Skip to main content
Erschienen in: Cellulose 4/2018

24.02.2018 | Original Paper

High-yield production of 5-hydroxymethylfurfural from d-fructose, d-glucose, and cellulose by its in situ removal from the reaction system

verfasst von: Kota Enomoto, Takashi Hosoya, Hisashi Miyafuji

Erschienen in: Cellulose | Ausgabe 4/2018

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

5-Hydroxymethylfurfural (5-HMF) from lignocellulosics has attracted attention as a platform chemical in chemical industry. In 5-HMF production processes, undesired degradation of 5-HMF by acid catalysts generally occurs, by which the 5-HMF yield is decreased along with formation of various types of by-products. In this study, we employed an acidic ionic liquid, 1-methylimidazolium hydrogen sulfate ([HMIM]HSO4), as a reaction medium for 5-HMF production and carried out in situ removal of 5-HMF from the reaction solution by on-line vacuum steam distillation. In our reaction system, 76.1% 5-HMF yield was achieved from d-glucose, which yield was very similar to that from d-fructose (77.3%). Various types of cellulose samples also gave 5-HMF with the yield up to 68.3% regardless of their molecular weights and crystallinities. The 5-HMF produced was recovered as an aqueous solution with substantial purity and almost no contamination with the ionic liquid.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

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!

