Hydrothermal conversion of glycerol to chemicals and hydrogen: Review and perspective

Biofuels, Bioproducts and Biorefining

Volumn 6, Issue 6, 2012, Pages 686-702

  Long, Yun Duo ^a,b   Fang, Zhen ^a  

^a CHINESE ACADEMY OF SCIENCES   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Acrolein; Glycerol; Hydrogen; Hydrothermal; Lactic acid; Supercritical water

Indexed keywords

ALDEHYDES; CATALYSTS; HERBICIDES; HYDROGEN; LACTIC ACID; CHEMICAL INDUSTRY; CHEMICALS;

ACROLEIN; BIODIESEL PRODUCTION; HYDROTHERMAL; HYDROTHERMAL CONVERSION; HYDROTHERMAL GASIFICATION; HYDROTHERMAL PROCESS; SUB- AND SUPER-CRITICAL; SUPERCRITICAL WATER; VALUE ADDED PRODUCTS;

GLYCEROL;

EID: 84872982447     PISSN: 1932104X     EISSN: 19321031     Source Type: Journal    
DOI: 10.1002/bbb.1345     Document Type: Review

References (109)

1. Bessou C, Ferchaud F, Gabrielle B and Mary B, Biofuels, greenhouse gases and climate change. A review. Agron Sust Dev 31:1-79 (2011).
2. Ong HC, Mahlia TMI, Masjuki HH and Norhasyima RS, Comparison of palm oil, Jatropha curcas and Calophyllum inophyllum, for biodiesel: A review. Renew Sust Energ Rev 15:3501-3515 (2011).
3. Marchetti JM and Fang Z, Biodiesel: Blends, Properties and Applications. Nova Science Publishers Inc., New York (2011).
4. Luque R, Lovett JC, Datta B, Clancy J, Campelo JM and Romero AA, Biodiesel as feasible petrol fuel replacement: A multidisciplinary overview. Energy Environ Sci 3:1706-1721 (2010).
5. Deng X, Fang Z and Liu YH, Ultrasonic transesterification of Jatropha curcas L.oil to biodiesel by a two-step process. Energ Convers Manage 51:2802-2807 (2010).
6. Deng X, Fang Z, Liu YH and Yu CL, Production of biodiesel from Jatropha oil catalyzed by nanosized solid basic catalyst. Energy 36:777-784 (2011).
7. Thurmond W, Biodiesel 2020: A Global Market Survey, 2nd edition. [Online]. Emerging Markets Online (2008). Available at: http://www.emerging-markets.com/biodiesel/ [December 12, 2008].
8. Tyson KS, Bozell J, Wallace R, Petersen E and Moens L, Biomass Oil Analysis, Research Needs and Recommendations. NREL/TP-510-34796, 2004.
9. European Biodiesel Board, EU Policy Demand for Biodiesel. [Online]. Available at: http://www.ebb-eu.org/index.php [April 30, 2007].
10. Chiu CW, Goff MJ and Suppes GJ, Distribution of methanol and catalysts between biodiesel and glycerol. AIChE J 51:1274-1278 (2005).
11. Pagliaro M and Rossi M, The Future of Glycerol, 2nd edition. Royal Society Of Chemistry, United States (2010).
12. Van Gerpen J, Biodiesel processing and production. Fuel Process Technol 86:1097-1107 (2005).
13. Zhou CH, Beltramini JN, Fan YX and Lu GQ, Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem Soc Rev 37:527-549 (2008).
14. Duane TJ and Katherine AT, The glycerin glut: Options for the value-added conversion of crude glycerol resulting from biodiesel production. Environ Prog 26:338-348 (2007).
15. Behr A, Eilting J, Irawadi K, Leschinski J and Lindner F, Improved utilization of renewable resources: New important derivatives of glycerol. Green Chem 10:13-30 (2008).
16. Pagliaro M, Ciriminna R, Kimura H, Rossi M and Della Pina C, From glycerol to value-added products. Angew Chem Int Ed 46:4434-4440 (2007).
17. Srokol Z, Bouche AG, Van Estrik A, Strik RCJ, Maschmeyer T and Peters JA, Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds. Carbohyd Res 339:1717-1726 (2004).
18. 3 and Ni in subcritical water at 350°C. Ind Eng Chem Res 43:2454-2463 (2004).
