Heterogeneous Catalysts for Advanced Biofuel Production

  • Vorranutch Itthibenchapong
  • Atthapon Srifa
  • Kajornsak Faungnawakij
Chapter
Part of the Green Chemistry and Sustainable Technology book series (GCST)

Abstract

The triglyceride-based feedstocks and biomass derivatives have been considered promising resources for production of advanced biofuels, namely, green diesel and biojet fuels. Among the series of deoxygenation reactions, hydrodeoxygenation is a majority in the green diesel production when utilizing the group of metal sulfides catalysts, namely, MoS2 with various doping elements. Moreover, decarbonylation is predominant over sulfur-free catalysts including noble metals, e.g., Pd and Pt, and non-precious transition metal, e.g., Ni. The decarboxylation is an interesting pathway due to unconsumed H2 reaction mechanism. As for biojet fuels, the composite of metal/metal sulfides with strong solid acids are promising approaches to catalyze hydroisomerization and cracking reactions of the straight-chain alkanes into the branch ones with proper carbon atoms. Alternatively, the alumina- and zeolite-supported metal catalysts have been extensively developed for the conversion of biomass derivatives into biojet fuels, fuel additives, and biochemical platforms. The research, development, and engineering of novel heterogeneous catalysts could be a key factor for commercialization and strong establishment of the biorefinery and biofuel industries.

Keywords

Advanced biofuels Bio-hydrogenated diesel Biojet Deoxygenation Heterogeneous catalyst 

Notes

Acknowledgment

The authors acknowledge the financial support from the National Nanotechnology Center, NSTDA, Thailand, the Thailand Research Fund (TRF) to V.I. (TRG5880192) and K.F. (RSA5580055), and the National Research Council of Thailand (NRCT) to K.F. This work was also supported by the Collaboration Hubs for International Program (CHIRP) of Strategic International Collaborative Research Program (SICORP), Japan Science and Technology Agency (JST).

