海因衍生物与5-氯水杨酸的合成研究
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摘要
绿色化学、清洁生产是有效防止工业污染,实现工业可持续发展的战略性措施,也是实现经济效益、环境效益和社会效益相统一的重要生产手段。
对海因衍生物和5-氯水杨酸的应用、合成路线作了详细的文献综述,遵循绿色化学原理研发5-溴乙基海因和5-氯水杨酸的合成工艺。
在研究、比较分别以氰基乙酸乙酯与丙二酸二乙酯为原料合成5-溴乙基海因合成路线的基础上,确定了一条改进的以丙二酸二乙酯为原料,经缩合、氨解、环合和开环4步反应来制备5-溴乙基海因的技术路线。探讨了反应溶剂、反应时间、物料比及催化剂等因素对反应的影响,明确各因素的相互关系。反应总收率为64.5%。此新合成工艺缩短了反应步骤,收率高;避免了使用传统工艺所需的溴素、醇钠,减少了对环境的污染,降低了操作的危险性,符合绿色化学的理念。
确定了2,5-二氯甲苯转化为5-氯水杨酸的技术路线:经光氯化、催化水解、乌尔曼反应和酸化4步反应。探讨了各反应的影响因素,得到了一条清洁的合成路线,反应总收率为80%。重点研究了适合乌尔曼反应的催化剂、催化体系、反应条件。本技术路线成功实现了把经济价值相对较低的2,5-二氯甲苯转化为高附加值的5-氯水杨酸的目的。
Green Chemistry, Cleaner Production(CP) are stratagems which can prevent the industry pollution effecively and realize the sustainabe industry development. Furthermore, the CP is an important means to realize the economy, environment and society benefit.
The applications, synthetic routes of hydantoin derivatives and 5-chlorosaclicylic acid were summarized in this paper. The synthetic procedures of 5-chlorosacilicylic acid and 5-bromoethyhydatoin was studied under the guidance of Green Chemistry.
The synthesis of 5-bromoethylhydantoin from ethyl cyanoacetate and ethyl malonate respectively was studied. Then an improvmented synthetic process was founed: Ethyl malonate as the start material, via condensation, ammonolysis, hoffmann rearrangement-cyclization and ring-opening to syntheis the product. Total yield was 64.5%. The effects of reacion solvent, reactant ratio, reacion time and catalyst were researched. This improvmented route avoided utilizing bromine and sodium alkoxide which were used in the original process, reduced toxicity and pollution, provided a higher yield and met the demand of Green chemistry.
The synthetic route of 2,5-dichlorotoluene to the valuabe downstream product, 5-chlorosaclicylic acid, was chosen: via photochlorination, catalytic hydrolysis and Ullmann reaction to the product. The factors influencing all the reaction, especially, the Ullmann reaction’s catalyst and the Ullmann reaction’s catalyst systerm were studied. Finally, 5-chlorosaclicylic acid was obtained with a yield of 80% from a low economic value product, 2,5-dichlorotoluene.
对海因衍生物和5-氯水杨酸的应用、合成路线作了详细的文献综述,遵循绿色化学原理研发5-溴乙基海因和5-氯水杨酸的合成工艺。
在研究、比较分别以氰基乙酸乙酯与丙二酸二乙酯为原料合成5-溴乙基海因合成路线的基础上,确定了一条改进的以丙二酸二乙酯为原料,经缩合、氨解、环合和开环4步反应来制备5-溴乙基海因的技术路线。探讨了反应溶剂、反应时间、物料比及催化剂等因素对反应的影响,明确各因素的相互关系。反应总收率为64.5%。此新合成工艺缩短了反应步骤,收率高;避免了使用传统工艺所需的溴素、醇钠,减少了对环境的污染,降低了操作的危险性,符合绿色化学的理念。
确定了2,5-二氯甲苯转化为5-氯水杨酸的技术路线:经光氯化、催化水解、乌尔曼反应和酸化4步反应。探讨了各反应的影响因素,得到了一条清洁的合成路线,反应总收率为80%。重点研究了适合乌尔曼反应的催化剂、催化体系、反应条件。本技术路线成功实现了把经济价值相对较低的2,5-二氯甲苯转化为高附加值的5-氯水杨酸的目的。
Green Chemistry, Cleaner Production(CP) are stratagems which can prevent the industry pollution effecively and realize the sustainabe industry development. Furthermore, the CP is an important means to realize the economy, environment and society benefit.
The applications, synthetic routes of hydantoin derivatives and 5-chlorosaclicylic acid were summarized in this paper. The synthetic procedures of 5-chlorosacilicylic acid and 5-bromoethyhydatoin was studied under the guidance of Green Chemistry.
The synthesis of 5-bromoethylhydantoin from ethyl cyanoacetate and ethyl malonate respectively was studied. Then an improvmented synthetic process was founed: Ethyl malonate as the start material, via condensation, ammonolysis, hoffmann rearrangement-cyclization and ring-opening to syntheis the product. Total yield was 64.5%. The effects of reacion solvent, reactant ratio, reacion time and catalyst were researched. This improvmented route avoided utilizing bromine and sodium alkoxide which were used in the original process, reduced toxicity and pollution, provided a higher yield and met the demand of Green chemistry.
The synthetic route of 2,5-dichlorotoluene to the valuabe downstream product, 5-chlorosaclicylic acid, was chosen: via photochlorination, catalytic hydrolysis and Ullmann reaction to the product. The factors influencing all the reaction, especially, the Ullmann reaction’s catalyst and the Ullmann reaction’s catalyst systerm were studied. Finally, 5-chlorosaclicylic acid was obtained with a yield of 80% from a low economic value product, 2,5-dichlorotoluene.
引文
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