19. Fang Z, Sato T, Smith Jr RL, Inomata H, Arai K and Kozinski JA, Reaction chemistry and phase behavior of lignin in high-temperature and supercritical water. Bioresource Technol 99:3424-3430 (2008).
20. Cortright RD, Davda RR and Dumesic JA, Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water. Nature 418:964-967 (2002).
21. Temelli F, Perspectives on supercritical fluid processing of fats and oils. J Supercrit Flu 47:583-590 (2009).
22. Klingler D, Berg J and Vogel H, Hydrothermal reactions of alanine and glycine in sub- and supercritical water. J Supercrit Flu 43:112-119 (2007).
23. Yazdani SS and Gonzalez R, Anaerobic fermentation of glycerol: A pathto economic viability for the biofuels industry. Curr Opin Biotech 18:213-219 (2007).
24. Möller M, Nilges P, Harnisch F and Schröder U, Subcritical water as reaction environment: Fundamentals of hydrothermal biomass transformation. ChemSusChem 4:566-579 (2011).
25. Peterson AA, Vogel F, Lachance RP, Fröling M, Antal Jr MJ and Tester JW, Thermochemical biofuel production in hydrothermal media: A review of sub- and supercritical water technologies. Energ Environ Sci 1:32-65 (2008).
26. Weingärtner H and Franck EU, Supercritical water as a solvent. Angew Chem Int Ed 44:2672-2692 (2005).
27. An JY, Bagnell L, Cablewski T, Strauss CR and Trainor RW, Applications of high-temperature aqueous media for synthetic organic reactions. J Org Chem 62:2505-2511 (1997).
28. Antal MJ, Brittain A, Dealmeida C, Ramayya S and Roy JC, Heterolysis and homolysis in supercritical water. ACS Sym Ser 329:77-86 (1987).
29. Fang Z, Complete Dissolution and Oxidation of Organic Wastes in Water. VDM Verlag, Germany (2009).
30. Fang Z, Rapid Production of Micro- and Nano-particles using Supercritical Water. Springer-Verlag, Berlin and Heidelberg, Germany (2010).
31. Akiya N and Savage PE, Roles of water for chemical reactions in high-temperature water. Chem Rev 102:2725-2750 (2002).
32. Galkin AA and Lunin VV, Subcritical and supercritical water: A universal medium for chemical reactions. Russ Chem Rev+ 74:21-35 (2005).
33. Archer D and Wang P, The dielectric constant of water and Debye-Hückel limiting law slopes. J Phys Chem Ref Data 19:371-411 (1990).
34. Bandura A and Lvov S, The ionization constant of water over wide ranges of temperature and density. J Phys Chem Ref Data 35:15-30 (2006).
35. Kruse A, Dinjus E. Hot compressed water as reaction medium and reactant: Properties and synthesis reactions. J Supercrit Flu 39:362-380 (2007).
36. Lehr V, Sarlea M, Ott L and Vogel H, Catalytic dehydration of biomass-derived polyols in sub- and supercritical water. Catal Today 121:121-129 (2007).
37. Toor SS, Rosendahl L and Rudolf A, Hydrothermal liquefaction of biomass: A review of subcritical water technologies. Energy 36:2328-2342 (2011).
38. Osada M, Sato T, Watanabe M, Shirai M and Arai K, Catalytic gasification of wood biomass in subcritical and supercritical water. Combust Sci Technol 178:537-552 (2006).
39. Kruse A and Dinjus E. Hot compressed water as reaction medium and reactant 2. Degradation reactions. J Supercrit Flu 41:361-379 (2007).
40. Westacott RE, Johnston KP and Rossky PJ, Stability of ionic and radical molecular dissociation pathways for reaction in supercritical water. J Phys Chem B 105:6611-6619 (2001).
41. Antal MJ, Mok WSL, Roy JC, Raissi AT and Anderson DGM, Pyrolytic source of hydrocarbons from biomass. J Anal Appl Pyrol 8:291-303 (1985).
42. Bühler W, Dinjus E, Ederer HJ, Kruse A and Mas C, Ionic reactions and pyrolysis of glycerol as competing reaction pathways in near- and supercritical water. J Supercrit Flu 22:37-53 (2002).
