The Biofine Process - Production of Levulinic Acid, Furfural, and Formic Acid from Lignocellulosic Feedstocks

Biorefineries-Industrial Processes and Products: Status Quo and Future Directions

Volumn 1, Issue , 2008, Pages 139-164

  Hayes, Daniel J ^a   Fitzpatrick, Steve ^b   Hayes, Michael H B ^a   Ross, Julian R H ^a  

^a UNIVERSITY OF LIMERICK   (Ireland)

^b Biofine Inc   (United States)

Author keywords

Acid hydrolysis of polysaccharides; Biofine char; Biofine process; Ethyl levulinate; Lignocellulosic fractionation

Indexed keywords

EID: 84870030620     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619849.ch7     Document Type: Chapter

References (56)

1. Szmant, H.H. (1989), Organic Building Blocks of the Chemical Industry. Wiley & Sons, New York.
2. Fitzpatrick, S.W. (1990), Lignocellulose degradation to furfural and levulinic acid: U.S. Patent 4,897,497
3. Fitzpatrick, S.W. (1997), Production of levulinic acid from carbohydrate-containing materials: U.S. Patent 5,608,105
4. McAloon, A., Taylor, F., Yee, W., Ibsen, K. and Wooley, R. (2000), Determining the Cost of Producing Ethanol from Corn Starch and Lignocellulosic Feedstocks, NREL/TP-580-28893. NREL, Golden, CO.
5. Broder, J. D., Harris, R. A. and Ranney, J.T. (2001), Using MSW and industrial residues as ethanol feedstocks. Bi Cycle 42(10): 23-26.
6. Bozell, J. J. (2001), Chemicals and Materials from Renewable Resources. American Chemical Society, Washington DC.
7. Klass, D. L. (1981), Biomass as a nonfossil fuel source. American Chemical Society, Washington DC.
8. Sjostrom, E. (1981), Wood Chemistry: Fundamentals and Applications. Academic Press, Inc., London, UK.
9. Zerbe, J. I. and Baker, A. J. (1987), Investigation of fundamentals of two-stage, dilute sulphuric acid hydrolysis of wood. In: D.L. Klass (eds), Energy from Biomass and Wastes X. Institute of Gas Technology, Chicago, 927-947.
10. Kooherkov, N. A., Bochkov, A. F., Dimitriev, B. A., Usov, A. I., Chizbov, O.S. and Shibaev, Y.N. (1967), Khimiya Uglevodov (The Chemistry of Carbohydrates). Khimiya, Moscow.
11. Timokhin, B.V., Baransky, V. A. and Eliseeva, G. D. (1999), Levulinic acid in organic synthesis. Russian Chemical Reviews 68(1): 73-84.
12. Horvat, J., Klaic, B., Metelko, B. and Sunjic, V. (1985), Mechanism of levulinic acid formation. Tetrahedron 26: 2111-2214.
13. Horvat, J., Klaic, B., Metelko, B. and Sunjic, V. (1986), Mechanism of levulinic acid formation in acid-catalyzed hydrolysis of 2-hydroxymethylfuran and 5-hydroxymethylfuran-2-carbaldehyde. Croat. Chem. Acta 59: 429-438.
14. Leonard, R.H. (1956), Levulinic acid as a basic chemical raw materials. Ind. Eng. Chem. 48(8): 1331-1341.
15. USDA (1971), Bark and its Possible Uses. US Department of Agriculture, Madison, WI.
16. Wiselogel, A. E., Agblevor, F. A., Johnson, D.K., Deutch, S., Fennell, J. A. and Sanderson, M.A. (1996), Compositional changes during storage of large round switchgrass bales. Bioresource Technology 56(1): 103-109.
17. Susott, R. A., DeGroot, W. F. and Shafizadeh, F. (1975), Heat content of natural fuels. J. Fire and Flammability 6: 311-325.
18. Nguyen, Q. (1998), Milestone Completion Report: Evaluation of a Two-Stage Dilute Sulfuric Acid Hydrolysis Process. Internal Report. National Renewable Energy Laboratory, Golden, Colorado.
19. Gregg, D. and Saddler, J.N. (1996), A techno-economic assessment of the pretreatment and fractionation steps of a biomass-to-ethanol process. Appl. Biochem. Biotech. 57/58: 711-726.
20. Beck, M.J. and Strickland, R. C. (1984), Production of ethanol by bioconversion of wood sugars derived from two-stage dilute acid hydrolysis of hardwood. Biomass and Bioenergy 6: 101-110.
21. Cooper (1999), A Renewed Boost for Ethanol. Chemical Engineering 106(2): 35.
22. BioMetics Inc. (1996), Municipal Solid Waste Conversion Project, Final Report, Contract No: 4204-ERTER-ER-96. Biometics Inc., Boston, MA.
23. Donaldson, L. A., Wong, K. K.Y. and Mackie, K. L. (1988), Ultrastructure of steam-exploded wood. Wood Science and Technology 22: 103-114.
24. Oono, T., Saito, S., Shinohara, S. and Takakuwa, K. (1996), Fluxes for electric circuit board soldering and electric circuit boards: Japanese patent 08243787
25. Shimizu, A., Nishio, S., Wada, Y. and Metoki, I. (1996), Photographic processing method for processing silver halide photo graphic light-sensitive material: European patent 704756
26. Adams, P. E., Lange, R. M., Yodice, R., Baker, M.R. and Dietz, J. G. (1998), Intermediates useful for preparing dispersant-viscosity improvers for lubricating oils: European patent 882745
