CN108558902A - The method that terpinol synthesizes 1,8- Cineoles - Google Patents
The method that terpinol synthesizes 1,8- Cineoles Download PDFInfo
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- CN108558902A CN108558902A CN201810516994.0A CN201810516994A CN108558902A CN 108558902 A CN108558902 A CN 108558902A CN 201810516994 A CN201810516994 A CN 201810516994A CN 108558902 A CN108558902 A CN 108558902A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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Abstract
The invention discloses a kind of methods that terpinol synthesizes 1,8 Cineoles, are related to 1,8 Cineole synthesis technical fields.Using trifluoromethanesulfonic acid zinc or copper trifluoromethanesulfcomposite as catalyst, heterocatalysis terpinol is converted into 1,8 Cineoles.Terpinol, dichloromethane and solid catalyst are added in reaction bulb, are stirred to react under nitrogen protection with blender under normal temperature and pressure, the interference of external environment is avoided.Dichloromethane dilute reaction solution is added after the completion of reaction, saturated sodium bicarbonate solution is added and is extracted, anhydrous sodium sulfate drying is added with saturated common salt water washing in combined dichloromethane phase later three times, and concentration organic phase obtains 1,8 Cineoles of certain purity.Experiments verify that terpinol high conversion rate is up to 98%, 1,8 Cineole conversion efficiency up to 60% or more.It is cheap and easily-available using terpinol as raw material, reduce production cost；The harsh conditions such as high temperature and pressure are avoided, technical step is relatively simple, and the reaction time is short, high conversion rate；It not will produce harmful by-product, it is environmentally friendly.
Description
Technical field
The present invention relates to 1, 8-Cineole synthesis technical fields, and in particular to a kind of side of terpinol synthesis 1, 8-Cineole
Method.
Background technology
1, 8-Cineole is the main component of eucalyptus oil, is mainly used for health, pharmaceutical product.High-purity 1, 8-Cineole product
There is special use value in terms of some medicinal preparation for oral administration (such as cough syrup, chewing gum) and food flavor.1,8- Cineole masters
It separation and Extraction to be obtained from natural products eucalyptus oil, but since natural resources are limited, and impurity component is more in eucalyptus oil, it is difficult
1,8- Cineole products to obtain high-purity meet the market demand.At present in domestic existing Experimental report, has and utilize chemical hand
The research of Duan Hecheng 1, 8-Cineoles, only experimental result yield is relatively low, and technical step is complex, and the purity of product is difficult to control
System, and some not disposable clean, harmful chemical reagent have been used, used condition does not meet Green Chemistry
Scientific idea.
Invention content
The purpose of the present invention is to provide a kind of methods that terpinol synthesizes 1, 8-Cineole, solve existing chemical synthesis 1,
The problems such as low yield, step are complicated in 8- Cineole technologies, purity is difficult to control.
In order to solve the above technical problems, the present invention uses following technical scheme：Terpinol synthesizes the side of 1,8- Cineoles
Method, it is characterised in that comprise the following steps：1) terpinol, dichloromethane and solid catalyst are added in reaction bulb；Room temperature
Under normal pressure, 4h is stirred with blender under nitrogen protection, rotating speed is that 80~90 turns/min is obtained until standing 25min after reaction
To reaction solution I；
2) dichloromethane is added in reaction solution I, 1h is stirred with blender, rotating speed is 40~50 turns/min, is obtained anti-
Answer solution II；
3) saturated sodium bicarbonate solution being added in reaction solution II to be extracted, stratification 10min removes a layer solution,
Obtain reaction solution III；
4) saturated salt solution washing reaction solution III is used, anhydrous sodium sulfate drying is added, is spin-dried for using Rotary Evaporators
To light yellow transparent liquid, i.e. 1, 8-Cineole solution.
Further technical solution is that solid catalyst is trifluoromethanesulfonic acid zinc or trifluoromethanesulfonic acid in the step 1)
Copper.
Further technical solution is the step 1) terpinol and dichloromethane mass ratio is 1:13~1：3.5, pine
Oleyl alcohol is 1 with solid catalyst mass ratio:10.4~1：4.3.
Further technical solution is that terpinol and dichloromethane mass ratio are 1 in the step 2):6~1：2.8.
Further technical solution is that terpinol and saturated sodium bicarbonate solution mass ratio are 1 in the step 3):19
~1：8.2.
Further technical solution is that terpinol and saturated salt solution mass ratio are 1 in the step 4):14.4~1：
7.2。
Further technical solution is that the saturated salt solution in three times washs reaction solution III.
Further technical solution is the terpinol and anhydrous sodium sulfate mass ratio is 1:9.6~1：4.3.