References

  1. Agency for Toxic Substances and Disease Registry (ATSDR), U.S. http://www.atsdr.cdc.gov/toxprofiles/tp76-c3.pdf. Accessed 19 Nov 2015
  2. Bezergianni S, Kalogianni A (2009) Hydrocracking of used cooking oil for biofuels production. Bioresour Technol 100:3927–3932CrossRefGoogle Scholar
  3. Bezergianni S, Dimitriadis A, Kalogianni A, Knudsen KG (2011) Toward hydrotreating of waste cooking oil for biodiesel production effect of pressure, H2/oil ratio, and liquid hourly space velocity. Indus Eng Chem Res 50:3874–3879CrossRefGoogle Scholar
  4. Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Integrated catalytic conversion of γ-valerolactone to liquid alkenes for transportation fuels. Science 327:1110–1114CrossRefGoogle Scholar
  5. Botas JA, Serrano DP, García A, de Vicente J, Ramos R (2012) Catalytic conversion of rapeseed oil into raw chemicals and fuels over Ni- and Mo-modified nanocrystalline ZSM-5 zeolite. Catal Today 195:59–70CrossRefGoogle Scholar
  6. Chen L, Zhu Y, Zheng H, Zhang C, Zhang B, Li Y (2011) Aqueous-phase hydrodeoxygenation of carboxylic acids to alcohols or alkanes over supported Ru catalysts. J Mol Catal A Chem 351:217–227CrossRefGoogle Scholar
  7. Chen L, Zhu Y, Zheng H, Zhang C, Li Y (2012) Aqueous-phase hydrodeoxygenation of propanoic acid over the Ru/ZrO2 and Ru–Mo/ZrO2 catalysts. Appl Catal A 411–412:95–104CrossRefGoogle Scholar
  8. Chen N, Gong S, Shirai H, Watanabe T, Qian EW (2013) Effects of Si/Al ratio and Pt loading on Pt/SAPO-11 catalysts in hydroconversion of Jatropha oil. Appl Catal A 466:105–115CrossRefGoogle Scholar
  9. Chen J, Shi H, Li L, Li K (2014) Deoxygenation of methyl laurate as a model compound to hydrocarbons on transition metal phosphide catalysts. Appl Catal B 144:870–884CrossRefGoogle Scholar
  10. Chen F, Li N, Li S, Yang J, Liu F, Wang W, Wang A, Cong Y, Wang X, Zhang T (2015a) Solvent-free synthesis of C9 and C10 branched alkanes with furfural and 3-pentanone from lignocellulose. Catal Commun 59:229–232CrossRefGoogle Scholar
  11. Chen N, Gong S, Qian EW (2015b) Effect of reduction temperature of NiMoO3-x/SAPO-11 on its catalytic activity in hydrodeoxygenation of methyl laurate. Appl Catal B 174–175:253–263CrossRefGoogle Scholar
  12. Choi I-H, Hwang K-R, Han J-S, Lee K-H, Yun JS, Lee J-S (2015) The direct production of jet-fuel from non-edible oil in a single-step process. Fuel 158:98–104CrossRefGoogle Scholar
  13. Do P, Chiappero M, Lobban L, Resasco D (2009) Catalytic deoxygenation of methyl-octanoate and methyl-stearate on Pt/Al2O3. Catal Lett 130:9–18CrossRefGoogle Scholar
  14. Donnis B, Egeberg RG, Blom P, Knudsen KG (2009) Hydroprocessing of bio-oils and oxygenates to hydrocarbons understanding the reaction routes. Top Catal 52:229–240CrossRefGoogle Scholar
  15. Duan J, Han J, Sun H, Chen P, Lou H, Zheng X (2012) Diesel-like hydrocarbons obtained by direct hydrodeoxygenation of sunflower oil over Pd/Al-SBA-15 catalysts. Catal Commun 17:76–80CrossRefGoogle Scholar
  16. Faungnawakij K, Suriye K (2013) Chapter 4 – Current catalytic processes with hybrid materials and composites for heterogeneous catalysis. In: Suib SL (ed) New and future developments in catalysis. Elsevier, Amsterdam, pp 79–104CrossRefGoogle Scholar
  17. Gong S, Shinozaki A, Qian EW (2012a) Role of support in hydrotreatment of jatropha oil over sulfided NiMo catalysts. Indus Eng Chem Res 51:13953–13960CrossRefGoogle Scholar
  18. Gong S, Shinozaki A, Shi M, Qian EW (2012b) Hydrotreating of jatropha oil over alumina based catalysts. Energy Fuels 26:2394–2399CrossRefGoogle Scholar
  19. Guzman A, Torres JE, Prada LP, Nuñez ML (2010) Hydroprocessing of crude palm oil at pilot plant scale. Catal Today 156:38–43CrossRefGoogle Scholar
