J].现代化工,2003:21-24
[28]秦伟程.2-烷基蒽醌合成技术与应用市场[J].化工中间体,2004,1(1):10-17
[29]陆军民.苯乙酸生产方法综述[J].应用化工,2001,30(2):10-12
[30]张邦乐,何炜,张生勇.萘普生的催化不对称合成[J].1999,30(9):426-430
[31]舒歌平,陈鹏,杜淑凤.从煤焦油中制取2,6-二烷基萘的研究[J].煤炭转化,1997,20(3):13-18
[32]谢萍 陆道惠,黄琦,等.热致液晶聚合物-含萘环主成分为对羟基苯甲酸的全芳香族共聚酯[J].高分子通讯,1985,4:269-273
[33]林国强,陈耀全,陈新滋,等.手性合成-不对称反应及其应用[M].科学出版社,北京,2002:332
[34]李林涛,麻生明.以N-杂环卡宾为配体的金属络合物催化有机合成的反应[J].有机化学,2001,21(1):75-81
[35]Buhr C A,Matteucci M D,Froehler B C.Synthesis of a tetracyclic 2'-deoxyadenosine analog[J].Tetrahedron Lett,1999,40:8969-8970
[36]Olivera R,SanMartin R,Tellitu I,et al.The amine exchange/biaryl coupling sequence:a direct entry to the phenanthro[9,10-d]heterocyclic framework[J].Tetrahedron,2002,58:3021-3037
[37]Kang S K,Kim J S,Yoon S K,et al.Copper-catalyzed coupling of polymer bound iodide with organostannanes[J].Tetrahedron Letter,1998,39:3011-3012
[38]Pain C,Celanire S,Guillaumet G,et al.Synthesis of 5-substituted 2-(4-or 3-methoxyphenyl)-4(1H)-quinolones[J].Tetrahedron,2003,59:9627-9633
[39]Wang Q,Wol M,Polar T L,et al.Inhibition of neuraminidase with neuraminic acid C-glycosides[J].Chemistry Letters,2000,10:941-944
[40]Bryant H Y,Stephen L B.Palladium-catalyzed amination of aryl halides and sulfonates[J].Chemistry,1999,576:125-146
[41]Corma A,Garc'la H,Leyva A,et al.Alkali-exchanged sepiolites containing palladium as bifunctional(basic sites and noble metal)catalysts for the Heck and Suzuki reactions[J]. General,2004,257:77-83
[42]Bringmann G,Pfeifer R M,Schreiber P,et al.The 'Lactone Method':Enantioselective preparation of novel P,N-biaryl ligands and their use in the synthesis of the biarylic alkaloids,ancistrotanzanine B and ancistroealaine A[J].Tetrahedron,2004,60:4349-4360
[43]Corma A,Garc'la H,Leyva A,et al.Alkali-exchanged sepiolites containing palladium as bifunctional(basic sites and noble metal)catalysts for the Heck and Suzuki reactions[J].General,2004,257:77-83
[44]Bringmann G,Lang G,Michel M,et al.Stereochemical assignment of the fungal metabolite xestodecalactone A by total synthesis[J].Tetrahedron Letters,2004,45:2829-2831
[45]Abhishek S,Raj M,Raghunath V.Rate enhancement in palladium catalyzed Heck reactions by Lewis acid promoters[J].Catalysis Communications,2007,8:183-186
[46]Iyer S,Ramesh C,Sarkar A,etal.The vinylation of aryl and vinyl halides catalyzed by copper salts[J].Tetrahedron Letters,1997,38:8113-8116
[47]Annamaria C,Maria S,Marsich N,et al.Oxidative coupling of 2,6-dimethylphenol to polyphenylene ether catalyzed by a dinuclear Cu(Ⅱ)dihydroxo-diiodo complex of 2,2'-dipyridylamine[J].Chemical,1996,112:353-365
[48]Noji M,Nakajima M,Koga K.A new catalytic system for aerobic oxidative coupling of 2-naphthol derivatives by the use of CuCl-amine complex:A practical synthesis of binaphthol derivatives[J].Tetrahedron Lett,1994,35:7983-7984
[49]Iwata M,Maegawa T,Kita Y,et al.Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(Ⅲ)reagent[J].Tetrahedron Letter,2002,43:9241-9244
[50]Kodama S,Takita H,Kajimoto T,et al.Synthesis of amaryllidaceae alkaloids,aiculine,oxocrinine,epicrinine,and buflavine[J].Tetrahedron,2004,60:4901-4907
[51]Studer A,Bossart M,Vasella T,et al.Supported palladium catalysts for fine chemicals synthesis[J].Chemical,2001,173:3-18
[52]Escolano C,Jones K.Aryl Radical Cyclisation Onto Pyrroles:A divergent synthesis of spiropyrrolidinyloxindoles and pyrroloquinolines[J].Tetrahedron Letters,2000,41:8951-8955.
[53]Sugden S,Wilkins H.CLVXIL- the Preacher and Chemical Constitution Part Ⅶ:Fused metals and salts[J].Chem.Soc.,1929,7:1291-1293
[54]Chum H L,Koch V R,Miler L,et al.Electrochemical scrutiny of organmetallic iron complexes andhexmethlbenzene in a room temperature molten salt[J].J.Am.Chem.Soc,1975,97:3264-3270
[55]Wilkes J S,Zaworotko M J.Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids[J].J.Chem.Soc.Commun,1992,965-967
[56]赵忠奎,袁冰,李宗石,等.环境友好的离子液体及其在付-克反应中的应用[J].中国基础科学·科学前沿,2004,1:20-25
[57]张玉芬,乔聪震,张金昌,等.离子液体-环境友好的溶剂和催化剂[J].化学反应工程与工艺,2003,19(2):164-170
[58]张所波,于孟贤,高连勋.离子液体在有机反应中的应用[J].有机化学,2002,22(3):159-165
[59]Wikes J S,Mamantov G,Marassi R.Mathematical and physical sciences[J].D.Reichel Publishing Company,1987,202:405-416.
