Catalytic conversion of biosourced raw materials: Homogeneous catalysis

Biorefinery: From Biomass to Chemicals and Fuels

Volumn , Issue , 2012, Pages 231-262

  Fischmeister, Cédric ^a   Bruneau, Christian ^a   De Oliveira Vigier, Karine ^b   Jérôme, François ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE POITIERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85119650112     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (100)

1. Alcaide, B., Almendros, P., Luna, A. (2009). Grubbs' ruthenium-carbenes beyond the metathesis reaction: less conventional non-metathetic utility. Chem. Rev. 109: 3817-3858.
2. Alonso, D. M., Wettstein, S. G., Bond, J. Q., Root, T. W., Dumesic, J. (2011). Production of biofuels from cellulose and corn stover using alkylphenol solvents. ChemSusChem DOI: 10.1002/cssc.201100256.
3. Behr, A., Johnen, L. (2009). Myrcene as a natural base chemical in sustainable chemistry: A critical review. ChemSusChem. 2: 1072-1095.
4. Behr, A., Leschinski, J., Awungacha, C., Simic, S., Knoth, T. (2009). Telomerization of butadiene with glycerol: Reaction control through process engineering, solvents, and additives. ChemSusChem 2: 71-76.
5. Behr, A., Pérez Gomes, J., Bayrak, Z. (2011). Cross-metathesis of methyl 10-undecenoate with diethyl maleate: Formation of an α,ω-diester via a metathesis reaction network. Eur. J. Lipid Sci. Technol. 113: 189-196.
6. Behr, A., Urschey, M. (2003). Highly selective biphasic telomerization of butadiene with glycols: Scope and limitations. Adv. Synth. Catal. 345: 1242-1246.
7. Behr, A., Westfechtel, A., Pérez Gomes, J. (2008). Catalytic processes for the technical use of natural Fats and oils. Chem. Eng. Technol. 31: 700-714.
8. Biermann, U., Bornscheuer, U., Meier M. A. R., Metzger, J. O., H. J. Schäfer (2011). Oils and fats as renewable raw materials in chemistry. Angew. Chem. Int. Ed. 50: 3854-3871.
9. Bilel, H., Hamdi, N., Zagrouba, F., Fischmeister, C., Bruneau, C. (2011). Cross-metathesis transformations of terpenoids in dialkyl carbonate solvents. Green Chem. 13: 1448-1452.
10. Binder, J.B., Raines, R.T. (2009). Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J. Am. Chem. Soc. 131:1979-1985.
11. Borré, E., Dinh, T. H., Caijo, F., Crévisy, C., Mauduit, M. (2011). Terpenic compounds as renewable sources of raw materials for cross-metathesis. Synthesis. DOI: 10.1055/s-0030-1260605.
12. Bosma, R. H. A., van Aardweg, F., Mol, J. C. (1981). Cometathesis of methyl oleate and ethylene; A direct route to methyl dec-9-enoate. J. Chem. Soc. Chem. Commun. 1132-1133.
13. Bozell, J. J., Petersen, G. R. (2010). Technology development for the production of biobased products from biorefinery carbohydrates - the US Department of Energy's "Top 10" revisited. Green Chem. 12(4), 539-554.
14. Braden, D. J., Henao, C. A., Heltzel, J., Maravelias, C. C., Dumesic, J. (2011). Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid. Green Chem. 13: 1755-1765.
15. Burdett, K. A., Harris, L. D., Margl, P., Maughon, B. R., Mokhtar-Zadeh, T., Saucier, P. C., Wasserman, E. P. (2004). Renewable monomer feedstocks via olefin metathesis: Fundamental mechanistic studies of methyl oleate ethenolysis with the first-generation Grubbs catalyst. Organometallics 23: 2027-2047.
16. Christmann, M. (2010). Otto Wallach: founder of terpene chemistry and Nobel laureate 1910. Angew. Chem. Int. Ed. 49: 9580-9586.
17. Clark, J. H. (2006). Green chemistry: today (and tomorrow). Green Chem. 8: 17-21.
18. Climent, M. J., Corma, A., Iborra, S. (2011). Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals. Chem. Rev. 1 1 1(2): 1072-1133.
19. Corma, A., Iborra, S., Velty, A. (2007). Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 107: 241 1-2502.
20. Dinger, M. B., Mol, J. C. (2002). High turnover numbers with ruthenium-based metathesis catalysts. Adv. Synth. Catal. 344: 671-677.
