Process intensification of microwave-assisted acetylation reaction of glycerol to synthesize fuel additives using porcine pancreas lipase catalyst

References

• Charles C, Gerasimchuk I, Bridle R, et al. Biofuels—at what cost? A review of costs and benefits of EU biofuel policies. International Institute for Sustainable Development (IISD); Research report; 2013. p. 1–129.
   Google Scholar
• Pradima J, Kulkarni, RM. Review on enzymatic synthesis of value added products of glycerol, a by-product derived from biodiesel production. Resour Effic Technol. 2017;3(4):394–405. doi: 10.1016/j.reffit.2017.02.009.
   Google Scholar
• Zheng Y, Chen X, Shen Y. Commodity chemicals derived from glycerol, an important biorefinery feedstock. Chem Rev. 2008;108(12):5253–5277. doi: 10.1021/cr068216s.
   PubMed Web of Science ®Google Scholar
• Carraretto C, Macor A, Mirandola A, et al. Biodiesel as alternative fuel: experimental analysis and energetic evaluations. Energy. 2004;29(12–15):2195–2211. doi: 10.1016/j.energy.2004.03.042.
   Web of Science ®Google Scholar
• Khayoon MS, Hameed BH. Acetylation of glycerol to biofuel additives over sulfated activated carbon catalyst. Bioresour Technol. 2011;102(19):9229–9235. doi: 10.1016/j.biortech.2011.07.035.
   PubMed Web of Science ®Google Scholar
• Dalla Costa BO, Decolatti HP, Legnoverde MS, et al. Influence of acidic properties of different solid acid catalysts for glycerol acetylation. Catal Today. 2017;289:222–230. doi: 10.1016/j.cattod.2016.09.015.
   Web of Science ®Google Scholar
• Liu J, Wang Z, Sun Y, et al. Selective synthesis of triacetin from glycerol catalyzed by HZSM-5/MCM-41 micro/mesoporous molecular sieve. Chin J Chem Eng. 2019;27(5):1073–1078. doi: 10.1016/j.cjche.2018.09.013.
   Web of Science ®Google Scholar
• Balaraju M, Nikhitha P, Jagadeeswaraiah K, et al. Acetylation of glycerol to synthesize bioadditives over niobic acid supported tungstophosphoric acid catalysts. Fuel Process Technol. 2010;91(2):249–253. doi: 10.1016/j.fuproc.2009.10.005.
   Web of Science ®Google Scholar
• Jagadeeswaraiah K, Balaraju M, Prasad PS, et al. Selective esterification of glycerol to bioadditives over heteropoly tungstate supported on Cs-containing zirconia catalysts. Appl Catal A. 2010;386(1–2):166–170. doi: 10.1016/j.apcata.2010.07.046.
   Web of Science ®Google Scholar
• Zhu S, Zhu Y, Gao X, et al. Production of bioadditives from glycerol esterification over zirconia supported heteropolyacids. Bioresour Technol. 2013;130:45–51. doi: 10.1016/j.biortech.2012.12.011.
   PubMed Web of Science ®Google Scholar
• Soares Dias AP, Gomes Fonseca F, Catarino M, et al. Biodiesel glycerin valorization into oxygenated fuel additives. Catal Lett. 2022;152(2):513–522. doi: 10.1007/s10562-021-03646-0.
   Web of Science ®Google Scholar
• Pradima J, Rajeswari MK, Archna N, et al. Synthesis of acetins from glycerol using lipase from wheat extract. Korean Chem Eng Res. 2019;57(4):501–506.
   Web of Science ®Google Scholar
• Chipley JR. Effects of microwave irradiation on microorganisms. Adv Appl Microbiol. 1980;26:129–145. doi: 10.1016/s0065-2164(08)70333-2.
   PubMedGoogle Scholar
• Li H, Zhang C, Pang C, et al. The advances in the special microwave effects of the heterogeneous catalytic reactions. Front Chem. 2020;8:355. doi: 10.3389/fchem.2020.00355.
   PubMed Web of Science ®Google Scholar
• Wang L, Zhang Y, Zhang Y, et al. Synthesis of 2-ethylhexyl palmitate catalyzed by enzyme under microwave. Appl Biochem Biotechnol. 2018;185(1):347–356. doi: 10.1007/s12010-017-2666-2.
   PubMed Web of Science ®Google Scholar
• Yadav GD, Devendran S. Microwave assisted enzyme catalysis: practice and perspective. White Biotechnol Sustain Chem. 2015;52–102.
