Tenebrio molitor Larvae-Based Magnetic Polyurea Employed as Crude Oil Spill Removal Tool
Abstract
:1. Introduction
2. Experimental
2.1. Materials
2.2. Methods
2.2.1. Polyurea Synthesis
2.2.2. Magnetic Force Test
2.2.3. Crude Oil Magnetic Removal
2.2.4. X-ray Diffraction (XRD)
2.2.5. Fourier Transform Infrared Spectroscopy Using Attenuated Total Reflectance (FTIR-ATR)
2.2.6. Low-Field Nuclear Magnetic Resonance (LF-NMR 1H)
2.2.7. Thermogravimetric Analysis (TGA) and Scanning Differential Calorimetry (DSC)
3. Results and Discussion
3.1. Crude Oil Magnetic Removal
3.2. X-ray Diffraction (XRD)
3.3. Fourier Transform Infrared Spectroscopy Using Attenuated Total Reflectance (FTIR-ATR)
3.4. Low-Field Nuclear Magnetic Resonance (LF-NMR 1H)
3.5. Thermogravimetric Analysis (TGA)
3.6. Differential Scanning Calorimetry (DSC)
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
- Jenck, J.F.; Agterberg, F.; Droescher, M.J. Products and processes for a sustainable chemical industry: A review of achievements and prospects. Green Chem. 2004, 6, 544–556. [Google Scholar] [CrossRef]
- Raquez, J.M.; Deléglise, M.; Lacrampe, M.F.; Krawczak, P. Thermosetting (bio)materials derived from renewable resources: A critical review. Prog. Polym. Sci. 2010, 35, 487–509. [Google Scholar] [CrossRef]
- Kümmerer, K. Sustainable from the very beginning: Rational design of molecules by life cycle engineering as an important approach for green pharmacy and green chemistry. Green Chem. 2007, 9, 899–907. [Google Scholar] [CrossRef]
- Borges, G.R.; Aboelkheir, M.G.; de Souza Junior, F.G.; Waldhelm, K.C.; Kuster, R.M. Poly (butylene succinate) and derivative copolymer filled with Dendranthema grandiflora biolarvicide extract. Environ. Sci. Pollut. Res. 2020, 27, 23575–23585. [Google Scholar] [CrossRef]
- Rodrigues André, F.; Galal Aboelkheir, M. Sustainable approach of applying previous treatment of tire wastes as raw material in cement composites: Review. Mater. Today Proc. 2022, 58, 1557–1565. [Google Scholar] [CrossRef]
- Adekunle, K.F. A Review of Vegetable Oil-Based Polymers: Synthesis and Applications. Open J. Polym. Chem. 2015, 5, 34–40. [Google Scholar] [CrossRef] [Green Version]
- Biermann, U.; Bornscheuer, U.; Meier, M.A.R.; Metzger, J.O.; Schäfer, H.J. Oils and Fats as Renewable Raw Materials in Chemistry. Angew. Chem. Int. Ed. 2011, 50, 3854–3871. [Google Scholar] [CrossRef]
- Da Costa, V.C.; Aboelkheir, M.G.; Pal, K.; Filho RD, T.; Gomes, F. Chapter 15—Smart polymer systems as concrete self-healing agents. In Nanofabrication for Smart Nanosensor Applications; Micro and Nano Technologies; Pal, K., Gomes, F., Eds.; Elsevier: Amsterdam, The Netherlands, 2020; pp. 399–413. [Google Scholar]
- Zhang, X.; Burgar, I.; Do, M.D.; Lourbakos, E. Intermolecular interactions and phase structures of plasticized wheat proteins materials. Biomacromolecules 2005, 6, 1661–1671. [Google Scholar] [CrossRef]
- Belgacem, M.N.; Gandini, A. Monomers, Polymers and Composites from Renewable Resources; Elsevier Ltd.: Amsterdam, The Netherlands, 2008. [Google Scholar]
- Aboelkheir, M.G.; Visconte, L.Y.; Oliveira, G.E.; Toledo Filho, R.D.; Souza, F.G. The biodegradative effect of Tenebrio molitor Linnaeus larvae on vulcanized SBR and tire crumb. Sci. Total Environ. 2019, 649, 1075–1082. [Google Scholar] [CrossRef]