[60]Boon J A,Levisky J A,Pflug J L,et al.Friedel-Crafts reactions in ambient-temperature molten salts[J].J Org Chem,1986,51:480-483
[61]James R,Xiao J L.Friedel-Crafts acylation reactions using metal triflates in ionic liquid[J].Green chemistry,2002,4:129-133
[62]Rebeiro G L,Khadilkar B M.Microwave assisted aromatic nucleophilie substitution reaction under solventless condition[J].Synth.Commun,2003,33(8):1405
[63]Adama C J,Earle M J,Robertsq,et al,Friedel-Crafts Reactions in Room Temperature Ionic Liquids[J].Chem Common,1998,20:2097-2098
[64]Hao Z K,Li Z S,Wang G R,et al.Friedel-Crafts alkylation of 2-methylnaphthalene in room temperature ionic liquids[J].Appl.Catal.A-General,2004,262(1):69-73
[65]Qiao K,Yokoyama C.Novel acidic ionic liquids catalytic systems for Friedel-Crafts alkylation of aromatic compounds with alkenes[J].Chem.Lett.,2004,33(4):472-473
[66]Xiao L,Johnson K E,Treble R G.Alkane cracking,alkene polymerization,and Riedel-Crafts alkylation in liquids conraining the acidic anions HX_2~- XH(AlX4)`-,XH(AI_2X_7)~-,and Al_2X_7(X=chlorine,bromine)[J].J.Mol.Catal.A:Chem.,2004,214(1):121-127
[67]Freemantle M.Designer solvents-ionic liquids may boost clean technology development[J].Chem.Eng.News,1998,76(12):32-37
[68]Song C E,Shim W H,Roh E J,et al.Scandium(1I1)triflate immobilised in ionic liquids:A novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes[J].Chem.Commun.,2000,(17):1695-1696
[69]Qiao K,Deng Y Q.Alkylations of benzene in room temperature ionic liquids modified with HCI[J].Journal of Molecular Catalysis,2001,171:81-84
[70]Abdul-Sada A K,Atkins M P,Ellis B.Alkylation process[P].US 59-94602,1999
[71]Blanco C G,Banciella D C.Alkylation of naphthalene using three different ionic liquids[J].Journal of Molecular Catalysis A:253,2006,203-206
[72]李艳伟,白雪峰.氯铝酸盐离子液体催化β-甲基萘岐化反应[J].精细石油化工,2006,23(2):18-21
[73]Wartyn J E,Paul B.Regioselectice alkylation in ionic liquids[J].Chem.Commun,1998,20:2245-2246
[74]Ranu B C,Banerjee S.The dramatic influence of a task-specific ionic liquidI[bmIm]OH in michael addition of active methylene compounds to conjugated ketones,carboxylic esters,and nitriles[J].Organic Letters,2005,7(14):3049-3052
[75]Dere R,Pal R R,Patil P P.et al.Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction[J].Tetrahedron Lett,2003,44:5351-5353
[76]Pimenov A A,Makarova N V.Moiseev I K,et al.Reactions of CH acids with a.b-nsaturated ketones of the adamantare series[J].Russian Journal of Organic Chemistry,2001,31(12):1872-1873
[77]Lee C W.Diels-Alder reactions in chloroaluminate ionic liquids:acceleration and selectivity enhancement[J].Tetrahedron Lett,1999,40:2461-2464
[78]Meracz I,Taeboem Oh.Asymmetric Diels-Alder reactions in ionic liquids[J].Tetrahedron Letters,2003.(44):6465-6468
[79]Potdar K,Mohile S S,Salunkhe M M.Coumarin syntheses via pechmann condensation in Lewis acidic chloroaluminate ionic liquid[J].Tetrahadron letters,2001,42:9285-9287
[80]Harjani J R,Nara S J.Salunkhe.Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation[J].Tetrahadron Letters,2002,43:1127-1130
[81]Howarth J,James P,Ryan R.Sodium borohydride reduction of aldehydes and ketones in the recyclable ionic liquid[bmim]PF_6[J].Synth Commun,2001,31(19):2935-2942
[82]Chen W,Xu L,Chatterton C,et al.Palladium catalysed allylation reactions in ionic liquids[J].Chem Commun,1999(13):1247-1248
[83]Howarth,J.Oxidation of aromatic aldehydes in the ionic liquid[bmim]PFr[J].Tetrahedron Lett,2000,41:6627-6629
[84]Carmichael A J,Earle M J,Holbrey J D,et al.The Heck reaction in ionic liquids:A multiphasic catalyst system[J].Org.Lett,1999,1:997-1000
[85]Horvath I T,Rabai J.Facilec Catalyst separation with out water:Fluorous biphase hydyoformylation of olefins[J].Science,1994,266:72-74
[86]Kabalka G W,Malladi R R.Reduction of aldehydes using tdalkylboranes in ionic liquids[J].Chem.Commun.,2000,22:2191-2192
[87]Reynolds J L,Erdner K R,Jones P B.Photoreduction of benzophenones by amines in room temperature ionic liquids[J].Org.Lett,2002,4:917-919
[88]许林,郭军.杂多酸型催化剂的应用及其进展[J].石油化工,1994,23(7):477-481
[89]Kuroda Y,Kunai A,Hamada M,et al.J.Catalytic oxidation of naphthalene on palladium in cooperation with copper(Ⅰ)(Ⅱ)redox couple[J].Bull.Chem.Soc.Jpn.1991,64:3089-3093
[90]梁娟,王善均.催化剂新材料,北京:化学工业出版社,1990.79-86
[91]Kozhevnikov I V.Heteropoly acids and related compounds as catalysts for fine chemical synthesis[J].Catal.Rev.Sci.Eng.,1995,37(2):311-352
[92]Okuhara T,Mizuno N,Misono M.Advances in catalysis[C].London:Acdemic Press,1996,41:113-252
[93]王兴平,叶兴凯,吴越.活性炭表面固载十二硅钨酸地表征[J].催化学报,1995,16(6):510-513
[94]吴越,叶兴凯,杨向光,等.杂多酸的固载化—关于制备负载型酸催化剂的一般原理[J].分 子催化,1996,10(4):299-319
[95]Lzumi Y,Urabe K,Onaka M.et al.Clay and heteropoly acid in oraganic reactions[M].Kodnsha/VCH,Tokyo,1992:187-191
[96]赵振波,孙闻东,杨向光,等.用高浓度杂多酸溶液催化苯甲酸与乙酸酐的酰化反应[J].催化学报,2001,22(3):299-300
[97]Lzumi Y,Ogwa M,Nohara W,et al.Alkali metal salts andammonium salts of Keggin-type heteropolyacids as solid acid catalysts for liquid-phase Friedel-Crafts reactions[J].Appl Catal A:General1995,132:127-140
[98]Tagawa T,Amemiya J,Goto S.Chlorine-free Friedel-crafts acylation benzene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl Catal A:General 2004,257:19-23
[99]Firouzabadi H,Iranpoor N,Nowrouzi F.AlPW_(12)O_(40)as a non-hygroscopic Lewis acid catalyst for the efficient Fdedel-Crafts acylation of aromatic compounds under solvent-less conditions[J].Tetrahedron letters,2004,60:10843-10850
[100]Kaur J,Kozhevnikov I V.Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalysed by heteropoly salt Cs_(2.5)H_(0.5)[-PW12O40][J].Chem.commun,2002,18:2508-2509
[101]Tagawa T,Junichl A,Shlgeo G.Chlorine-free Fdedel-Crafts acylation of benezene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl.Catal.A:General,2004,257:19-23
[102]长谷部,连奥田,曲正.乙苯的制备方法[P].JP Patentt 525062,1993,02
[103]刘琪英,王军,武文良,等.硅胶负载的磷钨酸催化剂上萘的异丙基化反应[J].南京工业大学学报,2003,25(1):23-27.
