CN104326885A - Method for extraction of high purity eugenol from Oleum ocimi gratissimi - Google Patents
Method for extraction of high purity eugenol from Oleum ocimi gratissimi Download PDFInfo
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- CN104326885A CN104326885A CN201410527685.5A CN201410527685A CN104326885A CN 104326885 A CN104326885 A CN 104326885A CN 201410527685 A CN201410527685 A CN 201410527685A CN 104326885 A CN104326885 A CN 104326885A
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- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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Abstract
The invention relates to a method for extraction of high purity eugenol from Oleum ocimi gratissimi. The method comprises the steps of: firstly reacting Oleum ocimi gratissimi with a NaOH solution to generate a eugenol sodium salt containing water layer insoluble in an oil layer, thus realizing first separation of eugenol and non-eugenol essential oil; then conducting distillation on the eugenol sodium salt containing water layer to distill out non-eugenol components along with the distillate, thus realizing secondary separation of eugenol and non-eugenol products; reacting the distillation concentration purified eugenol sodium salt containing distillation base solution with a dilute acid so as to make the eugenol sodium salt generate eugenol so as to precipitate an oil phase from water, with the eugenol purity being up to over 99% at the moment; and finally performing rectification on the eugenol oil layer so as to obtain a eugenol product with purity of 99.9%.
Description
Technical field
The present invention relates to a kind of extraction natural essence spices technical field, a kind of specifically method extracting high-purity Eugenol from Oleum Ocimi Gratissimi.
Background technology
Eugenol has another name called oxymethoxyallylbenzene, chemical name 2-methoxyl group-4-chavicol, and having strong cloves fragrance and gentle pungent fragrance, is colourless to weak yellow liquid under room temperature, and dew is put in air or stored with the passing of time, and gradual change is brown, and matter is gradually dense thick.Natural Eugenol has antibacterial, hypotensive activity, can be used as Bangesic and can be used for carious tooth, and has local preservative activity concurrently.Be mainly used in, in perfume fragrance and various cosmetic essence and soap compound formula, the allotment of food flavour can also being used for as spices.Eugenol is the intermediate of some other spices simultaneously, and derivative has isoeugenol, methyl eugenol, methylisoeugenol, acetyl eugenol, aceteugenol, isoengenol benzylether etc.
Natural Eugenol is present in Oleum Ocimi Gratissimi (60-70%) and Syzygium aromaticum stem oil (70-90%), general by directly carrying out precision fractional distillation to Oleum Ocimi Gratissimi and Syzygium aromaticum stem oil, or first with base extraction then ageing obtain through fractionation again.When extracting Eugenol by straight-forward fractional distillation method, because the non-phenol material in Oleum Ocimi Gratissimi and Syzygium aromaticum stem oil is easy to be polymerized, often cause the productive rate of product not high.About extracting the method for high-purity Eugenol from Oleum Ocimi Gratissimi, domestic more existing open source literature report.
The Li Chaoqun of Yulin City of Guangxi Zhuang Autonomous perfume oil factory etc. have in " production technology research that Syzygium aromaticum stem oil extracts 99% Eugenol " to disclose at its paper delivered and first in Syzygium aromaticum stem oil, add alkali, Eugenol wherein and alkali reaction is made to generate Eugenol sodium to remove non-phenol composition, then acid adding carries out neutralization reaction, separate out the thick product of Eugenol, again through the production technique of highly efficient distilling, obtain the Eugenol of high purity (more than 99%).Chinese patent application CN200910309544, disclose the extraction and separation method of Eugenol, by the cloves of removing impurity is placed in beater, add 4 times, 3 times, 2 times 3% sodium hydroxide solution respectively successively respectively to pull an oar 3 minutes, suction filtration, then adds hydrochloric acid by filtrate and is adjusted to pH5, add sodium-chlor again, 3 ~ 6 DEG C of placements are spent the night, and divide and get volatile oil, vacuum distilling is separated 124 DEG C/10 mm Hg and namely obtains Eugenol.Chinese patent application CN201010168904, disclose a kind of extracting method of eugenol in velvety lilac flower leaves, root of Velvety Lilac powder after sieving is put into extractor, be extracted liquid A with supercritical carbon dioxide extraction, then extraction liquid A NaOH solution extracted 3 times and be extracted liquid B, then after showing acidity with hcl acidifying to blue litmus paper, liquid C is extracted 3 times by extracted with diethyl ether, use anhydrous sodium sulfate drying again, reclaim ether, obtain Eugenol.Chinese patent application CN201410063381, disclose the method producing Eugenol from Syzygium aromaticum stem oil platymiscium, by petroleum ether extraction cloves raw material, recycling design obtains chocolate Syzygium aromaticum stem oil, then Syzygium aromaticum stem oil and buck react obtained containing Eugenol sodium-salt aqueous solution, again atlapulgite is added containing Eugenol sodium-salt aqueous solution agitation and filtration, Eugenol oil reservoir is being separated out in the layering of filtrate acid neutralization, finally again Eugenol is carried out distilling obtained pure Eugenol product.