27. Isoda, Y. and Azuma, M. (1996), Preparation of bis(hydroxyaryl)pentanoic acids: Japanese patent 08053390 to Honshu Chemical Ind.
28. Bozell, J. J., Moens, L., Elliott, D.C., Wang, Y., Neuenschwander, G. G., Fitzpatrick, S.W., Bilski, R. J. and Jarnefeld, J. L. (2000), Production of levulinic acid and use as a platform chemical for derived products. Resources, Conservation and Recycling 28: 227-239.
29. Moore, J. A. and Tannahill, T. (2000), Homo- and co-polycarbonates and blends derived from diphenolic acid. High Performance Polymers 13: 305-316.
30. Ring, K.-L., Kaelin, T. and Yoneyama, M. (2001), CEH Report: Tetrahydrofuran. SRI, Menlo Park, CA.
31. Nghiem, N., Davison, B. H., Donnelly, M.I., Tsai, S.-P. and Frye, J.G. (2001), An integrated process for the production of chemicals from biologically derived succinic acid. In: J. J. Bozell (eds), Chemicals and Materials from Renewable Resources. American Chemical Society, Washington DC, 160-173.
32. Gibson, H.D., Laver, W.G. and Neuberger, A. (1958), Initial stages in the biosynthesis of porphyrin. II. The formation of 5-aminolevulinic acid from glycine and succinyl-CoA by particles from chicken erythrocytes. Biochem. J. 70: 71-81.
33. Beale, S. I. and Castelfranco, P. A. (1974), The biosynthesis of delta-aminolevulinic acid in higher plants. II. Formation of 14C-delta-aminolevulinic acid from labelled precursors in greening plant tissues. Plant Physiol. 53: 297.
34. Chen, J., Miller, G.W. and Takemoto, J.Y. (1981), Biosynthesis of δ-aminolevulinic acid in Rhodopseudomonas spaeroides. Arch. Biochem. Biophys. 208: 221-228.
35. Rebeiz, C. A., Montazer-Zouhoor, A., Hopen, H.J. and Wu, S.M. (1984), Photodynamic herbicides: Concept and phenomenology. Enzyme and Microbial Technology 6: 390-401.
36. Rebeiz, C. A., Gut, L. J., Lee, K., Juvik, J. A., Rebeiz, C. C. and Bouton, C. E. (1995), Photodynamics of porphyric insecticides. Crit. Rev. Plant Sci. 14: 329-366.
37. Bedwell, J., McRoberts, A. J., Phillips, D. and Brown, S. G. (1992), Fluorescence distribution and photodynamic effect of ALA-induced PP IX in the DMF rat colonic tumor model. Br. J. Cancer 65: 818-824.
38. MacDonald, S. F. (1974), Methyl 5-bromolevulinate. Can. J. Chem. 52: 3257-3258.
39. Ha, H.-J., Lee, S.-K., Ha, Y.-J. and Park, J.-W. (1994), Selective bromination of ketone. A convenient synthesis of 5-aminolevulinic acid. Synth. Commun. 24: 2557-2562.
40. Lucas, S. V., Loehr, D. A., Meyer, M.aE. and Thomas, J. J. (1993), Exhaust emissions and field trial results of a new, oxygenated, non-petroleum-based, waste-derived, gasoline blending component, 2-methyltetrahydrofuran. Soc. Auto. Eng. Fuels and Lubricants Sect. Mtg., Philadelphia, PA.
41. DoE (1999), 10 CFR Part 490: Alternative Fuel Transportation Program; P-Series Fuels; Final Rule. Office of Energy Efficiency and Renewable Energy, Department of Energy (DOE).
42. Bayan, S. and Beati, E. (1941), Chemica e Industria 23: 432-434.
43. Thomas, J. J. (1986), Biomass Derived Levulinic Acid Derivatives and Their Use as Liquid Fuel Extenders. Biomass Energy Dev. [Proc. South Biomass Energy Res. Conf.], Plenum.
44. Texaco/NYSERDA/Biofine (2000), Ethyl Levulinate D-975 Diesel Additive Test Program, Glenham, NY.
45. Elliott, D. C. (1999), U.S. Patent 5,883,266
46. Huang, C. and Wilson, D. (2000), 91st AOCS Annual Mtg., April 26th, 2000.
47. Erner, W.E. (1982), U.S. Patent 4,364,743
48. Bizzari, S. and Ishikawa, Y. (2001), CEH Report: Formic acid. SRI, Menlo Park, CA.
49. Idriss, H., Lusvardi, V. S. and Barteau, M.A. (1996), Two routes to formaldehyde from formic acid on TiO2(001) surface. Surface Science 348(1/2): 39-48.
50. Gravitis, J., Vedernikov, N., Zandersons, J. and Kokorevics, A. (2001), Furfural and levoglucosan production from deciduous wood and agricultural wastes. In: J. J. Bozell (eds), Chemicals and Materials from Renewable Resources. American Chemical Society, Washington DC, 110-122.
51. Levy, J. and Sakuma, Y. (2001), CEH Report: Furfural. SRI, Menlo Park, CA.
52. Rieche, A. (1964), Outline of Industrial Organic Chemistry. Butterworths, London.
53. Sutton, D., Kelleher, B.P. and Ross, J. R.H. (2001), Review of Literature on Catalysts for Biomass Gasification. Fuel Processing Technology 73(3): 155-173.
54. Bakkerud, P. K., Gol, J. N., Aasberg-Petersen, K. and Dybkjaer, I. (2004), Preferred Synthesis Gas Production Routes for GTL. (eds), Studies in Surface Science and Catalysis. Elsevier, New York, 147: 13-18.
55. Bao, X. and Xu, Y. (2004), Natural Gas Conversion VII, Studies in Surface Science and Catalysis, 147. Elsevier, New York.
56. Seaworthy Systems Inc. (1997), SSI Report #403-01-01.