43. Qadariyah L, Mahfud, Sumarno, Machmudah S, Wahyudiono, Sasaki M and Goto M, Degradation of glycerol using hydrothermal process. Bioresource Technol 102:9267-9271 (2011).
44. Nimlos MR, Blanksby SJ, Qian X, Himmel ME and Johnson DK, Mechanisms of glycerol dehydration. J Phys Chem A 110:6145-6156 (2006).
45. Tsukuda E, Sato S, Takahashi R and Sodesawa T, Production of acrolein from glycerol over silica-supported heteropoly acids. Catal Commun 8:1349-1353 (2007).
46. Chai SH, Wang HP, Liang Y and Xu BQ, Sustainable production of acrolein: Investigation of solid acid-base catalysts for gas-phase dehydration of glycerol. Green Chem 9:1130-1136 (2007).
47. Alhanash A, Kozhevnikova EF and Kozhevnikov IV, Gas-phase dehydration of glycerol to acrolein catalysed by caesium heteropoly salt. Appl Catal A-Gen 378:11-18(2010).
48. Groll HPA, Okaland and Hearne G. US Patent 2042224 (1936).
49. Ramayya S, Brittain A, DeAlmeida C, Mok W and Antal MJ, Acid-catalysed dehydration of alcohols in supercritical water. Fuel 66:1364-1371 (1987).
50. Antal MJ, Mok WSL and Richards GN, Kinetic-studies of the reations of ketoses and aldoses in water at high-temperature.2. 4-carbon model compounds for the reactions of sugars in water at high-temperature. Carbohyd Res 199:111-115 (1990).
51. Watanabe M, Iida T, Aizawa Y, Aida TM and Inomata H, Acroleinsynthesis from glycerol in hot-compressed water. Bioresource Technol 98:1285-1290 (2007).
52. Ott L, Bicker M and Vogel H, Catalytic dehydration of glycerol in sub- and supercritical water: a new chemical process for acrolein production. Green Chem 8:214-220 (2006).
53. Lehr V, Sarlea M, Ott L and Vogel H, Catalytic dehydration of biomass-derived polyols in sub- and supercritical water. Catal Today 121:121-129 (2007).
54. Hoyt H and Manninen T, Production of acrolein from glycerol. US Patent 2558520 (1951).
55. Neher A, Haas T, Dietrich A, Klenk H and Girke W, Acrolein prodn.-by dehydration of a glycerin-water mixt. using a solid acid catalyst, esp. a zeolite. German Patent 4238493-C1 (1994).
56. De Oliveira AS, Vasconcelos SJS, De Sousa JR, De Sousa FF, Filho JM and Oliveira AC, Catalytic conversion of glycerol to acrolein over modified molecular sieves: Activity and deactivation studies. Chem Eng J 168:765-774 (2011).
57. Katryniok B, Paul S, Capron M, and Dumeignil F, Towards the sustainable production of acrolein by glycerol dehydration. ChemSusChem 2:719-730 (2009).
58. Yan XY, Jin FM, Tohji K, Kishita A and Enomoto H, Hydrothermal conversion of carbohydrate biomass to lactic acid. AICHE J 56:2727-2733 (2010).
59. Zhang SP, Jin FM, Hu JJ and Huo ZB, Improvement of lactic acid production from cellulose with the addition of Zn/Ni/C under alkaline hydrothermal conditions. Bioresource Technol 102:1998-2003 (2011).
60. Kishida H, Jin FM, Zhou ZY, Moriya T and Enomoto H, Conversion of glycerin into lactic acid by alkaline hydrothermal reaction. Chem Lett 34:1560-1561 (2005).
61. Shen Z, Jin FM, Zhang YL, Wu B, Kishita A, Tohji K and Kishida H, Effect of alkaline catalysts on hydrothermal conversion of glycerin into lactic acid. Ind Eng Chem Res 48:8920-8925 (2009).
62. Ramírez-López CA, Ochoa-Gómez JR, Fernández-Santos M, Gómez-Jiménez-Aberasturi O, Alonso-Vicario A and Torrecilla-Soria J, Synthesis of lactic acid by alkaline hydrothermal conversion of glycerol at high glycerol concentration. Ind Eng Chem Res 49:6270-6278 (2010).
