氟代苯甲醛的合成研究
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摘要
氟代苯甲醛是制造医药、农药、香料、染料等多种精细化学产品的中间体,在医药、农药合成中,由于氟原子的引入可以提高生物活性,使药效增强、副作用降低。目前,氟代芳香醛的应用领域不断扩大。本文分别用氯化水解法和氧气液相氧化法制备对氟苯甲醛,探索了提高原料利用率、减少中间过程副产物、环境友好的绿色化路线。
氯化水解法合成对氟苯甲醛,探讨了溶剂、催化剂等反应条件对实验结果的影响。其中乌洛托品法水解氯化混合液制备对氟苯甲醛,反应条件:n(对氟氯苄):n(乌洛托品)=1:4,m(氯化液):m(乙醇)=1:1.1,收率为80.1%;对氟二氯苄在乙醇作用下水解制备对氟苯甲醛,最佳条件V(对氟二氯苄):V(乙醇)=1:5收率为95.2%;对氟氯苄通过水解、氧化制备对氟苯甲醛,当(对氟苯甲醇):n(H_2O_2)=1:1.3,催化剂n(钨酸钠):n(水杨酸)=1:1,收率为78.4%。
氧气液相氧化法合成了对氟苯甲醛,探讨了溶剂、催化剂、氧源、温度等条件对反应结果的影响。通过研究发现,V(对氟甲苯):v(冰醋酸)=1:3,Co/Mn/Br混合物作催化剂,n(Co(OAc)_2.4H_2O):n(Mn(OAc)_2.4H_2O):n(KBr)=1:2:3,在反应温度90-95℃,氧气流量为2.4mL/min时,对氟甲苯的转化率为23.5%,对氟苯甲醛的选择性为48.5%、收率为11.4%。
Fluorobenzaldehyde is an intermediate for preparing medicine, pesticide, spice, dyestuff and other fine chemicals. In the synthesis of medicine and pesticide, the introduction of the atom F can improve biological activity and drug effect and reduce the adverse effect. Currently, the application of fluorobenzaldehyde has been continuously extended. In this paper, two methods for the synthesis of p-fluorobenzaldehyde from p-fluorotoluene have been studied.
The synthesis of p-fluorobenzaldehyde by chlorination and hydrolysis was studied. The influence of solvent, catalyst and other reaction conditions on experiment result were discussed . The reaction condition in the hydrolysis of mixed chloride products via hexamethylene tetramine was n(4-fluorobenzyl chloride):n (hexamethylene tetramine)=1 :4, m(chloride):m(ethanol)=1: 1.1, the yield was 80.1 % . The yield was 95.2% in the hydrolysis of p-fluorodichloromethylbenzene in ethanol with the reaction condition of V(p-fluorodichloromethylbenzene) :V(ethanol)=1: 5. The reaction condition in the hydrolysis followed with oxidation from p-fluorobenzyl chloride was: n (4-fluorobenzalcohol):n(hydrogen peroxide) =1:1.3, n ( sodium tungstate):n(salicylic acid)=1:1, the yield was 78.4%.
The synthesis of p-fluorobenzaldehyde by gas-liquid two phase oxidation was studied. The influence of solvent, catalyst, oxidant, temperature and other reaction conditions on experiment result were discussed. Under the optimum condition of V(p-fluorotoluene): V(glacial acetic acid)=1: 3, n (cobaltous acetate):n (manganese acetate) :n (potassium bromide) =1: 2: 3, reaction temperature 90～95℃, oxygen flow 2.4mL/min, the conversion of p-fluorotoluene was 23.5%;the selectivity to p-fluorobenzaldehyde was 48.5% and the yield was 11.4%.
氯化水解法合成对氟苯甲醛,探讨了溶剂、催化剂等反应条件对实验结果的影响。其中乌洛托品法水解氯化混合液制备对氟苯甲醛,反应条件:n(对氟氯苄):n(乌洛托品)=1:4,m(氯化液):m(乙醇)=1:1.1,收率为80.1%;对氟二氯苄在乙醇作用下水解制备对氟苯甲醛,最佳条件V(对氟二氯苄):V(乙醇)=1:5收率为95.2%;对氟氯苄通过水解、氧化制备对氟苯甲醛,当(对氟苯甲醇):n(H_2O_2)=1:1.3,催化剂n(钨酸钠):n(水杨酸)=1:1,收率为78.4%。
氧气液相氧化法合成了对氟苯甲醛,探讨了溶剂、催化剂、氧源、温度等条件对反应结果的影响。通过研究发现,V(对氟甲苯):v(冰醋酸)=1:3,Co/Mn/Br混合物作催化剂,n(Co(OAc)_2.4H_2O):n(Mn(OAc)_2.4H_2O):n(KBr)=1:2:3,在反应温度90-95℃,氧气流量为2.4mL/min时,对氟甲苯的转化率为23.5%,对氟苯甲醛的选择性为48.5%、收率为11.4%。
Fluorobenzaldehyde is an intermediate for preparing medicine, pesticide, spice, dyestuff and other fine chemicals. In the synthesis of medicine and pesticide, the introduction of the atom F can improve biological activity and drug effect and reduce the adverse effect. Currently, the application of fluorobenzaldehyde has been continuously extended. In this paper, two methods for the synthesis of p-fluorobenzaldehyde from p-fluorotoluene have been studied.
The synthesis of p-fluorobenzaldehyde by chlorination and hydrolysis was studied. The influence of solvent, catalyst and other reaction conditions on experiment result were discussed . The reaction condition in the hydrolysis of mixed chloride products via hexamethylene tetramine was n(4-fluorobenzyl chloride):n (hexamethylene tetramine)=1 :4, m(chloride):m(ethanol)=1: 1.1, the yield was 80.1 % . The yield was 95.2% in the hydrolysis of p-fluorodichloromethylbenzene in ethanol with the reaction condition of V(p-fluorodichloromethylbenzene) :V(ethanol)=1: 5. The reaction condition in the hydrolysis followed with oxidation from p-fluorobenzyl chloride was: n (4-fluorobenzalcohol):n(hydrogen peroxide) =1:1.3, n ( sodium tungstate):n(salicylic acid)=1:1, the yield was 78.4%.
The synthesis of p-fluorobenzaldehyde by gas-liquid two phase oxidation was studied. The influence of solvent, catalyst, oxidant, temperature and other reaction conditions on experiment result were discussed. Under the optimum condition of V(p-fluorotoluene): V(glacial acetic acid)=1: 3, n (cobaltous acetate):n (manganese acetate) :n (potassium bromide) =1: 2: 3, reaction temperature 90～95℃, oxygen flow 2.4mL/min, the conversion of p-fluorotoluene was 23.5%;the selectivity to p-fluorobenzaldehyde was 48.5% and the yield was 11.4%.
引文
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