Guanidine-functionalized Fe<sub>3</sub>O<sub>4</sub> magnetic nanoparticles as basic recyclable catalysts for biodiesel production

Santos, Evelyn C. S.; Santos, Thiago C. dos; Guimarães, R. B.; Ishida, Lina; Freitas, R. S.; Ronconi, Célia M.

doi:10.1039/c5ra07331f

Cited by 54 publications

(25 citation statements)

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“…Though the catalyst was reported to be highly active, stable and recyclable, it is likely to be very expensive as it is a combination of two synthetic chemical substances. Guanidine-functionalized magnetic catalyst for biodiesel production was reported in literature 18 . The catalyst was synthesized through three steps, (1) co-precipitation of Fe(II) and Fe(III) ions, (2) surface modification with chloropropyl groups and (3) functionalization with guanidine.…”

Section: Introductionmentioning

confidence: 99%

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Ajala

Ayinla

et al. 2020

Sci Rep

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Waste-iron-filling (WIF) served as a precursor to synthesize α- through the co-precipitation process. The α- was converted to solid acid catalysts of RBC500, RBC700, and RBC900 by calcination with temperatures of 500, 700 and 900 °C respectively and afterwards sulfonated. Among the various techniques employed to characterize the catalysts is Fourier transforms infrared spectrometer (FT-IR), X-ray diffraction (XRD and Scanning electron microscopy (SEM). Performance of the catalysts was also investigated for biodiesel production using waste cooking oil (WCO) of 6.1% free fatty acid. The XRD reveals that each of the catalysts composed of Al– . While the FT-IR confirmed acid loading by the presence of groups. The RBC500, RBC700, and RBC900 possessed suitable morphology with an average particle size of 259.6, 169.5 and 95.62 nm respectively. The RBC500, RBC700, and RBC900 achieved biodiesel yield of 87, 90 and 92% respectively, at the process conditions of 3 h reaction time, 12:1 MeOH: WCO molar ratio, 6 wt% catalyst loading and 80 °C temperature. The catalysts showed the effectiveness and relative stability for WCO trans-esterification over 3 cycles. The novelty, therefore, is the synthesis of nano-solid acid catalyst from WIF, which is cheaper and could serve as an alternative source for the ferric compound.

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Section: Introductionmentioning

confidence: 99%

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Ajala

Ayinla

et al. 2020

Sci Rep

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“…17 These particles have been obtained in aqueous medium, following a modified Massart procedure. 27,28 Briefly, 75 mL of a 25% NH 3 aqueous solution was rapidly added to a solution containing 488 mL of 0.334 mol L -1 FeCl 3 and 0.175 mol L -1 FeCl 2 , under vigorous stirring and at room temperature. The particles were isolated by magnetic decantation after 5 min and washed three times with distilled water.…”

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confidence: 99%

Studies of the Colloidal Properties of Superparamagnetic Iron Oxide Nanoparticles Functionalized with Platinum Complexes in Aqueous and PBS Buffer Media

Silva

Marciello

Morales

et al. 2016

J. Braz. Chem. Soc.

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This work has focused on the synthesis of three nanosystems composed of superparamagnetic iron oxide nanoparticles (SPIONs) coated either with a carboxylate platinum(IV) complex (PD = cis,cis, ) 2 Cl 2 (HOOCCH 2 CH 2 COO)(OH)]) or with platinum(II) complex functionalized dextrans (DexPt1 = [Pt(Dex-NH 2 )Cl 3 ] and DexPt2 = [Pt(Dex-NH 2 )(NH 3 ) 2 (H 2 O)]). All nanosystems have shown superparamagnetic behavior. Powder X-ray diffraction (XRD) has confirmed that the SPIONs were iron oxide phase and transmission electron microscopy (TEM) has shown average size of 6 nm (M6). Characterization of the nanosystems by inductively coupled plasma atomic emission spectroscopy (ICP AES) has revealed the presence of platinum on their surface (M6@PD, 0.54 mmol g -1 of Fe and M6@CA@DexPt1-2, 0.32-1.20 mmol g -1 of Fe); infrared spectroscopy (IR) and thermogravimetric and differential thermal analyses (TG-DTA) have confirmed the presence of dextran. Furthermore, the colloidal properties of these nanosystems (M6@PD and M6@CA@DexPt1-2) have been evaluated in water and in PBS buffer. Although M6@PD has shown good colloidal dispersion in water in the pH range of 2.0-8.0, the system underwent rapid agglomeration in PBS buffer. The M6@CA@DexPt1-2 nanosystems have exhibited improved colloidal behavior both in water and in PBS, where hydrodynamic sizes were kept below 100 nm over a large pH range (2.0-12.0). Furthermore, the latter systems have displayed isoelectric points below pH 5.0 and low surface charges at pH 7.0 (ζ-potential = −10 mV) and therefore PBS did not affect their colloidal stability.Keywords: colloidal stability, dextran, iron oxide, platinum complexes, superparamagnetism IntroductionSuperparamagnetic iron oxide nanoparticles (SPIONs) have been widely investigated for biomedical purposes. Magnetic resonance imaging, 2-4 hyperthermia 5-7 and drug delivery [8][9][10][11][12] are some of the practical applications displayed by SPIONs. These nanomaterials are promising due to the biocompatibility of the iron oxide cores, e.g., magnetite (Fe 3 O 4 ) and maghemite (γ-Fe 2 O 3 ). 13 Furthermore, their surfaces can be easily modified, allowing for the tuning of pharmacokinetic properties. [14][15][16] One of the key features for biomedical applications of SPIONs is their aqueous colloidal stability. 17 Therefore, surface functionalization plays a relevant role on the balance of attractive forces, such as dispersion forces and dipole-dipole interactions that determine their agglomeration.18 Carboxylate-, phosphonate-and aminosilane-based derivatives have been widely used to coat SPIONs in order to prevent aggregation, mainly by electrostatic interactions due to the formation of an electrical double layer. [16][17][18][19] However, this kind of colloidal dispersion is strongly affected by physiological pH and ionic strength. 17 Coating nanoparticles with polymers, such as dextran (Dex) or poly(ethylene glycol) (PEG), is a judicious strategy to prevent SPIONs from aggregation, 13,20 diminishing opsonization and increasing circulat...

