Study On Green Synthesis Of 2,2’,4,4’,6, 6’-hexanitrostibene

2,2’,4,4’,6,6’-hexanitrostilbene, referred to as HNS, is a kind of heat-resistant insensitive explosives with high energy. For the production process of HNS at present, the preparation of HNBB was improved and a new production process of HNS from HNBB was proposed in this paper. Not only that, we reused the reacting solvent of HNS preperation from HNBB cyclically. Therefore, the new process could significantly lower the production cost and reduce environmental pollution.TNT was efficiently oxidized to hexanitrobibenzyl (HNBB) with goods sodium hypochlorite. The reaction conditions were optimized by means of single factor experiments and orthogonal tests. The yield of HNBB was 80.0% in ethanol/ethyl acetate only when pH of sodium hypochlorite solution was 12.8 and dosage was 3.5mL NaC10/1g TNT. The temperature was 53℃ and the reaction lasted for 1h. We purified the raw product by boiled and washed it in methanol.A new reaction process of HNS was studied. HNS was produced efficiently via the dehydrogenation of HNBB with O2 catalyzed by 4-OH-TEMPO/FeCl2-4H2O in DMSO. The reaction conditions were optimized. The materials fed composition was m(HNBB): V(DMSO):m(4-OH-TEMPO):m(FeCl2·4H2O)=1g:10mL:0.02g:0.04g.The temperature was 55℃ and the reaction lasted for 1h. Raw product was purified by boiled and washed in acetone and nitric acid successively. The yield of HNS was up to 81.5%. Possible mechanism was proposed. O2 combined with Fe2+oxidized HNBB to HNS.4-OH-TEMPO was the co-catalyst which promoted the circulation of Fe2+and speeded up the oxidation.Mother liquor of HNS preparation was reused cyclically in the process. DMSO, 4-OH-TEMPO and FeCl2-4H2O in mother liquor all were recycled actually. Compared with no-reuse process in the same case, this one saved 2/3 catalyst cost and 3/4 solvent cost. The reaction conditions were optimized in this paper. Mother liquor could be reused 5 times. In each cycling reaction, DMSO was needed to supply 10% of primal solvent dosage.4-OH-TEMPO was supplied 20% of its primal catalyst dosage, and FeCl2-4H2O was supplied 60% of that. The average yield of HNS achieved 83%. What’s more, there’s no amplification effect in the process.