CN107188788B - Eugenol purification method - Google Patents
Eugenol purification method Download PDFInfo
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- CN107188788B CN107188788B CN201710382865.2A CN201710382865A CN107188788B CN 107188788 B CN107188788 B CN 107188788B CN 201710382865 A CN201710382865 A CN 201710382865A CN 107188788 B CN107188788 B CN 107188788B
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- CN
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- Prior art keywords
- eugenol
- solution
- aqueous solution
- compound
- purification method
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- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 title claims abstract description 122
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000005770 Eugenol Substances 0.000 title claims abstract description 60
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229960002217 eugenol Drugs 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000000746 purification Methods 0.000 title claims abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229940126062 Compound A Drugs 0.000 claims abstract description 13
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000012071 phase Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000005191 phase separation Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000000686 essence Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 4
- YXAQTUMTSYQJHN-UHFFFAOYSA-N 2-methoxy-4-prop-2-enylphenol;sodium Chemical compound [Na].COC1=CC(CC=C)=CC=C1O YXAQTUMTSYQJHN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 3
- 244000223014 Syzygium aromaticum Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a eugenol purification method, which comprises the following steps: step 1, dissolving a compound A shown as a structural formula I in an organic solvent to obtain a solution A; step 2, mixing the aqueous solution containing the crude eugenol with the solution A, standing, and then carrying out phase separation to obtain a water phase and an organic phase; and 3, adding alkali liquor into the organic phase to obtain purified eugenol. The organic solvent in step 1 is dichloromethane. The concentration of the compound A in the solution A is 1X 10‑20.1M. The method for purifying the eugenol provided by the invention can be used for separating the eugenol from the aqueous solution with lower content of the eugenol, and is simple to operate and high in separation efficiency.
Description
Technical Field
The invention relates to the technical field of element separation, and particularly relates to a eugenol purification method.
Background
Eugenol (shown as structural formula I) is 4-allyl-2-methoxyphenol with a chemical name of C10H12O2, a molecular formula of 164.21, is colorless to light yellow viscous liquid, has strong clove fragrance, a boiling point of 253 ℃, a melting point of-9.2 to-9.1 ℃, a relative density (d2525) of 1.053 to 1.064 and a refractive index (nD20) of 1.538 to 1.542, is slightly soluble in water, can be mixed with alcohol, ether, chloroform and volatile oil, and is soluble in glacial acetic acid and caustic alkali solution.
The eugenol gradually becomes dark and thick in the air, and metal ions such as iron, zinc and the like can catalyze the oxidation, so the storage temperature is not more than 25 ℃, and the eugenol is stored away from light. Eugenol also turns red litmus blue, which is blue when reacted with an ethanol solution of ferric chloride.
The eugenol can be used in perfume essence and various cosmetic essence and soap essence formula, and the dosage is within 20%. In addition, the product can also be used in edible essence formula. The perfume can be used as fixative and modifier for wood fragrance type and oriental type essence. Eugenol is the main fragrance agent for preparing essence with fragrance of clove and carnation. It is also frequently used in mint type, nut type, spicy type food essences and tobacco essences. Can also be used for synthesizing vanillin. It is also used in medicine and oral hygiene products. Eugenol is collected in FEMA2467 of USA; FDA approval in the united states for food.
In the prior art, for example, the methods for preparing eugenol are disclosed in publication numbers CN101781178A and CN102060677B, but the product purity still needs to be improved, and the requirement of high-purity eugenol is difficult to meet.
Disclosure of Invention
The invention provides a eugenol purification method, which can obtain high-purity eugenol and has the advantages of simple operation and high separation efficiency.
A method for purifying eugenol, comprising:
step 1, dissolving a compound A shown as a structural formula I in an organic solvent to obtain a solution A;
step 2, mixing the aqueous solution containing the crude eugenol with the solution A, standing, and then carrying out phase separation to obtain a water phase and an organic phase;
and 3, adding alkali liquor into the organic phase to obtain the purified eugenol.
The invention takes the compound A solution as an extracting agent to extract the eugenol from the aqueous solution, and has the advantages of good selectivity, high extraction rate and simple operation.
Preferably, the organic solvent in step 1 is dichloromethane. The compound A has good solubility in dichloromethane, and the dichloromethane does not influence the interaction of the compound A and eugenol, thereby ensuring higher extraction rate.
In order to ensure the sufficient effect of the compound A and the eugenol, the concentration of the compound A in the solution A is preferably 1X 10-20.1M. Namely, in the concentration range, the eugenol and the compound A are convenient to realize the mutual combination at the molecular level, thereby ensuring the extraction rate.
In order to improve the extraction efficiency, preferably, the molar concentration of the compound A in the solution A is 8-12 times of that of the eugenol in the aqueous solution, and the aqueous solution containing the eugenol is mixed with the solution A in equal volume.
Preferably, step 2 is carried out at room temperature and atmospheric pressure. The invention can be carried out at normal room temperature and normal pressure without harsh pressure and temperature conditions when eugenol is extracted.
Preferably, the standing time in the step 2 is not less than 2 h. More preferably, the standing time in step 2 is 6 to 24 hours.
The invention can extract the clove from the aqueous solution with lower eugenol contentThe concentration of eugenol in the eugenol, preferably the aqueous solution containing eugenol, is 1X 10-3～0.1M。
The function of the alkali liquor in the step 3 is to convert eugenol into a form of sodium eugenol, so that the recovery of eugenol is realized, preferably, the alkali liquor in the step 3 is: NaOH aqueous solution with the molar concentration of 0.01-0.1M.
