Obtaining hydrolysate from macauba oil and its application in the production of methyl esters

D.T.  Raspe; N.  Stevanato; T.B.  Massa; C.  Silva

doi:10.3989/gya.0453211

Authors

D.T. Raspe Centro de Ciências Agrárias, Universidade Estadual de Maringá (UEM) https://orcid.org/0000-0003-1173-8636
N. Stevanato Departamento de Engenharia Química, Universidade Estadual de Maringá (UEM) https://orcid.org/0000-0001-5536-9524
T.B. Massa Departamento de Engenharia Química, Universidade Estadual de Maringá (UEM) https://orcid.org/0000-0002-1733-4547
C. Silva Departamento de Engenharia Química, Universidade Estadual de Maringá (UEM) - Departamento de Tecnologia, Universidade Estadual de Maringá (UEM) https://orcid.org/0000-0002-7989-7046

DOI:

https://doi.org/10.3989/gya.0453211

Keywords:

Enzymatic catalysis, Esterification, Hydrolysis, Macauba oil, Methyl esters

Abstract

This work aimed to obtain a hydrolyzate rich in free fatty acids (FFA) from the hydrolysis of macauba oil for subsequent esterification and obtaining of methyl esters. To determine the conditions that maximize FFA yield in the hydrolysis step, the effects of buffer solution percentage and catalyst concentration (Lipozyme^® RM IM) were determined at 55 ºC and 6 h. From the results, it was verified that both variables evaluated in the experimental range had an influence on the reaction and their increase favored the production of FFA. Additional experiments were carried out to assess the influence of reaction time with a progressive increase up to 8 h. Hydrolyzate with ~92 wt % FFA was obtained and its use in the enzymatic esterification step using Novozym® 435 as catalyst resulted in ~95 % FFA conversion. Regarding the reuse of enzymes at each stage, a ~50 % reduction in FFA yield was found and only 98 % FFA conversion.

Downloads

Download data is not yet available.

References

ANP, Agência Nacional de Petróleo, Gás Natural e Biocombustíveis. 2015. Boletim mensal de biodiesel.

AOCS, American Oil Chemists' Society. 1998. Official methods and recommended practices. 2, 4 (Ed.) Champaign.

Baek Y, Lee J, Son J, Leem T, Sobhan A, Lee J, Koo SM, Shin WH, Oh JM, Park C. 2020. Enzymatic Synthesis of Formate Ester through Immobilized Lipase and Its Reuse. Polym. 12, 1-10. https://doi.org/10.3390/polym12081802 PMid:32796735 PMCid:PMC7465053

Bankovic-Llic O, Stamenkovic OS, Velikovic VB. 2012. Biodiesel production from non-edible plant oils. Renew. Sust. Ener. Ver. 16, 3621-3647. https://doi.org/10.1016/j.rser.2012.03.002

Barbosa MS, Freire CCC, Almeida LC, Freitas LS, Souza RL, Pereira EB, Mendes AA, Pereira MM, Lima AS, Soares CMF. 2019. Optimization of the enzymatic hydrolysis of Moringa oleifera Lam oil using molecular docking analysis for fatty acid specificity. Biotechnol. Appl. Biochem. 66, 823-832. https://doi.org/10.1002/bab.1793 PMid:31206795

Cerveró JM, Álvarez JR, Luque S. 2014. Novozym 435-catalyzed synthesis of fatty acid ethyl esters from soybean oil for biodiesel production. Biomass Bioenerg. 61, 131-137. https://doi.org/10.1016/j.biombioe.2013.12.005

Chowdhury A, Mitra D. 2015. A kinetic study on the Novozyme 435-catalyzed esterification of free fatty acids with octanol to produce octyl esters. Biotechnol. Prog. 31, 1494-1499. https://doi.org/10.1002/btpr.2165 PMid:26334440

Cocks LV, Van Rede C. 1966. Laboratory Handbook for Oil and Fat Analysis. Londres. Acad. Press.

