CN107235840A - A kind of method of the chlorogenic acid extracting from coffee bean and tannin - Google Patents
A kind of method of the chlorogenic acid extracting from coffee bean and tannin Download PDFInfo
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- CN107235840A CN107235840A CN201710583043.0A CN201710583043A CN107235840A CN 107235840 A CN107235840 A CN 107235840A CN 201710583043 A CN201710583043 A CN 201710583043A CN 107235840 A CN107235840 A CN 107235840A
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- coffee bean
- tannin
- chlorogenic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
Abstract
The present invention relates to a kind of method that high-purity chlorogenic acid and tannin are extracted from coffee bean, ether defatting processing is carried out to coffee bean, using water extraction, macroporous absorbent resin is crossed in ultrafiltration, concentration, ethyl acetate is extracted, reversed phase column chromatography, decolorizing with activated carbon, ethyl acetate is crystallized and high purity ethanol recrystallization, obtains chlorogenic acid and tannin sterling.It is combined using ether defatting with water extraction, can inactivates protein denaturation in coffee bean, can prevent tannin from hydrolyzing again.The viscosity of its leaching liquor can be greatly reduced using ungrease treatment, the rate of filtration is improved, a large amount of lipid materials can be obtained again, production cost is reduced.
Description
Art
The present invention relates to a kind of method that high-purity chlorogenic acid and tannin are extracted from coffee bean, belong to natural product chemistry
Technical field.
Background technology
Chlorogenic acid, alias：Chlorogenic acid, caffeotannic acid, (1S, 3R, 4R, 5R) -3- [[3- (3,4- dihydroxy phenyl) -1- oxygen
Generation -2- acrylic] oxygen] -1,4,5- trihydroxy naphthenic acids；System name：1,3,4,5- tetrahydroxy cyclohexane-carboxylic acid-(3,4-
Dihydroxycinnamic acid ester)；Chemical name：CA (3-O-caffeoylquinic acid), plant origin：For
Caprifoliaceae plant honeysuckle Lonicera japonica Thumb., lonicera hypoglauca miq Lonicera hypoglauca Miq., mountain silver
Flower Lonicera confusa DC. or hair style honeysuckle Lonicera dasytyla Rehd. dry flower or with just opening
In flower and folium cortex eucommiae.Chlorogenic acid semihydrate is white or slightly yellow acicular crystal, is changed into anhydride at 110 DEG C, with dilute salt
Heat produces caffeic acid, 208 DEG C of fusing point, specific rotatory power [α] 2 ° of D=35 (C=28) to acid altogether.Chlorogenic acid dissolves at 25 DEG C in water
Degree about 4%, be soluble in ethanol, acetone, methanol polar solvent, be slightly soluble in ethyl acetate, be insoluble in chloroform, ether,
The lipophylic organic solvents such as benzene.Chlorogenic acid is that have ester bond, unsaturation in the ester formed by caffeic acid and chinic acid, its molecular structure
Three l fractions of double bond and polyhydric phenols.During plant extract, often through hydrolysis and the migration of intramolecular ester group
Generation isomerization.Due to the special construction of chlorogenic acid, determine that it can utilize ethanol, acetone, methanol polar solvent from plant
Extracted in thing, but be due to the unstability of chlorogenic acid in itself, high temperature, strong light and long-time heating are unable to during extraction.It is green
The test liquid of ortho acid is positioned over when brown bottle, (2 DEG C) of refrigerator are preserved to be stablized the most.Chlorogenic acid be considered as numerous medicinal materials and it is middle into
The principle active component of medicine antibacterial and detoxicating, anti-inflammatory and choleretic, is normally used as qualitative or even quantitative index.It is reported that chlorogenic acid
Primary bioactivity have the inhibitory action of (1) to hyaluronidase and G-6-Pase；(2) to the removing of free radical
And lipoid peroxidization resistant；(3) antimutagenesis；(4) hepatic cholagogic is acted on；(5) antibacterial, antiviral and spasmolysis etc. are acted on.
