Abstract
Polyfunctionality of carbohydrates and their low solubility in conventional organic solvents make rather complex their conversion to higher value added chemicals. Therefore, innovative processes are now strongly needed in order to increase the selectivity of these reactions. Here, we report an overview of the different heterogeneously-catalyzed processes described in the literature. In particular, hydrolysis, dehydration, oxidation, esterification, and etherification of carbohydrates are presented. We shall discuss the main structural parameters that need to be controlled and that permit the conversion of carbohydrates to bioproducts with good selectivity. The conversion of monosaccharides and disaccharides over solid catalysts, as well as recent advances in the heterogeneously-catalyzed conversion of cellulose, will be presented.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- BMIM:
-
1-Butyl 3-methyl imidazolium
- ChCl:
-
Choline chloride
- DMSO:
-
Dimethylsulfoxide
- HMF:
-
5-Hydroxymethylfurfural
- HMS:
-
Hexagonal mesoporous silica
- IL:
-
Ionic liquid
- PMO:
-
Periodic mesoporous organosilica
- PS:
-
Polystyrene
- TBD:
-
Triazabicyclo[4.4.0.]dec-5-ene
- TOF:
-
Turn over frequency
References
Narayan R (1992) Emerging technologies for materials and chemicals from biomass. American Chemical Society, Washington, DC
Eissen M, Metzger JO, Schmid E, Schneidewind U (2002) Angew Chem 41:414–436
Barrault J, Pouilloux Y, Clacens JM, Vanhove C, Bancquart S (2002) Catal Today 75:177–181
Deffeyes KS (1981) Beyond oil: the view from Hubbert’s peak. Farrar Straus and Giroux, New York
Chow J, Kopp RJ, Portney PR (2003) Science 302:1528–1531
Corma A, Iborra S, Velty A (2007) Chem Rev 107:2411–2502
Clark JH, Macquarrie DJ (2002) Handbook of green chemistry and technology. Blackwell, Oxford
Clark JH (1999) Green Chem:1–8
Anastas PA, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford
Neier W (1991) Ion exchangers as catalysts. W. der Gruyter, Germany, p 1060
McGovern TJ, Dranoff JS (2004) Anniversary article. Bioengineering, food, and natural products. AIChE J 16:536–546
Cunha LM, Oliveira FAR (2000) J Food Eng 46:53–60
Anastas PT, Kirchhoff MM (2002) Acc Chem Res 35:686–694
Lichtenthaler FW (1991) Carbohydates as organic materials, vol 1. VCH, Weinheim
Descotes G (1993) Carbohydates as organic materials, vol 2. VCH, Weinheim
Van Bekkun H, Ropper H, Voragen AGJ (1996) Carbohydates as organic materials, vol 3. CRF, The Hague
Praznik W, Huber A (1998) Carbohydates as organic materials, vol 4. WUV-Universitätsverlag, Wien
Kunz M (1990) In: Lichtenthaler FW (ed) Carbohydrates as organic raw materials. New York, VCH
Lichtenthaler FW, Peters S (2004) C R Chim 7:65–90
Queneau Y, Fitremann J, Trombotto S (2004) C R Chim 7:177–188
Okuhara T (2002) Chem Rev 102:3641–3666
Zhang H (1989) CN Patent 1048233
Satyanarayana B, Varma YBG (1970) Indian J Technol 8:58–61
Masroua A, Revillon A, Martin JC, Guyot A, Descotes G (1988) Bull Soc Chim Fr 3:561–566
Hahn-Hägerdal B, Skoog K, Mattiasson B (1983) Eur J Microbiol Biotechnol 17:344–348
Yoshioka T, Shimamura M (1984) Bull Chem Soc Jpn 57:334–337
