80-82-0Relevant articles and documents
Orthanilic acid synthesizing method
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Paragraph 0053; 0055; 0066; 0076; 0086; 0097; 0108, (2018/03/25)
The invention discloses an orthanilic acid synthesizing method. The method includes steps: step one, taking water as a reaction medium, mixing ortho-nitrochlorobenzene and sodium disulfide solution, and stirring at 60-90 DEG C until reaction is finished, so that bis(dinitrophenyl)disulfide is obtained; step two, taking water as a reaction medium, adding the bis(dinitrophenyl)disulfide while addingan oxidant into a reaction system, stirring at 60-90 DEG C until reaction is finished, so that aqueous solution of o-nitrobenzenesulphonic acid is obtained; step three, taking water as a reaction medium and o-nitrobenzenesulphonic acid as a reaction substrate, adding or not adding auxiliary agents, adding catalysts under conditions of 90-120 DEG C and 0.8-2.0MPa, stirring until reaction is finished, and acidizing to obtain orthanilic acid. The orthanilic acid yield of the method reaches 90% or above and increased by 20% or above as compared with that of an old process, product purity is higher than 99.5%, and great crystal form and freeness of metal ion residues are realized. The method has advantages of high economic benefits, environmental friendliness and the like.
Method for synthesizing orthanilic acid by hydrogenation method
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Paragraph 0027; 0028; 0029; 0030, (2019/01/14)
The invention discloses a method for synthesizing orthanilic acids by a hydrogenation method. The synthesis method comprises the following steps: performing sulfonation reaction on o-nitrochlorobenzene with nitrosonitric acid and concentrated sulfuric acid, and separating high-purity o-Nitrobenzenesulphonic acid after completion of the reaction; forming a clathrum with nitrogen-doped porous coatedcarbon palladium or platinum catalyst, transferring o-Nitrobenzenesulphonic acid to an atomizer for atomization, and adding o-Nitrobenzenesulphonic acid solid in the bottom of a kettle and liquefying; firstly pumping into dry hydrogen gas, starting stirring and circulation reflux, spraying the atomized o-Nitrobenzenesulphonic acid into the kettle, and stoping the reflux after the reaction is completed; introducing the nitrogen gas firstly to exhaust the gas, then crystallizing orthanilic acid, centrifugally separating liquid solid after crystallization and performing suction filtration, and then baking the solid at high temperature to obtain orthanilic acid. The method for synthesizing orthanilic acids by the hydrogenation method uses nitrogen-doped porous carbon as a catalyst carrier andthe catalyst is made into a lattice for gas-gas reaction, and then the reflux and spraying of liquefied o-Nitrobenzenesulphonic acid is circulated, thus producing a high-purity substrate.
Aryl sulfonic acid ammonium salt compound, preparation method and application thereof (by machine translation)
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Paragraph 0027; 0036, (2018/03/25)
The invention discloses a aryl sulfonic acid ammonium salt compound, preparation method and application thereof, the main process expressed as follows: formula (I) indicated by the aryl sulfonic acid compound crude product as raw material, in the solvent with the structural formula (II) shown in mixed organic amine, to form the structural formula (III) as shown by a aryl sulfonic acid ammonium salt; the resulting structural formula (III) aryl sulfonic acid ammonium salt shown by the alkali soluble acid or directly to obtain the acid of formula (I) shown in the purification of compounds such as aryl sulfonic acid. The invention is primarily embodied in the [...]: through the low quality aryl sulfonic acid compound refining, effectively reduces the content of harmful impurities, improve the quality of the aryl sulfonic acid compound, reducing the pressure of the downstream use, the process is stable. (by machine translation)
Development of 1-Hydroxy-2(1H)-quinolone-Based Photoacid Generators and Photoresponsive Polymer Surfaces
Ikbal, Mohammed,Banerjee, Rakesh,Atta, Sanghamitra,Jana, Avijit,Dhara, Dibakar,Anoop, Anakuthil,Singh, N. D. Pradeep
, p. 11968 - 11975 (2012/10/29)
A new class of carboxylate and sulfonate esters of 1-hydroxy-2(1H)- quinolone has been demonstrated as nonionic photoacid generators (PAGs). Irradiation of carboxylates and sulfonates of 1-hydroxy-2(1H)-quinolone by UV light (γ≥310 nm) resulted in homolysis of weak N-O bond leading to efficient generation of carboxylic and sulfonic acids, respectively. The mechanism for the homolytic N-O bond cleavage was supported by time-dependent DFT calculations. Photoresponsive 1-(p-styrenesulfonyloxy)-2-quinolone-methyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolone-lauryl acrylate (SSQL-LA) copolymers were synthesized from PAG monomer 1-(p-styrenesulfonyloxy) -2-quinolone, and subsequently controlled surface wettability was demonstrated for the above-mentioned photoresponsive polymers. Copyright
Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids
Ikbal, Mohammed,Jana, Avijit,Singh, N.D. Pradeep,Banerjee, Rakesh,Dhara, Dibakar
, p. 3733 - 3742 (2011/06/21)
Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (≥254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N- phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids.
