Low-cost N-methylpyrrolidone-based coordinated ionic liquids as extractants for separating aromatics from aliphatics

Yu, Hui; Li, Xinyu; Geng, Chuanqi; Wu, Xiaojia; Zhang, Fan; Tian, Shichao; Zhou, Zhiyong; Ren, Zhongqi

doi:10.1016/j.seppur.2022.122149

Cited by 7 publications

(4 citation statements)

References 36 publications

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“…The findings demonstrated the potential of [NMP][MSA] as a promising extractant for the high-efficiency separation of aromatics/aliphatics. Yu et al prepared several NMP-based ILs coordinated with metal salts to intensify the separation performance of aromatics/aliphatics by adding additional π–π interactions between aromatics and C=O bonds in NMP molecules. It was found that NMP-0.1Fe(NO 3 ) 3 ·9H 2 O had high selectivity for toluene/ n -heptane and toluene/cyclohexane.…”

Section: Aromatics Extraction With Ilsmentioning

confidence: 99%

“…Extraction agent selection is undoubtedly a key factor in achieving efficient liquid–liquid extraction. Generally, organic solvents with high boiling points are used as extraction agents, such as sulfolane (SUL), N -methylpyrrolidone (NMP), dimethyl sulfoxide (DMSO), glycols, N -formylmorpholine, and silicone oil. − Among them, SUL is widely used in aromatic hydrocarbon extraction due to its special properties . However, these solvents have unavoidable drawbacks, including (i) being partially dissolved in hydrocarbons, causing secondary pollution of products; (ii) inevitable volatile losses; and (iii) poor thermal stability resulting in solvent degradation during regeneration processes.…”

Section: Introductionmentioning

confidence: 99%

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Hydrocarbon Extraction with Ionic Liquids

Yu,

Dai,

Liu

et al. 2024

Chem. Rev.

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Separation and reaction processes are key components employed in the modern chemical industry, and the former accounts for the majority of the energy consumption therein. In particular, hydrocarbon separation and purification processes, such as aromatics extraction, desulfurization, and denitrification, are challenging in petroleum refinement, an industrial cornerstone that provides raw materials for products used in human activities. The major technical shortcomings in solvent extraction are volatile solvent loss, product entrainment leading to secondary pollution, low separation efficiency, and high regeneration energy consumption due to the use of traditional organic solvents with high boiling points as extraction agents. Ionic liquids (ILs), a class of designable functional solvents or materials, have been widely used in chemical separation processes to replace conventional organic solvents after nearly 30 years of rapid development. Herein, we provide a systematic and comprehensive review of the state-of-the-art progress in ILs in the field of extractive hydrocarbon separation (i.e., aromatics extraction, desulfurization, and denitrification) including (i) molecular thermodynamic models of IL systems that enable rapid large-scale screening of IL candidates and phase equilibrium prediction of extraction processes; (ii) structure–property relationships between anionic and cationic structures of ILs and their separation performance (i.e., selectivity and distribution coefficients); (iii) IL-related extractive separation mechanisms (e.g., the magnitude, strength, and sites of intermolecular interactions depending on the separation system and IL structure); and (iv) process simulation and design of IL-related extraction at the industrial scale based on validated thermodynamic models. In short, this Review provides an easy-to-read exhaustive reference on IL-related extractive separation of hydrocarbon mixtures from the multiscale perspective of molecules, thermodynamics, and processes. It also extends to progress in IL analogs, deep eutectic solvents (DESs) in this research area, and discusses the current challenges faced by ILs in related separation fields as well as future directions and opportunities.

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Section: Aromatics Extraction With Ilsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydrocarbon Extraction with Ionic Liquids

Yu,

Dai,

Liu

et al. 2024

Chem. Rev.

