Relationship of basicity and hydrogen bond properties of ionic liquids with its catalytic performance: Application to synthesis of propylene glycol methyl ether

Chen, Shengxin; Liu, Ruixia; Li, Yajing; Zhang, Ruirui; Zhao, Caidan; Tang, Hongguo; Qiao, Congzhen; Zhang, Suojiag

doi:10.1016/j.catcom.2017.03.018

Cited by 17 publications

(6 citation statements)

References 27 publications

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“…To explore the influence of "ionpair" of ILs dissociated to cation and anion in methanol, the pK a(IL) of ILs and solvation free energies (ΔG sol ) of ILs have been predicted and calculated by DFT followed a thermodynamic cycle, 21 and the Hammett basicity (H 0 ) are measured by UV−visible spectrum with an indicator. 14 3.2. Solvent Parameters of Reaction System.…”

Section: Methodsmentioning

confidence: 99%

“…The basic strength of catalysts was evaluated from the measurement of Hammett function by a UV–visible spectroscopy method following previous work. , The typical process is the samples were prepared by mixing catalysts (0.01 mol/L) and BTB (ca. 2 × 10 –5 mol/L) with CH 3 OH.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous work, we explored the relationship between multifactors such as the Hammett basicity (H 0 ), HBD ability(α), HBA ability(β), and dipolarity/polarizability effect(π*) and catalytic performance in the coupling reaction of propylene oxide (PO) and methanol to PGME. 14 It was found that dissociation of ion pair could make a solute-solution effect to change the polarity parameters α, β, and π*, 15 which these parameters are regarded as key factors in many reactions. However, the quantitative relationships between the catalytic performance and these properties have rarely been reported.…”

Section: Introductionmentioning

confidence: 99%

“…However, it is not reasonable to considered single factor in reactions, because different properties of ILs sometimes have synergetic effect on catalysis. In our previous work, we explored the relationship between multifactors such as the Hammett basicity ( H 0 ), HBD ability(α), HBA ability(β), and dipolarity/polarizability effect(π*) and catalytic performance in the coupling reaction of propylene oxide (PO) and methanol to PGME . It was found that dissociation of ion pair could make a solute-solution effect to change the polarity parameters α, β, and π*, which these parameters are regarded as key factors in many reactions.…”

Section: Introductionmentioning

confidence: 99%

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Quantitative Control Factors of Double Salt Ionic Liquids Catalysis in the Coupling Reaction of Epoxied and Methanol

Chen

An²,

et al. 2021

Ind. Eng. Chem. Res.

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In recent years, multi-ionic liquids (ILs) mixture systems have been widely noticed and applied in catalysis due to their unique properties. In order to establish the quantitative relationship between parameters and catalytic behavior, double salt ILs (DSILs), with different cation (1-ethyl-3-methylimidazolium, choline, tetraethylammonium) but same anion (acetate), are performed in the coupling reaction of propylene oxide (PO) with methanol. In the present work, the DSILs properties like Hammett basicity (H 0), hydrogen bond donor (HBD) ability (α), hydrogen bond acceptor (HBA) ability (β) and dipolarity/polarizability effect (π*) were considered in the reaction. These control factors were quantitative related to catalytic performance by a modified liner solvent energy relationship (LSER) function that adding a Hammett function correction term. According to the modified-LSER, solvents with different parameters were tested to verify its validity and control the reaction. This study demonstrated each parameter could make a different contribution to chemical reaction. It provides a new perspective way for multi-ILs mixture avoiding the intricacies of the parameter relation in ILs catalysis reasonably.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Quantitative Control Factors of Double Salt Ionic Liquids Catalysis in the Coupling Reaction of Epoxied and Methanol

Chen

An²,

et al. 2021

Ind. Eng. Chem. Res.

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“…Changes in IL physical properties such as viscosity, hydrophobicity and polarity have been accomplished by altering the length of the alkyl groups on the rings (4,5). More recently, some other heterocyclic molecules with functional side chains were used in the preparation of ionic liquids, and many functional ILs were synthesized and utilized as catalysts for different reactions (6), the study of structure-property relationship of functional ionic liquid and their basic properties have aroused renewed interest (7,8).…”

Section: Introductionmentioning

confidence: 99%

Novel DBU-based hydroxyl ionic liquid for efficient Knoevenagel reaction in water

Zhao

Meng

Wei

et al. 2019

Green Chemistry Letters and Reviews

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Novel ionic liquid N-(2-hydroxy-ethyl)-DBU bromide ([HyEtDBU]Br), based on 1,8-diazabicyclo (5.4.0)undec-7-ene (DBU) and 2-bromoethanol, was introduced as catalyst for Knoevenagel condensation. Comparing with other non-hydroxyl ionic liquids, [HyEtDBU]Br showed a better catalytic activity, the hydroxyl group linked on the ionic liquid played an important role in facilitating the Knoevenagel condensation reaction. In the presence of [HyEtDBU]Br-H 2 O-DABCO composite system, the corresponding Knoevenagel adducts were obtained in good to excellent yields within short times in all cases examined, the procedure is simple and the desired products could be easily separated and purified without any requirement of column chromatographic purification. The use of water as the reaction medium makes the process environmentally benign. The composite system [HyEtDBU]Br-H 2 O can be recycled eight times without activity loss.

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Synthesis of Cyclic Carbonate Catalyzed by DBU Derived Basic Ionic Liquids

Cheng

Xia

et al. 2018

Chin. J. Chem.

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In this work, 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), 1,5‐diazabicyclo[4.3.0]‐5‐nonene (DBN), and imidazole (MIM)‐derived bromide ionic liquids (ILs) were synthesized and used to catalyze the cycloaddition reactions of carbon dioxide (CO2) with several kinds of epoxides to form cyclic carbonates. The DBU derived bromide ionic liquid system was found to have the best catalytic activity among all the tested ILs. The influences of reaction conditions (including temperature, pressure and reaction time) on the reaction of CO2 to propylene oxide (PO) were studied to show the best conditions of 120 °C, 1 MPa, 2.5 h catalyzed by 2 mol% DBU‐derived bromide ionic liquid, with the conversion of PO and the selectivity of propylene carbonate (PC) reaching 99% and 99%, respectively. Under the optimum reaction conditions, the ionic liquid system could be reused at least five times without decrease in selectivity and conversion. NMR spectroscopy and DFT calculations were used to reveal the hydrogen‐bond interaction between ionic liquids and reagent, based on which the reaction mechanism was proposed.

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Relationship of basicity and hydrogen bond properties of ionic liquids with its catalytic performance: Application to synthesis of propylene glycol methyl ether

Cited by 17 publications

References 27 publications

Quantitative Control Factors of Double Salt Ionic Liquids Catalysis in the Coupling Reaction of Epoxied and Methanol

Quantitative Control Factors of Double Salt Ionic Liquids Catalysis in the Coupling Reaction of Epoxied and Methanol

Novel DBU-based hydroxyl ionic liquid for efficient Knoevenagel reaction in water

Synthesis of Cyclic Carbonate Catalyzed by DBU Derived Basic Ionic Liquids

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