CN114989006A - Method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis - Google Patents
Method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis Download PDFInfo
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- CN114989006A CN114989006A CN202210725112.8A CN202210725112A CN114989006A CN 114989006 A CN114989006 A CN 114989006A CN 202210725112 A CN202210725112 A CN 202210725112A CN 114989006 A CN114989006 A CN 114989006A
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- China
- Prior art keywords
- ferulic acid
- volatile oil
- ligusticum wallichii
- separating
- angelica sinensis
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- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 title claims abstract description 41
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 title claims abstract description 39
- 235000001785 ferulic acid Nutrition 0.000 title claims abstract description 39
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 title claims abstract description 39
- 229940114124 ferulic acid Drugs 0.000 title claims abstract description 39
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000000341 volatile oil Substances 0.000 title claims abstract description 33
- 241000112528 Ligusticum striatum Species 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 19
- 241000382455 Angelica sinensis Species 0.000 title claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000007788 liquid Substances 0.000 claims abstract description 37
- 239000000243 solution Substances 0.000 claims abstract description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011259 mixed solution Substances 0.000 claims abstract description 14
- 230000002378 acidificating effect Effects 0.000 claims abstract description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000008213 purified water Substances 0.000 claims abstract description 9
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims abstract description 5
- 239000011780 sodium chloride Substances 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 241000244365 Ligusticum sinense Species 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- 235000001287 Guettarda speciosa Nutrition 0.000 abstract description 14
- 239000006187 pill Substances 0.000 abstract description 8
- 239000012043 crude product Substances 0.000 abstract description 7
- 239000009999 naoan Substances 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 244000061520 Angelica archangelica Species 0.000 abstract 2
- 241000125175 Angelica Species 0.000 description 12
- 239000000126 substance Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 235000007162 Ferula assa foetida Nutrition 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 235000012850 Ferula foetida Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica, which comprises the steps of adjusting the pH of a mixed solution to 7-13 by using a 1-40% NaOH solution through alkalinity adjustment, adding a proper amount of purified water into the mixed solution through primary extraction, standing, separating liquid, removing a lower layer liquid, adjusting the value of an upper layer liquid by using hydrochloric acid, adjusting the pH to 3-6, concentrating the adjusted acidic upper layer liquid under reduced pressure until no water is separated out to obtain a primary concentrated liquid, repeating the step 7 to obtain a secondary concentrated liquid, adding a proper amount of 75-100% ethanol into the secondary concentrated liquid for dissolving, removing NaCl crystals, concentrating the solution under reduced pressure until no alcohol is separated out to obtain a ferulic acid crude product, and fully utilizing the brain-safety dropping pill by-products of the ligusticum wallichii and the angelica to obtain a crude product with high ferulic acid content, wherein the ferulic acid content is increased by 10-40 times. The stable curative effect of the Naoan dropping pill product is fully ensured, the additional value of the product is improved, and the economic benefit is increased; no harmful waste is generated; simple operation, stable yield and low cost, and can be operated in large batch.
Description
Technical Field
The invention relates to the field of ferulic acid separation from volatile oil of ligusticum wallichii and angelica sinensis, and in particular relates to a method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis.
Background
Ferulic acid, the chemical name of which is 3-methoxy-4-hydroxycinnamic acid and the chemical formula of which is C10H10O4, is one of the derivatives of cinnamic acid, the chemical name of which is 3-methoxy-4-hydroxycinnamic acid, has higher content in Chinese medicinal materials such as asafetida, angelica, ligusticum wallichii, rhizoma cimicifugae, spina date seed and the like, and is one of the effective components of the Chinese medicinal materials. Ferulic acid has cis-isomer and trans-isomer, and is a light yellow solid.
However, the existing naoan dropping pill by-product ligusticum wallichii and angelica volatile oil is lack of a method for purifying ferulic acid in the production process, so that the value of the naoan dropping pill by-product ligusticum wallichii and angelica volatile oil is not fully utilized, therefore, the improvement is made, a method for separating ferulic acid from ligusticum wallichii and angelica volatile oil is provided, the naoan dropping pill by-product ligusticum wallichii and angelica volatile oil is utilized to purify ferulic acid, and the obtained ferulic acid crude product can be used for improving the content of ferulic acid of the naoan dropping pill or used as a raw material of food and cosmetics.
