CN107954913A - 一种卤代含氮不饱和环烃的制备方法 - Google Patents

一种卤代含氮不饱和环烃的制备方法 Download PDF

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CN107954913A
CN107954913A CN201711391182.XA CN201711391182A CN107954913A CN 107954913 A CN107954913 A CN 107954913A CN 201711391182 A CN201711391182 A CN 201711391182A CN 107954913 A CN107954913 A CN 107954913A
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cyclic hydrocarbon
unsaturated cyclic
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鞠有国
赵奔腾
王泽武
杨寒华
张兆元
刘建
公方薪
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Shandong Tianxin Chemical Co Ltd
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Abstract

本发明公开了一种卤代含氮不饱和环烃的制备方法，步骤为：（1）将含氮不饱和环烃溶解于盐酸或氢溴酸中，加入氧化剂，使反应体系进行卤代反应，反应过程中定时取样检测，当检测到目标产物一卤化物的质量占比为反应体系内的总有机物的70%‑95%时，向反应体系内加入终止剂终止反应，便得到含有含氮不饱和环烃的料液；（2）向料液加入有机溶剂进行萃取，萃取后得到有机相，将有机相降温使其析出固体物或蒸馏有机相除去溶剂得到液体产物，所得固体物或液体产物为卤代含氮不饱和环烃。该方法很好的解决了含氮不饱和环烃过卤代化反应的问题。

