Synthesis of biodiesel via acid catalysis

Industrial and Engineering Chemistry Research

Volumn 44, Issue 14, 2005, Pages 5353-5363

  Lotero, Edgar ^a   Liu, Yijun ^a   Lopez, Dora E ^a   Suwannakarn, Kaewta ^a   Bruce, David A ^a   Goodwin Jr , James G ^a  

^a South   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYSIS; BIODIESEL; FREE FATTY ACIDS (FFA); REACTION TEMPERATURES;

CATALYSIS; COST EFFECTIVENESS; ENVIRONMENTAL PROTECTION; ESTERIFICATION; FATTY ACIDS; FEEDSTOCKS; MOLECULAR WEIGHT; PURIFICATION; SYNTHESIS (CHEMICAL);

SYNTHETIC FUELS;

CATALYSIS;

EID: 22944448048     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie049157g     Document Type: Article

References (67)

1. Kinast, J. A.; Tyson, K. S. Production of biodiesel from multiple feedstocks and properties of biodiesel and biodiesel/diesel blends. Final report; NREL: Golden, CO, 2003.
2. Ma, F. R.; Hanna, M. A. Biodiesel production: a review. Bioresour. Technol. 1999, 70, 1-15.
3. Haas, M. J. The interplay between feedstock quality and esterification technology in biodiesel production. Lipid Technol. 2004, 16, 7-11.
4. Talley, P. Biodiesel. Render 2004, (Sept).
5. Graboski, M. S.; McCormick, R. L. Combustion of fat and vegetable oil derived fuels in diesel engines. Prog. Energy Combust. Sci. 1998, 24, 125-164.
6. Zappi, M.; Hernandez, R.; Sparks, D.; Horne, J.; Brough, M.; Arora, S. M.; Motsenbocker, W. D. A review of the engineering aspects of the biodiesel industry; Mississippi Biomass Council: Jackson, MS, August 2003, 2003; p 71.
7. Canakci, M.; Van Gerpen, J. Biodiesel production via acid catalysis. Trans. ASAE 1999, 42, 1203-1210.
8. Canakci, M.; Van Gerpen, J. A pilot plant to produce biodiesel from high free fatty acid feedstocks. Trans. ASAE 2003, 46, 945-954.
9. Canakci, M.; Van Gerpen, J. Biodiesel production from oils and fats with high free fatty acids. Trans. ASAE 2001, 44, 1429-1436.
10. Tyson, K. S. Biodiesel, handling and use guidelines; NREL: Golden CO, September, 2001; p 22.
11. Noureddini, H. System and process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit. U.S. Patent 6174501, January 16, 2001.
12. Srivastava, A.; Prasad, R. Triglycerides-based diesel fuels. Renewable Sustainable Energy Rev. 2000, 4, 111-133.
13. Zhang, Y.; Dube, M. A.; McLean, D. D.; Kates, M. Biodiesel production from waste cooking oil: 1. Process design and technological assessment. Bioresour. Technol. 2003, 59, 1-16.
14. Zhang, Y.; Dube, M. A.; McLean, D. D.; Kates, M. Biodiesel production from waste cooking oil: 2. Economic assessment and sensitivity analysis. Bioresour. Technol. 2003, 90, 229-240.
15. Liu, K. S. Preparation of Fatty-Acid Methyl Esters for Gas-Chromatographic Analysis of Lipids in Biological-Materials. J. Am. Oil Chem Soc. 1994, 71, 1179-1187.
16. Freedman, B.; Butterfield, R. O.; Pryde, E. H. Transesterification kinetics of soybean oil. J. Am. Oil Chem. Soc. 1986, 63, 1375-1380.
17. Crabbe, E.; Nolasco-Hipolito, C.; Kobayashi, G.; Sonomoto, K.; Ishizaki, A. Biodiesel production from crude palm oil and evaluation of butanol extraction and fuel properties. Process Biochem. 2001, 37, 65-71.
18. Demirbas, A. Biodiesel fuels from vegetable oils via catalytic and noncatalytic supercritical alcohol transesterifications and other methods: a survey. Energy Convers. Manage. 2003, 44, 2093-2109.
19. Fukuda, H.; Kondo, A.; Noda, H. Biodiesel fuel production by transesterification of oils. J. Biosci. Bioeng. 2001, 92, 405-416.
20. Nye, M. J.; Willianson, T. W.; Deshpande, S.; Schrader, J. H.; Snively, W. H.; Yurkewich, T. P.; Frech, C. R. Conversion of used frying oil to diesel fuel by transesterification: preliminary test. J. Am. Oil Chem. Soc. 1983, 60, 1598-1601.
21. Freedman, B.; Pryde, E. H.; T. L., M. Variables affecting the yields of fatty esters from transesterified vegetable oils. J. Am. Oil Chem. Soc. 1984, 61, 1638-1643.
