芳基六氟异丙醇的合成及其应用研究
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摘要
本论文主要围绕芳基六氟异丙醇的合成及应用展开研究。
以沸点高达105℃、毒性较小的六氟丙酮三水合物(HFA-3H_2O)替代高毒的无水六氟丙酮气体,合成了2-(4-氨基苯)六氟异丙醇、2-(4-羟基苯)六氟异丙醇、双酚AF等芳基六氟异丙醇化合物,对影响反应的各种因素进行了系统研究。研究表明分别以聚乙二醇型酸性离子液体、氧化铌等为催化剂都能成功获得2-(4-氨基苯)六氟异丙醇,催化剂可回收利用,重复使用至少5次,其催化活性无明显变化。可用性质温和的甲基磺酸替代高毒、强腐蚀性的HF为催化剂,实现双酚AF的常压合成,有工业应用前景。采用微波辅助法合成2-(4-羟基苯)六氟异丙醇,能明显缩短反应时间,由常规加热条件下的35h缩短至6h。
以2-(4-氨基苯)六氟异丙醇为原料,合成了7个2-(4-氨基苯)六氟异丙醇缩苯甲醛类物质的Schiff碱化合物,研究表明固相研磨法较溶液法具有无需溶剂和加热、操作简便、能耗少、污染小但收率高等优点,反应时间由溶液法的90-240min缩短至10-50min,收率由71%-87%提高至98%-99%。
以含六氟异丙醇基苯并三唑类化合物的合成为主线,从2-(4-氨基苯)六氟异丙醇出发合成了10余种芳基六氟异丙醇化合物,并研究了它们在紫外吸收剂中的应用。研究表明,2-(2'-羟基-5’-甲基苯基)-6-(2-羟基六氟异丙基)苯并三唑、2-(2'-羟基-5'-叔丁基苯基)-6-(2-羟基六氟异丙基)苯并三唑、2-(2'-羟基-3'-叔丁基-5’-甲基苯基)-6-(2-羟基六氟异丙基)苯并三唑等衍生物具有多个反应基团,不仅能很好吸收280-380nm的紫外光,并且比C(CF3)_2OH相同位置上是H的普通紫外吸收剂熔点提高了40-60℃,光稳定性和热稳定性也有较大提高,是一类具有潜在应用价值的反应型紫外吸收剂。
In this dissertation, a research has been made on the preparation and application of 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols.
A number of useful 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols, such as 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, bisphenol AF,2-(4-hydroxy-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol were prepared using HFA-3H2O as fluorine-containing building blocks. The influence factors of the yield and selectivity were investigated. The results showed that PEG200-DAIL and Nb2Os both were high-efficient and green catalyst for the preparation of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol. By simple sep-aration PEG200-DAIL and Nb_2O_5 could be re-utilized up to five times only with a lit-tle decrease in activity. Bisphenol AF could be synthesized in atmosphere with methane sulfonic acid as catalyst. In synthesis of 2-(4-hydroxy-phenyl)-1,1,1,3,3,3-hexafluoro-pro-pan-2-ol, microwave heating could shorten the reaction time markedly from 35h in co-nventional heating to 6h.
Seven novel fluorine-containing Schiff-bases were synthesized from 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol and benzaldehydes. Compared with conventional process, solid-solid synthesis owned many advantages:simplicity in process and handling, low cost, reduced pollution. The yields of Schiff-bases were increased from 71%-87%to 98%-99%, but the reaction time were shortened from 90-240min to 10-50min.
Besides that, more than ten important 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols, such as benzotriazoles, azobenzenes were obtained and characterized. Three prepared fluorine-containing benzotriazoles were applied as ultraviolet absorbents. The results showed that the three fluorine-containing benzotriazoles all have stronger absorption peak in 280-380nm, furthermore, their light stability and thermal stability had obviously enhanced compared with the benzotriazole without C(CF3)2OH chemical group. The three prepared fluorine-containing benzotriazoles are potential ultraviolet absorbents.
