Renewable fuels via catalytic hydrodeoxygenation of lipid-based feedstocks

Energy security concerns have led to the search for alternative and renewable energy resources. Biomass with high lipid content is an attractive feedstock for producing renewable fuels. Biomass-derived fats and oils can be readily converted into biodiesel via the well-studied transesterification process. However, owing to the alcohol component of biodiesel, which contains oxygen, it cannot serve as a fully-fledged replacement for conventional petrodiesel. In this respect, renewable diesel obtained via catalytic hydrodeoxygenation (HDO) of lipid-based feedstocks is a more attractive and fungible option. This process makes it possible to produce fuels with the chemical composition indistinguishable from that of petroleum-derived products. Since all kinds of biomass have high oxygen content, comprehensive research of the catalytic HDO process arouses great interest. This article aims to review state-of-the-art studies related to the catalytic HDO of lipid-based feedstocks from the last decade. The suitability of microalgae as a feedstock for renewable fuel production, as well as the possible advantages of processing lipid-based feedstocks using aqueous HDO, are also addressed in this review.

[1]  P. Spolaore,et al.  Commercial applications of microalgae. , 2006, Journal of bioscience and bioengineering.

[2]  S. Eijsbouts,et al.  How a 70-year-old catalytic refinery process is still ever dependent on innovation , 2008 .

[3]  B. F. Daubert,et al.  The Partial Hydrogenation of Triolein , 1950 .

[4]  Nikos G. Papayannakos,et al.  Catalytic hydroprocessing of cottonseed oil in petroleum diesel mixtures for production of renewable diesel , 2009 .

[5]  Bernard Delmon,et al.  Influence of the Support of CoMo Sulfide Catalysts and of the Addition of Potassium and Platinum on the Catalytic Performances for the Hydrodeoxygenation of Carbonyl, Carboxyl, and Guaiacol-Type Molecules , 1995 .

[6]  Spyros Voutetakis,et al.  Catalytic Hydrocracking of Fresh and Used Cooking Oil , 2009 .

[7]  W. F. Maier,et al.  HYDROGENOLYSIS. IV. GAS-PHASE DECARBOXYLATION OF CARBOXYLIC ACIDS , 1982 .

[8]  A. Dalai,et al.  Preparation and characterization of bio-diesels from various bio-oils. , 2001, Bioresource technology.

[9]  D. L. Klass,et al.  Energy from Biomass and Wastes XI. , 1988 .

[10]  Bernard Delmon,et al.  CoMo/carbon hydrodeoxygenation catalysts: influence of the hydrogen sulfide partial pressure and of the sulfidation temperature , 2001 .

[11]  Bernard Delmon,et al.  Influence of Water in the Deactivation of a Sulfided Nimo Gamma-al2o3 Catalyst During Hydrodeoxygenation , 1994 .

[12]  D. Boocock,et al.  Pathway for the Catalytic Conversion of Carboxylic Acids to Hydrocarbons over Activated Alumina , 1995 .

[13]  Razif Harun,et al.  Bioprocess Engineering Aspects of Biodiesel and Bioethanol Production from Microalgae , 2013 .

[14]  Marker,et al.  Opportunities for Biorenewables in Oil Refineries , 2005 .

[15]  Mark Stumborg,et al.  Hydroprocessed vegetable oils for diesel fuel improvement , 1996 .

[16]  Y. Chisti.  Biodiesel from microalgae beats bioethanol. , 2008, Trends in biotechnology.

[17]  A. Guzmán,et al.  Hydroprocessing of crude palm oil at pilot plant scale , 2010 .

[18]  T. Brill,et al.  Spectroscopy of Hydrothermal Reactions. 10. Evidence of Wall Effects in Decarboxylation Kinetics of 1.00 m HCO2X (X = H, Na) at 280−330 °C and 275 bar , 1998 .

[19]  Avelino Corma,et al.  Processing biomass in conventional oil refineries: Production of high quality diesel by hydrotreating vegetable oils in heavy vacuum oil mixtures , 2007 .

