Synthesis of glycerol carbonate from glycerol and dimethyl carbonate over DABCO embedded porous organic polymer as a bifunctional and robust catalyst

Wan, Yali; Lei, Yizhu; Lan, Guosong; Liu, Dingfu; Li, Guangxing; Bai, Ruke

doi:10.1016/j.apcata.2018.06.022

Cited by 41 publications

(26 citation statements)

References 52 publications

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“…As depicted in Figure , the band at 174.8 ppm was assigned to the amide groups of the polymer. The bands at 126.8–144.5 ppm can be attributed to the aromatic carbons of the polymers. The peak at 110.9 ppm corresponds to a small amount of unpolymerized vinyl groups.…”

Section: Resultsmentioning

confidence: 75%

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Copper supported on phenanthroline‐functionalized porous polymer as an active catalyst for the oxidative carbonylation of methanol

Lei

Leng

et al. 2019

Applied Organom Chemis

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Porous organic polymer has recently attracted tremendous interest because of its potential to combine the best features of homogeneous and heterogeneous catalysts. In this study, copper supported on phenanthroline‐functionalized porous polymer (Cu@PCP‐Phen) was prepared by a co‐polymerization method and used as a heterogeneous catalyst for dimethyl carbonate synthesis via the oxidative carbonylation of methanol. The catalyst was characterized by N2 adsorption, scanning electron microscopy, transmission electron microscopy, 13C solid‐state nuclear magnetic resonance, and X‐ray photoelectron spectroscopy, which suggested that it possessed a big surface area, hierarchical porous structure, and strong electron‐donating effect toward copper species. The Cu@PCP‐Phen catalyst showed high catalytic activity, which was significantly higher than those achieved with Cu‐based catalysts under similar reaction conditions. In addition, the catalyst can be easily separated and reused at least six times with only a slight decrease in activity. The salient features of this protocol are the simplicity in handling of the catalyst, high catalytic activity, excellent selectivity, low copper leaching, and good catalyst recyclability.

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Section: Resultsmentioning

confidence: 75%

“…The peak at 110.9 ppm corresponds to a small amount of unpolymerized vinyl groups. The peaks observed at 40.3 ppm can be attributed to the polymerized vinyl groups . These observations indicated the successful synthesis of the co‐polymer.…”

Section: Resultsmentioning

confidence: 82%

Copper supported on phenanthroline‐functionalized porous polymer as an active catalyst for the oxidative carbonylation of methanol

Lei

Leng

et al. 2019

Applied Organom Chemis

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“…The signal at around 130.7 ppm associated with the aromatic carbons could be observed [40,43]. The peak at 43.5 ppm associated with the polymerized vinyl groups could also be observed [40,43]. The solid-state 31 P NMR spectrum of P(QPOTf-BSA)-0.5 displayed a single peak at around 21 ppm, as shown in Figure S1 from Supplementary Materials.…”

Section: Characterizationmentioning

confidence: 93%

“…Figure 4 showed the 13 C solid-state NMR spectrum of a representative sample of P(QPOTf-BSA)-0.5. The signal at around 130.7 ppm associated with the aromatic carbons could be observed [40,43]. The peak at 43.5 ppm associated with the polymerized vinyl groups could also be observed [40,43].…”

Section: Characterizationmentioning

confidence: 95%

A Porous Polymer-Based Solid Acid Catalyst with Excellent Amphiphilicity: An Active and Environmentally Friendly Catalyst for the Hydration of Alkynes

