Abstract
The increase in biodiesel production has resulted in the oversupply of glycerol into the market. Purified and processed glycerol has found many direct applications in pharmaceuticals, food, etc. However, the cost of processing and market value of processed glycerol has driven the research of direct utilization of crude glycerol to industrially essential chemicals. Various methods and research have been devoted to using glycerol to produce value-added products separately. Glycerol can undergo several transformation reactions like hydrogenation, oxidation, alcoholysis, and etherification. Etherification of glycerol can be divided into three main reactions: self-etherification, using alcohol, and olefins and these products have vast applications such as fuel additives, plasticizer, etc. The current review presents a comprehensive summary of glycerol etherification to value-added products and their applications. The catalytic system developed along with reaction conditions and the factors responsible for the better activity is also discussed. Overall, the review presents a detailed discussion on the catalytic system developed, the utilization of different alcohols and olefins, and the application of products. Moreover, the environmental and economic aspects of the etherification of glycerol via various conversion routes while assessing the process parameters needs to be tackled to attain wider adoption of the process.
Acknowledgments
The authors gratefully thank and dedicate this work to Hon. Dr. A. P. J. Abdul Kalam, whose ideas, thoughts, and vision ignited us and inspired us to move in the research field.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
Abbina, S., Vappala, S., Kumar, P., Siren, E.M.J., La, C.C., Abbasi, U., Brooks, D.E., and Kizhakkedathu, J.N. (2017). Hyperbranched polyglycerols: recent advances in synthesis, biocompatibility and biomedical applications. J. Mater. Chem. B 5: 9249–9277, doi:https://doi.org/10.1039/c7tb02515g.Search in Google Scholar PubMed
Adenuga, A.A., Truong, L., Tanguay, R.L., and Remcho, V.T. (2013). Preparation of water soluble carbon nanotubes and assessment of their biological activity in embryonic zebrafish. Int. J. Biomed. Nanosci. Nanotechnol. 3: 38–51, https://doi.org/10.1504/ijbnn.2013.054514.Search in Google Scholar PubMed PubMed Central
Admiral, A. and Abdullah, A.Z. (2014). Shape selectivity effects in etherification of glycerol to diglycerol isomers in a solvent-free reaction system by Li-Mg/SBA-15 catalyst. Catal. Lett. 144: 211–215, https://doi.org/10.1007/s10562-013-1159-3.Search in Google Scholar
Aguado-Deblas, L., Estevez, R., Russo, M., Parola, V. La, Bautista, F.M., and Testa, M.L. (2020). Microwave-assisted glycerol etherification over sulfonic acid catalysts. Materials 13: 1–16, https://doi.org/10.3390/ma13071584.Search in Google Scholar PubMed PubMed Central
Al-Mashhadani, H.A.M., Capareda, S.C., Lacey, R.E., and Fernando, S.D. (2017). Catalytic valorization of glycerol for producing biodiesel-compatible biofuel blends. Biofuels 7629: 1–15.10.1080/17597269.2017.1387746Search in Google Scholar
Alleman, T.L., McCormick, R.L., Christensen, E.D., Fioroni, G., Moriarty, K., and Yanowitz, J. (2016). Biodiesel handling and use guide, 5th ed. Available at: https://doi.org/10.2172/1332064.Search in Google Scholar
Anuar, M.R., Abdullah, A.Z., and Othman, M.R. (2013). Etherification of glycerol to polyglycerols over hydrotalcite catalyst prepared using a combustion method. Catal. Commun. 32: 67–70, https://doi.org/10.1016/j.catcom.2012.12.007.Search in Google Scholar
Arcanjo, M.R.A., da Silva, I.J., Cavalcante, C.L., Iglesias, J., Morales, G., Paniagua, M., Melero, J.A., and Vieira, R.S. (2020). Glycerol valorization: conversion to lactic acid by heterogeneous catalysis and separation by ion exchange chromatography. Biofuel. Bioprod. Biorefin. 14: 357–370, doi:https://doi.org/10.1002/bbb.2055.Search in Google Scholar
Axelsson, L., Franzén, M., Ostwald, M., Berndes, G., Lakshmi, G., and Ravindranath, N.H. (2012). Perspective: Jatropha cultivation in southern India. Assessing farmers’ experiences. Biofuel. Bioprod. Biorefin. 6: 246–256, https://doi.org/10.1002/bbb.1324.Search in Google Scholar
Ayoub, M. and Abdullah, A.Z. (2013). Diglycerol synthesis via solvent-free selective glycerol etherification process over lithium-modified clay catalyst. Chem. Eng. J. 225: 784–789, https://doi.org/10.1016/j.cej.2013.04.044.Search in Google Scholar
Ayoub, M., Sufian, S., Hailegiorgis, S.M., Ullah, S., and Uemura, Y. (2017). Conversion of glycerol to polyglycerol over waste duck-bones as a catalyst in solvent free etherification process. IOP Conf. Ser. Mater. Sci. Eng. Vol. 226, Available at: https://doi.org/10.1088/1757-899X/226/1/012073.Search in Google Scholar
Ayoub, M., Ullah, S., Inayat, A., and Mahmood, S.M. (2016). Investigation of biodiesel-drive glycerol conversion to polyglycerol over basic modified AlPC catalyst. ARPN J. Eng. Appl. Sci. 11: 2668–2672.Search in Google Scholar
Ayoub, M., Yusoff, M.H.M., Yusup, S.B., Danish, M., Ullah, S., and Farrukh, S. (2020). Effect of microwave irradiation on the etherification of biodiesel-derived glycerol in a solvent free process. IOP Conf. Ser. Earth Environ. Sci., Vol. 460, Available at: https://doi.org/10.1088/1755-1315/460/1/012043.Search in Google Scholar
Baroi, C., Mahto, S., Niu, C., and Dalai, A.K. (2014). Biofuel production from green seed canola oil using zeolites. Appl. Catal. Gen. 469: 18–32, https://doi.org/10.1016/j.apcata.2013.09.034.Search in Google Scholar
Barros, F.J.S., Cecilia, J.A., Moreno-Tost, R., de Oliveira, M.F., Rodríguez-Castellón, E., Luna, F.M.T., and Vieira, R.S. (2020). Glycerol oligomerization using low cost dolomite catalyst. Waste Biomass Valorization 11: 1499–1512, https://doi.org/10.1007/s12649-018-0477-5.Search in Google Scholar
Bauer, F. and Hulteberg, C. (2013). Is there a future in glycerol as a feedstock in the production of biofuels and biochemicals? Biofuel. Bioprod. Biorefin. 7: 43–51, https://doi.org/10.1002/bbb.1370.Search in Google Scholar
Beatrice, C., Bertoli, C., and Giacomo, N.D. (1998). New findings on combustion behavior of oxygenated synthetic diesel fuels. Combust. Sci. Technol. 137: 31–50, https://doi.org/10.1080/00102209808952044.Search in Google Scholar