   Google Scholar
• Appaturi JN, Maireles-Torres P, Alomar TS, et al. Highly active nickel (II) oxide-supported cerium oxide catalysts for valorization of glycerol into oxygenated fuel additives. Materials. 2023;16(13):4713. doi: 10.3390/ma16134713.
   PubMed Web of Science ®Google Scholar
• Magar SB, Tiwari AK, Pal DB, et al. Biomass conversion: production of oxygenated fuel additives. In: Recent technologies for waste to clean energy and its utilization. Singapore: Springer Nature Singapore; 2023.p. 219–244.
   Google Scholar
• Uchenna AF, Irmawati R, Taufiq-Yap YH, et al. Glycerol acetylation over yttrium oxide (Y2O3) catalyst supported on palm kernel shell-derived carbon and parameters optimization studies using response surface methodology (RSM). Arab J Chem. 2023;16(8):104865. doi: 10.1016/j.arabjc.2023.104865.
   Web of Science ®Google Scholar
• Farisya Shera MR, Irmawati R, Shafizah IN, et al. Assessment on the effect of sulfuric acid concentration on physicochemical properties of sulfated-titania catalyst and glycerol acetylation performance. Catalysts. 2021;11(12):1542. doi: 10.3390/catal11121542.
   Web of Science ®Google Scholar
• Spataru D, Dias APS, Ferreira LFV. Acetylation of biodiesel glycerin using glycerin and glucose derived catalysts. J Clean Prod. 2021;297:126686. doi: 10.1016/j.jclepro.2021.126686.
   Web of Science ®Google Scholar
• Banu I, Bumbac G, Bombos D, et al. Glycerol acetylation with acetic acid over purolite CT-275. Product yields and process kinetics. Renew Energy. 2020;148:548–557. doi: 10.1016/j.renene.2019.10.060.
   Web of Science ®Google Scholar
• Goscianska J, Malaika A. A facile post-synthetic modification of ordered mesoporous carbon to get efficient catalysts for the formation of acetins. Catal Today. 2020;357:84–93. doi: 10.1016/j.cattod.2019.02.049.
   Web of Science ®Google Scholar
• Dill LP, Kochepka DM, Melinski A, et al. Microwave-irradiated acetylation of glycerol catalyzed by acid activated clays. Reac Kinet Mech Cat. 2019;127(2):991–1004. doi: 10.1007/s11144-019-01594-w.
   Web of Science ®Google Scholar
• Khan N, Khan MU, Siddiqui ZN. Selective esterification of glycerol over ionic liquid functionalized cellulose (IMD-Si/HSO4@ cellulose) under energy-efficient microwave irradiation. Mater Adv. 2022;3(9):3972–3979. doi: 10.1039/D1MA00889G.
   Google Scholar
• Marwan M, Indarti E, Darmadi D, et al. Production of triacetin by microwave assisted esterification of glycerol using activated natural zeolite. Bull Chem React Eng Catal. 2019;14(3):672–677. doi: 10.9767/bcrec.14.3.4250.672-677.
   Web of Science ®Google Scholar
• San Kong P, Aroua MK, Daud WMAW, et al. Enhanced microwave catalytic-esterification of industrial grade glycerol over Brønsted-based methane sulfonic acid in production of biolubricant. Process Saf Environ Protec. 2016;104:323–333. doi: 10.1016/j.psep.2016.09.014.
   Web of Science ®Google Scholar
• Zappaterra F, Summa D, Semeraro B, et al. Enzymatic esterification as potential strategy to enhance the sorbic acid behavior as food and beverage preservative. Fermentation. 2020;6(4):96. doi: 10.3390/fermentation6040096.
   Google Scholar
• More SB, Waghmare JT, Gogate PR. Ultrasound pretreatment as a novel approach for intensification of lipase catalyzed esterification of tricaprylin. Ultrason Sonochem. 2017;36:253–261. doi: 10.1016/j.ultsonch.2016.11.036.
   PubMed Web of Science ®Google Scholar
• Oh S, Park C. Enzymatic production of glycerol acetate from glycerol. Enzyme Microb Technol. 2015;69:19–23. doi: 10.1016/j.enzmictec.2014.11.004.
