CN104311399A - Method for converting estragole into trans-anethole - Google Patents
Method for converting estragole into trans-anethole Download PDFInfo
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- CN104311399A CN104311399A CN201410529877.XA CN201410529877A CN104311399A CN 104311399 A CN104311399 A CN 104311399A CN 201410529877 A CN201410529877 A CN 201410529877A CN 104311399 A CN104311399 A CN 104311399A
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- anethole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/32—Preparation of ethers by isomerisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Abstract
The invention relates to a method for converting estragole into trans-anethole. The method comprises the steps of carrying out isomerism reaction on the estragole and NaOH solution under pressurization so as to produce the trans-anethole, then carrying out acid pickling and neutralizing on the trans-anethole, washing, carrying out freeze crystalizing, centrifuging to separate, and vacuum rectifying to obtain the high purity trans-anethole with the purity of greater than 99.5%. The method has short reaction time, uses little alkaline, avoids contacting with the air, reduces side reactions like oxidative polymerization, improves the yield of the trans-anethole.
Description
Technical field
The present invention relates to a kind of natural essence spices processing technique field, specifically a kind of estragole is converted into the method for trans-anethole.
Background technology
Trans-anethole (trans trans-anethole, methyl allylphenol), the trans p-allyl anisole of chemical popular name, outward appearance is white crystal, is colourless or atomic yellow liquid when more than 23 DEG C, and fennel is like fragrance, pleasantly sweet.Being widely used at spices, medicine, field of food of high purity (more than 99%) trans-anethole.It is mainly isolated from star aniseed oil obtains, natural star aniseed oil, and containing Multiple components in containing, wherein methyl allylphenol accounts for about 85%, and estragole is 1-10%, cis anethol is 0.45-1%.Because the boiling point of cis anethol and estragole and trans-anethole are isomers, three's relative molecular mass is identical, and boiling point is very close, depends merely on rectifying mode and is difficult to from star aniseed oil, remove cis anethol and estragole.High-purity trans-anethole, the method that will be combined with rectifying by subzero fractionation is produced.In production process after freezing and crystallizing, containing more estragole in the mother liquor that centrifugation goes out, during rectifying, in front-end volatiles, also contain more estragole.Estragole isomery is turned to trans-anethole, there is larger economic worth.Relevant estragole is converted into the method for trans-anethole, domestic more existing open source literature report.
Chinese patent application CN201310428640, disclose the method that estragole isomery turns to methyl allylphenol, by estragole is put into isomery pot, add potassium hydroxide, be heated to 175-185 DEG C, reaction 3-5h, the consumption of catalyzer is the 3-10% of estragole, and reaction terminates rear stopping heating and obtains methyl allylphenol.Chinese patent application CN201310737086, disclosing with estragole oil is the method for Material synthesis methyl allylphenol, and by the isomerization reaction under basic catalyst effect of estragole oil, freezing and crystallizing, separation, obtains trans-anethole.Basic catalyst used is KOH/Al
2o
3, sodium amide, KOH/NaOH, KOH/ polyoxyethylene glycol, KOH/NaOH/ polyoxyethylene glycol one or more, add-on is the 3-10% of estragole weight, at 140-215 DEG C, reaction 0.5-3h.Estragole isomerization reaction disclosed in two sections of patent documentations, condition is under normal pressure, and basic catalyst consumption is estragole weight 3-10%, temperature of reaction > 140 DEG C.
The existing technology turning to trans-anethole from estragole isomery, consume a large amount of catalyzer, temperature is high, contacts with air, easily produce the side reactions such as oxypolymerization in reaction process, and raw material and product volatilization at high temperature cause the waste of resource and the pollution of air.
Summary of the invention
The object of this invention is to provide a kind of material loss few, energy-conserving and environment-protective, cost is low, and product purity is high, and the estragole being suitable for large-scale production is converted into the method for trans-anethole.
