Pd(OH)2/CeO2 Catalyst for Hydrogenolytic Debenzylation Reaction of Hexabenzylhexaazaisowurtzitane and Tetraacetyl-dibenzyl-hexaazaisowurtzitane
BAO Lingxiang1, YAN Zhiyuan1, SONG Jianwei2, WEI Gaixia2, SUN Chenghui1, PANG Siping1
(1.School of Materials Science and Engineering,Beijing Institute of Technology,Beijing 100081,China;2.Qingyang Chemical Industry Corporation,Liaoyang 111001,Liaoning,China)
BAO Lingxiang, YAN Zhiyuan, SONG Jianwei, WEI Gaixia, SUN Chenghui, PANG Siping. Pd(OH)2/CeO2 Catalyst for Hydrogenolytic Debenzylation Reaction of Hexabenzylhexaazaisowurtzitane and Tetraacetyl-dibenzyl-hexaazaisowurtzitane[J]. Acta Armamentarii, 2022, 43(3): 524-532.
[1] BELLAMY A J.Reductive debenzylation of hexabenzylh- exaazaisowurtzitane[J]. Tetrahedron,1995,51(16):4711-4722. [2] SIKDER A K,SIKDER N.A review of advanced high performance,insensitive and thermally stable energetic materials emerging for military and space applications[J].Journal of Hazardous Materials,2004,112(1/2):1-15. [3] NAIR U R,SIVABALAN R,GORE G M,et al.Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (review)[J].Combustion,Explosion,and Shock Waves,2005,41(2):121-132. [4] 郑福平,欧育湘,陈江涛,等.Pd(OH)2纳米粒子的制备、结构表征及其在HBIW催化氢解中的应用[J].高等学校化学学报,1999,20(6):843-845. ZHENG F P,OU Y X,CHEN J T,et al.The preparation and characterization of nanosized Pd(OH)2 and its application in the catalytic hydrogenolysis of HBIW[J].Chemical Journal of Chinese Universities,1999,20(6):843-845.(in Chinese) [5] NIELSEN A T.Caged polynitramine compound: US5693794[P].[1997-12-02]. [6] NIELSEN A T,CHAFIN A P,CHRISTIAN S L,et al.Synthesis of polyazapolycyclic caged polynitramines[J].Tetrahedron,1998,54(39): 11793-11812. [7] 赵信岐,方涛,孙成辉.六硝基六氮杂异伍兹烷制备工艺研究开发新进展[J].兵工学报,2004,25(3):354-358. ZHAO X Q,FANG T,SUN C H.Research and development of HNIW synthesis[J].Acta Armamentarii,2004,25(4):354-358. (in Chinese) [8] BAYAT Y,EBRAHIMI H,FOTOUHI-FAR F.Optimization of reductive debenzylation of hexabenzylhexaazaisowurtzitane (the key step for synthesis of HNIW) using response surface methodology[J].Organic Process Research & Development,2012,16(11):1733-1738. [9] DONG K,CHEN Y,ZHANG Y Y,et al.The highly effective hydrogenolysis-based debenzylation of tetraacetyl-dibenzyl-hexaazaisowurtzitane(TADBIW) using a palladium/DOWEX catalyst having a synergistic effect[J].Journal of Energetic Materials,2017,35(4):1-9. [10] MAKSOMOWSKI P,GOLOFIT T,TOMASZEWSKI W.Palladium catalyst in the HBIW hydrodebenzylation[J].Central European Journal of Energetic Materials,2016,13(2):333-348. [11] 费腾,来祺,张文瑾,等.CL-20制备及晶体研究进展[J].