The method for purifying the eugenol provided by the invention can be used for separating the eugenol from the aqueous solution with low content of the eugenol, and is simple to operate and high in separation efficiency.
Detailed Description
Example 1
(1) Dissolving eugenol (purity of 80%) in water to give a concentration of 1 × 10-3M in aqueous eugenol;
(2) dissolving a compound A shown as a structural formula I in CH2Cl2Is prepared to have a concentration of 1X 10-2Solution A of M;
(3) placing 10mL of eugenol aqueous solution and 10mL of solution A in a 50mL separating funnel at room temperature and normal pressure, shaking for 30 minutes, standing for 12 hours, and separating phases to obtain a water phase and an organic phase;
and (4) measuring the concentration of the eugenol in the water phase by utilizing HPLC analysis, and calculating the extraction rate, wherein the extraction rate of the eugenol is 41%.
(4) Adding 0.01M NaOH aqueous solution into the organic phase to convert the eugenol into sodium eugenol, and then acidifying the sodium eugenol by adding acid to obtain the eugenol, wherein the purity can reach 99 percent by detection.
Claims (8)
1. A eugenol purification method is characterized by comprising the following steps:
step 1, dissolving a compound A shown as a structural formula I in an organic solvent to obtain a solution A;
step 2, mixing the aqueous solution containing the crude eugenol with the solution A, standing, and then carrying out phase separation to obtain a water phase and an organic phase;
and 3, adding alkali liquor into the organic phase to obtain the purified eugenol.
2. The method for purifying eugenol as claimed in claim 1, wherein the organic solvent in step 1 is dichloromethane.
3. The method for purifying eugenol as claimed in claim 1, wherein the concentration of compound a in solution a is 1 x 10-2～0.1M。
4. The eugenol purification method according to claim 1, wherein step 2 is carried out at room temperature and normal pressure.
5. The method for purifying eugenol as claimed in claim 1, wherein the standing time in step 2 is not less than 2 hours.
6. The method for purifying eugenol as claimed in claim 1, wherein the concentration of eugenol in the aqueous solution containing eugenol is 1 x 10-3～0.1M。
7. The eugenol purification method as claimed in claim 1, wherein the molar concentration of the compound A in the solution A is 8-12 times of the molar concentration of the eugenol in the aqueous solution, and the aqueous solution containing the eugenol is mixed with the solution A in equal volume.
8. The eugenol purification method according to claim 1, wherein the lye in step 3 is: NaOH aqueous solution with the molar concentration of 0.01-0.1M.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710382865.2A CN107188788B (en) | 2017-05-26 | 2017-05-26 | Eugenol purification method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710382865.2A CN107188788B (en) | 2017-05-26 | 2017-05-26 | Eugenol purification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107188788A CN107188788A (en) | 2017-09-22 |
| CN107188788B true CN107188788B (en) | 2020-05-29 |
Family
ID=59875845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710382865.2A Expired - Fee Related CN107188788B (en) | 2017-05-26 | 2017-05-26 | Eugenol purification method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107188788B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5965035A (en) * | 1982-10-05 | 1984-04-13 | T Hasegawa Co Ltd | Preparation of trans-isoeugenol and its derivative |
| CN101696159A (en) * | 2009-11-11 | 2010-04-21 | 王永清 | Method for extracting and separating eugenol, pharmaceutical composition containing eugenol and preparation method thereof |
| 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 |
| CN101817730A (en) * | 2010-05-12 | 2010-09-01 | 天津中敖生物科技有限公司 | Method for extracting eugenol in velvety lilac flower leaves |
| CN102060677A (en) * | 2010-12-20 | 2011-05-18 | 大兴安岭嘉迪欧营养原料有限公司 | Method for enriching and purifying eugenol in Chinese pink herb |
| CN104557482A (en) * | 2013-10-22 | 2015-04-29 | 天津中敖生物科技有限公司 | Extraction method of eugenol |
| CN105294409A (en) * | 2015-09-15 | 2016-02-03 | 重庆欣欣向荣精细化工有限公司 | Eugenol synthesis method |
-
2017
- 2017-05-26 CN CN201710382865.2A patent/CN107188788B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5965035A (en) * | 1982-10-05 | 1984-04-13 | T Hasegawa Co Ltd | Preparation of trans-isoeugenol and its derivative |
| 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 |
| CN101696159A (en) * | 2009-11-11 | 2010-04-21 | 王永清 | Method for extracting and separating eugenol, pharmaceutical composition containing eugenol and preparation method thereof |
| CN101817730A (en) * | 2010-05-12 | 2010-09-01 | 天津中敖生物科技有限公司 | Method for extracting eugenol in velvety lilac flower leaves |
| CN102060677A (en) * | 2010-12-20 | 2011-05-18 | 大兴安岭嘉迪欧营养原料有限公司 | Method for enriching and purifying eugenol in Chinese pink herb |
| CN104557482A (en) * | 2013-10-22 | 2015-04-29 | 天津中敖生物科技有限公司 | Extraction method of eugenol |
| CN105294409A (en) * | 2015-09-15 | 2016-02-03 | 重庆欣欣向荣精细化工有限公司 | Eugenol synthesis method |
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| Publication number | Publication date |
|---|---|
| CN107188788A (en) | 2017-09-22 |
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