CN106278873A - A kind of production technology extracting separation shikimic acid from anise - Google Patents
A kind of production technology extracting separation shikimic acid from anise Download PDFInfo
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- CN106278873A CN106278873A CN201610688401.XA CN201610688401A CN106278873A CN 106278873 A CN106278873 A CN 106278873A CN 201610688401 A CN201610688401 A CN 201610688401A CN 106278873 A CN106278873 A CN 106278873A
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- acid
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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
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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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/445—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by steam distillation
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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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Abstract
Disclosed by the invention a kind of extracting the production technology separating shikimic acid from anise, its technological process is: anistree → straight-through steam steam oil → countercurrent extraction → disk centrifugal → ceramic membrane clarification → ion exchange resin purification → membrance separation decolouring → reverse osmosis membrane concentration → macroporous adsorbent resin decolours → be concentrated in vacuo cream processed → crystallize and wash → be vacuum dried.This technique solves problem present in production and processing Illicillm Verum Fruit, has with short production cycle, and the effective ingredient response rate is high, and production technology is simple, and automaticity is high, and production cost is low waits remarkable advantage.
Description
Technical field
The present invention relates to medication chemistry, plant extract, a kind of production work extracting separation shikimic acid from anise
Skill.
Background technology
Shikimic acid, has another name called shihimic acid, is a kind of important organic acid present in nature, plants at Magnoliaceae Illicium
In the fruit of thing Fructus Anisi Stellati, content is higher.
Chinese: shikimic acid
Chinese another name 3,4,5-trihydroxy-1-cyclohexene-1-formic acid
English name: Shikimic Acid
English another name 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid; Shikimicacid;
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid; (-)-Shikimic acid
CAS NO. 138-59-0
Shikimic acid is white fine powder, soluble in water, and the dissolubility in water is 18g/100ml, is insoluble in chloroform, benzene and stone
The organic solvents such as oil ether.Fusing point 185 DEG C～191 DEG C, optical rotation-180 °, abnormal smells from the patient octanoic acid.Due in molecular structure containing 3-
Hydroxyl, 1 carboxyl, 1 double bond, thus shikimic acid can become ester, it is also possible to become salt, there is no strong oxidizing property.
Chemical formula: 3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
Molecular formula C7H10O5
Molecular weight 174.15
Its molecular structural formula is as follows:
Shikimic acid Shikimic Acid
The extractive technique of shikimic acid: the more extraction process of reported in literature has solvent extraction method, water bath reflux method, water vapour to steam
Evaporate extraction, homogenate extraction method, microwave-assisted extraction, ultrasonic assistant extraction method etc., research and develop the most again absorption
The extractive techniques such as method, decompression interior boiling method, biological fermentation process.
The isolation technics of shikimic acid: study at present more separation purifying technique have Ultra filtration membrane method, silica gel column chromatography,
The separating and purifying technologies such as molecular imprinting, ion-exchange resin purification, organic solvent extractionprocess, recrystallization method.This separation
The deficiency of extractive technique is: cost is high, and the production cycle is long, and loss of effective components is big, and the problem of most critical is that related data cannot
Reappear.
Summary of the invention
The invention aims to provide a kind of production technology extracted from anise and separate shikimic acid, this technique solves
Problem present in production and processing Illicillm Verum Fruit, has with short production cycle, and the effective ingredient response rate is high, production technology letter
Single, automaticity is high, and production cost is low waits remarkable advantage.
The technical scheme realizing the object of the invention is:
A kind of production technology extracting separation shikimic acid from anise, comprises the steps:
(1) straight-through steam steam oil: take anistree dry fruit, put in special anise tree volatile oil alembic, opens straight-through steam
Steam oil, the special container collection of distillation gained anise tree volatile oil, after steam oil, the remaining anise that deoils is moved on in countercurrent extraction groove；
(2) countercurrent extraction: anistree input in countercurrent extraction groove of deoiling, and add in groove anistree weight 3.0 times of deoiling from
Water, countercurrent extraction；After having extracted, filtered by countercurrent extraction groove special medicinal residues filter, obtain countercurrent extraction liquid；
(3) disk centrifugal: countercurrent extraction liquid is crossed disk centrifugal separator, removes major part pectin and turbid material, obtains centrifugal liquid；
(4) ceramic membrane clarification: centrifugal liquid is crossed the clarification of ceramic membrane complete set of equipments, obtains the ceramic membrane filtrate of clear；
(5) ion exchange resin purifies: ceramic membrane filtrate loads the chromatographic column filling anion exchange resin, enters purification washing
Post, until chromatographic column effluent liquid achromaticity and clarification is transparent only；With 3% dilute sulfuric acid or 5% formic acid solution desorbing, what desorbing was sour enters cylinder
Amass 3 times for weight resin, be to start in the of 6 to collect from effluent pH, enter to receive the most completely during desorbing acid whole afterwards
Collection；Continuing into purified water after having entered desorbing acid, purified water effluent now is collected in the lump, collect to effluent pH be 5 only；Close
The effluent of desorbing acid process of going forward side by side and enter pure water and wash the effluent of acid, obtains chromatographic solution；
(6) membrance separation decolouring: chromatographic solution enters the organic membrane complete set of equipments that membrane molecule interception is 300, removes molecular weight and is more than
The pigment of 300, collection membrane separates the permeate of decolouring, obtains film destaining solution；
(7) reverse osmosis membrane concentrates: film destaining solution is entered reverse osmosis membrane complete set of equipments and carries out membrance concentration, obtain membrance concentration liquid.