  20. Hanaoka T, Miyazawa T, Shimura K, Hirata S (2015) Jet fuel synthesis from Fischer–Tropsch product under mild hydrocracking conditions using Pt-loaded catalysts. Chem Eng J 263:178–185CrossRefGoogle Scholar
  21. Hancsók J, Kasza T, Kovács S, Solymosi P, Holló A (2012) Production of bioparaffins by the catalytic hydrogenation of natural triglycerides. J Clean Prod 34:76–81CrossRefGoogle Scholar
  22. Harvey BG, Meylemans HA (2013) 1-Hexene: a renewable C6 platform for full-performance jet and diesel fuels. Green Chem 16:770–776CrossRefGoogle Scholar
  23. Hermida L, Abdullah AZ, Mohamed AR (2015) Deoxygenation of fatty acid to produce diesel-like hydrocarbons: a review of process conditions, reaction kinetics and mechanism. Renew Sust Energ Rev 42:1223–1233CrossRefGoogle Scholar
  24. Huber GW, O’Connor P, Corma A (2007) Processing biomass in conventional oil refineries: production of high quality diesel by hydrotreating vegetable oils in heavy vacuum oil mixtures. Appl Catal A 329:120–129CrossRefGoogle Scholar
  25. Immer JG, Kelly MJ, Lamb HH (2010) Catalytic reaction pathways in liquid-phase deoxygenation of C18 free fatty acids. Appl Catal A 375:134–139CrossRefGoogle Scholar
  26. Jakkula J, Niemi V, Purola VM (2004) Process for producing a hydrocarbon component of biological origin. US Patent 0230085Google Scholar
  27. Kaewmeesri R, Srifa A, Itthibenchapong V, Faungnawakij K (2015) Deoxygenation of waste chicken fats to green diesel over Ni/Al2O3: effect of water and free fatty acid content. Energy Fuel 29:833–840Google Scholar
  28. Kalnes TN, Koers KP, Marker T, Shonnard DR (2009) A technoeconomic and environmental life cycle comparison of green diesel to biodiesel and syndiesel. Environ Prog Sustain Energy 28:111–120CrossRefGoogle Scholar
  29. Kiatkittipong W, Phimsen S, Kiatkittipong K, Wongsakulphasatch S, Laosiripojana N, Assabumrungrat S (2013) Diesel-like hydrocarbon production from hydroprocessing of relevant refining palm oil. Fuel Process Technol 116:16–26CrossRefGoogle Scholar
  30. Kim SK, Brand S, Lee H, Kim Y, Kim J (2013) Production of renewable diesel by hydrotreatment of soybean oil: effect of reaction parameters. Chem Eng J 228:114–123CrossRefGoogle Scholar
  31. Kim SK, Han JY, Lee HS, Yum T, Kim Y, Kim J (2014) Production of renewable diesel via catalytic deoxygenation of natural triglycerides: comprehensive understanding of reaction intermediates and hydrocarbons. Appl Energy 116:199–205CrossRefGoogle Scholar
  32. Kimura T, Imai H, Li X, Sakashita K, Asaoka S, Al-Khattaf SS (2013) Hydroconversion of triglycerides to hydrocarbons over Mo–Ni/γ-Al2O3 catalyst under low hydrogen pressure. Catal Lett 143:1175–1181CrossRefGoogle Scholar
  33. Kordulis C, Bourikas K, Gousi M, Kordouli E, Lycourghiotis A (2016) Development of nickel based catalysts for the transformation of natural triglycerides and related compounds into green diesel: a critical review. Appl Catal B 181:156–196CrossRefGoogle Scholar
  34. Kovács S, Kasza T, Thernesz A, Horváth IW, Hancsók J (2011) Fuel production by hydrotreating of triglycerides on NiMo/Al2O3/F catalyst. Chem Eng J 176–177:237–243CrossRefGoogle Scholar
  35. Krár M, Kovács S, Kalló D, Hancsók J (2010) Fuel purpose hydrotreating of sunflower oil on CoMo/Al2O3 catalyst. Bioresour Technol 101:9287–9293CrossRefGoogle Scholar
  36. Kubička D, Kaluža L (2010) Deoxygenation of vegetable oils over sulfided Ni, Mo and NiMo catalysts. Appl Catal 372:199–208CrossRefGoogle Scholar