21. Diver, S. T., Giessert, A. J. (2004). Enyne metathesis (enyne bond reorganization). Chem. Rev. 104: 1317-1382.
22. Fischmeister, C., Bruneau, C. (2011). Ene-yne cross-metathesis with ruthenium carbene catalysts. Beilstein J. Org. Chem. 7: 156-166.
23. Fogg, D. E., dos Santos, E. N. (2004). Tandem catalysis: a taxonomy and illustrative review. Coord. Chem. Rev. 248: 2365-2379.
24. Gallezot, P. (2008). Catalytic conversion of biomass: Challenges and issues. ChemSusChem 1: 734-737.
25. Gaudin, P., Jacquot, R., Marion, P., Pouilloux, Y., Jérôme, F. (2011a). Acid-catalyzed etherifi-cation of glycerol with long alkyl chain alcohols. ChemSusChem 4: 719-722.
26. Gaudin, P., Jacquot, R., Marion, P., Pouilloux, Y., Jérôme, F. (2011b). Homogeneously-catalyzed etherification of glycerol with 1-dodecanol. Catal. Sci. Technol. 1: 616-620.
27. Geboerts, J., Van de Vyver, S., Carpentier, K., de Blochouse, K., Jacobs, P., Sels, B. (2010). Efficient catalytic conversion of concentrated cellulose feeds to hexitols with heteropolyacid and Ru on carbon. Chem. Commun. 46: 3577-3579.
28. Geboerts, J., Van de Vyver, S., Carpentier, K., Jacobs, P., Sels, B. (2011a). Hydrolytic hydrogenation of cellulose with hydrotreated caesium salts of heteropolyacids and Ru/C. Green Chem. DOI: 10.1039/c1gc15350a.
29. Geboerts, J., Van de Vyver, S., Carpentier, K., Jacobs, P., Sels, B. (2011b). Efficient hydrolytic hydrogenation of cellulose in the presence of Ru-loaded zeolites and trace amounts of mineral acid. Chem. Commun. 47: 5590-5592.
30. Gordillo, A., Duran Pachon, L., De Jesus, E., Rothenberg, G. (2009). Palladium-catalysed telomerisation of isoprene with glycerol and polyethylene glycol: A facile route to new terpene derivatives. Adv. Synth. Catal. 351: 325-330.
31. Gu, Y., Azzouzi, A., Pouilloux, Y., Jérôme, F., Barrault, J. (2008). Heterogeneously catalyzed etherification of glycerol: New pathways for transformation of glycerol to more valuable chemicals. Green Chem. 10: 164-167.
32. Gunstone F. D. (2011). Supplies of vegetable oils for non-food purposes. Eur. J. Lipid Sci. Technol. 113: 3-7.
33. Gutiérrez, S., Tlenkopatchev, M. A. (2011). Metathesis of renewable products: Degradation of natural rubber via cross-metathesis with β-pinene using Ru-alkylidene catalysts. Polym. Bull. 66: 1029-1038.
34. Hoveyda, A. H., Zhugralin, A. R. (2007). The remarkable metal-catalysed olefin metathesis reaction. Nature 450: 243-251.
35. Hoye, T. R., Zhao, H. (1999). Some allylic substituent effects in ring-closing metathesis reactions: Allylic alcohol activation. Org. Lett. 7: 1123-1125.
36. Hu, S., Brown, H. M., Huang, X., Zhou, X., Amonette, J. E., Zhang, Z. C. (2009). Single-step conversion of cellulose to 5-hydroxymethylfurfural (HMF), a versatile platform chemical. Appl. Catal. A Gen. 361: 117-122.
37. Jérôme, F., Pouilloux, Y., Barrault, J. (2008). Rational design of solid catalysts for the selective use of glycerol as a natural organic building block. ChemSusChem 1(7): 586-613.
38. Jimenez Rodriguez, C., Foster, D. F., Eastham, G. R., Cole-Hamilton, D. J. (2004). Highly selective formation of linear esters from terminal and internal alkenes catalysed by palladium complexes of bis-(di-tert-butylphosphinomethyl)benzene. Chem. Commun. 1720-1721.
39. 2 pretreatment of lignocellulose enhances enzymatic cellulose hydrolysis. Bioresour. Technol. 77: 139-144.