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!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
Zurück zum Zitat Amarasekara AS, Williams LD, Ebede CC (2008) Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study. Carbohydr Res 343:3021–3024CrossRef Amarasekara AS, Williams LD, Ebede CC (2008) Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study. Carbohydr Res 343:3021–3024CrossRef
Zurück zum Zitat Binder JB, Raines RT (2009) Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 131:1979–1985CrossRef Binder JB, Raines RT (2009) Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 131:1979–1985CrossRef
Zurück zum Zitat Christov LP, Akhtar M, Prior BA (1998) The potential of biosulfite pulping in dissolving pulp production. Enzyme Microb Technol 23:70–74CrossRef Christov LP, Akhtar M, Prior BA (1998) The potential of biosulfite pulping in dissolving pulp production. Enzyme Microb Technol 23:70–74CrossRef
Zurück zum Zitat Daorattanachai P, Khemthong P, Viriya-empikul N, Laosiripojana N, Faungnawakij K (2012) Conversion of fructose, glucose, and cellulose to 5-hydroxymethylfurfural by alkaline earth phosphate catalysts in hot compressed water. Carbohydr Res 363:58–61CrossRef Daorattanachai P, Khemthong P, Viriya-empikul N, Laosiripojana N, Faungnawakij K (2012) Conversion of fructose, glucose, and cellulose to 5-hydroxymethylfurfural by alkaline earth phosphate catalysts in hot compressed water. Carbohydr Res 363:58–61CrossRef
Zurück zum Zitat Dee SJ, Bell AT (2011) A study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and the factors influencing the dehydration of glucose and the formation of humins. Chemsuschem 4:1166–1173CrossRef Dee SJ, Bell AT (2011) A study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and the factors influencing the dehydration of glucose and the formation of humins. Chemsuschem 4:1166–1173CrossRef
Zurück zum Zitat Girisuta B, Janssen LPBM, Heeres HJ (2006) A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid. Green Chem 8:701–709CrossRef Girisuta B, Janssen LPBM, Heeres HJ (2006) A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid. Green Chem 8:701–709CrossRef
Zurück zum Zitat Hu S, Zhang Z, Song J, Zhou Y, Han B (2009) Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid. Green Chem 11:1746–1749CrossRef Hu S, Zhang Z, Song J, Zhou Y, Han B (2009) Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid. Green Chem 11:1746–1749CrossRef
Zurück zum Zitat Hu X, Lievens C, Larcher A, Li CZ (2011) Reaction pathways of glucose during esterification: effects of reaction parameters on the formation of humin type polymers. Bioresour Technol 102:10104–10113CrossRef Hu X, Lievens C, Larcher A, Li CZ (2011) Reaction pathways of glucose during esterification: effects of reaction parameters on the formation of humin type polymers. Bioresour Technol 102:10104–10113CrossRef
Zurück zum Zitat Hubbell CA, Ragauskas AJ (2010) Effect of acid-chlorite delignification on cellulose degree of polymerization. Bioresour Technol 101:7410–7415CrossRef Hubbell CA, Ragauskas AJ (2010) Effect of acid-chlorite delignification on cellulose degree of polymerization. Bioresour Technol 101:7410–7415CrossRef
Zurück zum Zitat Ito R, Miyafuji H, Miyazaki Y, Kawai T (2016) Production of 5-hydroxymethylfurfural from wood by ionic liquid treatment. J Wood Sci 62:349–355CrossRef Ito R, Miyafuji H, Miyazaki Y, Kawai T (2016) Production of 5-hydroxymethylfurfural from wood by ionic liquid treatment. J Wood Sci 62:349–355CrossRef
Zurück zum Zitat Kvernheim AL, Lystad E (1989) Size-exclusion chromatography and methylation analysis of cellulose in N,N-dimethylacetamide/LiCl. Acta Chem Scand 43:209–211CrossRef Kvernheim AL, Lystad E (1989) Size-exclusion chromatography and methylation analysis of cellulose in N,N-dimethylacetamide/LiCl. Acta Chem Scand 43:209–211CrossRef
Zurück zum Zitat Li YN, Wang JQ, He LN, Yang ZZ, Liu AH, Yu B, Luan CR (2012) Experimental and theoretical studies on imidazolium ionic liquid-promoted conversion of fructose to 5-hydroxymentylfurfural. Green Chem 14:2752–2758CrossRef Li YN, Wang JQ, He LN, Yang ZZ, Liu AH, Yu B, Luan CR (2012) Experimental and theoretical studies on imidazolium ionic liquid-promoted conversion of fructose to 5-hydroxymentylfurfural. Green Chem 14:2752–2758CrossRef
Zurück zum Zitat Lima S, Neves P, Antunes MM, Pillinger M, Ignatyev N, Valente AA (2009) Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids. Appl Catal 363:93–99CrossRef Lima S, Neves P, Antunes MM, Pillinger M, Ignatyev N, Valente AA (2009) Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids. Appl Catal 363:93–99CrossRef