Disclosure of Invention
The invention aims to: in order to solve the problems of the prior art, the invention provides the following technical scheme: the invention relates to a method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica, which aims to improve the problems and specifically comprises the following steps: the method comprises the following steps of preparing materials in step 1, adding alcohol to dissolve in step 2, adjusting alkalinity in step 3, extracting for the first time in step 4, adding acid to reduce in step 5, concentrating under reduced pressure in step 6, extracting for the second time in step 7, concentrating the adjusted acidic upper layer liquid under reduced pressure in step 8 until no water is distilled off to obtain a primary concentrated solution, and repeating the step 7 to obtain a secondary concentrated solution for purification.
As a preferred technical scheme of the invention, the Ligusticum wallichii and Chinese angelica volatile oil (with ferulic acid content of 0.5-1%), ethanol, NaOH, purified water and hydrochloric acid are prepared in the step 1.
According to the preferable technical scheme, alcohol is added in the step 2 to dissolve a proper amount of the ligusticum wallichii and angelica volatile oil, 75% -95% of ethanol is added, and the volatile oil and the ethanol are fully stirred and dissolved to obtain a mixed solution, wherein the ratio of the ethanol to the volatile oil is 4-1: 1-5.
As the preferable technical scheme of the invention, the pH value of the mixed solution is adjusted to be between 7 and 13 by using 1 to 40 percent NaOH solution for adjusting alkalinity in the step 3.
As a preferable technical scheme of the invention, step 4 is to add a proper amount of purified water into the mixed solution with adjusted alkalinity for one-time extraction, and to perform standing and liquid separation.
As a preferable technical scheme of the invention, the lower layer liquid is discarded in the step 5, the upper layer liquid is adjusted by hydrochloric acid, and the pH is adjusted to be between 3 and 6.
As a preferable technical scheme of the invention, step 6 is reduced pressure concentration, and the adjusted acidic upper layer liquid is reduced pressure concentrated until no water is distilled off, so as to obtain a primary concentrated solution.
As the preferable technical scheme of the invention, in the step 7, the primary concentrated solution is used as the raw oil for the secondary extraction, and the operation of 1-5 is repeated once to obtain the secondary concentrated solution.
And 8, concentrating the adjusted acidic upper layer liquid under reduced pressure until no water is distilled off to obtain a primary concentrated liquid, repeating the step 7 to obtain a secondary concentrated liquid, adding a proper amount of 75-100% ethanol to dissolve the secondary concentrated liquid, removing NaCl crystals, concentrating the solution under reduced pressure until no ethanol is distilled off to obtain a ferulic acid crude product with the ferulic acid content of 7-25%.
Compared with the prior art, the invention has the following beneficial effects: in the scheme of the invention: by fully utilizing the volatile oil (byproduct of Naoan dropping pill) of the ligusticum wallichii and the angelica, a crude product with high ferulic acid content is obtained, and the ferulic acid content is improved by 10-40 times. The stable curative effect of the Naoan dropping pill product is fully ensured, the additional value of the product is improved, and the economic benefit is increased; the environment is protected, the environmental pollution is reduced, and no harmful waste is generated; simple operation, stable yield and low cost, and can be operated in large batch.
Description of the drawings:
FIG. 1 is a flow chart of the structure provided by the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the accompanying drawings. It is clear that the described embodiment is a specific implementation of the invention and is not limited to all embodiments.
Thus, the following detailed description of the embodiments of the invention is not intended to limit the scope of the invention as claimed, but is merely representative of some embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the embodiments and features and aspects of the embodiments of the present invention may be combined with each other without conflict, and it should be noted that like reference numerals and letters refer to like items in the following figures, and thus, once an item is defined in one figure, it need not be further defined and explained in subsequent figures.
