Structural-group composition and properties of heavy oil asphaltenes modified with sulfuric acid

Yakubov, M. R.; Gryaznov, P. I.; Yakubova, S. G.; Tazeeva, E. G.; Mironov, N. A.; Milordov, D. V.

doi:10.1080/10916466.2016.1230751

Cited by 24 publications

(14 citation statements)

References 6 publications

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“…This dependence is clearly traced between the samples of initial asphaltenes (SA-0) and samples SA-5, SA-10, SA-30 and SA-60. For the SA-30 sample, the mass fraction of sulfur was higher than for the other samples; an analogous pattern of the non-linear dependence between the sulfur content and the sulfonation severity has been observed in our previous studies on asphaltenes sulfonation [24,26]. Further sulfonation (with a contact time of more than 60 min) does not lead to a noticeable increase in either the sulfur content or the total acid value of the material.…”

Section: Resultssupporting

confidence: 84%

“…Such polyaromatic hydrocarbons are formed in the oil industry as by-products, mainly in tar deasphalting plants; their further disposal is part of the more general problem of heavy oil residues disposal. It was shown earlier that by sulfonating asphaltenes, ion-exchange materials can be obtained that are applicable for water treatment [24][25][26]; some preliminary data on the catalytic properties of these materials were also reported [27]. In this work, the sulfonation of asphaltenes is used as an approach for the preparation of non-porous acid catalysts, as a result of which a set of samples with different sulfonation degrees was obtained.…”

Section: Introductionmentioning

confidence: 88%

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Non-Porous Sulfonic Acid Catalysts Derived from Vacuum Residue Asphaltenes for Glycerol Valorization via Ketalization with Acetone

et al. 2021

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In this study, an approach for the preparation of heterogeneous acid catalysts based on asphaltenes isolated from vacuum residue is proposed. Varying the conditions for the sulfonation of asphaltenes made it possible to obtain materials with an acid value of 1.16 to 2.76 meq g–1 and a total sulfur content of 6.4 to 12.3 wt%. The samples obtained were characterized by acid-base titration, nitrogen adsorption, sulfur elemental analysis and transmission electron microscopy techniques, and were studied as potential acid catalysts in the ketalization reaction between glycerol and acetone. Sulfonated asphaltenes (SA) were characterized by a homogeneous distribution of sulfonic groups over the granule surface and an almost complete absence of a porous structure. The ketalization reaction in the presence of SA proceeded without intradiffusion restrictions; as a result of which, their activity was higher than for known heterogeneous catalysts. The most active SA sample (total acid value, 1.16 meq g–1) had an apparent activation energy of 18.0 kJ mol–1, which was lower than the value obtained for the zeolite BEA-40 (29–53 kJ mol–1) and the Amberlyst 36 resin (27 kJ mol–1), and was close to the value for the homogeneous p-TSA catalyst (14.5 kJ mol–1). The SA heterogeneous catalysts did not show any acid leaching and had no loss of activity after five catalytic cycles, with the total turnover number TON = 7247.

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Section: Resultssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 88%

Non-Porous Sulfonic Acid Catalysts Derived from Vacuum Residue Asphaltenes for Glycerol Valorization via Ketalization with Acetone

et al. 2021

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“…Moreover, the phosphochlorinated-asphaltene reacted with polypropylene oxide to produce amphiphilic surfactants that act as asphaltenes dispersants for heavy crude oil [ 16 ]. The asphaltene was also converted to anionic amphiphiles by sulfonation and used as capping for magnetite to use as oil spill collectors for heavy crude oil [ 17 , 18 ]. However, the preparations of amphiphilic asphaltenes ionic liquids (ILs) and polymeric surfactants were not reported elsewhere in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Application of New Amphiphilic Asphaltene Ionic Liquid Polymers to Demulsify Arabic Heavy Petroleum Crude Oil Emulsions