The existing technology extracting Eugenol from Oleum Ocimi Gratissimi, reacts with containing the Syzygium aromaticum stem oil of Eugenol or Oleum Ocimi Gratissimi the Eugenol sodium salt generating and be insoluble to oil reservoir by buck, thus realizes the object that Eugenol is separated with non-Eugenol derived essential oil.But in prior art, still more non-Eugenol constituents is contained containing in the aqueous solution of Eugenol sodium salt, if without process, with regard to acid neutralization, still containing other non-Eugenol derived essential oils a large amount of in the Eugenol oil reservoir obtained, this will make troubles for follow-up distillation is refining, and affect the purity of the finished product Eugenol.
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, is suitable for the method extracting high-purity Eugenol from Oleum Ocimi Gratissimi of large-scale production.
To achieve these goals, technical scheme provided by the invention is: a kind of method extracting high-purity Eugenol from Oleum Ocimi Gratissimi, comprises the steps:
(1) Oleum Ocimi Gratissimi is added reactor, stir and add NaOH solution by Oleum Ocimi Gratissimi and alkali lye weight ratio 1:1-1:5, control temperature of reaction kettle at 30-50 DEG C, reaction 0.5-1.5h;
(2) stratification, oil reservoir is entered byproduct storage tank, water layer enters distillation tower, and water layer is containing Eugenol sodium salt;
(3) distillation and concentration is not to distillate containing volatile oil, and by distillate stratification, oil reservoir enters byproduct storage tank;
(4) enter in pickling tank by above-mentioned concentrated solution, add dilute sulphuric acid, be adjusted to pH≤6, stratification under stirring, upper strata is Eugenol oil reservoir;
(5) enter rectifying tower after the Eugenol oil reservoir of step (4) being washed 2-3 time, rectification under vacuum obtains high-purity Eugenol.
Step (3) distillation carries out under vacuum tightness≤-0.07.
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, total reflux 0.5-1h, with reflux ratio 15:1-20:1, collect Eugenol byproduct, mainly, ocimene rare containing Terpineol 350, phantol, pinane, enters byproduct storage tank by Eugenol byproduct;
2) heat up, make bottom temperature remain on 120-130 DEG C, tower top temperature remains on 110-120 DEG C, and in tower, vacuum tightness is increased to≤-0.1MPa, reflux ratio 9:1-12:1, and it is Eugenol that collection tower top distillates product;
NaOH concentration described in step (1) is 2-8%.
Dilute sulphuric acid concentration described in step (4) is 30-45%.
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:
Reacted the Eugenol sodium salt water layer generating and be insoluble to oil reservoir by Oleum Ocimi Gratissimi and NaOH solution, realize Eugenol and be separated with non-Eugenol derived essential oil first time.Then distill the water layer containing Eugenol sodium salt, non-Eugenol composition steams with distillate, realizes Eugenol and is separated with the second time of non-Eugenol composition.The end liquid containing Eugenol sodium salt of being purified by distillation and concentration and diluted acid react, and make Eugenol sodium salt generate Eugenol and from water, separate out into oil reservoir, now Eugenol purity can reach more than 99%.Finally again Eugenol oil reservoir is carried out rectifying, because foreign matter content is few, shorten the fractionation time, side reaction can be reduced and occur, finally can obtain the Eugenol product of purity 99.9%.
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
The example extracting the method for high-purity Eugenol from Oleum Ocimi Gratissimi of the present invention, comprises the steps:
Get Oleum Ocimi Gratissimi 2t, proterties: for faint yellow to liquid russet; There is the fragrance of similar cloves, relative density 1.030-1.050, refractive index 1.530-1.540.Main component: Eugenol 70.5%, alpha-terpineol 3.5%, phantol 1.6%, pinane rare 5.3%, ocimene 2.3%.