Example (b): referring to fig. 1, a method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis comprises the following steps of preparing materials in step 1, adding alcohol to dissolve in step 2, adjusting alkalinity in step 3, extracting for the first time in step 4, adding acid to reduce in step 5, concentrating under reduced pressure in step 6, extracting for the second time in step 7, concentrating the adjusted acidic upper layer liquid under reduced pressure until no water is distilled off to obtain a primary concentrated solution, and repeating the step 7 to obtain the purification of the secondary concentrated solution.
Step 1, preparing ligusticum wallichii and angelica volatile oil (with ferulic acid content of 0.5-1%), ethanol, NaOH, purified water and hydrochloric acid when preparing materials, step 2, adding alcohol for dissolving to obtain a proper amount of ligusticum wallichii and angelica volatile oil, adding 75-95% of ethanol, fully stirring and dissolving the volatile oil and ethanol in a ratio of 4-1: 1-5 to obtain a mixed solution, step 3, adjusting the pH of the mixed solution to 7-13 by using 1-40% of NaOH solution for adjusting alkalinity, step 4, adding a proper amount of purified water into the mixed solution for adjusting alkalinity for once extraction, standing and separating, step 5, discarding a lower layer solution, adjusting the value of the upper layer solution by using hydrochloric acid, adjusting the pH to 3-6, step 6, concentrating under reduced pressure the adjusted acidic upper layer solution until no water is distilled out to obtain a first concentrated solution, step 7, taking the first concentrated solution as raw oil for twice extraction, repeating the operation of 1-5 once to obtain a second concentrated solution, and 8, concentrating the adjusted acidic upper layer liquid under reduced pressure until no water is distilled off to obtain a primary concentrated liquid, repeating the step 7 to obtain a secondary concentrated liquid, adding a proper amount of 75-100% ethanol to dissolve the secondary concentrated liquid, removing NaCl crystals, concentrating the solution under reduced pressure until no ethanol is distilled off to obtain a ferulic acid crude product with the ferulic acid content of 7-25%.
The working principle is as follows: in the using process, step 1 is carried out when preparing materials, ligusticum wallichii and angelica volatile oil (ferulic acid content is 0.5-1%), ethanol, NaOH, purified water and hydrochloric acid are prepared, step 2 is carried out by adding alcohol to dissolve a proper amount of ligusticum wallichii and angelica volatile oil, 75-95% ethanol is added, the volatile oil is ethanol with the ratio of 4-1: 1-5, the mixture is fully stirred and dissolved to obtain a mixed solution, step 3 is carried out by adjusting the pH of the mixed solution to 7-13 by using 1-40% NaOH solution, step 4 is carried out by adding a proper amount of purified water into the mixed solution for adjusting the alkalinity for one time of extraction, step 5 is carried out by standing and separating to remove the lower layer liquid, the upper layer liquid is adjusted by using hydrochloric acid to adjust the pH to 3-6, step 6 is carried out by carrying out reduced pressure concentration to concentrate the adjusted acidic upper layer liquid until no water is distilled off to obtain a first concentrated liquid, step 7 is carried out by taking the first concentrated liquid as raw oil, and the operation of 1-5 is repeated once, and 8, concentrating the adjusted acidic upper layer liquid under reduced pressure until no water is distilled off to obtain a primary concentrated liquid, repeating the step 7 to obtain a secondary concentrated liquid, dissolving the secondary concentrated liquid in a proper amount of 75-100% ethanol, removing NaCl crystals, concentrating the solution under reduced pressure until no ethanol is distilled off to obtain a ferulic acid crude product with the ferulic acid content of 7-25%.
The above embodiments are only used to illustrate the present invention and not to limit the technical solutions described in the present invention, and although the present invention has been described in detail in the present specification with reference to the above embodiments, the present invention is not limited to the above specific embodiments, and therefore, any modifications or equivalents of the present invention may be made; all such modifications and variations are intended to be included herein within the scope of this disclosure and the appended claims.