Corradini FAS, Alves ES, Kopp W, Ribeiro MPA, Mendes AA, Tardioli PW, Giordano RC, Giordano RLC. 2019. Kinetic study of soybean oil hydrolysis catalyzed by lipase from solid castor bean seeds. Chem. Eng. Res. Des. 144, 115-122. https://doi.org/10.1016/j.cherd.2019.02.008

Doukyu N, Ogino H. 2010. Organic solvent-tolerant enzymes. Biochem. Eng. J. 48, 270-282. https://doi.org/10.1016/j.bej.2009.09.009

Kabbashi NA, Mohammed NI, Alam MZ, Mirghani MES. 2015. Hydrolysis of Jatropha curcas oil for biodiesel synthesis using immobilized Candida cylindracea lipase. J. Mol. Catal. B. Enzym. 116, 95-100. https://doi.org/10.1016/j.molcatb.2015.03.009

Lam MK, Jamalluddin NA, Lee KT. 2019. Production of Biodiesel Using Palm Oil. Biofuels: Alternative Feedstocks and Conversion Processes for the Production of Liquid and Gaseous Biofuels. Biomass Biofuels Biochem. 2, 539-574. https://doi.org/10.1016/B978-0-12-816856-1.00023-3

Manfio CE, Motoike SY, Pimentel LD, de Queiroz V, Sato AY. 2011. Repetibilidade em características biométricas do fruto de macaúba. Cienc. Rural 41, 70-76. https://doi.org/10.1590/S0103-84782011000100012

McClements DJ, Weiss J. 2005. Em Bailey's industrial oil and fat products. John Wiley & Sons Inc.: New York.

Menezes FAF, Rangel AB, Cordeiro TC, Vargas H, Silva EC. 2021. Investigation of phase transitions in vegetable oils through temperaturedependent optical measurements: supercooling efect. J. Therm. Anal. Calorim. 143, 27-33. https://doi.org/10.1007/s10973-019-09168-7

Moreira KS, Moura Junior LS, Monteiro RRC, Oliveira ALB, Valle CP, Freire TM, Fechine PBA, Souza MCM, Fernandez-Lorente G, Guisan JM, Santos JCS. 2020. Optimization of the Production of Enzymatic Biodiesel from Residual Babassu Oil (Orbignya sp.) via RSM. Catal. 10, 1-20. https://doi.org/10.3390/catal10040414

Mulalee S, Srisuwan P, Phisalaphong M. 2015. Influences of operating conditions on biocatalytic activity and reusability of Novozym 435 for esterification of free fatty acids with short-chainalcohols: A case study of palm fatty acid distillate. Chin. J. Chem. Eng. 23, 1851-1856. https://doi.org/10.1016/j.cjche.2015.08.016

Nguyen VTA, Le TD, Phan HN, Tran LB. 2017. Antibacterial Activity of Free Fatty Acids from Hydrolyzed Virgin Coconut Oil Using Lipase from Candida rugosa. J. Lipids 2017, 1-7. https://doi.org/10.1155/2017/7170162 PMid:29259829 PMCid:PMC5702975

Ortiz C, Ferreira ML, Barbosa O, Dos Santos JCS, Rodrigues R.C., Berenguer-Murcia, A., Briand, L.E., Fernandez-Lafuente, R. 2019. Novozym 435: the "perfect" lipase immobilized biocatalyst? Catal. Sci. Technol. 9, 2380-2420. https://doi.org/10.1039/C9CY00415G

Raspe DT, Silva C, Cardozo-Filho L. 2013. Effect of additives and process variables on enzymatic hydrolysis of macauba kernel oil (Acrocomia aculeata). Chem. Eng. J. 2013, 1-8. https://doi.org/10.1155/2013/438270

Rodrigues RC, Ayub MAZ. 2011. Effects of the combined use of Thermomyces lanuginosus and Rhizomucor miehei lipases for the transesterification and hydrolysis of soybean oil. Process Biochem 46, 682-688. https://doi.org/10.1016/j.procbio.2010.11.013

Rosa ACS, Stevanato N, Garcia VAS, Silva C. 2020. Simultaneous extraction of the oil from the kernel and pulp of macauba fruit using a green solvent. J. Food Process Pres. 44, 1-14. https://doi.org/10.1111/jfpp.14855

Rosset DV, Wancura JHC, Ugalde GA, Oliveira JV, Tres MV, Kuhn RC. Jahn SL. 2019. Enzyme-Catalyzed Production of FAME by Hydroesterification of Soybean Oil Using the Novel Soluble Lipase NS 40116. Biotechnol. Appl. Biochem. 188, 914-926. https://doi.org/10.1007/s12010-019-02966-7 PMid:30729422

Santos LDF, Coutinho JAP, Ventura SPM. 2015. From Water-in-Oil to Oil-in-Water Emulsions to Optimize the Production of Fatty Acids Using Ionic Liquids in Micellar Systems. Biotechnol. Prog. 31, 1473-1480. https://doi.org/10.1002/btpr.2156 PMid:26286754

