Synthesis of propylene glycol ethers from propylene oxide catalyzed by environmentally friendly ionic liquids

Zhao, Caidan; Chen, Shengxin; Li, Zihang; Liu, Ruixia; Ren, Baozeng; Zhang, Suojiang

doi:10.1016/s1872-2067(17)62831-6

Cited by 17 publications

(11 citation statements)

References 41 publications

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“…Undesirably, the side-reaction of GO alcoholysis by polar solvents (such as H 2 O, CH 3 OH, ethanol, etc.) would be inevitable. , After basic anions (OH – , Ph – , and OPy – ) were serially introduced into PILs, the yields of DMC began to increase steadily, and the upward trend over different PILs was similar to that of CO 2 cycloaddition. Among them, the DMC yield of P-DAEImOH was only 17%, ascribing to the reaction of OH – with CO 2 to form stable weak-basic HCO 3 – and it was difficult to insert activated CO 2 into GO. , However, after introducing OPy – anions, P-DAEImOPy presented the highest DMC yield (50%) and the lowest byproduct yield (27%), indicating that the nucleophilic insertion ability of OPy – anions to CO 2 contributed to the rapid consumption of GO in the CO 2 cycloaddition reaction so as to slow down the alcoholysis of GO by CH 3 OH.…”

Section: Resultsmentioning

confidence: 94%

“…would be inevitable. 12,43 After basic anions (OH − , Ph − , and OPy − ) were serially introduced into PILs, the yields of DMC began to increase steadily, and the upward trend over different PILs was similar to that of CO 2 cycloaddition. Among them, the DMC yield of P-DAEImOH was only 17%, ascribing to the reaction of OH − with CO 2 to form stable weak-basic HCO 3…”

Section: ■ Results and Discussionmentioning

confidence: 97%

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Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate

et al. 2022

ACS Sustainable Chem. Eng.

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CO2, as an engaging C1 building block, shines brightly in green conversion; besides, its unique identity as an acidic molecule is worthy of further development. Here, a novel mode of CO2 utilization was explored to play a dual role in the one-pot pressure-swing synthesis of dimethyl carbonate (DMC) over 2-hydroxypyridine anion functionalized poly(ionic liquid)s (OPy-PILs), that is, CO2 could act as both a raw material of coupling reaction and an acidic inhibitor of side-reaction. Specifically, OPy-PILs, constructed by free radical copolymerization followed by ion exchange, were applied to the one-pot coupling reaction of CO2, epoxide, and CH3OH. As an efficient heterogeneous catalyst, OPy-PILs could cover basic sites with acidic CO2 during the insertion of activated CO2 into epoxide by intermediate [OPy-CO2 –] so as to reduce the yield of the epoxide alcoholysis side-reaction from 27 to 12%. Moreover, various comparative experiments fully exhibited the high activity and stability of OPy-PILs, and theoretical calculations convincingly explained the dual role-playing of CO2 in a one-pot pressure-swing reaction. This work paves a novel avenue for the deeper exploration of the CO2 utilization potential in the catalytic process.

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Section: Resultsmentioning

confidence: 94%

Section: ■ Results and Discussionmentioning

confidence: 97%

Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate

et al. 2022

ACS Sustainable Chem. Eng.

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“…The indicator in the form of bromothymol blue (BTB) was dissolved in methanol in a concentration of 1.6 × 10 −5 mol/dm 3 , whereas solutions of ionic liquids were prepared in a concentration of 0.01 mol/dm 3 . The highest absorbance of BTB in the unrotonated form was determined against 0.1 molar and 0.01 molar sodium hydroxide at a wavelength of 620 nm [ 14 ].…”

Section: Methodsmentioning

confidence: 99%

“…Additionally, they are characterized by quite good thermal stability, and it is possible to reuse them in subsequent reaction stages. Ionic liquids containing an imidazolium cation are used, inter alia, in in C–O bond opening reactions in epoxides, in alcohol etherification reactions with alkyl chloride in phase transfer catalysis (PTC), and in alcohol-alcohol etherification [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Moreover, the use of ammonium acetates in the etherification reactions of propylene oxide with alcohols leads to more selective products [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids as Homogeneous Catalysts for Glycerol Oligomerization

et al. 2022

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Ionic liquids (ILs) were used for the first time as catalysts for the glycerin condensation reaction. A series of imidazolium and ammonium ionic liquids differing in the length of the alkyl substituent (C2, C12, and C14) and the type of anion (Br−, CH3COO−, and NaHPO4−) were synthesized using a typical two-step method. The structure of the obtained ILs was confirmed by nuclear magnetic resonance 13C NMR, and their base power was determined on the basis of the Hammett function. The oligomerization of glycerin with the participation of the obtained ionic liquids and, for comparison, in the presence of a homogeneous basic catalyst Na2CO3, was carried out for 3 h at 180 °C, under a pressure of 0.4 bar, where the highest conversion, i.e., 92%, was obtained against 1-dodecyl-N, N, N-triethylammonium acetate. The course of the reaction was monitored using a reaction system coupled with a FTIR spectrometer, which allowed for the tracking of changes in product concentration over time and the assessment of glycerin oligomerization kinetics. The reaction products were analyzed by positive electrospray ionization mass spectrometry (ESI-MS), 13C NMR, and infrared absorption spectroscopy (FTIR).

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“…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%

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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Synthesis of propylene glycol ethers from propylene oxide catalyzed by environmentally friendly ionic liquids

Cited by 17 publications

References 41 publications

Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate

Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate

Ionic Liquids as Homogeneous Catalysts for Glycerol Oligomerization

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

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Synthesis of propylene glycol ethers from propylene oxide catalyzed by environmentally friendly ionic liquids

Cited by 17 publications

References 41 publications

Understanding the Ingenious Dual Role-Playing of CO2 in One-Pot Pressure-Swing Synthesis of Linear Carbonate

Understanding the Ingenious Dual Role-Playing of CO2 in One-Pot Pressure-Swing Synthesis of Linear Carbonate

Ionic Liquids as Homogeneous Catalysts for Glycerol Oligomerization

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

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Product

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Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate

Understanding the Ingenious Dual Role-Playing of CO₂ in One-Pot Pressure-Swing Synthesis of Linear Carbonate