Catalytic valorization of raw glycerol derived from biodiesel: a review

References

• Marchetti JM, Miguel VU, Errazu AF. Possible methods for biodiesel production. Renew Sust Energ Rev. 2007;11:1300–1311.
   Web of Science ®Google Scholar
• Xu Y, Liu H, Du W, et al. Integrated production for biodiesel and 1,3 propanediol with lipase-catalyzed transesterification and fermentation. Biotechnical lett. 2009;31:1335–1341.
   PubMed Web of Science ®Google Scholar
• Yang F, Hanna MA, Sun R. Value-added uses for crude glycerol-a byproduct of biodiesel production. Biotechnol Biofuels. 2012;5:13.
   PubMed Web of Science ®Google Scholar
• Pagliaro M, Ciriminna R, Kimura H, et al. Recent advances in the conversion of bioglycerol into value added products. Eur J Lipid Sci Tech. 2009;111:788–799.
   Web of Science ®Google Scholar
• Johnson DT, Taconi KA. The glycerol glut: option for the value-added conversion of crude glycerol resulting from biodiesel production. Environ Prog. 2007;26:338–348.
   Google Scholar
• Lee KH, Park CH, Lee EY. Biosynthesis of glycerol carbonate from glycerol by lipase in dimethyl carbonate as the solvent. Bioprocess Biosyst Eng. 2010;33:1059–1065.
   PubMed Web of Science ®Google Scholar
• Ezhova NN, Korosteleva IG, Kolesnichenko NV, et al. Glycerol carboxylation to Glycerol Carbonate in the Presence of Rhodium Complexes with Phosphine Ligands, Petroleum. Chemistry. 2012;52(2):109–115.
   Web of Science ®Google Scholar
• Dibenedetto A, Angelini A, Aresta M, et al. Converting wastes into added value products: from glycerol to glycerol carbonate, glycidol and epichlorohydrin using environmentally friendly synthetic routes. Tetrahedron. 2011;67:1308–1313.
   Web of Science ®Google Scholar
• Sudarsanam P, Mallesham B, Reddy PS, et al. Highly Promising Sulfate Ion Promoted M–ZrO2 (M=Al2O3 and CeO2) Heterogeneous Solid Acids for Biodiesel–Derived Glycerol Esterification. J Chem Sci Technol. 2013;2(3):161–168.
   Google Scholar
• Rane SA, Pudi SM, Biswas P. Esterification of Glycerol with Acetic Acid over Highly Active and Stable Alumina-based Catalysts: A Reaction Kinetics Study. Chemical and Biochemical Engineering Quaterly. 2016;30(1):33–45.
   Web of Science ®Google Scholar
• Bosco SMD, Gonçalves M, Figueiredo FCA, et al. Sulfated Pillared Clay as Catalyst in Glycerol Esterification with Caprylic Acid. Waste Biomass Valori. 2016;7(5):1–10.
   Web of Science ®Google Scholar
• Marchetti JM. Heterogeneous esterification of glycerol by using a gold catalyst. Biomass Convers Biorefin. 2016;6(4):457–463.
   Web of Science ®Google Scholar
• Hamerski F, Prado MA, da Silva VR, et al. Kinetics of layered double hydroxide catalyzed esterification of fatty acids with glycerol. React Kinet Mech Cat. 2016;117(1):253–268.
   Web of Science ®Google Scholar
• Konwar LJ, Mäki-Aevela P, Begum P, et al. Shape selectivity and acidity effects in glycerol acetylation with acetic anhydride: selective synthesis of triacetin over Y-zeolite and sulfonated mesoporous carbon. J catal. 2015;329:237–247.
   Web of Science ®Google Scholar
• Pudi SM, Mondal T, Biswas P, et al. Conversion of Glycerol into Value-Added Products Over Cu–Ni Catalyst Supported on γ-Al2O3 and Activated Carbon. Int J Chem React Eng. 2014;12(1):151–162.
   Web of Science ®Google Scholar
• Mostafa NA, Maher A, Abdelmoez W. Production of mono-, di-, and triglycerides from waste fatty acids through esterification with glycerol. Adv Biosci Biotechnol. 2013;4:900–907.