Beatrice, C., Di, G., Lazzaro, M., Cannilla, C., Bonura, G., Frusteri, F., Asdrubali, F., Baldinelli, G., Presciutti, A., Fantozzi, F., et al.. (2013). Technologies for energetic exploitation of biodiesel chain derived glycerol: oxy-fuels production by catalytic conversion. Appl. Energy 102: 63–71, doi:https://doi.org/10.1016/j.apenergy.2012.08.006.Search in Google Scholar
Bergendahl, J. (2007). Environmental issues of gasoline additives – aqueous solubility and spills. In: Letcher, M.T. (Ed.), Thermodynamics, solubility and environmental Issues. Elsevier, Amsterdam, pp. 245–258.10.1016/B978-044452707-3/50015-XSearch in Google Scholar
Bertels, E., Bruyninckx, K., Kurttepeli, M., Smet, M., Bals, S., and Goderis, B. (2014). Highly efficient hyperbranched CNT surfactants: influence of molar mass and functionalization. Langmuir 30: 12200–12209, https://doi.org/10.1021/la503032g.Search in Google Scholar PubMed
Bookong, P., Ruchirawat, S., and Boonyarattanakalin, S. (2015). Optimization of microwave-assisted etherification of glycerol to polyglycerols by sodium carbonate as catalyst. Chem. Eng. J. 275: 253–261, https://doi.org/10.1016/j.cej.2015.04.033.Search in Google Scholar
Boudou, J.-P., David, M.-O., Joshi, V., Eidi, H., and Curmi, P.A. (2013). Hyperbranched polyglycerol modified fluorescent nanodiamond for biomedical research. Diam. Relat. Mater. 38: 131–138, https://doi.org/10.1016/j.diamond.2013.06.019.Search in Google Scholar
Bozkurt, Ö.D., Tunç, F.M., Baʇlar, N., Çelebi, S., Günbaş, I.D., and Uzun, A. (2015). Alternative fuel additives from glycerol by etherification with isobutene: structure-performance relationships in solid catalysts. Fuel Process. Technol. 138: 780–804, https://doi.org/10.1016/j.fuproc.2015.06.047.Search in Google Scholar
Bozkurt, Ö.D., Yılmaz, F., Bağlar, N., Çelebi, S., and Uzun, A. (2019). Compatibility of di- and tri-tert-butyl glycerol ethers with gasoline. Fuel 255: 115767, https://doi.org/10.1016/j.fuel.2019.115767.Search in Google Scholar
Bradin, D., Grune, G.L., and Trivette, M. (2009). Alternative fuel and fuel additive compositions, Google Patents, January.10.1016/S1464-2859(09)70134-8Search in Google Scholar
Bradin, D.S. (1996). Biodiesel fuel, Google Patents, November.Search in Google Scholar
Calderón, M., Quadir, M.A., Sharma, S.K., and Haag, R. (2010). Dendritic polyglycerols for biomedical applications. Adv. Mater. 22: 190–218, https://doi.org/10.1002/adma.200902144.Search in Google Scholar
Cannilla, C., Bonura, G., Frusteri, L., and Frusteri, F. (2014a). Catalytic production of oxygenated additives by glycerol etherification. Cent. Eur. J. Chem. 12: 1248–1254, https://doi.org/10.2478/s11532-014-0546-y.Search in Google Scholar
Cannilla, C., Bonura, G., Frusteri, L., and Frusteri, F. (2014b). Glycerol etherification with TBA: high yield to poly-ethers using a membrane assisted batch reactor. Environ. Sci. Technol. 48: 6019–6026, https://doi.org/10.1021/es4053413.Search in Google Scholar
Cannilla, C., Bonura, G., Frusteri, L., and Frusteri, F. (2015). Batch reactor coupled with water permselective membrane: study of glycerol etherification reaction with butanol. Chem. Eng. J. 282: 187–193, https://doi.org/10.1016/j.cej.2015.03.013.Search in Google Scholar
Cannilla, C., Bonura, G., Maisano, S., Frusteri, L., Migliori, M., Giordano, G., Todaro, S., and Frusteri, F. (2020). Zeolite-assisted etherification of glycerol with butanol for biodiesel oxygenated additives production. J. Energy Chem. 48: 136–144, doi:https://doi.org/10.1016/j.jechem.2020.01.002.Search in Google Scholar
Cassel, S., Debaig, C., Benvegnu, T., Chaimbault, P., Lafosse, M., Plusquellec, D., and Rollin, P. (2001). Original synthesis of linear, branched and cyclic oligoglycerol standards. Eur. J. Org. Chem.: 875–896, https://doi.org/10.1002/1099-0690(200103)2001:5<875::aid-ejoc875>3.0.co;2-r.10.1002/1099-0690(200103)2001:5<875::AID-EJOC875>3.0.CO;2-RSearch in Google Scholar
Celdeira, P.A., Gonçalves, M., Figueiredo, F.C.A., Bosco, S.M.D., Mandelli, D., and Carvalho, W.A. (2014). Sulfonated niobia and pillared clay as catalysts in etherification reaction of glycerol. Appl. Catal. Gen. 478: 98–106, https://doi.org/10.1016/j.apcata.2014.03.037.Search in Google Scholar
Chen, D., Feng, H., and Li, J. (2012). Graphene oxide: preparation, functionalization, and electrochemical applications. Chem. Rev. 112: 6027–6053, https://doi.org/10.1021/cr300115g.Search in Google Scholar PubMed
Chiosso, M.E., Lick, I.D., Casella, M.L., and Merlo, A.B. (2020). Acid functionalized carbons as catalyst for glycerol etherification with benzyl alcohol. Braz. J. Chem. Eng. 37: 129–137, https://doi.org/10.1007/s43153-019-00002-z.Search in Google Scholar
Chong, C.C., Aqsha, A., Ayoub, M., Sajid, M., Abdullah, A.Z., Yusup, S., and Abdullah, B. (2020). A review over the role of catalysts for selective short-chain polyglycerol production from biodiesel derived waste glycerol. Environ. Technol. Innovat. 19: 100859, https://doi.org/10.1016/j.eti.2020.100859.Search in Google Scholar
Ciriminna, R., Katryniok, B., Paul, S., Dumeignil, F., and Pagliaro, M. (2015). Glycerol-derived renewable polyglycerols: a class of versatile chemicals of wide potential application. Org. Process Res. Dev. 19: 748–754, https://doi.org/10.1021/op500313x.Search in Google Scholar
Cornejo, A., Barrio, I., Campoy, M., Lázaro, J., and Navarrete, B. (2017). Oxygenated fuel additives from glycerol valorization. Main production pathways and effects on fuel properties and engine performance: a critical review. Renew. Sustain. Energy Rev. 79: 1400–1413, https://doi.org/10.1016/j.rser.2017.04.005.Search in Google Scholar
ten Dam, J. and Hanefeld, U. (2011). Renewable chemicals: dehydroxylation of glycerol and polyols. ChemSusChem 4: 1017–1034, https://doi.org/10.1002/cssc.201100162.Search in Google Scholar PubMed PubMed Central
Da Silva, M.J., Julio, A.A., Ferreira, S.O., Da Silva, R.C., and Chaves, D.M. (2019). Tin(II) phosphotungstate heteropoly salt: an efficient solid catalyst to synthesize bioadditives ethers from glycerol. Fuel 254: 115607, https://doi.org/10.1016/j.fuel.2019.06.015.Search in Google Scholar
