CN117049951A - 一种催化环己烷选择性氧化制备环己酮的方法 - Google Patents
一种催化环己烷选择性氧化制备环己酮的方法 Download PDFInfo
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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Abstract
本发明提供了一种催化环己烷选择性氧化制备环己酮的方法,所述方法将原料与自由基引发剂、催化剂分散在溶剂中,以空气中的氧气为氧化剂,在反应温度为70~75℃、反应压力为1.0~2.0MPa的条件下反应5~12h,催化氧化环己烷制得环己酮;所述原料为环己烷;所述催化剂为如下通式(Ι)结构的四苯基铜卟啉化合物;所述催化剂用量为原料的摩尔量的0.001~0.005%,所述自由基引发剂的用量为原料的摩尔量的5~10mol%。本发明采用四苯基卟啉铜为催化剂,以空气为氧化剂直接一步氧化环己烷,反应原料的转化率和产物的选择性高;且反应条件温和(70~75℃、1.0~2.0MPa),催化剂用量小,仅需相对于原料的ppm级别即可。
Description
技术领域
本发明涉及烃类化合物催化氧化的技术领域,更具体地,涉及一种催化环己烷选择性氧化制备环己酮的方法。
背景技术
烃类化合物由于C-H键能较大、活化困难,使得其官能团化不易实现。目前工业上的环己烷氧化制备KA油(环己醇/酮)的工艺,单程转化率仅4%,且反应温度较高(>150℃)。
按照催化剂的性质,催化氧化工艺可分非均相催化和均相催化两大类。非均相催化体系的优势是催化剂容易回收分离,但是催化活性一般较低。例如,中国专利CN101822990A、CN101862660A等公开了使用负载型催化剂催化环己烷氧化制备环己酮的方法,环己烷转化率仅10%,环己醇和环己酮总选择性可达到90%以上,但是需要使用贵金属掺杂制备催化剂,成本较高,且反应温度普遍在120℃以上,反应能耗高。
均相催化体系的优势是催化活性较高,但是对于反应条件一般要求较高,需要昂贵的添加剂。例如,中国专利CN100402477C公开了一种金属卟啉催化环烷烃氧化的,环己烷转化率可达到15%,环己酮和环己醇的总选择性在80%以上,但是反应温度过高需要在120℃以上进行,高温条件下金属卟啉容易聚合失活;中国专利CN110483244A公开了一种催化芳香烃与环烷烃液相选择性氧化的方法,使用的双核铜卟啉化合物作为催化剂,效果虽然显著但是催化剂合成方法较为繁琐,成本较高。
因此,开发一种反应条件温和、绿色、高效的催化氧化环己烷选择性氧化的工艺方法具有重要的现实意义和应用前景。
发明内容
本发明的目的在于提供一种反应条件温和、绿色、高效的催化环己烷选择性氧化制备环己酮的方法。
为解决上述技术问题,本发明采用的技术方案是:
一种催化环己烷选择性氧化制备环己酮的方法,将原料与自由基引发剂、催化剂分散在溶剂中,以空气中的氧气为氧化剂,在反应温度为70~75℃、反应压力为1.0~2.0MPa的条件下反应5~12h,催化氧化环己烷制得环己酮;所述原料为环己烷;
所述催化剂为如下通式(Ι)结构的四苯基卟啉铜化合物;
所述催化剂用量为原料的摩尔量的0.001~0.005%,所述自由基引发剂的用量为原料的摩尔量的5~10%
本发明所述原料为环己烷。
当本发明所述原料为环己烷时;所述溶剂为乙腈;所述反应压力为1.0~2.0MPa,所述反应温度为70~75℃,反应时间为5~12h。
本发明所述自由基引发剂为N-羟基邻苯二甲酰胺(NHPI)或N-羟基邻苯二甲酰亚胺衍生物。
与现有技术相比,本发明的有益效果是:
本发明采用四苯基卟啉铜为催化剂,以空气为氧化剂直接一步氧化环己烷,反应原料的转化率和产物的选择性高;且反应条件温和(70~75℃、1.0~2.0MPa),催化剂用量小,仅需相对于原料的ppm级别即可。
具体实施方式
下面结合具体实施方式对本发明作进一步的说明。实施例及对比例中的原料均可通过市售得到。
本发明所使用的四苯基铜卟啉催化剂的合成方法,步骤如下:
将吡咯、苯甲醛加入到丙酸中,将混合物回流l h,室温冷却后,用甲醇以及热水洗涤并过滤悬浮液,得到卟啉。将卟啉溶解于氯仿中,回流1h,再加入饱和的甲醇醋酸铜溶液进行反应,然后进一步洗涤并用都会除去未反应的试剂,得到四苯基卟啉铜,其结构如下通式(Ι)所示:
所制备的四苯基卟啉铜对比之前合成的双核铜卟啉化合物合成步骤简单,且反应效果也好。
实施例1
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.001%,自由基用量为环己烷的摩尔量的10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为55.2%,环己酮选择性为89.2%
实施例2
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.002%,自由基用量为环己烷的摩尔量的10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为61.4%,环己酮选择性为85.3%
实施例3
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在70℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.003%,自由基用量为环己烷的摩尔量10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为62.2%,环己酮选择性为83.5%
实施例4
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.003%,自由基用量为环己烷的摩尔量的10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为65.2%,环己酮选择性为82.2%
实施例5
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.004%,自由基用量为环己烷的摩尔量的10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为70.8%,环己酮选择性为78.9%
实施例6
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.005%,自由基用量为环己烷的摩尔量5%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为68.9%,环己酮选择性为79.3%
实施例7
在高压反应釜中,加入含有催化剂具有通式(Ⅰ)结构的四苯基卟啉铜的乙腈,加入自由基引发剂NHPI和环己烷,充入2.0MPa的空气,在75℃的条件下反应8h;其中,催化剂为具有通式(Ι)结构的四苯基铜卟啉,原料为环己烷,催化剂用量为原料的摩尔量的0.005%,自由基用量为环己烷的摩尔量10%。反应完毕,冰水冷却至室温,取样进行气相色谱分析。测得环己烷转化率为74.3%,环己酮选择性为75.8%
检测
对以上实施例和对比例的反应进行色谱检测,测试方法为:反应结束后,冷却解除压力,吸取并过滤反应液,使用具FID检测器及InertCap Pure-WAX极性毛细管色谱柱的气相色谱进行在线检测,根据萘(即内标)、相应醛与酮氧化产物的峰面积,结合标准曲线计算得到产物选择性与底物转化率。
附图说明
图1是实施案例5提供的气相色谱图
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本发明权利要求的保护范围之内。
Claims (3)
1.一种催化环己烷选择性氧化制备环己酮的方法,其特征在于,将原料与自由基引发剂、催化剂分散在溶剂中,以空气中的氧气为氧化剂,在反应温度为70~75℃、反应压力为1.0~2.0MPa的条件下反应5~12h,催化氧化环己烷制得环己酮;所述原料为环己烷;
所述催化剂为如下通式(Ι)结构的四苯基卟啉铜化合物;
所述催化剂用量为原料的摩尔量的0.001~0.005%,所述自由基引发剂的用量为原料的摩尔量的5~10%。
2.根据权利要求1所述的制备方法,其特征在于,所述原料为环己烷,所述溶剂为乙腈;反应压力为1.0~2.0MPa,所述温度为70~75℃,反应时间为7h。
3.根据权利要求1所述的制备方法,其特征在于,所述自由基引发剂为N-羟基邻苯二甲酰胺或N-羟基邻苯二甲酰亚胺衍生物。
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