[20]  Jürgen Krahl,et al.  The Biodiesel Handbook , 2005 .

[21]  P. Nunes,et al.  Hydrocraquage sous pression d'une huile de soja : procédé d'étude et allure générale de la transformation , 1986 .

[22]  Ryuichi Matsuno,et al.  Solubility of Saturated Fatty Acids in Water at Elevated Temperatures , 2002, Bioscience, biotechnology, and biochemistry.

[23]  David Kubička,et al.  Fuel properties of hydroprocessed rapeseed oil , 2010 .

[24]  Bryce J. Stokes,et al.  Biomass as Feedstock for A Bioenergy and Bioproducts Industry: The Technical Feasibility of a Billion-Ton Annual Supply , 2005 .

[25]  David Kubička,et al.  Deoxygenation of vegetable oils over sulfided Ni, Mo and NiMo catalysts , 2010 .

[26]  T. Minowa,et al.  A novel microalgal system for energy production with nitrogen cycling , 1999 .

[27]  Q. Zhang,et al.  A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis. , 2012, Bioresource technology.

[28]  B. N. Dickinson,et al.  Oxygen Removal from Water by Ammine Exchange Resins , 1949 .

[29]  William L. Roberts,et al.  Hydrocarbon fuels from vegetable oils via hydrolysis and thermo-catalytic decarboxylation , 2012 .

[30]  Sergey V. Churakov,et al.  Size and topology of molecular clusters in supercritical water: a molecular dynamics simulation , 1999 .

[31]  J. Benemann,et al.  Look Back at the U.S. Department of Energy's Aquatic Species Program: Biodiesel from Algae; Close-Out Report , 1998 .

[32]  Yizhak Marcus,et al.  On transport properties of hot liquid and supercritical water and their relationship to the hydrogen bonding , 1999 .

[33]  Toru Iida,et al.  Decomposition of a long chain saturated fatty acid with some additives in hot compressed water , 2006 .

[34]  Jeno Hancsók,et al.  Fuel purpose hydrotreating of sunflower oil on CoMo/Al2O3 catalyst. , 2010, Bioresource technology.

[35]  Y. Chisti.  Biodiesel from microalgae. , 2007, Biotechnology advances.

[36]  M. P. Dorado,et al.  The Ideal Vegetable Oil-based Biodiesel Composition: A Review of Social, Economical and Technical Implications , 2009 .

[37]  Rekha S. Singhal,et al.  Supercritical CO2 extraction of γ-linolenic acid (GLA) from Spirulina platensis ARM 740 using response surface methodology , 2008 .

[38]  Naděžda Žilková,et al.  Transformation of Vegetable Oils into Hydrocarbons over Mesoporous-Alumina-Supported CoMo Catalysts , 2009 .

[39]  Delanie Lamprecht,et al.  Fischer-Tropsch Fuel for Use by the U.S. Military as Battlefield-Use Fuel of the Future , 2007 .

[40]  Gabriele Centi,et al.  Catalysis for renewables : from feedstock to energy production , 2008 .

[41]  Arief Widjaja,et al.  Study of increasing lipid production from fresh water microalgae Chlorella vulgaris , 2009 .

[42]  Bernard Delmon,et al.  Study of the Hydrodeoxygenation of Carbonyl, Carboxylic and Guaiacyl Groups Over Sulfided Como/gamma-al2o3 and Nimo/gamma-al2o3 Catalysts .1. Catalytic Reaction Schemes , 1994 .

[43]  D. Boocock,et al.  Pathways for the deoxygenation of triglycerides to aliphatic hydrocarbons over activated alumina , 1995 .

[44]  Gerhard Knothe,et al.  Biodiesel and renewable diesel: A comparison , 2010 .

[45]  A. Corma,et al.  Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. , 2006, Chemical reviews.

[46]  S. M. Barrett,et al.  Changes in the lipid composition and maximisation of the polyunsaturated fatty acid content of three microalgae grown in mass culture , 1993, Journal of Applied Phycology.