[104]于清跃,武文良,王军等.萘与异丙醇γ-Al2O3负载的磷钨酸催化剂上烷基化[J].南京工业大学学报,2004,26(2):24-27.
[105]胡长文,高丽娟,王恩波,等.钨系Keggin结构杂多酸的酸强度及催化反应特性[J].东北师范大学学报(自然辩学版),1995,2(2):62-70
[106]秦玉楠.钼系杂多酸催化剂的结构、性能、制备和应用前景[J].中国钼业,2001,25(2):20-24
[107]Hou Z Y,Okuhara T,yoshioka H,et al.Catalytic synthesis of diphenylmethane from benzene and formalin with water-tolerant solid acids[J].Applied Catalysis A:General,2001,216:147-155.
[108]张敏.活性炭负载磷钨酸催化合成环己酮缩乙二醇[J].化学研究,2001,12(3):44-45
[109]迟洪盘,吴通好,李玉燕.杂多酸类催化剂的研究进展[J].齐鲁石油化工,1994,22(3):222-229
[110]Sato H,Nagai K,Yoshioka H.Vapor phase nitration of benzene over solid acid catalysts Ⅲ.Nitration with nitric acid(2);mixed metal oxide treated with sulfuric acid and heteropolyacid partially neutralized,Applied Catalysis A:General,1998,175:209-213
[111]Ono Y,Baba T.Selective reactions over solid base catalysts[J].Catalysis Today,1997,38:321-337
[112]陈景林,林青松,蒋山.气相硝化制备硝基苯的研究[J].分子催化,2001,15(2):119-123
[113]陈景林,林青松,吕连海,等.负载型磷钨酸催化苯气相硝化[J].石油化工,2001,30(1):1719
[114]许林,胡长文,王恩波.杂多酸型催化剂的研究进展[J].石油化工,1997,26(9):632-637
[115]许林,郭军.杂多酸型催化剂的研究进展[J].石油化工,1994,23(7):477-482
[116]Matveev K I,Odyakov V F,Zhizhiza E G.Heteropoly acids as oxidation catalysts in synthesis of K-vitamins[J].Journal of Molecular Catalysis A:Chemical,1996,114:151-160
[117]Jiang H S,Mao X,Xie X J,et al.Partially reduced heteropoly compound catalysts for the selective oxidation of propane[J].Journal of Molecular Catalysis A:Chemical,2000,185:143-149
[118]Futura M,Kung M C,Kung H H.One-step synthesis of ethyl acetate from ethene and oxygen[J].Applied Catalysis A:General,2000,201:L9-L11
[119]Jovanovic S V,Morris D G,Pliva C N.Laser flash photolysis of dinaphthyl ketones[J].Journal of photochemistry and photohiologyA:chemistry,1997,107(1):153-158
[120]李靖,廖祥军,刘华,等.3-溴丙基苯的傅克酰基化反应的研究[J].化学研究,1998,9(3):18-20
[121]Sommai P A,Kazumi O,Masahiro M.Acylation of 2-methoxynaphthalene with acyl chlorides in the presence of a catalytic amount of Lewis acids[J].Chem.Soc,1994,69(1):1703-1707
[122]王志萍,李露,于世涛,等.中孔分子筛Zr-Mo-MCM-41催化2-甲氧基萘傅克酰基化反应[J].青岛科技大学学报,2003,24(6):479-483
[123]Deutsch J,Prescott H A.Acylation of naphthalenes and anthracene on sulfated zirconia[J].Journal of catalysis,2005,231(2):269-278
[124]王葆仁.有机合成反应(下册)[M].北京:科学出版社,1985
[125]赵辉爽.离子液体在Friedel-crafts反应中的应用[J].天津化工,2006,20(2):9-11
[126]Seddon K R.Ionic Liquids for clean technology[J].Chem Teeh Biotechnol,1997,68(4):351-356.
[127]Xin H L,Wu Q,Han M H,et al.Alkylation of benezene with 1-dodecene in ionic liquids [Rmim]+Al_2Cl_6X(R=butyl,octyl and dodecyl;X=chlorine,bromine and iodine)[J].Applied Catalysis A:General,2005,292:354-361
[128]袁冰.沸石分子筛催化芳环化合物的Friedel-crafts酰基化反应的研究[D].大连理工大学,2006:80.
[129]Zhevenikov K.Catalysis by heteropoly acids and multicom ponent polyoxometalates in liquid —phase reactions[J].Chem Rev,1998,98(1):171-198
[130]杜少斌,徐元植.杂多酸及其盐的催化研究新进展[J].石油化工,1993,22:694-702
[131]Nishimura T,Okubara T,Misono M.High Catalytic Actibity of an insoluble acidic cesium salt of dodecatungstophosphoric acid for liquid-phase alkylation[J].Appl catal,1991,73(1):L7-L11
[132]赵振波,孙闻东,杨向光,等.用高浓度杂多酸溶液催化苯甲酸与乙酸酐的酰化反应[J].催化学报,2001,22(3):299-300
[133]Tagawa T,Amemiya J,Goto S,Chlorine-free Friedel-crafts acylation benzene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl Catal A:General,2004,257:19-23
[134]Firouzabadi H,Iranpoor N,Nowrouzi F.AIPW_(12)O_(40)as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-crafts acylation of aromatic compounds under solvent-less conditions[J].Tetrahedron letters,2004,60:10843-10850
[135]Tagawa T,Junichl A,Shigeo G.Chlorine-free Friedel-Crafts acylation of benezene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl.Catal.A:General,2004,257:19-23.
[136]袁新华,宗志敏,魏贤勇,等.芳香族化合物选择性烷基化的研究进展[J].现代化工,2000,20(5):17-22.