Davies, T.E., Kondrat, S.A., Nowicka, E., Graham, J.J., Apperley, D.C., Taylor, S.H., and Graham, A.E. (2016). Dehydrative etherification reactions of glycerol with alcohols catalyzed by recyclable nanoporous aluminosilicates: telescoped routes to glyceryl ethers. ACS Sustain. Chem. Eng. 4: 835–843, https://doi.org/10.1021/acssuschemeng.5b00894.Search in Google Scholar
Demirbas, A. (2009). Political, economic and environmental impacts of biofuels: a review. Appl. Energy 86: S108–S117, https://doi.org/10.1016/j.apenergy.2009.04.036.Search in Google Scholar
Dominguez, C.M., Romero, A., and Santos, A. (2019). Improved etherification of glycerol with tert-butyl alcohol by the addition of dibutyl ether as solvent. Catalysts 9: 378, https://doi.org/10.3390/catal9040378.Search in Google Scholar
Drago, C., Liotta, L.F., La Parola, V., Testa, M.L., and Nicolosi, G. (2013). One-pot microwave assisted catalytic transformation of vegetable oil into glycerol-free biodiesel. Fuel 113: 707–711, https://doi.org/10.1016/j.fuel.2013.06.034.Search in Google Scholar
El Doukkali, M., Iriondo, A., and Gandarias, I. (2020). Enhanced catalytic upgrading of glycerol into high value-added H2 and propanediols: recent developments and future perspectives. Mol. Catal. 490: 110928.10.1016/j.mcat.2020.110928Search in Google Scholar
Ebadipour, N., Paul, S., Katryniok, B., and Dumeignil, F. (2020). Alkaline-based catalysts for glycerol polymerization reaction: a review. Catalysts 10: 1021, https://doi.org/10.3390/catal10091021.Search in Google Scholar
Estevez, R., Aguado-Deblas, L., Luna, D., and Bautista, F.M. (2019). An overview of the production of oxygenated fuel additives by glycerol etherification, either with isobutene or tert-butyl alcohol, over heterogeneous catalysts. Energies 12, https://doi.org/10.3390/en12122364.Search in Google Scholar
Estevez, R., Aguado-Deblas, L., Montes, V., Caballero, A., and Bautista, F.M. (2020). Sulfonated carbons from olive stones as catalysts in the microwave-assisted etherification of glycerol with tert-butyl alcohol. Mol. Catal. 488: 110921, https://doi.org/10.1016/j.mcat.2020.110921.Search in Google Scholar
Estevez, R., Iglesias, I., Luna, D., and Bautista, F.M. (2017a). Sulfonic acid functionalization of different zeolites and their use as catalysts in the microwave-assisted etherification of glycerol with tert-butyl alcohol. Molecules 22, https://doi.org/10.3390/molecules22122206.Search in Google Scholar PubMed PubMed Central
Estevez, R., Lopez-Pedrajas, S., Luna, D., and Bautista, F.M. (2017b). Microwave-assisted etherification of glycerol with tert-butyl alcohol over amorphous organosilica-aluminum phosphates. Appl. Catal. B Environ. 213: 42–52, https://doi.org/10.1016/j.apcatb.2017.05.007.Search in Google Scholar
Estevez, R., López, M.I., Jiménez-Sanchidrián, C., Luna, D., Romero-Salguero, F.J., and Bautista, F.M. (2016). Etherification of glycerol with tert-butyl alcohol over sulfonated hybrid silicas. Appl. Catal. Gen. 526: 155–163, https://doi.org/10.1016/j.apcata.2016.08.019.Search in Google Scholar
Fan, Z., Zhao, Y., Preda, F., Clacens, J.M., Shi, H., Wang, L., Feng, X., and Campo, F.D. (2015). Preparation of bio-based surfactants from glycerol and dodecanol by direct etherification. Green Chem. 17: 882–892, doi:https://doi.org/10.1039/c4gc00818a.Search in Google Scholar
Fang, W., Wang, S., Liebens, A., De Campo, F., Xu, H., Shen, W., Pera-Titus, M., and Clacens, J.M. (2015). Silica-immobilized Aquivion PFSA superacid: application to heterogeneous direct etherification of glycerol with n-butanol. Catal. Sci. Technol. 5: 3980–3990, doi:https://doi.org/10.1039/c5cy00534e.Search in Google Scholar
Figueiredo, F.C.A., Jordão, E., and Carvalho, W.A. (2008). Adipic ester hydrogenation catalyzed by platinum supported in alumina, titania and pillared clays. Appl. Catal. Gen. 351: 259–266, https://doi.org/10.1016/j.apcata.2008.09.027.Search in Google Scholar
Fischer, W., Quadir, M.A., Barnard, A., Smith, D.K., and Haag, R. (2011). Controlled release of DNA from photoresponsive hyperbranched polyglycerols with oligoamine shells. Macromol. Biosci. 11: 1736–1746, https://doi.org/10.1002/mabi.201100248.Search in Google Scholar PubMed
Frusteri, F., Cannilla, C., Bonura, G., Spadaro, L., Mezzapica, A., Beatrice, C., Di Blasio, G., and Guido, C. (2013). Glycerol ethers production and engine performance with diesel/ethers blend. Top. Catal. 56: 378–383, doi:https://doi.org/10.1007/s11244-013-9983-7.Search in Google Scholar
Frusteri, F., Frusteri, L., Cannilla, C., and Bonura, G. (2012). Catalytic etherification of glycerol to produce biofuels over novel spherical silica supported Hyflon® catalysts. Bioresour. Technol. 118: 350–358, https://doi.org/10.1016/j.biortech.2012.04.103.Search in Google Scholar PubMed
Frusteri, L., Cannilla, C., Bonura, G., Chuvilin, A.L., Perathoner, S., Centi, G., and Frusteri, F. (2016). Carbon microspheres preparation, graphitization and surface functionalization for glycerol etherification. Catal. Today 277: 68–77, https://doi.org/10.1016/j.cattod.2016.02.044.Search in Google Scholar
Gaharwar, A.K., Patel, A., Dolatshahi-Pirouz, A., Zhang, H., Rangarajan, K., Iviglia, G., Shin, S.-R., Hussain, M.A., and Khademhosseini, A. (2015). Elastomeric nanocomposite scaffolds made from poly(glycerol sebacate) chemically crosslinked with carbon nanotubes. Biomater. Sci. 3: 46–58, doi:https://doi.org/10.1039/c4bm00222a.Search in Google Scholar PubMed PubMed Central
Galhardo, T.S., Simone, N., Gonçalves, M., Figueiredo, F.C.A., Mandelli, D., and Carvalho, W.A. (2013). Preparation of sulfonated carbons from rice husk and their application in catalytic conversion of glycerol. ACS Sustain. Chem. Eng. 1: 1381–1389, https://doi.org/10.1021/sc400117t.Search in Google Scholar
García-Sancho, C., Moreno-Tost, R., Mérida-Robles, J.M., Santamaría-González, J., Jiménez-López, A., and Torres, P.M. (2011). Etherification of glycerol to polyglycerols over MgAl mixed oxides. Catal. Today 167: 84–90, https://doi.org/10.1016/j.cattod.2010.11.062.Search in Google Scholar
Gaudin, P., Jacquot, R., Marion, P., Pouilloux, Y., and Jérôme, F. (2011a). Homogeneously-catalyzed etherification of glycerol with 1-dodecanol. Catal. Sci. Technol. 1: 616–620, https://doi.org/10.1039/c1cy00082a.Search in Google Scholar
Gaudin, P., Jacquot, R., Marion, P., Pouilloux, Y., and Jérôme, F. (2011b). Acid-catalyzed etherification of glycerol with long-alkyl-chain alcohols. ChemSusChem 4: 719–722, https://doi.org/10.1002/cssc.201100129.Search in Google Scholar PubMed