et al. 2020

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Asphaltenes are heavy petroleum crude oil components which limit the production of petroleum crude oil due to their aggregation and their stabilization for all petroleum crude oil water emulsions. The present study aimed to modify the chemical structures of isolated asphaltenes by converting them into amphiphilic polymers containing ionic liquid moieties (PILs) to demulsify the emulsion and replace the asphaltene layers surrounding the oil or water droplets in petroleum crude oil emulsions. The literature survey indicated that no modification occurred to produce the PILs from the asphaltenes. In this respect, the asphaltenes were modified via oxidation of the lower aliphatic chain through carboxylation followed by conversion to asphaltene acid chloride that reacted with ethoxylated N-alkyl pyridinium derivatives. Moreover, the carboxylation of asphaltenes was carried out through the Diels–Alder reaction with maleic anhydride that was linked with ethoxylated N-alkyl pyridinium derivatives to produce amphiphilic asphaltene PILs. The produced PILs from asphaltenes acid chloride and maleic anhydride were designated as AIL and AIL-2. The chemical structure and thermal stability of the polymeric asphaltene ionic liquids were evaluated. The modified structure of asphaltenes AIL and AIL-2 exhibited different thermal characteristics involving glass transition temperatures (Tg) at −68 °C and −45 °C, respectively. The new asphaltenes ionic liquids were adsorbed at the asphaltenes surfaces to demulsify the heavy petroleum crude emulsions. The demulsification data indicated that the mixing of AIL and AIL-2 100 at different ratios with ethoxylated N-alkyl pyridinium were demulsified with 100% of the water from different compositions of O:W emulsions 50:50, 90:10, and 10:90. The demulsification times for the 50:50, 90:10, and 10:90 O:W emulsions were 120, 120, and 60 min, respectively. The interaction of the PILs with asphaltene and mechanism of demulsification was also investigated.

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“…PHMOCs usually give deposits due to their ability to aggregate and associate [15,16] and their high content is regarded as an adverse factor for recovery, transport, and upgrading of oil. On the contrary, PHMOCs can lay the foundation for the preparation of a large number of various valuable materials due to their structural manifold and their potential still not discovered to full extent [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33].…”

Section: Introductionmentioning

confidence: 99%

“…Asphaltenes modified with styrene-ethylene-butylene-styrene (SEBS) as precursor for isotropic pitch-based carbon fiber [29]; with maleic anhydride -for the synthesis of the polystyrene-asphaltene graft copolymer, able to react chemically with paving asphalt components [30]. Asphaltenes modified with acid acquire high ion exchange and adsorption properties [17,[31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Heavy Oil Residues: Application as a Low-Cost Filler in Polymeric Materials

et al. 2019

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Deposits of oil sands, bitumen, extra-heavy oil, and heavy oil appear in more than 70 countries all over the world and the fraction of oil recovered gradually increases. High content of poly-condensed high molecular weight oil components (PHMOCs), which may amount up to 50-60% depending on conditions of oil formation, is the main difference of heavy oil and bitumen from conventional oil. PHMOCs can lay the foundation for the preparation of a large number of valuable materials due to their structural manifold and their potential still not discovered to full extent. This work is devoted to the study of the effect of PHMOCs on properties of the composition materials prepared from polyethylene matrix. An «asphalt» – industrial product of deasphalting of tar, as well as asphaltenes and resins isolated from heavy oil, were used as a source of PHMOCs. HDPE and fillers were characterized using MALDI, FTIR, DSC and TGA. For the new composite materials we evaluated the physicomechanical properties, the thermal decomposition characteristics (by TGA), and the accumulation rate of carbonyl groups in the oxidized polymer (on FTIR). Studies of new composite materials showed that the introduction of filler in an amount of up to 4% in a polyethylene matrix does not lead to a significant change in the physicomechanical properties, but for a number of parameters they are improved. It also figured out that the addition of PHMOCs to polyethylene makes it unnecessary to stabilize the resulting compositions with stabilizers of thermal oxidative degradation. Results of experimental studies indicate that industrial residue - «asphalt» is a promising filler and low cost of this stock renders it perfect source for the industry of polymer materials.

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Structural-group composition and properties of heavy oil asphaltenes modified with sulfuric acid

Cited by 24 publications

References 6 publications

Non-Porous Sulfonic Acid Catalysts Derived from Vacuum Residue Asphaltenes for Glycerol Valorization via Ketalization with Acetone

Non-Porous Sulfonic Acid Catalysts Derived from Vacuum Residue Asphaltenes for Glycerol Valorization via Ketalization with Acetone

Synthesis and Application of New Amphiphilic Asphaltene Ionic Liquid Polymers to Demulsify Arabic Heavy Petroleum Crude Oil Emulsions

Heavy Oil Residues: Application as a Low-Cost Filler in Polymeric Materials

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