(8) macroporous adsorbent resin decolouring: membrance concentration liquid is put into the chromatographic column filling macroporous adsorbent resin, opens from charging
Begin to collect, after charging, add the purified water of resin volume 3 times, be merged into material effluent and enter purified water effluent, obtaining tree
Fat destaining solution；
(9) processed cream is concentrated in vacuo: resin decolorization liquid is entered interior circulation decompression concentrator cream, obtains condensed cream.
(10) crystallize and wash: condensed cream being placed more than 12h in-5 DEG C ~ 2 DEG C freezers, separates out a large amount of off-white color crystal,
Mutually form bulky grain or in bulk；Block is crushed, then granular crystals and broken block sucking filtration, obtains white crystals, then to sucking filtration
Precipitation adds the washing of a small amount of purified water and sucking filtration again, obtains the crystallization of pure white shikimic acid；
(11) vacuum drying: by the crystallization vacuum drying of white shikimic acid, obtain content >=98%, the shikimic acid product of white.
The heating vapor (steam) temperature of the described straight-through steam steam oil of step (1): 130 ~ 150 DEG C；Steam oil time: 7.0 ~ 8.0h.
The heating vapor (steam) temperature of step (2) described countercurrent extraction: 120 ~ 150 DEG C；Solution temperature: >=98 DEG C, keeps micro-boiling
State；Countercurrent extraction time: 3.0h.
Anion exchange resin described in step (5) is 201 × 7 types, or the moon of 201 × 7FC type or 201 × 7MB type from
Sub-exchange resin, charge ratio is that every 1000kg deoils anistree raw material correspondence 1000kg anion exchange resin；What desorbing was sour enters post
Volume is 1000kg anion exchange resin desorbing acid 3000L.
Step (7) described membrance concentration is that film destaining solution is concentrated into the 1/5 ~ 1/6 of original volume.
The model of step (8) described macroporous adsorbent resin is: D101 type or AB-8 type or DM130 type macroporous absorption tree
Fat, charge ratio is that every 1000kg deoils anistree raw material correspondence 250kg macroporous adsorbent resin；
Step (9) described concentration cream processed is that resin decolorization liquid is concentrated into more than 30 Baumes.
The invention has the beneficial effects as follows:
(1) this technique solves problem present in production and processing Illicillm Verum Fruit, has with short production cycle, and effective ingredient returns
Yield is high, and production technology is simple, and automaticity is high, and production cost is low waits remarkable advantage；
(2) according to the chemical composition feature of Fructus Anisi Stellati, being clarified by ceramic membrane separation, ion exchange resin purifies, macroporous absorption
The crucial industry link that produces such as resin decolorization effectively combines, and industrialized mass production has gone out shikimic acid >=98%, color is white
The high-quality star anise extract of color.
Accompanying drawing explanation
Fig. 1 is the process chart of embodiment.
Detailed description of the invention
The invention will be further elaborated with embodiment below in conjunction with the accompanying drawings, but is not the restriction to present invention.
Embodiment 1:
Extracting, as it is shown in figure 1, a kind of, the production technology separating shikimic acid from anise, its technological process is:
Anistree → straight-through steam steam oil → countercurrent extraction → disk centrifugal → ceramic membrane clarification → ion exchange resin purification → film
Separate decolouring → reverse osmosis membrane concentration → macroporous adsorbent resin to decolour → be concentrated in vacuo cream processed → crystallize and wash → be vacuum dried.