Mizota T, Tsuneda S, Saito K, Sugo T (1994) Ind Eng Chem Res 33:2215–2219
Nasefa MM, Saidia H, Sennab MM (2005) Chem Eng J 108:13–17
Abd El-Mohdy HL, Abd El-Rehim HA (2008) Chem Eng J 145:154–159
Chambré D, Idiţoiu C, Szabo MR (2007) J Thermal Anal Calorim 88:681–686
Chambre D, Szabo MR, Popescu C, Idiţoiu C (2008) J Thermal Anal Calorim 94:417–420
Buttersack C, Laketic D (1994) J Mol Catal 94:L283–L290
Bootsma JA, Shanks BH (2007) Appl Catal A 327:44–51
Hoffmann F, Cornelius M, Morell J, Fröba M (2006) Angew Chem Int Ed 45:3216–3251
Inagaki S, Guan S, Ohsuna T, Terasaki O (2002) Nature 416:304–307
Rac B, Hegyes P, Forgo P, Molnar A (2006) Appl Catal A 299:193–201
Rat M, Zahedi-Niaki MH, Kaliaguine S, Do TO (2008) Microporous Mesoporous Mater 112:26–31
Yang Q, Kapoor MP, Inagaki S, Shirokura N, Kondo JN, Domen K (2005) J Mol Catal A 230:85–89
Yang Q, Liu J, Kapoor MP, Inagaki S, Li C (2004) J Catal 228:265–272
Dhepe PL, Ohashi M, Inagaki S, Ichikawa M, Fukuoka A (2005) Catal Lett 102:163–169
Takagaki A, Tagusagawa C, Domen K (2008) Chem Commun:5363–5365
Toda M, Takagaki A, Okamura M, Kondo JN, Hayashi S, Domen K, Hara M (2005) Nature 438:178
Okamura M, Takagaki A, Toda M, Kondo JN, Domen K, Tatsumi T, Hara M, Hayashi S (2006) Chem Mater 18:3039–3045
Nakajima K, Hara M (2007) J Am Ceram Soc 90:3725–3734
Yamaguchi D, Kitano M, Suganuma S, Nakajima K, Kato H, Hara M (2009) J Phys Chem C 113:3181–3188
Suganuma S, Nakajima K, Kitano M, Yamaguchi D, Kato H, Hayashi S, Hara M (2008) J Am Chem Soc 130:12787–12793
Onda A, Ochi T, Yanagisawa K (2009) Top Catal 52:801–807
Dhepe LP, Fukuoka A (2008) ChemSusChem 1:969–975
Fukuoka A, Dhepe LP (2006) Angew Chem 47:8510–8513
Luo C, Wang S, Liu H (2007) Angew Chem 46:7636–7639
Deng W, Tan X, Fang W, Zhang Q, Wang Y (2009) Catal Lett. doi: 10.1007/s10562-009-0136-3
Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Chen JG (2008) Angew Chem 47:8510–8513
Ji N, Zhang T, Zheng M, Wang A, Wang H, Wang X, Shu Y, Stottlemyer AL, Chen JG (2009) Catal Today 147:77–85
Rinaldi R, Palkovits R, Schüth F (2008) Angew Chem 47:1–5
Lichtenthaler FW (2002) Acc Chem Res 35:728–737
Gandini A (1992) Polymers from renewable resources. In: Aggarwal SL, Russo S (eds) Comprehensive polymer science, Suppl 1. Pergamon, Oxford
Kunz M (1993) Hydroxymethylfurfural, a possible basic chemical for industrial intermediates. In: Fuchs A (ed) Inulin and inulin-containing crops. Elsevier, Amsterdam
Gandini A, Belgacem MN (2002) Actual Chim:56–59
Moreau C, Belgacem MN, Gandini A (2004) Top Catal 27:11–30
Cottier L, Descotes G (1991) Trends Heterocycl Chem 2:233–248
Faury A, Gaset A, Gorrichon JP (1981) Inf Chim 214:203
Gaset A, Gorrichon JP, Truchot E (1981) Inf Chim 212:179
Kuster BFM (1990) Starch/Stärke 42:314–321
Lewkowski J (2001) ArkiVoc 2:17–54
Dull G (1895) Chem Ztg 19:216–220
Kiermayer J (1895) Chem Ztg 19:1003–1006
Haworth WN, Jones WGM (1944) J Chem Soc Chem Soc:667–670
Van Dam HE, Kieboom APG, Van Bekkum H (1986) Starch/Stärke 38:95–101
Antal MJ, Mok WSL, Richards GN (1990) Carbohydr Res 199:91–109