It can be inactivated with wide antibacterial action, but in vivo by protein.It is similar to caffeic acid, during oral or intraperitoneal injection, it can carry
The central excitatory of high rat.The small bowel peristalsis and the tension force of rat uterus of rat and mouse can be increased.There is choleretic effect, can increase
Enter the choleresis of rat.Have to people after sensitization, plant dust of the suction containing this product, can occur asthma, dermatitis etc., but
It can be acted on after eating through intestinal secretion thing, be changed into no allergenic substance.There is hemostasis, increase white blood cell and antivirus action.Have
Shorten blood clotting and the effect in bleeding time.
Chlorogenic acid is widely present in plant, and only content is more in several plant, such as honeysuckle, such as sunflower seeds, gold and silver
In floral leaf, coffee bean, Acer truncatum leaves, burdock leaf, sweet potato leaves, its content is in 1%~8% butt or so, its content of different sources
Also different, contained chlorogenic acid isomers species is also different, and the chlorogenic acid from different plants pharmacological action not yet
Equally.
Coffee nutritional ingredient：2.2 grams of moisture content, 12.6 grams of protein, fatty 16 grams, carbohydrate in every 100 grams of coffee beans
46.7 grams, 9 grams of cellulose, 4.2 grams of ash content, 120 milligrams of calcium, 170 milligrams of phosphorus, 42 milligrams of iron, 3 milligrams of sodium, vitamin B2 0.12
Gram, 3.5 milligrams of nicotinic acid, 1.3 grams of caffeine, 8 grams of tannin.
The moisture of coffee bean has very big difference with different processing stages and product, the moist coffee bean containing shell
Moisture be about 50 ﹪, and the fresh coffee beans of drying are about the ﹪ of 10 ﹪~13.Though content of the mineral matter in coffee bean compared with
It is few, 4 ﹪ of fresh coffee beans dry matter are accounted for, but it is critically important.It contains a variety of different elements, wherein using the content of potassium as most
It is many, 40 ﹪ of all mineral qualities are accounted for, are secondly calcium, magnesium, phosphorus, sodium and sulphur etc..It is other still to have many contents in PPM levels
Trace element, such as zinc, manganese, copper, more than 33 kinds of rubidium.Sucrose is topmost free state carbohydrate in fresh coffee beans, its content according to
Kind, source and maturity and it is different.Polysaccharide is critically important group composition in fresh coffee beans, account for dry amount 40%~
50 ﹪.In terms of crude protein, the ﹪ of the ﹪ of fresh coffee beans content about 13~16, if deducting the nitrogen-containing compound such as caffeine and trigonelline,
The content of real protein is about the ﹪ of 8.8 ﹪~9.7.It is also disorderly containing a variety of ferment in fresh coffee beans, such as lipase, albumen
Matter amylase, carbohydrate amylase, galactose on hydrolysis ferment and peroxidating ferment etc..Fresh coffee beans about containing 0.15 ﹪~
0.25 ﹪ free amino acid.The isomeric compound that at least more than 3 kinds of chlorogenic acid is present, and its function essentially consists in coffee plant physiology
Regulation.The lipid of fresh coffee beans is by the caffeol that is present in endosperm and is present in what the wax of coffee bean outer layer was constituted, coffee
The average content of coffee beans is 15 ﹪ of dry amount.Also contain vegetable soda, trigonelline, niacin.
The content of tannin is very high in coffee bean, reaches 8% or so.Tannin is the compound of high polymeric in polyphenol, they
The compound of water can be insoluble in protein and digestive ferment formation, assimilating for food is influenceed.Hydrolysable Tannins and contracting can be divided into
And tannin, both often coexist.The latter is also referred to as proanthocyanidin, and the tannin content in Quan Gu, beans is more.
Tannin is also known as tannic acid, tannin, is present in a variety of trees (such as rubber tree and lacquer tree)) bark and fruit in,
It is the main component in the insect gall that these trees are generated by insect infestations, content is up to 50%~70%.Tannin be yellow or
The amorphous bulky powder of brown color, in atmosphere color gradually deepen, have strong hygroscopicity；It is readily soluble insoluble in ether, benzene, chloroform
Yu Shui, ethanol, acetone, the aqueous solution have astringent taste.Tannin is not single compound, and chemical composition is more complicated, is broadly divided into two
Kind, one kind is condensed tannin, is the 2nd of flavanols in flavane 01 derivatives, molecule by C-C keys and catechol or benzenetriol
With reference to.One kind is that have ester bond in hydrolyzable tannin, molecule, is the gallate of glucose, another is conventional list
Rather.Tannin is only used for tanning hide by our people for a long time makes it be converted into leather.From after 1950s, tannin can be with
Protein, polysaccharide, alkaloid, microorganism, enzyme, the activity of metal ion reaction and the anti-oxidant of it, seizure free radical, suppression
After bacterium, the behavior of derivative reaction are revealed, its application prospect and scope expand rapidly.It adds in food processing, fruits and vegetables at present
Important breakthrough is obtained in terms of work, storage, medicine and water process, it has in Beer Brewage than Chinese tannin in recent years
More preferable security.
