Top

Cellulose

Published in:

14-07-2021 | Original Research

Directional synthesis of furfural compounds from holocellulose catalyzed by sulfamic acid

Authors: Yuchan Lu, Qiao He, Qiao Peng, Wenhai Chen, Qunpeng Cheng, Guangsen Song, Guozhi Fan

Published in: Cellulose | Issue 13/2021

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

The coproduction of 5-hydroxymethylfurfural (5-HMF) and furfural (FUR) via the direct hydrolysis of holocellulose analogue composed of cellulose and hemicellulose was investigated. The effects of catalyst amount, solvent type and amount, reaction temperature and time using sulfamic acid with dual active sites as catalyst were also studied. The yields of 5-HMF and FUR at 37.2% and 62.0% were obtained with the volume ratio of γ-valerolactone to water of 25:1 at 180 °C for 3 h. The conversion of corn cob holocellulose and wheat straw holocellulose to furfural compounds was then carried out under the identical conditions. Yields of 5-HMF at 26.6% and 28.5%, and yields of FUR at 34.5% and 26.1% were obtained, respectively. A possible mechanism for the coproduction of 5-HMF and FUR from holocellulose was proposed. It is believed that there is a synergistic effect between the hydrolysis of cellulose and hemicellulose during the conversion of holocellulose.

Graphic abstract

previous article The effect of drying method on the porosity of regenerated cellulose fibres

next article Synthesis of novel heterocyclic compounds based on dialdehyde cellulose: characterization, antimicrobial, antitumor activity, molecular dynamics simulation and target identification

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Antal MJ Jr, Leesomboon T, Mok WS et al (1991) Mechanism of formation of 2-furaldehyde from D-xylose. Carbohyd Res 217:71–85CrossRef

Atanda L, Silahua A, Mukund S et al (2015) Catalytic behaviour of TiO₂-ZrO₂ binary oxide synthesized by sol-gel process for glucose conversion to 5-hydroxymethylfurfural. RSC Adv 5(98):80346–80352CrossRef

Atanda L, Konarova M, Ma Q et al (2016) High yield conversion of cellulosic biomass into 5-hydroxymethylfurfural and a study of the reaction kinetics of cellulose to HMF conversion in a biphasic system. Catal Sci Technol 6(16):6257–6266CrossRef

Benson GA, Spillane WJ (1980) Sulfamic acid and its N-substituted derivatives. Chem Rev 80(2):151–186CrossRef

Bringué R, Ramírez E, Iborra M et al (2019) Esterification of furfuryl alcohol to butyl levulinate over ion-exchange resins. Fuel 257:116010CrossRef

Cao Z, Fan Z, Chen Y et al (2019) Efficient preparation of 5-hydroxymethylfurfural from cellulose in a biphasic system over hafnyl phosphates. Appl Catal B 244:170–177CrossRef

Despax S, Estrine B, Hoffmann N et al (2013) Isomerization of D-glucose into D-fructose with a heterogeneous catalyst in organic solvents. Catal Commun 39:35–38CrossRef

Dias AS, Lima S, Carriazo D et al (2006) Exfoliated titanate, niobate and titanoniobate nanosheets as solid acid catalysts for the liquid-phase dehydration of D-xylose into furfural. J Catal 244(2):230–237CrossRef

Dotsenko AS, Dotsenko GS, Senko OV et al (2018) Complex effect of lignocellulosic biomass pretreatment with 1-butyl-3-methylimidazolium chloride ionic liquid on various aspects of ethanol and fumaric acid production by immobilized cells within SSF. Bioresource Technol 50(2):429–438CrossRef

Dunlop AP (1948) Furfural formation and behavior. Ind Eng Chem Res 40(2):204–209CrossRef

Fan GZ, Wang YX, Hu ZX et al (2018) Synthesis of 5-hydroxymethyl furfural from cellulose via a two-step process in polar aprotic solvent. Carbohyd Polym 200:529–535CrossRef

Hansen TS, Woodley JM, Riisager A et al (2009) Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose. Carbohyd Res 344(18):2568–2572CrossRef

Horváth IT, Mehdi H, Fábos V et al (2008) γ-Valerolactone-a sustainable liquid for energy and carbon-based chemicals. Green Chem 10(2):238–242CrossRef

Hsu WH, Lee YY, Peng WH et al (2011) Cellulosic conversion in ionic liquids (ILs): effects of H₂O/cellulose molar ratios, temperatures, times, and different ILs on the production of monosaccharides and 5-hydroxymethylfurfural (HMF). Catal Today 174(1):65–69CrossRef