40. Klepacova, K., Mravec, D., Bajus, M. (2005). Tert butylation of glycerol catalyzed by ionexchange resins. Appl. Catal. A: Gen. 294: 141-147.
41. Klepacova, K., Mravec, D., Bajus, M. (2006). Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins. Chem. Pap. 60: 224-230.
42. Köckritz, A., Blumenstein, M., Martin, A. (2009). Catalytic cleavage of methyl oleate or oleic acid. Eur. J. Lipid Sci. Technol. 111: 58-63.
43. Kootstra, A. M. J., Beeftink, H. H., Scott, E. L., Sanders, J.P.M. (2009). Comparison of dilute mineral acid and organic acid pretreatment for enzymatic hydrolysis of wheat straw. Biochem. Eng. J. 46: 126-131.
44. Lee, J-W., Jeffries, T. W. (2011). Efficiencies of acid catalysts in the hydrolysis of lignocellulosic biomass over a range of combined severity factors. Bioresour. Technol. 102: 5884-5890.
45. Le Ravalec, V., Dupé, A., Fischmeister, C., Bruneau, C. (2010). Improving sustainability in Ene-Yne cross-metathesis for transformation of unsaturated fatty esters. ChemSusChem. 3: 1291-1297.
46. Le Ravalec, V., Fischmeister, C., Bruneau, C. (2009). First transformation of unsaturated fatty esters involving enyne cross-metathesis. Adv. Synth. Catal. 351: 1115-1122.
47. Li, C., Wang, Q., Zhao, Z. K. (2008). Acid in ionic liquid: An efficient system for hydrolysis of lignocellulose. Green chem. 10: 177-182.
48. Liu, L., Sun, J., Cai, C., Wang, S., Pei, H., Zhang J. (2009). Corn stover pretreatment by inorganic salts and its effects on hemicellulose and cellulose degradation. Bioresour. Technol. 100: 5865-5871.
49. Liu, C., Wyman, C. E. (2006). The enhancement of xylose monomer and xylotriose degradation by inorganic salts in aqueous solutions at 180°C. Carbohydrate Research 341: 2550-2556.
50. Lora, J. H., Glasser, W. G. (2002). Recent industrial applications of lignin: A sustainable alternative to nonrenewable materials. J Polym Environ 10: 39-48.
51. Lu, Y., Larock, R. C. (2009). Novel polymeric materials from vegetable oils and vinyl monomers: Preparation, properties, and applications. ChemSusChem. 2: 136-147.
52. Luiz, J., Monteiro, F., Veloso, C. O. (2004). Catalytic conversion of terpenes into fine chemicals. In H. van Bekkum and P. Gallezot (Eds.), Topics in Organometallic chemistry, 169-180. New York: Springer.
53. Luque, R., Budarin, V., Clark, J. H., Macquarrie, D. J. (2008). Glycerol transformations on polysaccharide derived mesoporous materials. Appl. Catal. B: Env. 82: 157-162.
54. Malacea, R., Fischmeister, C., Bruneau, C., Dubois, J.-L., Couturier, J.-L., Dixneuf, P. H. (2009). Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile. Green Chem. 11: 152-155.
55. Marcotullio, G., De Jong, W. (2010). Chloride ions enhance furfural formation from D-xylose in dilute aqueous acidic solutions. Green Chem. 12: 1739-1746.
56. 3 solutions under mild conditions. X-ray and thermo-gravimetric analysis of the solid residues. Bioresour. Technol. 102: 5917-5923.
57. Marinescu, S. M., Schrock, R. R., Müller, P., Hoveyda, A. H. (2009). Ethenolysis reactions catalyzed by imido alkylidene monoaryloxide monopyrrolide (MAP) complexes of molybdenum. J. Am. Chem. Soc. 131: 10840-10841.
58. Marshall, A-L., Alaimo, P. (2010). Useful products from complex starting materials: Common chemicals from biomass feedstocks. Chem. Eur. J. 16: 4970-4980.
59. Mascal, M., Nikitin, E. B. (2008). Direct, high-yield conversion of cellulose into biofuel. Angew. Chem. Int. 47: 7924-7926.
60. Meier, M. A. R. (2009). Metathesis with oleochemicals: New approaches for the utilization of plant oils as renewable resources in polymer science. Macromol. Chem. Phys. 210: 1073-1079.
