Evolution Process and Controlled Synthesis of Humins with 5-Hydroxymethylfurfural (HMF) as Model Molecule.

5-hydroxymethylfurfural aldol reaction biomass humins reactive intermediates

Journal

ChemSusChem

ISSN: 1864-564X

Titre abrégé: ChemSusChem

Pays: Germany

ID NLM: 101319536

Informations de publication

Date de publication:
07 Feb 2020

Historique:

received: 10 10 2019

pubmed: 21 11 2019

medline: 21 11 2019

entrez: 21 11 2019

Statut: ppublish

Résumé

Elucidation of the chemical structure and formation mechanism of humins is a requisite to further improve the efficiency of acid-catalyzed biomass conversion. Through a low-temperature approach, the key intermediates resulting in the formation of 5-hydroxymethylfurfural (HMF)-derived humins were captured, revealing multiple elementary reactions such as etherification, esterification, aldol condensation, and acetalization. Through humin characterization, it was found out that the aldol condensation moiety between aldehyde group and levulinic acid is critical to justify the characteristic IR peaks (1620 and 1710 cm

Identifiants

DOI: 10.1002/cssc.201902799 PMID: 31746122

pubmed: 31746122

doi: 10.1002/cssc.201902799

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

513-519

Subventions

Organisme : Fundamental Research Funds for the Central Universities

ID : DUT18JC16

Organisme : the Key Laboratory of Biomass Energy and Materials of Jiangsu Province.

ID : JSBEM201809

Informations de copyright

Références

A. J. Ragauskas, C. K. Williams, B. H. Davison, G. Britovsek, J. Cairney, C. A. Eckert, W. J. Frederick, Jr., J. P. Hallett, D. J. Leak, C. L. Liotta, J. R. Mielenz, R. Murphy, R. Templer, T. Tschaplinski, Science 2006, 311, 484-489;

G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106, 4044-4098;

A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502;

J. C. Serrano-Ruiz, R. Luque, A. Sepulveda-Escribano, Chem. Soc. Rev. 2011, 40, 5266-5281;

D. M. Alonso, S. G. Wettstein, J. A. Dumesic, Chem. Soc. Rev. 2012, 41, 8075-8098;

C. O. Tuck, E. Perez, I. T. Horvath, R. A. Sheldon, M. Poliakoff, Science 2012, 337, 695-699;

Z. R. Zhang, J. L. Song, B. X. Han, Chem. Rev. 2017, 117, 6834-6880.

B. Girisuta, L. P. B. M. Janssen, H. J. Heeres, Ind. Eng. Chem. Res. 2007, 46, 1696-1708;

C. Li, Z. K. Zhao, Adv. Synth. Catal. 2007, 349, 1847-1850;

S. J. Dee, A. T. Bell, ChemSusChem 2011, 4, 1166-1173;

S. Van De Vyver, J. Geboers, P. A. Jacobs, B. F. Sels, ChemCatChem 2011, 3, 82-94;

H. Ren, Y. Zhou, L. Liu, Bioresour. Technol. 2013, 129, 616-619;

H. Ren, B. Girisuta, Y. Zhou, L. Liu, Carbohydr. Polym. 2015, 117, 569-576.

M. E. Zakrzewska, E. Bogel-Łukasik, R. Bogel-Łukasik, Chem. Rev. 2011, 111, 397-417;

R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev. 2013, 113, 1499-1597;

H. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Science 2007, 316, 1597-1600;

J. N. Chheda, Y. Roman-Leshkov, J. A. Dumesic, Green Chem. 2007, 9, 342-350;

D. W. Rackemann, W. O. S. Doherty, Biofuels Bioprod. Biorefin. 2011, 5, 198-214;

L. Liu, Z. Li, W. Hou, H. Shen, Carbohydr. Polym. 2018, 181, 778-784;

W. Hou, L. Liu, H. Shen, Carbohydr. Polym. 2018, 195, 267-274.

J. P. Lange, R. Price, P. M. Ayoub, J. Louis, L. Petrus, L. Clarke, H. Gosselink, Angew. Chem. Int. Ed. 2010, 49, 4479-4483;

Angew. Chem. 2010, 122, 4581-4585.

M. Sevilla, A. B. Fuertes, Chem. Eur. J. 2009, 15, 4195-4203;

M. Sevilla, A. B. Fuertes, Carbon 2009, 47, 2281-2289.

A. Chuntanapum, Y. Matsumura, Ind. Eng. Chem. Res. 2009, 48, 9837-9846.

M. M. Titirici, M. Antonietti, N. Baccile, Green Chem. 2008, 10, 1204-1212.

C. Falco, N. Baccile, M. M. Titirici, Green Chem. 2011, 13, 3273-3281;

N. Baccile, G. Laurent, F. Babonneau, F. Fayon, M. M. Titirici, M. Antonietti, J. Phys. Chem. C 2009, 113, 9644-9654;

C. Falco, F. P. Caballero, F. Babonneau, C. Gervais, G. Laurent, M. M. Titirici, N. Baccile, Langmuir 2011, 27, 14460-14471;

L. H. Yu, C. Falco, J. Weber, R. J. White, J. Y. Howe, M. M. Titirici, Langmuir 2012, 28, 12373-12383.

J. Horvat, B. Klaic, B. Metelko, V. Sunjic, Tetrahedron Lett. 1985, 26, 2111-2114;

J. Horvat, B. Klaic, B. Metelko, V. Sunjic, Croat. Chem. Acta 1986, 59, 429-438.

I. V. Sumerskii, S. M. Krutov, M. Y. Zarubin, Russ. J. Appl. Chem. 2010, 83, 320-327.

S. K. R. Patil, C. R. F. Lund, Energy Fuels 2011, 25, 4745-4755;

S. K. R. Patil, J. Heltzel, C. R. F. Lund, Energy Fuels 2012, 26, 5281-5293.

I. van Zandvoort, Y. H. Wang, C. B. Rasrendra, E. R. H. van Eck, P. C. A. Bruijnincx, H. J. Heeres, B. M. Weckhuysen, ChemSusChem 2013, 6, 1745-1758.

G. Tsilomelekis, M. J. Orella, Z. Lin, Z. Cheng, W. Zheng, V. Nikolakis, D. G. Vlachos, Green Chem. 2016, 18, 1983-1993.

K. I. Galkin, E. A. Krivodaeva, L. V. Romashov, S. S. Zalesskiy, V. V. Kachala, J. V. Burykina, V. P. Ananikov, Angew. Chem. Int. Ed. 2016, 55, 8338-8342;

Angew. Chem. 2016, 128, 8478-8482.

C. B. Rasrendra, M. Windt, Y. Wang, S. Adisasmito, I. G. B. N. Makertihartha, E. R. H. van Eck, D. Meier, H. J. Heeres, J. Anal. Appl. Pyrolysis 2013, 104, 299-307.

J. Ryu, Y. W. Suh, D. J. Suh, D. J. Ahn, Carbon 2010, 48, 1990-1998.

Y.-T. Cheng, G. W. Huber, Green Chem. 2012, 14, 3114-3125.

S. Agarwal, D. van Es, H. J. Heeres, J. Anal. Appl. Pyrolysis 2017, 123, 134-143.