High viscosity-reducing performance oil-soluble viscosity reduction agents containing acrylic acid ester as monomer for heavy oil with high asphaltene content

Zhu, Lijun; Wang, Yongjie; Wang, Shoulong; Huo, Tian; Jing, Xiaohui; Li, Aifen; Xia, Daohong

doi:10.1016/j.petrol.2017.12.079

Cited by 24 publications

(4 citation statements)

References 31 publications

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“…The preferential solvation of Asp in maltenes can be employed to assess additives for mitigating the Asp instability problem. In the absence of adverse effects of the additive on other properties that may affect Asp stability, including its self-aggregation, CO viscosity, − and CO/water emulsion stability, efficient additives should accumulate in the solvation layer of Asp particles, where they displace nonsolvent components, in particular the saturates. Work in this direction is underway.…”

Section: Discussionmentioning

confidence: 99%

Dissolution of Asphaltene in Binary Mixtures of Organic Solvents and Model Maltenes: Unambiguous Evidence for Asphaltene Preferential Solvation and Relevance to Assessing the Efficiency of Additives for Asphaltene Stabilization

et al. 2018

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Asphaltenes (Asps) are operationally defined as the toluene-soluble but n-pentane- or n-heptane-insoluble fractions, e.g., of crude oils. Therefore, there is intense interest in determining the concentration of n-heptane required to precipitate Asps from their solutions in particular media (solvents, solvent mixtures, and maltenes). Here, we report on the dependence of Asp dissolution in binary mixtures of n-heptane (solvent 1, S1)/organic solvent (solvent 2, S2) over the entire mole fraction range of S2, χ S2 , and in few selected maltene models (n-heptane + S2 + benzothiazole + n-octyl-1-napthoate). The S2 employed were benzonitrile, cyclohexanone, ethyl benzoate, 1-methylnaphthalene, tetrahydropyran, and toluene. For all S2 and model maltenes, the dependence of wt % dissolved Asp (determined by mass and UV/vis absorbance) on χ S2 was nonlinear. We attribute this nonlinear, i.e., nonideal dissolution behavior to “preferential solvation” of the Asp by a component(s) of the medium (binary solvent mixtures and maltenes). Although the occurrence of “solvent sorting” during Asp dissolution was alluded to, this is the first direct and unambiguous evidence for its occurrence. We used solvatochromism to corroborate our rationale about the origin of the Asp nonideal dissolution behavior. The term solvatochromism refers to the effect of the solvent on the color of solvatochromic probes, substances whose spectra are sensitive to the properties of the liquid medium, e.g., its empirical polarity, E T (probe). Recently, we used (E)-2,6-di-tert-butyl-4-[2-(1-hexylquinolin-1-ium-4-yl)vinyl]phenolate, HxQMBu2) to study Asp dissolution in pure solvents and model maltenes. We showed that E T (HxQMBu2) correlates linearly with Hildebrand solubility parameters of pure solvents as well as with lg (wt % dissolved Asps). In the present work, we studied the solvatochromic response of HxQMBu2 in the above-mentioned n-heptane/S2 binary mixtures. Except for toluene/n-heptane mixtures, plots of E T (HxQMBu2) versus χS2 were nonlinear due to probe preferential solvation. We successfully fitted a solvation model to the solvatochromic and Asp dissolution data and extracted the enrichment of the solvation layers in the more polar component(s) of the binary mixture and model maltenes. Our results bear on the assessment of additives employed to stabilize Asps: in the absence of adverse effects of the additive on other properties (e.g., viscosity and water/oil emulsion stability), efficient additives should accumulate in the solvation layer of Asp particles where they displace the nonsolvents, e.g., the saturates.

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Section: Discussionmentioning

confidence: 99%

Dissolution of Asphaltene in Binary Mixtures of Organic Solvents and Model Maltenes: Unambiguous Evidence for Asphaltene Preferential Solvation and Relevance to Assessing the Efficiency of Additives for Asphaltene Stabilization

et al. 2018

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“…Liu et al 14 explored the application of synthetic terpolymers in reducing the viscosity of ultraheavy oils, discovering that higher percentages of alkyl chains resulted in better viscosity reduction effects. Zhu et al 15 found that polymers containing benzene and ester groups can dissolve and decompose asphaltenes and thus contribute to viscosity reduction in heavy oils. Quan and Xing 16 of VR with asphaltene through hydrogen bonding and improved the dispersion of the asphaltene.…”

Section: Introductionmentioning

confidence: 99%

Pathway of Oil-Soluble Additives to Reduce Heavy Crude Oil Viscosity Depends on the Molecular Characteristics of Asphaltene

