Protection Strategies for the Conversion of Biobased Furanics to Chemical Building Blocks

被引:20
作者
Coumans, Ferdy J. A. G. [1 ]
Overchenko, Zhanna [1 ]
Wiesfeld, Jan J. [2 ]
Kosinov, Nikolay [1 ]
Nakajima, Kiyotaka [2 ]
Hensen, Emiel J. M. [1 ]
机构
[1] Eindhoven Univ Technol, Lab Inorgan Chem & Catalysis, NL-5600 MB Eindhoven, Netherlands
[2] Hokkaido Univ, Inst Catalysis, Sapporo, Hokkaido 0010021, Japan
基金
日本学术振兴会;
关键词
Biomass; Chemical building blocks; Furanics; Humins; Side reactions; Protection; DIELS-ALDER REACTIONS; MOLECULAR-STRUCTURE; BIOMASS CONVERSION; ACID; HUMINS; CATALYSTS; PLATFORM; OXIDATION; HMF; ETHERIFICATION;
D O I
10.1021/acssuschemeng.1c06723
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In recent years, the urgency to replace fossil-based resources by renewablebiomass for obtaining chemical building blocks has only increased. Carbohydrate-derivedfuranic compounds are regarded as promising platforms for a renewable value chain. Thehigh reactivity of such biobased intermediates requires the development of novel catalyticchemistry to enhance product yield. The protection of reactive functional groupsprovides a way to improve the product selectivity. Such protection strategies are commonpractice in the synthesis offine chemicals and pharmaceuticals but are not fully exploredfor the conversion of furanic compounds. In this perspective, several examples ofprotection strategies focusing on the selective passivation of 5-HMF are discussed.Formation and removal of these protection groups are highlighted as well as theapplication of the neutralized 5-HMF in further processing. A guide for selecting theappropriate protection strategy depending on the targeted chemistry and operatingconditions is provided.
引用
收藏
页码:3116 / 3130
页数:15
相关论文
共 85 条
[11]   SYNTHESIS OF FURAN-2,5-DICARBALDEHYDE BY OXIDATION OF 5-SILYLOXYMETHYL-2-FURFURAL [J].
COTTIER, L ;
DESCOTES, G ;
LEWKOWSKI, J .
SYNTHETIC COMMUNICATIONS, 1994, 24 (07) :939-944
[12]   Selective deprotection of silyl ethers [J].
Crouch, R. David .
TETRAHEDRON, 2013, 69 (11) :2383-2417
[13]   Efficient Continuous Production of the Biofuel Additive 5-(t-Butoxymethyl) Furfural from 5-Hydroxymethylfurfural [J].
Cuervo, Oscar H. Pardo ;
Simeonov, Svilen P. ;
Peixoto, Andreia F. ;
Popova, Margarita D. ;
Lazarova, Hristina, I ;
Romanelli, Gustavo P. ;
Martinez, Jose J. ;
Freire, Cristina ;
Afonso, Carlos A. M. .
ENERGY TECHNOLOGY, 2019, 7 (11)
[14]   The Eight Criteria Defining a Good Chemical Manufacturing Process [J].
Dach, Rolf ;
Song, Jinhua J. ;
Roschangar, Frank ;
Samstag, Wendelin ;
Senanayake, Chris H. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (11) :1697-1706
[15]   Recent advancements in the production of hydroxymethylfurfural [J].
Dashtban, Mehdi ;
Gilbert, Allan ;
Fatehi, Pedram .
RSC ADVANCES, 2014, 4 (04) :2037-2050
[16]   Top Chemical Opportunities from Carbohydrate Biomass: A Chemist's View of the Biorefinery [J].
Dusselier, Michiel ;
Mascal, Mark ;
Sels, Bert F. .
SELECTIVE CATALYSIS FOR RENEWABLE FEEDSTOCKS AND CHEMICALS, 2014, 353 :1-40
[17]  
Erle P.E.W., 2012, Ullmanns Encyclopedia of Industrial Chemistry, V2, P263
[18]   5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals [J].
Fan, Weigang ;
Verrier, Charlie ;
Queneau, Yves ;
Popowycz, Florence .
CURRENT ORGANIC SYNTHESIS, 2019, 16 (04) :583-614
[19]   Second-Generation Process for the HCV Protease Inhibitor BILN 2061: A Greener Approach to Ru-Catalyzed Ring-Closing Metathesis [J].
Farina, Vittorio ;
Shu, Chutian ;
Zeng, Xinazhong ;
Wei, Xudong ;
Han, Zhengxu ;
Yee, Nathan K. ;
Senanayake, Chris H. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (02) :250-254
[20]   When Will 5-Hydroxymethylfurfural, the "Sleeping Giant" of Sustainable Chemistry, Awaken? [J].
Galkin, Konstantin, I ;
Ananikov, Valentine P. .
CHEMSUSCHEM, 2019, 12 (13) :2976-2982