合成水杨醛方法的改进
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摘要
采用Reimer-Tiemman合成法,首次使用十六烷基三甲基溴化铵为相转移催化剂,以苯酚和三氯甲烷为初始原料,制备水杨醛,通过高分辨质谱、傅里叶红外、核磁共振光谱等测试仪器进行表征得以确认.考察了氢氧化钠用量、相转移催化剂十六烷基三甲基溴化铵用量、反应温度、反应时间等因素对水杨醛产率的影响,优化条件之后水杨醛最佳产率为60.5%.此工艺路线具有合成方法简便、反应条件温和、产品质量稳定、产品收率较高等优点,可以进行工业放大.
Salicylaldehyde was synthesized from phenol and chloroform as the initial raw materials,hexadecyl trimethyl ammonium bromide as the phase-transfer catalyst,Reimer-Tiemman as the synthesis method. The product structure was characterized by HRMS,IR and 1H NMR. The influences of sodium hydroxide quantity,phase transfer catalyst quantity,reaction temperature,reaction time on the yield of salicylaldehyde were investigated. The total yield of salicylaldehyde was 60.5%. This new process had many advantages,such as simple process,mild reaction condition,product quality steady,high yield and could be potentially utilized in industrial amplification.
Salicylaldehyde was synthesized from phenol and chloroform as the initial raw materials,hexadecyl trimethyl ammonium bromide as the phase-transfer catalyst,Reimer-Tiemman as the synthesis method. The product structure was characterized by HRMS,IR and 1H NMR. The influences of sodium hydroxide quantity,phase transfer catalyst quantity,reaction temperature,reaction time on the yield of salicylaldehyde were investigated. The total yield of salicylaldehyde was 60.5%. This new process had many advantages,such as simple process,mild reaction condition,product quality steady,high yield and could be potentially utilized in industrial amplification.
引文
[1]化工百科全书编辑委员会.化工百科全书[M].北京:化学工业出版社,1997.
[2]章思规.精细有机化学品技术手册[M].北京:科学出版社,1992.
[3]姚宏亮,李方实.水杨醛的应用及合成方法述评[J].江苏化工,2007(3):17-19.
[4]颜桂炀,郑柳萍,林深,等.相转移催化合成水杨醛[J].石油化工,2000,29(5):354-355.
[5]柳翠英,葛蔚颖,钱浚,等.卤代水杨醛N~-4取代缩氨基硫脲衍生物的合成和生物活性研究[J].化学试剂,2003,25(3):160-162.
[6]党元林,包晓玉,祝心德,等.水杨醛缩精胺及其配合物的合成与生物活性[J].化学研究与应用,2002,14(4):430-432.
[7]江森明,龚启孙,姚巍,等.嘧啶氧苄胺类除草剂的合成研究[J].浙江化工,2005,36(10):11-15.
[8]阮丽琴.水杨醛合成方法[J].福建化工,2004,29(2):33-36.
[9]丁德润,陈燕青,刘鸿志.降解壳聚糖与水杨醛改性衍生物对Ca2+、Fe3+的螯合性质[J].精细化工,2003,20(4):247-249.
[10]刘云,张军,黄振,等.超声波催化和相转移催化合成羟基苯甲醛[J].化学世界,1998,39(10):529-533.
[11]臧阳陵.水杨醛合成方法的评述[J].广西化工,1993,22(4):24-26.
[12]李永常,王万德.电合成水杨醛工艺改进[J].天津化工,1995(3):16-17.
[13]MILONE C,INGOGLIA R,PISTONE A,et al.Activity of gold catalysts in the liquid-phase oxidation of o-hydroxybenzyl alcohol[J].Catalysis Letters,2003,87(3-4):201-209.
[14]王均雷,陈海群.超声波条件下水杨醛的简便合成[J].化学试剂,2011,33(2):182-184.
[15]陈秋丽,刘玉霞,刘菲.水杨醛合成方法的改进[J].河南化工,2017,33(9):31-33.
[16]吴冰琼,黄誉欢,庄淦升,等.合成水杨醛的工艺研究[J].海峡药学,2009,21(6):204-205.
[17]张珍明.水杨醛合成技术的新进展[J].广州化学,2003,28(3):47-51.
[18]王启会,周建平,刘慧娟.苯酚相转移催化合成水杨醛[J].襄樊学院学报,2004,25(5):37-38.
[19]张违庆,卢周,周诗彪,等.水杨醛合成工艺的改进[J].湖南文理学院学报,2006,18(3):40-41.
[20]李广利,章亚东,梁政勇.氯化镁催化苯酚一步法合成水杨醛[J].精细石油化工进展,2013,14(4):43-47.
[2]章思规.精细有机化学品技术手册[M].北京:科学出版社,1992.
[3]姚宏亮,李方实.水杨醛的应用及合成方法述评[J].江苏化工,2007(3):17-19.
[4]颜桂炀,郑柳萍,林深,等.相转移催化合成水杨醛[J].石油化工,2000,29(5):354-355.
[5]柳翠英,葛蔚颖,钱浚,等.卤代水杨醛N~-4取代缩氨基硫脲衍生物的合成和生物活性研究[J].化学试剂,2003,25(3):160-162.
[6]党元林,包晓玉,祝心德,等.水杨醛缩精胺及其配合物的合成与生物活性[J].化学研究与应用,2002,14(4):430-432.
[7]江森明,龚启孙,姚巍,等.嘧啶氧苄胺类除草剂的合成研究[J].浙江化工,2005,36(10):11-15.
[8]阮丽琴.水杨醛合成方法[J].福建化工,2004,29(2):33-36.
[9]丁德润,陈燕青,刘鸿志.降解壳聚糖与水杨醛改性衍生物对Ca2+、Fe3+的螯合性质[J].精细化工,2003,20(4):247-249.
[10]刘云,张军,黄振,等.超声波催化和相转移催化合成羟基苯甲醛[J].化学世界,1998,39(10):529-533.
[11]臧阳陵.水杨醛合成方法的评述[J].广西化工,1993,22(4):24-26.
[12]李永常,王万德.电合成水杨醛工艺改进[J].天津化工,1995(3):16-17.
[13]MILONE C,INGOGLIA R,PISTONE A,et al.Activity of gold catalysts in the liquid-phase oxidation of o-hydroxybenzyl alcohol[J].Catalysis Letters,2003,87(3-4):201-209.
[14]王均雷,陈海群.超声波条件下水杨醛的简便合成[J].化学试剂,2011,33(2):182-184.
[15]陈秋丽,刘玉霞,刘菲.水杨醛合成方法的改进[J].河南化工,2017,33(9):31-33.
[16]吴冰琼,黄誉欢,庄淦升,等.合成水杨醛的工艺研究[J].海峡药学,2009,21(6):204-205.
[17]张珍明.水杨醛合成技术的新进展[J].广州化学,2003,28(3):47-51.
[18]王启会,周建平,刘慧娟.苯酚相转移催化合成水杨醛[J].襄樊学院学报,2004,25(5):37-38.
[19]张违庆,卢周,周诗彪,等.水杨醛合成工艺的改进[J].湖南文理学院学报,2006,18(3):40-41.
[20]李广利,章亚东,梁政勇.氯化镁催化苯酚一步法合成水杨醛[J].精细石油化工进展,2013,14(4):43-47.