罗汉柏木烯合成罗汉柏木二醇研究

doi:10.3969/j.issn.0253-2417.2022.02.015

林产化学与工业 ›› 2022, Vol. 42 ›› Issue (2): 110-114.doi: 10.3969/j.issn.0253-2417.2022.02.015

罗汉柏木烯合成罗汉柏木二醇研究

张胜¹(), 朱凯¹^,²^,*(), 毛萍³

1. 南京林业大学化学工程学院, 江苏南京 210037
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. 南京欧亚香精香料有限公司, 江苏南京 210037

收稿日期:2021-02-03 出版日期:2022-04-28 发布日期:2022-05-06
通讯作者: 朱凯 E-mail:1071929101@qq.com;zhukai53@163.com
作者简介:朱凯, 教授, 硕士生导师, 研究方向为香精香料; E-mail: zhukai53@163.com
张胜(1995-), 男, 贵州遵义人, 硕士生, 主要从事香精香料方面研究; E-mail: 1071929101@qq.com
基金资助:
国家重点研发计划资助项目(2018YFD0600405);江苏高校优势学科建设工程项目

Study on the Synthesis of Thujopsane-8, 9-diol from Thujopsene

Sheng ZHANG¹(), Kai ZHU¹^,²^,*(), Ping MAO³

1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
2. Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
3. Nanjing Eurasia Flavors & Fragrances Co., Ltd., Nanjing 210037, China

Received:2021-02-03 Online:2022-04-28 Published:2022-05-06
Contact: Kai ZHU E-mail:1071929101@qq.com;zhukai53@163.com

摘要/Abstract

摘要：

以罗汉柏木烯为原料，KMnO₄为氧化剂，叔丁醇/水(体积比2:1)为溶剂，通过罗汉柏木烯的双羟基化反应合成得到了罗汉柏木二醇。考察了反应条件对双羟基化反应的影响，得到最佳工艺条件为：反应温度40℃，n(KMnO₄): n(罗汉柏木烯)=1.8:1，反应时间3 h，KMnO₄水溶液质量分数为5%。在此条件下，罗汉柏木烯的转化率为98.3%，罗汉柏木二醇的收率和选择性分别为88.7%和90.2%。采用GC-MS、FT-IR和¹H NMR等方法对产物结构进行了表征，确定产物为罗汉柏木二醇。

关键词: 罗汉柏木二醇, KMnO₄, 双羟基化, 罗汉柏木烯

Abstract:

Thujopsane-8, 9-diol was synthesized by the dihydroxylation of thujopsene using KMnO₄ as oxidant, tertiary-butyl alcohol/H₂O(2:1, volume ratio) as solvent in the presence of NaOH. The effects of reaction conditions on the dihydroxylation reaction were investigated and the optimal reaction conditions were reaction temperature 40 ℃, molar ratio of raw materials n(KMnO₄): n(thujopsene)=1.8:1, reaction time 3 h, mass fraction of KMnO₄ aqueous solution 5%. Under these conditions, the conversion rate of thujopsene was 98.3%, the yield and selectivity of thujopsane-8, 9-diol were 88.7% and 90.2%, respectively. The structure of the product was characterized by GC-MS, FT-IR and ¹H NMR, and confirmed to be thujopsane-8, 9-diol.

Key words: thujopsane-8, 9-diol, KMnO₄, dihydroxylation, thujopsene

中图分类号:

TQ35

张胜, 朱凯, 毛萍. 罗汉柏木烯合成罗汉柏木二醇研究[J]. 林产化学与工业, 2022, 42(2): 110-114.

Sheng ZHANG, Kai ZHU, Ping MAO. Study on the Synthesis of Thujopsane-8, 9-diol from Thujopsene[J]. Chemistry and Industry of Forest Products, 2022, 42(2): 110-114.

图/表 3

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实验号 No.	反应温度/℃ reaction temperature	反应时间/h reaction time	KMnO₄水溶液质量分数/% mass fraction of KMnO₄ aqueous solution	n(KMnO₄): n(罗汉柏木烯) n(KMnO₄): n(thujopsene)	得率/% yield
1	30	3	4	1.4	81.3
2	30	4	4.5	1.6	83.8
3	30	5	5	1.8	86.0
4	40	3	4.5	1.8	87.0
5	40	4	5	1.4	84.1
6	40	5	4	1.6	85.7
7	50	3	5	1.6	86.7
8	50	4	4	1.8	86.3
9	50	5	4.5	1.4	82.0
k₁	83.7	85.0	84.4	82.5
k₂	85.6	84.7	84.3	85.4
k₃	85.0	84.6	85.6	86.4
R	1.9	0.4	1.3	3.9

罗汉柏木烯合成罗汉柏木二醇研究

Study on the Synthesis of Thujopsane-8, 9-diol from Thujopsene

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