[47]  K. Knudsen,et al.  Hydroprocessing of Bio-Oils and Oxygenates to Hydrocarbons. Understanding the Reaction Routes , 2009 .

[48]  Kari Eränen,et al.  Catalytic deoxygenation of unsaturated renewable feedstocks for production of diesel fuel hydrocarbons , 2008 .

[49]  Paul von Ragué Schleyer,et al.  Hydrogenolysis, IV. Gas phase decarboxylation of carboxylic acids , 1982 .

[50]  E. Ibáñez,et al.  Sub- and supercritical fluid extraction of functional ingredients from different natural sources: Plants, food-by-products, algae and microalgae: A review , 2006 .

[51]  Birgit Kamm,et al.  Biorefineries – Industrial Processes and Products , 2005 .

[52]  J. Dumesic,et al.  Renewable hydrogen by aqueous-phase reforming of glucose. , 2004, Chemical communications.

[53]  G. Knothe.  Improving biodiesel fuel properties by modifying fatty ester composition , 2009 .

[54]  Ying Zhang,et al.  Hydrotreating of Phenolic Compounds Separated from Bio-oil to Alcohols , 2012 .

[55]  A. Krause,et al.  Effect of H2S on the stability of CoMo/Al2O3 catalysts during hydrodeoxygenation , 2000 .

[56]  Bernard Delmon,et al.  Influences of the Hydrogen Sulfide Partial Pressure and of a Nitrogen Compound on the Hydrodeoxygenation Activity of a CoMo/Carbon Catalyst , 2001 .

[57]  Keshav C. Das,et al.  Production of Biocrude Oil from Microalgae via Thermochemical Liquefaction Process , 2009 .

[58]  Prasant Kumar Rout,et al.  Production of first and second generation biofuels: A comprehensive review , 2010 .

[59]  S. E. Drummond,et al.  Thermal decomposition of acetate: III. Catalysis by mineral surfaces , 1994 .

[60]  Päivi Aakko-Saksa,et al.  Emissions with Heavy-duty Diesel Engines and Vehicles using FAME, HVO and GTL Fuels with and without DOC+POC Aftertreatment , 2009 .

[61]  Samuel A. Lewis,et al.  Bio-oil upgrading over platinum catalysts using in situ generated hydrogen , 2009 .

[62]  D. Klass.  Energy from Biomass and Wastes , 1984, Bio/Technology.

[63]  Krisztian Kordas,et al.  Deoxygenation of dodecanoic acid under inert atmosphere , 2010 .

[64]  H. L. Barnebey,et al.  Continuous fat splitting plants using the colgate-emery process , 1948 .

[65]  S. S. Agrawal.  Advances in tank quality measurements can help cut operational costs , 2007 .

[66]  T. Choudhary,et al.  Renewable fuels via catalytic hydrodeoxygenation , 2011 .

[67]  P. Nichols,et al.  Fatty acid and lipid composition of 10 species of microalgae used in mariculture , 1989 .

[68]  J. Dumesic,et al.  Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water , 2002, Nature.

[69]  D. Leckel,et al.  Diesel-Selective Hydrocracking of an Iron-Based Fischer−Tropsch Wax Fraction (C15−C45) Using a MoO3-Modified Noble Metal Catalyst , 2006 .

[70]  A. Krause,et al.  Effect of hydrogen sulphide on the hydrodeoxygenation of aromatic and aliphatic oxygenates on sulphided catalysts , 2007 .

[71]  Gérald Djéga-Mariadassou,et al.  Utilization of vegetable oils as an alternative source for diesel-type fuel: hydrocracking on reduced Ni/SiO2 and sulphided Ni-Mo/γ-Al2O3 , 1989 .

[72]  A. Krause,et al.  Hydrodeoxygenation of aliphatic esters on sulphided NiMo / gAl 2 O 3 and CoMo / gAl 2 O 3 catalyst : The effect of water , 2005 .