- Aboelkheir, M.G.; Bedor, P.B.; Leite, S.G.; Pal, K.; Toledo Filho, R.D.; Gomes de Souza, F. Biodegradation of Vulcanized SBR: A Comparison between Bacillus subtilis, Pseudomonas aeruginosa and Streptomyces sp. Sci. Rep. 2019, 9, 19304. [Google Scholar] [CrossRef]
- Eom, T.; Jeon, J.; Lee, S.; Woo, K.; Heo, J.E.; Martin, D.C.; Wie, J.J.; Shim, B.S. Naturally Derived Melanin Nanoparticle Composites with High Electrical Conductivity and Biodegradability. Part. Part. Syst. Charact. 2019, 36, 1900166. [Google Scholar] [CrossRef]
- Kaewpetch, B.; Prasongsuk, S.; Poompradub, S. Devulcanization of natural rubber vulcanizates by Bacillus cereus TISTR 2651. Express Polym. Lett. 2019, 13, 877–888. [Google Scholar] [CrossRef]
- Lazorenko, G.; Kasprzhitskii, A.; Mischinenko, V. Rubberized geopolymer composites: Effect of filler surface treatment. J. Environ. Chem. Eng. 2021, 9, 105601. [Google Scholar] [CrossRef]
- Yang, S.-S.; Ding, M.-Q.; He, L.; Zhang, C.-H.; Li, Q.-X.; Xing, D.-F.; Cao, G.-L.; Zhao, L.; Ding, J.; Ren, N.-Q.; et al. Biodegradation of polypropylene by yellow mealworms (Tenebrio molitor) and superworms (Zophobas atratus) via gut-microbe-dependent depolymerization. Sci. Total Environ. 2021, 756, 144087. [Google Scholar] [CrossRef]
- Yang, Y.; Wang, J.; Xia, M. Biodegradation and mineralization of polystyrene by plastic-eating superworms Zophobas atratus. Sci. Total Environ. 2020, 708, 135233. [Google Scholar] [CrossRef]
- Zhang, F.; Zhao, Y.; Wang, D.; Yan, M.; Zhang, J.; Zhang, P.; Ding, T.; Chen, L.; Chen, C. Current technologies for plastic waste treatment: A review. J. Clean. Prod. 2021, 282, 124523. [Google Scholar] [CrossRef]
- Zielińska, E.; Zieliński, D.; Jakubczyk, A.; Karaś, M.; Pankiewicz, U.; Flasz, B.; Dziewięcka, M.; Lewicki, S. The impact of polystyrene consumption by edible insects Tenebrio molitor and Zophobas morio on their nutritional value, cytotoxicity, and oxidative stress parameters. Food Chem. 2021, 345, 128846. [Google Scholar] [CrossRef]
- Gacitua, W.; Ballerini, A.; Zhang, J. Polymer Nanocomposites: Synthetic and Natural Fillers—A Review. Maderas Cienc. Tecnol. 2005, 7, 159–178. [Google Scholar] [CrossRef] [Green Version]
- Ghanbarzadeh, B.; Oleyaei, S.A.; Almasi, H. Nanostructured Materials Utilized in Biopolymer-Based Plastics for Food Packaging Applications. Crit. Rev. Food Sci. Nutr. 2015, 55, 1699–1723. [Google Scholar] [CrossRef]
- Aboelkheir, M.; Siqueira, C.Y.S.; Souza, F.G.; Filho, R.D.T. Influence of Styrene-Butadiene Co-Polymer on the Hydration Kinetics of SBR-Modified Well Cement Slurries. Macromol. Symp. 2018, 380, 1800131. [Google Scholar] [CrossRef]
- Kalia, S.; Kango, S.; Kumar, A.; Haldorai, Y.; Kumari, B.; Kumar, R. Magnetic polymer nanocomposites for environmental and biomedical applications. Colloid Polym. Sci. 2014, 292, 2025–2052. [Google Scholar] [CrossRef]
- Thanikaivelan, P.; Narayanan, N.T.; Pradhan, B.K.; Ajayan, P.M. Collagen based magnetic nanocomposites for oil removal applications. Sci. Rep. 2012, 2, 230. [Google Scholar] [CrossRef] [Green Version]
- Veloso de Carvalho, F.; Pal, K.; Gomes de Souza, F., Jr.; Dias Toledo Filho, R.; Moraes de Almeida, T.; Daher Pereira, E.; Thode Filho, S.; Galal Aboelkheir, M.; Corrêa Costa, V.; Ricardo Barbosa de Lima, N.; et al. Polyaniline and magnetite on curaua fibers for molecular interface improvement with a cement matrix. J. Mol. Struct. 2021, 1233, 130101. [Google Scholar] [CrossRef]