Specifically include following steps:
1) straight-through steam steam oil
Take anistree dry fruit 1000kg, put in special anise tree volatile oil alembic, open straight-through steam steam oil.Heating is steamed
Stripping temperature: 140 DEG C；Steam oil time: 7.5h.Distillation gained anise tree volatile oil special container is collected, and remaining after steam oil deoils
Anise is moved on in countercurrent extraction groove；
2) countercurrent extraction
To deoil in anistree input countercurrent extraction groove, during extracting, in groove, constantly add the tap water of 3000L altogether, countercurrently
Extract.Heating vapor (steam) temperature: 130 DEG C；Solution temperature: >=98 DEG C, keeps slight boiling condition；Countercurrent extraction time: 3.0h.Extract
After, filtered by countercurrent extraction groove special medicinal residues filter, obtain countercurrent extraction liquid；
3) disk centrifugal
Countercurrent extraction liquid is crossed disk centrifugal separator, removes major part pectin and turbid material, obtain centrifugal liquid；
4) ceramic membrane clarification
Centrifugal liquid is crossed the clarification of ceramic membrane complete set of equipments, obtains the ceramic membrane filtrate of clear；
5) ion exchange resin purifies
Ceramic membrane filtrate is entered equipped with weight 1000kg, the chromatographic column of specification 201 × 7 type anion exchange resin.Entered material with
After, enter purification washing post, until chromatographic column effluent liquid achromaticity and clarification is transparent only.Then with 3% dilution heat of sulfuric acid 3000L desorbing.From
Effluent pH is 6 to start to collect, and enters to collect the most completely during desorbing acid whole afterwards.Continue after having entered desorbing acid
Entering purified water, purified water effluent now is collected in the lump, collect to effluent pH be 5 only；It is merged into the stream of desorbing acid process
Go out liquid and enter pure water wash acid effluent, obtain chromatographic solution；
6) membrance separation decolouring
Chromatographic solution is entered the organic membrane complete set of equipments that membrane molecule interception is 300, removes the molecular weight pigment more than 300, collect
The permeate of membrance separation decolouring, obtains film destaining solution；
7) reverse osmosis membrane concentrates
Film destaining solution is entered reverse osmosis membrane complete set of equipments and carries out membrance concentration, be concentrated into the 1/5 ~ 1/6 of original volume, about 600L, obtain film
Concentrated solution；
8) macroporous adsorbent resin decolouring
Membrance concentration liquid is entered equipped with weight 250kg, the chromatographic column of specification D101 type macroporous adsorbent resin.Start to receive from charging
Collection, after having entered material, enters 750L purified water, and effluent now is collected in the lump；It is merged into material effluent and enters purification current
Go out liquid, obtain resin decolorization liquid；
9) processed cream is concentrated in vacuo
Resin decolorization liquid is entered interior circulation decompression concentrator cream, is concentrated into 30 Baumes, obtains condensed cream；
10) crystallize and wash
Condensed cream is placed more than 12h in-5 DEG C ~ 2 DEG C freezers, i.e. separates out a large amount of off-white color crystal, mutually form bulky grain or one-tenth
Block.Block is crushed, then granular crystals and broken block sucking filtration, obtains white crystals, then add the washing of a small amount of purification to sucking filtration precipitation
Wash and sucking filtration again, obtain the crystallization of pure white shikimic acid；
11) vacuum drying
By the crystallization vacuum drying of white shikimic acid, obtain content 98.27%, the shikimic acid product 56.5kg of white.
