Understanding of the interactions between azole-anion-based ionic liquids and 2-methyl-3-butyn-2-ol from the experimental perspective: the cage effect

Xue, Fu‐Shan; Tang, Xiaochen; Chen, Tingting; Xu, Yingjie; Liu, Xiang; Lu, Yueqing; Wang, Xüming; Qin, Dandan; Zhang, Lin

doi:10.1039/d2cp00474g

Cited by 3 publications

(1 citation statement)

References 83 publications

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“…Measurement methods and procedures for η, ρ, and u were described in our previous work . η, ρ, and u of pure [P 4442 ][1-MHy] were simultaneously measured with an Anton Paar DSA 5000 M density and sound velocity meter combined with an Anton Paar AMVn falling ball automated microviscometer.…”

Section: Methodsmentioning

confidence: 99%

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Chen

Zhang

2022

ACS Sustainable Chem. Eng.

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A novel basic anion-functionalized ionic liquid with a 1-methylhydantoin anion ([1-MHy]−) and [P4442]+ cation was synthesized for efficient CO2 capture and catalytic conversion of CO2 to quinazoline-2,4(1H,3H)-dione, and CO2 absorption and conversion mechanisms were investigated by NMR, FT-IR, and DFT calculations. CO2 absorption results show that the capture capacity of [P4442][1-MHy] at 303.15 K and 0.1 MPa is up to 1.58 molCO2/molIL, which is attributed to the multiple-site cooperative interactions between CO2 with N– and CO of [1-MHy]− originated from the electron conjugation effect, resulting in a decrease in the CO2 absorption enthalpy (−51.4 kJ/mol) and an increase in the activation of CO2. Moreover, the high yield of quinazoline-2,4(1H,3H)-dione obtained by using [P4442][1-MHy] to catalyze 2-aminobenzonitrile with atmospheric-pressure CO2 was 97% and is solvent- and metal-free. The reaction mechanism indicates that [1-MHy]− with the multiple-site cooperative interactions can not only activate CO2 but also can activate 2-aminobenzonitrile by forming two types of hydrogen bonds with −NH2 (N–H···N– and N–H···OC), thus ensuring the excellent catalytic performance of [P4442][1-MHy]. Furthermore, due to the similar basicity of [1-MHy]− to the quinazolide anion ([Quinazolide]−), it can effectively prevent the deprotonation of the acidic quinazoline-2,4-dione into [Quinazolide]−, thereby improving its yield. In addition, [P4442][1-MHy] has good recycling performance during CO2 capture and conversion. The physicochemical properties of [P4442][1-MHy] are also reported. The obtained results may provide a new strategy for converting CO2 into value-added chemicals under green conditions.

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Section: Methodsmentioning

confidence: 99%

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Chen

Zhang

2022

ACS Sustainable Chem. Eng.

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Insight into the Effect of Physicochemical Properties on CO2 Absorption Behavior of Imidazole Anion-Functionalized Ionic Liquids

Wang,

He,

Chen

et al. 2023

J Solution Chem

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Three imidazole anion-functionalized ionic liquids (IFILs) with tributylethylphosphonium ([P 4442 ] + ) cation and imidazolate ([Im] − ), 4-methylimidazolate ([4-MeIm] − ), or 4-bromimidazolate ([4-BrIm] − ) anions were prepared to study the effect of physicochemical properties on CO 2 absorption behavior. Density (ρ), viscosity (η), speed of sound (u) of the studied IFILs were measured, and molecular volume (V m ), standard entropy (S 0 ), lattice energy (U POT ), and isentropic compressibility coe cient (κ s ) were calculated accordingly. CO 2 absorption behavior of [P 4442 ][Im] at T = 313.15-333.15 K and p = 0.2 and 1 bar were investigated as an example. The results show that with the increase of temperature, ρ, η, u, and U POT decrease, while V m , S 0 , and κ s increase, due to a decrease in electrostatic interaction correspondingly. The orders of ρ, u, η, V m , and S 0 values are as follows:while U POT and κ s are in reverse order. Interestingly, CO 2 capture capacity of IFILs is approximately linear with η or κ s . Due to low η and high κ s , CO 2 absorption capacity of [P 4442 ][Im] is almost independent of temperature and partial pressure, as high as 0.90 mol CO 2 /mol IL at 333.15 K and 0.2 bar, indicating that [P 4442 ][Im] has potential applications for CO 2 absorption at high temperature and low pressure.

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Insight into the effect of physicochemical properties on CO2 absorption behavior of imidazole anion-functionalized ionic liquids

Wang

Chen

et al. 2023

Preprint

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Three imidazole anion-functionalized ionic liquids (IFILs) with tributylethylphosphonium ([P4442]+) cation and imidazolate ([Im]−), 4-methylimidazolate ([4-MeIm]−), or 4-bromimidazolate ([4-BrIm]−) anions were prepared to study the effect of physicochemical properties on CO2 absorption behavior. Density (ρ), viscosity (η), speed of sound (u) of the studied IFILs were measured, and molecular volume (Vm), standard entropy (S0), lattice energy (UPOT), and isentropic compressibility coefficient (κs) were calculated accordingly. CO2 absorption behavior of [P4442][Im] at T = 313.15-333.15 K and p = 0.2 and 1 bar were investigated as an example. The results show that with the increase of temperature, ρ, η, u, and UPOT decrease, while Vm, S0, and κs increase, due to a decrease in electrostatic interaction correspondingly. The orders of ρ, u, η, Vm, and S0 values are as follows: [P4442][Im] < [P4442][4-MeIm] < [P4442][4-BrIm], while UPOT and κs are in reverse order. Interestingly, CO2 capture capacity of IFILs is approximately linear with η or κs. Due to low η and high κs, CO2 absorption capacity of [P4442][Im] is almost independent of temperature and partial pressure, as high as 0.90 mol CO2/mol IL at 333.15 K and 0.2 bar, indicating that [P4442][Im] has potential applications for CO2 absorption at high temperature and low pressure.

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Understanding of the interactions between azole-anion-based ionic liquids and 2-methyl-3-butyn-2-ol from the experimental perspective: the cage effect

Abstract: The interactions between azole-anion-based ionic liquids (AILs) and 2-methyl-3-butyn-2-ol (MBY) play an important role in AILs-promoted carboxylative cyclization of MBY with CO2. To better understand the interactions between AILs ([P66614][Im],...

Cited by 3 publications

References 83 publications

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Insight into the Effect of Physicochemical Properties on CO2 Absorption Behavior of Imidazole Anion-Functionalized Ionic Liquids

Insight into the effect of physicochemical properties on CO2 absorption behavior of imidazole anion-functionalized ionic liquids

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Understanding of the interactions between azole-anion-based ionic liquids and 2-methyl-3-butyn-2-ol from the experimental perspective: the cage effect

Abstract: The interactions between azole-anion-based ionic liquids (AILs) and 2-methyl-3-butyn-2-ol (MBY) play an important role in AILs-promoted carboxylative cyclization of MBY with CO2. To better understand the interactions between AILs ([P66614][Im],...

Cited by 3 publications

References 83 publications

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO2 and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO2 and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Insight into the Effect of Physicochemical Properties on CO2 Absorption Behavior of Imidazole Anion-Functionalized Ionic Liquids

Insight into the effect of physicochemical properties on CO2 absorption behavior of imidazole anion-functionalized ionic liquids

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Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions

Efficient Synthesis of Quinazoline-2,4(1H,3H)-dione via Simultaneous Activated CO₂ and 2-Aminobenzonitrile by 1-Methylhydantoin Anion-Functionalized Ionic Liquid through the Multiple-Site Cooperative Interactions