  37. Kubička D, Tukač V (2013) Chapter Three – Hydrotreating of triglyceride-based feedstocks in refineries. In: Dmitry Yu M (ed) Advances in chemical engineering. Academic Press, Burlington, pp 141–194Google Scholar
  38. Kubička D, Horáček J, Setnička M, Bulánek R, Zukal A, Kubičková I (2014) Effect of support-active phase interactions on the catalyst activity and selectivity in deoxygenation of triglycerides. Appl Catal B 145:101–107CrossRefGoogle Scholar
  39. Kubičková I, Snåre M, Eränen K, Mäki-Arvela P, Murzin DY (2005) Hydrocarbons for diesel fuel via decarboxylation of vegetable oils. Catal Today 106:197–200CrossRefGoogle Scholar
  40. Kumar P, Yenumala SR, Maity SK, Shee D (2014) Kinetics of hydrodeoxygenation of stearic acid using supported nickel catalysts: effects of supports. Appl Catal A 471:28–38CrossRefGoogle Scholar
  41. Lestari S, Mäki-Arvela P, Eränen K, Beltramini J, Max Lu GQ, Murzin DY (2009) Diesel-like hydrocarbons from catalytic deoxygenation of stearic acid over supported Pd nanoparticles on SBA-15 catalysts. Catal Lett 134:250–257CrossRefGoogle Scholar
  42. Li S, Li N, Li G, Li L, Wang A, Cong Y, Wang X, Xu G, Zhang T (2015a) Protonated titanate nanotubes as a highly active catalyst for the synthesis of renewable diesel and jet fuel range alkanes. Appl Catal B 170–171:124–134CrossRefGoogle Scholar
  43. Li T, Cheng J, Huang R, Zhou J, Cen K (2015b) Conversion of waste cooking oil to jet biofuel with nickel-based mesoporous zeolite Y catalyst. Bioresour Technol 197:289–294CrossRefGoogle Scholar
  44. Liu Y, Sotelo-Boyás R, Murata K, Minowa T, Sakanishi K (2011) Hydrotreatment of vegetable oils to produce bio-hydrogenated diesel and liquefied petroleum gas fuel over catalysts containing sulfided Ni–Mo and solid acids. Energy Fuels 25:4675–4685CrossRefGoogle Scholar
  45. Liu G, Yan B, Chen G (2013a) Technical review on jet fuel production. Renew Sust Energy Rev 25:59–70CrossRefGoogle Scholar
  46. Liu Q, Zuo H, Wang T, Ma L, Zhang Q (2013b) One-step hydrodeoxygenation of palm oil to isomerized hydrocarbon fuels over Ni supported on nano-sized SAPO-11 catalysts. Appl Catal A 468:68–74CrossRefGoogle Scholar
  47. Liu Q, Bie Y, Qiu S, Zhang Q, Sainio J, Wang T, Ma L, Lehtonen J (2014) Hydrogenolysis of methyl heptanoate over Co based catalysts: mediation of support property on activity and product distribution. Appl Catal B 147:236–245CrossRefGoogle Scholar
  48. Liu S, Zhu Q, Guan Q, He L, Li W (2015) Bio-aviation fuel production from hydroprocessing castor oil promoted by the nickel-based bifunctional catalysts. Bioresour Technol 183:93–100CrossRefGoogle Scholar
  49. Lown AL, Peereboom L, Mueller SA, Anderson JE, Miller DJ, Lira CT (2014) Cold flow properties for blends of biofuels with diesel and jet fuels. Fuel 117:544–551CrossRefGoogle Scholar
  50. Maia AJ, Louis B, Lam YL, Pereira MM (2010) Ni-ZSM-5 catalysts: detailed characterization of metal sites for proper catalyst design. J Catal 269:103–109CrossRefGoogle Scholar
  51. Mäki-Arvela P, Rozmysłowicz B, Lestari S, Simakova O, Eränen K, Salmi T, Murzin DY (2011) Catalytic deoxygenation of tall oil fatty acid over palladium supported on mesoporous carbon. Energy Fuels 25:2815–2825CrossRefGoogle Scholar
  52. Mériaudeau P, Tuan VA, Sapaly G, Nghiem VT, Naccache C (1999) Pore size and crystal size effects on the selective hydroisomerisation of C8 paraffins over Pt–Pd/SAPO-11, Pt–Pd/SAPO-41 bifunctional catalysts. Catal Today 49:285–292CrossRefGoogle Scholar
  53. Murata K, Liu Y, Inaba M, Takahara I (2010) Production of synthetic diesel by hydrotreatment of jatropha oils using Pt−Re/H-ZSM-5 catalyst. Energy Fuels 24:2404–2409CrossRefGoogle Scholar