   Google Scholar
• Mufrodi Z, Rochmadi, Sutijanet al., Continuous Process of Reactive Distillation to Produce Bio-additive Triacetin From Glycerol. Mod Appl Sci. 2013;7(10).
   Google Scholar
• Kale S, Armbruster U, Umbarkar S, et al. Esterification of glycerol with acetic acid for improved production of triacetin using toluene as an entrainer. 10^th Green Chemistry Conference; Spain; 2013.
   Google Scholar
• Mufrodi Z, Sutijan, Rochmadi, Budiman A. Chemical Kinetics for Synthesis of Triacetin from Biodiesel Byproduct. Int J Chem. 2012;4(2).
   Google Scholar
• Khayoon MS, Hameed BH. Acetylation of glycerol to biofuel additives over sulphated activated carbon catalyst. Bioresource Technol. 2011;102:9229–9235.
   PubMed Web of Science ®Google Scholar
• Ghoreishi KB, Yarmo MA. Sol-gel Sulfated Silica as a Catalyst for Glycerol Acetylation with Acetic Acid. J Sci Technol. 2013;5(1):65–78.
   Google Scholar
• Reddy PS, Sudarsanam P, Raju G, et al. Synthesis of bio-additives: acetylation of glycerol over zirconia-based solid acid catalysts. Catal Commun.2010;11(15):1224–1228.
   Google Scholar
• Gade SM, Munshi MK, Chherawalla BM, et al. Synthesis of glycidol from glycerol and dimethyl carbonate using ionic liquid as a catalyst. Catal Commun. 2012;27:184–188.
   Web of Science ®Google Scholar
• Liua P, Derchib M, Hensen EJM. Synthesis of glycerol carbonate by transesterification of glycerol with dimethyl carbonate over MgAl mixed oxide catalysts. Appl Catal A General. 2013;467:124–131.
   Web of Science ®Google Scholar
• Varkolu M, Burri DR, Kamaraju SRR, et al. Transesterification of glycerol with dimethyl carbonate over nanocrystalline ordered mesoporous MgO–ZrO2 solid base catalyst. J Porous Mat. 2016;23(1):185–193.
   Web of Science ®Google Scholar
• Sandesha S, Kristachara PKR, Manjunathana P, et al. Synthesis of biodiesel and acetins by transesterification reactions using novel CaSn(OH)6 heterogeneous base catalyst. Appl Catal A General. 2016;523:1–11.
   Web of Science ®Google Scholar
• Teng WK, Ngoh GC, Yusoff R, et al. Microwave-assisted transesterification of industrial grade crude glycerol for the production of glycerol carbonate. Chem Eng J. 2016;284:469–477.
   Web of Science ®Google Scholar
• Ishaka ZI, Sairia NA, Aliasa Y, et al. Production of glycerol carbonate from glycerol with aid of ionic liquid as catalyst. Chem Eng J. 2016;297:128–138.
   Web of Science ®Google Scholar
• Granados-Reyes J, Salagre P, Cesteros Y. CaAl-layered double hydroxides as active catalysts for the transesterification of glycerol to glycerol carbonate. Appl Clay Sci. 2016;132–133:216–222.
   Web of Science ®Google Scholar
• Bai R, Wang Y, Wang S, et al. Synthesis of glycerol carbonate from glycerol and dimethyl carbonate catalyzed by NaOH/γ-Al2O3. Fuel Process Technol. 2013;106:209–214.
   Web of Science ®Google Scholar
• Parameswaram G, Srinivas M, Hari Babu B, et al. Transesterification of glycerol with dimethyl carbonate for the synthesis of glycerol carbonate over Mg/Zr/Sr mixed oxide base catalysts. Catal Sci Technol. 2013;3:3242.
   Web of Science ®Google Scholar
• Ochoa-Gómez JR, Gómez-Jiménez-Aberasturi O, Ramírez-López C, et al. Synthesis of glycerol 1,2-carbonate by transesterification of glycerol with dimethyl carbonate using triethylamine as a facile separable homogeneous catalyst. Green Chem. 2012;14:3368.
   Web of Science ®Google Scholar
• Bagheri S, Julkapli NM, Yehye WA. . Catalytic conversion of biodiesel derived raw glycerol to value added products. Renew Sust Energ Reviews. 2015;41:113–127.