Description

一种卤代含氮不饱和环烃的制备方法
技术领域
本发明涉及一种卤代含氮不饱和环烃的制备方法。
背景技术
卤代含氮不饱和环烃是重要的精细化工中间体，主要用于制备农药、医药和染料等精细化学品。具有代表性的中间体如2-氯-3-氨基吡啶、2-氯嘧啶、2-氯咪唑等。
含氮不饱和环烃的卤代反应有选择性，并且会出现过卤代反应的情况，已有报道中烷烃通过加入催化剂，改变卤代反应的选择性，公开号为CN103304367A的中国专利中，使用纳米贵金属/半导体表面等离子体符合材料光催化剂，以可见光或阳光为反应所需能量来源，在烷烃上进行选择性卤代。此方法使用昂贵的催化剂，并且难以实现较高转化率的选择性卤代，仍会存在过卤代的情况。含氮不饱和环烃的卤代合成方法未见报道。
因此，寻找一种控制高转化率卤代目标产物，防止过卤代化反应的卤代含氮不饱和环烃的合成控制方法是当前要解决的主要问题。
发明内容
本发明的目的是提供一种卤代含氮不饱和环烃的制备方法；为了实现上述发明目的，本发明所提供的卤代含氮不饱和环烃的制备方法包括以下步骤：
（1）将含氮不饱和环烃溶解于盐酸或氢溴酸中，加入氧化剂，使反应体系进行卤代反应，反应过程中定时取样检测，当检测到目标产物一卤化物的质量占比为反应体系内的总有机物的70%-95%时，向反应体系内加入终止剂终止反应，便得到含有含氮不饱和环烃的料液；
（2）向料液加入有机溶剂进行萃取，萃取后得到有机相，将有机相降温使其析出固体物或蒸馏有机相除去溶剂得到液体产物，所得固体物或液体产物为卤代含氮不饱和环烃。
所述含氮不饱和环烃所含的碳原子个数为3-6，所含的氮原子个数为1-2。
所述步骤（1）中含氮不饱和环烃可含有侧链基团，侧链基团为氨基、甲基、甲氧基或氰基。
所述氯化氢或溴化氢与含氮不饱和环烃的摩尔比为5-15：1，氧化剂与含氮不饱和环烃的摩尔比为0.4-1.2：1，终止剂与含氮不饱和环烃的摩尔比为0.2-2：1。
所述氧化剂为过氧化氢、高锰酸钾、锰酸钾、重铬酸钾或铬酸钾的水溶液的一种或几种。
所述终止剂为氧化亚铜、氯化亚铜、溴化亚铜、硫酸亚铜、氧化亚铁、氯化亚铁、溴化亚铁、硫酸亚铁、氧化亚锡、氯化亚锡、溴化亚锡或硫酸亚锡的一种或几种。
所述有机溶剂为甲苯、氯苯、二氯甲烷或三氯甲烷。
本发明步骤（1）中进行的是氧化卤代反应，在含氮不饱和环烃的环上引入一个氯或一个溴，但在目标产物一卤代含氮不饱和环烃产生的过程中，一卤代含氮不饱和环烃会同步发生副反应，生成多卤代含氮不饱和环烃，多卤代副反应反应速度比一卤代主反应反应速度慢，因此，氧化卤代反应的规律是，随着原料的逐渐减少，一卤代含氮不饱和环烃的产率先增加后降低再稳定，多卤代含氮不饱和环烃先逐渐增加再稳定，为了提高最终产品的收率，在氧化卤代反应的过程中，就需要控制反应终点，在一卤代含氮不饱和环烃的产率达到最高点时终止反应。
本发明步骤（1）在温度0-30℃和搅拌下，滴加氧化剂水溶液，氧化剂水溶液滴加完毕后，一般经过0.5-5小时就可使反应充分，反应过程定时取样用高效液相色谱仪进行检测，当检测到目标产物即一卤化物的质量为反应体系（料液）中的总有机物质量的70%-95%时，加入终止剂，将未完全反应的氧化剂还原，终止反应，防止过卤代化反应。
实际反应过程中卤代试剂配比如果不过量，就会有导致原料不能完全反应，原料残留，如果过量，卤代反应会向过卤代化反应趋势进行，且较难将反应控制在最高转化率的反应点，最后导致多卤代副反应产物增多，既影响反应有效转化率，又会增大产品和副产品的分离难度。本发明方法的优点在于：通过检测确定目标产物最高转化点，在最高转化点加入终止剂终止反应，使目标产物维持在最高转化点，很好的解决了含氮不饱和环烃过卤代化反应的问题。
具体实施方式
下面通过实施例进一步说明本发明的技术方案，这些实施例仅是用来详细展现本发明的技术构思及其可实施性，并不是对本发明保护范围的限制，利用本发明技术构思做出的等效替换和变通仍然在本发明的保护范围之内。
实施例1
（1）将吡咯6.71g（0.1mol）溶解于50.0%的氢溴酸80.90g(含溴化氢0.5mol)中，搅拌状态下，控制温度0-10℃，滴加25.0%的高锰酸钾溶液30.34g，滴加完毕，控制反应温度0-10℃使体系进行溴代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的2-溴吡咯的质量占反应体系内总有机物质量的85.0%时，加入氧化亚铜2.86g（0.02mol）终止反应，得到含有2-溴吡咯的料液；
（2）向料液中加入甲苯146.0g，搅拌萃取2小时，静置分层1小时，取有机相即2-溴吡咯的甲苯溶液进行精馏，除去溶剂后得到的11.35g液体产物为2-溴吡咯，经计算，收率为75%，经测定，主含为96.5%。
实施例2
（1）将吡唑6.81g（0.1mol）溶解于50.0%的氢溴酸161.80g(含溴化氢1.0mol)中，搅拌状态下，控制温度5-15℃，滴加25.0%的重铬酸钾溶液47.07g，滴加完毕，控制反应温度5-15℃使反应体系进行溴代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的3-溴吡唑的质量占反应体系内总有机物质量的93.0%时，加入氧化亚铁4.31g（0.06mol）终止反应，得到含有3-溴吡唑的料液；
（2）向料液中加入氯苯73.5g，搅拌萃取2小时，静置分层1小时，取有机相并使之降温至-15℃至-5℃，使固体物从有机相中充分析出，所得12.20g固体物为3-溴吡唑，经计算，收率为83%，经测定，主含为98.5%。
实施例3
（1）将3-甲氧基吡啶10.91g（0.1mol）溶解于30.0%的盐酸121.53g(含氯化氢1.0mol)中，搅拌状态下，控制温度0-15℃，滴加25.0%的锰酸钾溶液11.83g，滴加完毕，控制反应温度0-15℃使反应体系进行氯代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的2-氯-3-甲氧基吡啶的质量占反应体系内总有机物质量的80.5%时，加入氯化亚锡11.36g（0.06mol）终止反应，得到含2-氯-3-甲氧基吡啶的料液；
（2）反应料液加入二氯甲烷71.8g，搅拌萃取2小时，静置分层1小时，取有机相并使之降温至-15℃至-5℃，使固体物从有机相中充分析出，所得10.20g固体物为2-氯-3-甲氧基吡啶，经计算，收率为71%，经测定，主含为98.0%。
实施例4
（1）将3-氨基吡啶9.41g（0.1mol）溶解于30.0%的盐酸60.77g(含氯化氢0.5mol)中，搅拌状态下，控制温度0-15℃，滴加25.0%的过氧化氢溶液16.32g，滴加完毕，控制反应温度0-15℃使反应体系进行氯代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的2-氯-3-氨基吡啶的质量占反应体系内总有机物质量的85.5%时，加入氯化亚铜19.8g（0.20mol）终止反应，得到含2-氯-3-氨基吡啶的料液；
（2）向料液中加入三氯甲烷64.28g，搅拌萃取2小时，静置分层1小时，取有机相并使之降温至-15℃至-5℃，使固体物从有机相中充分析出，所得9.96g固体物为2-氯-3-氨基吡啶，经计算，收率为77.5%，经测定，主含为98.2%。
实施例5
（1）将3-氰基吡啶10.41g（0.1mol）溶解于30.0%的盐酸182.30g(含氯化氢1.5mol)中，搅拌状态下，控制温度0-15℃，滴加25.0%的铬酸钾溶液62.14g，滴加完毕，控制反应温度0-15℃使反应体系进行氯代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的2-氯-3-氰基吡啶的质量占反应体系内总有机物质量的81.5%时，加入氯化亚铁5.07g（0.04mol）终止反应，得到含2-氯-3-氰基吡啶的料液；
（2）向料液中加入甲苯138.56g，搅拌萃取2小时，静置分层1小时，取有机相并使之降温至-15℃至-5℃，使固体物从有机相中充分析出，所得9.77g 固体物为2-氯-3-氰基吡啶，经计算，收率为70.5%，经测定，主含为97.2%。
实施例6
（1）将2-甲基吡嗪9.41g（0.1mol）溶解于30.0%的盐酸182.30g g(含氯化氢1.5mol)中，搅拌状态下，控制温度0-15℃，滴加25.0%的过氧化氢溶液16.32g，滴加完毕，控制反应温度0-15℃使反应体系进行氯代反应，反应过程中定时取样，用高效液相色谱仪检测，当检测到反应体系内的2-甲基-3-氯吡嗪的质量占反应体系内总有机物质量的73.5%时，加入溴化亚铜17.21g（0.12mol）终止反应，得到含2-甲基-3-氯吡嗪的料液；
（2）向料液加入二氯甲烷63.78g，搅拌萃取2小时，静置分层1小时，取有机相并使之降温至-15℃至-5℃，使固体物从有机相中充分析出，所得固定物8.36g为2-甲基-3-氯吡嗪，经计算，收率为65.5%，经测定，主含为97.8%。
上述实施例中，目标产物含量通过液相色谱测定（外标法）。
上述实施例只选取了碳原子个数为3-6、氮原子个数为1-2的含氮不饱和环烃中的一部分以及含侧链基团的一部分物质为代表来说明本发明的可实施性，并不是把本发明的保护范围限制在实施例中所列举的含氮不饱和环烃上。除上述实施例列举的含氮不饱和环烃外，本领域技术人员根据本发明的教导，选取带氨基、甲基、甲氧基或氰基的吡咯，带氨基、甲基、甲氧基或氰基的吡唑，吡啶及带甲基的吡啶，咪唑及带氨基、甲基、甲氧基或氰基的咪唑，哒嗪以及带氨基、甲基、甲氧基或氰基的哒嗪，嘧啶及带氨基、甲基、甲氧基或氰基的嘧啶，吡嗪及带氨基、甲氧基或氰基的吡嗪，氮杂䓬及带氨基、甲基、甲氧基或氰基的氮杂䓬，仍能实现本发明；只是为节约篇幅，而不再一一举例赘述。
含3-6个碳原子、含1-2个氮原子且不含侧链基团的含氮不饱和环烃包括下列八种物质：吡咯（含4个碳原子、含1个氮原子）、吡唑（含3个碳原子、含2个氮原子）、咪唑（含3个碳原子、含2个氮原子）、吡啶（含5个碳原子、含1个氮原子）、哒嗪（含4个碳原子、含2个氮原子）、嘧啶（含4个碳原子、含2个氮原子）、吡嗪（含4个碳原子、含2个氮原子）和氮杂䓬（含6个碳原子、含1个氮原子），结构式分别如下式1至式8所示：
。