2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues
Hodson, Stephen J.,Bishop, Michael J.,Speake, Jason D.,Navas III, Frank,Garrison, Deanna T.,Bigham, Eric C.,Saussy Jr., David L.,Liacos, James A.,Irving, Paul E.,Jeffrey Gobel,Sherman, Bryan W.
, p. 2229 - 2239 (2007/10/03)
A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.
Exploiting differences in solution vs solid-supported reactivity for the synthesis of sulfonic acid derivatives
Hari, Anitha,Miller, Benjamin L.
, p. 2109 - 2111 (2008/02/10)
(matrix presented) Quantitative We describe a method herein for the protection of aryl and alkyl sulfonates during synthesis which employs commercially available Wang or MBOH resin, both of which terminate as benzyl alcohols, as both a protecting group and "traceless" linker. Given the known instability of benzylic sulfonate esters to nucleophilic displacement in solution, this linkage is surprisingly stable: no loss of either aryl or alkyl sulfonates is observed when the resin is exposed to a wide variety of organic bases and solvents at room temperature. Further elaboration of the resin-bound sulfonates via Suzuki coupling is also described.
Hydrolysis and Alcoholysis of Esters of o-Nitrobenzenesulfonic Acid
Sendega,Makitra,Pirig
, p. 1438 - 1446 (2007/10/03)
The rate of solvolysis of esters of o-nitrobenzenesulfonic acid with water and C1-C4 alcohols is satisfactorily described by two-parametric Hammett-Taft equation with predominating effect of the electronic factor σ*. The effect of the structure of the hydrocarbon rest in the sulfonic ester group does not fit to this relationship.
KINETICS AND MECHANISM OF HYDROLYSIS OF AROMATIC SULFONYL CHLORIDES IN AQUEOUS SULFURIC ACID SOLUTIONS
Gnedin, B. G.,Ivanov, S. N.,Shchukina, M. V.
, p. 731 - 737 (2007/10/02)
The kinetics of the hydrolysis of 12 aromatic sulfonyl chlorides were studied by a spectrophotometric method in water and aqueous sulfuric acid solutions ( 1.0 - 60.5 wt.percent ) at 25 deg C and in 50percent sulfuric acid at several temperatures.It was shown that the reaction obeys the single-parameter equation log keff = log k0 + m'X, in which keff and k0 are the first-order rate constants in a solution with "excess acidity" X and in water respectively.The coefficient m' depends on the substituent in the ring and is equal to -0.85 to -0.38.The activity of the water does not enter into the equation for the calculation of keff.For the hydrolysis of nine substituted sulfonyl chlorides in 50percent sulfuric acid a satisfactory correlation is observed between log keff and the Σ?0.Palm induction constants ( ρ = -1.85 +/- 0.12 ).A reaction mechanism is proposed in which the rate-determining stage in the hydrolysis of the ArSO2Cl is the transformation of the complex H2O...SO2(Cl)Ar, in the form of which all the sulfonyl chloride dissolved in the water is present, into the reaction products.
STUDIES ON SULFENAMIDES. VI. CYCLIC VOLTAMMETRY AND CONTROLLED POTENTIAL ELECTROLYSIS OF 4'-SUBSTITUTED 2-NITROBENZENESULFENANILIDES IN THE PRESENCE OF TRIFLUOROACETIC ACID OR PYRIDINE
Sayo, Hiroteru,Mori, Koichi,Michida, Takashi
, p. 2598 - 2603 (2007/10/02)
Anodic oxidation of 4'-substituted 2-nitrobenzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-H (1c), 4'-Cl (1d), 4'-COOEt (1e), 4'-COCH3 (1f), 4'-NO2 (1g) and 4'-ethoxycarbonyl-N-methyl-2-nitrobenzenesulfenanilide (1h) was investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon or a reticulated vitreous carbon anode in acetonitrile containing 1 percent trifluoroacetic acid (TFA) or 1 percent pyridine.The peak potentials of 1a-g in acetonitrile containing TFA were 0.23-0.55 V more positive than those in acetonitrile containing pyridine.On the other hand, the peak potential of 1h was not affected by addition of TFA or pyridine.This suggests that 1a-g partially dissociate into the sulfenamide anions in the presence of pyridine.Electrolysis of 1a, 1b, and 1d in the presence of TFA gave the corresponding 2,7-disubstituted phenazines in higher yields than that in the absence of TFA.Electrolysis of 1a-d the presence of pyridine gave the corresponding pyridinated sulfenanilides, and that of 1e and 1f gave the corresponding 4,4'-disubstituted azobenzenes.Electrolysis of 1g gave p-nitroaniline both in the absence and presence of pyridine.The variation of yields of the phenazines and species of the products was explained in terms of the extent of dissociation of the dication intermediate, which in turn depends on the 4'-substituent.The nitrenium ions and nitrines are suggested to be intermediates in the formation of the corresponding phenazines and the primary amines, respectively.The azobenzenes are considered to be oxidation products of the primary amines, respectively.The azobenzenes are considered to be oxidation products of the primary amines.Keywords: - anodic oxidation; cyclic voltammetry; 2-nitrobenzenesulfenanilides; 2,7-disubstituted phenazines; oxidation of sulfenamides; nitrenium ion; nitrine; RVC; N-arylpyridinium perchlorate
