CN113896644A - 一种利用离子液体制备N-乙基-N-（β-甲氧碳酰乙基）苯胺的方法 - Google Patents
一种利用离子液体制备N-乙基-N-（β-甲氧碳酰乙基）苯胺的方法 Download PDFInfo
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
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- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
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Abstract
本发明公开了一种利用离子液体制备N‑乙基‑N‑(ß‑甲氧碳酰乙基)苯胺的方法，属有机化学合成领域。该方法以苯胺、氯乙烷和丙烯酸甲酯为原料，以热稳定性好、难挥发、可循环使用的离子液体为催化剂和溶剂，通过取代‑Michael加成串联反应制备N‑乙基‑N‑(ß‑甲氧碳酰乙基)苯胺。该方法不使用任何有毒有害的催化剂，操作简便、后处理简单、反应条件温和、选择性好、产率高，是一种高效合成N‑乙基‑N‑(ß‑甲氧碳酰乙基)苯胺的绿色新方法。
Description
技术领域
本发明涉及一种制备N-乙基-N-(β-甲氧碳酰乙基)苯胺的方法，特别是涉及利用离子液体制备N-乙基-N-(β-甲氧碳酰乙基)苯胺的方法，属有机化学合成领域。
背景技术
N-乙基-N-(β-甲氧碳酰乙基)苯胺是合成分散染料的重要中间体，传统的合成方法有以下三种：(1)以N-乙基苯胺与丙烯酸为原料，先发生加成反应，然后再以浓硫酸为催化剂与甲醇发生酯化反应合成目标产物。该方法第二步使用浓硫酸作为催化剂，催化剂难于回收且对环境不友好；两步法合成工艺较复杂，且收率也较低。(2)以N-乙基苯胺与1-氯丙酸甲酯经缩合合成目标产物，该方法虽然工艺比较方便，但原材料较难得到，不利于工业化生产。(3)以醋酸为催化剂，对苯二酚为阻聚剂，N-乙基苯胺与丙烯酸甲酯为原料，在回流下反应16小时得到N-乙基-N-(β-甲氧碳酰乙基)苯胺。该方法使用大量醋酸作为催化剂(N-乙基苯胺:醋酸最合适摩尔比为l:1)，反应结束后需要加入氢氧化钠进行中和，产生废水，给环境带来危害。目前急需对N-乙基-N-(β-甲氧碳酰乙基)苯胺的制备方法进行改进，满足工业生产需求。
发明内容
为了解决现有技术中存在的反应条件苛刻，操作复杂，催化剂难于回收且对环境不友好等问题，本发明目的是提供一种制备N-乙基-N-(β-甲氧碳酰乙基)苯胺的新方法。
为实现本发明目的，本发明以对水和空气十分稳定的离子液体为催化剂和溶剂，以苯胺、氯乙烷、丙烯酸甲酯为原料通过取代-Michael加成串联反应来合成N-乙基-N-(β-甲氧碳酰乙基)苯胺。
具体技术方案如下：
以咪唑类或内酰胺类或季铵类阳离子与四氟化硼或六氟化磷或硫酸氢根或磷酸二氢根或对甲苯磺酸根阴离子形成的离子液体为催化剂和溶剂，以苯胺、氯乙烷、丙烯酸甲酯为原料进行反应合成N-乙基-N-(β-甲氧碳酰乙基)苯胺；反应结束后经萃取，合并有机层，旋转蒸发除去溶剂的粗产品再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺。离子液体经过处理后循环应用。
反应式如下：
本发明所述的离子液体包括：[NMPH]H2PO4、[NMPH]HSO4、[NMPH]TSOH、[HMIM]H2PO4、[HMIM]HSO4、[BMIM]HSO4、[EMIM]HSO4、[Me3NH]HSO4、[Et3NH]HSO4、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH]HSO4、[Et3NH]H2PO4、[BMIM]BF4、[BMIM]PF6、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4或[Bu2NH2]H2PO4。
本发明所述的苯胺:氯乙烷:丙烯酸甲酯的摩尔比在1:0.1～2:0.1～5。
本发明所述的苯胺与离子液体的摩尔比1:0.1～9。
本发明所述的反应温度为30℃～200℃。
本发明所述的反应时间在1～24小时。
本发明优点在于：以对水和空气十分稳定的离子液体为催化剂和溶剂,以苯胺、氯乙烷和丙烯酸甲酯为原料通过取代-Michael加成串联反应来合成N-乙基-N-(β-甲氧碳酰乙基)苯胺。与传统方法相比，该方法不使用有毒有害的酸催化剂以及助催化剂，无需在反应结束后进行中和，对环境友好；无需对反应中间体进行纯化及处理，反应过程简单，操作简便，催化剂可以循环使用；此外，苯胺、氯乙烷和丙烯酸甲酯的三组分反应通常会得到包括N-乙基-N-(β-甲氧碳酰乙基)苯胺、N-乙基苯胺、N,N-二乙基苯胺、N-甲氧基羰基乙基苯胺等在内的多种产物，而在离子液体中可以有效地抑制副产物的生成，提高目标产物N-乙基-N-(β-甲氧碳酰乙基)苯胺的选择性，利用本方法合成的N-乙基-N-(β-甲氧碳酰乙基)苯胺产率可达到85％以上。能够很好地满足工业生产需求。