61. Meylemans, H. A., Quintana, R. L., Goldsmith, B. R., Harvey, B. G. (2011). Solvent-free conversion of linalool to methylcyclopentadiene dimers: a route to renewable high-density fuels. ChemSusChem. 4: 465-469.
62. Miao, X., Fischmeister, C., Bruneau, C., Dixneuf, P. H. (2009). A direct route to bifunctional aldehyde derivatives via self- and cross-metathesis of unsaturated aldehydes. ChemSus-Chem. 2: 542-545.
63. Mosier, N., Wyman, C., Dale, B., Elander, R., Lee, Y. Y., Holtzapple, M., Ladisch M. (2005). features of promising technologies for pretreatment of lignocellulosic biomass. Bioresour. Technol. 96: 673-686.
64. Narayanaswamy, N., Faik, A., Goetz, D. J., Gu T. (2011). Supercritical carbon dioxide pretreatment of corn stover and switchgrass for lignocellulosic ethanol production. Bioresour. Technol. 102: 6995-7000.
65. Palkovits, R., Nieddu, I., Klein Gebbink, J. M., Weckhuysen, B. (2008a). Highly active catalysts for the telomerization of crude glycerol with 1,3-Butadiene. ChemSusChem 1: 193-196.
66. Palkovits, R., Nieddu, I., Kruithof, C. A., Klein Gebbink, R. J. M., Weckhuysen, B. (2008b). Palladium-based telomerization of 1,3-Butadiene with glycerol using methoxy-functionalized triphenylphosphine ligands. Chem. Eur. J. 14: 8995-9005.
67. Palkovits, R., Parvulescu, A. N., Hausoul, P. J. C., Kruithof, C. A., Klein Gebbink, R. J. M., Weckhuysen, B. (2009). Telomerization of 1,3-butadiene with various alcohols by Pd/TOMPP catalysts: New opportunities for catalytic biomass valorization. Green Chem. 11: 1155-1160.
68. Pariente, S., Tanchoux, N., Fajula, F. (2009). Etherification of glycerol with ethanol over solid acid catalysts. Green Chem. 8: 1256-1261.
69. Patel, J., Mujcinovic, S., Roy Jackson, W., Robinson, A. J., Serelis, A. K., Such, C., (2006). High conversion and productive catalyst turnovers in cross-metathesis reactions of natural oils with 2-butene. Green Chem. 8: 450-454.
70. Rybak, A., Meier, M. A. R. (2007). Cross-metathesis of fatty acid derivatives with methyl acrylate: Renewable raw materials for the chemical industry. Green Chem. 9: 1356-1361.
71. Rybak, A., Meier, M. A. R. (2008). Acyclic diene metathesis with a monomer from renewable resources: Control of molecular weight and one-step preparation of block copolymers. ChemSusChem. 1: 542-547.
72. Sadler, J. N. (1993). Introduction, bioconversion of forest and agricultural plant residues, biotechnology in agriculture N°9 CAB international UK 1-11.
73. Schrodi, Y., Ung, T., Vargas, A., Mkrtumyan, G., Lee, C. W., Champagne, T. M., Pederson, R. L., Hong S. H. (2008). Ruthenium olefin metathesis catalysts for the ethenolysis of renewable feedstocks. Clean 36: 669-673.
74. Shimizu, K., Furukawa, H., Kobayashi, N., Itaya, Y., Satsuma, A. (2009). Effects of Brønsted and Lewis acidities on activity and selectivity of heteropolyacid-based catalysts for hydrolysis of cellobiose and cellulose. Green Chem. 11: 1627-1632.
75. Sibeijn, M., Mol, J. C., (1992). Ethenolysis of methyl oleate over supported Re-based catalysts. J. Mol. Catal. 76: 345-358.
76. Simonetti, D. A., Dumesic, J. A. (2008). Catalytic strategies for changing the energy content and achieving CC coupling in biomass-derived oxygenated hydrocarbons. ChemSusChem 1(8-9): 725-733.
77. Soh, L., Zimmerman, J. B. (2011). Biodiesel production: the potential of algal lipids extracted with supercritical carbon dioxide. Green Chem. 13: 1422-1429.
78. 2/Zeolite/BMIMCl system. Biomass and Bioenergy 35: 1367-1370.
79. 2-ionic liquid system. Carbohydrate Polymers 85: 363-368.