[73]  L. C. Meher,et al.  Technical aspects of biodiesel production by transesterification—a review , 2006 .

[74]  Phillip E. Savage,et al.  Hydrothermal Liquefaction of a Microalga with Heterogeneous Catalysts , 2011 .

[75]  A. Lemonidou,et al.  Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes , 2011 .

[76]  P. Risé,et al.  Marine macroalgae analyzed by mass spectrometry are rich sources of polyunsaturated fatty acids. , 2005, Journal of mass spectrometry : JMS.

[77]  Murray R. Gray,et al.  Pyrolytic Decarboxylation and Cracking of Stearic Acid , 2008 .

[78]  D. M. Tillett,et al.  Design and operation of an outdoor microalgae test facility , 1989 .

[79]  Yusuf Chisti,et al.  Fuels from microalgae , 2010 .

[80]  Green diesel production by hydrorefining renewable feedstocks , 2008 .

[81]  Anthony V. Bridgwater,et al.  Developments in direct thermochemical liquefaction of biomass: 1983-1990 , 1991 .

[82]  Päivi Aakko,et al.  NExBTL - Biodiesel Fuel of the Second Generation , 2005 .

[83]  R. Nava,et al.  Upgrading of bio-liquids on different mesoporous silica-supported CoMo catalysts , 2009 .

[84]  A. Krause,et al.  Simultaneous hydrodesulfurization and hydrodeoxygenation: interactions between mercapto and methoxy groups present in the same or in separate molecules , 2001 .

[85]  Stella Bezergianni,et al.  Hydrocracking of vacuum gas oil-vegetable oil mixtures for biofuels production. , 2009, Bioresource technology.

[86]  Mark A. Barteau,et al.  Spectroscopic identification of alkoxide, aldehyde, and acyl intermediates in alcohol decomposition on Pd(111) , 1990 .

[87]  C. Posten,et al.  Second Generation Biofuels: High-Efficiency Microalgae for Biodiesel Production , 2008, BioEnergy Research.

[88]  H. Hiller.  In: Ullmann''''s Encyclopedia of Industrial Chemistry , 1989 .

[89]  Gary R. List,et al.  Hydrolysis of soybean oil. in a subcritical water flow reactor , 1999 .

[90]  A. Krause,et al.  Effect of sulphiding agents on the hydrodeoxygenation of aliphatic esters on sulphided catalysts , 2007 .

[91]  Tom N. Kalnes,et al.  Green Diesel: A Second Generation Biofuel , 2007 .

[92]  Dmitry Yu. Murzin,et al.  Hydrocarbons for diesel fuel via decarboxylation of vegetable oils , 2005 .

[93]  Hydrodeoxygenation of methyl esters on sulphided NiMo / gAl 2 O 3 and CoMo / gAl 2 O 3 catalysts , 2005 .

[94]  J. Dumesic,et al.  Catalytic reforming of oxygenated hydrocarbons for hydrogen with low levels of carbon monoxide. , 2003, Angewandte Chemie.

[95]  Dmitry Yu. Murzin,et al.  Influence of Hydrogen in Catalytic Deoxygenation of Fatty Acids and Their Derivatives over Pd/C , 2012 .

[96]  A. Krause,et al.  Reactions of methyl heptanoate hydrodeoxygenation on sulphided catalysts , 2007 .

[97]  Keri B Cantrell,et al.  Livestock waste-to-bioenergy generation opportunities. , 2008, Bioresource technology.

[98]  H. Henry Lamb,et al.  Catalytic reaction pathways in liquid-phase deoxygenation of C18 free fatty acids , 2010 .

[99]  David Kubička,et al.  Conversion of Vegetable Oils into Hydrocarbons over CoMo/MCM-41 Catalysts , 2010 .

[100]  Douglas C. Elliott,et al.  Historical Developments in Hydroprocessing Bio-oils , 2007 .

[101]  A. Beenackers,et al.  Heterogeneous hydrogenation of vegetable oils: A literature review , 1997 .