Li,

Han,

et al. 2024

Energy Fuels

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The high viscosity of heavy crude oil hinders its efficient production and transportation. Oil-soluble viscosity reducers (VRs) are crucial for ensuring the world's energy needs are met; however, the molecular mechanism underlying the reduction of viscosity remains unclear, which obstructs the selection of VRs for specific heavy oil reservoirs and further development of VRs. In this work, using molecular dynamics (MD) and quantum mechanics (QM) simulations, modeled heavy oils and VRs were employed to explore the molecular pathways of VRs to reduce heavy oil viscosity. Taking structural analyses and interaction energy analyses together, for a small asphaltene surrogate whose molecules interact with each other via hydrogen bonds, VR molecules were interspersed within the spatial hydrogen bond network, leading to a relaxation of network configuration. However, for another asphaltene surrogate that tends to aggregate through face-to-face stacking, the viscosity reducer could adsorb onto the asphaltenes, resulting in a shielding effect on asphaltene nanoaggregates from other heavy oil components. Thus, the viscosity reduction pathways should be chosen according to the molecular characteristics of the asphaltenes. These molecular insights and implications are expected to facilitate the future design and application of oil-soluble VRs.

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“…Viscosity reducer molecules are dispersed and penetrated into the resin and asphaltene sheet-like molecules by means of hydrogen bonds, disassembling the aggregates formed by overlapping planes and forming a new poorly ordered and more dispersed structure, thus playing the role of viscosity reduction. , Viscosity reducers have been widely used in reservoir exploitation and oil recovery improvement. , Guo et al used the orthogonal method to synthesize an oil-soluble polybasic copolymer viscosity reducer for heavy oil. Two new monomers, acrylic acid phenethyl alcohol ester and benzyl acrylate, were synthesized by Zhu et al, and six copolymers were synthesized by free radical copolymerization with styrene, octadecyl acrylate, and N -methoxyphenyl maleimide. Xu et al synthesized magnetic graphene oxide (MgO) and assisted microwave to reduce the viscosity of heavy oil.…”

Section: Introductionmentioning

confidence: 99%

“… 18 , 19 Guo et al 20 used the orthogonal method to synthesize an oil-soluble polybasic copolymer viscosity reducer for heavy oil. Two new monomers, acrylic acid phenethyl alcohol ester and benzyl acrylate, were synthesized by Zhu et al, 21 and six copolymers were synthesized by free radical copolymerization with styrene, octadecyl acrylate, and N -methoxyphenyl maleimide. Xu et al 22 synthesized magnetic graphene oxide (MgO) and assisted microwave to reduce the viscosity of heavy oil.…”

Section: Introductionmentioning

confidence: 99%

Mechanism Analysis of Heavy Oil Viscosity Reduction by Ultrasound and Viscosity Reducers Based on Molecular Dynamics Simulation

Zhang

Xie

et al. 2022

ACS Omega

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Ultrasound and viscosity reducers are commonly used methods to reduce the viscosity of heavy oil. In order to compare the viscosity reduction effects of ultrasound and viscosity reducers and study their mechanism of interaction on heavy oil, molecular dynamics simulation was carried out in this paper. First, a molecular model of heavy oil composed of asphaltene, resin, aromatic hydrocarbon, and saturated hydrocarbon was established in this work. Through molecular dynamics simulation, the different effects of ultrasound and viscosity reducers on the viscosity reduction rate, hydrogen bond number, hydrogen bond type, and occupation rate were obtained, and the viscosity reduction mechanism of ultrasound and viscosity reducers was analyzed. By calculating the viscosity reduction rate and the number of hydrogen bonds of five oil-soluble viscosity reducers with or without ultrasound, it was found that the types of hydrogen bonds affecting the viscosity reduction effect were different with or without ultrasound or viscosity reducer, and the type and content of viscosity reducer would affect the effect of ultrasonic viscosity reduction. The amplitude, frequency, and temperature of ultrasound were also the factors affecting the effect of viscosity reducers. The simulation results helped to explain the mechanism of jointly reducing the viscosity of heavy oil by ultrasound and viscosity reducers from the microscopic point of view and provided a theoretical basis for the industrial application of ultrasound and viscosity reducers to reduce the viscosity of heavy oil.

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High viscosity-reducing performance oil-soluble viscosity reduction agents containing acrylic acid ester as monomer for heavy oil with high asphaltene content

Cited by 24 publications

References 31 publications

Dissolution of Asphaltene in Binary Mixtures of Organic Solvents and Model Maltenes: Unambiguous Evidence for Asphaltene Preferential Solvation and Relevance to Assessing the Efficiency of Additives for Asphaltene Stabilization

Dissolution of Asphaltene in Binary Mixtures of Organic Solvents and Model Maltenes: Unambiguous Evidence for Asphaltene Preferential Solvation and Relevance to Assessing the Efficiency of Additives for Asphaltene Stabilization

Pathway of Oil-Soluble Additives to Reduce Heavy Crude Oil Viscosity Depends on the Molecular Characteristics of Asphaltene

Mechanism Analysis of Heavy Oil Viscosity Reduction by Ultrasound and Viscosity Reducers Based on Molecular Dynamics Simulation

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