80. Thomas, R. M., Keitz, B. K., Champagne, T. M., Grubbs, R. H. (2011). Highly selective ruthenium metathesis catalysts for ethenolysis. J. Am. Chem. Soc. 133: 7490-7493.
81. Thurier, C., Fischmeister, C., Bruneau, C., Olivier-Bourbigou, H., Dixneuf, P. H. (2008). Ethenolysis of methyl oleate in room temperature ionic liquids. ChemSusChem. 1: 118-122.
82. 40. Cellulose 17: 587-594.
83. Türünc, O., Meier, M. A. R. (2011). Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers. Green Chem. 13: 314-320.
84. van Dam, P. B., Mittlmeijer, M. C., Boelhouwer, C. (1972). Metathesis of unsaturated fatty acid esters by a homogeneous tungsten hexachloride-tetramethyltin catalyst. J. Chem. Soc., Chem. Commun. 1221-1222.
85. Van der Steen, M., Stevens, C. V. (2009). Undecylenic acid: A valuable and physiologically active renewable building block from castor oil. ChemSusChem. 2: 692-713.
86. Vennestrom, P. N. R., Christensen, C. H., Pedersen, S., Grunwaldt, J. D., Woodley, J. M. (2010). Next-generation catalysis for renewables: Combining enzymatic with inorganic heterogeneous catalysis for bulk chemical production. ChemCatChem 2: 249-258.
87. Verkuijlen, E., Kapteijn, F., Mol, J. C., Boelhouwer, C. (1977). Heterogeneous metathesis of unsaturated fatty acid esters. J. Chem. Soc. Chem. Commun. 198-199.
88. Vieille-Petit, L., Clavier, H., Linden, A., Blumentritt, S., Nolan, S. P., Dorta, R. (2010). Ruthenium olefin metathesis catalysts with N-Heterocyclic carbene ligands bearing N-naphthyl side chains. Organometallics 29: 775-788.
89. vom Stein, T., Grande, P. M., Kayser, H., Sibilla, F., Leitner, W., Dominguez de Maria, P. (2011). From biomass to feedstock: One-step fractionation of lignocelluloses components by the selective organic acid-catalyzed depolymerization of hemicellulose in a biphasic system. Green Chem. 13: 1772-1777.
90. Vougioukalakis, G. C., Grubbs, R. H. (2010). Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts. Chem. Rev. 110: 1746-1787.
91. Warwel, S., Tillack, J., Demes, C., Kunz, M. (2001). Polyesters of ω-unsaturated fatty acid derivatives. Macromol. Chem. Phys. 202: 1114-1121.
92. Wolf, S., Plenio, H. (2011). On the ethenolysis of natural rubber and squalene. Green Chem. DOI: 10.1039/c1gc15265c.
93. 2 on conversion of inulin to 5-hydroxymethylfurfural and propylene oxide to 1,2-propanediol in water. Green Chem. 12: 1215-1219.
94. Wyman, C. E. (1996). Handbook on bioethanol production and utilization. Washington, DC: Taylor Francis.
95. Yoshikai, K., Hayama, T., Nishimura, K., Yamada, K., Tomioka, K. (2005). Thiol-catalyzed acyl radical cyclization of alkenals. J. Org. Chem. 70: 681-683.
96. Zhang, Y. H. P., Ding, S. Y., Mielenz, J. R., Cui, J. B., Elander, R. T., Laser, M. (2007). Fractionating recalcitrant lignocellulose at modest reaction conditions. Biotechnol Bioeng 97: 214-223.
97. Zhang, Y., Du, H., Qian, X., Chen, E. Y. X. (2010). Ionic liquid-water mixtures: Enhanced Kw for efficient cellulosic biomass conversion. Energy Fuels 24: 2410-2417.
98. Zhao, H., Holladay, J. E., Brown, H., Zhang, Z. C. (2007). Metal chlorides in ionic liquid solvents convert sugars to 5-Hydroxymethylfurfural. Science 316: 1597-1600.
99. Zheng, Y. Z., Lin, H. M., Tsao, G. T. (1998). Pretreatment for cellulose hydrolysis by carbon dioxide explosion. Biotechnol. Progress 14: 890-896.
100. Zhu, Y., Patel, J., Mujcinovic, S., Jackson, W. R., Robinson, A. J. (2006). Preparation of terminal oxygenates from renewable natural oils by a one pot metathesis-isomerisation-methoxy-carbonylation-transesterification reaction sequence. Green Chem. 8: 746-749.