A new chloromethylation method based on polystyrene–divinylbenzene

Fu, Yuli; Huang, Xiaobei; Zhong, Shihua; Yi, Wen-Jun; Li, Lijun

doi:10.1007/s11696-019-00761-6

Cited by 20 publications

(7 citation statements)

References 16 publications

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“…The strong characteristic peaks between 3000 and 2800 cm –1 correspond to the C–H stretching vibrations, indicating that alkyl groups from DCM act as a cross-linker to bridge the aromatic monomers and produce highly cross-linked networks. The adsorption peak at 1260 cm –1 is assigned to the −CH 2 Cl vibration and the stretching bond observed at around 700 cm –1 is identified as the stretching vibration peak of C–Cl. , But the stronger peak at around 700 cm –1 in HCP-TPM is possibly attributed to the C–H out-plane bending vibration of some monosubstituted benzene. , The residual Cl contents in final polymers were found to be 1.99–3.93 wt %. The residual Cl atoms are mainly related to the fast reaction rate, which leads to premature precipitation of the polymer and hinders the further conversion of C–Cl in the polymer via the Friedel–Crafts alkylation reaction .…”

Section: Resultsmentioning

confidence: 97%

“…42,43 But the stronger peak at around 700 cm −1 in HCP-TPM is possibly attributed to the C−H out-plane bending vibration of some monosubstituted benzene. 44,45 The residual Cl contents in final polymers were found to be 1.99−3.93 wt %. The residual Cl atoms are mainly related to the fast reaction rate, which leads to premature precipitation of the polymer and hinders the further conversion of C−Cl in the polymer via the Friedel−Crafts alkylation reaction.…”

Section: ■ Introductionmentioning

confidence: 98%

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Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

2023

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Exploring the effect of the structural rigidity of selected building blocks on the resultant porosity of the desired polymers is crucial for the bottom-up design of hyper-cross-linked polymers. Herein, several novel polymers, based on two series building blocks with stepwise fine-tuned rigidity, were constructed by the low-cost solvent knitting method. Significantly, the porosity of these polymers is highly consistent with the structural rigidity of the basic building blocks, dramatically enhanced from a poor porous state to a micropore-rich framework, with an increase in BET surface areas from 248 to 1276 m2 g–1 for the HCPs based on monomers containing double benzene rings and from 37 to 2368 m2 g–1 for tetraphenyl-like monomer-based HCPs. The best performances, especially concerning methane adsorption capacity, are reached for the rigid 9,9′-spirobifluorene (SBF)-based HCP-SBF framework and flexible tetraphenylmethane (TPM)-based HCP-TPM, showing a 5–100 bar working capacity of 206 cm3 (STP: 273 K, 1 atm) cm–3 (0.296 g g–1) and 199 cm3 (STP) cm–3 (0.112 g g–1) at 273 K, respectively. The bottom-up-designed HCPs with engineered porosity are expected to become novel candidates for onboard methane storage.

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Section: Resultsmentioning

confidence: 97%

Section: ■ Introductionmentioning

confidence: 98%

Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

2023

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“…Figure 1 gave the result that the C Cl stretching of HCPS, with the frequencies at 1265 and 670 cm À1 , respectively, was significantly weakened. 23,24 These data indicated that the benzyl chloride of CMPS was consumed in the Friedel-Crafts alkylation. After the sulfur hydration process, the chlorine content was reduced to 0.79 and 1.41 mmolÁg À1 for EDT-HCPS and TMPMP-HCPS, respectively.…”

Section: Characterization Of the Sulfhydrylfunctionalized Polymersmentioning

confidence: 99%

Synthesis of sulfhydryl‐functionalized polymers for the efficient adsorption of Pd²⁺ and Ag⁺ from aqueous solution