Huijgen WJJ, Smit AT, Reith JH et al (2011) Catalytic organosolv fractionation of willow wood and wheat straw as pretreatment for enzymatic cellulose hydrolysis. J Chem Technol Biotechnol 86(11):1428–1438CrossRef

Kim HS, Park MR, Jeon YJ et al (2018) Valorization of chitosan as food waste of aquatic organisms into 5-hydroxymethylfurfural by sulfamic acid-catalyzed conversion process. Energy Technol 6(9):1747–1754CrossRef

Lam E, Majid E, Leung ACW et al (2011) Synthesis of furfural from xylose by heterogeneous and reusable nafion catalysts. Chemsuschem 4(4):535–541PubMedCrossRef

Lee SB, Jeong GT (2015) Catalytic conversion of chitosan to 5-hydroxymethylfurfural under low temperature hydrothermal process. Appl Biochem Biotech 176(4):1151–1161CrossRef

Li H, Ren J, Zhong L et al (2015) Production of furfural from xylose, water-insoluble hemicelluloses and water-soluble fraction of corncob via a tin-loaded montmorillonite solid acid catalyst. Bioresource Technol 176:242–248CrossRef

Lima S, Dias AS, Lin Z et al (2008) Isomerization of D-glucose to D-fructose over metallosilicate solid bases. Appl Catal A 339(1):21–27CrossRef

Lin Q, Li H, Wang X et al (2017) SO₄²⁻/Sn-MMT solid acid catalyst for xylose and xylan conversion into furfural in the biphasic system. Catalysts 7(4):118–132CrossRef

Liu L, Li K, Hao X et al (2016) Astragalus liquid in Arab xylan (AX-I-1) extraction and purification, structural analysis and in vitro antioidant effect. Chem J Chin U 37(12):2168–2175 (Chinese)

Long J, Xu Y, Zhao W et al (2019) Heterogeneous catalytic upgrading of biofuranic aldehydes to alcohols. Front Chem 7:529–593PubMedPubMedCentralCrossRef

Lou WY, Zong MH, Duan ZQ et al (2008) Efficient production of biodiesel from high free fatty acid-containing waste oils using various carbohydrate-derived solid acid catalysts. Bioresource Technol 99(18):8752–8758CrossRef

Mika LT, Cséfalvay E, Horváth IT et al (2015) The role of water in catalytic biomass-based technologies to produce chemicals and fuels. Catal Today 247:33–46CrossRef

Mirzaei HM, Karimi B (2016) Sulphanilic acid as a recyclable bifunctional organocatalyst in the selective conversion of lignocellulosic biomass to 5-HMF. Green Chem 18(8):2282–2286CrossRef

Pei YC, Nu YJ, Zhang WJ et al (2020) Recent progress in ionic liquids-based microemulsions. Sci Sin Chim 20(2):211–222

Rodriguez-Rodriguez N, Machiels L, Binnemans K et al (2019) p-Toluenesulfonic acid-based deep-eutectic solvents for solubilizing metal oxides. ACS Sustain Chem Eng 7(4):3940–3948CrossRef

Román-Leshkov Y, Chheda JN, Dumesic JA et al (2006) Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312(5782):1933–1937PubMedCrossRef

Román-Leshkov Y, Dumesic JA (2009) Solvent effects on fructose dehydration to 5-hydroxymethylfurfural in biphasic systems saturated with inorganic salts. Top Catal 52(3):297–303CrossRef

Shi N, Liu Q, Zhang Q et al (2013) High yield production of 5-hydroxymethylfurfural from cellulose by high concentration of sulfates in biphasic system. Green Chem 15(7):1967–1974CrossRef

Shi N, Liu Q, Wang T et al (2014) One-pot degradation of cellulose into furfural compounds in hot compressed steam with dihydric phosphates. ACS Sustaina Chem Eng 2(4):637–642CrossRef

Sudarsanam P, Peeters E, Makshina EV et al (2019) Advances in porous and nanoscale catalysts for viable biomass conversion. Chem Soc Rev 48(8):2366–2421PubMedCrossRef

Sun J, Yuan X, Shen Y et al (2015) Conversion of bamboo fiber into 5-hydroxymethylfurfural catalyzed by sulfamic acid with microwave assistance in biphasic system. Ind Crop Prod 70:266–271CrossRef

Sweygers N, Harrer J, Dewil R et al (2018) A microwave-assisted process for the in-situ production of 5-hydroxymethylfurfural and furfural from lignocellulosic polysaccharides in a biphasic reaction system. J Clean Prod 187:1014–1024CrossRef