Gheybi, H., Sattari, S., Bodaghi, A., Soleimani, K., Dadkhah, A., and Adeli, M. (2018). Polyglycerols – engineering of biomaterials for drug delivery systems: beyond polyethylene glycol, Available at: https://doi.org/10.1016/B978-0-08-101750-0.00005-2.Search in Google Scholar
Gholami, Z., Abdullah, A.Z., and Lee, K.-T. (2014a). Dealing with the surplus of glycerol production from biodiesel industry through catalytic upgrading to polyglycerols and other value-added products. Renew. Sustain. Energy Rev. 39: 327–341, https://doi.org/10.1016/j.rser.2014.07.092.Search in Google Scholar
Gholami, Z., Abdullah, A.Z., and Lee, K.T. (2014b). Heterogeneously catalyzed etherification of glycerol to diglycerol over calcium-lanthanum oxide supported on MCM-41: a heterogeneous basic catalyst. Appl. Catal. Gen. 479: 76–86, https://doi.org/10.1016/j.apcata.2014.04.024.Search in Google Scholar
Gholami, Z., Abdullah, A.Z., Gholami, F., and Vakili, M. (2015a). Modified silica-based heterogeneous catalysts for etherification of glycerol. AIP Conference Proceedings, Vol. 1669.10.1063/1.4919188Search in Google Scholar
Gholami, Z., Abdullah, A.Z., and Lee, K.T. (2015b). Catalytic etherification of glycerol to diglycerol over heterogeneous calcium-based mixed-oxide catalyst: reusability and stability. Chem. Eng. Commun. 202: 1397–1405, https://doi.org/10.1080/00986445.2014.952812.Search in Google Scholar
Gielen, D., Boshell, F., Saygin, D., Bazilian, M.D., Wagner, N., and Gorini, R. (2019). The role of renewable energy in the global energy transformation. Energy Strategy Rev. 24: 38–50, https://doi.org/10.1016/j.esr.2019.01.006.Search in Google Scholar
Gírio, F. (2019). Innovation on bioenergy. In: Lago, C., Caldés, N., and Lechón, Y. (Eds.), The role of bioenergy in the bioeconomy. Elsevier, Netherland, pp. 405–433.10.1016/B978-0-12-813056-8.00009-1Search in Google Scholar
Gonçalves, M., Souza, V.C., Galhardo, T.S., Mantovani, M., Figueiredo, F.C.A., Mandelli, D., and Carvalho, W.A. (2013). Glycerol conversion catalyzed by carbons prepared from agroindustrial wastes. Ind. Eng. Chem. Res. 52: 2832–2839, https://doi.org/10.1021/ie303072d.Search in Google Scholar
Goncalves, M., Castro, C.S., Oliveira, L.C.A., and Carvalho, W.A. (2015). Green acid catalyst obtained from industrial wastes for glycerol etherification. Fuel Process. Technol. 138: 695–703, https://doi.org/10.1016/j.fuproc.2015.07.010.Search in Google Scholar
Gonçalves, M., Soler, F.C., Isoda, N., Carvalho, W.A., Mandelli, D., and Sepúlveda, J. (2016). Glycerol conversion into value-added products in presence of a green recyclable catalyst: acid black carbon obtained from coffee ground wastes. J. Taiwan Inst. Chem. Eng. 60: 294–301, https://doi.org/10.1016/j.jtice.2015.10.016.Search in Google Scholar
Gonzalez-Arellano, C., Grau-Atienza, A., Serrano, E., Romero, A.A., Garcia-Martinez, J., and Luque, R. (2015). The role of mesoporosity and Si/Al ratio in the catalytic etherification of glycerol with benzyl alcohol using ZSM-5 zeolites. J. Mol. Catal. Chem. 406: 40–45, https://doi.org/10.1016/j.molcata.2015.05.011.Search in Google Scholar
González, M.D., Cesteros, Y., Llorca, J., and Salagre, P. (2012). Boosted selectivity toward high glycerol tertiary butyl ethers by microwave-assisted sulfonic acid-functionalization of SBA-15 and beta zeolite. J. Catal. 290: 202–209, https://doi.org/10.1016/j.jcat.2012.03.019.Search in Google Scholar
González, M.D., Cesteros, Y., and Salagre, P. (2013a). Establishing the role of Brønsted acidity and porosity for the catalytic etherification of glycerol with tert-butanol by modifying zeolites. Appl. Catal. Gen. 450: 178–188, https://doi.org/10.1016/j.apcata.2012.10.028.Search in Google Scholar
González, M.D., Salagre, P., Mokaya, R., and Cesteros, Y. (2014a). Tuning the acidic and textural properties of ordered mesoporous silicas for their application as catalysts in the etherification of glycerol with isobutene. Catal. Today 227: 171–178, https://doi.org/10.1016/j.cattod.2013.10.029.Search in Google Scholar
González, M.D., Salagre, P., Linares, M., García, R., Serrano, D., and Cesteros, Y. (2014b). Effect of hierarchical porosity and fluorination on the catalytic properties of zeolite beta for glycerol etherification. Appl. Catal. Gen. 473: 75–82, https://doi.org/10.1016/j.apcata.2013.12.038.Search in Google Scholar
González, M.D., Salagre, P., Taboada, E., Llorca, J., and Cesteros, Y. (2013b). Microwave-assisted synthesis of sulfonic acid-functionalized microporous materials for the catalytic etherification of glycerol with isobutene. Green Chem. 15: 2230–2239, https://doi.org/10.1039/c3gc40683k.Search in Google Scholar
González, M.D., Salagre, P., Taboada, E., Llorca, J., Molins, E., and Cesteros, Y. (2013c). Sulfonic acid-functionalized aerogels as high resistant to deactivation catalysts for the etherification of glycerol with isobutene. Appl. Catal. B Environ. 136–137: 287–293, https://doi.org/10.1016/j.apcatb.2013.02.018.Search in Google Scholar
Guerrero-Urbaneja, P., García-Sancho, C., Moreno-Tost, R., Mérida-Robles, J., Santamaría-González, J., Jiménez-López, A., and Maireles-Torres, P. (2014). Glycerol valorization by etherification to polyglycerols by using metal oxides derived from MgFe hydrotalcites. Appl. Catal. Gen. 470: 199–207, https://doi.org/10.1016/j.apcata.2013.10.051.Search in Google Scholar
He, Q. (Sophia), McNutt, J., and Yang, J. (2017). Utilization of the residual glycerol from biodiesel production for renewable energy generation. Renew. Sustain. Energy Rev. 71: 63–76, https://doi.org/10.1016/j.rser.2016.12.110.Search in Google Scholar
Huang, R. and Kim, E.Y. (2015). Catalytic synthesis of glycerol tert-butyl ethers as fuel additives from the biodiesel by-product glycerol. J. Chem.: 1–6, https://doi.org/10.1155/2015/763854.Search in Google Scholar
Ikizer, B., Oktar, N., and Dogu, T. (2015). Etherification of glycerol with C4 and C5 reactive olefins. Fuel Process. Technol. 138: 570–577, https://doi.org/10.1016/j.fuproc.2015.06.039.Search in Google Scholar
Izquierdo, J.F., Iniesta, E., Outón, P.R., and Izquierdo, M. (2017). Experimental study of glycerol etherification with C5 olefins to produce biodiesel additives. Fuel Process. Technol. 160: 1–7, https://doi.org/10.1016/j.fuproc.2017.02.011.Search in Google Scholar