- Shirinova, H.; Di Palma, L.; Sarasini, F.; Tirillò, J.; Ramazanov, M.A.; Hajiyeva, F.; Sannino, D.; Polichetti, M.; Galluzzi, A. Synthesis and characterization of magnetic nanocomposites for environmental remediation. Chem. Eng. Trans. 2016, 47, 103–108. [Google Scholar]
- Meiorin, C.; Muraca, D.; Pirota, K.R.; Aranguren, M.I.; Mosiewicki, M.A. Nanocomposites with superparamagnetic behavior based on a vegetable oil and magnetite nanoparticles. Eur. Polym. J. 2014, 53, 90–99. [Google Scholar] [CrossRef]
- Souza, F.G.; Ferreira, A.C.; Varela, A.; Oliveira, G.E.; Machado, F.; Pereira, E.D.; Fernandes, E.; Pinto, J.C.; Nele, M. Methodology for determination of magnetic force of polymeric nanocomposites. Polym. Test. 2013, 32, 1466–1471. [Google Scholar] [CrossRef] [Green Version]
- Lopes, M.C.; Souza, F.G., Jr.; Oliveira, G.E. Espumados magnetizáveis úteis em processos de recuperação ambiental. Polímeros 2010, 20, 359–365. [Google Scholar] [CrossRef] [Green Version]
- Gomes de Souza, F., Jr.; Marins, J.A.; Rodrigues, C.H.M.; Pinto, J.C. A Magnetic Composite for Cleaning of Oil Spills on Water. Macromol. Mater. Eng. 2010, 295, 942–948. [Google Scholar] [CrossRef]
- Ferreira, L.P.; Moreira, A.N.; Delazare, T.; Oliveira Geiza, E.; Souza, F.G., Jr. Petroleum Absorbers Based on CNSL, Furfural and Lignin—The Effect of the Chemical Similarity on the Interactions among Petroleum and Bioresins. Macromol. Symp. 2012, 319, 210–221. [Google Scholar] [CrossRef]
- Varela, A.; Oliveira, G.; Souza, F.G., Jr.; Rodrigues, C.H.M.; Costa, M.A.S. New petroleum absorbers based on cardanol-furfuraldehyde magnetic nanocomposites. Polym. Eng. Sci. 2013, 53, 44–51. [Google Scholar] [CrossRef]
- Grance, E.G.O.; Souza, F.G.; Varela, A.; Pereira, E.D.; Oliveira, G.E.; Rodrigues, C.H.M. New petroleum absorbers based on lignin-CNSL-formol magnetic nanocomposites. J. Appl. Polym. Sci. 2012, 126, E305–E312. [Google Scholar] [CrossRef]
- Elias, E.; Costa, R.; Marques, F.; Oliveira, G.; Guo, Q.; Thomas, S.; Souza, F.G., Jr. Oil-spill cleanup: The influence of acetylated curaua fibers on the oil-removal capability of magnetic composites. J. Appl. Polym. Sci. 2015, 132, 41732–41740. [Google Scholar] [CrossRef]
- Marques, F.D.; Souza, F.G., Jr.; Oliveira, G.E. Oil sorbers based on renewable sources and coffee grounds. J. Appl. Polym. Sci. 2016, 133, 43127–43134. [Google Scholar] [CrossRef]
- Da Costa, R.M.D.; Hungerbühler, G.; Saraiva, T.; De Jong, G.; Moraes, R.S.; Furtado, E.G.; Silva, F.M.; de Oliveira, G.E.; Ferreira, L.S.; Souza, F.G., Jr. Green polyurethane synthesis by emulsion technique: A magnetic composite for oil spill removal. Polímeros 2017, 27, 273–279. [Google Scholar] [CrossRef] [Green Version]
- Silva, J.C.; Oliveira, G.E.; Toledo Filho, R.D.; Souza, F.G., Jr. Oil Spill Clean-Up Tool Based on Castor Oil and Coffee Grounds Magnetic Resins. Macromol. Symp. 2018, 380, 1800095. [Google Scholar] [CrossRef]
- Lopes, M.C.; Marques, F.; Souza, F.G., Jr.; Oliveira, G.E. Experimental Design Optimization of Castor Oil, Phthalic Anhydride, and Glycerin Magnetic Nanocomposites Useful as Oil Spill Cleanup Tool. Macromol. Symp. 2018, 380, 1800085. [Google Scholar] [CrossRef]