Oleum Ocimi Gratissimi is added reactor, stirs and add the NaOH solution of concentration 5%, Oleum Ocimi Gratissimi and alkali lye weight ratio 1:3.Control temperature of reaction kettle at 30-50 DEG C, reaction 0.5-1.5h, makes Eugenol be converted into water-soluble Eugenol sodium salt as far as possible completely.Leave standstill 2h layering, oil reservoir upper, containing Eugenol sodium salt water layer under, wherein oil reservoir is mainly containing compositions such as pinane rare, phantol, Terpineol 350s, oil reservoir is entered byproduct storage tank.Water layer being entered distillation tower distill, when not stopping distillation containing volatile oil in distillate, namely observing in distillate no longer containing trickle oil droplet.Collected by the distillate distilled out in distillation tower, stratification, enters byproduct storage tank by oil reservoir, and water can be used to configuration buck and carries out recycle.Above-mentioned concentrated Eugenol solution is entered in pickling tank, adds the dilute sulphuric acid that concentration is 45% under stirring, be adjusted to pH≤6, stratification.Add rectifying tower after above-mentioned oil reservoir is washed 2-3 time, carry out rectifying, vacuum tightness≤-0.09MPa, tower top temperature controls at 120-130 DEG C, the Eugenol of obtained purity 99.9%.
Embodiment 2
Another example extracting the method for high-purity Eugenol from Oleum Ocimi Gratissimi of the present invention, comprises the steps:
Get Oleum Ocimi Gratissimi 2t, proterties: for faint yellow to liquid russet; There is the fragrance of similar cloves, relative density 1.030 ~ 1.050, refractive index 1.530 ~ 1.540.Main component: Eugenol 65.5%, alpha-terpineol 3.8%, phantol 1.6%, pinane rare 1.3%, ocimene 0.8%.
Oleum Ocimi Gratissimi is added reactor, stirs and add the NaOH solution of concentration 2%, Oleum Ocimi Gratissimi and alkali lye weight ratio 1:5.Control temperature of reaction kettle at 30-50 DEG C, reaction 0.5-1.5h, makes Eugenol be converted into water-soluble Eugenol sodium salt as far as possible completely.Leave standstill 1h layering, oil reservoir upper, containing Eugenol sodium salt water layer under, wherein oil reservoir is mainly containing compositions such as pinane rare, phantol, Terpineol 350s, oil reservoir is entered byproduct storage tank.Water layer being entered distillation tower and carry out vacuum distilling, vacuum tightness-0.07MPa, time 2h, when not stopping distillation containing volatile oil in distillate, namely observing in distillate no longer containing trickle oil droplet.Collected by the distillate distilled out in distillation tower, add appropriate NaCl, stratification, oil reservoir is entered byproduct storage tank, water can be used to configuration buck and carries out recycle.Above-mentioned concentrated Eugenol solution is entered in pickling tank, adds the dilute sulphuric acid that concentration is 30% under stirring, be adjusted to pH≤6, stratification.Add rectifying tower after above-mentioned oil reservoir is washed 2-3 time, carry out rectifying, vacuum tightness≤-0.09MPa, tower top temperature controls at 120-130 DEG C, the Eugenol of obtained purity 99.9%.
Embodiment 3
Another example extracting the method for high-purity Eugenol from Oleum Ocimi Gratissimi of the present invention, comprises the steps:
Get Oleum Ocimi Gratissimi 2t, proterties: for faint yellow to liquid russet; There is the fragrance of similar cloves, relative density 1.030-1.050, refractive index 1.530-1.540.Main component: Eugenol 60.5%, alpha-terpineol 4.5%, phantol 2.6%, pinane rare 0.9%, ocimene 1.4%.
Oleum Ocimi Gratissimi is added reactor, stirs and add the NaOH solution of concentration 2%, Oleum Ocimi Gratissimi and alkali lye weight ratio 1:5.Control temperature of reaction kettle at 30-50 DEG C, reaction 0.5-1.5h, makes Eugenol be converted into water-soluble Eugenol sodium salt as far as possible completely.Leave standstill 1h layering, oil reservoir upper, containing Eugenol sodium salt water layer under, wherein oil reservoir is mainly containing compositions such as pinane rare, phantol, Terpineol 350s, oil reservoir is entered byproduct storage tank.Water layer being entered distillation tower and carry out vacuum distilling, vacuum tightness-0.8MPa, time 1.5h, when not stopping distillation containing volatile oil in distillate, namely observing in distillate no longer containing trickle oil droplet.Collected by the distillate distilled out in distillation tower, stratification, enters byproduct storage tank by oil reservoir, and water can be used to configuration buck and carries out recycle.Above-mentioned concentrated Eugenol solution is entered in pickling tank, adds the dilute sulphuric acid that concentration is 35% under stirring, be adjusted to pH≤6, stratification.Rectifying tower is added after above-mentioned oil reservoir is washed 2-3 time, distillation operation step is as follows: 1) rectifying bottom temperature remains on 100-120 DEG C, tower top temperature remains on 80-100 DEG C, vacuum tightness <-0.09MPa, total reflux 0.5-1h, with reflux ratio 15:1-20:1, collect Eugenol byproduct, mainly, ocimene rare containing Terpineol 350, phantol, pinane; 2) heat up, make bottom temperature remain on 120-130 DEG C, tower top temperature remains on 110-120 DEG C, and in tower, vacuum tightness is increased to≤-0.1MPa, reflux ratio 9:1-12:1, and it is Eugenol that collection tower top distillates product.Product Eugenol purity can reach 99.9%.
