Ключові слова
Як цитувати
Анотація
Стаття присвячена використанню сульфокатіонітів, що відрізняються за пористою структурою (макроретикулярний Purolite CT275 і гелевий КУ-2-8Чс), як твердих кислотних каталізаторів для синтезу перспективних біомаститльних компонентів шляхом розкриття оксиранових циклів жирних епоксидів водою (гідроліз), етанолом та і-пропанолом (алкоксилювання), і левуліновою та олеїновою кислотами (ацилювання). Епоксидовані етил- та і-пропіл олеати як субстрати для реакцій розкриття оксиранів було синтезовано на основі використаної кулінареної олії. Реакції проводили в реакторі періодичної дії протягом 3 годин за 100 °C з перемішуванні, молярне співвідношення епоксид : кислотні центри каталізатора становило 1 : 0.05. Співвідношення реагент : епоксид становило 10 : 1 (алкоксилювання, гідроліз) або 1.5 : 1 (ацилювання). Склад продуктів визначали методом ГХ, розраховували конверсію та селективність. Виявлено ряд бічних реакцій розкриття кільця, основними з яких є ізомеризація до кетону та димеризація. Загальним спостереженням було те, що пористий Purolite CT275 забезпечує більш високу конверсію, але сприяє побічним процесам. Непористий CU-2-8-CHs забезпечував помітно вищу селективність (до 90 % для гідрокси етерів при етоксилюванні), але з у багато разів повільнішим перетворенням, особливо у випадку алкоксилювання вторинним спиртом. При гідролізі просочені водою катіоніти не забезпечили жодного перетворення, тоді як введення епоксиду спочатку на каталізаторі робило перетворення можливим. Ацилювання значною мірою протікало без окремого каталізатора і супроводжувалося димеризацією, а ізомеризації не спостерігалося. Катіоніт гелевого типу забезпечував лише зникомо мале зростання конверсії та селективності. Пористий катіоніт підвищував конверсію, але головним чином за рахунок інтенсифікації побічних реакцій. Циклогексан як розчинник дещо сприяв селективному ацилюванню без каталізатора, але зі значним зниженням конверсії. Purolite CT275 у середовищі етиллевулінату сприяв розкриттю епоксиду кето-групою левулінової кислоти з утворенням продукту типу кеталю.
Посилання
Moser B.R., Cermak S.C., Doll K.M., Kenar J.A., Sharma B.K. A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications. J. Am. Oil Chem. Soc., 2022, 99(1), 801-842.
https://doi.org/10.1002/aocs.12623
Orjuela A., Clark J. Green Chemicals from Used Cooking Oils: Trends, Challenges and Opportunities. Curr. Opin. Green Sustainable Chem., 2020, 26, 100369.
https://doi.org/10.1016/j.cogsc.2020.100369
Benaniba M.T., Belhaneche-Bensemra N., Gelbard G. Stabilization of PVC by epoxidized sunflower oil in the presence of zinc and calcium stearates. Polym. Degrad. Stab., 2003, 82, 245-249..
https://doi.org/10.1016/S0141-3910(03)00178-2
Hassan A.A., Abbas A., Rasheed T., Bilal M., Iqbal H.M.N., Wang S. Development, influencing parameters and interactions of bioplasticizers: an environmentally friendlier alternative to petro industry-based sources. Sci. Total Environ., 2019, 682, 394-404.
https://doi.org/10.1016/j.scitotenv.2019.05.140
Milchert E., Malarczyk K., Klos M. Technological aspects of chemoenzymatic epoxidation of fatty acids, fatty acid esters and vegetable oils: a review. Molecules, 2015, 20(12), 21481-21493.
https://doi.org/10.3390/molecules201219778
Milchert E., Malarczyk-Matusiak K., Musik M. Technological aspects of vegetable oils epoxidation in the presence of ion exchange resins: a review. Pol. J. Chem. Technol., 2016, 18, 128-133.
