Novel periodic mesoporous organosilicas containing pyromellitimides and their application for the photodegradation of asphaltenes

Andrade, Luana dos Santos; Otubo, Larissa; Castanheira, Bruna; Brochsztain, Sergio

doi:10.1016/j.micromeso.2020.110740

Cited by 6 publications

(2 citation statements)

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“…Petroleum asphaltenes were obtained from a sample of petroleum from the Campos basin (Brazil) utilizing precipitation with n -heptane (800 mL heptane/20 g of petroleum), which is known as the SARA procedure (IP-143). , CTAB and SDS (sodium dodecyl sulfate) were purchased from Sigma-Aldrich, St Louis, MO. Chloroform was from Labsynth, Diadema, SP, Brazil.…”

Section: Methodsmentioning

confidence: 99%

Harvesting of Surfactant-Solubilized Asphaltenes by Magnetic Nanoparticles

et al. 2022

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Asphaltenes are a severe problem for the oil industry. The high content of aromatic and aliphatic hydrocarbons in asphaltenes poses a challenge for efficient methods of the solubilization and degradation of their components. The main goal of this study was to investigate an efficient and innovative method for asphaltene solubilization with surfactants to produce supramolecular aggregates with affinity by magnetic nanoparticles (Fe 3 O 4 ) for magnetic separation and degradation. Asphaltene mixed with the cationic surfactant cetyltrimethylammonium bromide (CTAB) was both solubilized in chloroform and the solvent dried with N 2 to produce a film that was resuspended in water and formed a stable colloid with asphaltene incorporated in CTAB micelles. The suspensions of CTAB/asphaltene supramolecular aggregates obtained at different surfactant/asphaltene ratios were characterized by dynamic and static light scattering (DLS and SLS) and by electrophoretic mobility for ζ potential determination. CTAB concentrations of 30 and 60 mM produced spherical supramolecular aggregates (SMAs) of size between 100 and 200 nm with polydispersity. The ζ potential of CTAB micelles loaded with asphaltenes increased from +9.17 +/− 4.6 to +56.7 +/− 5.8 eV. Electron paramagnetic resonance revealed that asphaltene forms stable free radicals in CTAB micelles. Classical molecular dynamics simulations were also used to study interactions of the functional groups of asphaltenes. The association with CTAB micelles provided the binding affinity of asphaltenes for nanoparticulate magnetite (Fe 3 O 4 ) and precipitation of the most CTAB content. In this condition, Fe 3 O 4 promoted the degradation of asphaltenes to low molecular mass products. Therefore, incorporation in CTAB micelles is a simple and innovative method contributing to asphaltene removal, degradation, and possible conversion to products with aggregated value.

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Section: Methodsmentioning

confidence: 99%

Harvesting of Surfactant-Solubilized Asphaltenes by Magnetic Nanoparticles

et al. 2022

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“…The syntheses of analogous pyromellitimide (PMI) and perylenediimidediimide (PDI) derivatives, namely, N , N ′-bis[3-(triethoxysilyl)propyl]pyromellitimide − and N , N ′-bis[3-(triethoxysilyl)propyl]-3,4,9,10-perylenediimidediimide, − have already been reported. In a previous paper, we reported the extraction of NDI-silane by reacting NTCA over (3-aminopropyl)triethoxysilane, then precipitating a solid in petroleum ether, and finally extracting the pure compound in acetone .…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of a Disilylated Naphthalenediimide Molecular Crystal: Perspectives for Organosilica Mesoporous Materials

Gabriel de Assis,

de Oliveira Junior,

Escote

et al. 2024

ACS Appl. Eng. Mater.

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Naphthalenetetracarboxylic diimides (NDIs) are efficient electron acceptors due to their high electron affinity. They are applied in heterogeneous catalysis and organic electronics. In this work, we report, for the first time, the synthesis of N, N′-bis[3-(triethoxysilyl)propyl]-1,4,5,8-naphthalenediimide (NDI-silane) as a molecular crystal obtained from recrystallization in petroleum ether. The compound is stable in air conditions and chloroform solution. Its crystal structure was determined by singlecrystal X-ray diffraction. We have characterized the intermolecular dispersive interactions by density functional theory calculations, indicating that the stability of the crystal in air conditions is related to dispersive interactions. Furthermore, we characterize the optical and photoelectrical properties of thin NDI-silane films, demonstrating photoinduced conductivity over a wide range of temperatures (10−300 K). Remarkably, a venture of NDI-based organosilica can be obtained from stable NDI-silane crystals, prominent materials in organoelectronics and photocatalysis. As a proof of concept, we prepare mesoporous organosilicas with 100% NDI-silane using the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate as a templating and sol−gel catalytic agent. These materials show a well-formed organosilica network, presenting only T 3 and T 2 Si species, as probed by solid-state 29 Si NMR. As a result, the mesoporous materials are considerably more resistant to thermal degradation than the crystals, being stable up to 450 °C. According to N 2 adsorption isotherms and transmission electron microscopy images, they demonstrate microporous and mesoporous structures associated with narrow slitlike pores.

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