具体实施方式
以下的实施案例将对本发明进行更为全面的描述。
实施例1
在反应容器中投入0.2摩尔苯胺，0.18摩尔氯乙烷，0.2摩尔丙烯酸甲酯和0.5摩尔[NMPH]HSO4离子液体，50℃搅拌反应12小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为86％；离子液体经过简单处理后，用于下一次实验。
实施例2
在反应容器中投入0.2摩尔苯胺，0.2摩尔氯乙烷，0.25摩尔丙烯酸甲酯和0.8摩尔[Me3NH]HSO4离子液体，40℃搅拌反应18小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为87％；离子液体经过简单处理后，用于下一次实验。
实施例3
在反应容器中投入1.0摩尔苯胺，1.0摩尔氯乙烷，1.25摩尔丙烯酸甲酯和2摩尔[Et3NH]HSO4离子液体，110℃搅拌反应10小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为89％；离子液体经过简单处理后，用于下一次实验。
实施例4
在反应容器中投入0.6摩尔苯胺，0.5摩尔氯乙烷，0.7摩尔丙烯酸甲酯和0.5摩尔[BMIM]HSO4离子液体，60℃搅拌反应15小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为88％；离子液体经过简单处理后，用于下一次实验。
实施例5
在反应容器中投入0.6摩尔苯胺，0.6摩尔氯乙烷，0.55摩尔丙烯酸甲酯和0.2摩尔[HMIM]HSO4离子液体，90℃搅拌反应16小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为87％；离子液体经过简单处理后，用于下一次实验。
实施例6
在反应容器中投入0.9摩尔苯胺，0.8摩尔氯乙烷，0.8摩尔丙烯酸甲酯和0.7摩尔[HMIM]H2PO4离子液体，100℃搅拌反应18小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为86％；离子液体经过简单处理后，用于下一次实验。
实施例7
在反应容器中投入0.8摩尔苯胺，0.7摩尔氯乙烷，0.6摩尔丙烯酸甲酯和0.6摩尔[EMIM]HSO4离子液体，70℃搅拌反应18小时。加入乙酸乙酯萃取，合并有机层，旋转蒸发除去溶剂得粗产品，再经柱层析分离得到N-乙基-N-(β-甲氧碳酰乙基)苯胺，反应的产率为89％；离子液体经过简单处理后，用于下一次实验。
实施例8-20
类似于实施例1，分别用[BMIM]BF4、[BMIM]PF6、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH]HSO4、[Et3NH]H2PO4、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4、[Bu2NH2]H2PO4做催化剂，在同样条件下进行反应，反应结束后得到如下结果(表一)：
表一
Claims (3)
1.一种利用离子液体制备N-乙基-N-(ß-甲氧碳酰乙基)苯胺的方法，其特征在于，在以咪唑类或内酰胺类或季铵类阳离子和四氟化硼或六氟化磷或硫酸氢根或磷酸二氢根或对甲苯磺酸根阴离子形成的离子液体为催化剂和溶剂的条件下，以苯胺、氯乙烷、丙烯酸甲酯为原料反应合成N-乙基-N-(ß-甲氧碳酰乙基)苯胺。
2.根据权利要求1所述的利用离子液体制备N-乙基-N-(ß-甲氧碳酰乙基)苯胺方法，其特征在于，所述离子液体包括[NMPH]H2PO4、[NMPH]HSO4、[NMPH]PTSA、[HMIM]H2PO4、[HMIM]HSO4、[BMIM]HSO4、[EMIM]HSO4、[Me3NH]HSO4、[Et3NH]HSO4、[Pr3NH]HSO4、[Bu3NH]HSO4、[Me2NH2]HSO4、[Et3NH]H2PO4、[Pr3NH]H2PO4、[Bu3NH]H2PO4、[Me2NH2]H2PO4、[Et2NH2]H2PO4、[Pr2NH2]H2PO4、[BMIM]BF4 、[BMIM]PF6 、[Bu2NH2]H2PO4、[MeNH3]H2PO4、[EtNH3]H2PO4、[PrNH3]H2PO4或[Bu2NH2]H2PO4。
3.根据权利要求1所述利用离子液体制备N-乙基-N-(ß-甲氧碳酰乙基)苯胺方法，其特征在于，苯胺:氯乙烷:丙烯酸甲酯的摩尔比为1:0.1～2:0.1～5；苯胺和离子液体的摩尔比为1:0.1～9。
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