Izquierdo, J.F., Montiel, M., Palés, I., Outón, P.R., Galán, M., Jutglar, L., Villarrubia, M., Izquierdo, M., Hermo, M.P., and Ariza, X. (2012). Fuel additives from glycerol etherification with light olefins: state of the art. Renew. Sustain. Energy Rev. 16: 6717–6724, doi:https://doi.org/10.1016/j.rser.2012.08.005.Search in Google Scholar
Izquierdo, J.F., Outón, P.R., Galán, M., Jutglar, L., Villarrubia, M., and Ariza, X. (2014). New biodiesel additives from glycerol and isoamylenes. Biofuel. Bioprod. Biorefin. 8: 658–669, https://doi.org/10.1002/bbb.1473.Search in Google Scholar
Izquierdo, J.F., Outón, P.R., Galán, M., Jutglar, L., Villarrubia, M., Hermo, M.P., Ariza, X., and Fernández, I. (2013). Ethers of glycerol and isoamylenes as biodiesel additives: synthesis and characterization. Chem. Eng. Trans. 32: 877–882.Search in Google Scholar
Jafari, M., Abolmaali, S.S., Najafi, H., and Tamaddon, A.M. (2020). Hyperbranched polyglycerol nanostructures for anti-biofouling, multifunctional drug delivery, bioimaging and theranostic applications. Int. J. Pharm. 576: 118959, https://doi.org/10.1016/j.ijpharm.2019.118959.Search in Google Scholar PubMed
Janaun, J. and Ellis, N. (2010). Glycerol etherification by tert-butanol catalyzed by sulfonated carbon catalyst. J. Appl. Sci. 10: 2633–2637, https://doi.org/10.3923/jas.2010.2633.2637.Search in Google Scholar
Jaworski, M.A., Rodríguez Vega, S., Siri, G.J., Casella, M.L., Romero Salvador, A., and Santos López, A. (2015). Glycerol etherification with benzyl alcohol over sulfated zirconia catalysts. Appl. Catal. Gen. 505: 36–43, https://doi.org/10.1016/j.apcata.2015.04.027.Search in Google Scholar
Katryniok, B., Paul, S., Bellière-Baca, V., Rey, P., and Dumeignil, F. (2010). Glycerol dehydration to acrolein in the context of new uses of glycerol. Green Chem. 12: 2079, https://doi.org/10.1039/c0gc00307g.Search in Google Scholar
Katryniok, B., Paul, S., and Dumeignil, F. (2013). Recent developments in the field of catalytic dehydration of glycerol to acrolein. ACS Catal. 3: 1819–1834, https://doi.org/10.1021/cs400354p.Search in Google Scholar
Khanna, S., Goyal, A., and Moholkar, V.S. (2012). Microbial conversion of glycerol: present status and future prospects. Crit. Rev. Biotechnol. 32: 235–262, https://doi.org/10.3109/07388551.2011.604839.Search in Google Scholar PubMed
Kirby, F., Nieuwelink, A.E., Kuipers, B.W.M., Kaiser, A., Bruijnincx, P.C.A., and Weckhuysen, B.M. (2015). CaO as drop-in colloidal catalysts for the synthesis of higher polyglycerols. Chem. Eur J. 21: 5101–5109, https://doi.org/10.1002/chem.201405906.Search in Google Scholar PubMed PubMed Central
Kubota, M., Sakamoto, A., Komatsu, M., Maeno, K., and Masuyama, A. (2014). Selective preparation of monobenzyl glyceryl ethers by the condensation reaction of glycerol with benzyl alcohols in the presence of zeolite catalysts. J. Oleo Sci. 63: 1057–1062, https://doi.org/10.5650/jos.ess13214.Search in Google Scholar PubMed
Lemos, C.O.T., Rade, L.L., Barrozo, M.A.D.S., Fernandes, L.D., Cardozo-Filho, L., and Hori, C.E. (2017). Optimization of catalytic glycerol etherification with ethanol in a continuous reactor. Energy Fuel. 31: 5158–5164, https://doi.org/10.1021/acs.energyfuels.7b00194.Search in Google Scholar
Lemos, C.O.T., Rade, L.L., Barrozo, M.A.d. S., Cardozo-Filho, L., and Hori, C.E. (2018). Study of glycerol etherification with ethanol in fixed bed reactor under high pressure. Fuel Process. Technol. 178: 1–6, https://doi.org/10.1016/j.fuproc.2018.05.015.Search in Google Scholar
Li, F., Jiang, X., Zhao, J., and Zhang, S. (2015a). Graphene oxide: a promising nanomaterial for energy and environmental applications. Nano Energy 16: 488–515, https://doi.org/10.1016/j.nanoen.2015.07.014.Search in Google Scholar
Li, X., Cai, T., Chen, C., and Chung, T. (2015b). Negatively charged hyperbranched polyglycerol grafted membranes for osmotic power generation from municipal wastewater. Water Res. 89: 50–58. https://doi.org/10.1016/j.watres.2015.11.032.Search in Google Scholar PubMed
Liao, X., Wang, S.G., Xiang, X., Zhu, Y., She, X., and Li, Y. (2012). SO 3H-functionalized ionic liquids as efficient catalysts for the synthesis of bioadditives. Fuel Process. Technol. 96: 74–79, https://doi.org/10.1016/j.fuproc.2011.11.025.Search in Google Scholar
Liu, F., De Oliveira Vigier, K., Pera-Titus, M., Pouilloux, Y., Clacens, J.M., Decampo, F., and Jérôme, F. (2013). Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids. Green Chem. 15: 901–909, https://doi.org/10.1039/c3gc36944g.Search in Google Scholar
Magar, S., Kamble, S., Mohanraj, G.T., Jana, S.K., and Rode, C. (2017). Solid-acid-catalyzed etherification of glycerol to potential fuel additives. Energy Fuel. 31: 1227–1277, https://doi.org/10.1021/acs.energyfuels.7b02213.Search in Google Scholar
Manjunathan, P., Kumar, M., Churipard, S.R., Sivasankaran, S., Shanbhag, G.V., and Maradur, S.P. (2016). Catalytic etherification of glycerol to tert-butyl glycerol ethers using tert-butanol over sulfonic acid functionalized mesoporous polymer. RSC Adv. 6: 82654–82660, https://doi.org/10.1039/c6ra18609b.Search in Google Scholar
Marchena, C.L., Frenzel, R.A., Gomez, S., Pierella, L.B., and Pizzio, L.R. (2013). Tungstophosphoric acid immobilized on ammonium Y and ZSM5 zeolites: synthesis, characterization and catalytic evaluation. Appl. Catal. B Environ. 130–131: 187–196, https://doi.org/10.1016/j.apcatb.2012.11.002.Search in Google Scholar
Martin, A. and Richter, M. (2011). Oligomerization of glycerol – a critical review. Eur. J. Lipid Sci. Technol. 113: 100–117, https://doi.org/10.1002/ejlt.201000386.Search in Google Scholar
Medeiros, M.A., Araujo, M.H., Augusti, R., Oliveira, L.C.A.de, and Lago, R.M. (2009). Acid-catalyzed oligomerization of glycerol investigated by electrospray ionization mass spectrometry. J. Braz. Chem. Soc. 20: 1667–1673, https://doi.org/10.1590/s0103-50532009000900015.Search in Google Scholar
Melero, J.A., Vicente, G., Morales, G., Paniagua, M., and Bustamante, J. (2018). Oxygenated compounds derived from glycerol for biodiesel formulation: influence on EN 14214 quality parameters. Fuel 89: 2011–2018, https://doi.org/10.1016/j.fuel.2010.03.042.Search in Google Scholar