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“…Owing to their low volatility 13 and adjustable structure, 14 ionic liquids have been widely employed and their capability in the separation of alkanes and aromatics has also been studied in depth-many ionic liquids have been reported used as extraction agents for alkanes and aromatics. [15][16][17][18][19] The nitrogen-containing heterocyclic structure of imidazole and pyridine can form a good π-π complexation with aromatics, which assists in separating aromatics and alkanes.…”

Section: Introductionmentioning

confidence: 99%

A novel symmetrically structured protonated ionic liquids for alkane de‐aromatization

Geng,

Wu,

Jin

et al. 2024

AIChE Journal

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The efficient separation of aromatics/alkanes is important for the efficient utilization of fossil resources. Based on the influence of ionic symmetry structure on the polarity, melting point, interaction force, and spatial site resistance of ionic liquid solvents, a protonic ionic liquid with anionic and cationic double symmetry structure [DMI][FeCl4] was designed and synthesized for alkane de‐aromatization process, which enhances the Van der Waals forces dominated by dispersed forces with aromatics, and thus enhances the extraction efficiency of aromatic. For the binary system of dodecane/decalin + tetralin/1‐methylnaphthalene, and two simulated oil systems of six‐component straight‐sun diesel fuel and hydrofinishing LCO, [DMI][FeCl4] showed excellent de‐aromatization effects. The selectivity coefficients for monocyclic and bicyclic aromatic hydrocarbons can reach 150 and 480, respectively. When used in the de‐aromatization process of real oils, about 40% of the aromatic hydrocarbons can be removed by a single extraction using a 1:5 O/A ratio.

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“…Both NMP and DMF are on the REACH list of substances of very high concern (SVHC); still, they are used as extraction solvents in several extraction processes. They can be used for liquid–liquid extraction (LLX) of aromatics from mixtures of aliphatic hydrocarbons − or for desulfurization of diesel. − The use of NMP and DMF in these applications could possibly be substituted by several safer solvents such as sulfolane, ,, organic carbonates, ,− γ-valerolactone, N -formylmorpholine, − glycols, − furfural, , ionic liquids − and deep eutectic solvents. ,− …”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Jeřábek,

Štejfa,

Klajmon

et al. 2023

J. Chem. Eng. Data

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Thermodynamic and computational study of a biomass-derived solvent dihydrolevoglucosenone (DLG) and its mixtures with hydrocarbons is presented in this work. Density and dynamic viscosity of DLG were measured within the temperature range of 293.15−353.15 K. Phase behavior of DLG above 183 K was analyzed using heat-flux differential scanning calorimetry, providing data on its melting temperature and enthalpy of fusion. Heat capacity of DLG was measured using a Tian-Calvet calorimeter at temperatures between 253 and 353 K. Two static apparatuses were utilized to measure the vapor pressure of DLG in the temperature range of 253−363 K. A thermodynamically consistent description was achieved by simultaneous correlation of experimental values of phase behavior, heat capacities, vapor pressures, and theoretical calculations. Liquid−liquid equilibria (LLE) data in four binary DLG and hydrocarbons (n-hexane, cyclohexane, n-decane, and ntetradecane) systems were determined using a combination of volumetric, cloud-point, and direct analytical methods. The obtained LLE data were employed to thermodynamically describe the binary mixtures using the nonrandom two-liquid (NRTL) equation and estimate critical points using the Extended-Scaling Law (ESL) equation. Furthermore, the pure-component data developed in this work were used to determine two new sets of parameters for DLG within the perturbed-chain statistical associating fluid theory (PC-SAFT) equation of state: one with and one without the explicit inclusion of the dipole moment of DLG in the model theory. In addition, one more set of parameters for DLG developed earlier by other authors was included. PC-SAFT with all three parameter sets was then examined in terms of its performance regarding the description of the LLE in the systems studied. Both correlations (with optimized k ij ) and pure predictions (k ij = 0) were considered and discussed. Interestingly, it appears that the better PC-SAFT with a particular parameter set for DLG performs for the properties of pure DLG, the worse are the results for the LLE in the DLG + hydrocarbon systems. For example, PC-SAFT with the nonpolar parameters for DLG provided more accurate results for pure DLG than its polar counterparts, while it quantitatively failed for the LLE.

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Low-cost N-methylpyrrolidone-based coordinated ionic liquids as extractants for separating aromatics from aliphatics

Cited by 7 publications

References 36 publications

Hydrocarbon Extraction with Ionic Liquids

Hydrocarbon Extraction with Ionic Liquids

A novel symmetrically structured protonated ionic liquids for alkane de‐aromatization

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

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