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“…[30][31][32][33] Guanidine and its derivatives have been used in different organic reactions as a strong organobase catalyst. [34][35][36] Additionally, guanidines are found to be asymmetric catalysts in various reactions, including Henry, aza-Michael, phospha-Michael, Diels-Alder, protonation, electrophilic amination, and nucleophilic epoxidation reactions. [37] Separation and recycling of the catalyst are important factors that have been highly regarded in recent years.…”

Section: Introductionmentioning

confidence: 99%

Design, preparation, and characterization of Fe₃O₄ nanoparticles encapsulating β‐cyclodextrin‐bearing guanidine as a highly efficient and reusable heterogeneous base catalyst for synthesis of 3,4‐dihydropyrano[3,2‐c]chromenes

Rahmatinejad

Naeimi

2020

Applied Organom Chemis

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Chromene substructure is an important structural motif present in a variety of medicines, natural products, and materials showing biological activities. Here, a simple and convenient procedure for the synthesis of 3,4‐dihydropyrano[3,2‐c]chromene derivatives is described. For this purpose, Fe3O4 nanoparticles supported on β‐cyclodextrin‐guanidine were successfully prepared and used as catalyst. The structure of this catalyst was assigned by Fourier transform infrared spectroscopy, X‐ray diffraction, scanning electron microscopy, thermal gravimetric analysis, and vibrating sample magnetometer techniques. The prepared nanocomposites were used as a highly active, heterogeneous, and reusable nanocatalyst for the one‐pot, three‐component reaction of 4‐hydroxycoumarin, aromatic aldehydes, and ethyl cyanoacetate. This method has advantages such as mild conditions, high yields, easy workup and simple purification of products, little catalyst loading, cost efficiency, and reusability of the catalyst.

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Guanidine-functionalized Fe₃O₄ magnetic nanoparticles as basic recyclable catalysts for biodiesel production

Abstract: Two organic superbases, 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) and 1,1,3,3-tetramethylguanidine (TMG), were anchored onto silica-coated and uncoated iron oxide nanoparticles, resulting in three recoverable basic nanocatalysts.

Cited by 54 publications

References 46 publications

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Studies of the Colloidal Properties of Superparamagnetic Iron Oxide Nanoparticles Functionalized with Platinum Complexes in Aqueous and PBS Buffer Media

Design, preparation, and characterization of Fe₃O₄ nanoparticles encapsulating β‐cyclodextrin‐bearing guanidine as a highly efficient and reusable heterogeneous base catalyst for synthesis of 3,4‐dihydropyrano[3,2‐c]chromenes

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Guanidine-functionalized Fe3O4 magnetic nanoparticles as basic recyclable catalysts for biodiesel production

Abstract: Two organic superbases, 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) and 1,1,3,3-tetramethylguanidine (TMG), were anchored onto silica-coated and uncoated iron oxide nanoparticles, resulting in three recoverable basic nanocatalysts.

Cited by 54 publications

References 46 publications

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Nano-synthesis of solid acid catalysts from waste-iron-filling for biodiesel production using high free fatty acid waste cooking oil

Studies of the Colloidal Properties of Superparamagnetic Iron Oxide Nanoparticles Functionalized with Platinum Complexes in Aqueous and PBS Buffer Media

Design, preparation, and characterization of Fe3O4 nanoparticles encapsulating β‐cyclodextrin‐bearing guanidine as a highly efficient and reusable heterogeneous base catalyst for synthesis of 3,4‐dihydropyrano[3,2‐c]chromenes

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Guanidine-functionalized Fe₃O₄ magnetic nanoparticles as basic recyclable catalysts for biodiesel production

Design, preparation, and characterization of Fe₃O₄ nanoparticles encapsulating β‐cyclodextrin‐bearing guanidine as a highly efficient and reusable heterogeneous base catalyst for synthesis of 3,4‐dihydropyrano[3,2‐c]chromenes