63. Mok WS, Antal MJ Jr and Jones M Jr, Formation of acrylic acid from lactic acid in supercritical water. J Org Chem 54:4596-4602 (1989).
64. Lira CT and McCrackin PJ, Conversion of lactic acid to acrylic acid in near-critical water. Ind Eng Chem Res 32:2608-2613 (1993).
65. Aida TM, Ikarashi A, Saito Y, Watanabe M, Smith RL and Arai K, Dehydration of lactic acid to acrylic acid in high temperature water at high pressures. J Supercrit Flu 50:257-264 (2009).
66. Jin FM and Enomoto H, Rapid and highly selective conversion of biomass into value-added products in hydrothermal conditions: chemistry of acid/base-catalysed and oxidation reactions. Energy Environ Sci 4:382-397 (2011).
67. Long YD, Guo F, Fang Z, Tian XF, Jiang LQ and Zhang F, Production of biodiesel and lactic acid from rapeseed oil using sodium silicate as catalyst. Bioresource Technol 102:6884-6886 (2011).
68. Masui H, Chen DP, Akai T and Yazawa T, Hydration in alkali-silicate glasses studied by two dimensional multi-quantum magic angle spinning. Z Naturforsch A 57:473-478 (2002).
69. Yuksel A, Koga H, Sasaki M and Goto M, Electrolysis of glycerol in subcritical water. J Renew Sust Energy 1(033112):1-12 (2009).
70. Souza RF, Padilha JC, Goncalves RS and Souza MO, and Rault-Berthelot J, Electrochemical hydrogen production from water electrolysis using ionic liquid as electrolytes: Towards the best device. J Power Sources 164:792-798 (2007).
71. Kishida H, Jin F, Yan X, Moriya T and Enomoto H, Formation of lactic acid from glycolaldehyde by alkaline hydrothermal reaction. Carbohyd Res 341:2619-2623 (2006).
72. Yuksel A, Koga H, Sasaki M and Goto M, Hydrothermal electrolysis of glycerol using a continuous flow reactor. Ind Eng Chem Res 49:1520-1525 (2010).
73. Armaroli N and Balzani V, The hydrogen issue. ChemSusChem 4:21-36 (2011).
74. Adhikari S, Fernando SD and Haryanto A, Hydrogen production from glycerol: An update. Energ Convers Manage 50:2600-2604 (2009).
75. Cortright RD, Davda RR and Dumesic JA, Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water. Nature 418:964-966 (2002).
76. 2 production from biomass-derived hydrocarbons. Science 300:2075-2077 (2003).
77. Soares RR, Simonetti DA and Dumesic JA, Glycerol as a source for fuels and chemicals by low-temperature catalytic processing. Angew Chem Int Ed 45:3982-3985 (2006).
78. Wen GD, Xu YP, Ma HJ, Xu ZS and Tian ZJ, Production of hydrogen by aqueous-phase reforming of glycerol. Int J Hydro Energy 33:6657-6666 (2008).
79. 3 modified by Mg, Zr, Ce or La. Top Catal49:46-58 (2008).
80. Lehnert K and Claus P, Influence of Pt particle size and support type on the aqueous-phase reforming of glycerol. Catal Commun 9:2543-2546 (2008).
81. Luo NJ, Fu XW, Cao FH, Xiao TC and Edwards PP, Glycerol aqueous phase reforming for hydrogen generation over Pt catalyst-effect of catalyst composition and reaction conditions. Fuel 87:3483-3489 (2008).
82. Menezes AO, Rodrigues MT, Zimmaro A, Borges LEP and Fraga MA, Production of renewable hydrogen from aqueous-phase reforming of glycerol over Pt catalysts supported on different oxides. Renew Energ 36:595-599 (2011).
83. 2. Fuel Process Technol 92:330-335 (2011).
84. Luo NJ, Kun OY, Cao FH and Xiao TC, Hydrogen generation from liquid reforming of glycerin over Ni-Co bimetallic catalyst. Biomass Bioenerg 34:489-495 (2010).
85. Kruse A, Supercritical water gasification. Biofuel Bioprod Bioref2:415-437 (2008).
86. Elliott DC, Catalytic hydrothermal gasification of biomass. Biofuel Bioprod Bioref 2:254-265 (2008).
