酰胺类固化剂的合成工艺研究及反应机理探索
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摘要
β-羟烷基酰胺类固化剂具有无毒、高效、经济和环保的特点,被广泛应用于含有羧基或酸酐的聚酯粉末涂料。
首先,本文在物料比接近化学计量系数比的基础上,通过单因素实验、正交实验和助剂的选择,研究了N,N,N′,N′-四(β-羟乙基)已二酰胺的合成和工艺,在熔点符合要求的前提下,得率可达90.7%。并研究了两步法合成和梯度降温合成,用~1HNMR鉴定副产物的结构以便探索反应机理。
其次,采用合成N,N,N′,N′-四(β-羟乙基)已二酰胺的类似方法首次用二乙醇胺氨解苯甲酸甲酯的方法合成了N,N-二(β-羟乙基)苯甲酰胺,并借助气相色谱研究了合成工艺,找到了最佳反应条件,在该条件下得率可达87.8%。还自行设计了连续萃取装置,用于目标产物的分离。
第三,针对N,N,N′,N′-四(β-羟乙基)已二酰胺在使用过程中的泛黄性,探索了其衍生物N,N,N′,N′-四(烯丙酰氧乙基)已二酰胺和N,N,N′,N′-四(环氧丙氧基乙基)已二酰胺的合成,拓展新用途。前者的合成尝试了丙烯酸法、丙烯酸甲酯法和丙烯酰氯法,结果表明丙烯酰氯法反应温度低,聚合程度小,收率高。后者的合成尝试了酸催化两步法和碱催化一步法,结果表明两步法没有检测到极性较小的物质生成,一步法的效果较好。
最后,合成了光固化剂N,N′-二烯丙基已二酰胺和N-烯丙基苯甲酰胺,收率均达到90%以上。
The curing agents ofβ-hydroxyalkylamides are widely used in polyesters which contain carboxyl and anhydride groups because of their non toxicity,high efficiency,economy and ecology.
Firstly,this paper focused on synthesis and technology of N,N,N',N'-tetra (β-hydroxyethyl)adipamide based on single factor experiments,orthogonal experiments and choice of auxiliaries under ratio of stoichiometric coefficient.The yield reached 90.7%with melting point meeting requirement.Moreover,two-step synthesis and gradient temperaturereducing synthesis were studied.By-product was identified by ~1HNMR in order to explore reaction mechanism.
Secondly,N,N-bis(β-hydroxyethyl)benzoylamide was synthesized first by aminolysis of methyl benzoate with diethanolamine using a method of preparing N,N,N',N'-tetra (β-hydroxyethyl)adipamide.Synthetical technology was studied with help of GC and optimal reaction condition was obtained.Under this condition,yield was about 87.8%.Liquid- liquid continuous extractor which was designed in person was used to separate target product.
Thirdly,yellowing of N,N,N',N'-tetra(β-hydroxyethyl)adipamide limits its application. In this paper,synthesis of N,N,N',N'-tetra(acryloxyethyl)adipamide(Ⅰ)and N,N,N',N'-tetra (epoxy propyloxyethyl)adipamide(Ⅱ)as its derivatives were explored to expand its new use. Methods of "acrylic acid","methyl acrylate" and "acryloyl chloride" were tried to synthesize I.Results revealed that method of acryloyl chloride had low reaction temperature and degree of polymerization which gave high yield compared to methods of acrylic acid and methyl acrylate.Two-step method under catalyst of acid and one-step method under catalyst of base were studied to prepareⅡ.Results revealed that no low polar ingredient was found in two-step method which was inferior to one-step method.
Finally,photo curing agent of N,N'-diallyladipamide and N-allyl benzoylamide were prepared both with a yield of over 90%.
首先,本文在物料比接近化学计量系数比的基础上,通过单因素实验、正交实验和助剂的选择,研究了N,N,N′,N′-四(β-羟乙基)已二酰胺的合成和工艺,在熔点符合要求的前提下,得率可达90.7%。并研究了两步法合成和梯度降温合成,用~1HNMR鉴定副产物的结构以便探索反应机理。
其次,采用合成N,N,N′,N′-四(β-羟乙基)已二酰胺的类似方法首次用二乙醇胺氨解苯甲酸甲酯的方法合成了N,N-二(β-羟乙基)苯甲酰胺,并借助气相色谱研究了合成工艺,找到了最佳反应条件,在该条件下得率可达87.8%。还自行设计了连续萃取装置,用于目标产物的分离。
第三,针对N,N,N′,N′-四(β-羟乙基)已二酰胺在使用过程中的泛黄性,探索了其衍生物N,N,N′,N′-四(烯丙酰氧乙基)已二酰胺和N,N,N′,N′-四(环氧丙氧基乙基)已二酰胺的合成,拓展新用途。前者的合成尝试了丙烯酸法、丙烯酸甲酯法和丙烯酰氯法,结果表明丙烯酰氯法反应温度低,聚合程度小,收率高。后者的合成尝试了酸催化两步法和碱催化一步法,结果表明两步法没有检测到极性较小的物质生成,一步法的效果较好。
最后,合成了光固化剂N,N′-二烯丙基已二酰胺和N-烯丙基苯甲酰胺,收率均达到90%以上。
The curing agents ofβ-hydroxyalkylamides are widely used in polyesters which contain carboxyl and anhydride groups because of their non toxicity,high efficiency,economy and ecology.
Firstly,this paper focused on synthesis and technology of N,N,N',N'-tetra (β-hydroxyethyl)adipamide based on single factor experiments,orthogonal experiments and choice of auxiliaries under ratio of stoichiometric coefficient.The yield reached 90.7%with melting point meeting requirement.Moreover,two-step synthesis and gradient temperaturereducing synthesis were studied.By-product was identified by ~1HNMR in order to explore reaction mechanism.
Secondly,N,N-bis(β-hydroxyethyl)benzoylamide was synthesized first by aminolysis of methyl benzoate with diethanolamine using a method of preparing N,N,N',N'-tetra (β-hydroxyethyl)adipamide.Synthetical technology was studied with help of GC and optimal reaction condition was obtained.Under this condition,yield was about 87.8%.Liquid- liquid continuous extractor which was designed in person was used to separate target product.
Thirdly,yellowing of N,N,N',N'-tetra(β-hydroxyethyl)adipamide limits its application. In this paper,synthesis of N,N,N',N'-tetra(acryloxyethyl)adipamide(Ⅰ)and N,N,N',N'-tetra (epoxy propyloxyethyl)adipamide(Ⅱ)as its derivatives were explored to expand its new use. Methods of "acrylic acid","methyl acrylate" and "acryloyl chloride" were tried to synthesize I.Results revealed that method of acryloyl chloride had low reaction temperature and degree of polymerization which gave high yield compared to methods of acrylic acid and methyl acrylate.Two-step method under catalyst of acid and one-step method under catalyst of base were studied to prepareⅡ.Results revealed that no low polar ingredient was found in two-step method which was inferior to one-step method.
Finally,photo curing agent of N,N'-diallyladipamide and N-allyl benzoylamide were prepared both with a yield of over 90%.
引文
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