Radical synthesis of tetrameric lignin model compound

被引：8

作者：

Ouyang, Xin-Ping ^{[1
]}

Yang, Yun ^{[1
]}

Zhu, Guo-Dian ^{[1
]}

Qiu, Xue-Qing ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2015年 / 26卷 / 08期

基金：

国家自然科学基金重大项目;

关键词：

Lignin; Model compound; Tetramer; Radical synthesis; OXIDATION;

D O I：

10.1016/j.cclet.2015.05.011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The lack of suitable lignin model compound limits the understanding of the characteristics of lignin, and hence hinders the efficient utilization of this kind of bioresource. A tetramer phenolic lignin model compound composed of 5-5, alpha-O-4 and beta-5 linkages was prepared by a two-step of free radical reaction with hydrogen peroxide/horseradish peroxidase and S2O82-/Fe2+ as the initiator. Compared with enzymatic process, this synthetic process gives a higher yield of 33.8% within a shorter time. HRMS and C-13 NMR spectroscopy show that synthesized model compound contains phenylpropane structure linked by 5-5, alpha-O-4 and beta-5 bonds, which can mimic some chemical characteristics of lignin. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：980 / 982

页数：3

共 10 条

[1]

Alves VL, 2000, J BRAZIL CHEM SOC, V11, P467

[2] The pyrolysis chemistry of a β-O-4 type oligomeric lignin model compound [J].

Chu, Sheng ;

Subrahmanyam, Ayyagari V. ;

Huber, George W. .

GREEN CHEMISTRY, 2013, 15 (01) :125-136

[3]

Dasari MS, 2008, J CHEM EDUC, V85, P411

[4] An efficient and flexible synthesis of model lignin oligomers [J].

Forsythe, W. Graham ;

Garrett, Mark D. ;

Hardacre, Christopher ;

Nieuwenhuyzen, Mark ;

Sheldrake, Gary N. .

GREEN CHEMISTRY, 2013, 15 (11) :3031-3038

[5] SYNTHESIS OF HEXAMERIC LIGNIN MODEL COMPOUNDS [J].

KILPELAINEN, I ;

TERVILAWILO, A ;

PERAKYLA, H ;

MATIKAINEN, J ;

BRUNOW, G .

HOLZFORSCHUNG, 1994, 48 (05) :381-386

[6] Persulfate oxidation for in situ remediation of TCE. I. Activated by ferrous ion with and without a persulfate-thiosulfate redox couple [J].

Liang, CJ ;

Bruell, CJ ;

Marley, MC ;

Sperry, KL .

CHEMOSPHERE, 2004, 55 (09) :1213-1223

[7] Simple preparation of 8-5-coupled diferulate [J].

Ralph, J ;

Conesa, MTG ;

Williamson, G .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (07) :2531-2532

[8] Oxidation of isoeugenol and coniferyl alcohol catalyzed by laccases isolated from Rhus vernicifera Stokes and Pycnoporus coccineus [J].

Shiba, T ;

Xiao, L ;

Miyakoshi, T ;

Chen, CL .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 10 (06) :605-615

[9] Hydrogenolysis of β-O-4 lignin model dimers by a ruthenium-xantphos catalyst [J].

Wu, Adam ;

Patrick, Brian O. ;

Chung, Enoch ;

James, Brian R. .

DALTON TRANSACTIONS, 2012, 41 (36) :11093-11106

[10] The synthesis and chemical structures of tetrameric lignin model compounds [J].

Xi, F ;

Reeve, DW ;

McKague, AB .

JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 1996, 16 (01) :35-46

← 1 →