新型铝配合物的合成及CO_2/环氧丙烷环加成反应
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摘要
采用3,5-二叔丁基水杨醛和2-氨基苯酚合成了水杨醛亚胺双酚配体,该配体同氯化二乙基铝在惰性气氛下进行反应,成功地制备了水杨醛亚胺铝配合物并用核磁共振对其结构进行了表征。合成的铝配合物与四丁基溴化铵(TBAB)组成的双组分催化剂,可以催化二氧化碳和环氧丙烷环加成反应,并且对环加成产物碳酸丙烯酯表现出高选择性。在n(环氧丙烷)/n(催化剂)=1000/1,[铝配合物]/[TBAB]=1/20,反应温度为80℃,二氧化碳压力为2 MPa时,10 h内环氧丙烷的转化率可以高达91.2%,环加成产物碳酸丙烯酯选择性大于99%,未发现聚合物生成。
A new aluminum complex supported by tridentate bisphenolate ligand was synthesized from diethylaluminum chloride with salicylimine bisphenol proligand,and it was structurally characterized by NMR technique. The bicomponent catalyst of resultant aluminum complex and tetrabutylammonium bromide(TBAB) displayed medium activity toward the cycloaddition of carbon dioxide and propylene oxide, and it also displayed exclusive selectivity towards cycloaddition product propylene carbonate. 91.2% of propylene oxide was exclusively converted to the cyclic carbonate product in 10 h at 80 ℃ in the presence of CO_2(2 MPa) with aluminum complex-to-TBAB under the molar ratio of 1/20 in neat propylene oxide. No polymeric products were discovered in the reaction mixture.
A new aluminum complex supported by tridentate bisphenolate ligand was synthesized from diethylaluminum chloride with salicylimine bisphenol proligand,and it was structurally characterized by NMR technique. The bicomponent catalyst of resultant aluminum complex and tetrabutylammonium bromide(TBAB) displayed medium activity toward the cycloaddition of carbon dioxide and propylene oxide, and it also displayed exclusive selectivity towards cycloaddition product propylene carbonate. 91.2% of propylene oxide was exclusively converted to the cyclic carbonate product in 10 h at 80 ℃ in the presence of CO_2(2 MPa) with aluminum complex-to-TBAB under the molar ratio of 1/20 in neat propylene oxide. No polymeric products were discovered in the reaction mixture.
引文
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[55]Rongchang Luo,Xiantai Zhou,Shaoyun Chen,Yang Li,Lei Zhou and Hongbing Ji.Green Chem.,2014,16:1496-1506.
[56]Jaisiel Mele′ndez,Michael North and Pedro Villuendas,Chem.Commun.,2009:2577-2579.
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[58]Yanwei Ren,Ou Jiang,Hang Zeng,Qiuping Mao and Huanfeng Jiang.RSC Adv.,2016,6:3243-3249.
[59]Dawei Tian,Binyuan Liu,Li Zhang,Xiaoyang Wang,Wei Zhang,Lina Han,Dae-Won Park.Journal of Industrial and Engineering Chemistry,2012,18:1332-1338.
[60]Tadashi Ema,Yuki Miyazaki,Junta Shimonishi,Chihiro Maeda,and Jun-ya Hasegawa.J.Am.Chem.Soc.,2014,136:15270-15279.
[61]Wei-Min Ren,Ye Liu,and Xiao-Bing Lu,J.Org.Chem.,2014,79:9771-9777.
[62]Michael North and Carl Young,Catal.Sci.Technol.,2011,1:93-99.
[63]Felipe de la Cruz-Martínez,Javier Martínez,Miguel A.Gaona,Juan Ferna?ndez-Baeza,Luis F.Sa?nchez-Barba,Ana M.Rodríguez,Jose?A.Castro-Osma,Antonio Otero,and Agustín Lara-Sa?nchez.ACSSustainable Chem.Eng.2018,6:5322-5332.
[64]Martínez J,de la Cruz-Martínez F,Gaona M A,et al.Influence of the Counterion on the Synthesis of Cyclic Carbonates Catalyzed by Bifunctional Aluminum Complexes[J].Inorganic chemistry,2019,58:3398-3406.
[65]Javier Martínez,JoséA.Castro-Osma,Carlos Alonso-Moreno,Antonio Rodríguez-Diéguez,Michael North,Antonio Otero,Agustín Lara-Sánchez.ChemSusChem 2017,10:1175-1185.
[66]Sumrit P,Chuawong P,Nanok T,et al.Aluminum complexes containing salicylbenzoxazole ligands and their application in the ring-opening polymerization of rac-lactide andε-caprolactone[J].Dalton Transactions,2016,45(22):9250-9266.
[67]North M,Pasquale R.Mechanism of cyclic carbonate synthesis from epoxides and CO2[J].Angewandte Chemie,2009,121(16):2990-2992.
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