   Web of Science ®Google Scholar
• Melero JA, Vicente G, Morales G, et al. Acid-catalyzed etherification of bio-glycerol and isobutylene over sulfonic mesostructured silicas. Appl Catal A General. 2008;346:44–51.
   Web of Science ®Google Scholar
• Frusteria L, Cannillab C, Bonurab G, et al. Carbon microspheres preparation, graphitization and surface functionalization for glycerol etherification. Catal Today. 2016;277:68–77.
   Web of Science ®Google Scholar
• Simonea N, Carvalhoa WA, Mandellia D, et al. Nanostructured MFI-type zeolites as catalysts in glycerol etherification with tert-butyl alcohol. J Mol Catal A Chemical. 2016;422:115–121.
   Web of Science ®Google Scholar
• Srinivas M, Sree R, Raveendra G, et al. Selective etherification of glycerol with tert-butanol over 12-tungstophosphoric acid catalysts supported on Y-zeolite. Indian J Chem. 2014;53A:524–529.
   Google Scholar
• Roze M, Kampars V, Teivena K, et al. Catalytic Etherification of Glycerol with Alcohols. Mater Sci Appl Chem. 2013;28:67–72.
   Google Scholar
• Gholami Z, Abdullah AZ, Lee KT. Selective Etherification of Glycerol over Heterogeneous Mixed Oxide Catalyst: Optimization of Reaction Parameters. Chem Eng Sci. 2013;1(4):79–86.
   Google Scholar
• Sivaiah MV, Robles-Manuel S, Valange S, et al. Recent developments in acid and base-catalyzed etherification of glycerol to polyglycerols. Catal Today. 2012;198:305–313.
   Web of Science ®Google Scholar
• Lee HJ, Seung D, Filimonov IN, et al. Etherification of glycerol by isobutylene. Effects of the density of acidic sites in ion-exchange resin on the distribution of products. Korean J Chem Eng. 2011;28(3):756–762.
   Web of Science ®Google Scholar
• Cutler AH, Antal MJ Jr., Jones M Jr. Kinetics and mechanism of the vapor phase pyrolysis of 1,3-dioxolane in steam. J Anal Appl Pyrol. 1987;12(3–4):223–242.
   Web of Science ®Google Scholar
• Stein. YS, Antal MJ Jr., Jones M Jr. A study of the gas-phase pyrolysis of glycerol. J Anal Appl Pyrol. 1983;4(4):283–296.
   Web of Science ®Google Scholar
• Panigrahi S, Chaudhari ST, Bakhshi NN, et al. Production of Synthesis Gas/High-Btu Gaseous Fuel from Pyrolysis of Biomass-Derived Oil. Energy Fuels. 2002;16(6):1392–1397.
   Web of Science ®Google Scholar
• Valliyappan T. Hydrogen or Syn Gas Production from Glycerol Using Pyrolysis and Steam Gasification Processes [M. Thesis]. Saskatoon, Saskatchewan: College of Graduate Studies and Research; 2004.
   Google Scholar
• Fernández Y, Arenillas A, Diez MA, et al. Pyrolysis of glycerol over activated carbons for syngas production. J Anal Appl Pyrol. 2009;84:124–150.
   Web of Science ®Google Scholar
• Fernández Y, Arenillas A, Bermúdez JM, et al. Comparative study of conventional and microwave-assisted pyrolysis, steam and dry reforming of glycerol for syngas production, using a carbonaceous catalyst. J Anal Appl Pyrol. 2010;88(2):155–159.
   Web of Science ®Google Scholar
• Lai C-W, Hsiao Y-H, Peng Y-K, et al. Facile synthesis of highly emissive carbon dots from pyrolysis of glycerol; gram scale production of carbon dots/mSiO2 for cell imaging and drug release. J Mater Chem. 2012;22:14403.
   Web of Science ®Google Scholar
• Leong SK, Lam SS, Ani FN, et al. Production of Pyrolyzed oil from Crude glycerol using a microwave heating technique. Int J Technol. 2016;2:323–331.
   Google Scholar
• Katryniok B, Kimura H, Skrzyńska E, et al. Selective catalytic oxidation of glycerol: perspectives for high value chemicals. Green Chem. 2011;13:1960–1979.