  54. Musselwhite N, Na K, Sabyrov K, Alayoglu S, Somorjai GA (2015) Mesoporous aluminosilicate catalysts for the selective isomerization of n-Hexane: the roles of surface acidity and platinum metal. J Am Chem Soc 137:10231–10237CrossRefGoogle Scholar
  55. Ochoa-Hernández C, Yang Y, Pizarro P, O’Shea VA, Coronado JM, Serrano DP (2013) Hydrocarbons production through hydrotreating of methyl esters over Ni and Co supported on SBA-15 and Al-SBA-15. Catal Today 210:81–88CrossRefGoogle Scholar
  56. Olcay H, Subrahmanyam AV, Xing R, Lajoie J, Dumesic JA, Huber JW (2013) Production of renewable petroleum refinery diesel and jet fuel feedstocks from hemicellulose sugar streams. Energy Environ Sci 6:205–216CrossRefGoogle Scholar
  57. Onyestyák G, Harnos S, Szegedi Á, Kalló D (2012) Sunflower oil to green diesel over Raney-type Ni-catalyst. Fuel 102:282–288CrossRefGoogle Scholar
  58. Peng B (2012) Transformation of triglycerides and fatty acids into biofuels with sulfur-free catalysts. Technische Universität MünchenGoogle Scholar
  59. Peng B, Yao Y, Zhao C, Lercher JA (2012a) Towards quantitative conversion of microalgae oil to diesel-range alkanes with bifunctional catalysts. Angew Chem Int Ed 51:2072–2075CrossRefGoogle Scholar
  60. Peng B, Yuan X, Zhao C, Lercher JA (2012b) Stabilizing catalytic pathways via redundancy: selective reduction of microalgae oil to alkanes. J Am Chem Soc 134:9400–9405CrossRefGoogle Scholar
  61. Peng B, Zhao C, Kasakov S, Foraita S, Lercher JA (2013) Manipulating catalytic pathways: deoxygenation of palmitic acid on multifunctional catalysts. Chemistry 19:4732–4741CrossRefGoogle Scholar
  62. Pholjaroen B, Li N, Yang J, Li G, Wang W, Wang A, Cong Y, Wang X, Zhang T (2014) Production of renewable jet fuel range branched alkanes with xylose and methyl isobutyl ketone. Ind Eng Chem Res 53:13618–13625CrossRefGoogle Scholar
  63. Prasomsri T, Shetty M, Murugappan K, Roman-Leshkov Y (2014) Insights into the catalytic activity and surface modification of MoO3 during the hydrodeoxygenation of lignin-derived model compounds into aromatic hydrocarbons under low hydrogen pressures. Energy Environ Sci 7:2660–2669CrossRefGoogle Scholar
  64. Priecel P, Kubička D, Čapek L, Bastl Z, Ryšánek P (2011) The role of Ni species in the deoxygenation of rapeseed oil over NiMo-alumina catalysts. Appl Catal A 397:127–137CrossRefGoogle Scholar
  65. Rabaev M, Landau MV, Vidruk-Nehemya R, Koukouliev V, Zarchin R, Herskowitz M (2015) Conversion of vegetable oils on Pt/Al2O3/SAPO-11 to diesel and jet fuels containing aromatics. Fuel 161:287–294CrossRefGoogle Scholar
  66. Santillan-Jimenez E, Morgan T, Lacny J, Mohapatra S, Crocker M (2013a) Catalytic deoxygenation of triglycerides and fatty acids to hydrocarbons over carbon-supported nickel. Fuel 103:1010–1017CrossRefGoogle Scholar
  67. Santillan-Jimenez E, Morgan T, Shoup J, Harman-Ware AE, Crocker M (2013b) Catalytic deoxygenation of triglycerides and fatty acids to hydrocarbons over Ni–Al layered double hydroxide. Catal Today 237:136–144CrossRefGoogle Scholar
  68. Sattler JJHB, Ruiz-Martinez J, Santillan-Jimenez E, Weckhuysen BM (2014) Catalytic dehydrogenation of light alkanes on metals and metal oxides. Chem Rev 114:10613–10653CrossRefGoogle Scholar
  69. Satyarthi JK, Chiranjeevi T, Gokak DT, Viswanathan PS (2013) An overview of catalytic conversion of vegetable oils/fats into middle distillates. Catal Sci Technol 3:70–80CrossRefGoogle Scholar
  70. Simakova I, Simakova O, Mäki-Arvela P, Simakov A, Estrada M, Murzin DY (2009) Deoxygenation of palmitic and stearic acid over supported Pd catalysts: effect of metal dispersion. Appl Catal A 355:100–108CrossRefGoogle Scholar