Lei

Zhang

et al. 2019

Polymers

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Developing efficient solid acid catalysts for aqueous organic reactions is of great importance for the development of sustainable chemistry. In this work, a porous polymeric acid catalyst was synthesized via a solvothermal copolymerization and a successive ion-exchange method. Physicochemical characterizations suggested that the prepared polymers possessed large Brunauer-Emmett-Teller (BET) surface areas, a hierarchically porous structure, excellent surface amphiphilicity, and nice swelling properties. Notably, an activity test in phenylacetylene hydration indicated that the prepared solid acid exhibited high catalytic activity in water, which outperformed commercial amberlyst-15, sulfuric acid, and benzenesulfonic acid. Moreover, the prepared solid acid can be easily recovered and reused at least four times. Additionally, a variety of aromatic and aliphatic alkynes could be effectively transformed into corresponding ketones under optimal reaction conditions. Porous organic polymers (POPs), which feature designable chemical functionalities and large surface areas, have recently received great research interest in the field of catalysis, due to their potential to combine the advantages of heterogeneous and homogeneous catalysis [22][23][24][25]. To date, a considerable number of porous polymeric acids have been successfully developed for various acid-catalyzed reactions [26][27][28]. Generally, for solid catalysts in water, the catalysts should be designed to be amphiphilic, thus allowing the nice contact between organic substrates, water, and the solid catalyst [29][30][31]. However, most porous polymeric acids are mainly composed of aromatic frameworks, endowing the catalyst with hydrophobic surface wettability [26,27,32], and thus, restricting their catalytic applications in water. Porous ionic polymers (PiPs) [33,34], which represent a new kind of porous organic polymer (POP) [33][34][35], could be easily prepared from the free radical polymerization of vinyl-functionalized organic salts. When used as the catalytic supports, PiPs can exhibit not only the features of POPs, but also some additional advantages, such as allowing easy functionalization via ion-exchange reactions and easy adjustment of surface wettability of the polymer [35][36][37][38].To develop an efficient and solid acid catalyst for the hydration of alkynes in water, herein, we initiate the synthesis of amphiphilic porous polymeric acids containing both the sulfonic and phosphonium salt groups (P(QPOTf-BSA)) and study their catalytic performances in water-mediated alkyne hydration. The amphiphilic and hyper-cross-linked P(QPOTf-BSA) was facilely synthesized through the free-radical copolymerization of 4-vinylbenzyl-tris-(4-vinylphenyl)-phosphonium chloride (QP) and sodium p-styrene sulfonate, followed by ion-exchange with HSO 3 CF 3 , as shown in Scheme 1. An activity test in phenylacetylene hydration suggested that the obtained P(QPOTf-BSA) exhibited excellent activity, outperforming the activities of heterogeneous amberlyst-15, as well as hom...

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“…To continue our ongoing efforts for exploring highly efficient heterogeneous catalysts for carbonylation reactions, herein, we reported palladium supported on phosphorus‐doped porous organic polymer (Pd@POP‐Ph 3 P) as an efficient, stable and recyclable catalyst for carbonylative Suzuki coupling and alkoxycarbonylation of aryl iodides and bromides.…”

Section: Introductionmentioning

confidence: 99%

Carbonylative Suzuki coupling and alkoxycarbonylation of aryl halides using palladium supported on phosphorus‐doped porous organic polymer as an active and robust catalyst

Wan

Song

et al. 2018

Applied Organom Chemis

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Developing highly active catalysts with the combined advantages of molecular and solid catalysis is considered as the “Holy Grail” in the area of catalysis research. Herein, a phosphorus‐doped porous polymer‐immobilized palladium was successfully developed as an efficient, robust, and recyclable catalyst for the carbonylative Suzuki coupling and alkoxycarbonylation reactions of aryl halides. Rather than just as an immobilizing molecular catalyst, palladium supported on phosphorus‐doped porous organic polymer exhibits even better catalytic performances than that of its analogue homogeneous catalysts in both carbonylation reactions. Moreover, the catalyst can be easily separated and reused for at least 5 times without significant loss in reactivity. Importantly, the catalyst was highly stable under carbonylation reaction conditions, and no palladium nanoparticle was observed even after the 5th reuse.

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Synthesis of glycerol carbonate from glycerol and dimethyl carbonate over DABCO embedded porous organic polymer as a bifunctional and robust catalyst

Cited by 41 publications

References 52 publications

Copper supported on phenanthroline‐functionalized porous polymer as an active catalyst for the oxidative carbonylation of methanol

Copper supported on phenanthroline‐functionalized porous polymer as an active catalyst for the oxidative carbonylation of methanol

A Porous Polymer-Based Solid Acid Catalyst with Excellent Amphiphilicity: An Active and Environmentally Friendly Catalyst for the Hydration of Alkynes

Carbonylative Suzuki coupling and alkoxycarbonylation of aryl halides using palladium supported on phosphorus‐doped porous organic polymer as an active and robust catalyst

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