   Web of Science ®Google Scholar
• Hu W, Lowry B, Varma A. Catalytic oxidation of glycerol to dihydroxyacetone. 21st International Symposium on Chemical Reaction Engineering, ISCRE. 2016;21.
   Google Scholar
• Kimura H, Tsuto K, Wakisawa T, et al. Selective oxidation of glycerol on a platinum-bismuth catalyst. Appl Catal A General. 1993;96(2):217–228.
   Web of Science ®Google Scholar
• Nie R, Liang D, Shen L, et al. Selective oxidation of glycerol with oxygen in base-free solution over MWCNTs supported PtSb alloy nanoparticles. Appl Catal B Environmental. 2012;127:212–220.
   Web of Science ®Google Scholar
• Wang D, Villa A, Porta F, et al. Single-phase bimetallic system for the selective oxidation of glycerol to glycerate. Chem Commun. 2006;18:1956–1958.
   Web of Science ®Google Scholar
• Ketchie WC, Murayama M, Davis RJ. . Selective oxidation of glycerol over carbon-supported AuPd catalysts. J Catal. 2007;250(2):264–273.
   Web of Science ®Google Scholar
• Prati L, Villa A, Veith GM. Selective Oxidation of Glycerol under Acidic Conditions Using Gold Catalysts. Angew Chem. 2010;122(26):4601–4604.
   Google Scholar
• Brett GL, He Q, Hammond C, et al. Selective Oxidation of Glycerol by Highly Active Bimetallic Catalysts at Ambient Temperature under Base-Free Conditions. Angew Chem. 2011;123(43):10318–10321.
   Google Scholar
• Xu J, Zhang H, Zhao Y, et al. Selective oxidation of glycerol to lactic acid under acidic conditions using AuPd/TiO2 catalyst. Green Chem. 2013;15(6):1520–1525.
   Web of Science ®Google Scholar
• Gil S, Marchena M, Sánchez-Silva L, et al. Effect of the operation conditions on the selective oxidation of glycerol With catalysts based on Au supported on carbonaceous materials. Chem Eng J. 2011;178:423–435.
   Web of Science ®Google Scholar
• Tuinman AA, Cook KD. Fast-Atom Bombardment-Induced Condensation of Glycerol with Ammonium Surfactants I: Regioselectivity of the Adduct Formation. J Am Soc Mass Spectr. 1992;3:318–325.
   PubMed Web of Science ®Google Scholar
• Tuinman AA, Cook KD. Fast-Atom Bombardment-Induced Condensation of Glycerol with Ammonium Surfactants II: Time Dependence of Mass Spectra and Tandem Mass Spectra. J Am Soc Mass Spectr. 1994;5:92–99.
   PubMed Web of Science ®Google Scholar
• Marzi M, Tinti MO, De Angelis F. Chemical process for the stereoselective synthesis of R-(-)-carnitine. US 6420599 B2 Patent. 2002.
   Google Scholar
• Deutsch J, Martin A, Lieske H. Investigations on heterogeneously catalyzed condensations of glycerol to cyclic acetals. J Catal. 2007;245(2):428–435.
   Web of Science ®Google Scholar
• Ferreira P, Fonseca IM, Ramos AM, et al. Valorisation of glycerol by condensation with acetone over silica-induced heteropolyacids. Appl Catal B Environmental. 2010;98(1-2):94–99.
   Web of Science ®Google Scholar
• Serafim H, Fonseca. IM, Ramos. AM, et al. Valorisation of glycerol into fuel additives over zeolite as catalysts. Chem Eng J. 2011;178:291–296.
   Web of Science ®Google Scholar
• Slinn M, Kendall K, Mallon C, et al. Steam reforming of biodiesel by-product to make renewable hydrogen. Bioresource Technol. 2008;99(13):5851–5858.
   PubMed Web of Science ®Google Scholar
• Huber GW, ShabakerJW, Dumesic JA. Raney Ni-Sn Catalyst for H2 Production from Biomass-Derived Hydrocarbons. Science. 2003;300(5628):2075–2077.
   PubMed Web of Science ®Google Scholar
• Menezes AO, Rodrigues MT, Zimmaro A, et al. Production of renewable hydrogen from aqueous-phase reforming ofglycerol over Pt catalysts supported on different oxides. Renew Energ. 2011;36(2):595–599.
