铜催化的C-N偶联反应及C=N反应研究
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摘要
随着经济的发展,传统的化学工业对环境的污染越来越严重,人类与环境的矛盾在不断的激化。各种环境问题不仅威胁到人类的生存环境,更是威胁到了人类自身的发展。因而化学工业绿色化是当今世界化学界的研究主要方向。C-N交叉偶联反应是有机化学中一个重要的内容,其在化工和医药中都有着广泛的应用。传统的反应一般需要特定的催化剂和在苛刻的条件下进行反应,对于工业操作和经济上都很有局限性。芳香亚胺类化合物是医药合成极为重要的合成中间体,在工业中最常用的合成方法,是用伯胺和醛／酮／醇类通过脱水缩合反应生成亚胺,而直接通过伯胺自身偶联反应合成的较少。
使用固体高效催化剂催化C-N偶联反应,及合成亚胺是本文研究的重点。氧化铜及氧化亚铜作为一种廉价、低毒的固体催化剂,更加符合化学工业绿色化的要求。
本文研究的主要内容：
一、用不同形貌的氧化亚铜为催化剂催化碘苯与苄胺的C-N交叉偶联反应的研究,以期得到不同形貌氧化亚铜的不同晶面的催化性差异。但是由于反应产率较低,不能作为评价不同晶面催化性能差异的标准。但是为之后做类似的研究奠定了基础。
二、CuO/酸性Al203为复合催化剂,在甲苯为溶剂、氧气气氛、温度110℃、反应24 h条件下,催化苄胺及其衍生物脱氨偶联合成亚胺及芳香仲胺的脱氢氧化成亚胺。反应有较好的选择性及较高的产率,且对不同伯胺有一定的耐用性。
With development of economical, the traditional chemical industry lead to increasingly serious pollution of the environment, the conflict of human and environment is in the continuous intensification. Environmental problems have threatened the survival of the human environment, and are a threat to the development of human beings, which are reasons that why the green chemical industry is the main direction of chemical industry of the world. C-N cross-coupling reaction is an important content of organic chemistry, and medicine in chemical widely used in both. The traditional reactions have generally required specific catalysts and harsh conditions, there has limitations for both industrial and economic operation. Aromatic polyimide compounds are very important pharmaceutical intermediate synthesis, In industrial synthesis, the most commonly used method is the use of primary amines and aldehydes, alkones or alcohols by dehydration condensation reaction to imines.
The focus of this thesis are synthesis imines through C-N cross-coupling reaction and C=N reactions catalyzed by efficient solid catalysts. Copper oxide and cuprous oxide are cheap, low toxicity and solid catalysts. So using copper oxide and cuprous oxide as catalyst is in line with the requirements of the chemical industry green.
The main contents of this thesis:
1、Using different morphologies of cuprous oxide as catalysts was in the iodine benzene and benzylamines of C-N cross-coupling reaction, and we want to obtain a different catalytic activity of the different crystals faces of cuprous oxide. But low response rate can not be as evaluation standards for the unit catalytic performance. But the studies provided the foundation for the research in the future.
2、CuO/acidic Al2O3 as catalyst, toluene as solvent, oxygen atmosphere, temperature 110℃, 24h reaction as conditions of reaction, coupling reaction of benzyl amine and its derivatives through transmaination-coupling reactions and dehydrogenation-oxidation of aromatic amine were to synthesize imine. We had a good response and a high rate of productions, and durability for primary amines.
使用固体高效催化剂催化C-N偶联反应,及合成亚胺是本文研究的重点。氧化铜及氧化亚铜作为一种廉价、低毒的固体催化剂,更加符合化学工业绿色化的要求。
本文研究的主要内容：
一、用不同形貌的氧化亚铜为催化剂催化碘苯与苄胺的C-N交叉偶联反应的研究,以期得到不同形貌氧化亚铜的不同晶面的催化性差异。但是由于反应产率较低,不能作为评价不同晶面催化性能差异的标准。但是为之后做类似的研究奠定了基础。
二、CuO/酸性Al203为复合催化剂,在甲苯为溶剂、氧气气氛、温度110℃、反应24 h条件下,催化苄胺及其衍生物脱氨偶联合成亚胺及芳香仲胺的脱氢氧化成亚胺。反应有较好的选择性及较高的产率,且对不同伯胺有一定的耐用性。
With development of economical, the traditional chemical industry lead to increasingly serious pollution of the environment, the conflict of human and environment is in the continuous intensification. Environmental problems have threatened the survival of the human environment, and are a threat to the development of human beings, which are reasons that why the green chemical industry is the main direction of chemical industry of the world. C-N cross-coupling reaction is an important content of organic chemistry, and medicine in chemical widely used in both. The traditional reactions have generally required specific catalysts and harsh conditions, there has limitations for both industrial and economic operation. Aromatic polyimide compounds are very important pharmaceutical intermediate synthesis, In industrial synthesis, the most commonly used method is the use of primary amines and aldehydes, alkones or alcohols by dehydration condensation reaction to imines.
The focus of this thesis are synthesis imines through C-N cross-coupling reaction and C=N reactions catalyzed by efficient solid catalysts. Copper oxide and cuprous oxide are cheap, low toxicity and solid catalysts. So using copper oxide and cuprous oxide as catalyst is in line with the requirements of the chemical industry green.
The main contents of this thesis:
1、Using different morphologies of cuprous oxide as catalysts was in the iodine benzene and benzylamines of C-N cross-coupling reaction, and we want to obtain a different catalytic activity of the different crystals faces of cuprous oxide. But low response rate can not be as evaluation standards for the unit catalytic performance. But the studies provided the foundation for the research in the future.
2、CuO/acidic Al2O3 as catalyst, toluene as solvent, oxygen atmosphere, temperature 110℃, 24h reaction as conditions of reaction, coupling reaction of benzyl amine and its derivatives through transmaination-coupling reactions and dehydrogenation-oxidation of aromatic amine were to synthesize imine. We had a good response and a high rate of productions, and durability for primary amines.
引文
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