Formation mechanisms of Caprolactam-tetraalkyl ammonium halide deep eutectic and its hydrate

Ren, Hongwei; Wang, Xue; Lian, Shaohan; You, Zhang; Duan, Erhong

doi:10.1016/j.saa.2018.12.005

Cited by 8 publications

(6 citation statements)

References 36 publications

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“…When DES was formed, the active hydrogen signal of CPL at 6.86 ppm was greatly weakened and moved downfield to 6.92 ppm due to the formation of hydrogen bonds between the two components. 60 The 1 H NMR results also confirmed that the DES TBAB/2CPL was formed by hydrogen bonding interaction between TBAB and CPL. Extraction of DBT by the CPL-Based DESs.…”

Section: ■ Results and Discussionmentioning

confidence: 61%

“…The nature of interaction in the DES TBAB/2CPL was further analyzed using the 1 H NMR spectra (Figure b). When DES was formed, the active hydrogen signal of CPL at 6.86 ppm was greatly weakened and moved downfield to 6.92 ppm due to the formation of hydrogen bonds between the two components . The 1 H NMR results also confirmed that the DES TBAB/2CPL was formed by hydrogen bonding interaction between TBAB and CPL.…”

Section: Results and Discussionmentioning

confidence: 70%

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Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Yin

Luo

et al. 2022

ACS Sustainable Chem. Eng.

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Deep eutectic solvents (DESs) are considered novel alternatives compared to organic solvents and ionic liquids. However, the low extractive efficiency of fuel oil has limited its wide application in desulfurization of diesel fuel. In this work, a series of caprolactam-based DESs were prepared using caprolactam as a hydrogen bond donor (HBD) and tetrabutylammonium halides as hydrogen bond acceptors (HBAs). By screening different halide anions and molar ratios of HBD and HBA, the DES tetrabutylammonium bromide/caprolactam (TBAB/CPL = 1:2) showed the highest desulfurization efficiency with the Nernst partition coefficient of 5.04, which was much higher than those of most metal-free DESs and ILs. The desulfurization efficiency could reach as high as 96.6% after a two-stage extraction. Finally, the extraction mechanism was investigated systematically using 1H nuclear magnetic resonance and Fourier transform infrared spectroscopies. Then, a density functional theory study suggested that hydrogen bonding and C–H···π interaction between DES and dibenzothiophene accounted for the higher desulfurization efficiency, enabling DES to effectively remove dibenzothiophene from the model fuels.

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Section: ■ Results and Discussionmentioning

confidence: 61%

Section: Results and Discussionmentioning

confidence: 70%

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Yin

Luo

et al. 2022

ACS Sustainable Chem. Eng.

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“…Before absorption of SO 2 , the peak at a wavelength of 3401.3 cm –1 denotes the N–H stretching vibration of the TBAB/CPL and the peaks at approximately 1635.4 cm –1 represent the CO stretching vibration. For the N–C–H stretching vibration in TBAB/CPL, the absorbance peak is found at 1477.2 cm –1 However, the characteristic peaks of TBAB/CPL are all changed or shifted after absorption of SO 2 .…”

Section: Resultsmentioning

confidence: 95%

“…For the N–C–H stretching vibration in TBAB/CPL, the absorbance peak is found at 1477.2 cm –1 However, the characteristic peaks of TBAB/CPL are all changed or shifted after absorption of SO 2 . The N–H stretching vibration of the TBAB/CPL shifts to 3216.7 cm –1 , the new CO stretching vibration appears at the peak of 1646.9 cm –1 , and a slight blue shift occurs for the N–C–H stretching vibration.…”

Section: Resultsmentioning

confidence: 95%

Role of Hydrophilic Ammonium-Based Deep Eutectic Solvents in SO₂ Absorption

et al. 2019

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Acid gases, especially sulfur dioxide (SO 2 ), released from the burning of fossil fuels, have made a great contribution to environmental pollution. However, the technologies to remove the acid gases have high operation costs and energy requirements. A kind of hydrophilic deep eutectic solvents (DESs) were synthesized and applied to solve the problem of SO 2 environmental pollution. The SO 2 absorption conditions were optimized including the kind of DESs, viscosity, and temperature. The hydrophilic interaction in SO 2 absorption was explored. The hydrophilic property of caprolactam/ tetrabutylammonium bromide DESs (TBAB/CPL) greatly reduced the gas transfer barrier, thus accreting the SO 2 absorption rate by enhancing the accessibility of the active sites on DESs and SO 2 . The surface tension decreased with the absorption of SO 2 , and the minimal surface tension of TBAB/CPL was 32 mN m −1 at 303.2 K (surface entropy, 0.0395 J K −1 m −2 ) when the concentration of TBAB/CPL aqueous solution was 2 mol L −1 . The phase-transfer process for the SO 2 absorption system was determined by nuclear magnetic resonance, Fourier transform infrared spectroscopy, and Raman spectroscopy. The mechanism of the hydrophilic absorption of SO 2 in TBAB/CPL DESs was also developed.

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“…Ren et al synthesized DES based on hydrophilic polyols such as L-arginine and glycerol for CO2 solubility to address this issue [66].…”

Section: Environmental Applicationsmentioning

confidence: 99%

Ionic liquids as alternative solvents for energy conservation and environmental engineering

2021

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Because of industrialization and modernization, phenomenal changes have taken place in almost all spheres of life. Consequently, the consumption of energy resources and the cases of environmental hazards have risen to an unprecedentedly high level. A development model with due consideration to nature and an efficient utilization of energy sources has become the need of the hour, in order to ensure a sustainable balance between the environmental and technological needs. Recent studies have identified the suitability of ionic liquids (ILs), often labeled as ‘green solvents’, in the efficient utilization of energy resources and activities such as bio-extraction, pollution control, CO2 capture, waste management etc. in an environmentally friendly manner. The advent of magnetic ionic liquids (MILs) and deep eutectic solvents (DESs) have opened possibilities for a circular economic approach in this filed. This review intends to analyze the environmental and energy wise consumption of a wide variety of ionic liquids and their potential towards future.

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Formation mechanisms of Caprolactam-tetraalkyl ammonium halide deep eutectic and its hydrate

Cited by 8 publications

References 36 publications

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Role of Hydrophilic Ammonium-Based Deep Eutectic Solvents in SO₂ Absorption

Ionic liquids as alternative solvents for energy conservation and environmental engineering

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Formation mechanisms of Caprolactam-tetraalkyl ammonium halide deep eutectic and its hydrate

Cited by 8 publications

References 36 publications

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Role of Hydrophilic Ammonium-Based Deep Eutectic Solvents in SO2 Absorption

Ionic liquids as alternative solvents for energy conservation and environmental engineering

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Role of Hydrophilic Ammonium-Based Deep Eutectic Solvents in SO₂ Absorption