Shin M, Seo J, Baek Y, Lee T, Jang M, Park C. 2020. Novel and Efficient Synthesis of Phenethyl Formate via Enzymatic Esterification of Formic Acid. Biomolecules 10, 1-15. https://doi.org/10.3390/biom10010070 PMid:31906270 PMCid:PMC7022603

Silva C, Colonelli TAS, Postaue N, Zempulski D, Trentini CP, Silva EA, Cardozo Filho L. 2021. Catalyst-free production of fatty acid ethyl esters (FAEE) from macauba pulp oil. Grasas Aceites 72 (1), e398. https://doi.org/10.3989/gya.0103201

Sousa JS, Cavalcanti-Oliveira EA, Arandab DAG, Freire DMG. 2010. Application of lipase from the physic nut (Jatropha curcas L.) to a new hybrid (enzyme/chemical) hydroesterification process for biodiesel production. J. Mol. Catal. B. Enzym. 65, 133-137. https://doi.org/10.1016/j.molcatb.2010.01.003

Tamagno S, Aznar-Moreno JA, Durrett TP, Prasad PVV, Rotundo JL, Ciampitti IA. 2020. Dynamics of oil and fatty acid accumulation during seed development in historical soybean varieties. Field Crops Res. 248, 1-10, 2020. https://doi.org/10.1016/j.fcr.2020.107719

Tavares F, Silva EAD, Pinzan F, Canevesi RS, Milinsk MC, Scheufele FB, Borba CE. 2018. Hydrolysis of crambe oil by enzymatic catalysis: An evaluation of the operational conditions. Biocat. Biotransf. 36, 1-14. https://doi.org/10.1080/10242422.2018.1430786

Teixeira DA, Motta CR, Ribeiro CMS, Castro AM. 2017. A rapid enzyme-catalyzed pretreatment of the acidic oil of macauba (Acrocomia aculeata) for chemoenzymatic biodiesel production. Process Biochem. 53, 188-193. https://doi.org/10.1016/j.procbio.2016.12.011

Trentini CP, Cuco RP, Cardozo-Filho L, Silva C. 2018. Extraction of macauba kernel oil using supercritical carbon dioxide and compressed propane. Can. J. Chem. Eng. 97, 785-792. https://doi.org/10.1002/cjce.23236

Vescovi V, Rojas MJ, Baraldo A, Botta DC, Santana FAM, Costa JP, Machado MS, Honda VK, Giordano RLC, Tardioli PW. 2016. LipaseCatalyzed Production of Biodiesel by Hydrolysis of Waste Cooking Oil Followed by Esterification of Free Fatty Acids. J. Am. Oil Chem. Soc. 93, 1615-1624. https://doi.org/10.1007/s11746-016-2901-y

Wancura, JHC, Rosset DV, Mazutti MA, Ugalde GA, Oliveira V, Tres MV, Jahn SL. 2019. Improving the soluble lipase-catalyzed biodiesel production through a two-step hydroesterification reaction system. Appl. Microbiol. Biotechnol. 103, 7805-7817. https://doi.org/10.1007/s00253-019-10075-y PMid:31414164

Wancura JHC, Fantinel AL, Ugalde GA, Donato FF, Oliveira JV, Tres MV, Jahn SL. (2021). Semi-continuous production of biodiesel on pilot scale via enzymatic hydroesterification of waste material: Process and economics considerations. J. Clean Prod. 285, 124838. https://doi.org/10.1016/j.jclepro.2020.124838

Wang WC, Turner TL, Stikeleather LF, Roberts WL. 2012. Exploration of process parameters for continuous hydrolysis of canola oil, camelina oil and algal oil. Chem. Eng. Process 57-58, 51-58. https://doi.org/10.1016/j.cep.2012.04.001

Zenevicz MCP, Jacques A, Furigo A, Oliveira V, Oliveira D. 2016. Enzymatic hydrolysis of soybean and waste cooking oils under ultrasound system. Ind. Crops Prod. 80, 235-241. https://doi.org/10.1016/j.indcrop.2015.11.031

Zhou GX, Chen GV, Yan BB. 2015. Two-step biocatalytic process using lipase and whole cell catalysts for biodiesel production from unrefined jatropha oil. Biotechnol. Lett. 37, 1959-1963. https://doi.org/10.1007/s10529-015-1883-4 PMid:26063623