Fu,

Duan,

Chen

et al. 2023

Journal of Polymer Science

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Herein, two sulfhydryl‐functionalized polymers, namely, EDT‐HCPS and TMPMP‐HCPS, were synthesized according to the Friedel‐Craft s alkylation and nucleophilic substitution, and they were used to adsorb Pd2+ and Ag+ from aqueous solution. The Friedel‐Crafts alkylation offered the polymers with hyper‐cross‐linking frameworks composed of plentiful rigid methylene. The nucleophilic substitution brought abundant functional SH groups (the sulfur contents were 12.6 and 9.4 wt%, respectively) to the polymers. The adsorption results showed that the capacities of Pd2+ and Ag+ on EDT‐HCPS were larger than TMPMP‐HCPS, and the higher quantities of functional SH groups and the porosity played a beneficial role. The equilibrium data can be characterized by the Langmuir model, and the maximum capacities of Pd2+ and Ag+ on EDT‐HCPS at 308 K were predicted to be 383.92 and 212.93 mg g−1, respectively. The produced polymers represented superior adsorption selectivity, reproducibility, and reusability, demonstrating their excellent performance for the adsorption of Pd2+ and Ag+, and analysis of the adsorption mechanism demonstrated that the SH groups played a major role due to the strong chemical complexation of the functional SH with Pd2+/Ag+.

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“…After the preparation of HCP pitch , it was then modified with chloromethylation. We used allyl chloride as the chlorine source and concentrated sulfuric acid as the catalyst which not only avoided the use of hydrochloric acid generators in the traditional chloromethylation [24,25] but also obtained a higher chlorine content. The effects of adding the catalyst and allyl chloride and the reaction temperature and reaction time on the changes of the specific surface area and the chlorine content of the carrier were also investigated.…”

Section: Influence Of Chloromethylation Parameters On Chlorine Contenmentioning

confidence: 99%

Preparation of Chloromethylated Pitch–Based Hyper–Crosslinked Polymers and An Immobilized Acidic Ionic Liquid as A Catalyst for the Synthesis of Biodiesel

et al. 2019

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Hyper-crosslinking polymers and its immobilized acid ionic liquid catalyst were prepared using cheap pitch, as a monomer, through hyper-crosslinking reactions and allyl chloride, as a chlorine source, for chloromethylation and further grafting with imidazole and functionalizing with sulfonic acid. The polymers were characterized by FE-SEM, FTIR, TG, and nitrogen sorption. The grafting ratios of the chloromethylated pitch-based hyper-crosslinked polymer (HCPpitch–CH2–Cl) and immobilized acid ionic liquid [HCPpitch–Im–Pros][Tos] were 3.5 mmol/g and 3.0 mmol/g, and the BET specific surface areas were 520 m2/g and 380 m2/g, respectively. This strategy provides an easy approach to preparing highly stable and acid functionalized mesoporous catalysts. The immobilized acidic ionic liquid was used as a catalyst for the esterification of oleic acid and methanol to synthesize biodiesel. The results demonstrated that under the optimal conditions of an alcohol to acid molar ratio of 7:1, ionic liquid to oleic acid molar ratio of 0.12, and a reaction time of 3 h at atmospheric pressure, the yield of methyl oleate can reach up to 93%. Moreover, the catalyst was reused five times without the yield decreasing significantly. This study shows that [HCPpitch–Im–Pros][Tos] is a robust catalyst for the synthesis of biodiesel.

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A new chloromethylation method based on polystyrene–divinylbenzene

Cited by 20 publications

References 16 publications

Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

Synthesis of sulfhydryl‐functionalized polymers for the efficient adsorption of Pd²⁺ and Ag⁺ from aqueous solution

Preparation of Chloromethylated Pitch–Based Hyper–Crosslinked Polymers and An Immobilized Acidic Ionic Liquid as A Catalyst for the Synthesis of Biodiesel

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A new chloromethylation method based on polystyrene–divinylbenzene

Cited by 20 publications

References 16 publications

Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

Porosity Engineering of Hyper-Cross-Linked Polymers Based on Fine-Tuned Rigidity in Building Blocks and High-Pressure Methane Storage Applications

Synthesis of sulfhydryl‐functionalized polymers for the efficient adsorption of Pd2+ and Ag+ from aqueous solution

Preparation of Chloromethylated Pitch–Based Hyper–Crosslinked Polymers and An Immobilized Acidic Ionic Liquid as A Catalyst for the Synthesis of Biodiesel

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Synthesis of sulfhydryl‐functionalized polymers for the efficient adsorption of Pd²⁺ and Ag⁺ from aqueous solution