A kind of coffee bean processing of chlorogenic acid-rich of Publication No. CN1813556A Introduction To Cn Patent
Method, green coffee is roasted and decocts the coffee bean processing method that processing prepares roasted coffee beans, high-temperature, high pressure fluid is given birth to coffee
Beans contact implements roasting and decocts processing.
A kind of chlorogenic acid of Publication No. CN101404891A Introduction To Cn Patent contains the manufacture method of thing, by coffee
Coffee beans extract (A) and water Combination organic solvent (B) and the mixture of water (C), make with (A) mixed (B)/(C's)
Mass ratio reaches be in contact under conditions of 70/30~99.5/0.5 after, reclaim solid part.It can be obtained by easy method
The different chlorogenic acid being reduced of smelling of peculiar smell contains thing.
A kind of method for extraction and purification of Chlorogenic Acid of Flos Lonicerae of Publication No. CN1425643 Introduction To Cn Patent：It is dry
Honeysuckle is crushed, and carries out secondary back extraction to honeysuckle using Diluted Alcohol, concentrated extract is pure with the preliminary removal of impurities of flocculence again
Change, it is finally refined using Amberlyst process or acid ethyl acetate extraction purifying.
Publication No. CN1616403 Introduction To Cn Patent extraction prepares chlorogenic acid from honeysuckle technique：Gold and silver
Flower is added water or ethanol carries out refluxing extraction, and filtrate and recycling design, plus ethanol precipitation impurity are collected in filtering, and overnight, filtering subtracts
Recycling design is pressed, adds water appropriate, stands overnight, filter, macroporous resin column on filtrate is concentrated with eluant, eluent, is collected and is contained green original
The component of acid, upper polyamide column with eluent, collects the component containing chlorogenic acid, concentration is refining to obtain content and is more than
95% chlorogenic acid.
A kind of technique of the chlorogenic acid extracting from honeysuckle of Publication No. CN1199728 Introduction To Cn Patent：Gold and silver
Plus acidic ethanol immersion certain time is spent, heating and refluxing extraction certain time, Plus acidic alcohol reflux extracts a timing to the dregs of a decoction again
Between, merge decoction, ethanol is recovered under reduced pressure, concentrate, refine.
Current high-quality coffee bean is mainly used in processing coffee, wherein there is most such as dead beans not obtain very
Coffee is directly carried stock sentimental taste by dead beans by good utilisation using meeting, and dead beans contain higher tanning matter.If by this portion
Divide coffee bean to be made full use of, plantation income can be greatly improved.Chlorogenic acid extracting is directly carried out using coffee bean sour water in addition,
Due to containing a large amount of lipid materials in coffee bean, it will the extraction of influence chlorogenic acid.
The content of the invention
It is an object of the invention to overcome the deficiency of prior art and to provide a kind of rational technology, simple to operate, technique all
Phase is short, coffee bean comprehensive utilization degree high, the production technology of rapid extraction chlorogenic acid and tannin.
The technical solution adopted by the present invention includes：Ether defatting processing is carried out to coffee bean, using water extraction, ultrafiltration is excessive
Macroporous adsorbent resin, concentration, ethyl acetate extraction, reversed phase column chromatography, decolorizing with activated carbon, ethyl acetate crystallization and high purity ethanol weight
Crystallization, obtains chlorogenic acid and tannin sterling.