Embodiment 2
From anise, extract, as it is shown in figure 1, a kind of, the production technology separating shikimic acid, comprise the steps:
1) straight-through steam steam oil
Take anistree dry fruit 1000kg, put in special anise tree volatile oil alembic, open straight-through steam steam oil.Heating is steamed
Stripping temperature: 130 DEG C；Steam oil time: 8.0h.Distillation gained anise tree volatile oil special container is collected, and remaining after steam oil deoils
Anise is moved on in countercurrent extraction groove；
2) countercurrent extraction
To deoil in anistree input countercurrent extraction groove, during extracting, in groove, constantly add the tap water of 3000L altogether, countercurrently
Extract.Heating vapor (steam) temperature: 125 DEG C；Solution temperature: >=98 DEG C, keeps slight boiling condition；Countercurrent extraction time: 3.0h.Extract
After, filtered by countercurrent extraction groove special medicinal residues filter, obtain countercurrent extraction liquid；
3) disk centrifugal
Countercurrent extraction liquid is crossed disk centrifugal separator, removes major part pectin and turbid material, obtain centrifugal liquid；
4) ceramic membrane clarification
Centrifugal liquid is crossed the clarification of ceramic membrane complete set of equipments, obtains the ceramic membrane filtrate of clear；
5) ion exchange resin purifies
Ceramic membrane filtrate is entered equipped with weight 1000kg, the chromatographic column of specification 201 × 7MB type anion exchange resin.Enter material
After, enter purification washing post, until chromatographic column effluent liquid achromaticity and clarification is transparent only.Then with 5% formic acid solution 3000L desorbing.From
Effluent pH is 6 to start to collect, and enters to collect the most completely during desorbing acid whole afterwards.Continue after having entered desorbing acid
Entering purified water, purified water effluent now is collected in the lump, collect to effluent pH be 5 only；It is merged into the stream of desorbing acid process
Go out liquid and enter pure water wash acid effluent, obtain chromatographic solution；
6) membrance separation decolouring
Chromatographic solution is entered the organic membrane complete set of equipments that membrane molecule interception is 300, removes the molecular weight pigment more than 300, collect
The permeate of membrance separation decolouring, obtains film destaining solution；
7) reverse osmosis membrane concentrates
Film destaining solution is entered reverse osmosis membrane complete set of equipments and carries out membrance concentration, be concentrated into the 1/5 ~ 1/6 of original volume, about 600L, obtain film
Concentrated solution；
8) macroporous adsorbent resin decolouring
Membrance concentration liquid is entered equipped with weight 250kg, the chromatographic column of specification AB-8 type macroporous adsorbent resin.Start to receive from charging
Collection, after having entered material, enters 750L purified water, and effluent now is collected in the lump；It is merged into material effluent and enters purification current
Go out liquid, obtain resin decolorization liquid；
9) processed cream is concentrated in vacuo
Resin decolorization liquid is entered interior circulation decompression concentrator cream, is concentrated into 31 Baumes, obtains condensed cream；
10) crystallize and wash
Condensed cream is placed more than 12h in-5 DEG C ~ 2 DEG C freezers, i.e. separates out a large amount of off-white color crystal, mutually form bulky grain or one-tenth
Block.Block is crushed, then granular crystals and broken block sucking filtration, obtains white crystals, then add the washing of a small amount of purification to sucking filtration precipitation
Wash and sucking filtration again, obtain the crystallization of pure white shikimic acid.
11) vacuum drying
By the crystallization vacuum drying of white shikimic acid, obtain content 98.30%, the shikimic acid product 56.2kg of white.
Claims (8)
1. from anise, extract the production technology separating shikimic acid, it is characterized in that: comprise the steps:
(1) straight-through steam steam oil: take anistree dry fruit, put in special anise tree volatile oil alembic, opens straight-through steam
Steam oil, the special container collection of distillation gained anise tree volatile oil, after steam oil, the remaining anise that deoils is moved on in countercurrent extraction groove；
(2) countercurrent extraction: anistree input in countercurrent extraction groove of deoiling, and add in groove anistree weight 3.0 times of deoiling from
Water, countercurrent extraction；After having extracted, filtered by countercurrent extraction groove special medicinal residues filter, obtain countercurrent extraction liquid；
(3) disk centrifugal: countercurrent extraction liquid is crossed disk centrifugal separator, removes major part pectin and turbid material, obtains centrifugal liquid；
(4) ceramic membrane clarification: centrifugal liquid is crossed the clarification of ceramic membrane complete set of equipments, obtains the ceramic membrane filtrate of clear；
(5) ion exchange resin purifies: ceramic membrane filtrate loads the chromatographic column filling anion exchange resin, enters purification washing
Post, until chromatographic column effluent liquid achromaticity and clarification is transparent only；With 3% dilute sulfuric acid or 5% formic acid solution desorbing, what desorbing was sour enters cylinder
Amass 3 times for weight resin, be to start in the of 6 to collect from effluent pH, enter to receive the most completely during desorbing acid whole afterwards
Collection；Continuing into purified water after having entered desorbing acid, purified water effluent now is collected in the lump, collect to effluent pH be 5 only；Close
The effluent of desorbing acid process of going forward side by side and enter pure water and wash the effluent of acid, obtains chromatographic solution；
(6) membrance separation decolouring: chromatographic solution enters the organic membrane complete set of equipments that membrane molecule interception is 300, removes molecular weight and is more than
The pigment of 300, collection membrane separates the permeate of decolouring, obtains film destaining solution；
(7) reverse osmosis membrane concentrates: film destaining solution is entered reverse osmosis membrane complete set of equipments and carries out membrance concentration, obtain membrance concentration liquid；
(8) macroporous adsorbent resin decolouring: membrance concentration liquid is put into the chromatographic column filling macroporous adsorbent resin, starts to receive from charging
Collection, adds the purified water of resin volume 3 times after charging, be merged into material effluent and enter purified water effluent, obtains resin and takes off
Color liquid；
(9) processed cream is concentrated in vacuo: resin decolorization liquid is entered interior circulation decompression concentrator cream, obtains condensed cream；
(10) crystallize and wash: condensed cream being placed more than 12h in-5 DEG C ~ 2 DEG C freezers, separates out a large amount of off-white color crystal, mutually
Form bulky grain or in bulk；Block is crushed, then granular crystals and broken block sucking filtration, obtains white crystals, then precipitate to sucking filtration
Add the washing of a small amount of purified water and sucking filtration again, obtain the crystallization of pure white shikimic acid；
(11) vacuum drying: by the crystallization vacuum drying of white shikimic acid, obtain content >=98%, the shikimic acid product of white.