Melero, J.A., Vicente, G., Paniagua, M., Morales, G., and Muñoz, P. (2012). Etherification of biodiesel-derived glycerol with ethanol for fuel formulation over sulfonic modified catalysts. Bioresour. Technol. 103: 142–151, https://doi.org/10.1016/j.biortech.2011.09.105.Search in Google Scholar
Mravec, D., Turan, A., Filková, A., Mikesková, N., Volkovicsová, E., Onyestyák, G., Harnos, S., Lónyi, F., Valyon, J., and Kaszonyi, A. (2017). Catalytic etherification of bioglycerol with bioethanol over H-beta, H-Y and H-MOR zeolites. Fuel Process. Technol. 159: 111–117, doi:https://doi.org/10.1016/j.fuproc.2017.01.012.Search in Google Scholar
Mufrodi, Z., Astuti, E., Budiman, A., and Prasetya, A. (2020). Utilization of glycerol from biodiesel industry by-product into several higher value products. In: Valorisation of agro-industrial residues. Volume II: Non-biological approaches. Springer, pp. 145–172.10.1007/978-3-030-39208-6_7Search in Google Scholar
Mukai, S., Lin, L., Masuda, T., and Hashimoto, K. (2001). Key factors for the encapsulation of Keggin-type heteropoly acids in the supercages of Y-type zeolite. Chem. Eng. Sci. 56: 799–804, https://doi.org/10.1016/s0009-2509(00)00291-8.Search in Google Scholar
Nakagawa, Y. and Tomishige, K. (2011). Heterogeneous catalysis of the glycerol hydrogenolysis. Catal. Sci. Technol. 1: 179, https://doi.org/10.1039/c0cy00054j.Search in Google Scholar
Nandiwale, K.Y., Patil, S.E., and Bokade, V.V. (2014). Glycerol etherification using n-butanol to produce oxygenated additives for biodiesel fuel over H-beta zeolite catalysts. Energy Technol. 2: 446–452, https://doi.org/10.1002/ente.201300169.Search in Google Scholar
Natural glycerine: a globally traded product. USP 99.7% purity kosher, natural glycerine: a large and expanding market .2021, Available at: https://naturalchem.com/glycerine (Accessed 13 June 2022).Search in Google Scholar
Nosal, H., Nowicki, J., Warzała, M., Nowakowska-bogdan, E., and Zar, M. (2015). Progress in organic coatings synthesis and characterization of alkyd resins based on Camelina sativa oil and polyglycerol. Prog. Org. Coat. 86: 59–70, https://doi.org/10.1016/j.porgcoat.2015.04.009.Search in Google Scholar
Noureddini, H. (2001). System and process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees fahrenheit, Google Patents, January.Search in Google Scholar
Oliveira, L.C.C. De, Barros, F.J.S., Moreno-tost, R., Cecilia, J.A., Ledesma-mu, A.L., Luna, F.M.T., and Vieira, R.S. (2017). Glycerol oligomers production by etherification using calcined eggshell as catalyst. Mol. Catal. 433: 282–290, https://doi.org/10.1016/j.mcat.2017.02.030.Search in Google Scholar
Ooi, X.Y., Gao, W., Ong, H.C., Lee, H.V., Juan, J.C., Chen, W.H., and Lee, K.T. (2019). Overview on catalytic deoxygenation for biofuel synthesis using metal oxide supported catalysts. Renew. Sustain. Energy Rev. 112: 834–852, https://doi.org/10.1016/j.rser.2019.06.031.Search in Google Scholar
Ozbay, N., Oktar, N., Dogu, G., and Dogu, T. (2013). Activity comparison of different solid acid catalysts in etherification of glycerol with tert-butyl alcohol in flow and batch reactors. Top. Catal. 56: 1790–1803, https://doi.org/10.1007/s11244-013-0116-0.Search in Google Scholar
Pariente, S., Tanchoux, N., and Fajula, F. (2009). Etherification of glycerol with ethanol over solid acid catalysts. Green Chem. 11: 1256, https://doi.org/10.1039/b905405g.Search in Google Scholar
Patel, A. (2013). Environmentally benign catalysts for clean organic reactions. Springer Dordrecht, New York.10.1007/978-94-007-6710-2Search in Google Scholar
Pepiotdesjardins, P., Pitsch, H., Malhotra, R., Kirby, S., and Boehman, A. (2008). Structural group analysis for soot reduction tendency of oxygenated fuels. Combust. Flame 154: 191–205, https://doi.org/10.1016/j.combustflame.2008.03.017.Search in Google Scholar
Pérez-Barrado, E., Pujol, M.C., Aguiló, M., Llorca, J., Cesteros, Y., Díaz, F., Pallarès, J., Marsal, L.F., and Salagre, P. (2015). Influence of acid-base properties of calcined MgAl and CaAl layered double hydroxides on the catalytic glycerol etherification to short-chain polyglycerols. Chem. Eng. J. 264: 547–556, doi:https://doi.org/10.1016/j.cej.2014.11.117.Search in Google Scholar
Pico, M.P., Rodríguez, S., Santos, A., and Romero, A. (2013a). Etherification of glycerol with benzyl alcohol. Ind. Eng. Chem. Res. 52: 14545–14555, https://doi.org/10.1021/ie402026t.Search in Google Scholar
Pico, M.P., Rosas, J.M., Rodríguez, S., Santos, A., and Romero, A. (2013b). Glycerol etherification over acid ion exchange resins: effect of catalyst concentration and reusability. J. Chem. Technol. Biotechnol. 88: 2027–2038, https://doi.org/10.1002/jctb.4063.Search in Google Scholar
Pinto, B.P., De Lyra, J.T., Nascimento, J.A.C., and Mota, C.J.A. (2016). Ethers of glycerol and ethanol as bioadditives for biodiesel. Fuel 168: 76–80, https://doi.org/10.1016/j.fuel.2015.11.052.Search in Google Scholar
Popeney, C.S., Setaro, A., Mutihac, R.-C., Bluemmel, P., Trappmann, B., Vonneman, J., Reich, S., and Haag, R. (2012). Polyglycerol-derived amphiphiles for the solubilization of single-walled carbon nanotubes in water: a structure-property study. ChemPhysChem 13: 203–211, doi:https://doi.org/10.1002/cphc.201100691.Search in Google Scholar PubMed
Quispe, C.A.G., Coronado, C.J.R., and Carvalho, J.A.Jr. (2013). Glycerol: production, consumption, prices, characterization and new trends in combustion. Renew. Sustain. Energy Rev. 27: 475–493, https://doi.org/10.1016/j.rser.2013.06.017.Search in Google Scholar
Ramos, M.J., Fernández, C.M., Casas, A., Rodríguez, L., and Pérez, Á. (2009). Influence of fatty acid composition of raw materials on biodiesel properties. Bioresour. Technol. 100: 261–268, https://doi.org/10.1016/j.biortech.2008.06.039.Search in Google Scholar PubMed
Rodrigues, R., Isoda, N., Gonçalves, M., Figueiredo, F.C.A., Mandelli, D., and Carvalho, W.A. (2012). Effect of niobia and alumina as support for Pt catalysts in the hydrogenolysis of glycerol. Chem. Eng. J. 198–199: 457–467, https://doi.org/10.1016/j.cej.2012.06.002.Search in Google Scholar