Therefore, the present invention provides a kind of method from coffee bean chlorogenic acid extracting and tannin, and specific steps include as follows：
(1) dried coffee bean is crushed to the mesh of 10 mesh~20, is added ether and is carried out cold soaking and carries 3~4 hours, its
The weight kg of middle coffee bean and the volume L ratios of ether are 1:7~15；
(2) ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, will contain diethyl ether solution and carry out at 40~50 DEG C
Under be concentrated under reduced pressure, reclaim ether, and obtain coffee bean fat；
(3) water is added to coffee bean residue, room temperature extraction, the time is 3~5h, wherein coffee bean residue weight kg and water
Volume L ratios be 1:5~10；
(4) ceramic membrane filter once obtains filtrate I, uses ultrafilter (molecular cut off is 500) to carry out being concentrated to give concentrate I
With filtrate II；
(5) by AB-8 macroporous absorbent resins on concentrate I, after absorption 30min, with the purifying water elution of 1BV upper prop liquid, abandon
Eluent, then eluted with the pH value of 3BV upper prop liquid for 6,30% ethanol water, ethanol eluate I is collected, original volume is concentrated into
1/10~1/25, obtain concentrate II；
(6) by AB-8 macroporous absorbent resins on filtrate II, (contained for 2,40% ethanol elution with the pH value of 3BV upper prop liquid
0.01mol/L hydrochloric acid), ethanol eluate II is collected, the 1/10~1/20 of original volume is concentrated into, obtains concentrate III；
(7) concentrate II is directly cooled to 1~4 DEG C of crystallization 8h, filters to obtain coarse crystallization, then after recrystallization coffee tannin
Sterling；
(8) 6000rpm is carried out to concentrate III and centrifuges 10~20min, obtain supernatant, supernatant is with two to three times volume
Ethyl acetate is collected the extract that ethyl acetate is contained on upper strata, is concentrated under reduced pressure at 40~50 DEG C, reclaim acetic acid to extracting
Ethyl ester, and obtain chlorogenic acid pure product.
The filter process is all to use ceramic membrane filter, and fenestra pore size is 0.22 μm.
The concentration process is all to use to be concentrated under reduced pressure, and temperature control is between 40~55 DEG C.
Technique effect
1st, recrystallized at ambient temperature using ethyl acetate, chlorogenic acid content is reached highest.
2nd, coffee bean Content of Chlorogenic Acid is high, and the coffee bean chlorogenic acid content of Yunnan Province is up to 14%, and price is low.Make
With replacement of the coffee bean as medicinal materials such as honeysuckle, folium cortex eucommiaes, the utilization ratio of the residues such as coffee bean is both substantially increased, is improved
The added value of coffee bean, broken away from the dependence of the medicinal materials such as honeysuckle, folium cortex eucommiae again, and complete incidence graph market is to honeysuckle, the bark of eucommia
The wilderness demand of the medicinal materials such as leaf, extends the medicinal source resource that chlorogenic acid extracts raw material.
3rd, the present invention uses ether defatting and water extraction method, can inactivate protein denaturation in coffee bean, can prevent again
Tannin is hydrolyzed.
4th, the viscosity of its leaching liquor can be greatly reduced using ungrease treatment, the rate of filtration is improved, can obtain a large amount of again
Lipid material, reduces production cost.
Embodiment
With reference to specific embodiment, the invention will be further described, following examples be intended to illustrate invention rather than
Limitation of the invention further.
Embodiment 1
Weigh 100kg coffee beans, progress is crushed to the mesh of 10 mesh~20, add 800L ether and carry out cold soaking to carry 3~4 small
When；Ceramic membrane filter once coffee bean residue and containing diethyl ether solution, will contain diethyl ether solution depressurized at 40~50 DEG C it is dense
Contracting, reclaims ether, and obtain coffee bean fat 15.4kg；Coffee bean residue is added to 500L water, room temperature is extracted, and the time is 4h,
Ceramic membrane filter once obtains filtrate I, uses ultrafilter (molecular cut off is 500) to carry out being concentrated to give 20L concentrates I and 60L filters
Liquid II, by AB-8 macroporous absorbent resins on concentrate I, adsorbs after 30min, with the purifying water elution of 1BV upper prop liquid, abandons elution
Liquid, then eluted with the pH value of 3BV upper prop liquid for 6,30% ethanol water, 220L ethanol eluates I are collected, 20L is concentrated into, obtains
Concentrate II.By AB-8 macroporous absorbent resins on filtrate II, (contained for 2,40% ethanol elution with the pH value of 3BV upper prop liquid
0.01mol/L hydrochloric acid), 240L ethanol eluates II are collected, 20L is concentrated into and obtains concentrate III；Concentrate II is directly cooled to 1~
4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then after recrystallization coffee tannin sterling 7.56kg；6000rpm is carried out to concentrate III
10~20min is centrifuged, supernatant is obtained, supernatant, to being extracted, is collected upper strata and contained with two to three times volume ethyl acetate
The extract of ethyl acetate, is concentrated under reduced pressure at 40~50 DEG C, reclaims ethyl acetate, and obtain chlorogenic acid pure product 5.78kg.Through
The purity of HPLC detection chlorogenic acid samples is 98.93%；The purity of tannin sample is 99.02%.