https://doi.org/10.1515/pjct-2016-0059
Nameer S., Deltin T., Sundell P.K., Johansson M. Bio-based multifunctional fatty acid methyl esters as reactive diluents in coil coatings. Prog. Org. Coat., 2019, 136, 105277.
https://doi.org/10.1016/j.porgcoat.2019.105277
Radojcic D., Hong J., Petrovic Z.S. From natural oils to epoxy resins: a new paradigm in renewable performance materials. J. Polym. Environ., 2022, 30, 765-775.
https://doi.org/10.1007/s10924-021-02228-w
Radojcic D., Ionescue M., Petrovic Z.S. Room temperature cationic polymerization of epoxy methyl oleate with B(C6F5)3. J. Polym. Environ., 2021, 29, 2072-2079.
https://doi.org/10.1007/s10924-020-01984-5
Liu Z., Erhan S.Z., Calvert P.D. Solid freeform fabrication of epoxidized soybean oil/epoxy composites with di-, tri-, and polyethylene amine curing agents. J. Appl. Polym. Sci., 2007, 93, 356-363.
https://doi.org/10.1002/app.20412
Samper M.D., Fombuena V., Boronat T., Garcia-Sanoguera D., Balart R. Thermal and mechanical characterization of epoxy resins (ELO and ESO) cured with anhydrides. J. Am. Oil Chem. Soc., 2012, 89, 1521-1528.
https://doi.org/10.1007/s11746-012-2041-y
Llevot A. Sustainable synthetic approaches for the preparation of plant oil-based thermosets. J. Am. Oil Chem. Soc., 2017, 94, 169-186.
https://doi.org/10.1007/s11746-016-2932-4
Ribau M., Nogueira R., Miguel L. Quantitative assessment of the valorisation of used cooking oils in 23 countries. Waste Manage., 2018, 78, 611-620.
https://doi.org/10.1016/j.wasman.2018.06.039
Hwang H.K., Erhan S.Z. Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point. J. Am. Oil Chem. Soc., 2001, 78, 1179-1184.
https://doi.org/10.1007/s11745-001-0410-0
Hwang H.K., Adhvaryu A., Erhan S.Z. Preparation and properties of lubricant basestocks from epoxidized soybean oil and 2-ethylhexanol. J. Am. Oil Chem. Soc., 2003, 80, 811-815.
https://doi.org/10.1007/s11746-003-0777-y
Hwang H.K., Erhan S.Z. Synthetic lubricant basestocks from epoxidized soybean oil and Guerbet alcohols. Ind. Crops Prod., 2006, 23, 311-317.
https://doi.org/10.1016/j.indcrop.2005.09.002
Borugadda V.B., Goud V.V. Hydroxylation and hexanoylation of epoxidized waste cooking oil and epoxidized waste cooking oil methyl esters: process optimization and physico-chemical characterization. Ind. Crops Prod., 2019, 133,151-159.
https://doi.org/10.1016/j.indcrop.2019.01.069
Moser B.R., Erhan S.Z. Synthesis and evaluation of a series of α-hydroxy ethers derived from isopropyl oleate. J. Am. Oil Chem. Soc., 2006, 83, 959-963.
https://doi.org/10.1007/s11746-006-5053-7
Moser B.R., Erhan S.Z. Preparation and evaluation of a series of α-hydroxy ethers from 9,10-epoxystearates. Eur. J. Lipid Sci. Technol., 2007, 109, 206-213.
https://doi.org/10.1002/ejlt.200600257
Kulkarni R.D., Deshpande P.S., Mahajan S.U., Mahulikar P.P. Epoxidation of mustard oil and ring opening with 2-ethylhexanol for biolubricants with enhanced thermo-oxidative and cold flow characteristics. Ind. Crops Prod., 2013, 49, 586-592.
https://doi.org/10.1016/j.indcrop.2013.06.006
Harry-O'kuru R.E., Holser R.A., Abbott T.P., Weisleder D. Synthesis and characteristics of polyhydroxy triglycerides from milkweed oil. Ind. Crops Prod., 2002, 15, 51-58.
