Polymerization of sugars/furan model compounds and bio-oil during the acid-catalyzed conversion – A review

doi:10.1016/j.fuproc.2021.106958

Fuel Processing Technology

Volume 222, November 2021, 106958

https://doi.org/10.1016/j.fuproc.2021.106958 Get rights and content

Highlights

•
The reaction behaviors of sugars/furan in water and in alcohols are discussed.
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The cross-polymerization among sugars/furans in acid-treatment is reviewed.
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Polymerization of sugars/furans during esterification of bio-oil is discussed.
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The methods for tackling polymerization of sugars/furans is discussed.

Abstract

Acid catalysis is one of the most important chemical processes for the conversion of biomass or biomass derivatives to value-added chemicals and biofuels. Polymerization is one of the bottleneck issues during the acid-catalyzed conversion, which consumes feedstock, diminishes the production of target products and results the deactivation of catalyst. In this review, we focus mainly on the previous work on the use of alcohols (compared with water) as the reaction media for suppressing the polymerization reactions during the acid-catalyzed conversion of C6 sugars, C5 sugars, furans, phenolics and bio-oil. Particular attention is paid to the analysis of the reaction networks involving sugars/furans during the acid-catalyzed conversion in water and alcohol media.

Graphical abstract

Section snippets

List of the acronyms

DMMF	2-(dimethoxymethyl)-5-(methoxymethyl)furan
DMM	dimethoxymethane/methanol
DMSO	dimethyl sulfoxide
DOF	2-(dimethoxymethyl)-furan
HDF	5-(hydroxymethyl)-2-(dimethoxymethyl)furan
HMF	5-hydroxymethylfurfural (HMF)
MAXP	methyl xylofuranoside
MFA	5-(methoxymethyl)-2-furancarboxadhyde
MGP	Methyl glucopyranosides
THF	tetrahydrofuran

Polymerization of C6 sugars in water and methanol

Among the varied methods for upgrading of bio-oil, esterification, in which acid catalyst is generally employed, is an important one with the main purpose for converting corrosive carboxylic acids into the neutral esters. However, under the condition of esterification, the sugars including levoglucosan also can also be converted, and thus it is of significance for investigating the reaction behaviors of the sugars in bio-oil. Since levoglucosan is generally the most abundant sugar monomer in

Quantification of acidic functional groups in bio-oil

Many polymerization reactions are catalyzed by acids [219]. In bio-oil such as the one produced by the pyrolysis of mallee leaves, there are numbers of carboxylic acids with varied structures present [220]. Furthermore, there are also heavy carboxylic acids that could not be detected with GC-MS. To quantify the total number of the carboxylic acids in bio-oil, a non-aqueous potentiometric titration method is developed [221].

The results show that abundant carboxylic acids present in the bio-oil,

Beneficial use of the polymerization of bio-oil for the production of solid biocarbon

The above discussion indicated that the major components of bio-oil are prone to polymerization on heating. The mechanisms for the polymerization have been studied intensively. The methods for tackling the polymerization of bio-oil such as the conversion of bio-oil or the major components of bio-oil in alcohol solvent have been developed. Alcohols could suppress the polymerization of some furans and sugars. Nevertheless, even in the alcohol media, some components like xylose and furfural are

Concluding remarks and outlook

The above sections briefly review the main work on understanding the effects of alcohol media on the polymerization reactions in the acid-catalyzed conversion of sugars, furans, phenolics and bio-oil. The drastic differences in terms of the polymer formation in water and in alcohol media has been observed. The protection of the C1 hydroxyl group in the glucose prevented the formation of the sugar oligomers, while the protection of the hydroxyl group and aldehyde group in HMF prevent the

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Chun-Zhu Li obtained his PhD in Chemical Engineering from Imperial College London in 1993. After postdoctoral experience, he joined Monash University in 1996. Professor Li has co-authored more than 300 papers in journals and conference proceedings. He has also edited a book, Advances in the Science of Victorian Brown Coal, and co-authored three chapters in the book. Professor Li moved to Curtin University of Technology in January 2009 to be the Director of Fuels and Energy Technology Institute (initially known as Curtin Centre for Advanced Energy Science and Engineering). He was a John Curtin Distinguished Professor. He is now an Adjunct Professor in The University of Western Australia. He is a co-inventor of 9 families of patents with more than 55 granted patent rights.