87. Kersten SRA, Potic B, Prins W and Van Swaaij WPM, Gasification of model compounds and wood in hot compressed water. Ind Eng Chem Res 45:4169-4177 (2006).
88. Chakinala AG, Win Brilman DWF, Van Swaaij and Kersten SRA, Catalytic and non-catalytic supercritical water gasification of microalgae and glycerol. Ind Eng Chem Res 49:1113-1122 (2010).
89. Xu DH, Wang SZ, Hu X, Chen CM and Zhang QM, Catalytic gasificatio of glycine and glycerol in supercritical water. Int J Hydro Energy 34:5357-5364 (2009).
90. 3 catalyst. Fuel 87:2956-2960 (2008).
91. May A, Salvadóa J, Torras C and Montanéa D, Catalytic gasification of glycerol in supercritical water. Chem Eng J 160:751-759 (2010).
92. Martin A, Armbruster U and Atia H, Recent developments in dehydration of glycerol toward acrolein over heteropolyacids. Eur J Lipid Sci Technol 114:10-23 (2012).
93. Onda A, Ochi T, Kajiyoshi K and Yanagisawa K, Lactic acid proction from glucose over activated hydrotalcites as solid base catalysts in water. Catal Commun 9:1050-1053 (2008).
94. Roy D, Subramaniam B and Chaudhari RV, Cu-based catalysts show low temperature activity for glycerol conversion to lactic acid. ACS Catal 1:548-551 (2011).
95. Deleplanque J, Dubois JL, Devaux JF and Ueda W, Production of acrolein and acrylic acid through dehydration and oxydehydration of glycerol with mixed oxide catalysts. Catal Today 157:351-358 (2010).
96. Dolores Soriano M, Concepción P, López Nieto JM, Cavani F, Guidetti S and Trevisanut C, Tungsten-Vanadium mixed oxides for the oxidehydration of glycerol into acrylic acid. Green Chem 13:2954-2962 (2011).
97. Holm MS, Saravanamurugan S and Taarning E, Conversion of sugars to lactic acid derivatives using heterogeneous zeotype catalysts. Science 328:602-605 (2010).
98. Wang J, Masui Y and Onaka M, Conversion of triose sugars with alcohols to alkyl lactates catalyzed by Brøsted acid tin ion-exchanged montmorillonite. Appl Catal B-Environ 107:135-139 (2011).
99. King DL, Zhang L, Xia G, Karim AM, Heldebrant DJ, Wang X et al., Aqueous-phase reforming of glycerol for hydrogen production over Pt-Re supported on carbon. Appl Catal B-Environ 99:206-213 (2010).
100. Porta F and Prati L, Selective oxidation of glycerol to sodium glycerate with gold-on-carbon catalyst: An insight into reaction selectivity. J Catal 224:397-403 (2004).
101. 2 catalysts. Chem-Eur J 16:7368-7371 (2010).
102. 3 with glycerin under alkaline hydrothermal conditions. RSC Adv 2:797-801 (2012).
103. Ten Dam J and Hanefeld U, Renewable chemicals: Dehydroxylation of glycerol and polyols. ChemSusChem 4:1017-1034 (2011).
104. Miyazawa T, Kusunoki Y, Kunimori K and Tomishige K, Glycerol conversion in the aqueous solution under hydrogenover Ru/C + an ion-exchange resin and its reaction mechanism. J Catal 240:213-221 (2006).
105. Maris EP and Davis RJ, Hydrogenolysis of glycerol over carbon-supported Ru and Pt catalysts. J Catal 249:328-337 (2007).
106. Özgür DÖ and Uysal BZ, Hydrogen production by aqueous phase catalytic reforming of glycerin. Biomass Bioenerg 35:822-826 (2011).
107. Kritzer P. Corrosion in high-temperature and supercritical water and aqueous solutions: A review. J Supercritical Flu 29:1-29 (2004).
108. Yang FX, Hanna M and Sun RC, Value-added uses for crude glycerol-a byproduct of biodiesel production. Biotechnol Biofuels 5:13 (2012).
109. Van Bennekom, Venderbosch RH, Assink D and Heeres HJ, Reforming of methanol and glycerol in supercritical water. J Supercrit Flu 58:99-113 (2011).