Embodiment 2
Weigh 200kg coffee beans, progress is crushed to the mesh of 10 mesh~20, add 1500L ether and carry out cold soaking and carry 3~4
Hour；Ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, will contain diethyl ether solution and depressurized at 40~50 DEG C
Concentration, reclaims ether, and obtain coffee bean fat 30kg；1200L water is added to coffee bean residue, room temperature is extracted, and the time is 5h,
Ceramic membrane filter once obtains filtrate I, uses ultrafilter (molecular cut off is 500) to carry out being concentrated to give 50L concentrates I and 150L filters
Liquid II, by AB-8 macroporous absorbent resins on concentrate I, adsorbs after 30min, with the purifying water elution of 1BV upper prop liquid, abandons elution
Liquid, then eluted with the pH value of 3BV upper prop liquid for 6,30% ethanol water, 500L ethanol eluates I are collected, 20L is concentrated into, obtains
Concentrate II.
By AB-8 macroporous absorbent resins on filtrate II, (contained for 2,40% ethanol elution with the pH value of 3BV upper prop liquid
0.01mol/L hydrochloric acid), the 500L of ethanol eluate II is collected, the 1/20 of original volume is concentrated into, obtains concentrate III；Concentrate II is straight
Connect and be cooled to 1~4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then after recrystallization coffee tannin sterling 15.48kg；To concentrate
III, which carries out 6000rpm, centrifuges 10~20min, obtains supernatant, supernatant with two to three times volume ethyl acetate to extracting,
The extract that ethyl acetate is contained on upper strata is collected, is concentrated under reduced pressure at 40~50 DEG C, ethyl acetate is reclaimed, and it is pure to obtain chlorogenic acid
Product 11.88kg.Detect that the purity of chlorogenic acid sample is 99.03% through HPLC；The purity of tannin sample is 99.16%.
Embodiment 3
Weigh 400kg coffee beans, progress is crushed to the mesh of 10 mesh~20, add 3000L ether and carry out cold soaking and carry 3~4
Hour；Ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, will contain diethyl ether solution and depressurized at 40~50 DEG C
Concentration, reclaims ether, and obtain coffee bean fat 60kg；Add 2000L water into coffee bean residue, room temperature extraction, the time is
4h, ceramic membrane filter once obtains filtrate I, uses ultrafilter (molecular cut off is 500) to carry out being concentrated to give the He of 75L concentrates I
225L filtrates II, by AB-8 macroporous absorbent resins on concentrate I, adsorb after 30min, with the purifying water elution of 1BV upper prop liquid, abandon
Eluent, then eluted with the pH value of 3BV upper prop liquid for 6,30% ethanol water, 800L ethanol eluates I are collected, are concentrated into
32L, obtains concentrate II.
By AB-8 macroporous absorbent resins on filtrate II, (contained for 2,40% ethanol elution with the pH value of 3BV upper prop liquid
0.01mol/L hydrochloric acid), the 800L of ethanol eluate II is collected, the 1/20 of original volume is concentrated into, obtains 40L concentrates III；Concentrate II
Directly be cooled to 1~4 DEG C of crystallization 8h, filter to obtain coarse crystallization, then after recrystallization coffee tannin sterling 32.66kg；To concentration
Liquid III carries out 6000rpm and centrifuges 10~20min, obtains supernatant, supernatant is with two to three times volume ethyl acetate to extracting
Take, collect the extract that ethyl acetate is contained on upper strata, be concentrated under reduced pressure at 40~50 DEG C, reclaim ethyl acetate, and obtain green original
Sour sterling 24.45kg.Detect that the purity of chlorogenic acid sample is 99.15% through HPLC；The purity of tannin sample is 99.35%.