[137]徐寿昌著.有机化学[M].北京,高等教育出版社,1993:276
[138]袁新华,徐红星,伍林,等.主链型芳香族聚合物的研究进展[J].煤炭转化,2000,23(1):33-36
[139]Freemantle M.Designer solvents-ionic liquids may boost dean technology development[J].Chem Eng News,1998,76(12):32-37
[140]Qiao K,Deng Y Q.Alkylations of benzene in room temperature ionic liquids modified with HCI[J].Journal of Molecular Catalysis,2001,171:81-84
[141]AbdulSada A K,Atkins M P,Ellis B.Alkylation Process[P].US 1999,602:59-94
[142]Lzumi Y,Urabe K,Onaka M.Clay and heteropoly acid in organic reactions[M].Tokyo Kodansha/VCH,1991:99-161
[143]胡长文,高丽娟,王恩波等.钨系Keggin结构杂多酸的酸强度及催化反应特性[J].东北师范大学学报(自然辩学版),1995,2(2):62-70
[144]Carlos G B,Dolores C B,M.Dolores Gonz'alez Azp'lroz.Alkylation of naphthalene using three different ionic liquids[J].Journal of Molecular Catalysis A:2006,253:203-206
[145]李艳伟,白雪峰.氯铝酸盐离子液体催化β—甲基萘岐化反应[J].精细石油化工,2006,23(2):18-21.
[146]wartyn J E,Paul B,Kenneth R,et al.Regioselectice alkylation in ionic liquids[J].Chem.Commun,1998,20:2245-2246
[147]刘琪英,王军,武文良,等.硅胶负载的磷钨酸催化剂上萘的异丙基化反应[J].南京工业大学学报,2003,25(1):23-27
[148]于清跃,武文良,王军,等.萘与异丙醇γ-Al_2O_3负载的磷钨酸催化剂上烷基化[J].南京工业大学学报,2004,26(2):24-27
[149]陈双平,王寿武,汪守建,等.离子液体的性质和制备方法[J].精细化工中间体,2004, 4(5):10-12
[150]王鹏,高金森,王大喜,等.离子液体催化烷基化反应的研究进展[J].分子催化,2006,3(20):278-283
[151]胡焱,郭敏飞,韦萍,等.离子液体中烷基化反应研究进展[J].化学试剂,2006,28(2):79-82
[152]孙学文,赵锁奇,王仁安.[bmim]Cl/FeCl_3离子液体催化苯与乙烯烷基化的反应机理[J].催化学报,2004,25(3):247-251
[153]荣国斌译.波谱数据表—有机化合物的结构解析[M].上海,华东理工大学出版社,2002,180-182
[154]苏花平,李中华.酰基硫脲类硅烷偶联剂的合成[J].化学试剂,2005,27(4):237-238
[155]党国栋,周宏伟,杨薇,等.一类含联二萘结构的新型聚芳醚酮类刚性大环及其二聚体的合成与表征[J].高等学校化学学报,2005,26(1):166-169
[156]袁福根,丁春羊,居萍萍.3,5,3',5'-四叔丁基-苄烯-4,4'-醌的合成和分子结构[J].化学研究与应用,2005,18(2):202-203
[157]Hasegawa,Koichi;Yanai,Hiroshi;Miyazaki,Hiroshi;Furumoto,Masashi.Preparation of 5,5'-biacenaphthenyls[J].Jpn.Kokai Tokkyo Koho(1991).
[158]袁新华,徐红星,仰榴青.含α-活泼氢芳烃与硝基苯的反应及其机理研究[J].化学通报,2006,3:211-215
[159]姜鹏,吕士杰.用硅胶担载三氯化铁催化氧化偶联2-萘酚制备(±)2,2′-二羟基-1,1′-联萘[J].分子催化,2000,01:69-70
[160]陈继华.[bmim]Cl/FeCl_3离子液体的表征[J].化学工程师,2005,116(5):65-67.
[161]Li X,Keith E.Alkne cracking,alkene polymerization,and Friedel-Crafts alkylation in liquids containing the acidic anions HX_2~-,XH(AlX_4)~-,XH(Al_2X_7)~-,and Al_2X_7~-(X=chlorine,brornine)[J].Chemical,2004,214:121-127
[162]郑金云,冯祥明.氧化偶联共聚合制备主链含β-萘烷基醚的红色发光聚合物[J].化学研究,2006,17(3):39-43.
[163]韩维平.催化化学导论[M].北京,科学出版社,2003:240-269
[164]Kamavaram V,Mantha D,Reddy R G.Effect of process variables on current efficiency and deposit characteristics[J].Electrochimica Acta,2005,50:3286-3295
[2]孙永周.开展我国聚醚酮酮研究的建议[J].塑料工业,1990(2):25-29
[3]Song C S,Schobert H H.Prepri hydrogen-transferring pyrolysis of cyclic and straight-chain hydrocarbons[3].Am Chem Soc Div Fuel Chem Prepr,1992,37(2):524-532
[4]Scindvasan R,Farora M F.Polymerization of poly(Q-phenylenevinylene)and polyaniline.polymBull[J],1988,20:359-363
[5]Rose J B.Br P,1558671.1976
[6]张伟亚,张少文,吴采樱,等.杯芳烃衍生聚合物用作毛细管气相色谱固定相的研究[J].高等学校化学学报,1997,18(8):1296-1299
[7]Jaime C,Mendoza J D,Prados P,et al.~(13)C NMR chemical shifts:A single rule to determ ine the confo rmation of calix[4]arenes[J].J Org Chem,1991,56(10):3372-3376
[8]钟振林,李建森,卢雪然,等.逐步法合成杯[4]芳烃关环反应的改进[J].高等学校化学学报,1998,19(1):83-85
[9]Miller T M,Neenan T X.Ritic D.Analogues of engineering Plastics:A general one-step synthesis of dendritic polyaryl ethers[3].J Am Chem Soc,1993,115(1):356-357
[10]Miller T M,Neenan T X,Zayas R,et al.X,Zayas R et al.Synthesis and characterization of a series of monodisperse 1,3,5-phenlene-based hydrocarbon dendritic including C_(276)H_(186)and their Fluo rinated a nalogues[J].J Am Chem Soc,1992,114(3):1018-1025
[11]Moore J S.P Reparation of soluble starburst polymer with 127 benzalcyclics containing ethynylenzene unit angew[J].Chem,Int Ed Engl,1993,32:246-251
[12]Serrone S,Denti G,Gap istran S.Synthesis of denddrners containing 22 ruthenium ions and 22'-bipyddine on the surface angew[J].Chem Int Ed Engl,1992,31:1493-1499
[13]石高全,薛奇,金士.萘在三氟化硼乙醚溶液中的电化学聚合[J].高等学校化学学报,1993,14(11):1623-1624
[14]王长松,周本濂.可溶性聚吡咯复合导电薄膜的研制[J].高等学校化学学报,1999,20(2):315-317
[15]Jovanovic S V,Morris D G,Pliva C N.Laser flash photolysis of dinaphthyl ketones[J].Journal of photochemistry and photohiology.A:chemistry,1997,107(1):153-158
[16]魏贤勇,宗志敏,陈茺,等.面向21世纪的煤化工[J].华北地质矿产杂志,1996,11(1):1-8
[17]Pearson D E,Calvin A.Friedel-Crafts acylations with little or no catalyst[J].Synthesis,1972,55(8):533-542
[18]邓建元.芳酮聚合物[J].化工新型材料,1997,3:13-17
[19]胡文祥,恽榴红,张连锋.芳香稠环取代酰氯的合成[J].药学学报,1997,32(9):699-703
[20]李鸿州,高天星.光引发剂的发展概况[J].甘肃化工,2000,2:54.
