Understanding and Suppression of Side Reaction during Transesterification of Phenolic Hydroxyl Groups of Lignin with Vinyl Ester

被引：5

作者：

Suzuki, Shiori ^{[1
,2
]}

Ishikuro, Akinari ^{[2
]}

Hamano, Yosuke ^{[2
]}

Hirose, Daisuke ^{[2
]}

Wada, Naoki ^{[2
]}

Takahashi, Kenji ^{[2
]}

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Biomat Sci, Bunkyo Ku, 1-1-1 Yayoi, Tokyo 1138657, Japan

[2] Kanazawa Univ, Fac Nat Syst, Inst Sci & Engn, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

来源：

CHEMISTRY LETTERS | 2020年 / 49卷 / 08期

基金：

日本科学技术振兴机构;

关键词：

Transesterification; Lignin; Ionic liquids; IONIC LIQUIDS; CATALYTIC-ACTIVITY; MIXED ANHYDRIDE; CELLULOSE; ESTERIFICATION; ACETYLATION; DISSOLUTION; INSIGHT;

D O I：

10.1246/cl.200202

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic transesterification reaction on phenolic hydroxyl groups by a carboxylate-type ionic liquid, 1-ethyl-3-methylimidazolium p-anisate ([Emim][OAn]), was investigated using a model reaction with phenol and vinyl propionate. Undesirable contamination of the ester group formed on the phenol with an acyl group derived from the acyl anion in the [Emim] [OAn] was effectively suppressed. This catalytic reaction was applied to Kraft lignin, and the desired esterification was successfully promoted on the hydroxyl groups with a conversion of up to 94 mol %.

引用

页码：900 / 904

页数：5

共 50 条

[41] IODINE-CATALYZED FERRIER REACTION .1. A MILD AND HIGHLY VERSATILE GLYCOSYLATION OF HYDROXYL AND PHENOLIC GROUPS
KOREEDA, M
HOUSTON, TA
SHULL, BK
KLEMKE, E
TUINMAN, RJ
SYNLETT, 1995, (01) : 90 - 92
[42] XYLOSYLATION OF PHENOLIC HYDROXYL-GROUPS OF THE MONOMERIC LIGNIN MODEL COMPOUNDS 4-METHYLGUAIACOL AND VANILLYL ALCOHOL BY CORIOLUS-VERSICOLOR
KONDO, R
YAMAGAMI, H
SAKAI, K
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1993, 59 (02) : 438 - 441
[43] Ab initio studies on the molecular conformation of lignin model compounds I.: Conformational preferences of the phenolic hydroxyl and methoxy groups in guaiacol
Agache, C
Popa, VI
MONATSHEFTE FUR CHEMIE, 2006, 137 (01): : 55 - 68
[44] Ab Initio Studies on the Molecular Conformation of Lignin Model Compounds I. Conformational Preferences of the Phenolic Hydroxyl and Methoxy Groups in Guaiacol
Costel Agache
Valentin I. Popa
Monatshefte für Chemie / Chemical Monthly, 2006, 137 : 55 - 68
[45] REACTIONS OF TRIFLUOROACETIC ACID WITH POLY(VINYL ALCOHOL) AND ITS MODEL COMPOUNDS . EFFECT OF NEIGHBORING HYDROXYL GROUPS ON REACTION
FUJII, K
BROWNSTE.S
EASTHAM, AM
JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1968, 6 (8PA1): : 2377 - &
[46] Horseradish peroxidase-catalyzed formation of hydrogels from chitosan and poly(vinyl alcohol) derivatives both possessing phenolic hydroxyl groups
Sakai, Shinji
Khanmohammadi, Mehdi
Khoshfetrat, Ali Baradar
Taya, Masahito
CARBOHYDRATE POLYMERS, 2014, 111 : 404 - 409
[47] Synthesis and hole-transporting properties of vinyl-type polynorbornenes with ethyl ester linked triarylamine side groups
Park, Myung Hwan
Yun, Changhun
Huh, Jung Oh
Do, Youngkyu
Yoo, Seunghyup
Lee, Min Hyung
SYNTHETIC METALS, 2010, 160 (17-18) : 2000 - 2007
[48] One-pot strategy to access dynamic dual network from lignin-initiated star polymers by side reaction and transesterification
Yan, Quan
Xue, Bailiang
Zhang, Tonghe
Wang, Wenliang
Li, Xinping
Shen, Xiaojun
Ning, Lulu
Meng, Xianzhi
Zhao, Wei
POLYMER CHEMISTRY, 2024, 15 (30) : 3052 - 3062
[49] REACTIVE CARBON-BLACK HAVING ACTIVE PHENYL ESTER GROUPS - PREPARATION AND REACTION WITH FUNCTIONAL POLYMERS HAVING HYDROXYL OR AMINO-GROUPS
TSUBOKAWA, N
HOSOYA, M
REACTIVE POLYMERS, 1991, 14 (02): : 95 - 102
[50] High-purity lignin fractions and nanospheres rich in phenolic hydroxyl and carboxyl groups isolated with alkaline deep eutectic solvent from wheat straw
Yue, Xin
Suopajarvi, Terhi
Sun, Shirong
Mankinen, Otto
Mikkelson, Atte
Huttunen, Harri
Komulainen, Sanna
Romakkaniemi, Idamaria
Ahola, Juha
Telkki, Ville-Veikko
Liimatainen, Henrikki
BIORESOURCE TECHNOLOGY, 2022, 360

← 1 2 3 4 5 →