22. Khan, A. K. Research into biodiesel kinetics & catalyst development. University of Queensland, Brisbane, Queensland, 2002.
23. Formo, M. W. Ester reactions of fatty materials. J. Am. Oil Chem Soc. 1954, 31, (11), 548-559.
24. Keyes, D. B. Esterification processes and equipment. Ind. Eng. Chem. 1932, 24 (10), 1096-1103.
25. Kusdiana, D.; Saka, S. Effects of water on biodiesel fuel production by supercritical methanol treatment. Bioresour. Technol. 2004, 91, 289-295.
26. Sridharan, R.; Mathai, I. M. Transesterification reactions. Sci. Ind. Resour. 1974, 33, 178-187.
27. Boocock, D. G. B.; Konar, S. K.; Mao, V.; Sidi, H. Fast one-phase oil-rich process for the preparation of vegetable oil methyl esters. Biomass Bioenerg. 1996, 11, 43-50.
28. Boocock, D. G. V. Single-phase process for production of fatty acid methyl esters from mixtures of triglycerides and fatty acids. U.S. Patent 6642399, November 4, 2003.
29. Rived, F.; Canals, I.; Bosch, E.; Roses, M. Acidity in methanol-water. Anal. Chim. Acta 2001, 439 (2), 315-333.
30. Hoydonckx, H. E.; De Vos, D. E.; Chavan, S. A.; Jacobs, P. A. Esterification and transesterification of renewable chemicals. Top. Catal. 2004, 27, 83-96.
31. Sonntag, V. O. V. Esterification and interesterification. J. Am. Oil Chem Soc. 1979, 56, 751A-754A.
32. Mittelbach, M.; Silberholz, A.; Koncar, M. In Novel aspects concerning acid-catalyzed alcoholysis of triglycerides, Oils-Fats-Lipids 1995, Proceedings of the 21st World Congress of the International Society for Fats Research, The Hague, October 1995, 1996; 1996; pp 497-499.
33. Kaita, J.; Mimura, T.; Fukuoda, N.; Hattori, Y. Catalysts for transesterification. U.S. Patent 6407269, June 18, 2002.
34. 2. Synth. Commun. 1999, 29, 513-520.
35. Vicente, G.; Coteron, A.; Martinez, M.; Aracil, J. Application of the factorial design of experiments and response surface methodology to optimize biodiesel production. Ind. Crops Products 1998, 8, 29-35.
36. Madje, B. R.; Patil, P. T.; Shindalkar, S. S.; Benjamin, S. B.; Shingare, M. S.; Dongare, M. K. Facile transesterification of beta-ketoesters under solvent-free condition using borate zirconia solid acid catalyst. Catal. Commun. 2004, 5, 353-357.
37. Balaji, B. S.; Chanda, B. M. Simple and high yielding syntheses of beta-ketoesters catalysed by zeolites. Tetrahedron 1998, 54, 13237-13252.
38. Chavan, S. P.; Subbarao, Y. T.; Dantale, S. W.; Sivappa, R. Transesterification of ketoesters using Amberlyst-15. Synth. Commun. 2001, 31, 289-294.
39. Bandgar, B. P.; Uppalla, L. S.; Sadavarte, V. S. Envirocat EPZG and natural clay as efficient catalysts for transesterification of beta-keto esters. Green Chem. 2001, 3, 39-41.
40. Ponde, D. E.; Deshpande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. Selective catalytic transesterification, transthiolesterification, and protection of carbonyl compounds over natural kaolinitic clay. J. Org. Chem. 1998, 63, 1058-1063.
41. 2) as efficient catalyst in facile transesterification of ketoesters. Tetrahedron Lett. 1996, 37, 233-236.
42. Sasidharan, M.; Kumar, R. Transesterification over various zeolites under liquid-phase conditions. J. Mol. Catal., A: Chem. 2004, 210, 93-98.
43. Chen, X.; Xu, Z.; Okuhara, T. Liquid-phase esterification of acrylic acid with 1-butanol catalyzed by solid acid catalysts. Appl. Catal, A 1999, 180, 261-269.
44. Heidekum, A.; Harmer, M. A.; Hoelderich, W. F. Addition of carboxylic acids to cyclic olefins catalyzed by strong acidic ion-exchange resins. J. Catal. 1999, 181, 217-222.
45. Zhang, Z. Y.; Hidajat, K.; Ray, A. K. Determination of adsorption and kinetic parameters for methyl tert-butyl ether synthesis from tert-butyl alcohol and methanol. J. Catal. 2001, 200, 209-221.
46. Corma, A.; Garcia, H. Organic reactions catalyzed over solid acids. Catal. Today 1997, 38, 257-308.