以沸点高达105℃、毒性较小的六氟丙酮三水合物(HFA-3H_2O)替代高毒的无水六氟丙酮气体,合成了2-(4-氨基苯)六氟异丙醇、2-(4-羟基苯)六氟异丙醇、双酚AF等芳基六氟异丙醇化合物,对影响反应的各种因素进行了系统研究。研究表明分别以聚乙二醇型酸性离子液体、氧化铌等为催化剂都能成功获得2-(4-氨基苯)六氟异丙醇,催化剂可回收利用,重复使用至少5次,其催化活性无明显变化。可用性质温和的甲基磺酸替代高毒、强腐蚀性的HF为催化剂,实现双酚AF的常压合成,有工业应用前景。采用微波辅助法合成2-(4-羟基苯)六氟异丙醇,能明显缩短反应时间,由常规加热条件下的35h缩短至6h。
以2-(4-氨基苯)六氟异丙醇为原料,合成了7个2-(4-氨基苯)六氟异丙醇缩苯甲醛类物质的Schiff碱化合物,研究表明固相研磨法较溶液法具有无需溶剂和加热、操作简便、能耗少、污染小但收率高等优点,反应时间由溶液法的90-240min缩短至10-50min,收率由71%-87%提高至98%-99%。
以含六氟异丙醇基苯并三唑类化合物的合成为主线,从2-(4-氨基苯)六氟异丙醇出发合成了10余种芳基六氟异丙醇化合物,并研究了它们在紫外吸收剂中的应用。研究表明,2-(2'-羟基-5’-甲基苯基)-6-(2-羟基六氟异丙基)苯并三唑、2-(2'-羟基-5'-叔丁基苯基)-6-(2-羟基六氟异丙基)苯并三唑、2-(2'-羟基-3'-叔丁基-5’-甲基苯基)-6-(2-羟基六氟异丙基)苯并三唑等衍生物具有多个反应基团,不仅能很好吸收280-380nm的紫外光,并且比C(CF3)_2OH相同位置上是H的普通紫外吸收剂熔点提高了40-60℃,光稳定性和热稳定性也有较大提高,是一类具有潜在应用价值的反应型紫外吸收剂。
In this dissertation, a research has been made on the preparation and application of 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols.
A number of useful 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols, such as 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, bisphenol AF,2-(4-hydroxy-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol were prepared using HFA-3H2O as fluorine-containing building blocks. The influence factors of the yield and selectivity were investigated. The results showed that PEG200-DAIL and Nb2Os both were high-efficient and green catalyst for the preparation of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol. By simple sep-aration PEG200-DAIL and Nb_2O_5 could be re-utilized up to five times only with a lit-tle decrease in activity. Bisphenol AF could be synthesized in atmosphere with methane sulfonic acid as catalyst. In synthesis of 2-(4-hydroxy-phenyl)-1,1,1,3,3,3-hexafluoro-pro-pan-2-ol, microwave heating could shorten the reaction time markedly from 35h in co-nventional heating to 6h.
Seven novel fluorine-containing Schiff-bases were synthesized from 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol and benzaldehydes. Compared with conventional process, solid-solid synthesis owned many advantages:simplicity in process and handling, low cost, reduced pollution. The yields of Schiff-bases were increased from 71%-87%to 98%-99%, but the reaction time were shortened from 90-240min to 10-50min.
Besides that, more than ten important 2-aryl-1,1,1,3,3,3-hexafluoro-propan-2-ols, such as benzotriazoles, azobenzenes were obtained and characterized. Three prepared fluorine-containing benzotriazoles were applied as ultraviolet absorbents. The results showed that the three fluorine-containing benzotriazoles all have stronger absorption peak in 280-380nm, furthermore, their light stability and thermal stability had obviously enhanced compared with the benzotriazole without C(CF3)2OH chemical group. The three prepared fluorine-containing benzotriazoles are potential ultraviolet absorbents.
引文
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