120-18-3Relevant academic research and scientific papers
Microwave heating as a new way to induce selectivity between competitive reactions. Application to isomeric ratio control in sulfonation of naphthalene
Stuerga,Gonon,Lallemant
, p. 6229 - 6234 (1993)
Heating rate associated with microwave heating are used to control isomeric ratio in sulfonation of naphtalene. General considerations about use of microwave heating in organic syntheses are also considered. The authors show specificities of microwave heating in term of reactivity, associated with control of very fast heating rate.
Micellar Effects upon Rates of SN2 Reactions of Chloride Ion. 2. Effects of Cationic Headgroups
Bacaloglu, Radu,Bunton, Clifford, A.,Cerichelli, Giorgio,Ortega, Francisco
, p. 5068 - 5073 (1990)
Observed first-order rate constants for reaction of methyl naphthalene-2-sulfonate with Cl- in micelles of cetyltrialkylammonium chlorides (C16H33NR3Cl, R -= Me, Et, n-Pr, n-Bu, n-Pe) increase with increasing concentrations of surfactant and Cl- and tend to limiting values.These variations can be fitted to a model that describes micelle-ion interactions in terms of Langmuir isotherms.The binding parameters, K'Cl , decrease with increasing headgroup bulk, but second order rate constants at the surface increase.The value of K'Cl is higher with a quinuclidinium as compared with N+R3 headgroup, but the second-order rate constant is similar to that for R = Et.Values of K'Cl are high with hydroxyethyl head groups N+R3 = N+Me2CH2CH2OH or N+(CH2CH2OH)3, but these groups decrease second-order rate constants.Values of K'Cl estimated from 35Cl NMR line widths agree with the kinetic values except with the N+(CH2CH2OH)3 headgroup for which the kinetic values are much higher.The effect of headgroup bulk upon the spontaneous reaction with water was examined by using sulfate as the surfactant counterion.Trends in reactivity are very similar for reactions of H2O and Cl-.
Neopentyl ester protecting groups for arylsulfonic acids
Roberts, John C.,Huai, Gao,Gopalsamy, Ariamala,Kongsjahju, Azis,Patch, Raymond J.
, p. 355 - 358 (1997)
We report that neopentylsulfonate esters are stable to a variety of standard organic reaction conditions and are easily cleaved to sulfonic acids. We also discuss the use of N-Boc-4-amino-2,2-dimethylbutyl-1-sulfonate esters which may be cleaved under conditions that are suitable for solid phase synthesis.
Synthesis of optically pure 3,3′-diaryl binaphthyl disulfonic acids via stepwise N-S bond cleavage
Hatano, Manabu,Ozaki, Takuya,Nishikawa, Keisuke,Ishihara, Kazuaki
, p. 10405 - 10413 (2013)
We developed a practical synthesis of optically pure 3,3′-diaryl-1, 1′-binaphthyl-2,2′-disulfonic acids (i.e., (R)- or (S)-3,3′-Ar2-BINSAs) from the parent chiral sulfonimides via stepwise N-S bond cleavage of the sulfonimides and the resultant sulfonamides. This unusual synthesis, which provides arylsulfonic acids from arylsulfonamides, is valuable since common methods particularly give amines with the decomposition of sulfone groups during deprotection.
The sulfonation of aromatic and heteroaromatic polycyclic compounds
Katritzky, Alan R.,Kim, Myong Sang,Fedoseyenko, Dmytro,Widyan, Khalid,Siskin, Mike,Francisco, Manuel
, p. 1111 - 1114 (2009)
Relative reactivities of a series of polycyclic carbo- and heteroaromatic compounds to sulfonation by sulfur trioxide in nitrobenzene are measured and discussed. The results show the following reactivity in decreasing order: indole, carbazole, pyrene, perylene, naphthalene, phenanthrene, benzene, benzothiophene, and dibenzothiophene.
Effects of micellar head group structure on the spontaneous hydrolysis of methyl naphthalene-2-sulfonate. The role of perchlorate ion
Brinchi, Lucia,Di Profio, Pietro,Germani, Raimondo,Savelli, Gianfranco,Spreti, Nicoletta,Bunton, Clifford A.