[21]程其时,马永国.二苯甲酮类紫外吸收剂的发展趋势[J].中国塑料,1996,6:3-11
[22]Singn R P,Kamble R M,Chandra K L,et al.An efficient method for aromatic Friedel-crafts alkylation,acylation,benzoylation,and sulfonylation reactions[J].Tetrahedron,2001,57:241-247
[23]何志荣,张莉霞,朱凌皓.2,6—萘二甲酸及其酯的制备和应用[J].煤化工,2001(1):51-54
[24]王月梅,沈健.苯与长链烯烃烷基化反应催化剂的研究进展[J].广州化工,2004,32(4):4-6
[25]赵仁殿.芳烃工学[M].北京:化学工业出版社,1994,234
[26]徐克勋.精细有机化工原料及中间体[M].北京:化学工业出版社,2002
[27]梁锋,徐丙根,施小红,等.湿式氧化法脱硫的技术进展[J].现代化工,2003:21-24
[28]秦伟程.2-烷基蒽醌合成技术与应用市场[J].化工中间体,2004,1(1):10-17
[29]陆军民.苯乙酸生产方法综述[J].应用化工,2001,30(2):10-12
[30]张邦乐,何炜,张生勇.萘普生的催化不对称合成[J].1999,30(9):426-430
[31]舒歌平,陈鹏,杜淑凤.从煤焦油中制取2,6-二烷基萘的研究[J].煤炭转化,1997,20(3):13-18
[32]谢萍 陆道惠,黄琦,等.热致液晶聚合物-含萘环主成分为对羟基苯甲酸的全芳香族共聚酯[J].高分子通讯,1985,4:269-273
[33]林国强,陈耀全,陈新滋,等.手性合成-不对称反应及其应用[M].科学出版社,北京,2002:332
[34]李林涛,麻生明.以N-杂环卡宾为配体的金属络合物催化有机合成的反应[J].有机化学,2001,21(1):75-81
[35]Buhr C A,Matteucci M D,Froehler B C.Synthesis of a tetracyclic 2'-deoxyadenosine analog[J].Tetrahedron Lett,1999,40:8969-8970
[36]Olivera R,SanMartin R,Tellitu I,et al.The amine exchange/biaryl coupling sequence:a direct entry to the phenanthro[9,10-d]heterocyclic framework[J].Tetrahedron,2002,58:3021-3037
[37]Kang S K,Kim J S,Yoon S K,et al.Copper-catalyzed coupling of polymer bound iodide with organostannanes[J].Tetrahedron Letter,1998,39:3011-3012
[38]Pain C,Celanire S,Guillaumet G,et al.Synthesis of 5-substituted 2-(4-or 3-methoxyphenyl)-4(1H)-quinolones[J].Tetrahedron,2003,59:9627-9633
[39]Wang Q,Wol M,Polar T L,et al.Inhibition of neuraminidase with neuraminic acid C-glycosides[J].Chemistry Letters,2000,10:941-944
[40]Bryant H Y,Stephen L B.Palladium-catalyzed amination of aryl halides and sulfonates[J].Chemistry,1999,576:125-146
[41]Corma A,Garc'la H,Leyva A,et al.Alkali-exchanged sepiolites containing palladium as bifunctional(basic sites and noble metal)catalysts for the Heck and Suzuki reactions[J]. General,2004,257:77-83
[42]Bringmann G,Pfeifer R M,Schreiber P,et al.The 'Lactone Method':Enantioselective preparation of novel P,N-biaryl ligands and their use in the synthesis of the biarylic alkaloids,ancistrotanzanine B and ancistroealaine A[J].Tetrahedron,2004,60:4349-4360
[43]Corma A,Garc'la H,Leyva A,et al.Alkali-exchanged sepiolites containing palladium as bifunctional(basic sites and noble metal)catalysts for the Heck and Suzuki reactions[J].General,2004,257:77-83
[44]Bringmann G,Lang G,Michel M,et al.Stereochemical assignment of the fungal metabolite xestodecalactone A by total synthesis[J].Tetrahedron Letters,2004,45:2829-2831
[45]Abhishek S,Raj M,Raghunath V.Rate enhancement in palladium catalyzed Heck reactions by Lewis acid promoters[J].Catalysis Communications,2007,8:183-186
[46]Iyer S,Ramesh C,Sarkar A,etal.The vinylation of aryl and vinyl halides catalyzed by copper salts[J].Tetrahedron Letters,1997,38:8113-8116
[47]Annamaria C,Maria S,Marsich N,et al.Oxidative coupling of 2,6-dimethylphenol to polyphenylene ether catalyzed by a dinuclear Cu(Ⅱ)dihydroxo-diiodo complex of 2,2'-dipyridylamine[J].Chemical,1996,112:353-365
[48]Noji M,Nakajima M,Koga K.A new catalytic system for aerobic oxidative coupling of 2-naphthol derivatives by the use of CuCl-amine complex:A practical synthesis of binaphthol derivatives[J].Tetrahedron Lett,1994,35:7983-7984
[49]Iwata M,Maegawa T,Kita Y,et al.Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(Ⅲ)reagent[J].Tetrahedron Letter,2002,43:9241-9244
[50]Kodama S,Takita H,Kajimoto T,et al.Synthesis of amaryllidaceae alkaloids,aiculine,oxocrinine,epicrinine,and buflavine[J].Tetrahedron,2004,60:4901-4907
[51]Studer A,Bossart M,Vasella T,et al.Supported palladium catalysts for fine chemicals synthesis[J].Chemical,2001,173:3-18
[52]Escolano C,Jones K.Aryl Radical Cyclisation Onto Pyrroles:A divergent synthesis of spiropyrrolidinyloxindoles and pyrroloquinolines[J].Tetrahedron Letters,2000,41:8951-8955.
