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林产化学与工业 ›› 2019, Vol. 39 ›› Issue (5): 67-72.doi: 10.3969/j.issn.0253-2417.2019.05.009

• 研究报告 • 上一篇    下一篇

3-对䓝烯-1-胺的合成工艺研究

董欢欢1,2,徐士超1,2,3,王婧1,2,3,4,张红梅1,2,曾小静1,2,陈玉湘1,2,3,赵振东1,2,3,*()   

  1. 1. 中国林业科学研究院 林产化学工业研究所;生物质化学利用国家工程实验室;国家林业和草原局 林产化学工程重点实验室;江苏省 生物质能源与材料重点实验室,江苏 南京 210042
    2. 南京林业大学 江苏省林业资源高效加工利用协同创新中心,江苏 南京 210037
    3. 中国林业科学研究院 林业新技术研究所,北京 100091
    4. 北京林业大学 材料科学与技术学院,北京 100083
  • 收稿日期:2019-06-24 出版日期:2019-10-25 发布日期:2019-11-01
  • 通讯作者: 赵振东 E-mail:zdzhao@189.cn
  • 作者简介:董欢欢(1995—  ),女,甘肃天水人,硕士生,主要从事萜类化学及利用相关研究
  • 基金资助:
    国家自然科学基金资助项目(31870557);国家自然科学基金资助项目(31600466);中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2018SZ012)

Synthetic Technology of p-Menth-3-en-1-amine

Huanhuan DONG1,2,Shichao XU1,2,3,Jing WANG1,2,3,4,Hongmei ZHANG1,2,Xiaojing ZENG1,2,Yuxiang CHEN1,2,3,Zhendong ZHAO1,2,3,*()   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
    2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
    3. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
    4. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China
  • Received:2019-06-24 Online:2019-10-25 Published:2019-11-01
  • Contact: Zhendong ZHAO E-mail:zdzhao@189.cn
  • Supported by:
    国家自然科学基金资助项目(31870557);国家自然科学基金资助项目(31600466);中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2018SZ012)

摘要:

以1, 8-对䓝烷二乙酰胺为原料,通过酸催化消去和碱催化水解两步反应制得3-对䓝烯-1-胺,采用单因素和正交试验考察了不同条件对反应的影响。酸催化消去反应的最佳反应条件为:20 mmol对䓝烷二乙酰胺, 35 mL质量分数12.5% H2SO4(24 mmol)溶液,反应时间8 h,N-乙酰基-3-对䓝烯-1-胺产率41.6%;碱催化水解的最佳反应条件为:n(N-乙酰基-3-对䓝烯-1-胺):n(NaOH)为1:7,30 mL乙二醇,反应时间11 h,反应温度170 ℃,3-对䓝烯-1-胺产率82.2%,总产率为34.2%。3-对䓝烯-1-胺经减压精馏到纯度97%,采用ESI-MS、FT-IR、1H NMR及13C NMR等仪器分析进行表征,确定了产物结构。

关键词: 单萜衍生物, 1, 8-对䓝烷二乙酰胺, 3-对䓝烯-1-胺

Abstract:

p-Menth-3-en-1-amine was synthesized from p-menthane diacetylamide by two steps as an acid-catalyzed elimination and an alkaline-catalyzed hydrolysis. The effects of different conditions on these reactions were studied by single-factor and orthogonal tests. The optimal reaction conditions of the acid-catalyzed elimination are shown as 20 mmol p-menthane diacetylamide, 35 mL 12.5% H2SO4 solution (24 mmol) and reaction time 8 h, under which the yield is 41.6%; And the optimized technological parameters of the alkaline-catalyzed hydrolysis are shown as n(N-diacetyl-3-en-1-amine):n(NaOH) 1:7, 30 mL ethylene glycol as the solvent, reaction time 11 h and reaction temperature 170 ℃, to give N-diacetyl-3-en-1-amine in a yield of 82.2%, total yield is 34.2%, purified to 97% by vacuum rectification. The structure of the compound was determined by ESI-MS, FT-IR, 1H NMR and 13C HMR spectroscopic analyses.

Key words: monoterpene derivative, 1, 8-p-menthanediacetylamide, p-menth-3-en-1-amine

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