以双酚化合物及对卤苯酚为起始原料,经用苄基保护、乌尔曼成醚、选择性硝化和还原脱保护4步反应,合成了具有双酚芳香醚结构的4个新型聚苯并(口恶)唑单体:双(3-氨基-4-羟基苯基)双酚醚类化合物的盐酸盐.确定了乌尔曼成醚反应的最佳工艺条件,证明硝化反应只发生在对卤苯酚苄保护基的邻位,改进了还原脱保护反应的成盐及后处理条件,提高了产物的质量和收率,4步反应总收率可达54.0％.采用红外光谱、核磁共振H谱和高分辨质谱表征了每步产物的化学结构.
参考文献
| [1] | Wolfe J F,Arnold F E.Rigid-rod Polymers:1.Synthesis and Thermal Properties of Para-aromatic Polymers with 2,6-Benzobisoxazole Units in the Main Chain[J].Macromolecules,1981,14(4):909-915. |
| [2] | Wang L,Huang Y D,Liu L,et al.The Influence of PBO Coating on Room Temperature Mechanic Properties of Heat-treated Quartz Fiber-reinforced Methyl Silicon Resin Composites:Ⅰ.Flexural Properties[J].Mater Sci Eng,2007,465A(1):22-28. |
| [3] | Zylon Department Toyobo Co.,Ltd.PBO Fiber-ZYLON[R].Toyobo Co.,Ltd,Annual Report,2000:14-17. |
| [4] | Scapa Group.Plc.Improved Industrial Fabrics:WO,9918282[P],1999-04-15. |
| [5] | Mcghee J M.PBO Reinforced Sails and Sailcloth:EP,0885803[P],1998-12-23. |
| [6] | Yamanaka A,Kashima T.Turntable for Polishing:JP,A,11-114812[P],1999-04-27. |
| [7] | Suefuji R,Yamamoto Y.Adhesion of Polyparaphenylenebenzo-bis-oxazole Fiber to Chloroprene Rubber:JP,A,11-12370[P],1999-01-19. |
| [8] | Mader E,Melcher S,Liu J W,et al.Adhesion of PBO Fiber in Epoxy Composites[J].J Mater Sci,2007,42(19):8047-8052. |
| [9] | FANG Jianhua,GUO Xiaoxia.Bisaminophenols and Synthetic Processes of the Bisaminophenols:CN,1660776[P],2005-08-13(in Chinese).房建华,郭晓霞.芳香二氨基二羟基化合物及其制备方法:中国,1660776[P],2005-08-13. |
| [10] | YANG Shiyong,TAO Liming.Fluorine-containing Bis-o-hydroxyamino Aromatic Compounds and Its Preparation Method and Application:CN,101362700[P],2009-02-11 (in Chinese).杨士勇,陶立明.双邻羟基含氟芳香族二胺化合物及其制备方法与应用:中国,101362700[P],2009-02-11. |
| [11] | JIAN Xigao,CHEN Ping.Sytheses and Properties of Novel High Performance Series Poly (aromatic ethers) Polymers Containing Phthalazinone Moieties[J].Acta Polym Sin,2003,4:469-475 (in Chinese).蹇锡高,陈平.含二氮杂荼酮结构新型聚芳醚系列高性能聚合物的合成与性能[J].高分子学报,2003,4:469-475. |
| [12] | LIU Baijun,CHEN Cunhai.Synthesis and Characterization of Novel Fluorine-containing Poly(aryl ether ketone)s[J].Chem J Chinese Univ,2002,23(2):321-323(in Chinese).刘佰军,陈春海.新型含氟聚芳醚酮的合成与表征[J].高等学校化学学报,2002,23(2):321-323. |
| [13] | ZHAO Xiaogang,JI Kejian.Synthesis and Characterization of Poly(Aryl Ether Ketone) Containing Bisphenol A[J].Polym Mater Sci Eng,2011,27(5):29-31 (in Chinese).赵晓刚,冀克俭.双酚A型聚芳醚酮的合成与表征[J].高分子材料科学与工程,2011,27(5):29-31. |
| [14] | Walter A,Gnüchtel I,Maltenberger A,et al.Bis-o-aminophenols and Processes for Producing Bis-o-aminophenols:US,6861560[P],2005-03-01. |
| [15] | Calle M,Chan Y,Jo H J,et al.The Relationship Between the Chemical Structure and Thermal Conversion Temperatures of Thermally Rearranged(TR) Polymers[J].Polymer,2012,53(13):2783-2791. |
| [16] | Chen Y J,Chen H H.1,1,1-Tris(hydroxymethyl) ethane as a New,Efficient,and Versatile Tripod Ligand for CopperCatalyzed Cross-Coupling Reactions of Aryl Iodides with Amides,Thiols,and Phenols[J].Org Lett,2006,24(8):5609-5612. |
| [17] | Tananka E,Fujimoto M.Process for Producting Bis (4-hydroxy-3-nitrophenyl) Compound:US,6608233[P],2003-08-19. |
| [18] | ZHAO Zhizhong.Protecting Groups in Organic Chemistry[M].Beijing:Science Press,1984:155-156 (in Chinese).赵知中.有机化学中的保护基团[M].北京:科学出版社,1984:155-156. |
| [19] | Cristau H J,Cellier P P,Hamada S,et al.A General and Mild Ullmann-Type Synthesis of Diaryl Ethers[J].Org Lett,2004,6(6):913-916. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%