Sweygers N, Depuydt DEC, Van-Vuure AW et al (2020) Simultaneous production of 5-hydroxymethylfurfural and furfural from bamboo (Phyllostachys nigra “Boryana”) in a biphasic reaction system. Chem Eng J 386:123957CrossRef

Tschirner S, Weingart E, Teevs L et al (2018) Catalytic dehydration of fructose to 5-hydroxymethylfurfural (HMF) in low-boiling solvent hexafluoroisopropanol (HFIP). Molecules 23(8):1866–1877PubMedCentralCrossRef

Van-Zandvoort I, Wang Y, Rasrendra CB et al (2013) Formation, molecular structure, and morphology of humins in biomass conversion: influence of feedstock and processing conditions. Chemsuschem 6(9):1745–1758PubMedCrossRef

Wang XH (2019) Efficient preparation of furfural from bagasse and utilization of furfural residue. S China Univ Technol (Chinese)

Weingarten R, Cho J, Conner JWC et al (2010) Kinetics of furfural production by dehydration of xylose in a biphasic reactor with microwave heating. Green Chem 12(8):1423–1429CrossRef

Weingarten R, Rodriguez-Beuerman A, Cao F et al (2014) Selective conversion of cellulose to hydroxymethylfurfural in polar aprotic solvents. ChemCatChem 6(8):2229–2234CrossRef

Whitaker MR, Parulkar A, Brunelli NA et al (2020) Selective production of 5-hydroxymethylfurfural from fructose in the presence of an acid-functionalized SBA-15 catalyst modified with a sulfoxide polymer. Mol Syst Des Eng 5(1):257–268CrossRef

Yu BW, Fan GZ, Zhao SJ et al (2021) Simultaneous isolation of cellulose and lignin from wheat straw and catalytic conversion to valuable chemical products. Appl Biol Chem 64(1):1–13CrossRef

Yuan B, Guan J, Peng J et al (2017) Green hydrolysis of corncob cellulose into 5-hydroxymethylfurfural using hydrophobic imidazole ionic liquids with a recyclable, magnetic metalloporphyrin catalyst. Chem Eng J 330:109–119CrossRef

Zhang Z, Dong K, Zhao ZK et al (2011) Efficient conversion of furfuryl alcohol into alkyl levulinates catalyzed by an organic-inorganic hybrid solid acid catalyst. Chemsuschem 4(1):112–118PubMedCrossRef

Zhang HY, Wang Y, Shao SS et al (2016) An experimental and kinetic modeling study including coke formation for catalytic pyrolysis of furfural. Combust Flame 17(3):258–265CrossRef

Zhang Q, Wang C, Mao J et al (2019) Insights on the efficiency of bifunctional solid organocatalysts in converting xylose and biomass into furfural in a GVL-water solvent. Ind Crop Prod 138:111454CrossRef

Zhang RQ, Ma CL, Shen YF et al (2020a) Enhanced biosynthesis of furoic acid via the effective pretreatment of corncob into furfural in the biphasic media. Catal Lett 150(8):2220–2227CrossRef

Zhang RQ, Ma CL, Shen YF et al (2020b) Enhanced biosynthesis of furoic acid via the efective pretreatment of corncob into furfural in the biphasic media. Catal Lett 2(3):1–8

Title: Directional synthesis of furfural compounds from holocellulose catalyzed by sulfamic acid
Authors: Yuchan Lu
Qiao He
Qiao Peng
Wenhai Chen
Qunpeng Cheng
Guangsen Song
Guozhi Fan
Publication date: 14-07-2021
Publisher: Springer Netherlands
Published in: Cellulose / Issue 13/2021
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-021-04070-8

Springer Professional

Abstract

Graphic abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Springer Professional "Wirtschaft+Technik"

Other articles of this Issue 13/2021

Fabrication of flexible AgNW/cellulose hybrid film with heat preservation and antibacterial properties for agriculture application

Biodegradable and transparent films with tunable UV-blocking property from Lignocellulosic waste by a top-down approach

Macroporous cellulose/carbon nanotube microspheres prepared by surfactant micelle swelling strategy for rapid and high-capacity adsorption of bilirubin

Preparation of a novel P/Si polymer and its synergistic flame retardant application on cotton fabric

Construction of conductive hydroxyethyl cellulose/soy protein isolate/polypyrrole composite sponges and their performances

Nitro-oxidized carboxycellulose nanofibers from moringa plant: effective bioadsorbent for mercury removal