Peroxidase-catalyzed oxidative polymerization of 4,4′-dihydroxydiphenyl ether.: Formation of α,ω-hydroxyoligo(1,4-phenylene oxide) through an unusual reaction pathway

被引:32
作者
Fukuoka, T
Tonami, H
Maruichi, N
Uyama, H
Kobayashi, S [1 ]
Higashimura, H
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan
[2] Japan Chem Innovat Inst, Joint Res Ctr Precis Polymerizat, NIMC, Tsukuba, Ibaraki 3058565, Japan
关键词
D O I
10.1021/ma001054w
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Peroxidase-catalyzed oxidative polymerization of 4,4′-dihydroxydiphenyl ether was demonstrated in an aqueous solution. This reaction led to the formation of α,ω-hydroxyoligo(1,4-phenylene oxide)s in moderate yields. Hydroquinone was also one of the products during the reaction. The corresponding data suggested that redistribution and/or rearrangement of the quinone-ketal intermediate took place to produce the oligomers and hydroquinone.
引用
收藏
页码:9152 / 9155
页数:4
相关论文
共 34 条
[1]   SYNTHESIS AND CHARACTERIZATION OF POLYMERS PRODUCED BY HORSERADISH-PEROXIDASE IN DIOXANE [J].
AKKARA, JA ;
SENECAL, KJ ;
KAPLAN, DL .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1991, 29 (11) :1561-1574
[2]  
Aycock D., 1986, ENCY POLYM SCI ENG, V13, P1
[3]   Ab initio calculations on 2,6-dimethylphenol and 4-(2,6-dimethylphenoxy)-2,6-dimethylphenol.: Evidence of an important role for the phenoxonium cation in the copper-catalyzed oxidative phenol coupling reaction [J].
Baesjou, PJ ;
Driessen, WL ;
Challa, G ;
Reedijk, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12590-12594
[4]   POLYMERIZATION OF PHENOLS CATALYZED BY PEROXIDASE IN NONAQUEOUS MEDIA [J].
DORDICK, JS ;
MARLETTA, MA ;
KLIBANOV, AM .
BIOTECHNOLOGY AND BIOENGINEERING, 1987, 30 (01) :31-36
[5]   Biodegradation of polyaromatics synthesized by peroxidase-catalyzed free-radical polymerization [J].
Farrell, R ;
Ayyagari, M ;
Akkara, J ;
Kaplan, D .
JOURNAL OF ENVIRONMENTAL POLYMER DEGRADATION, 1998, 6 (03) :115-120
[6]  
Gross R. A., 1998, ACS SYM SER, P684
[7]  
Hay AS, 1998, J POLYM SCI POL CHEM, V36, P505, DOI 10.1002/(SICI)1099-0518(199803)36:4<505::AID-POLA1>3.3.CO
[8]  
2-C
[9]   Highly regioselective oxidative polymerization of 4-phenoxyphenol to poly(1,4-phenylene oxide) catalyzed by tyrosinase model complexes [J].
Higashimura, H ;
Fujisawa, K ;
Moro-oka, Y ;
Kubota, M ;
Shiga, A ;
Terahara, A ;
Uyama, H ;
Kobayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8529-8530
[10]   Radical-controlled oxidative polymerization of 4-phenoxyphenol by a tyrosinase model complex catalyst to poly(1,4-phenylene oxide) [J].
Higashimura, H ;
Kubota, M ;
Shiga, A ;
Fujisawa, K ;
Moro-oka, Y ;
Uyama, H ;
Kobayashi, S .
MACROMOLECULES, 2000, 33 (06) :1986-1995