Clean-Chemistry Sulfonation of Aromatics

Corby, Brian W.; Gray, Anthony D.; Meaney, Padraig J.; Falvey, Michael J.; Lawrence, Gregory P.; Smyth, Timothy P.

doi:10.3184/030823402103172329

Cited by 13 publications

(14 citation statements)

References 7 publications

(3 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Trifluoroacetyl sulfate was prepared according to previously published procedures. , Trifluoroacetic anhydride (3.8 mL, 0.027 mol) was added to a nitrogen-purged round-bottom flask. The flask was cooled in an ice bath for 15 min, and then concentrated sulfuric acid (1 mL, 0.018 mol) was added.…”

Section: Methodsmentioning

confidence: 99%

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

et al. 2018

View full text Add to dashboard Cite

Blocky sulfonated poly(ether ether ketone) (SPEEK) ionomers were synthesized by postpolymerization functionalization in the gel state. Matched sets of blocky and random SPEEK with ion contents between 3 and 11 mol % were prepared, and the thermal transitions and crystallization kinetics were examined using differential scanning calorimetry (DSC). At similar ion contents, the blocky SPEEK exhibited higher crystallizability and faster crystallization kinetics than random SPEEK. Reduced scattering contrast in the USAXS/ SAXS/WAXD analysis of the blocky SPEEK copolymer membranes, relative to the random analogues, suggested that the ionic aggregates in blocky SPEEK were distributed in close proximity to the crystalline domains. Despite similar water uptake values for the low ion content random and blocky SPEEK membranes, the blocky SPEEK exhibited higher proton conductivities than their random analogues. At significantly higher ion contents (45 mol %), the blocky SPEEK membranes remained semicrystalline, showed controlled water uptake, and exhibited a 2.5 times higher conductivity over that of the amorphous, random analogues. Moreover, these new blocky, semicrystalline SPEEK membranes were found to exhibit a proton conductivity that was comparable to that of the benchmark 1100 EW Nafion.

show abstract

Section: Methodsmentioning

confidence: 99%

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Other literature results in the batch mode were also summarized in Table 3 (entries 1-3). [32][33][34] Entry 1…”

Section: Comparison With the Batch Modementioning

confidence: 99%

“…Other literature results in the batch mode were also summarized in Table 3 (entries 1-3). [32][33][34] Entry 1 shows that only 50% yield was achieved in a long reaction time of 72 h. In addition, 2.l mol trifluoroacetic anhydride (TFFA) should be used as a catalyst per mol NB. Entry 2 demonstrates that an excellent yield of 98% was obtained at room temperature, but much more dichloroethane was used as a solvent, and the total ratio of (SO 3 + H 2 SO 4 ) to NB was as high as two.…”

Section: Comparison With the Batch Modementioning

confidence: 99%

A simple and efficient synthesis protocol for sulfonation of nitrobenzene under solvent-free conditions via a microreactor

Chen

Jiao

et al. 2012

RSC Adv.

View full text Add to dashboard Cite

A simple and efficient method for the sulfonation of nitrobenzene using SO 3 as the sulfonating agent in a microreactor was developed and conducted in this work. The reaction enthalpy was determined using a microreactor-based calorimeter. The effects of molar ratio of reactants, reaction temperature and liquid hourly space velocity (LHSV) on the reaction performance were experimentally studied under solvent-free conditions. Under optimized reaction conditions, 94% conversion of nitrobenzene (NB) and 88% yield of meta-nitrobenzenesulfonic acid (m-NBSA) was obtained even when the residence time was less than 2 s. A microreactor-batch set-up was fabricated and developed to completely convert NB. The process safety has been improved and reaction time has been reduced compared to the batch method. These results demonstrate that the multifunctional integrated microreactor is an extremely useful and highly efficient tool for the sulfonation of NB under solvent-free conditions.

show abstract

“…The sulfonation of aromatic compounds is of significant importance in both industry and academia. [1][2][3] Traditional methods for the synthesis of aromatic sulfonic acids involve the sulfonylation of aromatic compounds with sulfonating agents such as concentrated sulfuric acid, 4 trifluoroacetic acid-sulfuric acid, 5 sulfur trioxide in dichloromethane, 6 silica-sulfuric acid, 7 the sulfur trioxide-dioxane complex, 8 oleum, 9 sulfur trioxide in nitrobenzene, 10 and 1,3-disulfo-1H-imidazol-3-ium chloride in aqueous media. 11 Other alternative methods include the sulfonation of Grignard and lithium reagents, 12 the Vilsmeier-Haack reaction in acetonitrile, 13 destructive oxidation of aryl thioglycolate esters, 14 and oxidation of thiols and disulfides using HOF•MeCN.…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical sulfonation of aromatic compounds using NaHSO₄·H₂O/P₂O₅

Zuo

Qin

Zhang

et al. 2021

Journal of Chemical Research

View full text Add to dashboard Cite

show abstract

Clean-Chemistry Sulfonation of Aromatics

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 13 publications

References 7 publications

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

A simple and efficient synthesis protocol for sulfonation of nitrobenzene under solvent-free conditions via a microreactor

Mechanochemical sulfonation of aromatic compounds using NaHSO₄·H₂O/P₂O₅

Contact Info

Product

Resources

About

Clean-Chemistry Sulfonation of Aromatics

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 13 publications

References 7 publications

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

Blocky Ionomers via Sulfonation of Poly(ether ether ketone) in the Semicrystalline Gel State

A simple and efficient synthesis protocol for sulfonation of nitrobenzene under solvent-free conditions via a microreactor

Mechanochemical sulfonation of aromatic compounds using NaHSO4·H2O/P2O5

Contact Info

Product

Resources

About

Mechanochemical sulfonation of aromatic compounds using NaHSO₄·H₂O/P₂O₅