Production technology the most according to claim 1, is characterized in that: the described straight-through steam steam oil of step (1) add vapours
Temperature: 130 ~ 150 DEG C；Steam oil time: 7.0 ~ 8.0h.
Production technology the most according to claim 1, is characterized in that: the heating vapor (steam) temperature of step (2) described countercurrent extraction:
120~150℃；Solution temperature: >=98 DEG C, keeps slight boiling condition；Countercurrent extraction time: 3.0h.
Production technology the most according to claim 1, is characterized in that: the anion exchange resin described in step (5) is 201 ×
7 types or 201 × 7FC type or the anion exchange resin of 201 × 7MB type, charge ratio is that every 1000kg anistree raw material that deoils is corresponding
1000kg anion exchange resin.
Production technology the most according to claim 1, is characterized in that: the column volume that enters of step (5) described desorbing acid is
1000kg anion exchange resin: desorbing acid 3000L.
Production technology the most according to claim 1, is characterized in that: step (7) described membrance concentration is to be concentrated by film destaining solution
To original volume 1/5 ~ 1/6.
Production technology the most according to claim 1, is characterized in that: the model of step (8) described macroporous adsorbent resin is
D101 type or AB-8 type or DM130 type macroporous adsorbent resin, charge ratio is that every 1000kg deoils anistree raw material correspondence 250kg macropore
Adsorbent resin.
Production technology the most according to claim 1, is characterized in that: step (9) described concentration cream processed is by resin decolorization liquid
It is concentrated into more than 30 Baumes.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232239A (en) * | 2018-09-30 | 2019-01-18 | 那坡康正天然植物提取有限责任公司 | A kind of extraction process of shikimic acid |
| CN111278799A (en) * | 2017-08-24 | 2020-06-12 | 一般社团法人八角平和计画研究所 | Process for producing shikimic acid |
| CN111548265A (en) * | 2020-06-16 | 2020-08-18 | 南通科兴石墨设备有限公司 | High-efficiency shikimic acid concentration process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101371700A (en) * | 2008-09-17 | 2009-02-25 | 中国科学院广州化学研究所 | Method for unitedly extracting anise tree volatile oil and shikimic acid crude extract |
| CN101391951A (en) * | 2007-09-18 | 2009-03-25 | 兴化格林生物制品有限公司 | Production preparation process of high-purity shikimic acid |
| CN102584571A (en) * | 2011-11-21 | 2012-07-18 | 河南孟成生物药业股份有限公司 | Extraction process for shikimic acid in fermentation liquor |
| CN103145550A (en) * | 2013-03-27 | 2013-06-12 | 张达燕 | Method of extracting shikimic acid from star anise |
-
2016
- 2016-08-19 CN CN201610688401.XA patent/CN106278873A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101391951A (en) * | 2007-09-18 | 2009-03-25 | 兴化格林生物制品有限公司 | Production preparation process of high-purity shikimic acid |
| CN101371700A (en) * | 2008-09-17 | 2009-02-25 | 中国科学院广州化学研究所 | Method for unitedly extracting anise tree volatile oil and shikimic acid crude extract |
| CN102584571A (en) * | 2011-11-21 | 2012-07-18 | 河南孟成生物药业股份有限公司 | Extraction process for shikimic acid in fermentation liquor |
| CN103145550A (en) * | 2013-03-27 | 2013-06-12 | 张达燕 | Method of extracting shikimic acid from star anise |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111278799A (en) * | 2017-08-24 | 2020-06-12 | 一般社团法人八角平和计画研究所 | Process for producing shikimic acid |
| CN109232239A (en) * | 2018-09-30 | 2019-01-18 | 那坡康正天然植物提取有限责任公司 | A kind of extraction process of shikimic acid |
| CN111548265A (en) * | 2020-06-16 | 2020-08-18 | 南通科兴石墨设备有限公司 | High-efficiency shikimic acid concentration process |
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