Ruppert, A.M., Meeldijk, J.D., Kuipers, B.W.M., Erné, B.H., and Weckhuysen, B.M. (2008). Glycerol etherification over highly active CaO-based materials: new mechanistic aspects and related colloidal particle formation. Chem. Eur J. 14: 2016–2024, https://doi.org/10.1002/chem.200701757.Search in Google Scholar PubMed
Ruppert, A.M., Parvulescu, A.N., Arias, M., Hausoul, P.J.C., Bruijnincx, P.C.A., Klein Gebbink, R.J.M., and Weckhuysen, B.M. (2009). Synthesis of long alkyl chain ethers through direct etherification of biomass-based alcohols with 1-octene over heterogeneous acid catalysts. J. Catal. 268: 251–259, https://doi.org/10.1016/j.jcat.2009.09.023.Search in Google Scholar
Saengarun, C., Petsom, A., and Tungasmita, D.N. (2017). Etherification of glycerol with propylene or 1-butene for fuel additives. Sci. World J.: 1–11, https://doi.org/10.1155/2017/4089036.Search in Google Scholar PubMed PubMed Central
Sajid, M., Ayoub, M., Uemura, Y., Yusup, S., Saleem, M., Abdullah, B., and Khan, A.U. (2019). Comparative study of glycerol conversion to polyglycerol via conventional and microwave irradiation reactor. Mater. Today Proc. 16: 2101–2107, https://doi.org/10.1016/j.matpr.2019.06.098.Search in Google Scholar
Salehpour, S. and Dubé, M.A. (2011). Towards the sustainable production of higher-molecular-weight polyglycerol. Macromol. Chem. Phys. 212: 1284–1293, https://doi.org/10.1002/macp.201100064.Search in Google Scholar
Samoilov, V.O., Borisov, R.S., Stolonogova, T.I., Zarezin, D.P., Maximov, A.L., Bermeshev, M.V., Chernysheva, E.A., and Kapustin, V.M. (2020). Glycerol to renewable fuel oxygenates. Part II: gasoline-blending characteristics of glycerol and glycol derivatives with C3-C4 alkyl(idene) substituents. Fuel 280: 118585, doi:https://doi.org/10.1016/j.fuel.2020.118585.Search in Google Scholar
Samoilov, V.O., Ramazanov, D.N., Nekhaev, A.I., and Maksimov, A.L. (2016a). Heterogeneous catalytic conversion of glycerol with n-butyl alcohol. Petrol. Chem. 56: 125–130, https://doi.org/10.1134/s0965544116010060.Search in Google Scholar
Samoilov, V.O., Ramazanov, D.N., Nekhaev, A.I., Maximov, A.L., and Bagdasarov, L.N. (2016b). Heterogeneous catalytic conversion of glycerol to oxygenated fuel additives. Fuel 172: 310–319, https://doi.org/10.1016/j.fuel.2016.01.024.Search in Google Scholar
Sangkhum, P., Yanamphorn, J., Wangriya, A., and Ngamcharussrivichai, C. (2019). Ca–Mg–Al ternary mixed oxides derived from layered double hydroxide for selective etherification of glycerol to short-chain polyglycerols. Appl. Clay Sci. 173: 79–87, https://doi.org/10.1016/j.clay.2019.03.006.Search in Google Scholar
Saxena, S.K., Al-Muhtaseb, A.H., and Viswanadham, N. (2015). Enhanced production of high octane oxygenates from glycerol etherification using the desilicated BEA zeolite. Fuel 159: 837–844, https://doi.org/10.1016/j.fuel.2015.07.028.Search in Google Scholar
Seiden, P. and Martin, J.B. (1976). Process for preparing polyblycerol, Google Patents, July.Search in Google Scholar
Sepúlveda, J.H., Vera, C.R., Yori, J.C., Badano, J.M., Santarosa, D., and Mandelli, D. (2011). H3PW12O40 (HPA), an efficient and reusable catalyst for biodiesel production related reactions. Esterification of oleic acid and etherification of glycerol. Quim. Nova 34: 601–606, https://doi.org/10.1590/s0100-40422011000400009.Search in Google Scholar
Shalaby, S.W. and Johnson, R.A. (1994). Synthetic absorbable polyesters. In: Shalaby, S.W. (Ed.), Biomedical polymers. München: Carl Hanser Verlag.Search in Google Scholar
Shinde, K. and Kaliaguine, S. (2019). A comparative study of ultrasound biodiesel production using different homogeneous catalysts. ChemEngineering 3: 18, https://doi.org/10.3390/chemengineering3010018.Search in Google Scholar
Simone, N., Carvalho, W.A., Mandelli, D., and Ryoo, R. (2016). Nanostructured MFI-type zeolites as catalysts in glycerol etherification with tert-butyl alcohol. J. Mol. Catal. Chem. 422: 115–121, https://doi.org/10.1016/j.molcata.2016.02.005.Search in Google Scholar
Singh, A.K., Nguyen, R., Galy, N., Haag, R., Sharma, S.K., and Len, C. (2016). Chemo-enzymatic synthesis of oligoglycerol derivatives. Molecules 21: 1–12, https://doi.org/10.3390/molecules21081038.Search in Google Scholar PubMed PubMed Central
Sisson, A.L. and Haag, R. (2010). Polyglycerol nanogels: highly functional scaffolds for biomedical applications. Soft Matter 6: 4968, https://doi.org/10.1039/c0sm00149j.Search in Google Scholar
Sivaiah, M.V., Robles-Manuel, S., Valange, S., and Barrault, J. (2012). Recent developments in acid and base-catalyzed etherification of glycerol to polyglycerols. Catal. Today 198: 305–313, https://doi.org/10.1016/j.cattod.2012.04.073.Search in Google Scholar
Son, S., Shin, E., and Kim, B.-S. (2014). Light-responsive micelles of spiropyran initiated hyperbranched polyglycerol for smart drug delivery. Biomacromolecules 15: 628–634, https://doi.org/10.1021/bm401670t.Search in Google Scholar PubMed
Srinivas, M., Raveendra, G., Parameswaram, G., Prasad, P.S.S., and Lingaiah, N. (2016). Cesium exchanged tungstophosphoric acid supported on tin oxide: an efficient solid acid catalyst for etherification of glycerol with tert-butanol to synthesize biofuel additives. J. Mol. Catal. Chem. 413: 7–14, https://doi.org/10.1016/j.molcata.2015.10.005.Search in Google Scholar
Srinivas, M., Raveendra, G., Parameswaram, G., Sai Prasad, P.S., Loridant, S., and Lingaiah, N. (2015). Understanding the surface and structural characteristics of tungsten oxide supported on tin oxide catalysts for the conversion of glycerol. J. Chem. Sci. 127: 897–908, https://doi.org/10.1007/s12039-015-0848-4.Search in Google Scholar
Srinivas, M., Sree, R., Raveendra, G., Kumar, C.R., Prasad, P.S.S., and Lingaiah, N. (2014). Selective etherification of glycerol with tert-butanol over 12-tungstophosphoric acid catalysts supported on Y-zeolite. Indian J. Chem. 53: 524–529.Search in Google Scholar
Sun, D., Yamada, Y., Sato, S., and Ueda, W. (2016). Glycerol hydrogenolysis into useful C3 chemicals. Appl. Catal. B Environ. 193: 75–92, https://doi.org/10.1016/j.apcatb.2016.04.013.Search in Google Scholar
Sutter, M., Silva, E. Da, Duguet, N., Raoul, Y., Métay, E., and Lemaire, M. (2015). Glycerol ether synthesis: a bench test for green chemistry concepts and technologies. Chem. Rev. 115: 8609–8651, https://doi.org/10.1021/cr5004002.Search in Google Scholar PubMed