Operation principle：Using trifluoromethanesulfonic acid zinc or copper trifluoromethanesulfcomposite as catalyst, heterocatalysis terpinol converts
For 1,8- Cineoles.Terpinol, dichloromethane and solid catalyst are added in reaction bulb, under normal temperature and pressure, protected in nitrogen
It is stirred to react with blender under shield, chemical equation is expressed as：
Belong to intramolecular etherification reaction.It reacts, keeps away under inert nitrogen gas protection
Exempt from the interference of external environment.Dichloromethane dilute reaction solution is added after the completion of reaction, saturated sodium bicarbonate solution is added and is extracted
It takes, combined dichloromethane phase, anhydrous sodium sulfate drying is added later three times with saturated common salt water washing, concentration organic phase obtains centainly
The 1,8- Cineoles of purity.Experiments verify that terpinol high conversion rate is up to 98%, 1, 8-Cineole conversion efficiency up to 60% with
On.The by-product that reaction generates is mainly limonene, environmentally friendly for another essence and flavoring agent.
Compared with prior art, the beneficial effects of the invention are as follows：Offer one kind is easy to operate, operation safety is good,
The method of the terpinol synthesis 1, 8-Cineole environmental-friendly, yield is higher, purity is excellent is cheap easy using terpinol as raw material
, reduce production cost；The harsh conditions such as high temperature and pressure are avoided, technical step is relatively simple, and the reaction time is short, conversion ratio
It is high；It not will produce harmful by-product, it is environmentally friendly.
Description of the drawings
Fig. 1 is the GC spectrograms of reaction product in embodiment 1 in the present invention.
Fig. 2 is the GC spectrograms of reaction product in embodiment 2 in the present invention.
Fig. 3 is the GC spectrograms of reaction product in embodiment 3 in the present invention.
Fig. 4 is the GC spectrograms of reaction product in embodiment 4 in the present invention.
Fig. 5 is the GC spectrograms of reaction product in embodiment 5 in the present invention.
Specific implementation mode
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to the accompanying drawings and embodiments, right
Invention is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, not
For limiting the present invention.
Embodiment 1
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:13, terpinol and solid catalyst trifluoromethanesulfonic acid zinc mass ratio
It is 1:10.4 are added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 80 turns/min,
To 25min is stood after reaction, reaction solution I is obtained；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:6, it is stirred with blender
1h, rotating speed are 40 turns/min, obtain reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:19, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:14.4, washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:9.6；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.As shown in Figure 1, being detected through GC, 1, 8-Cineole conversion ratio is calculated to obtain
It is 65.5%.
Embodiment 2
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:8, terpinol and solid catalyst trifluoromethanesulfonic acid zinc mass ratio
It is 1:7.4 are added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 85 turns/min, until
25min is stood after reaction, obtains reaction solution I；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:4.5, it is stirred with blender
1h is mixed, rotating speed is 45 turns/min, obtains reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:13.5, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:10.8, washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:6.9；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.As shown in Fig. 2, being detected through GC, 1, 8-Cineole conversion ratio is calculated to obtain
It is 63.5%.
Embodiment 3
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:3.5, terpinol and solid catalyst trifluoromethanesulfonic acid zinc quality
Than being 1:4.3 are added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 90 turns/min,
To 25min is stood after reaction, reaction solution I is obtained；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:2.8, it is stirred with blender
1h is mixed, rotating speed is 50 turns/min, obtains reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:8.2, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:7.2 washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:4.3；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.As shown in figure 3, being detected through GC, 1, 8-Cineole conversion ratio is calculated to obtain
It is 62%.
Embodiment 4
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:13, terpinol and solid catalyst copper trifluoromethanesulfcomposite mass ratio
It is 1:10.4 are added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 80 turns/min,
To 25min is stood after reaction, reaction solution I is obtained；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:6, it is stirred with blender
1h, rotating speed are 40 turns/min, obtain reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:19, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:14.4, washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:9.6；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.As shown in figure 4, being detected through GC, 1, 8-Cineole conversion ratio is calculated to obtain
It is 61%.
Embodiment 5
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:8, terpinol and solid catalyst copper trifluoromethanesulfcomposite mass ratio
It is 1:7.4 being added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 85 turns/min, until
25min is stood after reaction, obtains reaction solution I；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:4.5, it is stirred with blender
1h is mixed, rotating speed is 45 turns/min, obtains reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:13.5, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:10.8, washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:6.9；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.As shown in figure 5, being detected through GC, 1, 8-Cineole conversion ratio is calculated to obtain
It is 60.5%.