47. Corma, A.; Rodriguez, M.; Sanchez, N.; Aracil, J. Process for the selective production of monoesters of diols and triols using zeolitic catalysts. WO9413617, 1994.
48. Perez-Pariente, J.; Diaz, I.; Mohino, F.; Sastre, E. Selective synthesis of fatty monoglycerides by using functionalised mesoporous catalysts. Appl. Catal., A 2003, 254, 173-188.
49. Verhoef, M. J.; Kooyman, P. J.; Peters, J. A.; van Bekkum, H. A study on the stability of MCM-41-supported heteropoly acids under liquid- and gas-phase esterification conditions. Microporous Mesoporous Mater. 1999, 27, 365-371.
50. Mbaraka, I. K.; Radu, D. R.; Lin, V. S. Y.; Shanks, B. H. Organosulfonic acid-functionalized mesoporous silicas for the esterification of fatty acid. J. Catal. 2003, 219, 329-336.
51. Yadav, G. D.; Nair, J. J. Sulfated zirconia and its modified versions as promising catalysts for industrial processes. Microporous Mesoporous Mater. 1999, 33, 1-48.
52. Omota, F.; Dimian, A. C.; Bliek, A. Fatty acid esterification by reactive distillation: Part 2 - kinetics-based design for sulphated zirconia catalysts. Chem. Eng. Sci. 2003, 58, 3175-3185.
53. Yadav, G. D.; Murkute, A. D. Preparation of a novel catalyst UDCaT-5: enhancement in activity of acid-treated zirconia-effect of treatment with chlorosulfonic acid vis-à-vis sulfuric acid. J. Catal. 2004, 224, 218-223.
54. Furuta, S.; Matsuhashi, H.; Arata, K. Catalytic action of sulfated tin oxide for etherification and esterification in comparison with sulfated zirconia. Appl. Catal., A 2004, 269, 187-191.
55. Matsuhashi, H.; Miyazaki, H.; Kawamura, Y.; Nakamura, H.; Arata, K Preparation of a solid superacid of sulfated tin oxide with acidity higher than that of sulfated zirconia and its applications to aldol condensation and benzoylation. Chem. Mater. 2001, 13, 3038-3042.
56. Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Diphenylammonium triflate (DPAT): efficient catalyst for esterification of carboxylic acids and for transesterification of carboxylic esters with newly equimolar amounts of alcohols. Tetrahedron Lett. 2000, 41, 5249-5252.
57. Ishihara, K.; Nakayama, M.; Ohara, S.; Yamamoto, H. Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts. Tetrahedron 2002, 58, 8179-8188.
58. Kesling, J. H. S.; Karas, L. J.; Liotta, J. F. J. Diesel Fuel U.S. Patent 5308365, May 3, 1994.
59. Goodwin, J. G.; Natesakhawat, S.; Nikolopoulos, A. A.; Kim, S. Y. Etherification on zeolites: MTBE synthesis. Catal. Rev.Sci. Eng. 2002, 44, 287-320.
60. Goodwin, J. G.; Bruce, D. A.; Lotero, E.; Suwannakarn, K.; Lopez, D. E. Heterogeneous Catalyst Development for Biodiesel Synthesis; Clemson University: Clemson, SC, October 2004; p 40.
61. Energy Information Administration Gasoline and Diesel Fuel Update.
62. Roadmap for biomass technologies in the United States; USDA, 2002.
63. Goering, C. E.; Schwab, A. W.; Dangherty, M. J.; Pryde, E. H.; Heakin, A. J. Fuel properties of eleven oils. Trans. ASAE 1982, 25, 1472-1483.
64. Aranda, F.; Gomez-Alonso, S.; del Alamo, R. M. R.; Salvador, M. D.; Fregapane, G. Triglyceride, total and 2-position fatty acid composition of Cornicabra virgin olive oil: Comparison with other Spanish cultivars. Food Chem. 2004, 86, 485-492.
65. Engel, J. J.; Smith, J. W.; Unruh, J. A.; Goodband, R. D.; O'Quinn, P. R.; Tokach, M. D.; Nelssen, J. L. Effects of choice white grease or poultry fat on growth performance, carcass leanness, and meat quality characteristics of growing-finishing pigs. J. Anim. Sci. 2001, 79, 1491-1501.
66. Paleari, M. A.; Moretti, V. M.; Bersani, C.; Beretta, G.; Mentasti, T. Characterisation of a lard cured with spices and aromatic herbs. Meat Sci. 2004, 67, 549-557.
67. Zheng, D. N.; Hanna, M. A. Preparation and properties of methyl esters of beef tallow. Bioresour. Technol. 1996, 57, 137-142.