Advances in humins formation mechanism, inhibition strategies, and value-added applications

doi:10.1016/S1872-2067(24)60248-2

Chinese Journal of Catalysis ›› 2025, Vol. 71: 25-53.DOI: 10.1016/S1872-2067(24)60248-2

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Advances in humins formation mechanism, inhibition strategies, and value-added applications

Yitong Wang^a^,¹, Chaofeng Zhang^b^,¹, Cheng Cai^a^,^*(), Caoxing Huang^b, Xiaojun Shen^c, Hongming Lou^d, Changwei Hu^e, Xuejun Pan^f, Feng Wang^g^,^*(), Jun Xie^a^,^*()

^aKey Laboratory of Energy Plants Resource and Utilization, Guangdong Engineering Technology Research Center for Agricultural and Forestry Biomass, Institute of Biomass Engineering, South China Agricultural University, Guangzhou 510642, Guangdong, China
^bJiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Light Industry and Food Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China
^cState Key Laboratory of Efficient Production of Forest Resources, Beijing Forestry University, Beijing 100083, China
^dSchool of Chemistry and Chemical Engineering, Guangdong Provincial Key Lab of Green Chemical Product Technology, South China University of Technology, Guangzhou 510641, Guangdong, China
^eKey Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610065, Sichuan, China
^fDepartment of Biological Systems Engineering, University of Wisconsin-Madison, 460 Henry Mall, Madison, WI, 53706, USA
^gState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2024-12-18 Accepted:2025-02-08 Online:2025-04-18 Published:2025-04-13
Contact: * E-mail: wangfeng@dicp.ac.cn (F. Wang), chengcai@scau.edu.cn (C. Cai),xiejun@scau.edu.cn (J. Xie).
About author:Cheng Cai graduated from the School of Chemistry and Chemical Engineering, South China University of Technology in 2020, and carried out postdoctoral work at the Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China in 2021. Now he is working in the Institute of Biomass Engineering, South China Agricultural University. His main interests include chemical catalytic conversion of lignocellulose, immobilization of enzyme, preparation and application of lignin and cellulosic materials.
Feng Wang received his PhD degree from the Dalian Institute of Chemical Physics, Chinese Academy of Sciences in 2005, and went to the University of California, Berkeley, USA for postdoctoral work in the same year. He is currently the Deputy Director of Dalian Institute of Chemical Physics, Chinese Academy of Sciences. His research interests include multiphase catalytic reactions, catalytic conversion of biomass, photocatalytic conversion, life cycle assessment and economic and technology assessment.
Jun Xie graduated from the College of Life Sciences of Sichuan University in 2001 with a Doctor of Science degree, and joined South China Agricultural University (SCAU) in August 2003 as a professor and supervisor of doctoral students. He is currently the Director of the Institute of Biomass Engineering, South China Agricultural University. His main research areas are catalytic conversion of biomass energy, efficient energy and medicinal plant resources and utilization, and preparation and application of small molecule collagen peptides.
¹Contributed to this work equally.
Supported by:
National Key Research and Development Program of China(2021YFC2101602);National Natural Science Foundation of China(22378150);National Natural Science Foundation of China(32471809);Young Talent Support Project of Guangzhou Association for Science and Technology(QT2024-009);Research Fund for High-level Talents Introduction of Nanjing Forestry University(163105164);Natural Science Foundation of Jiangsu Province(BK20220106)

Abstract

Abstract:

Humins, as a group of by-products formed through the condensation and coupling of fragment intermediates during lignocellulosic biomass refining, can cause numerous negative effects such as the wastage of carbon resources, clogging of reactor piping, deactivation of catalyst, and barriers to product separation. Elucidating the generation mechanism of humins, developing efficient inhibitors, and even utilizing them as a resource, both from the perspective of atom economy and safe production, constitutes a research endeavor replete with challenges and opportunities. Orbiting the critical issue of humins structure and its generation mechanism from cellulose and hemicellulose resources, the random condensation between intermediates such as 5-hydroxymethylfurfural, furfural, 2,5-dioxo-6-hydroxyhexanal, and 1,2,4-benzenetriol etc. were systematically summarized. Additionally, the presence of lignin in real biorefining processes further promotes the formation of a special type of humins known as "pseudo-lignin". The influences of various factors, including raw materials, reaction temperature and time, acid-base environment, as well as solvent systems and catalysts, on the formation of humins were comprehensively analyzed. To minimize the formation of humins, the design of efficient solvent systems and catalysts is crucial. Furthermore, this review investigates the approaches to value-added applications of humins. The corresponding summary could provide guidance for the development of the humins chemistry.

Key words: Humins, Lignocellulosic, Biomass refining, Biomass conversion, Pseudo-lignin

Yitong Wang, Chaofeng Zhang, Cheng Cai, Caoxing Huang, Xiaojun Shen, Hongming Lou, Changwei Hu, Xuejun Pan, Feng Wang, Jun Xie. Advances in humins formation mechanism, inhibition strategies, and value-added applications[J]. Chinese Journal of Catalysis, 2025, 71: 25-53.

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Figures/Tables 16

Fig. 1. Generation of humins in lignocellulosic biomass refining and its value-added applications.

Fig. 2. Main pathways and intermediates of cellulose, hemicellulose, and lignin-derived humins.

Fig. 3. (a) Pathway of HMF hydration to form LA and DHH [37]. (b) Possible pathways for the formation of humins via DHH [42,43]. (c) Pathways for the formation of humins via α-carbonyl aldehydes and α,β-unsaturated aldehydes [44].

Fig. 4. Possible pathways for HMF intermolecular condensation and HMF condensation with LA and FA to form humins [31,46,47].

Fig. 5. (a) The elementary structure of humins formed by glucose dehydration [49]. (b) Acetal cyclization of glucose and HMF to form humins moieties and pathway of the formation of water-soluble oligomers of D-Glucose [51,53]. (c) Possible pathways of fructose-derived humins [59].

Fig. 6. Structure of humins element formed by self-condensation of FF and condensation with oxidation products [31,76,79,81].

Fig. 7. Mechanism of xylose-derived humins [79].

Fig. 8. Mechanism of pseudo-lignin formation.

Fig. 9. (a,b) Molecular structure models of cellulose-derived humins [35,52]. (c) Molecular structure model of hemicellulose-derived humins [52]. (d) Mechanism of aromatic fragment formation in DHH [42]. (e) Possible mechanism of BTO formation [27]. (f) The mechanism of Diels-Alder reaction to form phenolic compounds of humins [84]. (g) The structural model of alkali-treated humins [111].

Fig. 10. Diagram of different structures caused by raw materials and reaction conditions in humins.

Fig. 11. Inhibition strategies of humins.

Fig. 12. Value-added application of humins.

Fig. 13. Schematic diagram of pyrolytic conversion and drug synthesis of humins [178,179].

Fig. 14. Schematic diagram of humins based resin and humins foams synthesis [187,190].

Fig. 15. Humins application in the field of catalysts [196,198,200].

Fig. 16. Schematic of humins used as a functional carbon material [46,202,203].

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