Claims (9)
1. A method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis is characterized by comprising the following steps of 1 preparing materials, 2 adding alcohol for dissolving, 3 adjusting alkalinity, 4 extracting for the first time, 5 adding acid for reducing, 6 decompressing and concentrating, 7 extracting for the second time, 8 decompressing and concentrating adjusted acidic upper layer liquid until no water is distilled off to obtain primary concentrated liquid, and repeating the step 7 to obtain purified secondary concentrated liquid.
2. The method as claimed in claim 1, wherein the preparation of the material in step 1 comprises preparing volatile oil of Ligusticum chuanxiong and Angelica sinensis (ferulic acid content 0.5% -1%), ethanol, NaOH, purified water, and hydrochloric acid.
3. The method for separating ferulic acid from ligusticum wallichii and angelica sinensis volatile oil according to claim 1, wherein an appropriate amount of ligusticum wallichii and angelica sinensis volatile oil is dissolved in alcohol in the step 2, 75-95% of ethanol is added, and the ratio of ethanol to the volatile oil is 4-1: 1-5, and the mixture is fully stirred and dissolved to obtain a mixed solution.
4. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein the pH of the mixed solution is adjusted to 7-13 by adjusting the alkalinity in step 3 and using 1-40% NaOH solution.
5. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein the alkaline mixed solution is added with a proper amount of purified water in the step 4 for extraction once, and the mixture is subjected to standing and liquid separation.
6. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein the lower liquid is discarded in step 5, and the upper liquid is adjusted to a value with hydrochloric acid, and the pH value is adjusted to 3-6.
7. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein step 6 is carried out by concentrating under reduced pressure and concentrating the adjusted acidic supernatant under reduced pressure until no water is distilled off, thus obtaining a primary concentrated solution.
8. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein the secondary extraction in step 7 is performed by repeating the operations of 1-5 once by using the primary concentrated solution as raw oil to obtain the secondary concentrated solution.
9. The method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis as claimed in claim 1, wherein in step 8, the adjusted acidic upper layer liquid is concentrated under reduced pressure until no water is distilled off to obtain a primary concentrated solution, the step 7 is repeated to obtain a secondary concentrated solution, a proper amount of 75-100% ethanol is added to dissolve the secondary concentrated solution of the secondary concentrated solution, NaCl crystals are removed, the solution is concentrated under reduced pressure until no ethanol is distilled off to obtain a crude ferulic acid product, and the content of ferulic acid is 7-25%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210725112.8A CN114989006A (en) | 2022-06-23 | 2022-06-23 | Method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210725112.8A CN114989006A (en) | 2022-06-23 | 2022-06-23 | Method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis |
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| CN114989006A true CN114989006A (en) | 2022-09-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202210725112.8A Pending CN114989006A (en) | 2022-06-23 | 2022-06-23 | Method for separating ferulic acid from volatile oil of ligusticum wallichii and angelica sinensis |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1629124A (en) * | 2003-12-18 | 2005-06-22 | 天津科技大学 | Technology for improving extraction rate of ferulic acid in agricultural and by-product and traditional Chinese medicine |
| CN101215265A (en) * | 2008-01-15 | 2008-07-09 | 四川大学 | Method for integrally extracting and purifying ligustrazine, ferulic acid and volatile oil in ligusticum wallichii |
| CN104628553A (en) * | 2013-11-08 | 2015-05-20 | 上海凯鑫分离技术有限公司 | Ferulic acid purification process |
| CN105439864A (en) * | 2015-12-31 | 2016-03-30 | 常州市长宇实用气体有限公司 | Method for extracting high-purity ferulic acid from Szechwan lovage rhizome stems |
| CN107011158A (en) * | 2017-04-06 | 2017-08-04 | 成都众宜坊农业开发有限公司 | A kind of method of extraction purification forulic acid in cauline leaf from Ligusticum wallichii |
-
2022
- 2022-06-23 CN CN202210725112.8A patent/CN114989006A/en active Pending
Patent Citations (5)
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| CN107011158A (en) * | 2017-04-06 | 2017-08-04 | 成都众宜坊农业开发有限公司 | A kind of method of extraction purification forulic acid in cauline leaf from Ligusticum wallichii |
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