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

Chemistry and Industry of Forest Products ›› 2022, Vol. 42 ›› Issue (2): 110-114.doi: 10.3969/j.issn.0253-2417.2022.02.015

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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

Abstract

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

CLC Number:

TQ35

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.

Figures/Tables 3

References 16

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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

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

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