https://doi.org/10.1016/S0926-6690(01)00095-4
Kollbe A. B., Kraft S., Wang D., Sun S. Thermally stable, transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil. Biomacromolecules, 2011, 12, 1839-1843.
https://doi.org/10.1021/bm200188u
Li Y., Sun X.S. Camelina oil derivatives and adhesion properties. Ind. Crops Prod., 2015, 73, 73-80.
https://doi.org/10.1016/j.indcrop.2015.04.015
Pillai P.K.S., Li S., Bouzidi L., Narine S.S. Solvent-free synthesis of polyols from 1-butene metathesized palm oil for use in polyurethane foams. J. Appl. Polym. Sci., 2016, 133, 43509.
https://doi.org/10.1002/app.43509
Arbenz A., Perrin R., Averous L. Elaboration and properties of innovative biobased PUIR foams from microalgae. J. Polym. Environ., 2018, 26, 254-262.
https://doi.org/10.1007/s10924-017-0948-y
Campanella A., Bonnaillie L.M., Wool R.P. Polyurethane foams from soyoil-based polyols. J. Appl. Polym. Sci., 2009, 112, 2567-2578.
https://doi.org/10.1002/app.29898
Campanella A., Rustoy E., Baldessari A., Baltanas M.A. Lubricants from chemically modified vegetable oils. Bioresour. Technol., 2010, 101, 245-254.
https://doi.org/10.1016/j.biortech.2009.08.035
Gobin M., Loulergue P., Audic J.L., Lemiegre L. Synthesis and characterization of bio-based polyester materials from vegetable oil and short to long chain dicarboxylic acids. Ind. Crops Prod., 2015, 70, 213-220.
https://doi.org/10.1016/j.indcrop.2015.03.041
Pindit K., Thanapimmetha A., Saisriyoot M., Srinopakun P. Biolubricant basestocks synthesis using 5-step reaction from jatropha oil, soybean oil, and palm fatty acid distillate. Ind. Crops Prod., 2021, 166, 113484.
https://doi.org/10.1016/j.indcrop.2021.113484
Salimon J., Abdullah B.M., Salih N. Optimization of the oxirane ring opening reaction in biolubricant base oil production. Arab. J. Chem., 2016, 9, 1053-1058.
https://doi.org/10.1016/j.arabjc.2011.11.002
Hazmi A.S.A., Aung M.M., Abdullah L.C., Salleh M.Z., Mahmood M.H. Producing Jatropha oil-based polyol via epoxidation and ring opening. Ind. Crops Prod., 2013, 50, 563-567.
https://doi.org/10.1016/j.indcrop.2013.08.003
Junming X., Jianchun J., Jing L. Preparation of polyester polyols from unsaturated fatty acid. J. Appl. Polym. Sci., 2012, 126, 1377-1784.
https://doi.org/10.1002/app.36740
Azzena U., Carraro M., Pisano L., Pintus E., Pintus S., Polese R. et al. Size selectivity in the hydroxylation of esters of unsaturated fatty acids. Eur. J. Lipid Sci. Technol., 2022, 124, 2100234.
https://doi.org/10.1002/ejlt.202100234
Rios L., Echeverri D., Cardeno F. Hydroxylation of vegetable oils using acidic resins as catalysts. Ind. Crops Prod., 2013, 43, 183-187.
https://doi.org/10.1016/j.indcrop.2012.07.035
Borugadda V.B., Somidi A.K.R., Dalai A.K. Chemical/structural modification of canola oil and canola biodiesel: kinetic studies and biodegradability of the alkoxides. Lubricants, 2017. 5(2), 11.
https://doi.org/10.3390/lubricants5020011
Coman A.E., Peyrton J., Hubca G., Sarbu A., Gabor A.R., Nicolae C.A. et al. Synthesis and characterization of renewable polyurethane foams using different biobased polyols from olive oil. Eur. Polym. J., 2021, 149, 110363.
