Page 35 - 《含能材料》2018年优秀论文
P. 35

930                                                                    邵艳丽,王乾,王鹏程,张晓鹏,姜振明,陆明

            [12] Ek S,Rehn S,Wahlström L Y,et al. Synthesis and Character⁃  al complex consisting of an all⁃nitrogen pentazole anion,a
                 ization of Eight Arylpentazoles[J]. Journal of Heterocyclic  Zn(ii)cation and H 2 O[J]. Dalton Transactions,2017(DOI:
                 Chemistry,2013,50(2):261-267.                       10.1039/c7dt03231e)
            [13] Yang Y Z,Li Y C,Zhang R B,et al. Thermal stability of p⁃di⁃  [23] Zhang Q,Zhang W,Wang K,et al. Stabilization of the pen⁃
                 methylaminophenylpentazole[J]. Rsc Advances,2014,4(4):  tazolate anion in a zeolitic architecture with Na 20 N 60 and
                 57629-57634.                                        Na 24 N 60 nanocages[J]. Angew Chem Int Ed,2018(DOI:10.
            [14] Peter Carlqvist,Henrik Östmark A,Tore Brinck. The stability  1002/ange.201710602)
                 of arylpentazoles[J]. Journal of Physical Chemistry A,2010,  [24] Lein M,Frunzke J,Timoshkin A,et al. Iron bispentazole Fe
                 108(36):7463-7467.                                  (η 5 ⁃N 5 ) 2 , a theoretically predicted high⁃energy compound:
            [15] Christe K O,Wilson W W,Sheehy J A,et al. N 5 :A novel ho⁃  structure,bonding analysis,metal⁃ligand bond strength and a
                                                  +
                 moleptic polynitrogen ion as a high energy density material[J].  comparison with the isoelectronic ferrocene[J]. Chemistry‑A
                 Angew Chem Int Ed,1999,38(13/14):2004-2009.         European Journal,2015,7(19):4155-4163.
                                       +
            [16] 于剑昆 . 超级高能量密度材料 N 5 盐的合成与表征概况[J]. 化学           [25] 章冲,胡炳成,刘成,等 . 对羟基苯基五唑及其衍生物的合成与
                 推进剂与高分子材料,2010,8(5):1-3.                            稳定性[J]. 含能材料,2016,24(8):769-773.
                 YU Jian⁃kun. Synthesis and characterization of ultra high ener⁃  ZHANG Chong,HU Bing⁃cheng,LIU Cheng,et al. Synthesis
                                   +  salts[J]. Chemical Propellants &  and stability of p⁃hydroxylphenylpentazole and its derivatives
                 gy density material of N 5
                 Polymeric Materials,2010,8(5):1-3.                  [J]. Chinese Journal of Energetic Materials,2016,24(8):
            [17] Haiges R,Schneider S,Schroer T,et al. High energy⁃density  769-773.
                                                   +
                                                           -
                 materials:Synthesis and characterization of N 5 [P(N 3 ) 6 ] ,  [26] Guisado⁃Barrios G,Zhang Y,Harkins A M,et al. Low temper⁃
                 N 5 [B(N 3 ) 4 ],N 5 [HF 2 ]· HF,N 5 [BF 4 ] ,N 5 [PF 6 ] ,and  ature reaction of[Fe(TPA)(CH 3 CN) 2 ] ,with excess 3⁃chloro⁃
                                                   +
                                              -
                                                                                                2+
                                                       -
                                          +
                  +
                              +
                                   -
                 N 5 [SO 3 F][J]. Angew Chem Int Ed,2004,43:4919-4924.  peroxybenzoic acid in semi⁃frozen acetonitrile;EPR detection
                  +
                        -
            [18] Vij A,Pavlovich J G,Wilson W W,et al. Experimental detec⁃  of an acylperoxo iron( Ⅲ ) adduct[J]. Inorganic Chemistry
                 tion of the pentaazacyclopentadienide(pentazolate)anion,cy⁃  Communications,2012,20(20):81-85.
                 clo⁃N5[J]. Angew Chem Int Ed,2002,114(16):3177-3180.  [27] Richard N B,John M H,John C S,et al. A ceric ammonium