- Marinho, V.; Lima, N.; Neves, M.A.; Souza, F., Jr. Petroleum Sorbers Based on Renewable Alkyd Resin and Lignin. Macromol. Symp. 2018, 380, 1800116. [Google Scholar] [CrossRef]
- Caetano, R.M.J.; Bedor, P.B.A.; de Jesus, E.F.O.; Leite, S.G.F.; Souza, F.G., Jr. Oil Biodegradation Systems Based on γ Irradiated Poly (Butylene Succinate). Macromol. Symp. 2018, 380, 1800123. [Google Scholar] [CrossRef]
- Figueiredo, A.S.; Icart, L.P.; Marques, F.D.; Fernandes, E.R.; Ferreira, L.P.; Oliveira, G.E.; Souza, F.G. Extrinsically magnetic poly(butylene succinate): An up-and-coming petroleum cleanup tool. Sci. Total Environ. 2019, 647, 88–98. [Google Scholar] [CrossRef]
- Da Silveira Maranhão, F.; Pereira de Oliveira, C.; Filho, S.T.; Das, D.B.; de Souza, F.G., Jr. Synthesis and Characterization of Modified Magnetic Nanoparticles for Removal of Dispersed Oil in Water. Braz. J. Exp. Des. Data Anal. Inferent. Stat. 2021, 1, 148–156. [Google Scholar] [CrossRef]
- Da Silveira Maranhão, F.; Gomes, F.; Thode, S.; Das, D.B.; Pereira, E.; Lima, N.; Carvalho, F.; Aboelkheir, M.; Costa, V.; Pal, K. Oil Spill Sorber Based on Extrinsically Magnetizable Porous Geopolymer. Materials 2021, 14, 5641. [Google Scholar] [CrossRef]
- Scherrer, P. Bestimmung der inneren Struktur und der Größe von Kolloidteilchen mittels Röntgenstrahlen. In Kolloidchemie Ein Lehrbuch; Chemische Technologie in Einzeldarstellungen; Zsigmondy, R., Ed.; Springer: Berlin/Heidelberg, Germany, 1912; pp. 387–409. [Google Scholar]
- Balan, V.; Mihai, C.-T.; Cojocaru, F.-D.; Uritu, C.-M.; Dodi, G.; Botezat, D.; Gardikiotis, I. Vibrational Spectroscopy Fingerprinting in Medicine: From Molecular to Clinical Practice. Materials 2019, 12, 2884. [Google Scholar] [CrossRef] [Green Version]
- Bordbar, A.K.; Rastegari, A.A.; Amiri, R.; Ranjbakhsh, E.; Abbasi, M.; Khosropour, A.R. Characterization of Modified Magnetite Nanoparticles for Albumin Immobilization. Biotechnol. Res. Int. 2014, 2014, e705068. [Google Scholar] [CrossRef] [Green Version]
- Da Costa, R.C.; Souza, F.G., Jr. Preparo de nanocompósitos de maghemita e polianilina assistido por ultrassom. Polímeros 2014, 24, 243–249. [Google Scholar] [CrossRef]
- Członka, S.; Bertino, M.F.; Kośny, J.; Strąkowska, A.; Masłowski, M.; Strzelec, K. Linseed oil as a natural modifier of rigid polyurethane foams. Ind. Crops Prod. 2018, 115, 40–51. [Google Scholar] [CrossRef]
- Kimura-Suda, H.; Takahata, M.; Ito, T.; Shimizu, T.; Kanazawa, K.; Ota, M.; Iwasaki, N. Quick and easy sample preparation without resin embedding for the bone quality assessment of fresh calcified bone using fourier transform infrared imaging. PLoS ONE 2018, 13, e0189650. [Google Scholar] [CrossRef] [Green Version]
- Kumar Das, A.; Marwal, A.; Verma, R. Bio-Reductive Synthesis and Characterization of Plant Protein Coated Magnetite Nanoparticles. Nano Hybrids 2014, 7, 69–86. [Google Scholar] [CrossRef] [Green Version]
- Ma, M.; Zhang, Y.; Yu, W.; Shen, H.; Zhang, H.; Gu, N. Preparation and characterization of magnetite nanoparticles coated by amino silane. Colloids Surf. A Physicochem. Eng. Asp. 2003, 212, 219–226. [Google Scholar] [CrossRef]