https://doi.org/10.1016/j.eurpolymj.2021.110363
Lathi P.S., Mattiasson B. Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil. Appl. Catal. B, 2007, 69, 207-212.
https://doi.org/10.1016/j.apcatb.2006.06.016
Madankar C.S., Dalai A.K., Naik S.N. Green synthesis of biolubricant base stock from canola oil. Ind. Crops Prod., 2013, 44, 139-144.
https://doi.org/10.1016/j.indcrop.2012.11.012
Marques J.P.C., Rios I.C., Parente E.J.S.Jr., Quintella S.A., Luna F.M.T., Cavalcante C.L.Jr. Synthesis and characterization of potential bio-based lubricant basestocks via epoxidation process. J. Am. Oil Chem. Soc., 2019, 97, 437-446.
https://doi.org/10.1002/aocs.12317
Omonov T.S., Kharraz E., Curtis J.M. Camelina (Camelina sativa) oil polyols as an alternative to castor oil. Ind. Crops Prod., 2017, 107, 378-385.
https://doi.org/10.1016/j.indcrop.2017.05.041
Peyrton J., Chambaretaud C., Sarbu A., Averous L. Biobased polyurethane foams based on new polyol architectures from microalgae oil. ACS Sustain. Chem. Eng., 2020, 8, 12187-12196.
https://doi.org/10.1021/acssuschemeng.0c03758
Peyrton J., Chambaretaud C., Averous L. New insight on the study of the kinetic of biobased polyurethanes synthesis based on oleochemistry. Molecules, 2019, 24, 4332.
https://doi.org/10.3390/molecules24234332
Schuster H., Rios L.A., Weckes P.P., Hoelderich W.F. Heterogeneous catalysts for the production of new lubricants with unique properties. Appl. Catal. A Gen., 2008, 348(2), 266-270.
https://doi.org/10.1016/j.apcata.2008.07.004
Osazuwa U.I., Abidin S.Z. The Functionality of ion exchange resins for esterification, transesterification and hydrogenation reactions. СhemSelect., 2022, 5, 7658-7670.
https://doi.org/10.1002/slct.202001381
Khodadadi M.R., Malpartida I., Tsang C-W., Lin C.S.K., Len C. Recent advances on the catalytic conversion of waste cooking oil. Molecular Catalysis, 2020, 494, 111128.
https://doi.org/10.1016/j.mcat.2020.111128
Orege R., Oderinde O., Kifle G.A., Ibikunle A.A., Raheem S.A., Ejeromedoghene O. et al. Recent advances in heterogeneous catalysis for green biodiesel production by transesterification. Energy Convers. Manage., 2022, 258, 115406.
https://doi.org/10.1016/j.enconman.2022.115406
Tao J., Pan Y., Zhou H., Tang Y., Ren G., Yu Z., Li J., Zhang R., Li X., Qiao Y., Lu X., Xiong J. Catalytic systems for 5-hydroxymethylfurfural preparation from different biomass feedstocks: a review. Catalysts, 2024, 14, 30-43.
https://doi.org/10.3390/catal14010030
Wang Y., Yuan X., Liu J., Jia X. Recent advances in zeolites-catalyzed biomass conversion to hydroxymethylfurfural: the role of porosity and acidity. ChemPlusChem, 2024, 89, e202300399.
https://doi.org/10.1002/cplu.202300399
Gómez‐de‐Miranda‐Jiménez‐de‐Aberasturi O., Perez‐Arce J. Efficient epoxidation of vegetable oils through the employment of acidic ion exchange resins. Can. J. Chem. Eng., 2019, 97(6), 1785-1791.
https://doi.org/10.1002/cjce.23429
Turco R., Vitiello R., Russo V., Tesser R., Santacesaria E., Di Serio M. Selective epoxidation of soybean oil with performic acid catalyzed by acidic ionic exchange resins. Green Process. Synth., 2013, 2(5), 427-434.