Zurück zum Zitat Pagán-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA (2012) Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Brønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent. ACS Catal 2:930–934CrossRef Pagán-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA (2012) Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Brønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent. ACS Catal 2:930–934CrossRef
Zurück zum Zitat Patil SKR, Heltzel J, Lund CRF (2012) Comparison of structural features of humins formed catalytically from glucose, fructose, and 5-hydroxymethylfurfuraldehyde. Energy Fuels 26:5281–5293CrossRef Patil SKR, Heltzel J, Lund CRF (2012) Comparison of structural features of humins formed catalytically from glucose, fructose, and 5-hydroxymethylfurfuraldehyde. Energy Fuels 26:5281–5293CrossRef
Zurück zum Zitat Qi X, Watanabe M, Aida TM, Smith RL Jr. (2009) Efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in ionic liquids at room temperature. Chemsuschem 2:944–946CrossRef Qi X, Watanabe M, Aida TM, Smith RL Jr. (2009) Efficient catalytic conversion of fructose into 5-hydroxymethylfurfural in ionic liquids at room temperature. Chemsuschem 2:944–946CrossRef
Zurück zum Zitat Qian X (2012) Mechanisms and energetics for Brønsted acid-catalyzed glucose condensation, dehydration and isomerization reactions. Top Catal 55:218–226CrossRef Qian X (2012) Mechanisms and energetics for Brønsted acid-catalyzed glucose condensation, dehydration and isomerization reactions. Top Catal 55:218–226CrossRef
Zurück zum Zitat Rass HA, Essayem N, Besson M (2015) Selective aerobic oxidation of 5-HMF into 2,5-furandicarboxylic acid with Pt catalysts supported on TiO2- and ZrO2-based supports. Chemsuschem 8:1206–1217CrossRef Rass HA, Essayem N, Besson M (2015) Selective aerobic oxidation of 5-HMF into 2,5-furandicarboxylic acid with Pt catalysts supported on TiO2- and ZrO2-based supports. Chemsuschem 8:1206–1217CrossRef
Zurück zum Zitat Román-Leshkov Y, Barrett CJ, Liu ZY, Dumesic JA (2007) Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447:982–986CrossRef Román-Leshkov Y, Barrett CJ, Liu ZY, Dumesic JA (2007) Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447:982–986CrossRef
Zurück zum Zitat Sarwono A, Man Z, Muhammad N, Khan AS, Suzaini W, Hamzah W, Rahim AHA, Ullah Z, Wilfred CD (2017) A new approach of probe sonication assisted ionic liquid conversion of glucose, cellulose and biomass into 5-hydroxymethylfurfural. Ultrason Sonochem 37:310–319CrossRef Sarwono A, Man Z, Muhammad N, Khan AS, Suzaini W, Hamzah W, Rahim AHA, Ullah Z, Wilfred CD (2017) A new approach of probe sonication assisted ionic liquid conversion of glucose, cellulose and biomass into 5-hydroxymethylfurfural. Ultrason Sonochem 37:310–319CrossRef
Zurück zum Zitat Segal L, Creely JJ, Martin AE Jr, Conrad CM (1959) An empirical method for estimating the degree of crystallinity of native cellulose using the X-ray diffractometer. Text Res J 29:786–794CrossRef Segal L, Creely JJ, Martin AE Jr, Conrad CM (1959) An empirical method for estimating the degree of crystallinity of native cellulose using the X-ray diffractometer. Text Res J 29:786–794CrossRef
Zurück zum Zitat Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 23:2399–2407CrossRef Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 23:2399–2407CrossRef
Zurück zum Zitat Shi J, Liu W, Wang N, Yang Y, Wang H (2014) Production of 5-hydroxymethylfurfural from mono- and disaccharides in the presence of ionic liquids. Catal Lett 144:252–260CrossRef Shi J, Liu W, Wang N, Yang Y, Wang H (2014) Production of 5-hydroxymethylfurfural from mono- and disaccharides in the presence of ionic liquids. Catal Lett 144:252–260CrossRef
Zurück zum Zitat Siankevich S, Fei Z, Scopelliti R, Jessop PG, Zhang J, Yan N, Dyson PJ (2016) Direct conversion of mono- and polysaccharides into 5-hydroxymethylfurfural using ionic-liquid mixtures. Chemsuschem 9:2089–2096CrossRef Siankevich S, Fei Z, Scopelliti R, Jessop PG, Zhang J, Yan N, Dyson PJ (2016) Direct conversion of mono- and polysaccharides into 5-hydroxymethylfurfural using ionic-liquid mixtures. Chemsuschem 9:2089–2096CrossRef
Zurück zum Zitat Sousa AF, Coelho JFJ, Silvestre AJD (2016) Renewable-based poly((ether)ester)s from 2,5-furandicarboxylic acid. Polymer 98:129–135CrossRef Sousa AF, Coelho JFJ, Silvestre AJD (2016) Renewable-based poly((ether)ester)s from 2,5-furandicarboxylic acid. Polymer 98:129–135CrossRef
Zurück zum Zitat Tamai N, Aono H, Tatsumi D, Matsumoto T (2003) Differences in rheological properties of solutions of plant and bacterial cellulose in LiCl/N,N-dimethylacetamide. J Soc Rheol Jpn 31:119–130CrossRef Tamai N, Aono H, Tatsumi D, Matsumoto T (2003) Differences in rheological properties of solutions of plant and bacterial cellulose in LiCl/N,N-dimethylacetamide. J Soc Rheol Jpn 31:119–130CrossRef