   PubMed Web of Science ®Google Scholar
• Cushing KA, Peretti SW. Enzymatic processing of renewable glycerol into value-added glycerol carbonate. RSC Adv. 2013;3(40):18596–18604. doi: 10.1039/c3ra43811b.
   Web of Science ®Google Scholar
• Dhake KP, Deshmukh KM, Wagh YS, et al. Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non-aqueous reaction medium. J Mol Catal B Enzym. 2012;77:15–23. doi: 10.1016/j.molcatb.2012.01.009.
   Google Scholar
• Yesiloglu Y, Kilic I. Lipase‐catalyzed esterification of glycerol and oleic acid. J Am Oil Chem Soc. 2004;81(3):281–284. doi: 10.1007/s11746-004-0896-5.
   Web of Science ®Google Scholar
• Fang Y, Sun SY, Xia YM. The weakened 1,3-specificity in the consecutive microwave assisted enzymatic synthesis of glycerides. J Mol Catal B Enzym. 2008;55(1–2):6–11. doi: 10.1016/j.molcatb.2008.01.001.
   Google Scholar
• Britto PJ, Kulkarni RM, Veluturla S, et al. Application of steapsin lipase for bioconversion of glycerol acetates from glycerol. Biocatal Agric Biotechnol. 2023;48:102641. doi: 10.1016/j.bcab.2023.102641.
   Web of Science ®Google Scholar
• de Sousa Junior PG, do Nascimento Camara AG, Oliveira ART, et al. Optimization and theoretical analysis of lipase-catalyzed enzymatic esterification of glycerol for efficient glycerides synthesis. Biochem Eng J. 2023;198:109033. doi: 10.1016/j.bej.2023.109033.
   Web of Science ®Google Scholar
• Jadhav H, Annapure U. Greener route for intensified synthesis of tricaprylin using amberlyst-15. J Chem Sci. 2021;133(1):1–7. doi: 10.1007/s12039-020-01869-z.
   Web of Science ®Google Scholar
• Farias da Costa AA, de Nazaré de Oliveira A, Esposito R, et al. Glycerol and microwave-assisted catalysis: recent progresses in batch and flow devices. Sustain Energy Fuels. 2023;7(8):1768–1792. doi: 10.1039/D2SE01647H.
   Web of Science ®Google Scholar
• Lanjekar K, Rathod VK. Utilization of glycerol for the production of glycerol carbonate through greener route. J Environ Chem Eng. 2013;1(4):1231–1236. doi: 10.1016/j.jece.2013.09.015.
   Google Scholar
• Agirre I, Güemez MB, Ugarte A, et al. Glycerol acetals as diesel additives: kinetic study of the reaction between glycerol and acetaldehyde. Fuel Process Technol. 2013;116:182–188. doi: 10.1016/j.fuproc.2013.05.014.
   Web of Science ®Google Scholar
• Laane C, Boeren S, Vos K, et al. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng. 1987;30(1):81–87. doi: 10.1002/bit.260300112.
   PubMed Web of Science ®Google Scholar
• Smallwood I. Handbook of organic solvent properties. Butterworth-Heinemann; 2012.
   Google Scholar
• Yadav GD, Borkar IV. Kinetic and mechanistic investigation of microwave-assisted lipase catalyzed synthesis of citronellyl acetate. Ind Eng Chem Res. 2009;48(17):7915–7922. doi: 10.1021/ie800591c.
   Web of Science ®Google Scholar
• Yadav GD, Devendran S. Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium. Process Biochem. 2012;47(3):496–502. doi: 10.1016/j.procbio.2011.12.008.
   Web of Science ®Google Scholar
• Kulkarni RM, Britto PJ, Narula A, et al. Kinetic studies on the synthesis of fuel additives from glycerol using CeO2–ZrO2 metal oxide catalyst. Biofuel Res J. 2020;7(1):1100–1108. doi: 10.18331/BRJ2020.7.1.2.
   Web of Science ®Google Scholar
• Mendes AA, Oliveira PC, de Castro HF. Properties and biotechnological applications of porcine pancreatic lipase. J Mol Catal B Enzym. 2012;78:119–134. doi: 10.1016/j.molcatb.2012.03.004.
   Web of Science ®Google Scholar
• Liao X, Zhu Y, Wang SG, et al. Producing triacetyl glycerol with glycerol by two steps: esterification and acetylation. Fuel Process Technol. 2009;90(7–8):988–993. doi: 10.1016/j.fuproc.2009.03.015.
   Web of Science ®Google Scholar