https://doi.org/10.1515/gps-2013-0045
Bouzidi L., Li S., De Biase S., Rizvi S.Q., Dawson P., Narine S.S. Lubricating and waxy esters II: synthesis, crystallization, and melt behavior of branched monoesters. Ind. Eng. Chem. Res., 2012, 51, 14892-14902.
https://doi.org/10.1021/ie3016472
Caillol S., Desroches M., Boutevin G., Loubat C., Auvergne R., Boutevin B. Synthesis of new polyester polyols from epoxidized vegetable oils and biobased acids. Eur. J. Lipid Sci. Technol., 2012, 114, 1447-1459.
https://doi.org/10.1002/ejlt.201200199
Moser B.R., Sharma B.K., Doll K.M., Erhan S.Z. Diesters from oleic acid: synthesis, low temperature properties, and oxidation stability. J. Am. Oil Chem. Soc., 2007, 84, 675-680.
https://doi.org/10.1007/s11746-007-1083-z
Dehghan P., Noroozi M., Sadeghi G.M.M., Abrisham M., Amirkiai A. Panahi-Sarmad M. Synthesis and design of polyurethane and its nanocomposites derived from canola-castor oil: mechanical, thermal and shape memory properties. J. Polym. Sci., 2020, 58, 3082-3094.
https://doi.org/10.1002/pol.20200474
Dai Z., Jiang P., Lou W., Zhang P., Bao Y., Gao X. et al. Preparation of degradable vegetable oil-based waterborne polyurethane with tunable mechanical and thermal properties. Eur. Polym. J., 2020, 139, 109994.
https://doi.org/10.1016/j.eurpolymj.2020.109994
Kollbe A.B., Kraft S., Sun S.X. Solvent-free acid-catalyzed ringopening of epoxidized oleochemicals using stearates/stearic acid and its applications. J. Agric. Food Chem., 2012, 60, 2179-2189.
https://doi.org/10.1021/jf204275q
Konovalov S., Zubenko S., Patrylak L., Yakovenko A., Povazhnyi V., Burlachenko K. Chemmotological aspects of sustainable development of transport. - Sustainable Aviation. Springer, Cham., 2022. - P. 49-80.
https://doi.org/10.1007/978-3-031-06577-4_4
Konovalov S., Patrylak L., Zubenko S., Okhrimenko M., Yakovenko A., Levterov A. Alkali synthesis of fatty acid butyl and ethyl esters and comparative bench motor testing of blended fuels on their basis. Chem. Chem. Technol., 2021, 15(1), 105-117.
Monono E.M., Bahr J.A., Pryor S.W., Webster D.C., Wiesenborn D.P. Optimizing process parameters of epoxidized sucrose soyate synthesis for industrial scale production. Org. Process Res. Dev., 2015, 19(11), 1683-1692.
https://doi.org/10.1021/acs.oprd.5b00251
Zubenko S.O. The simple method of vegetable oils and oleochemical products acid value determination. Catal. Petrochemistry, 2021, 31, 69-74.
https://doi.org/10.15407/kataliz2021.31.069
International Technical Standards GOST 20298-74. [in Russian].
https://www.purolite.com/product-pdf/CT275.pdf.
Davitadze D.Z., Konovalov S.V., Zubenko S.O., Pertko O.P., Pyliavskyi V.S. Promising approaches to chemical modification of acylglycerol biomass using sulfocationites as solid acid catalysts. Bioactive compounds, new substances and materials / Proceedings of the XXVIII Scientific Conference on Bioorganic Chemistry and Petrochemistry. Kyiv: Interservis, 2023. - P. 240-245.
Davitadze D., Konovalov S., Zubenko S., Pertko O., Pyliavskyi V., Yakovenko A. Products of chemical modification of high oleic waste sunflower oil as fuel additives. Book of Abstracts of IХ International Scientific-Technical Conference "Theory and practice of rational use of traditional and alternative fuels and lubricants" (PROBLEMS OF CHEMMOTOLOGY), Kyiv-Warsaw, July 03-07, 2023, P. 120-121.