            [19] Zhang C,Sun C G,Hu B C,et al. Synthesis and characteriza⁃  nitrate N⁃dearylation of N⁃p⁃anisylazoles applied to pyrazole,
                                              -                      triazole, tetrazole, and pentazole rings: release of parent
                 tion of the pentazolate anion cyclo⁃N 5  in (N 5 ) 6 (H 2 O) 3
                                                                                                        -
                (NH 4 ) 4 Cl[J]. Science,2017,355(6323):374-376.     azoles. generation of unstable pentazole,HN 5 /N 5 ,in solution
            [20] Xu Y G,Wang Q,Lu M,et al. A series of energetic metal pen⁃  [J]. Journal of Organic Chemistry,2008,73(4):1354-1364.
                 tazolate hydrates[J]. Nature,2017,549(7670):78-81.  [28] Richard N B,John C S,Luke A B. First generation of pen⁃
            [21] Zhang  C, Yang  C, Hu  B  C, et  al.  A  Symmetric  tazole (HN 5 ,pentazolic acid),the final azole,and a zinc
                 Co(N 5 ) 2 (H 2 O) 4 ⋅4H 2 O high⁃nitrogen compound formed by co⁃  pentazolate salt in solution:A new N⁃dearylation of 1⁃(p⁃me⁃
                 balt(Ⅱ)cation trapping of a cyclo⁃N 5 ⁃anion[J]. Angew Chem  thoxyphenyl)pyrazoles,a 2⁃(p⁃methoxyphenyl)tetrazole and
                 Int Ed,2017,56(16):4512-4514.                       application of the methodology to 1⁃(p⁃methoxyphenyl)pen⁃
            [22] Xu Y G,Wang P C,Lu M,et al. A carbon⁃free inorganic⁃met⁃  tazole[J]. Chem Comm,2003,34(31):1016-1017.
            Preparation Process and Mechanism of Cutting off the C─N Research of Sodium Pentazole Salt
            SHAO Yan⁃li ,WANG Qian ,WANG Peng⁃cheng ,ZHANG Xiao⁃peng ,JIANG Zhen⁃ming ,LU Ming    1
                                                                        2
                                   1
                                                      1
                                                                                          2
                       1
           (1. School of Chemical Engineering,Nanjing University of Science and Technology,Nanjing 210094,China;2. The Gansu Yinguang Chemical Industry Group
            Co. LTD,Baiyin 730999,China)
            Abstract:Sodium pentazole salt was prepared by treating 2,6⁃dimethyl⁃4⁃(2H⁃pentazol⁃2⁃yl)phenolate with m⁃chloroperbenzo⁃
            ic acid (m⁃CPBA) and ferrous bisglycinate [Fe(Gly) 2 ] under low⁃temperature conditions,thereinto,m⁃CPBA and Fe(Gly) 2
            were oxidizer and catalyst,respectively. The synthetic conditions were optimized,as following:the molar ratio between aryl⁃
            pentazole,Fe(Gly) 2 and m⁃CPBA was 1∶3∶4.5,the reaction time was 24 h and the reaction temperature was -45 ℃(crude
            yield of 28%). The effect of different oxidizing cleavage reagents on the yield of sodium pentazole salt was studied and the rea⁃
            son for the low yield of sodium pentazole salt was analyzed. In addition,sodium pentazole salt and the reaction by⁃product
           (2,6⁃dimethylcyclohexa⁃2,5⁃diene⁃1,4⁃dione)were characterized by X⁃ray single crystal diffractometer(XRD),NMR( NMR
                                                                                                            15
               1
            and H NMR),FT⁃IR,mass spectrometry and elemental analysis. Based on these results,the mechanism of oxidizing cleavage
            of the C─N bond in arylpentazole by m⁃CPBA and Fe(Gly) 2 was speculated.
            Key words:ionic total nitrogen energetic materials;sodium pentazole salt;preparation process;cutting off the C─N bond mechanism
            CLC number:TJ55;O62                        Document code:A                   DOI:10.11943/CJEM2018117






            Chinese Journal of Energetic Materials,Vol.26, No.11, 2018(925-930)  含能材料      www.energetic-materials.org.cn
   30   31   32   33   34   35   36   37   38   39   40