To achieve these goals, technical scheme provided by the invention is: a kind of estragole is converted into the method for trans-anethole, comprises the steps:
(1) estragole is added reactor, add the 0.1-1%NaOH solution of estragole weight under stirring, control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, obtains thick methyl allylphenol;
(2) cooled by thick methyl allylphenol, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank, add diluted mineral acid under stirring, adjust pH7-8, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste;
(3) by thick methyl allylphenol oil reservoir washing 2-3 time, freezing and crystallizing is carried out;
(4) by centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole;
(5) thick trans-anethole is added rectifying tower, rectification under vacuum obtains high-purity trans-anethole.
NaOH solution mass percentage concentration described in step (1) is 5-60%.
Estragole described in step (1) is the estragole byproduct after star aniseed oil or anise-oil extract methyl allylphenol, and estragole mass percentage concentration is 5-40%:
The mass percentage concentration of the diluted mineral acid described in step (2) is 10-20% hydrochloric acid or concentration is the sulfuric acid of 20-35%.
Rectification under vacuum described in step (5) comprises the steps:
1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, main, phantol, limonene, Terpineol 350 rare containing pinane and a small amount of trans-anethole;
2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, and it is high-purity trans-anethole that collection tower top distillates product.
Unless otherwise indicated, per-cent of the present invention is mass percent, and each component concentration percentage ratio sum is 100%.
Outstanding advantages of the present invention is:
By estragole and NaOH solution under an increased pressure, carry out the reaction tautomerizing to trans-anethole, the reaction times is short, and the consumption of alkali is few, avoids contacting with air simultaneously, decreases the generation of the side reactions such as oxypolymerization, improve yield.The trans-anethole that isomerization is produced, then through processing such as overpickling neutralization, washing, freezing and crystallizing, centrifugation, rectifications under vacuum, high-purity trans-anethole of purity > 99.5% can be obtained.
Embodiment
By the following examples technical scheme of the present invention is described further.The present invention includes but be not limited only to following examples.
Embodiment 1
Get estragole oil 1t, proterties: colourless to light yellow liquid, in star anise like fragrance, boiling point 216 DEG C, specific refractory power (n
20 d) 1.519-1.5243, relative density (d
25 25) 0.960-0.968.Main component: estragole 85.5%, methyl allylphenol 8.5%, alpha-terpineol 1.5%, phantol 1.7%, pinane rare 2.3%.Estragole is added reactor, and stir and add the NaOH solution that concentration is 60%, alkali lye amount is the 1.0kg of estragole weight.Control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, isomerization obtains thick methyl allylphenol.Cool, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank.Add the sulfuric acid that concentration is 30% under stirring, adjust pH7, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste.By above-mentioned oil reservoir washing 2-3 time, carry out freezing and crystallizing.Centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole 830kg.Thick trans-anethole is added rectifying tower, carry out rectification under vacuum, operation steps: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, be mainly the light constituents such as pinane is rare, Terpineol 350, phantol, limonene; 2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, it is purity > 99.5% trans-anethole 815kg that collection tower top distillates product.Trans-anethole proterties: white crystal or colourless liquid, specific refractory power (n
20 d) 1.557-1.562, relative density (d
25 25) 0.983-0.988, zero pour > 20 DEG C.
Embodiment 2
Get estragole oil 1.5t, proterties: colourless to light yellow liquid, in star anise like fragrance, boiling point 216 DEG C, specific refractory power (n
20 d) 1.519-1.5243, relative density d
25 25) 0.960-0.968.Main component: estragole 75.5%, methyl allylphenol 10.2%, alpha-terpineol 1.5%, phantol 2.4%, pinane rare 1.3%.Estragole is added reactor, and stir and add the NaOH solution that concentration is 5%, alkali lye amount is the 15.0kg of estragole weight.Control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, isomerization obtains thick methyl allylphenol.Cool, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank.Add the dilute hydrochloric acid that concentration is 10% under stirring, adjust pH7, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste.By above-mentioned oil reservoir washing 2-3 time, carry out freezing and crystallizing.Centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole 0.95t.Thick trans-anethole is added rectifying tower, carry out rectification under vacuum, operation steps: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, be mainly the light constituents such as pinane is rare, Terpineol 350, phantol, limonene; 2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, it is purity > 99.5% trans-anethole 0.82t that collection tower top distillates product.Trans-anethole proterties: white crystal or colourless liquid, specific refractory power (n
20 d) 1.557-1.562, relative density (d
25 25) 0.983-0.988, zero pour > 20 DEG C.
