CN110746358B - 一种硝基硼烷类离子液体及其制备方法 - Google Patents
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 31
- NEDSNEBJDQRRCD-UHFFFAOYSA-N B[N+]([O-])=O Chemical compound B[N+]([O-])=O NEDSNEBJDQRRCD-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000013067 intermediate product Substances 0.000 claims abstract description 13
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 8
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910000085 borane Inorganic materials 0.000 claims description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000446 fuel Substances 0.000 abstract description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910010277 boron hydride Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001768 cations Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- -1 nitroborane anion Chemical class 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
本发明公开了一种硝基硼烷类离子液体及其制备方法,包括以下步骤:(1)将三硝基甲烷在乙二醇二甲醚的作用下和硼氢化钠反应得到中间产物;(2)将中间产物与溴盐反应得到含能离子盐。该类离子液体氧化性与还原性基团共存在同一离子骨架结构,可使得离子液体燃烧更充分,是一种有潜力的肼类燃料替代物。
Description
技术领域
本发明涉及离子液体技术领域,具体涉及一种硝基硼烷类离子液体及其制备方法。
背景技术
甲基肼或偏二甲肼类燃料是目前航天液体火箭推进系统应用最广的一类燃料,该类燃料价格低,制备工艺成熟,但毒性高、对环境危害大,其高挥发性的特点则对运输及存储环境提出了较高的要求。随着科技的发展,人们对各类材料的环保性提出了更高的要求,由此引起了各国学者的高度关注并进行了大量环境友好型肼类替代物的研究。
离子液体是21世纪初发展起来的一种绿色材料,其饱和蒸汽压极低、不易挥发、结构可设计、液态可操作温区宽、无毒或低毒,在能源、医药、化工等领域都有较为广泛的应用。2008年美国爱德华兹空军基地首先证实了离子液体与氧化剂反应可以“自燃”,随后各类“自燃型”离子液体被开发出来,其中以硼氢类离子液体性能最为优异,因此对硼氢类离子液体的研究也最为集中,该类研究都将硼氢基团作为还原剂引入阴阳离子结构中,在与氧化剂白烟硝酸等接触后发生氧化还原反应迅速放热,达到材料燃点后生成火焰。由于氧化剂与还原剂被分散在两种不同材料中,因此在燃烧过程中常常存在燃烧不充分等问题。Guillaume等报道了一种室温下稳定的硝基硼烷阴离子,但并未对该类离子的性能进行研究,将该类离子应用于推进剂领域尚属首次。
发明内容
本发明的目的在于提供一种新型的硝基硼烷类离子液体及其制备方法。该类离子液体氧化性与还原性基团共存在同一离子骨架结构,可使得离子液体燃烧更充分,是一种有潜力的肼类燃料替代物。
为了达到上述目的,本发明采用如下技术方案:
一种硝基硼烷类离子液体的制备方法,包括以下步骤:(1)将三硝基甲烷在乙二醇二甲醚的作用下和硼氢化钠反应得到中间产物;(2)将中间产物与溴盐反应得到含能离子盐。
其合成路线如下:
进一步的技术方案为,所述三硝基甲烷与硼氢化钠的物质的量之比为1:1~1:5。
进一步的技术方案为,所述中间产物与溴盐的物质的量之比为2:1~1:5。
进一步的技术方案为,所述步骤(1)具体为将三硝基甲烷溶于乙二醇二甲醚中,然后快速向其中加入硼氢化钠的乙二醇二甲醚悬浊液,室温下搅拌0.5h后加入正戊烷多次洗涤,随后加入二氯甲烷后过滤,取滤液在-40℃条件下真空干燥后得到中间产物。
进一步的技术方案为,所述步骤(2)具体为将中间产物和乙腈混合均匀后向其中加入溴盐,继续反应24~30小时,反应结束后过滤除去不溶物,滤液移去溶剂干燥后得目标化合物。
更进一步的,所述步骤(2)具体为将中间产物和乙腈混合均匀后向其中加入溴盐,继续反应28小时。
与现有技术相比,本发明具有如下有益效果:本发明将氧化性的硝基基团引入含有还原剂硼烷基团的阴离子中,并将其与适当的阳离子进行组合可以得到一类新的硝基硼烷类离子液体。该类离子液体氧化性与还原性基团共存在同一离子骨架结构,可使得离子液体燃烧更充分,是一种有潜力的肼类燃料替代物。
具体实施方式
下面结合具体实施例对本发明进行进一步的解释和说明。
实施例1
中间产物的合成:
将三硝基甲烷(0.83g,5.5mmol)溶于乙二醇二甲醚(10ml)中,随后快速向其中加入硼氢化钠的乙二醇二甲醚悬浊液(0.2gNaBH4溶于10ml乙二醇二甲醚),室温下搅拌0.5h后加入正戊烷多次洗涤,随后加入二氯甲烷后过滤,取滤液在-40℃条件下真空干燥后得到黄绿色固体1(1.43g,yield:78%)。
实施例2
目标产物的合成:
在100mL圆底烧瓶中加入化合物1(370mg,1mmol)和乙腈(60mL),混合均匀后向溶液中加入相应的溴盐(1mmol),继续反应28小时。反应结束后,过滤除去不溶物,滤液移去溶剂干燥后得相应目标化合物。