, p. 361 - 364 (1998)
The spontaneous (SN2) hydrolysis of methyl naphthalene-2-sulfonate (MeONs) in water is inhibited by cationic, anionic and zwitterionic micelles of the following surfactants, CTAOMs, n-C16H33N+Me3MeSO3 -; CTPAOMs, n-C16H33N+Pr3MeSO3 -; SDS, C12H25OSO3-Na+; SB3-14, n-C14H29N+Me2(CH2) 3SO3-;-SBBu3-14, n-C14H29N+Bu2(CH2) 3SO3-; DMMAO, n-C14H29N+Me2O-; DPMAO, n-C14H29N+Pr2O-. Rate constants, krel, relative to those in water, are in the range 0.55-0.63 for all the cationic and zwitterionic micelles including the protonated amine oxides. The value of krel in anionic micelles of SDS is 0.22, but NaClO4 sharply decreases krel in SB3-14 from 0.56 to 0.15. These rate effects are not related to variations in substrate binding but depend upon interactions of the head groups with the initial and transition states.
Synthesis and structural elucidation of sulfonated naphthalene-formaldehyde
Moradian,Mahmoodi,Shemshadi
, p. 578 - 584 (2009)
The synthesis, characterization, structural elucidation, and application of the dispersant obtained from the condensation of -naphthalene sulfonic acid and formaldehyde are reported. The one-pot synthesis from naphthalene, sulfuric acid, and formaldehyde leads to reproducible polymers with 13 and 14 naphthalene nuclei. The 1H and 13C NMR spectra in D2O (representative spherical shape) and DMSO (representative rod-like shape) are reported. The belching technique led to excellent super pure material.
Preparation method of clean product 1, 6 and 1,7 mixed
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Paragraph 0037-0040, (2020/06/16)
The invention relates to a preparation method of a cleaning type product 1,6- and 1,7-Cleve's acid. The method comprises the following steps: performing sulfonation on refined naphthalene to obtain 2-naphthalene sulfonic acid, performing nitration for the formation of a mixture of 1-nitro-6-naphthalenesulfonic acid and 1-nitro-7-naphthalenesulfonic acid, performing neutralization through ammonia water, and finally performing hydrazine hydrate reduction to obtain the 1,6- and 1,7-Cleve's acid. Compared with original production process, the method provided by the invention has no generation of waste residue in the whole process, the purpose of emission reduction is achieved, and the process is more simple and convenient, and has safety and effectiveness. In addition, the overall cost of theprocess provided by the invention is lower than the overall cost of an original process.
Synthetic process of naphthol
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022, (2017/08/29)
The invention discloses a synthetic process of naphthol. The process comprises the followings steps: sulfonation, neutralization, alkali fusion, and acidification. The sulfonation step comprises the following steps: a sulfonation reaction is carried out for naphthalene and sulfuric acid whose mass fraction is 98% in the existence of a water carrying agent, a characteristic that the water carrying agent and water form an azeotrope is applied, water which is generated in the reaction is separated continuously from a reaction system, and naphthalene and sulfuric acid are nearly reacted completely. Obtained 1-naphthalenesulfonic acid is neutralized, alkali fusion and acidification are directly carried out in order to obtain a naphthol crude product. The process has the advantages of simplified operation, little low of naphthalene and sulfuric acid, high utilization rate, high naphthalene conversion rate which reaches 94% or above, low amount of waste water, and a few amount of sodium sulfate waste water which is only generated after multiple circulations.
A dilute sulfuric acid recovery method for using (by machine translation)
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Paragraph 0021, (2016/11/24)
The invention discloses a method for recovering and utilizing dilute sulfuric acid, characterized in that comprises the following steps: in the reaction with rectification, the dilute sulfuric acid and double-ring aromatic hydrocarbon, or/and polycyclic aromatic hydrocarbon in the distillation together with, in the rectification process, the water as the light component, from the rectification tower, the concentration of sulfuric acid in the kettle, the kettle warmly rise; when cauldron mass concentration of sulfuric acid in > 63% time, the temperature of the kettle for 150-175°C, sulfuric acid and double-ring aromatic hydrocarbon, or/and polycyclic aromatic sulfonation reaction occurs, the water is generated at the same time, and the concentration of sulfuric acid in the rectification heating water outlet, so cycle, until complete reaction consumption of sulfuric acid in the kettle. In the invention, the dilute sulfuric acid rectification concentrated use and double ring/multi-ring aromatic sulfonated combination, does not need high-temperature, can be realized by using concentrated and dilute sulfuric acid. (by machine translation)