[53]Sugden S,Wilkins H.CLVXIL- the Preacher and Chemical Constitution Part Ⅶ:Fused metals and salts[J].Chem.Soc.,1929,7:1291-1293
[54]Chum H L,Koch V R,Miler L,et al.Electrochemical scrutiny of organmetallic iron complexes andhexmethlbenzene in a room temperature molten salt[J].J.Am.Chem.Soc,1975,97:3264-3270
[55]Wilkes J S,Zaworotko M J.Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids[J].J.Chem.Soc.Commun,1992,965-967
[56]赵忠奎,袁冰,李宗石,等.环境友好的离子液体及其在付-克反应中的应用[J].中国基础科学·科学前沿,2004,1:20-25
[57]张玉芬,乔聪震,张金昌,等.离子液体-环境友好的溶剂和催化剂[J].化学反应工程与工艺,2003,19(2):164-170
[58]张所波,于孟贤,高连勋.离子液体在有机反应中的应用[J].有机化学,2002,22(3):159-165
[59]Wikes J S,Mamantov G,Marassi R.Mathematical and physical sciences[J].D.Reichel Publishing Company,1987,202:405-416.
[60]Boon J A,Levisky J A,Pflug J L,et al.Friedel-Crafts reactions in ambient-temperature molten salts[J].J Org Chem,1986,51:480-483
[61]James R,Xiao J L.Friedel-Crafts acylation reactions using metal triflates in ionic liquid[J].Green chemistry,2002,4:129-133
[62]Rebeiro G L,Khadilkar B M.Microwave assisted aromatic nucleophilie substitution reaction under solventless condition[J].Synth.Commun,2003,33(8):1405
[63]Adama C J,Earle M J,Robertsq,et al,Friedel-Crafts Reactions in Room Temperature Ionic Liquids[J].Chem Common,1998,20:2097-2098
[64]Hao Z K,Li Z S,Wang G R,et al.Friedel-Crafts alkylation of 2-methylnaphthalene in room temperature ionic liquids[J].Appl.Catal.A-General,2004,262(1):69-73
[65]Qiao K,Yokoyama C.Novel acidic ionic liquids catalytic systems for Friedel-Crafts alkylation of aromatic compounds with alkenes[J].Chem.Lett.,2004,33(4):472-473
[66]Xiao L,Johnson K E,Treble R G.Alkane cracking,alkene polymerization,and Riedel-Crafts alkylation in liquids conraining the acidic anions HX_2~- XH(AlX4)`-,XH(AI_2X_7)~-,and Al_2X_7(X=chlorine,bromine)[J].J.Mol.Catal.A:Chem.,2004,214(1):121-127
[67]Freemantle M.Designer solvents-ionic liquids may boost clean technology development[J].Chem.Eng.News,1998,76(12):32-37
[68]Song C E,Shim W H,Roh E J,et al.Scandium(1I1)triflate immobilised in ionic liquids:A novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes[J].Chem.Commun.,2000,(17):1695-1696
[69]Qiao K,Deng Y Q.Alkylations of benzene in room temperature ionic liquids modified with HCI[J].Journal of Molecular Catalysis,2001,171:81-84
[70]Abdul-Sada A K,Atkins M P,Ellis B.Alkylation process[P].US 59-94602,1999
[71]Blanco C G,Banciella D C.Alkylation of naphthalene using three different ionic liquids[J].Journal of Molecular Catalysis A:253,2006,203-206
[72]李艳伟,白雪峰.氯铝酸盐离子液体催化β-甲基萘岐化反应[J].精细石油化工,2006,23(2):18-21
[73]Wartyn J E,Paul B.Regioselectice alkylation in ionic liquids[J].Chem.Commun,1998,20:2245-2246
[74]Ranu B C,Banerjee S.The dramatic influence of a task-specific ionic liquidI[bmIm]OH in michael addition of active methylene compounds to conjugated ketones,carboxylic esters,and nitriles[J].Organic Letters,2005,7(14):3049-3052
[75]Dere R,Pal R R,Patil P P.et al.Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction[J].Tetrahedron Lett,2003,44:5351-5353
[76]Pimenov A A,Makarova N V.Moiseev I K,et al.Reactions of CH acids with a.b-nsaturated ketones of the adamantare series[J].Russian Journal of Organic Chemistry,2001,31(12):1872-1873
[77]Lee C W.Diels-Alder reactions in chloroaluminate ionic liquids:acceleration and selectivity enhancement[J].Tetrahedron Lett,1999,40:2461-2464
[78]Meracz I,Taeboem Oh.Asymmetric Diels-Alder reactions in ionic liquids[J].Tetrahedron Letters,2003.(44):6465-6468
[79]Potdar K,Mohile S S,Salunkhe M M.Coumarin syntheses via pechmann condensation in Lewis acidic chloroaluminate ionic liquid[J].Tetrahadron letters,2001,42:9285-9287
[80]Harjani J R,Nara S J.Salunkhe.Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation[J].Tetrahadron Letters,2002,43:1127-1130
[81]Howarth J,James P,Ryan R.Sodium borohydride reduction of aldehydes and ketones in the recyclable ionic liquid[bmim]PF_6[J].Synth Commun,2001,31(19):2935-2942
[82]Chen W,Xu L,Chatterton C,et al.Palladium catalysed allylation reactions in ionic liquids[J].Chem Commun,1999(13):1247-1248
[83]Howarth,J.Oxidation of aromatic aldehydes in the ionic liquid[bmim]PFr[J].Tetrahedron Lett,2000,41:6627-6629
[84]Carmichael A J,Earle M J,Holbrey J D,et al.The Heck reaction in ionic liquids:A multiphasic catalyst system[J].Org.Lett,1999,1:997-1000
[85]Horvath I T,Rabai J.Facilec Catalyst separation with out water:Fluorous biphase hydyoformylation of olefins[J].Science,1994,266:72-74