Cottier L, Descotes G, Neyret C, Nigay H (1989) Ind Aliment Agricol:567–570
Pummerer R, Guyot O, Birkofer L (1935) Chem Ber 68B:480–493
Horvat J, Klaic B, Metelko B, Sunjic V (1985) Tetrahedron Lett 26:2111
Jing Q, Xiuyang LU (2008) Chin J Chem Eng 16:890–894
Carlini C, Giuttari M, Raspolli Galletti AM, Sbrana G, Armaroli T, Busca G (1999) Appl Catal A 183:295–302
Benvenuti F, Carlini C, Patrono P, Raspolli Galletti AM, Sbrana G, Massucci MA, Galli P (2000) Appl Catal A 193:147–153
Carlini C, Patrono P, Raspolli Galletti AM, Sbrana G (2004) Appl Catal A 275:111–118
Asghari FS, Yoshida H (2006) Carbohydr Res 341:2379–2387
Watanabe M, Aizawa Y, Toru I, Nishimura Ryo, Inomata H (2005) Appl Catal A 295:150–156
Watanabe M, Aizawa Y, Iida T, Aida TM, Levy C, Sue K, Inomata H (2005) Carbohydr Res 340:1925–1930
Qi X, Watanabe M, Aida TM, Smith RL Jr (2008) Catal Commun 9:2244–2249
Lourvanij K, Rorrer GL (1994) Appl Catal A 109:147–165
Jow J, Rorrer GL, Hawley MC, Lamport DTA (1987) Biomass 14:185–194
Lourvanij K, Rorrer GL (1993) Ind Eng Chem Res 32:11–19
Moreau C, Durand R, Razigade S, Duhamet J, Faugeras P, Rivalier P, Ros P, Avignon G (1996) Appl Catal A 145:211–224
Moreau C, Durand R, Pourcheron C, Razigade S (1994) Ind Crops Prod 3:85–90
Nakamura Y, Morikawa S (1980) Bull Chem Soc Jpn 53:3705–3706
Cottier L, Descotes G, Neyret C, Nigay H (1990) FR 9011479
Brown DW, Floyd AJ, Kinsman RG, Roshanhyphen Y (1982) J Chem Technol Biotechnol 32:920–924
El Hajj T, Masroua A, Martin JC, Descotes G (1987) Bull Soc Chim Fr 855–860
Mercadier D, Rigal L, Gaset A, Gorrichon JP (1981) J Chem Technol Biotechnol 31:503–508
Takagaki A, Ohara M, Nishimura S, Ebitani K (2009) Chem Commun. doi: 10.1039/b914087e
Qi X, Watanabe M, Aida TM, Smith RL Jr (2008) Green Chem 8:799–805
Fleche G, Gaset A, Gorrichon JP, Truchot E, Sicard P (1982) US 4339487
Rigal L, Gorrichon JP, Gaset A, Heughebaert JC (1985) Biomass 7:27–45
Lansalot-Matras C, Moreau C (2003) Catal Commun 4:517–520
Qi X, Watanabe M, Aida TM, Smith RL (2009) ChemSusChem. doi: 10.1002/cssc.200900199
Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, König B (2009) Green Chem. doi: 10.1039/b917548m
Collins PM, Ferrier RJ (1995) Oxidations monosaccharides: their chemistry and their role in natural products. Wiley, New York
Madsen R (2008) Oxidation, reduction and deoxygenation. In: Fraser-Reid BO, Tatsuta K, Thiem J (eds) Glycoscience, chemistry and chemical biology, oxidation, reduction and deoxygenation. Springer, Heidelberg
Besemer AC, Van Bekkum H (1996) Calcium sequestering agents based on carbohydrates. In: Van Bekkum H, Röper H, Voragen AGJ (eds) Carbohydrates as organic raw materials. VCH, Wheineim
de Nooy AEJ, Besemer AC, Van Bekkum H (1998) New polyelectrolytes by selective oxidation of polysaccharides. In: Praznik W, Huber H (eds) Carbohydrates as organic raw materials. WUV, Vienna
Mäki-Arvela P, Holmbom B, Salmi T, Murzin DY (2007) Catal Rev 49:197–340
Fritsche-Lang W, Leopold I, Schlingmann M (1987) DE Patent 3535720
Kunz M, Puke H, Recker C, Scheiwe L, Kowalczyk J (1994) DE 4307388
Kunz M, Schwarz A, Kowalczyk J (1997) DE 19542287