Claims (5)
1. from Oleum Ocimi Gratissimi, extract a method for high-purity Eugenol, it is characterized in that, comprise the steps:
(1) Oleum Ocimi Gratissimi is added reactor, stir and add NaOH solution by Oleum Ocimi Gratissimi and alkali lye weight ratio 1:1-1:5, control temperature of reaction kettle at 30-50 DEG C, reaction 0.5-1.5h;
(2) stratification, oil reservoir is entered byproduct storage tank, water layer enters distillation tower, and water layer is containing Eugenol sodium salt;
(3) distillation and concentration is not to distillate containing volatile oil, and by distillate stratification, oil reservoir enters byproduct storage tank;
(4) above-mentioned concentrated solution is entered in pickling tank, add dilute sulphuric acid under stirring, be adjusted to
ph≤6, stratification, upper strata is Eugenol oil reservoir;
(5) enter rectifying tower after the Eugenol oil reservoir of step (4) being washed 2-3 time, rectification under vacuum obtains high-purity Eugenol.
2. the method extracting high-purity Eugenol from Oleum Ocimi Gratissimi according to claim 1, is characterized in that, step (3) distillation carries out under vacuum tightness≤-0.07.
3. the method extracting high-purity Eugenol from Oleum Ocimi Gratissimi according to claim 1, 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, total reflux 0.5-1h, with reflux ratio 15:1-20:1, collect Eugenol byproduct, mainly, ocimene rare containing Terpineol 350, phantol, pinane, enters byproduct storage tank by Eugenol byproduct;
2) heat up, make bottom temperature remain on 120-130 DEG C, tower top temperature remains on 110-120 DEG C, and in tower, vacuum tightness is increased to≤-0.1MPa, reflux ratio 9:1-12:1, and it is Eugenol that collection tower top distillates product.
4. the method extracting high-purity Eugenol from Oleum Ocimi Gratissimi according to claim 1, is characterized in that, the NaOH concentration described in step (1) is 2-8%.
5. the method extracting high-purity Eugenol from Oleum Ocimi Gratissimi according to claim 1, is characterized in that, the dilute sulphuric acid concentration described in step (4) is 30-60%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276259A (en) * | 2017-07-13 | 2018-07-13 | 厦门市植研生物科技有限公司 | A kind of technique that natural eugenol is produced as raw material using the aromatic oil containing eugenol |
| CN109160874A (en) * | 2018-09-03 | 2019-01-08 | 中粮德信行健康产业有限公司 | A kind of preparation method of eugenol |
| FR3096050A1 (en) * | 2019-05-17 | 2020-11-20 | Rhodia Operations | EUGENOL PURIFICATION PROCESS AND NEW COMPOSITIONS CONTAINING EUGENOL |
| WO2020234123A1 (en) | 2019-05-17 | 2020-11-26 | Rhodia Operations | Process for the purification of eugenol and novel compositions comprising eugenol |
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| CN101781178A (en) * | 2009-01-21 | 2010-07-21 | 南通芯迎设计服务有限公司 | Extraction and separation method of eugenol |
| CN103819317A (en) * | 2014-02-17 | 2014-05-28 | 王喜军 | Method for preparing eugenol from clove oil plant |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101781178A (en) * | 2009-01-21 | 2010-07-21 | 南通芯迎设计服务有限公司 | Extraction and separation method of eugenol |
| CN103819317A (en) * | 2014-02-17 | 2014-05-28 | 王喜军 | Method for preparing eugenol from clove oil plant |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276259A (en) * | 2017-07-13 | 2018-07-13 | 厦门市植研生物科技有限公司 | A kind of technique that natural eugenol is produced as raw material using the aromatic oil containing eugenol |
| CN109160874A (en) * | 2018-09-03 | 2019-01-08 | 中粮德信行健康产业有限公司 | A kind of preparation method of eugenol |
| FR3096050A1 (en) * | 2019-05-17 | 2020-11-20 | Rhodia Operations | EUGENOL PURIFICATION PROCESS AND NEW COMPOSITIONS CONTAINING EUGENOL |
| WO2020234123A1 (en) | 2019-05-17 | 2020-11-26 | Rhodia Operations | Process for the purification of eugenol and novel compositions comprising eugenol |
| CN113840819A (en) * | 2019-05-17 | 2021-12-24 | 罗地亚经营管理公司 | Method for purifying eugenol and novel compositions comprising eugenol |
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Application publication date: 20150204 |