99-35-4Relevant articles and documents
Evidence for a π dimer in the electrochemical reduction of 1,3,5-trinitrobenzene: A reversible N2-fixation system
Gallardo, Iluminada,Guirado, Gonzalo,Marquet, Jordi,Vila, Neus
, p. 1321 - 1325 (2007)
(Figure Presented) Electrochemical reduction of 1,3,5-trinitrobenzene (1) forms π dimer 2, which evolves to a more stable ω complex. The crystal structure of the NEt4+ salt of 2 shows π-stacked chains of radical anions. Solid 2 or dimeric 2 in solution reacts with N2 to give a dianion in which an azo group links two 1,3,5-trinitrobenzene units (see picture). The azo derivative is reversibly electrochemically oxidized to 1.
Charge Separation on the Micelle Surface as Evidence for a Multi-step Hydrogen Transfer Mechanism in NADH Model Reduction
Shinkai, Seiji,Tsuno, Takaharu,Manabe, Osamu
, p. 592 - 594 (1982)
Reductive desulphonation of 2,4,6-trinitrobenzenesulphonate by N-dodecyl-1-benzyl-1,4-dihydronicotinamide bound to the sodium dodecyl sulphate micelle in D2O solution gave 1,3,5-trinitrobenzene which contained 4.6-5.1percent of deuterium; the result indicates that the reaction proceeds through multi-step hydrogen transfer via a radical ion-pair intermediate and the micelle surface is capable of dissociating the radical ion pair.
STERIC ACCELERATION OF REDUCTIVE DESULFONATION OF 1,8-NAPHTHALENEDISULFONATE BY AN NADH MODEL COMPOUND
Shinkai, Seiji,Kuroda, Hideo,Kusano, Yumiko,Manabe, Osamu
, p. 3201 - 3204 (1981)
1,8-Naphthalenedisulfonate was reductively desulfonated by N-benzyl-1,4-dihydronicotinamide, whereas no desulfonation was observed for the 1,6-isomer.The high reactivity of the 1,8-isomer is attributed to the steric-strain that enforces the shift of the initial state with the sp2-carbon close to the transition state with the sp3-carbon.
Preparation and vulcanizing properties of 1,3,5-trinitrosobenzene
Klyuchnikov,Khairutdinov,Klyuchnikov
, p. 1382 - 1385 (2004)
A procedure was developed for preparing a new trifunctional vulcanizing agent for unsaturated rubber composites, 1,3,5-trinitrosobenzene; its suitability as an additive to rubber-substrate adhesive formulations was examined.
Method for preparing 1, 3, 5-trinitrobenzene
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Paragraph 0014; 0019-0023, (2021/07/24)
The invention relates to a method for preparing 1, 3, 5-trinitrobenzene, and belongs to the technical field of organic intermediates. The method comprises the following steps: respectively preparing a TNT alcoholic solution and a sodium chlorite aqueous solution, adjusting the pH value of the TNT alcoholic solution with hydrochloric acid, heating to a reaction temperature, dropwise adding the sodium chlorite aqueous solution into the TNT alcoholic solution, reacting at a constant temperature, and finally filtering, washing and recrystallizing to obtain the 1, 3, 5-trinitrobenzene. Sodium chlorite is adopted as an oxidizing agent, so that oxidation and decarboxylation reactions are completed in one step, the process is simplified, and the operation cost is reduced; the energy consumption required by the reaction is low, and the product purity is high; the reaction process is safer, and the reaction yield is higher.