Tan, S.X., Lim, S., Ong, H.C., and Pang, Y.L. (2019). State of the art review on development of ultrasound-assisted catalytic transesterification process for biodiesel production. Fuel 235: 886–907, https://doi.org/10.1016/j.fuel.2018.08.021.Search in Google Scholar
Tiwari, M.S., Dicks, J.S., Keogh, J., Ranade, V.V., and Manyar, H.G. (2020). Direct conversion of furfuryl alcohol to butyl levulinate using tin exchanged tungstophosphoric acid catalysts. Mol. Catal. 488: 110918, https://doi.org/10.1016/j.mcat.2020.110918.Search in Google Scholar
Tiwari, M.S. and Yadav, G.D. (2015). Kinetics of Friedel–crafts benzoylation of veratrole with benzoic anhydride using Cs2.5H0.5PW12O40/K-10 solid acid catalyst. Chem. Eng. J. 266: 64–73, https://doi.org/10.1016/j.cej.2014.12.043.Search in Google Scholar
Tiwari, M.S. and Yadav, G.D. (2016). Novel aluminium exchanged dodecatungstophosphoric acid supported on K-10 clay as catalyst: benzoylation of diphenyloxide with benzoic anhydride. RSC Adv. 6: 49091–49100, https://doi.org/10.1039/c6ra05379c.Search in Google Scholar
Tiwari, M.S., Jain, T., and Yadav, G.D. (2017a). Novel bifunctional palladium-dodecatungstophosphoric acid supported on titania nanotubes: one-pot synthesis of n- pentyl tetrahydrofurfuryl ether from furfuryl alcohol and n-pentanol. Ind. Eng. Chem. Res 56: 12909–12919, https://doi.org/10.1021/acs.iecr.7b00078.Search in Google Scholar
Tiwari, M.S., Gawade, A.B., and Yadav, G.D. (2017b). Magnetically separable sulfated zirconia as highly active acidic catalysts for selective synthesis of ethyl levulinate from furfuryl alcohol. Green Chem. 19: 963–976, https://doi.org/10.1039/c6gc02466a.Search in Google Scholar
Turan, A., Hrivnák, M., Klepáčová, K., Kaszonyi, A., and Mravec, D. (2013). Catalytic etherification of bioglycerol with C4 fraction. Appl. Catal. Gen. 468: 313–321, https://doi.org/10.1016/j.apcata.2013.09.007.Search in Google Scholar
Veiga, P.M., Gomes, A.C.L., Veloso, C.O., and Henriques, C.A. (2017)., Vol. 548. Elsevier, pp. 2–15.Acid zeolites for glycerol etherification with ethyl alcohol: catalytic activity and catalyst propertiesAppl. Catal. Gen.10.1016/j.apcata.2017.06.042Search in Google Scholar
Veluturla, S., Archna, N., Subba Rao, D., Hezil, N., Indraja, I.S., and Spoorthi, S. (2018). Catalytic valorization of raw glycerol derived from biodiesel: a review. Biofuels 9: 305–314, https://doi.org/10.1080/17597269.2016.1266234.Search in Google Scholar
Versteeg, G.F. and Wermink, W.N. (2020). Gtbe compositions, methods and installations for enhanced octane boosting. Google Patents, March.Search in Google Scholar
Viswanadham, N. and Saxena, S.K. (2013). Etherification of glycerol for improved production of oxygenates. Fuel 103: 980–986, https://doi.org/10.1016/j.fuel.2012.06.057.Search in Google Scholar
Voicu, V., Bombos, D., Bolocan, I., Jang, C.R., and Ciuparu, D. (2012). The influence of the character of emulsifiers on the performance of H 4SiW12O40.30H2O heteropolyacid catalyst in glycerol etherification with isobutene. Rev. Chem. 63: 200–204.Search in Google Scholar
Wessendorf, R.D. and Graf, W. (1996). Process for the preparation of polyol alkyl ethers, EP0718270A2.Search in Google Scholar
Wilms, D., Stiriba, S.-E., and Frey, H. (2010). Hyperbranched polyglycerols: from the controlled synthesis of biocompatible polyether polyols to multipurpose applications. Acc. Chem. Res. 43: 129–141, https://doi.org/10.1021/ar900158p.Search in Google Scholar PubMed
Xiao, L., Mao, J., Zhou, J., Guo, X., and Zhang, S. (2011). Enhanced performance of HY zeolites by acid wash for glycerol etherification with isobutene. Appl. Catal. Gen. 393: 88–95, https://doi.org/10.1016/j.apcata.2010.11.029.Search in Google Scholar
Yang, Z., Huang, R., Qi, W., Tong, L., Su, R., and He, Z. (2015). Hydrolysis of cellulose by sulfonated magnetic reduced graphene oxide. Chem. Eng. J. 280: 90–98, https://doi.org/10.1016/j.cej.2015.05.091.Search in Google Scholar
Yu, W., Sisi, L., Haiyan, Y., and Jie, L. (2020). Progress in the functional modification of graphene/graphene oxide: a review. RSC Adv. 10: 15328–15345, https://doi.org/10.1039/d0ra01068e.Search in Google Scholar PubMed PubMed Central
Yuan, Z., Xia, S., Chen, P., Hou, Z., and Zheng, X. (2011). Etherification of biodiesel-based glycerol with bioethanol over tungstophosphoric acid to synthesize glyceryl ethers. Energy Fuel. 25: 3186–3191, https://doi.org/10.1021/ef200366q.Search in Google Scholar
Zafari, R. and Kharat, A.N. (2018). Evaluation of mesoporous modified ferrierite zeolite performance in production of diglycerol from glycerol. Rev. Roum. Chem. 63: 95–101.Search in Google Scholar
Zamboulis, A., Nakiou, E.A., Christodoulou, E., Bikiaris, D.N., Kontonasaki, E., Liverani, L., and Boccaccini, A.R. (2019). Polyglycerol hyperbranched polyesters: synthesis, properties and pharmaceutical and biomedical applications. Int. J. Mol. Sci. 20: 6210, https://doi.org/10.3390/ijms20246210.Search in Google Scholar PubMed PubMed Central
Zhao, W., Yang, B., Yi, C., Lei, Z., and Xu, J. (2010). Etherification of glycerol with isobutylene to produce oxygenate additive using sulfonated peanut shell catalyst. Ind. Eng. Chem. Res. 49: 12399–12404, https://doi.org/10.1021/ie101461g.Search in Google Scholar
Zhao, W., Yi, C., Yang, B., Hu, J., and Huang, X. (2013). Etherification of glycerol and isobutylene catalyzed over rare earth modified Hβ-zeolite. Fuel Process. Technol. 112: 70–75, https://doi.org/10.1016/j.fuproc.2013.02.012.Search in Google Scholar
Zhou, C.-H., Clayton), Beltramini, J.N., Fan, Y.-X., and Lu, G.Q. (Max) (2008). Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem. Soc. Rev. 37: 527–549, https://doi.org/10.1039/b707343g.Search in Google Scholar PubMed
Zhou, J., Wang, Y., Guo, X., Mao, J., and Zhang, S. (2014). Etherification of glycerol with isobutene on sulfonated graphene: reaction and separation. Green Chem. 16: 4669–4679, https://doi.org/10.1039/c4gc01044b.Search in Google Scholar
Ziolek, M., Decyk, P., Sobczak, I., Trejda, M., Florek, J., Klimas, H.G.W., and Wojtaszek, A. (2011). Catalytic performance of niobium species in crystalline and amorphous solids — gas and liquid phase oxidation. Appl. Catal. Gen. 391: 194–204, https://doi.org/10.1016/j.apcata.2010.07.022.Search in Google Scholar
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