Claims (7)

1.一种卤代含氮不饱和环烃的制备方法，其特征在于包括以下工艺步骤：
（1）将含氮不饱和环烃溶解于盐酸或氢溴酸中，加入氧化剂，使反应体系进行卤代反应，反应过程中定时取样检测，当检测到目标产物一卤化物的质量占比为反应体系内的总有机物的70%-95%时，向反应体系内加入终止剂终止反应，便得到含有含氮不饱和环烃的料液；
（2）向料液加入有机溶剂进行萃取，萃取后得到有机相，将有机相降温使其析出固体物或蒸馏有机相除去溶剂得到液体产物，所得固体物或液体产物为卤代含氮不饱和环烃。
2.根据权利要求1所述的卤代含氮不饱和环烃的合成控制方法，其特征在于所述含氮不饱和环烃所含的碳原子个数为3-6，所含的氮原子个数为1-2。
3.根据权利要求1或2所述的卤代含氮不饱和环烃的制备方法，其特征在于所述含氮不饱和环烃可含有侧链基团，所述侧链基团为氨基、甲基、甲氧基或氰基。
4.根据权利要求1所述的卤代含氮不饱和环烃的制备方法，其特征在于所述氯化氢或溴化氢与含氮不饱和环烃的摩尔比为5-15：1，氧化剂与含氮不饱和环烃的摩尔比为0.4-1.2：1，终止剂与含氮不饱和环烃的摩尔比为0.2-2：1。
5.根据权利要求1所述的卤代含氮不饱和环烃的制备方法，其特征在于所述氧化剂为过氧化氢、高锰酸钾、锰酸钾、重铬酸钾或铬酸钾的水溶液的一种或几种。
6.根据权利要求1所述的卤代含氮不饱和环烃的制备方法，其特征在于所述终止剂为氧化亚铜、氯化亚铜、溴化亚铜、硫酸亚铜、氧化亚铁、氯化亚铁、溴化亚铁、硫酸亚铁、氧化亚锡、氯化亚锡、溴化亚锡或硫酸亚锡的一种或几种。
7.根据权利要求1所述的卤代含氮不饱和环烃的制备方法，其特征在于所述有机溶剂为甲苯、氯苯、二氯甲烷或三氯甲烷。
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