Zurück zum Zitat Tamai N, Tatsumi D, Matsumoto T (2004) Rheological properties and molecular structure of tunicate cellulose in LiCl/1,3-dimethyl-2-imidazolidinone. Biomacromolecules 5:422–432CrossRef Tamai N, Tatsumi D, Matsumoto T (2004) Rheological properties and molecular structure of tunicate cellulose in LiCl/1,3-dimethyl-2-imidazolidinone. Biomacromolecules 5:422–432CrossRef
Zurück zum Zitat Tong X, Li Y (2010) Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Brønsted-acidic ionic liquids. Chemsuschem 3:350–355CrossRef Tong X, Li Y (2010) Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Brønsted-acidic ionic liquids. Chemsuschem 3:350–355CrossRef
Zurück zum Zitat Van Putten RJ, Van der Waal JC, De Jong E, Rasrendra CB, Heeres HJ, De Vries JG (2013) Hydroxymethylfurfural, A versatile platform chemical made from renewable resources. Chem Rev 113:1499–1597CrossRef Van Putten RJ, Van der Waal JC, De Jong E, Rasrendra CB, Heeres HJ, De Vries JG (2013) Hydroxymethylfurfural, A versatile platform chemical made from renewable resources. Chem Rev 113:1499–1597CrossRef
Zurück zum Zitat Wang J, Xu W, Ren J, Liu X, Lu G, Wang Y (2011) Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid. Green Chem 13:2678–2681CrossRef Wang J, Xu W, Ren J, Liu X, Lu G, Wang Y (2011) Efficient catalytic conversion of fructose into hydroxymethylfurfural by a novel carbon-based solid acid. Green Chem 13:2678–2681CrossRef
Zurück zum Zitat Weingarten R, Conner WC Jr., Huber GW (2012) Production of levulinic acid from cellulose by hydrothermal decomposition combined with aqueous phase dehydration with a solid acid catalyst. Energy Environ Sci 5:7559–7574CrossRef Weingarten R, Conner WC Jr., Huber GW (2012) Production of levulinic acid from cellulose by hydrothermal decomposition combined with aqueous phase dehydration with a solid acid catalyst. Energy Environ Sci 5:7559–7574CrossRef
Zurück zum Zitat Yang G, Pidko EA, Hensen EJM (2012) Mechanism of Brønsted acid-catalyzed conversion of carbohydrates. J Catal 295:122–132CrossRef Yang G, Pidko EA, Hensen EJM (2012) Mechanism of Brønsted acid-catalyzed conversion of carbohydrates. J Catal 295:122–132CrossRef
Zurück zum Zitat Yokoyama K, Miyafuji H (2016) Production of furan compounds from rice straw with ionic liquid treatment. J Jpn Inst Energy 95:902–908CrossRef Yokoyama K, Miyafuji H (2016) Production of furan compounds from rice straw with ionic liquid treatment. J Jpn Inst Energy 95:902–908CrossRef
Zurück zum Zitat Yoshioka K, Yamada T, Ohno H, Miyafuji H (2015) Production of 2-hydroxyacetylfuran from lignocellulosics treated with ionic liquid–water mixtures. RSC Adv 5:72405–72409CrossRef Yoshioka K, Yamada T, Ohno H, Miyafuji H (2015) Production of 2-hydroxyacetylfuran from lignocellulosics treated with ionic liquid–water mixtures. RSC Adv 5:72405–72409CrossRef
Zurück zum Zitat Zhang Z, Zhao ZK (2010) Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid. Bioresour Technol 101:1111–1114CrossRef Zhang Z, Zhao ZK (2010) Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid. Bioresour Technol 101:1111–1114CrossRef
Zurück zum Zitat Zhang Z, Wang Q, Xie H, Liu W, Zhao Z (2011) Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by Germanium(IV) chloride in ionic liquids. Chemsuschem 4:131–138CrossRef Zhang Z, Wang Q, Xie H, Liu W, Zhao Z (2011) Catalytic conversion of carbohydrates into 5-hydroxymethylfurfural by Germanium(IV) chloride in ionic liquids. Chemsuschem 4:131–138CrossRef
Zurück zum Zitat Zhang C, Cheng Z, Fu Z, Liu Y, Yi X, Zheng A, Kirk SR, Yin D (2017) Effective transformation of cellulose to 5-hydroxymethylfurfural catalyzed by fluorine anion-containing ionic liquid modified biochar sulfonic acids in water. Cellulose 24:95–106CrossRef Zhang C, Cheng Z, Fu Z, Liu Y, Yi X, Zheng A, Kirk SR, Yin D (2017) Effective transformation of cellulose to 5-hydroxymethylfurfural catalyzed by fluorine anion-containing ionic liquid modified biochar sulfonic acids in water. Cellulose 24:95–106CrossRef
Zurück zum Zitat Zhao H, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316:1597–1600CrossRef Zhao H, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316:1597–1600CrossRef
Metadaten
Titel
High-yield production of 5-hydroxymethylfurfural from d-fructose, d-glucose, and cellulose by its in situ removal from the reaction system
verfasst von
Kota Enomoto
Takashi Hosoya
Hisashi Miyafuji
Publikationsdatum
24.02.2018
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 4/2018
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-018-1717-3

Weitere Artikel der Ausgabe 4/2018

Cellulose 4/2018 Zur Ausgabe