Embodiment 3
Get estragole oil 1.5t, proterties: colourless to light yellow liquid, in star anise like fragrance, boiling point 216 DEG C, specific refractory power (n
20 d) 1.519-1.5243, relative density d
25 25) 0.960-0.968.Main component: estragole 60.5%, methyl allylphenol 28.5%, alpha-terpineol 1.5%, phantol 2.1%, pinane rare 3.5%.Estragole is added reactor, and stir and add the NaOH solution that concentration is 30%, alkali lye amount is the 5.0kg of estragole weight.Control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, isomerization obtains thick methyl allylphenol.Cool, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank.Add the dilute hydrochloric acid that concentration is 10% under stirring, adjust pH7, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste.By above-mentioned oil reservoir washing 2-3 time, carry out freezing and crystallizing.Centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole 1.05t.Thick trans-anethole is added rectifying tower, carry out rectification under vacuum, operation steps: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, be mainly the light constituents such as pinane is rare, Terpineol 350, phantol, limonene; 2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, it is purity > 99.5% trans-anethole 0.85t that collection tower top distillates product.Trans-anethole proterties: white crystal or colourless liquid, specific refractory power (n
20 d) 1.557-1.562, relative density (d
25 25) 0.983-0.988, zero pour > 20 DEG C.
Embodiment 4
Get the front-end volatiles 1.0t that anistree anise-oil extracts methyl allylphenol, main component: estragole 38.5%, alpha-terpineol 14.5%, phantol 25.6%, pinane rare 5.4%.Estragole is added reactor, and stir and add the NaOH solution that concentration is 20%, alkali lye amount is the 8.0kg of estragole weight.Control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, isomerization obtains thick methyl allylphenol.Cool, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank.Add the dilute hydrochloric acid that concentration is 15% under stirring, adjust PH7, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste.By above-mentioned oil reservoir washing 2-3 time, carry out freezing and crystallizing.Centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole 0.35t.Thick trans-anethole is added rectifying tower, carry out rectification under vacuum, operation steps: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, be mainly the light constituents such as pinane is rare, Terpineol 350, phantol, limonene; 2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, it is purity > 99.5% trans-anethole 0.24t that collection tower top distillates product.Trans-anethole proterties: white crystal or colourless liquid, specific refractory power (n
20 d) 1.557-1.562, relative density (d
25 25) 0.983-0.988, zero pour > 20 DEG C.
Embodiment 5
Get star aniseed oil 1.0t, main component: estragole 5.5%, trans-anethole 88.7%, alpha-terpineol 1.5%, phantol 2.6%, pinane rare 1.3%.Estragole is added reactor, and stir and add the NaOH solution that concentration is 15%, alkali lye amount is the 8.0kg of estragole weight.Control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, isomerization obtains thick methyl allylphenol.Cool, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank.Add the dilute sulphuric acid that concentration is 35% under stirring, adjust PH7, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is brine waste.By above-mentioned oil reservoir washing 2-3 time, carry out freezing and crystallizing.Centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole 0.91t.Thick trans-anethole is added rectifying tower, carry out rectification under vacuum, operation steps: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect containing trans trans-anethole byproduct, be mainly the light constituents such as pinane is rare, Terpineol 350, phantol, limonene; 2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, it is purity > 99.5% trans-anethole 0.84t that collection tower top distillates product.Trans-anethole proterties: white crystal or colourless liquid, specific refractory power (n
20 d) 1.557-1.562, relative density (d
25 25) 0.983-0.988, zero pour > 20 DEG C.
