Synthesis of Bis(3-amino-4-hydroxyphenyl) Bisphenol Ether

doi:10.3724/SP.J.1095.2013.20501

Chinese Journal of Applied Chemistry

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Synthesis of Bis(3-amino-4-hydroxyphenyl) Bisphenol Ether

ZHANG Qianfeng¹, TANG Anbin^1,2*, HUANG Jie², MA Hanbing¹, YANG Yuchuan²

(1.School of Materials Science and Engineering,Southwest University of Science and Technology,Mianyang 621010,China;
2.Sichuan EM Technology Co.,Ltd,National Insulating Material Engineering Research Center,Mianyang 621000,China)

Received:2012-11-05 Revised:2013-02-07 Published:2013-09-10 Online:2013-09-10

Abstract

Abstract: Four monomers of polybenzoxazole having the structure of bisphenol aromatic ether, bis(3-amino-4-hydroxyphenyl) bisphenol ether, were prepared from bisphenols and 4-chloro(or bromo)-phenol by successive 4 steps of synthetic routes including benzyl protection, Ullmann reaction, selective nitrification and reduction-deprotection. The effect of reaction conditions on the Ullmann reaction was investigated. The high region selection of the nitrification is confirmed. The process of after-treatment of the reduction-deprotection was optimized and the quality and yield of the product were improved. The total yield of 4 steps reaction can reach up to 54.0%. The target compound and its intermediates were characterized by means of IR, 1H NMR and HRMS.

Key words: monomer of polybenzoxazole, Ullmann reaction, bis(aminohydroxyphenyl) bisphenol ether, synthesis

CLC Number:

O625

ZHANG Qianfeng1, TANG Anbin1,2*, HUANG Jie2, MA Hanbing1, YANG Yuchuan2. Synthesis of Bis(3-amino-4-hydroxyphenyl) Bisphenol Ether[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20501.

References

[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 Copper-Catalyzed 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.

Synthesis of Bis(3-amino-4-hydroxyphenyl) Bisphenol Ether

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