Aromatic sulfonation XIII determination of the kinetic isotope effect of hydrogen in the sulfonation and sulfonylation of benzene

Technical Universlty B mV e s h k a 230,637 1 1 Bmo Czech RepublicThis paper reviews the various reactions used to sulfonate polymers, especially polystyrene. The mechanisms for the sulfonation of low molar mass compounds are also 13scussed. The commonly used sulfonation reagents are described, with an emphasis on SO, and its physical and chemical properties. Polymer sulfonations can be grouped into two general routes: one involving homogeneous sulfonation and t h e other heterogeneous reactions.

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Homogeneous and heterogeneous sulfonation of polymers: A review

Kučera

Jančář

1998

Polymer Engineering & Sci

160

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Kinetics of the isomerization of toluenesulfonic acids in aqueous sulfuric acid

Wanders

Cerfontain

Kort

1967

Recl. Trav. Chim. Pays‐Bas

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The kinetics of the isomerization of the three isomeric toluenesulfonic acids have been studied at 140" in 68.7 and 74.0 wt-% sulfuric acid.The isomer distribution in the sulfonation of toluene at this temperature and acid concentrations, has also been determined. The equilibrium mixtures contain mainly the meta-and para-and only small amounts of orrho-isomer.The experimentally determined pseudo first-order isomerization rate constants compare satisfactorily with the rate constants calculated from desulfonation rate constants and d f o n a t i o n isomer distribution data. This result is discussed in terms of an intermolecular isomerization mechanism. IntroductionIn connection with our study on the desulfonation of the three isomeric toluenesulfonic acids 1, it was thought interesting to investigate the isomerization of these acids. To allow correlation of the isomerization studies with the desulfonation rate data, the isomer distribution for the sulfonation of toluene under the conditions of the desulfonation and isomerization studies was determined as well.The isomerization of the toluenesulfonic acids in aqueous sulfuric acid was studied by HolltBman and Caland and by Muramoto 3 . They reported that 0-and p-toluenesulfonic acids are interconverted during isomerization and that m-toluenesulfonic acid does not isomerize at all. Recently, Spryskov4 published quite different results which prompted us to give a preliminary account of our kinetic studies 5 . Both groups of investigators 495 observed

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Aromatic sulfonation 20: The sulfonation of some chlorobenzenes with sulfur trioxide in nitromethane as solvent

Bosscher

Cerfontain

1968

Recl. Trav. Chim. Pays‐Bas

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The sulfonation of chlorobenzene and p-dichlorobenzene with sulfur trioxide in nitromethane as solvent has been studied. The main reaction products are arenesulfonic anhydride and probably arenepyrosulfonic acid. With p-dichlorobenzene as substrate the amount of diary1 sulfone is undetectably small; with chlorobenzene it is < 1-mole % relative to the converted substrate. The sulfonation is of the first order with respect to the substrate and of the second order with respect to sulfur trioxide. For each mole of converted substrate two moles of sulfur trioxide are consumed. The sulfonation of p-dichlorobenzene proceeds without a primary kinetic isotope effect of hydrogen.It is suggested that the sulfonation proceeds via 1-arenonium-1-sulfonate and 1-arenonium-1-pyrosulfonate as the subsequent reactive intermediates, with the formation of the latter intermediate as the ratelimiting step. The kinetics of the formation of 4,4'-dichlorodiphenyl sulfone are compatible with a mechanism in which the species p-CIC~H&OgH is the effective sulfonylating entity. The literature on aromatic sulfonation with sulfur trioxide in aprotic solvents is critically reviewed.Extensive mechanistic studies on aromatic sulfonation have been performed with aqueous and fuming sulfuric acid as the reagent 2 . At the outset of this investigation, the number of kinetic studies pertaining to sulfur trioxide as reagent was, however, rather limited 3-8. It was therefore thought interesting to study the kinetics of aromatic sulfonation with this * Preceding paper: Rec. Trav. Chim. 87, 24 (1968).

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Aromatic sulfonation XIII determination of the kinetic isotope effect of hydrogen in the sulfonation and sulfonylation of benzene

Cited by 9 publications

References 6 publications

Homogeneous and heterogeneous sulfonation of polymers: A review

Homogeneous and heterogeneous sulfonation of polymers: A review

Kinetics of the isomerization of toluenesulfonic acids in aqueous sulfuric acid

Aromatic sulfonation 20: The sulfonation of some chlorobenzenes with sulfur trioxide in nitromethane as solvent

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