88-20-0

Usage

Uses

Used in Natural Gas Hydrate Promotion:
2-TOLUENESULFONIC ACID is used as an additive in the promotion of natural gas hydrate formation. It enhances the stability and formation of natural gas hydrates, which are ice-like structures that form when natural gas is exposed to high pressure and low temperature conditions. This property makes it useful in the transportation and storage of natural gas, as well as in the exploration and production of hydrocarbon resources.

InChI:InChI=1/C7H8O3S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3,(H,8,9,10)

Upstream product

• 64-17-5 ethanol 
• 17333-74-3 2-methylbenzene diazonium 
• 56919-17-6 4-bromo-toluene-2-sulfonic acid 
• 13165-77-0 toluenesulfinic acid 
• 615-37-2 ortho-methylphenyl iodide 
• 54437-71-7 N-methyl-N-phenyl-2-methylbenzenesulfonamide 
• 104-15-4 toluene-4-sulfonic acid 
• 7664-93-9 sulfuric acid 
• 108-88-3 toluene 
• 7446-11-9 sulfur trioxide 
• 108-24-7 acetic anhydride 
• 7790-94-5 chlorosulfonic acid 
• 118-88-7 4-amino-toluene-2-sulfonic acid 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 

Downstream Products

• 23959-97-9 bis(cyclohexyl) dithiodiglycolate 
• 91-63-4 2-methylquinoline 
• 507-70-0 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol 
• 98-55-5 terpineol 
• 104-15-4 toluene-4-sulfonic acid 
• 95-48-7 ortho-cresol 
• 65-85-0 benzoic acid 
• 69-72-7 salicylic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 498-24-8 Mesaconic acid 
• 131505-71-0 4-cyclobutyl-1-(4-ethynylphenyl)-2,6-dioxa-7-thiabicyclo[2.2.2]octane 
• 178261-56-8 4-Bromomethyl-9-phenyl-3,5,8,10-tetraoxabicyclo[5.3.0]decane 
• 56124-48-2 monomethyl 1,2,3,6-tetrahydrophthalate 

Relevant academic research and scientific papers

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

DSD acid preparation method

The invention relates to the field of chemical synthesis, in particular to a DSD acid preparation method. The DSD acid preparation method includes the steps that methylbenzene is subjected to sulfonation, purification and separation to obtain OTS, wherein the byproduct is PTS; OTS is subjected to mixed acid nitration to obtain PNTS; PNTS is subjected to chlorine oxidative condensation to obtain DNS; DNS is subjected to catalyzed hydrogeneration reduction to obtain the high-quality target product, namely DSD acid which can be directly used for synthesizing a fluorescent whitening agent. The synthesis method greatly reduces dangerousness of the process, greatly reduces generation of harmful byproducts and waste, particularly, does not generate a lot of carcinogenic intermediate, namely ortho-nitrotoluene, completely solves the nitration safety problem of the old technology, and has the advantages of being simple in step, high in yield and the like.

Architectural diversity and elastic networks in hydrogen-bonded host frameworks: From molecular jaws to cylinders