Xun Hu is currently a full professor in School of Material Science and Engineering, University of Jinan. He obtained his PhD degree from the Chinese Academy of Sciences in 2010. From 2010 to 2016, he worked in Fuels and Energy Technology Institute, Curtin University (Australia) as a Postdoctoral Research Fellow under the supervision of Professor Chun-Zhu Li and later hold a position of Curtin Research Fellow in Curtin University. Since October 2016, he joined University of Jinan (China) and established a research group. His major research interest includes the conversion of biomass into the functional carbon materials for the use in catalysis/energy storage, the development of heterogeneous catalysts for hydrogenation or acid-catalysis. He also works on pyrolysis/hydrolysis of biomass and the conversion of biomass to biofuels, value-added chemicals and carbon materials. His papers have been cited for ca. 6700 times by May 2021 and he has an h-index of 45. https://scholar.google.com.hk/citations?user=_08hJZYAAAAJ&hl=zh-CN&oi=sra

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Invited review articlePolymerization of sugars/furan model compounds and bio-oil during the acid-catalyzed conversion – A review

Highlights

Abstract

Graphical abstract

Section snippets

List of the acronyms

Polymerization of C6 sugars in water and methanol

Quantification of acidic functional groups in bio-oil

Beneficial use of the polymerization of bio-oil for the production of solid biocarbon

Concluding remarks and outlook

Declaration of Competing Interest

Renew. Sust. Energ. Rev.

Fuel Process. Technol.

Renew. Sust. Energ. Rev.

Ind. Crop. Prod.

Compos. Part B Eng.

Ind. Crop. Prod.

Fuel

Appl. Catal. A Gen.

Renew. Sust. Energ. Rev.

Catal. Commun.

Fuel Process. Technol.

Bioresour. Technol.

Fuel

J. Anal. Appl. Pyrolysis

Carbohyd. Polym.

J. Mol. Catal. A Chem.

Mol. Catal.

Catal. Today

J. Catal.

Catal. Today

Bioresour. Technol.

Bioresour. Technol.

Carbohydr. Res.

Bioresour. Technol. Rep.

Chem. Eng. J.

Chem. Eng. J.

Appl. Catal. A Gen.

Chem. Eng. J.

Chem. Eng. J.

Fuel Process. Technol.

Appl. Catal. B Environ.

Bioresour. Technol.

Fuel

Bioresour. Technol.

Catal. Commun.

Catal. Today

Renew. Sust. Energ. Rev.

Appl. Catal. A Gen.

Bioresour. Technol.

Appl. Catal. A Gen.

J. Catal.

Int. J. Biol. Macromol.

Coke formation during thermal treatment of bio-oil

Energy Fuel

Catalytic total hydrodeoxygenation of biomass-derived polyfunctionalized substrates to alkanes

ChemSusChem

Microwave-assisted hydrolysis of crystalline cellulose catalyzed by biomass char sulfonic acids

Green Chem.

Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering

Chem. Rev.

Synthesis of sugars by hydrolysis of hemicelluloses-a review

Chem. Rev.

Synthesis and utilisation of sugar compounds derived from lignocellulosic biomass

Green Chem.

A one‐pot method for the selective conversion of hemicellulose from crop waste into C5 sugars and furfural by using solid acid catalysts

ChemSusChem

Conversion of hemicellulose into furfural using solid acid catalysts in γ‐valerolactone

Angew. Chem. Int. Ed.

Invited review article
Polymerization of sugars/furan model compounds and bio-oil during the acid-catalyzed conversion – A review