含能材料,2021,29(4):352-368. FEI T,LAI Q,ZHANG W J,et al.Research progress of synthesis and processing of CL-20[J].Chinese Journal of Energetic Materials,2021,29(4):352-368. (in Chinese) [12] KOSKIN A P,SIMAKOVA I L,PARMON V N.Study of palladium catalyst deactivation in synthesis of 4,10-diformyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtitane[J].Reaction Kinetics and Catalysis Letters,2007,92(2):293-302. [13] FOTOUHI-FAR F,BASHIRI H,HAMADANIAN M.Study of deactivation of Pd(OH)2/C catalyst in reductive debenzylation of hexabenzyl-hexaazaisowurtzitane[J].Propellants,Explosives,Pyrotechnics,2017,42(2):213-219. [14] 邱文革,刘虎冰,董凯,等.六苄基六氮杂异伍兹烷氢解脱苄Pd(OH)2/C催化剂的制备[J].含能材料,2014,22(4):441-446. QIU W G,LIU H B,DONG K,et al. Preparation of Pd(OH)2/C catalyst for hydrogenolytic debenzylation of hexabenzyl-hexaazaisowurtzitane[J].Chinese Journal of Energetic Materials,2014,22(4):441-446.(in Chinese) [15] ZHANG M X,LIU S,LI L,et al.Effect of carbon supports on Pd catalyst for hydrogenation debenzylation of hexabenzyl-hexaazaisowurtzitane (HBIW)[J].Journal of Energetic Materials,2016,35(3):251-264. [16] LOU D Y,WANG H S,LIU S,et al.PdFe bimetallic catalysts for debenzylation of hexabenzyl-hexaazaisowurtzitane(HBIW) and tetraacetyl-dibenzylhexaazaisowurtzitane (TADBIW)[J].Catalysis Communications,2018,109:28-32. [17] LIU S,JI F,LI X Y,et al.Stick-like mesoporous titania loaded Pd as highly active and cost effective catalysts for hydrodebenzylation of hexabenzylhexaazaisowurtzitane(HBIW)[J].Molecular Catalysis,2019,477:110556. [18] 王伟,王建兵,祝万鹏,等.Ru/ZrO2·CeO2催化剂催化湿式氧化乙酸和苯酚的研究[J].分子催化,2007,21(5):401-405. WANG W,WANG J B,ZHU W P,et al. Catalvtic wet air oxidation of acetic acid and phenol with Ru/ZrO2-CeO2 catalysts[J].Journal of Molecular Catalysis,2007,21(5):401-405.(in Chinese) [19] ZHU J,GAO F,DONG L H,et al.Studies on surface structure of MxOy/MoO3/CeO2 system (M=Ni,Cu,Fe) and its influence on SCR of NO by NH3[J].Applied Catalysis B: Environmental,2010,95(1/2):144-152. [20] SHENG L P,MA Z X,CHEN S Y,et al.Mechanistic insight into N2O formation during NO reduction by NH3 over Pd/CeO2 catalyst in the absence of O2[J].Chinese Journal of Catalysis,2019,40(7):1070-1077. [21] CHEN J P,PENQUITE C R,THAKUR D S.Precious metal catalyst for debenzylation: US6992037B2[P].[2006-01-31]. [22] WU J M,ZENG L,CHENG D G,et al.Syntheis of Pd nanoparticles supported on CeO2 nanotubes for CO oxidation at low temperatures[J].Chinese Journal of Catalysis,2016,37(1):83-90. [23] WARREN B E. X-raydiffraction[M].Mineola,NY,US:Dover Publications,Inc.,1990. [24] KAPOOR M P,ICHIHASHI Y,SHEN W J,et al.Catalytic activity of palladium supported on mesoporous zirconium oxide in low-temperature methanol decomposition[J].Catalysis Letters,2001,76(3):139-142. [25] GOPINATH R,LINGAIAH N,BABU N S,et al.A highly active low Pd content catalyst synthesized by deposition-precipitation method for hydrodechlorination of chlorobenzene[J].Journal of Molecular Catalysis A: Chemical,2004,223(1/2):289-293. [26] GOPINATH R,LINGAIAH N,SREEDHAR B,et al.Highly stable Pd/CeO2 catalyst for hydrodechlorination of chlorobenzene[J].Applied Catalysis B: Environmental,2003,46(3):587-594.