Claims (5)
1. estragole is converted into a method for trans-anethole, it is characterized in that, comprises the steps:
(1) estragole is added reactor, add the 0.1-1%NaOH solution of estragole weight under stirring, control temperature of reaction at 110-130 DEG C, pressure remains on 0.08-0.1MPa, and reaction 1-2h, obtains thick methyl allylphenol;
(2) cooled by thick methyl allylphenol, when question response temperature in the kettle drops to 50-60 DEG C, thick methyl allylphenol is entered pickling tank, add diluted mineral acid under stirring, adjust pH7-8, stratification, upper strata is thick methyl allylphenol oil reservoir, and lower floor is saliferous water layer;
(3) by thick methyl allylphenol oil reservoir washing 2-3 time, freezing and crystallizing is carried out;
(4) by centrifugation after xln fragmentation, rotating speed > 5000 turns/min, obtains Powdered thick trans-anethole;
(5) add rectifying tower by after above-mentioned Powdered thick trans-anethole heating and melting, rectification under vacuum obtains high-purity trans-anethole.
2. estragole according to claim 1 is converted into the method for trans-anethole, it is characterized in that, the NaOH solution mass percentage concentration described in step (1) is 5-60%.
3. estragole according to claim 1 is converted into the method for trans-anethole, it is characterized in that, estragole described in step (1) be star aniseed oil or anise-oil extract after methyl allylphenol containing estragole byproduct, estragole mass percentage concentration is 5-40%.
4. estragole according to claim 1 is converted into the method for trans-anethole, it is characterized in that, the mass percentage concentration of the diluted mineral acid described in step (2) is 10-20% hydrochloric acid or concentration is the sulfuric acid of 20-35%.
5. estragole according to claim 1 is converted into the method for trans-anethole, it is characterized in that, the rectification under vacuum described in step (5) comprises the steps:
1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, first total reflux 0.5-1h, then with reflux ratio 15:1-20:1, collect the byproduct containing trans trans-anethole, main, phantol, limonene, Terpineol 350 and trans-anethole rare containing pinane;
2) heat up, make bottom temperature remain on 120-130 DEG C, in tower, vacuum tightness is increased to≤-0.1MPa, and tower top temperature remains on 115-120 DEG C, reflux ratio 9:1-10:1, and it is high-purity trans-anethole that collection tower top distillates product.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106350223A (en) * | 2016-08-26 | 2017-01-25 | 江西依思特香料有限公司 | Preparation method of estragole |
| CN107098797A (en) * | 2017-06-23 | 2017-08-29 | 广西万山香料有限责任公司 | A kind of extracting method of chavicol methyl ether |
| CN110156574A (en) * | 2019-07-03 | 2019-08-23 | 承德石油高等专科学校 | A kind of preparation method of purification of alpha-ararin |
| CN111747829A (en) * | 2020-07-02 | 2020-10-09 | 贵州柏森香料有限公司 | Separation and purification method of estragole |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491884A (en) * | 2011-11-29 | 2012-06-13 | 广西壮族自治区林业科学研究院 | Isolation method for high purity anethole |
| CN103755533A (en) * | 2013-12-26 | 2014-04-30 | 北京林业大学 | Method for synthesizing anethole by taking estragole oil as raw material |
-
2014
- 2014-10-09 CN CN201410529877.XA patent/CN104311399A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491884A (en) * | 2011-11-29 | 2012-06-13 | 广西壮族自治区林业科学研究院 | Isolation method for high purity anethole |
| CN103755533A (en) * | 2013-12-26 | 2014-04-30 | 北京林业大学 | Method for synthesizing anethole by taking estragole oil as raw material |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106350223A (en) * | 2016-08-26 | 2017-01-25 | 江西依思特香料有限公司 | Preparation method of estragole |
| CN107098797A (en) * | 2017-06-23 | 2017-08-29 | 广西万山香料有限责任公司 | A kind of extracting method of chavicol methyl ether |
| CN110156574A (en) * | 2019-07-03 | 2019-08-23 | 承德石油高等专科学校 | A kind of preparation method of purification of alpha-ararin |
| CN111747829A (en) * | 2020-07-02 | 2020-10-09 | 贵州柏森香料有限公司 | Separation and purification method of estragole |
| CN111747829B (en) * | 2020-07-02 | 2022-09-02 | 贵州柏森香料有限公司 | Separation and purification method of estragole |
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Application publication date: 20150128 |