- Resende, D.K.; Dornelas, C.B.; Tavares, M.I.; Gomes, A.S.; Moreira, L.A.; Cabral, L.M.; Simeoni, L.A. Preparação de argila modificada com cloreto de cetilpiridíneo e avaliação da interação desta com o PVC. Polímeros 2010, 20, 231–235. [Google Scholar] [CrossRef] [Green Version]
- Vieira, I.R.S.; Costa, L.D.F.D.O.; Miranda, G.D.S.; Nardecchia, S.; Monteiro, M.S.D.S.D.B.; Ricci-Júnior, E.; Delpech, M.C. Waterborne Poly(urethane-urea)s Nanocomposites Reinforced with Clay, Reduced Graphene Oxide and Respective Hybrids: Synthesis, Stability and Structural Characterization. J. Polym. Environ. 2020, 28, 74–90. [Google Scholar] [CrossRef]
- Oliveira, V.C.D.S.P.D.; Tavares, M.I.B.; Silva, E.M.B.D.; Lima, B.N.B.D.; Cucinelli Neto, R.P. Uso da rmn de baixa resolução na avaliação da dinâmica molecular do Origanum vulgare. Quím. Nova 2015, 38, 351–355. [Google Scholar]
- Zheng, S.; Li, T.; Li, Y.; Shi, Q.; Wu, F. Novel 1H NMR relaxometry methods to study the proton distribution and water migration properties of tobacco. Anal. Methods 2017, 9, 1741–1747. [Google Scholar] [CrossRef]
- Awwad, A.M.; Salem, N.M. A Green and Facile Approach for Synthesis of Magnetite Nanoparticles. Nanosci. Nanotechnol. 2013, 2, 208–213. [Google Scholar] [CrossRef] [Green Version]
- Godovski, D.Y. Electron behavior and magnetic properties of polymer nanocomposites. Adv. Polym. Sci. 1995, 119, 78–122. [Google Scholar]
- Barrera, G.; Sciancalepore, C.; Messori, M.; Allia, P.; Tiberto, P.; Bondioli, F. Magnetite-epoxy nanocomposites obtained by the reactive suspension method: Microstructural, thermo-mechanical and magnetic properties. Eur. Polym. J. 2017, 94, 354–365. [Google Scholar] [CrossRef]
- Judeinstein, P.; Sanchez, C. Hybrid organic-inorganic materials: A land of multidisciplinarity. J. Mater. Chem. 1996, 6, 511–525. [Google Scholar] [CrossRef]
- Marín, T.; Montoya, P.; Arnache, O.; Pinal, R.; Calderón, J. Development of magnetite nanoparticles/gelatin composite films for triggering drug release by an external magnetic field. Mater. Des. 2018, 152, 78–87. [Google Scholar] [CrossRef]
Characteristic Band Number | Band Assignments |
---|---|
1 | N–H stretch amides |
2 | C–H stretching bond in CH2 and CH3 groups |
3 | |
4 | N=C=O (isocyanate) stretching |
5 | C=O & C=C conjugated stretching |
6 | NO2 aliphatic nitro group |
7 | N–H bending |
8 | Nitro compounds NO2 asymmetric |
9 | C–O–C asymmetrical stretching |
10 | N–H bending and C–N stretching |
11 | Carbonates |
12 | |
13 | Alkene sp2 CH bending |
14 | Fe-O stretching splitted bands |
15 |
Sample | ΔH (J/g) | Error |
---|---|---|
Polyurea | −33.6 | 4.29 |
Magnetite 1% | −51.6 | 6.59 |
Magnetite 3% | −70.6 | 9.02 |
Magnetite Pure | −65.7 | 8.39 |
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Aboelkheir, M.; Gomes, F.; Meiorin, C.; Galdino, T. Tenebrio molitor Larvae-Based Magnetic Polyurea Employed as Crude Oil Spill Removal Tool. Materials 2022, 15, 5063. https://doi.org/10.3390/ma15145063
Aboelkheir M, Gomes F, Meiorin C, Galdino T. Tenebrio molitor Larvae-Based Magnetic Polyurea Employed as Crude Oil Spill Removal Tool. Materials. 2022; 15(14):5063. https://doi.org/10.3390/ma15145063
Chicago/Turabian StyleAboelkheir, Mostafa, Fernando Gomes, Cintia Meiorin, and Tiago Galdino. 2022. "Tenebrio molitor Larvae-Based Magnetic Polyurea Employed as Crude Oil Spill Removal Tool" Materials 15, no. 14: 5063. https://doi.org/10.3390/ma15145063