  71. Snåre M, Kubičková I, Mäki-Arvela P, Eränen K, Murzin DY (2006) Heterogeneous catalytic deoxygenation of stearic acid for production of biodiesel. Ind Eng Chem Res 45:6875CrossRefGoogle Scholar
  72. Srifa A, Faungnawakij K, Itthibenchapong V, Viriya-empikul N, Charinpanitkul T, Assabumrungrat S (2014) Production of bio-hydrogenated diesel by catalytic hydrotreating of palm oil over NiMoS2/γ-Al2O3 catalyst. Bioresour Technol 158:81–90CrossRefGoogle Scholar
  73. Srifa A, Faungnawakij K, Itthibenchapong V, Assabumrungrat S (2015a) Roles of monometallic catalysts in hydrodeoxygenation of palm oil to green diesel. Chem Eng J 278:249–258CrossRefGoogle Scholar
  74. Srifa A, Viriya-empikul N, Assabumrungrat S, Faungnawakij K (2015b) Catalytic behaviors of Ni/γ-Al2O3 and Co/γ-Al2O3 during the hydrodeoxygenation of palm oil. Catal Sci Technol 5:3693–3705CrossRefGoogle Scholar
  75. Veriansyah B, Han JY, Kim SK, Hong SA, Kim YJ, Lim JS, Shu YW, Oh SG, Kim J (2012) Production of renewable diesel by hydroprocessing of soybean oil: effect of catalysts. Fuel 94:578–585CrossRefGoogle Scholar
  76. Verma D, Kumar R, Rana BS, Sinha AK (2011) Aviation fuel production from lipids by a single-step route using hierarchical mesoporous zeolites. Energy Environ Sci 4:1667–1671CrossRefGoogle Scholar
  77. Verma D, Rana BS, Kumar R, Sibi MG, Sinha AK (2015) Diesel and aviation kerosene with desired aromatics from hydroprocessing of jatropha oil over hydrogenation catalysts supported on hierarchical mesoporous SAPO-11. Appl Catal A 490:108–116CrossRefGoogle Scholar
  78. Wang C, Tian Z, Wang L, Xu R, Liu Q, Qu W, Ma H, Wang B (2012) One-step hydrotreatment of vegetable oil to produce high quality diesel-range alkanes. ChemSusChem 5:1974–1983CrossRefGoogle Scholar
  79. Wright ME, Harvey BG, Quintana RL (2008) Highly efficient zirconium-catalyzed batch conversion of 1-butene: a new route to jet fuels. Energy Fuels 22:3299–3302CrossRefGoogle Scholar
  80. Yan Q, Yu F, Liu J, Street J, Gao J, Cai Z, Zhang J (2013) Catalytic conversion wood syngas to synthetic aviation turbine fuels over a multifunctional catalyst. Bioresour Technol 127:281–290CrossRefGoogle Scholar
  81. Yang J, Li N, Li S, Wang W, Li L, Wang A, Wang X, Cong Y, Zhang T (2014) Synthesis of diesel and jet fuel range alkanes with furfural and ketones from lignocellulose under solvent free conditions. Green Chem 16:4879–4884CrossRefGoogle Scholar
  82. Yang L, Tate KL, Jasinski JB, Carreon MA (2015) Decarboxylation of oleic acid to heptadecane over Pt supported on zeolite 5A beads. ACS Catal 5:6497–6502CrossRefGoogle Scholar
  83. Zhang C-H, Yang Y, Teng B-T, Li T-Z, Zheng H-Y, Xiang H-W, Li Y-W (2006) Study of an iron-manganese Fischer–Tropsch synthesis catalyst promoted with copper. J Catal 237:405–415CrossRefGoogle Scholar
  84. Zhang X, Lei H, Zhu L, Wei Y, Liu Y, Yadavalli G, Yan D, Wu J, Chen S (2015) Production of renewable jet fuel range alkanes and aromatics via integrated catalytic processes of intact biomass. Fuel 160:375–385CrossRefGoogle Scholar
  85. Zhao C, Brück T, Lercher JA (2013) Catalytic deoxygenation of microalgae oil to green hydrocarbons. Green Chem 15:1720–1739CrossRefGoogle Scholar
  86. Zuo H, Liu Q, Wang T, Ma L, Zhang Q, Zhang Q (2012) Hydrodeoxygenation of methyl palmitate over supported ni catalysts for diesel-like fuel production. Energy Fuels 26:3747–3755CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2017

Authors and Affiliations

  • Vorranutch Itthibenchapong
    • 1
  • Atthapon Srifa
    • 1
  • Kajornsak Faungnawakij
    • 1
  1. 1.National Nanotechnology Center (NANOTEC)National Science and Technology Development Agency (NSTDA)Khlong LuangThailand

Personalised recommendations