当溴盐为时,目标产物为化合物2-a。浅黄色液体,(280mg,86%),1H NMR(600MHz,DMSO-d6):δppm:0.00-0.41(m,3H,BH3),5.03-5.07(m,2H,CH2),5.71(m,3H,CH,CH2),7.79(d,H,CH),7.99(d,H,CH),8.92(s,H,CH),3.73(s,3H,CH3).13C NMR(150MHz,DMSO-d6):δ:ppm:37.1,53.0,117.2,122.9,132.5,137.0,179.7.Elemental analysis,calcd(%)for C8H14BN5O6(287.1):C:33.48,H:4.92,N:24.40,Found,C:33.89,H:5.27,N:23.19。
当溴盐为时,目标产物为化合物2-b,浅黄色液体,(234mg,85%),1H NMR(600MHz,DMSO-d6):δppm:0.02-0.41(m,3H,BH3),1.57(m,3H,CH3),4.82(m,2H,CH2),7.76(d,H,CH),7.92(d,H,CH),8.95(s,H,CH),3.73(s,3H,CH3).13C NMR(150MHz,DMSO-d6):δ:ppm:16.5,55.1,122.8,123.1,137.0,37.2,179.7.Elemental analysis,calcd(%)for C7H14BN5O6(287.1):C:30.57,H:5.13,N:25.46,Found,C:30.89,H:5.87,N:24.98。
当溴盐为时,目标产物为化合物2-c,无色液体,(245mg,88%),1H NMR(600MHz,DMSO-d6):δppm:0.03-0.40(m,3H,BH3),1.25(m,3H,CH3),3.30(m,2H,CH2),3.23(m,4H,CH2),1.71(m,4H,CH2),3.30(s,3H,CH3).13C NMR(150MHz,DMSO-d6):δ:ppm:8.0,22.1,49.2,56.2,64.6,179.8.Elementalanalysis,calcd(%)for C8H19BN4O6(278.1):C:34.56,H:6.89,N:20.15,Found,C:34.87,H:7.25,N:19.98。
当溴盐为时,目标产物为化合物2-d,无色液体,(238mg,83%),1H NMR(600MHz,DMSO-d6):δppm:0.03-0.40(m,3H,BH3),1.55(m,3H,CH3),3.35(m,2H,CH2),2.90(m,3H,CH3),4.90(d,2H,CH),5.79(m,2H,CH),2.69(m,2H,CH2).13C NMR(150MHz,DMSO-d6):δ:ppm:6.4,30.3,44.7,56.3,129.1,133.3,179.8.Elemental analysis,calcd(%)for C9H17BN4O6(288.1):C:37.53,H:5.95,N:19.45,Found,C:37.92,H:6.42,N:18.99。
当溴盐为时,目标产物为化合物2-e,无色液体,(257mg,85%),1H NMR(600MHz,DMSO-d6):δppm:0.03-0.40(m,3H,BH3),0.94(m,3H,CH3),2.08(m,2H,CH2),3.30(m,2H,CH2),2.90(m,3H,CH3),4.90(d,2H,CH),5.79(m,2H,CH),2.68(m,2H,CH2).13C NMR(150MHz,DMSO-d6):δ:ppm:11.3,15.6,30.2,45.2,65.8,129.0,132.3,179.8.Elemental analysis,calcd(%)for C10H19BN4O6(302.1):C:39.76,H:6.34,N:18.55,Found,C:40.01,H:6.92,N:18.19。
当溴盐为时,目标产物为化合物2-f,无色液体,(266mg,87%),1H NMR(600MHz,DMSO-d6):δppm:0.03-0.41(m,3H,BH3),0.89(m,3H,CH3),1.30(m,2H,CH2),1.72(m,6H,CH2),3.22(m,6H,CH2),3.30(s,3H,CH3).13C NMR(150MHz,DMSO-d6):δ:ppm:13.8,19.0,22.0,23.2,49.9,61.6,65.0,179.6.Elemental analysis,calcd(%)for C10H23BN4O6(306.2):C:39.24,H:7.57,N:18.30,Found,C:39.91,H:8.03,N:17.98。
尽管这里参照本发明的解释性实施例对本发明进行了描述,上述实施例仅为本发明较佳的实施方式,本发明的实施方式并不受上述实施例的限制,应该理解,本领域技术人员可以设计出很多其他的修改和实施方式,这些修改和实施方式将落在本申请公开的原则范围和精神之内。
Claims (7)
2.根据权利要求1所述的硝基硼烷类离子液体的制备方法,其特征在于,所述三硝基甲烷与硼氢化钠的物质的量之比为1:1~1:5。
3.根据权利要求1所述的硝基硼烷类离子液体的制备方法,其特征在于,所述中间产物与溴盐的物质的量之比为2:1~1:5。
4.根据权利要求1所述的硝基硼烷类离子液体的制备方法,其特征在于,所述步骤(1)具体为将三硝基甲烷溶于乙二醇二甲醚中,然后快速向其中加入硼氢化钠的乙二醇二甲醚悬浊液,室温下搅拌0.5~1h后加入正戊烷多次洗涤,随后加入二氯甲烷后过滤,取滤液在-40℃条件下真空干燥后得到中间产物。
5.根据权利要求1所述的硝基硼烷类离子液体的制备方法,其特征在于,所述步骤(2)具体为将中间产物和乙腈混合均匀后向其中加入溴盐,继续反应24~30小时,反应结束后过滤除去不溶物,滤液移去溶剂干燥后得目标化合物。
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