   Web of Science ®Google Scholar
• Wen G, Xu Y, Ma H, et al. Production of hydrogen by aqueous-phase reforming of glycerol. Int J Hydrogen Energ. 2008;33:6657–6666.
   Web of Science ®Google Scholar
• Pompeoa F, Santoria G, Nichio NN. Hydrogen and/or syngas from steam reforming of glycerol: study of platinum catalysts. Int J Hydrogen Energ. 2010;35:8912–8920.
   Web of Science ®Google Scholar
• Luo N, Fu X, Cao F, et al. Glycerol aqueous phase reforming for hydrogen generation over Pt catalyst – Effect of catalyst composition and reaction conditions. Fuel. 2008;87(17–18):3483–3489.
   Web of Science ®Google Scholar
• Ciftci A, Peng B, Jentys A, et al. Support effects in the aqueous phase reforming of glycerol over supported platinum catalysts. Appl Catal A General. 2012;431–432:113–119.
   Web of Science ®Google Scholar
• Jiang T, Wang T, Ma L, et al. Investigation on the xylitol aqueous-phase reforming performance for pentane production over Pt/HZSM-5 and Ni/HZSM-5 catalysts. Appl Energ. 2012;90(1):51–57.
   Web of Science ®Google Scholar
• Lehnert K, Claus P. Influence of Pt particle size and support type on the aqueous-phase reforming of glycerol. Catal Commun. 2008;9(15):2543–2546.
   Web of Science ®Google Scholar
• Tuza PV, Manfro RL, Ribeiro NFP, et al. Production of renewable hydrogen by aqueous-phase reforming of glycerol over NieCu catalysts derived from hydrotalcite precursors. Renew Energ. 2013;50:408–414.
   Web of Science ®Google Scholar
• Iriondoa A, Barrio VL, Cambra JF, et al. Influence of La2O3 modified support and Ni and Pt active phases on glycerol steam reforming to produce hydrogen. Catal Commun. 2009;10:1275–1278.
   Web of Science ®Google Scholar
• Guo Y, Liu X, Azmat MU, et al. Hydrogen production by aqueous-phase reforming of glycerol over Ni-B catalysts. Int J Hydrogen Energ. 2012;37:227–234.
   Web of Science ®Google Scholar
• Cui Y, Galvita V, Rihko-Struckmann L, et al. Steam reforming of glycerol: The experimental activity of La1-xCexNiO3 catalyst in comparison to the thermodynamic reaction equilibrium. Appl Catal B Environmental. 2009;90:29–37.
   Web of Science ®Google Scholar
• Iriondoa A, Barrio VL, Cambraa JF, et al. Glycerol steam reforming over Ni catalysts supported on ceria and ceria-promoted alumina. Int J Hydrogen Energ. 2010;35:11622–11633.
   Web of Science ®Google Scholar
• Iriondo A, Barrio VL, Cambra JF, et al. Hydrogen Production from Glycerol Over Nickel Catalysts Supported on Al2O3 Modified by Mg, Zr, Ce or La. Top Catal. 2008;49(1):46–58.
   Web of Science ®Google Scholar
• Murata K, Takahara I, Inaba M. Propane formation by aqueous-phase reforming of glycerol over pt/H-ZSM5 catalysts. React Kinet Catal Lett. 2008;93(1):59–66.
   Google Scholar
• Pendem C, Gupta P, Chaudhary N, et al. Aqueous phase reforming of glycerol to 1,2-propanediol over Pt-nanoparticles supported on hydrotalcite in the absence of hydrogen. Green Chem. 2012;14:3107.
   Web of Science ®Google Scholar
• Freitas ACD, Guirardello R. Comparison of several glycerol reforming methods for hydrogen and syngas production using thermodynamic analysis.
   Google Scholar
• Wolfson A, Dlugy C, Tavor D, et al. Baker's yeast catalysed asymmetric reduction in glycerol. Tetrahedron Asymmetry. 2006;17:2043–2045.
   Web of Science ®Google Scholar
• Wolfson A, Dlugy C. Glycerol as an alternative green medium for carbonyl compound reductions. Org Commun. 2009;2(2):34–41.
   Google Scholar