Synthesizing method of 2, 6 diamido-4-carboxyl benzenesulfonic acid
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Paragraph 0004; 0009, (2017/01/02)
The invention discloses a synthesizing method of 2, 6 diamido-4-carboxyl benzenesulfonic acid, which belongs to the technical field of chemical synthesis. 2,6 diamido-4-carboxyl benzenesulfonic acid is prepared by taking benzene as a raw material, adding reaction liquid mixed by concentrated nitric acid and concentrated sulfuric acid, mixing, washing with a sodium hydroxide solution, reacting with stannous chloride, iron powder and acetic acid, dropwise adding nitric acid and mixing to obtain triaminobenzene, adding sulphurous acid, under the action of sodium percarbonate, dropwise adding the sodium hydroxide solution for reaction, adding concentrated sulfuric acid after suction filtration, accelerating the reaction under the catalyst tetrabromoethane, adding hydrochloric acid for reaction, washing, performing suction filtration and cooling to room temperature. The synthesizing method has the beneficial effects of simple synthesizing steps, low cost, less side products in the preparing process, and high purity (more than 99.2%) and high yield (more than 95%) of the obtained 2,6 diamido-4-carboxyl benzenesulfonic acid.
Synthesis of thermally stable energetic 1,2,3-triazole derivatives
Kumar, A. Sudheer,Ghule, Vikas D.,Subrahmanyam,Sahoo, Akhila K.
, p. 509 - 518 (2013/02/23)
Various thermally stable energetic polynitro-aryl-1,2,3-triazoles have been synthesized through Cu-catalyzed [3+2] cycloaddition reactions between their corresponding azides and alkynes, followed by nitration. These compounds were characterized by analyti
Electrochemical synthesis of organophosphorus compounds through nucleophilic aromatic substitution: Mechanistic investigations and synthetic scope
Cruz, Hugo,Gallardo, Iluminada,Guirado, Gonzalo
experimental part, p. 7378 - 7389 (2012/02/01)
Advantages of the electrochemical approach in the nucleophilic aromatic substitution reaction, such as (a) low cost and ready availability of reagents, (b) atom economy, and (c) high yields (approaching 100 %), are applied to rationalize the (polar or radical) mechanism and to develop new greener synthetic routes for the synthesis of substituted nitroaromatic organophosphorus compounds. The nucleophiles used to study the feasibility and viability of the reaction are the classical tervalent phosphorus nucleophiles: trimethylphosphane, triethylphosphane, triphenylphosphane, diphenylphosphane, trimethyl phosphite, triethyl phosphite, dimethyl phosphonate, diethyl phosphonate, oxo(diphenyl)phosphorane, with two nitroaromatic compounds 1,3,5-trinitrobenzene and 1-chloro-2,4,6-trinitrobenzene in a DMF solution containing 0.1 M tetrabutylammonium tetrafluoroborate. In all cases, in order to establish the feasibility or benefits of the electrochemical approach relative to the chemical approach, blank reactions were also performed. Electrochemical oxidation of σH complexes and zwitterionic complexes obtained by nucleophilic attack of phosphorus nucleophiles was studied by means of cyclic voltammetry and controlled-potential electrolysis. The oxidation mechanism of those intermediates was disclosed, and the synthetic scope of the reaction was explored. Copyright
Steric hindrance as a key factor on proton transfer in the σ-adduct forming reactions of o-substituted anilines with 1,3,5-trinitrobenzene in dimethylsulfoxide
Asghar, Basim H.
scheme or table, p. 1191 - 1195 (2009/12/03)
Kinetic and equilibrium studies are reported of the reactions of 1,3,5-trinitrobenzene (TNB) with a series of o-substituted anilines in dimethyl sulfoxide (DMSO) in the presence of 1,4-diazabicyclo[2.2.2.]octane (DABCO). The pKa values in DMSO for the aniline derivatives were measured using the proton-transfer equilibrium with 2,4-dinitrophenol. Kinetic studies are compatible with a two-step process involving initial nucleophilic attack on TNB by amine to give a zwitterionic intermediate which may transfer an acidic proton to DABCO to yield the anionic product. The results indicate steric hindrance to proton transfer in reactions involving 2,6-disubstituted anilines.
Picric acid explosive compound and environmentally friendly methods for making the same
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Page/Page column 6, (2008/06/13)
An environmentally friendly picric acid explosive comprising, providing a nitromalondialdehyde, providing a dinitroketone, reacting the nitromalondialdehydes with the dinitroketone to produce a mixture, and subjecting the mixture to a cyclodehydrative mechanism to produce environmentally friendly picric acid explosive. Embodiments of the present invention include the picric acid explosive produced by the methods of described above.