[102]  A. Corma,et al.  Chemical routes for the transformation of biomass into chemicals. , 2007, Chemical reviews.

[103]  V. Parmon,et al.  Development of new catalytic systems for upgraded bio-fuels production from bio-crude-oil and biodiesel , 2009 .

[104]  David Kubička,et al.  Hydroprocessed rapeseed oil as a source of hydrocarbon-based biodiesel , 2009 .

[105]  A. Krause,et al.  Hydrodeoxygenation of aliphatic esters on sulphided NiMo/γ-Al2O3 and CoMo/γ-Al2O3 catalyst: The effect of water , 2005 .

[106]  A. Krause,et al.  Hydrodeoxygenation of methyl esters on sulphided NiMo/γ-Al2O3 and CoMo/γ-Al2O3 catalysts , 2005 .

[107]  Bernard Delmon,et al.  Study of the Hydrodeoxygenation of Carbonyl, Carboxylic and Guaiacyl Groups Over Sulfided Como/gamma-al2o3 and Nimo/gamma-al2o3 Catalyst .2. Influence of Water, Ammonia and Hydrogen-sulfide , 1994 .

[108]  Daniel E. Resasco,et al.  Solid Nanoparticles that Catalyze Biofuel Upgrade Reactions at the Water/Oil Interface , 2010, Science.

[109]  Dmitry Yu. Murzin,et al.  Catalytic Deoxygenation of Fatty Acids and Their Derivatives , 2007 .

[110]  S. Ramayya,et al.  Heterolysis and homolysis in supercritical water , 1987 .

[111]  Ayhan Demirbas,et al.  Oily Products from Mosses and Algae via Pyrolysis , 2006 .

[112]  Dmitry Yu. Murzin,et al.  Heterogeneous Catalytic Deoxygenation of Stearic Acid for Production of Biodiesel , 2006 .

[113]  Timo Murtonen,et al.  Hydrotreated Vegetable Oil as Fuel for Heavy Duty Diesel Engines , 2007 .

[114]  D. J. Rickeard,et al.  Understanding diesel lubricity , 2000 .

[115]  Gabriele Centi,et al.  Catalysis for Renewables , 2007 .

[116]  Phillip E. Savage,et al.  Decomposition of Formic Acid under Hydrothermal Conditions , 1998 .

[117]  Chen Zhao,et al.  Highly selective catalytic conversion of phenolic bio-oil to alkanes. , 2009, Angewandte Chemie.

[118]  E. Molina Grima,et al.  Downstream processing of algal polyunsaturated fatty acids. , 1998, Biotechnology advances.

[119]  Jefferson W. Tester,et al.  Acetic acid oxidation and hydrolysis in supercritical water , 1995 .

[120]  Baltazar D. Aguda,et al.  How do diesel-fuel ignition improvers work? , 1993 .

[121]  Yanyong Liu,et al.  Production of Synthetic Diesel by Hydrotreatment of Jatropha Oils Using Pt−Re/H-ZSM-5 Catalyst , 2010 .

[122]  Martti Larmi,et al.  Hydrotreated Vegetable Oil (HVO) as a Renewable Diesel Fuel: Trade-off between NOx, Particulate Emission, and Fuel Consumption of a Heavy Duty Engine , 2008 .

[123]  Morgan Fröling,et al.  Thermochemical biofuel production in hydrothermal media: A review of sub- and supercritical water technologies , 2008 .

[124]  A. Bridgwater,et al.  Fast pyrolysis processes for biomass , 2000 .

[125]  Mary E. Rezac,et al.  Partial hydrogenation of soybean oil using metal-decorated integral-asymmetric polymer membranes: Effects of morphology and membrane properties , 2010 .

[126]  Malcolm R. Brown,et al.  Nutritional properties of microalgae for mariculture , 1997 .

[127]  G. N. D. R. Filho,et al.  Formation of alkanes, alkylcycloalkanes and alkylbenzenes during the catalytic hydrocracking of vegetable oils , 1993 .