CN105693521A - 三硝基双二苯乙烯类化合物的溴化产物及其合成方法 - Google Patents
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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
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- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
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- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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Abstract
本发明公开了一种三硝基双二苯乙烯类化合物的溴化产物及其合成方法。将三硝基双二苯乙烯类化合物、液溴、催化剂加入到反应器中，以二氯甲烷做溶剂，在常温下反应完成后，过滤，用饱和碳酸钠溶液中和滤液，二氯甲烷萃取，旋蒸，烘干得到所述的三硝基双二苯乙烯类化合物的溴化产物。本发明的三硝基双二苯乙烯类化合物的溴化产物，外围每个苯环上含有一个溴原子，且对称性好，可用于耐热阻燃剂、杀虫剂等方面，且中心苯环与另外二个苯环以二个共轭双键相连，大大提高了其稳定性。
Description
技术领域
本发明具体涉及一种三硝基双二苯乙烯类化合物的溴化产物及其合成方法，属于有机合成领域。
背景技术
芳香族溴化物是重要的化工原料，在国民经济各部门广泛应用，随着科技的发展，芳香族溴化物的用途范围在不断的扩大。二苯乙烯类化合物结构中存在的双键与苯环的共轭效应，使得该化合物化学性质比较稳定。如果在苯环上引入多个硝基，使其更加稳定，进而溴化条件变地更加苛刻。
迄今为止，已经发展了很多溴化方法，虽然这些方法已被广泛应用，但是他们仍有几个比较显著的缺点：1、可应用的化合物比较有限；2、有侧链副反应和过度溴化；3、溴化结果单一；4、区域选择性较差，造成原料的浪费而产生大量废液。目前，许多溴化试剂应用溴化反应中，例如溴酸、溴盐和有机溴化试剂等，但是这些溴化试剂大部分都是通过分子溴制备而来的，不但成本高、反应条件苛刻而且原子利用率低。
发明内容
本发明的目的在于提供了一种新的三硝基双二苯乙烯类化合物的溴化产物及其制备方法，所述溴化产物可应用于阻燃剂、杀虫剂等领域。
实现本发明目的的技术解决方案是：一种三硝基双二苯乙烯类化合物的溴化产物，具有以下结构：
其中R为-H、-Cl、-N(CH3)2。
一种三硝基双二苯乙烯类化合物的溴化产物的合成方法，包括以下步骤：
将三硝基双二苯乙烯类化合物、液溴、催化剂加入到反应器中，以二氯甲烷做溶剂，在常温下反应完成后，过滤，用饱和碳酸钠溶液中和滤液，二氯甲烷萃取，旋蒸，烘干得到溴化产物。
上述步骤中，三硝基双二苯乙烯类化合物结构为：
其中，R为-H、-Cl、-N(CH3)2。
上述步骤中，所述的催化剂选用H-Beta或HZSM-5和氧化锌、氧化铋、氧化铁、氧化钛中任意一种的组合。
上述步骤中，所述的三硝基双二苯乙烯类化合物与液溴的物质的量之比为1～2。
上述步骤中，所述的催化剂用量为三硝基双二苯乙烯类化合物物质的量的10％。
与现有技术相比，具有的优点是：(1)合成了三硝基双二苯乙烯类化合物的溴化产物，(2)从结构上看，该化合物外围每个苯环上含有一个溴原子，中心苯环与另外二个苯环分别以共轭双键相连，对称性好，且大大提高了其稳定性(3)从应用上看，该化合物可用于阻燃剂、杀虫剂等。
下面结合附图对本发明作进一步详细描述。
附图说明
图1本发明实施例1产物1，3-二(2-溴苯乙烯基)-2，4，6-三硝基苯的氢核磁共振图谱，横坐标是化学位移。
图2本发明实施例1产物1，3-二(2-溴苯乙烯基)-2，4，6-三硝基苯的碳核磁共振图谱，横坐标是化学位移。
图3本发明实施例1产物1，3-二(2-溴-4-氯苯乙烯基)-2，4，6-三硝基苯的氢核磁共振图谱，横坐标是化学位移。
图4本发明实施例1产物1，3-二(2-溴-4-氯苯乙烯基)-2，4，6-三硝基苯的碳核磁共振图谱，横坐标是化学位移。
图5本发明实施例1产物1，3-二(2-溴-4-二乙胺苯乙烯基)-2，4，6-三硝基苯的氢核磁共振图谱，横坐标是化学位移。
图6本发明实施例1产物1，3-二(2-溴-4-二乙胺苯乙烯基)-2，4，6-三硝基苯的碳核磁共振图谱，横坐标是化学位移。
具体实施方式
下面的实施实例可以使本专业技术人员更全面地理解本发明，而这些实施例不是对本发明技术方案的限制。
原料三硝基双二苯乙烯类化合物的制备
将2，4，6-三硝基间二甲苯(0.24g)、取代苯甲醛(0.27g)、哌啶(1mL)、苯(40mL)加入到反应器中，在100℃下回流，反应10h,蒸去部分溶剂，过滤，用苯和乙醇先后洗涤，烘干得0.4g橘黄色固体。
实施实例1
将1，3-二苯乙烯基-2，4，6-三硝基苯(0.48g)、液溴(0.32g)、H-Beta分子筛(0.05g)、氧化锌(0.05g)和二氯甲烷(10mL)加入反应器中，常温下反应24h，过滤，萃取，旋蒸得到橘黄色的粗产品0.61g，用丙酮和乙醇进行重结晶，得到橘黄色的纯产品0.59g，熔点为167-169℃，产率为96.7％。其氢谱和碳谱见图1和2。
IR(KBr,ν,cm-1):3089,1629,1603,1587,1452,1342,700；1HNMR(300MHz,CDCl3),δ8.46(s,1H),7.49-7.47(m,8H),5.93(d,J＝10.8Hz,2H),5.29(d,J＝11.1Hz,2H)；13CNMR(75MHz,CDCl3),δ149.38,137.83,137.53,129.87,129.14,128.06,127.87,124.52,123.12.
