5180-53-0

Upstream product

• 118-96-7 2,4,6-Trinitrotoluene 
• 7664-93-9 sulfuric acid 
• 2220-30-6 1,2-Bis(2,4-dinitrophenyl)ethane 
• 7697-37-2 nitric acid 
• 854211-24-8 2,4,6,2',4'-pentanitro-bibenzyl 
• 7176-28-5 2,4,6-Trinitrobenzyl chloride 
• 736-30-1 1,2-bis(4-nitrophenyl)ethane 

Downstream Products

• 20062-22-0 2,2’,4,4’,6,6’-hexanitrostilbene 
• 19138-90-0 2,2',4.4',6,6'-hexanitrostilbene 

Relevant academic research and scientific papers

A 2,2 the [...], 4,4 the [...], 6,6 the nitro-six [...] process for the preparation of diphenyl ethylene

The present invention relates to a 2,2',4,4',6,6'-hexanitro diphenylethylene preparation method, which comprises that: (1) 2,4,6-trinitrotoluene and sodium hypochlorite are subjected to a reaction in a reaction solvent to prepare hexanitro bibenzyl, wherein the reaction solvent is a mixing solution of ethanol and benzene, and (2) the hexanitro bibenzyl and bromine are subjected to a reaction in a reaction solvent to prepare 2,2',4,4',6,6'-hexanitro diphenylethylene, wherein the reaction solvent is a mixing solution of dichloroethane and pyridine, the reaction solutions in the step (1) and the step (2) can be filtered to collect the filtrates, and the filtrates can be used as the reaction solvent of the corresponding steps. Compared with the preparation method in the prior art, the preparation method of the present invention has the following characteristics that: the coupling reaction solvents can be recycled, the solvent loss in the dehydrogenation reaction is less, and the pyridine consumption is less.

A Green and Effective Approach of Two-Step 2,2′,4,4′,6,6′-Hexanitrostilbene Preparation and Its Industrial Scale Study

An environmental friendly approach for two-step synthesis of hexanitrostilbene (HNS) has been studied here. In the first step from trinitrotoluene (TNT) to hexanitrobienzyl (HNBB), commercial NaClO was employed as oxidant in mixed solvent of ethyl acetate/ethanol (0.25 mL/1.25 mL per mmol of TNT) instead of benzene/ethanol. In the second step from HNBB to HNS, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)/FeCl2 was used as an effective catalytic system with O2 in DMSO solvent. A complex of metal ion and O2 [M(n+1)OO?] was supposed to be the active agent, and TEMPO itself was difficult to initiate dehydrogenation of HNBB but could promote the catalytic cycle of complex M(n+1)OO?. Finally, we increased the scale from 30 to 1000 g to investigate the feasibility of production. The total yield of two steps would be unprecedentedly as high as 70%.

Facile and efficient reductive homocoupling of benzyl and aryl halides catalyzed by ionic liquid [C12mim][CuCl2] in the presence of metallic zinc and copper

A facile and efficient synthesis of bibenzyl and biaryl derivatives by reductive homocoupling reaction is described. Treatment of benzyl and aryl halides with metallic zinc and copper powder in the presence of a catalytic amount of [C12mim][CuCl2] under ligand- and base-free conditions gives the corresponding bibenzyls and biaryls in good to high yields. The product can be isolated by a simple extraction with organic solvent, and the catalytic system can be recycled or reused without any significant loss of catalytic activity.

Synthesis of hexanitrostilbene (HNS) using a kenics static mixer

Previous work on a Shipp-Kaplan type synthesis of hexanitrostilbene (HNS) using a Kenics static mixer (ref1, from Chemineer Ltd., Cranmer Road, West Meadows, Derby DE21 6XT, UK; www.chemineer.com) has been extended by using a larger mixer (9.5 mm vs 4.75 mm OD), enabling the scale to be increased from 2.5 g to 25 g of trinitrotoluene (TNT) for the same mixing time (2SO4 and NaOH solutions, and (iii) pH control using aqueous RNH3Cl and RNH2 solutions. Other parameters that have been varied are the ratio of NaOCl to TNT (0.5-1.2) and the concentration of both reactants. The yields of crude HNS that have been achieved, whilst not outstanding, are an improvement over the conventional batch process. It has been demonstrated that the yield and selectivity of the HNS synthesis can be considerably increased if, during the after-reaction period, the reaction conditions are pH controlled. The yield and selectivity are also significantly enhanced by using more dilute reaction solutions.

Production of hexanitrostilbene (HNS)

A process for the manufacture of 2,2', 4,4', 6,6-hexanitrostilbene (HNS) from dipicrylethane (DPE) or trinitrotoluene (TNT) which consists of oxidizing DPE or TNE substrate in the presence of an aprotic solvent and a basic salt of a carboxylic acid. The acid preferably consists of an ammonium or an alkali metal salt of a monocarboxylic or a dicarboxylic acid. The reaction step consists of heating the substrate and salt dissolved in the solvent to between 15° and 50° C., and contacting the reaction mixture with dry air or oxygen for up to 2 hours. The HNS product is precipitated out by quenching the reaction mixture in acidified water, and is optionally purified by washing first in methanol and then in acetone.