Embodiment 6
The method that terpinol synthesizes 1,8- Cineoles, includes the following steps：
1) it is 1 by terpinol and dichloromethane mass ratio:3.5, terpinol and solid catalyst trifluoromethanesulfonic acid copper mass
Than being 1:4.3 are added in reaction bulb；Under normal temperature and pressure, 4h is stirred with blender under nitrogen protection, rotating speed is 90 turns/min,
To 25min is stood after reaction, reaction solution I is obtained；
2) dichloromethane is added in reaction solution I, terpinol is 1 with dichloromethane mass ratio:2.8, it is stirred with blender
1h is mixed, rotating speed is 50 turns/min, obtains reaction solution II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, terpinol and saturated sodium bicarbonate solution matter
Amount is than being 1:8.2, stratification 10min remove a layer solution, obtain reaction solution III；
4) it is 1 with saturated salt solution mass ratio to use saturated salt solution washing reaction solution III, terpinol:7.2, washing point 3
Secondary progress；Anhydrous sodium sulfate drying is added, terpinol is 1 with anhydrous sodium sulfate mass ratio:4.3；It is spin-dried for using Rotary Evaporators
Obtain light yellow transparent liquid, i.e. 1, 8-Cineole solution.Detected through GC, calculate 1, 8-Cineole conversion ratio be 60%.
To sum up, opposite copper trifluoromethanesulfcomposite, under solid catalyst trifluoromethanesulfonic acid zinc, 1, 8-Cineole conversion ratio is more
It is high.
Although reference be made herein to invention has been described for multiple explanatory embodiments of the invention, however, it is to be understood that
Those skilled in the art can be designed that a lot of other modification and implementations, these modifications and implementations will be fallen in this Shen
It please be within disclosed scope and spirit.More specifically, disclose in the application, drawings and claims in the range of, can
With to theme combination layout building block or layout carry out various deformation and improvement.In addition to what is carried out to building block or layout
Outside modification and improvement, to those skilled in the art, other purposes also will be apparent.
Claims (8)
1. the method that terpinol synthesizes 1,8- Cineoles, it is characterised in that include the following steps：
1) terpinol, dichloromethane and solid catalyst are added in reaction bulb；Under normal temperature and pressure, under nitrogen protection with stirring
Device stirring 4h is mixed, rotating speed is that 80~90 turns/min obtains reaction solution I until standing 25min after reaction；
2) dichloromethane is added in reaction solution I, stirs 1h with blender, rotating speed is 40~50 turns/min, obtains reacting molten
Liquid II；
3) saturated sodium bicarbonate solution is added in reaction solution II to be extracted, stratification 10min removes a layer solution, obtains
Reaction solution III；
4) saturated salt solution washing reaction solution III is used, anhydrous sodium sulfate drying is added, is spin-dried for obtaining using Rotary Evaporators light
Yellow transparent liquid, i.e. 1, 8-Cineole solution.
2. the method for terpinol synthesis 1, 8-Cineole according to claim 1, it is characterised in that：It is solid in the step 1)
Body catalyst is trifluoromethanesulfonic acid zinc or copper trifluoromethanesulfcomposite.
3. the method for terpinol synthesis 1, 8-Cineole according to claim 2, it is characterised in that：Step 1) the pine tar
Alcohol is 1 with dichloromethane mass ratio:3.5~1：13, terpinol is 1 with solid catalyst mass ratio:4.3~1：10.4.
4. the method for terpinol synthesis 1, 8-Cineole according to claim 2, it is characterised in that：It is loose in the step 2)
Oleyl alcohol is 1 with dichloromethane mass ratio:2.8~1：6.
5. the method for terpinol synthesis 1, 8-Cineole according to claim 2, it is characterised in that：It is loose in the step 3)
Oleyl alcohol is 1 with saturated sodium bicarbonate solution mass ratio:8.2~1：19.
6. the method for terpinol synthesis 1, 8-Cineole according to claim 2, it is characterised in that：It is loose in the step 4)
Oleyl alcohol is 1 with saturated salt solution mass ratio:7.2~1：14.4.
7. the method for terpinol synthesis 1, 8-Cineole according to claim 6, it is characterised in that：The saturated salt solution
Reaction solution III is washed in three times.
8. the method for terpinol synthesis 1, 8-Cineole according to claim 2, it is characterised in that：The terpinol and nothing
Aqueous sodium persulfate mass ratio is 1:4.3~1：9.6.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113603705A (en) * | 2021-03-05 | 2021-11-05 | 中国林业科学研究院林产化学工业研究所 | Method for preparing 1, 8-cineole derivative from 3-carene |
| CN114230575A (en) * | 2021-12-07 | 2022-03-25 | 南昌工程学院 | Method for synthesizing 1, 8-cineole by catalyzing alpha-terpineol in solvent-free system |
| CN116063314A (en) * | 2021-11-01 | 2023-05-05 | 四川大学 | Method for separating alpha-terpineol and 1, 8-eucalyptol by association extraction |
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| CN114230575A (en) * | 2021-12-07 | 2022-03-25 | 南昌工程学院 | Method for synthesizing 1, 8-cineole by catalyzing alpha-terpineol in solvent-free system |
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Application publication date: 20180921 |