Guest-free guanidinium organomonosulfonates (GMS) and their inclusion compounds display a variety of lamellar crystalline architectures distinguished by different "up-down" projections of the organomonosulfonate residues on either side of a two-dimensional (2D) hydrogen-bonding network of complementary guanidinium ions (G) and sulfonate moieties (S), the so-called GS sheet. Using a combinatorial library of 24 GMS hosts and 26 guest molecules, a total of 304 inclusion compounds out of a possible 624 possible host-guest combinations were realized, revealing a remarkable capacity of the GMS hosts to form inclusion compounds despite the facile formation of the corresponding guest-free compounds and the absence of "predestined" inclusion cavities like those in related guanidinium organodisulfonate host frameworks. The GS sheets in the inclusion compounds behave as "molecular jaws" in which organomonosulfonate groups projecting from opposing sheets clamp down on the guest molecules, forming ordered interdigitated arrays of the host organic groups and guests. Both the guest-free and inclusion compounds display a variety of architectures that reveal the structural integrity of two-dimensional GS sheet and the unique ability of these hosts to conform to the steric demands of the organic guests. Certain GMS host-guest combinations prompt formation of tubular inclusion compounds in which the GS sheet curls into cylinders with retention of the 2D GS network. The cylinders assemble into hexagonal arrays through interdigitation of the organosulfonate residues that project from their outer surfaces, crystallizing in high-symmetry trigonal or hexagonal space groups. This unique example of network curvature and structural isomerism between lamellar and cylindrical structures, with retention of supramolecular connectivity, is reminiscent of the phase behavior observed in surfactant microstructures and block copolymers. The large number of host-guest combinations explored here permits grouping of the inclusion compound architectures according to the shape of the guests and the relative volumes of the organomonosulfonate groups, enabling more reliable structure prediction for this class of compounds than for molecular crystals in general.

A novel method for sulfonation of aromatic rings with silica sulfuric acid

Direct and chemoselective sulfonation of aromatic compounds with silica sulfuric acid in 1,2-dichloeoethane or under solvent-free conditions.

Clean-chemistry sulfonation of aromatics

A solution of TFAA/H2SO4 is an atom-efficient liquid-phase system for rapid sulfonation of aromatic structures; H2SO4 is consumed stoichiometrically and the spent trifluoroacetic anhydride (TFAA) is readily recovered as trifluoroacetic acid (TFA) which can be recycled to TFAA.

Nonmonotonic dependences of the activation parameters of hydrolysis of methyl-substituted benzenesulfonyl bromide on the composition of the dioxane-water binary solvent. The effect of hydrophobic interactions

Pseudo-first-order rate constants and activation parameters (ΔH≠ and ΔS≠) were determined for hydrolysis of 2-CH3- and 2,4,6-(CH3)3-substituted benzenesulfonyl bromide over wide ranges of temperature and compositions of the dioxane-water solvent. The dependences of the activation parameters on the mole fraction of dioxane (X2) are nonmonotonic, like those for the earlier studied hydrolysis of 4-toluenesulfonyl bromide. The X2 values (ranging from 0 to 0.13) corresponding to maximum Δ≠ and ΔS≠ are different for different methyl-substituted benzenesulfonyl bromides. Selective hydrophobic interactions water-sulfonyl bromide make the activation parameters reach maxima at such compositions of the binary solvent that allow each of the substrates to hydrolyze inside an individual quasi-clathrate solvation shell.

Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents

A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-σ-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro- elimination which depends on the nature and position of the R substituent.

Reactivity of sterically hindered aromatic sulfonic acid derivatives: VII.* hydrolysis of arenesulfonyl chlorides in aqueous acetonitrile

Hydrolysis of sterically hindered arenesulfonyl chlorides in aqueous acetonitrile is accelerated by both electron-acceptor and some electron-donor substituents in the benzene ring. A multifactor kinetic model of the process is proposed. 1998 MAHK Hayka/Interperiodica Publishing.

Sulfonating agent and sulfonation process

A sulfonating agent represented by the general formula STR1 wherein the groups R1 are the same or different and are each a lower alkyl group having 1 to 3 carbon atoms, n is an integer of 3, 4 or 5, m is an integer of 1 or 2, and n+m≤6, and a process for sulfonating an aromatic compound with use of the sulfonating agent.

REACTIVITY OF STERICALLY HINDERED DERIVATIVES OF AROMATIC SULFONIC ACIDS II. EFFECTS OF SUBSTRATE STRUCTURE AND MEDIUM POLARITY ON THE HYDROLYSIS OF BENZENESULFONYL CHLORIDES

The kinetics of the hydrolysis of substituted benzenesulfonyl chlorides XArSO2ClN2 mechanism.