[86]Kabalka G W,Malladi R R.Reduction of aldehydes using tdalkylboranes in ionic liquids[J].Chem.Commun.,2000,22:2191-2192
[87]Reynolds J L,Erdner K R,Jones P B.Photoreduction of benzophenones by amines in room temperature ionic liquids[J].Org.Lett,2002,4:917-919
[88]许林,郭军.杂多酸型催化剂的应用及其进展[J].石油化工,1994,23(7):477-481
[89]Kuroda Y,Kunai A,Hamada M,et al.J.Catalytic oxidation of naphthalene on palladium in cooperation with copper(Ⅰ)(Ⅱ)redox couple[J].Bull.Chem.Soc.Jpn.1991,64:3089-3093
[90]梁娟,王善均.催化剂新材料,北京:化学工业出版社,1990.79-86
[91]Kozhevnikov I V.Heteropoly acids and related compounds as catalysts for fine chemical synthesis[J].Catal.Rev.Sci.Eng.,1995,37(2):311-352
[92]Okuhara T,Mizuno N,Misono M.Advances in catalysis[C].London:Acdemic Press,1996,41:113-252
[93]王兴平,叶兴凯,吴越.活性炭表面固载十二硅钨酸地表征[J].催化学报,1995,16(6):510-513
[94]吴越,叶兴凯,杨向光,等.杂多酸的固载化—关于制备负载型酸催化剂的一般原理[J].分 子催化,1996,10(4):299-319
[95]Lzumi Y,Urabe K,Onaka M.et al.Clay and heteropoly acid in oraganic reactions[M].Kodnsha/VCH,Tokyo,1992:187-191
[96]赵振波,孙闻东,杨向光,等.用高浓度杂多酸溶液催化苯甲酸与乙酸酐的酰化反应[J].催化学报,2001,22(3):299-300
[97]Lzumi Y,Ogwa M,Nohara W,et al.Alkali metal salts andammonium salts of Keggin-type heteropolyacids as solid acid catalysts for liquid-phase Friedel-Crafts reactions[J].Appl Catal A:General1995,132:127-140
[98]Tagawa T,Amemiya J,Goto S.Chlorine-free Friedel-crafts acylation benzene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl Catal A:General 2004,257:19-23
[99]Firouzabadi H,Iranpoor N,Nowrouzi F.AlPW_(12)O_(40)as a non-hygroscopic Lewis acid catalyst for the efficient Fdedel-Crafts acylation of aromatic compounds under solvent-less conditions[J].Tetrahedron letters,2004,60:10843-10850
[100]Kaur J,Kozhevnikov I V.Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalysed by heteropoly salt Cs_(2.5)H_(0.5)[-PW12O40][J].Chem.commun,2002,18:2508-2509
[101]Tagawa T,Junichl A,Shlgeo G.Chlorine-free Fdedel-Crafts acylation of benezene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl.Catal.A:General,2004,257:19-23
[102]长谷部,连奥田,曲正.乙苯的制备方法[P].JP Patentt 525062,1993,02
[103]刘琪英,王军,武文良,等.硅胶负载的磷钨酸催化剂上萘的异丙基化反应[J].南京工业大学学报,2003,25(1):23-27.
[104]于清跃,武文良,王军等.萘与异丙醇γ-Al2O3负载的磷钨酸催化剂上烷基化[J].南京工业大学学报,2004,26(2):24-27.
[105]胡长文,高丽娟,王恩波,等.钨系Keggin结构杂多酸的酸强度及催化反应特性[J].东北师范大学学报(自然辩学版),1995,2(2):62-70
[106]秦玉楠.钼系杂多酸催化剂的结构、性能、制备和应用前景[J].中国钼业,2001,25(2):20-24
[107]Hou Z Y,Okuhara T,yoshioka H,et al.Catalytic synthesis of diphenylmethane from benzene and formalin with water-tolerant solid acids[J].Applied Catalysis A:General,2001,216:147-155.
[108]张敏.活性炭负载磷钨酸催化合成环己酮缩乙二醇[J].化学研究,2001,12(3):44-45
[109]迟洪盘,吴通好,李玉燕.杂多酸类催化剂的研究进展[J].齐鲁石油化工,1994,22(3):222-229
[110]Sato H,Nagai K,Yoshioka H.Vapor phase nitration of benzene over solid acid catalysts Ⅲ.Nitration with nitric acid(2);mixed metal oxide treated with sulfuric acid and heteropolyacid partially neutralized,Applied Catalysis A:General,1998,175:209-213
[111]Ono Y,Baba T.Selective reactions over solid base catalysts[J].Catalysis Today,1997,38:321-337
[112]陈景林,林青松,蒋山.气相硝化制备硝基苯的研究[J].分子催化,2001,15(2):119-123
[113]陈景林,林青松,吕连海,等.负载型磷钨酸催化苯气相硝化[J].石油化工,2001,30(1):1719
[114]许林,胡长文,王恩波.杂多酸型催化剂的研究进展[J].石油化工,1997,26(9):632-637
[115]许林,郭军.杂多酸型催化剂的研究进展[J].石油化工,1994,23(7):477-482
[116]Matveev K I,Odyakov V F,Zhizhiza E G.Heteropoly acids as oxidation catalysts in synthesis of K-vitamins[J].Journal of Molecular Catalysis A:Chemical,1996,114:151-160
[117]Jiang H S,Mao X,Xie X J,et al.Partially reduced heteropoly compound catalysts for the selective oxidation of propane[J].Journal of Molecular Catalysis A:Chemical,2000,185:143-149
[118]Futura M,Kung M C,Kung H H.One-step synthesis of ethyl acetate from ethene and oxygen[J].Applied Catalysis A:General,2000,201:L9-L11
[119]Jovanovic S V,Morris D G,Pliva C N.Laser flash photolysis of dinaphthyl ketones[J].Journal of photochemistry and photohiologyA:chemistry,1997,107(1):153-158
[120]李靖,廖祥军,刘华,等.3-溴丙基苯的傅克酰基化反应的研究[J].化学研究,1998,9(3):18-20
[121]Sommai P A,Kazumi O,Masahiro M.Acylation of 2-methoxynaphthalene with acyl chlorides in the presence of a catalytic amount of Lewis acids[J].Chem.Soc,1994,69(1):1703-1707
[122]王志萍,李露,于世涛,等.中孔分子筛Zr-Mo-MCM-41催化2-甲氧基萘傅克酰基化反应[J].青岛科技大学学报,2003,24(6):479-483
[123]Deutsch J,Prescott H A.Acylation of naphthalenes and anthracene on sulfated zirconia[J].Journal of catalysis,2005,231(2):269-278
[124]王葆仁.有机合成反应(下册)[M].北京:科学出版社,1985
[125]赵辉爽.离子液体在Friedel-crafts反应中的应用[J].天津化工,2006,20(2):9-11
[126]Seddon K R.Ionic Liquids for clean technology[J].Chem Teeh Biotechnol,1997,68(4):351-356.