实施实例2
将1，3-二(4-氯苯乙烯基)-2，4，6-三硝基苯(0.55g)、液溴(0.32g)、H-Beta分子筛(0.05g)、氧化锌(0.05g)和二氯甲烷(10mL)加入反应器中，常温下反应24h，过滤，萃取，旋蒸得到橘黄色的粗产品0.68g，用丙酮和乙醇进行重结晶，得到橘黄色的纯产品0.65g，熔点为157-158℃，产率为95.6％。其氢谱和碳谱见图3和4。
IR(KBr,ν,cm-1):3094,1636,1587,1543,1333,971；1HNMR(300MHz,CDCl3),δ8.77(s,1H),7.45-7.38(m,6H),7.20(d,J＝16.5Hz,2H),6.86(d,J＝16.5Hz,2H)；13CNMR(75MHz,CDCl3),δ146.59,142.74,137.57,133.19,131.30,130.82,129.16,128.59,121.71,119.00,118.78,116.24.
实施实例3
将1，3-二(4-二乙胺苯乙烯基)-2，4，6-三硝基苯(0.57g)、液溴(0.32g)、H-Beta分子筛(0.05g)、氧化锌(0.05g)和二氯甲烷(10mL)加入反应器中，常温下反应24h，过滤，萃取，旋蒸得到橘黄色的粗产品0.70g，用丙酮和乙醇进行重结晶，得到紫红色的纯产品0.67g，熔点为140-141℃，产率为95.7％。其氢谱和碳谱见图5和6。
IR(KBr,ν,cm-1):3087,1691,1629,1583,1537,1331,970；1HNMR(300MHz,CDCl3),δ8.72(s,1H),7.70(d,J＝1.8Hz,2H),7.40-7.37(m,2H),7.09-7.03(m,4H),6.79(d,J＝16.5),3.88(s,12H)；13CNMR(75MHz,CDCl3),δ154.56,153.24,146.29,137.25,132.94,130.08,127.32,120.11,118.92,118.36,114.55,43.79.
本发明所涉及的三硝基双二苯乙烯类化合物的溴化产物，外围每个苯环上含有一个溴原子，且对称性好，可用于阻燃剂、杀虫剂等，对于稳定性有了部分提高，而且中心苯环与另外二个苯环以二个共轭双键相连，大大提高了其稳定性。
Claims (6)
1.一种三硝基双二苯乙烯类化合物的溴化产物，其特征在于，具有以下结构：
其中，R为-H、-Cl、-N(CH3)2。
2.如权利要求1所述的三硝基双二苯乙烯类化合物的溴化产物的合成方法，其特征在于，包括以下步骤：
将三硝基双二苯乙烯类化合物、液溴、催化剂加入到反应器中，以二氯甲烷做溶剂，在常温下反应完成后，过滤，用饱和碳酸钠溶液中和滤液，二氯甲烷萃取，旋蒸，烘干得到溴化产物。
3.如权利要求1所述的三硝基双二苯乙烯类化合物的溴化产物的合成方法，其特征在于，所述的催化剂选用H-Beta或HZSM-5和氧化锌、氧化铋、氧化铁、氧化钛中任意一种的组合。
4.如权利要求1所述的三硝基双二苯乙烯类化合物的溴化产物的合成方法，其特征在于，所述的三硝基双二苯乙烯类化合物与液溴的物质的量之比为1~2。
5.如权利要求1所述的三硝基双二苯乙烯类化合物的溴化产物的合成方法，其特征在于，所述的催化剂用量为三硝基双二苯乙烯类化合物物质的量的10%。
6.如权利要求1所述的三硝基双二苯乙烯类化合物的溴化产物的合成方法，其特征在于，三硝基双二苯乙烯类化合物结构为：
其中，R为-H、-Cl、-N(CH3)2。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013049364A1 (en) * | 2011-09-27 | 2013-04-04 | The Trustees Of Columbia University In The City Of New York | Resveratrol-based compounds |
| CN104016868A (zh) * | 2014-04-03 | 2014-09-03 | 南京理工大学 | 含氯的2,4,6-三硝基-1，3-二苯乙烯基苯衍生物、制备及其应用 |
| CN105037165A (zh) * | 2015-07-02 | 2015-11-11 | 江苏新淮河医药科技有限公司 | 1，3-二（2-溴-5-甲氧基苯乙烯基）-2，4，6-三硝基苯化合物及其制备方法 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013049364A1 (en) * | 2011-09-27 | 2013-04-04 | The Trustees Of Columbia University In The City Of New York | Resveratrol-based compounds |
| CN104016868A (zh) * | 2014-04-03 | 2014-09-03 | 南京理工大学 | 含氯的2,4,6-三硝基-1，3-二苯乙烯基苯衍生物、制备及其应用 |
| CN105037165A (zh) * | 2015-07-02 | 2015-11-11 | 江苏新淮河医药科技有限公司 | 1，3-二（2-溴-5-甲氧基苯乙烯基）-2，4，6-三硝基苯化合物及其制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| 孙荣康等: "多硝基茵合成的研究", 《兵工学报》 * |
| 彭新华等: "多硝基茋合成的研究", 《华东工学院学报》 * |
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