Claims (3)
1. a kind of method from coffee bean chlorogenic acid extracting and tannin, specific steps include as follows：
(1) dried coffee bean is crushed to the mesh of 10 mesh~20, is added ether and is carried out cold soaking and carries 3~4 hours, wherein coffee
The weight kg of coffee beans and the volume L ratios of ether are 1:7~15；
(2) ceramic membrane filter once obtains coffee bean residue and containing diethyl ether solution, will contain diethyl ether solution and subtract at 40~50 DEG C
Pressure concentration, reclaims ether, and obtain coffee bean fat；
(3) water is added to coffee bean residue, room temperature extraction, the time is 3~5h, wherein coffee bean residue weight kg and the body of water
Product L ratios are 1:5~10；
(4) ceramic membrane filter once obtains filtrate I, uses ultrafilter (molecular cut off is 500) to carry out being concentrated to give concentrate I and filter
Liquid II；
(5) by AB-8 macroporous absorbent resins on concentrate I, after absorption 30min, with the purifying water elution of 1BV upper prop liquid, elution is abandoned
Liquid, then eluted with the pH value of 3BV upper prop liquid for 6,30% ethanol water, ethanol eluate I is collected, the 1/ of original volume is concentrated into
10~1/25, obtain concentrate II；
(6) by AB-8 macroporous absorbent resins on filtrate II, (contained for 2,40% ethanol elution with the pH value of 3BV upper prop liquid
0.01mol/L hydrochloric acid), ethanol eluate II is collected, the 1/10~1/20 of original volume is concentrated into, obtains concentrate III；
(7) concentrate II is directly cooled to 1~4 DEG C of crystallization 8h, filters to obtain coarse crystallization, then after recrystallization coffee tannin is pure
Product；
(8) 6000rpm is carried out to concentrate III and centrifuges 10~20min, obtain supernatant, supernatant with two to three times volume acetic acid
Ethyl ester is collected the extract that ethyl acetate is contained on upper strata, is concentrated under reduced pressure at 40~50 DEG C, reclaim acetic acid second to extracting
Ester, and obtain chlorogenic acid pure product.
2. method according to claim 1, wherein filter process are all to use ceramic membrane filter, fenestra pore size is 0.22 μ
m。
3. method according to claim 1, wherein concentration process are all using being concentrated under reduced pressure, temperature control 40~55 DEG C it
Between.
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| CN107879937A (en) * | 2017-10-24 | 2018-04-06 | 四川九章生物科技有限公司 | A kind of new crystal of chlorogenic acid and preparation method thereof |
| CN109096110A (en) * | 2018-09-05 | 2018-12-28 | 安徽龙津生物科技有限公司 | A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean |
| CN113279253A (en) * | 2021-04-02 | 2021-08-20 | 百事基材料（青岛）股份有限公司 | Silk large biological fiber containing coffee active component and preparation method thereof |
| CN113527383A (en) * | 2021-06-28 | 2021-10-22 | 中南林业科技大学 | High-purity plant tannin prepared from industrial tannin extract and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879937A (en) * | 2017-10-24 | 2018-04-06 | 四川九章生物科技有限公司 | A kind of new crystal of chlorogenic acid and preparation method thereof |
| CN109096110A (en) * | 2018-09-05 | 2018-12-28 | 安徽龙津生物科技有限公司 | A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean |
| CN113279253A (en) * | 2021-04-02 | 2021-08-20 | 百事基材料（青岛）股份有限公司 | Silk large biological fiber containing coffee active component and preparation method thereof |
| CN113527383A (en) * | 2021-06-28 | 2021-10-22 | 中南林业科技大学 | High-purity plant tannin prepared from industrial tannin extract and preparation method thereof |
| CN113527383B (en) * | 2021-06-28 | 2023-02-17 | 中南林业科技大学 | High-purity plant tannin prepared from industrial tannin extract and preparation method thereof |
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