Edye LA, Meehan GV, Richards GN (1994) J Carbohydr Chem 13:273–283
Edye LA, Meehan GV, Richards GN (1991) J Carbohydr Chem 10:11–23
Ramachandran S, Fontanille P, Pandey A, Larroche C (2006) Food Technol Biotechnol 44:185–195
Dirkx JMH, Van der Ban HS (1981) J Catal 67:1–13
Abbadi A, Van Bekkum H (1995) J Mol Cat A Chem 97:111–118
Hattori K, Miya B, Matsuda M, Ishii M, Saito H, Watanabe H, Takizawa H (1976) JP 53040713
Besson M, Gallezot P, Lahmer E, Flèche G, Fuertes P (1993) Oxidation of glucose on palladium catalysts: particle size and support effects. In: Kosak JR, Johnson TA (eds) Catalysis of organic reactions. Marcel Dekker, New York
Fuertes P, F1èche G, Frères R (1987) EP 233816
Besson M, Flèche G, Fuertes P, Gallezot P, Lahmer F (1996) Recl Trav Chim Pays Bas 115:217–221
Besson M, Lahmer F, Gallezot P, Fuertes P, Flèche G (1995) J Catal 152:116–121
Gallezot P (1997) Catal Today 37:405–418
Karski S, Witońska I, Gołuchowska J (2006) J Mol Cat A Chem 245:225–230
Bönnemann H, Brijoux W, Brinkmann R, Schulze Tilling A, Schilling T, Tesche B, Seevogel B, Franke R, Hormes J, Köhl G, Pollmann J, Rothe J, Vogel W (1998) Inorg Chim Acta 270:95–110
Biella S, Prati L, Rossi M (2002) J Catal 206:242–247
Önal Y, Schimpf S, Claus P (2004) J Catal 223:122–133
Comotti M, Della Pina C, Matarrese R, Rossi M, Siani A (2005) Appl Catal A 291:204–209
Beltrame P, Della Pina C, Rossi M, Comotti M (2006) Appl Catal A 297:1–7
Mirescu A, Prüße U (2006) Catal Commun 7:11–17
Huford JR (1980) Surface-active agents derived from disaccharides. In: Lee CK (ed) Developments in food carbohydrates. Applied Science, England
Kosaka T, Yamada T (1977) New plant and applications of sucrose esters. In: Hickson JL (ed) Sucrochemistry. ACS Symposium Series, Washington, DC
Okabe S, Suganuma M, Tada Y, Ochiai Y, Sueoka E, Kohya H, Shibata A, Takahashi M, Mizutani M, Matsuzaki T, Fujiki H (1999) Jpn J Cancer Res 90:669–676
Puterka GJ, Farone W, Palmer T, Barrington A (2003) J Econ Entomol 96:636–644
Wang Y (1988) Synthesis and application of sucrose ester. Light Industrial, London
Kharchafi G, Jerôme K, Adam I, Pouilloux Y, Barrault J (2005) New J Chem 26:928–934
Van Rhijn W, De Vos D, Bossaert W, Bullen J, Wouters B, Grobet P, Jacobs P (1998) Stud Surf Sci Catal 117:183–190
Corma A, Hamid SBA, Iborra S, Velty A (2008) ChemSusChem 1:85–90
Van Es DS, Frissen AE, Luitjes H (2001) WO 2001083488
Usmani AM, Salyer IO (1981) Org Coatings Appl Polym Sci Proc 46:269
Ronan P, Adam I, Fitremann J, Jérôme F, Bouchu A, Courtois G, Barrault J, Queneau Y (2004) C R Chimie 7:151–160
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer
About this chapter
Cite this chapter
Vigier, K.D.O., Jérôme, F. (2010). Heterogeneously-Catalyzed Conversion of Carbohydrates. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development II. Topics in Current Chemistry, vol 295. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_55
Download citation
DOI: https://doi.org/10.1007/128_2010_55
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-15160-6
Online ISBN: 978-3-642-15161-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)