[127]Xin H L,Wu Q,Han M H,et al.Alkylation of benezene with 1-dodecene in ionic liquids [Rmim]+Al_2Cl_6X(R=butyl,octyl and dodecyl;X=chlorine,bromine and iodine)[J].Applied Catalysis A:General,2005,292:354-361
[128]袁冰.沸石分子筛催化芳环化合物的Friedel-crafts酰基化反应的研究[D].大连理工大学,2006:80.
[129]Zhevenikov K.Catalysis by heteropoly acids and multicom ponent polyoxometalates in liquid —phase reactions[J].Chem Rev,1998,98(1):171-198
[130]杜少斌,徐元植.杂多酸及其盐的催化研究新进展[J].石油化工,1993,22:694-702
[131]Nishimura T,Okubara T,Misono M.High Catalytic Actibity of an insoluble acidic cesium salt of dodecatungstophosphoric acid for liquid-phase alkylation[J].Appl catal,1991,73(1):L7-L11
[132]赵振波,孙闻东,杨向光,等.用高浓度杂多酸溶液催化苯甲酸与乙酸酐的酰化反应[J].催化学报,2001,22(3):299-300
[133]Tagawa T,Amemiya J,Goto S,Chlorine-free Friedel-crafts acylation benzene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl Catal A:General,2004,257:19-23
[134]Firouzabadi H,Iranpoor N,Nowrouzi F.AIPW_(12)O_(40)as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-crafts acylation of aromatic compounds under solvent-less conditions[J].Tetrahedron letters,2004,60:10843-10850
[135]Tagawa T,Junichl A,Shigeo G.Chlorine-free Friedel-Crafts acylation of benezene with benzoic anhydride on insoluble heteropoly acid catalyst[J].Appl.Catal.A:General,2004,257:19-23.
[136]袁新华,宗志敏,魏贤勇,等.芳香族化合物选择性烷基化的研究进展[J].现代化工,2000,20(5):17-22.
[137]徐寿昌著.有机化学[M].北京,高等教育出版社,1993:276
[138]袁新华,徐红星,伍林,等.主链型芳香族聚合物的研究进展[J].煤炭转化,2000,23(1):33-36
[139]Freemantle M.Designer solvents-ionic liquids may boost dean technology development[J].Chem Eng News,1998,76(12):32-37
[140]Qiao K,Deng Y Q.Alkylations of benzene in room temperature ionic liquids modified with HCI[J].Journal of Molecular Catalysis,2001,171:81-84
[141]AbdulSada A K,Atkins M P,Ellis B.Alkylation Process[P].US 1999,602:59-94
[142]Lzumi Y,Urabe K,Onaka M.Clay and heteropoly acid in organic reactions[M].Tokyo Kodansha/VCH,1991:99-161
[143]胡长文,高丽娟,王恩波等.钨系Keggin结构杂多酸的酸强度及催化反应特性[J].东北师范大学学报(自然辩学版),1995,2(2):62-70
[144]Carlos G B,Dolores C B,M.Dolores Gonz'alez Azp'lroz.Alkylation of naphthalene using three different ionic liquids[J].Journal of Molecular Catalysis A:2006,253:203-206
[145]李艳伟,白雪峰.氯铝酸盐离子液体催化β—甲基萘岐化反应[J].精细石油化工,2006,23(2):18-21.
[146]wartyn J E,Paul B,Kenneth R,et al.Regioselectice alkylation in ionic liquids[J].Chem.Commun,1998,20:2245-2246
[147]刘琪英,王军,武文良,等.硅胶负载的磷钨酸催化剂上萘的异丙基化反应[J].南京工业大学学报,2003,25(1):23-27
[148]于清跃,武文良,王军,等.萘与异丙醇γ-Al_2O_3负载的磷钨酸催化剂上烷基化[J].南京工业大学学报,2004,26(2):24-27
[149]陈双平,王寿武,汪守建,等.离子液体的性质和制备方法[J].精细化工中间体,2004, 4(5):10-12
[150]王鹏,高金森,王大喜,等.离子液体催化烷基化反应的研究进展[J].分子催化,2006,3(20):278-283
[151]胡焱,郭敏飞,韦萍,等.离子液体中烷基化反应研究进展[J].化学试剂,2006,28(2):79-82
[152]孙学文,赵锁奇,王仁安.[bmim]Cl/FeCl_3离子液体催化苯与乙烯烷基化的反应机理[J].催化学报,2004,25(3):247-251
[153]荣国斌译.波谱数据表—有机化合物的结构解析[M].上海,华东理工大学出版社,2002,180-182
[154]苏花平,李中华.酰基硫脲类硅烷偶联剂的合成[J].化学试剂,2005,27(4):237-238
[155]党国栋,周宏伟,杨薇,等.一类含联二萘结构的新型聚芳醚酮类刚性大环及其二聚体的合成与表征[J].高等学校化学学报,2005,26(1):166-169
[156]袁福根,丁春羊,居萍萍.3,5,3',5'-四叔丁基-苄烯-4,4'-醌的合成和分子结构[J].化学研究与应用,2005,18(2):202-203
[157]Hasegawa,Koichi;Yanai,Hiroshi;Miyazaki,Hiroshi;Furumoto,Masashi.Preparation of 5,5'-biacenaphthenyls[J].Jpn.Kokai Tokkyo Koho(1991).
[158]袁新华,徐红星,仰榴青.含α-活泼氢芳烃与硝基苯的反应及其机理研究[J].化学通报,2006,3:211-215
[159]姜鹏,吕士杰.用硅胶担载三氯化铁催化氧化偶联2-萘酚制备(±)2,2′-二羟基-1,1′-联萘[J].分子催化,2000,01:69-70
[160]陈继华.[bmim]Cl/FeCl_3离子液体的表征[J].化学工程师,2005,116(5):65-67.
[161]Li X,Keith E.Alkne cracking,alkene polymerization,and Friedel-Crafts alkylation in liquids containing the acidic anions HX_2~-,XH(AlX_4)~-,XH(Al_2X_7)~-,and Al_2X_7~-(X=chlorine,brornine)[J].Chemical,2004,214:121-127
[162]郑金云,冯祥明.氧化偶联共聚合制备主链含β-萘烷基醚的红色发光聚合物[J].化学研究,2006,17(3):39-43.
[163]韩维平.催化化学导论[M].北京,科学出版社,2003:240-269
[164]Kamavaram V,Mantha D,Reddy R G.Effect of process variables on current efficiency and deposit characteristics[J].Electrochimica Acta,2005,50:3286-3295