CN109096110A - A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean - Google Patents
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean Download PDFInfo
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- CN109096110A CN109096110A CN201811033500.XA CN201811033500A CN109096110A CN 109096110 A CN109096110 A CN 109096110A CN 201811033500 A CN201811033500 A CN 201811033500A CN 109096110 A CN109096110 A CN 109096110A
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The technique that the invention discloses a kind of to isolate and purify 99% chlorogenic acid from coffee bean, comprising the following steps: S1 pulverizes and sieves coffee bean, obtains coffee bean coarse powder A；S2 extracts coffee bean coarse powder A three times with ethyl alcohol, and extracting solution is concentrated to give concentrate B；S3, concentrate B add water, and stirring, centrifugation take the upper macroporous absorbent resin of filtrate, desorbed after washing with ethyl alcohol, obtain stripping liquid C；S4 obtains nanofiltration refined solution D by stripping liquid C by nanofiltration membrane treatment；S5, by nanofiltration refined solution D decoloration, filtering, filtrate decompression concentration, crystallization obtain crystal crude product E；S6 will be recrystallized with Diluted Alcohol after crystal crude product E centrifugation, must recrystallize wet product F；S7 by recrystallization wet product F drying, crushes, screening, obtains chlorogenic acid finished product G.The separating technology that the present invention is coupled using absorption-nanofiltration membrane-recrystallization, it is easy to operate, environmentally protective, while the purity is high (> 99%) of finished product chlorogenic acid, meet the high-purity requirement in the fields such as new drug development, chemical reagent.
Description
Technical field
The present invention relates to technical field of plant extraction more particularly to a kind of 99% chlorogenic acids of isolating and purifying from coffee bean
Technique.
Background technique
Coffee bean derives from the seed of madder wort Coffea arabica, middle fruit coffee and big fruit coffee.It is extracted in coffee bean
In object contain more chlorogenic acid, therefore frequently by the source as a kind of effective chlorogenic acid carry out using.
Chlorogenic acid different name caffeotannic acid, chemical name: 3-caffeoylquinic acid, English name Chlorogenic acid, CAS
Number: 327-97-9, molecular formula: C16H18O9, molecular weight: 354.3087, density: 1.65g cm3, fusing point: 205-209 DEG C, molecule
Structure:
Chlorogenic acid is known as " plant gold ", is the object that production is chased by numerous producers.Chlorogenic acid is a kind of important life
Active substances, have antibacterial, it is antiviral, increase white blood cell, Hepatoprotective cholagogue, antitumor, lowering blood pressure and blood fat, remove freely
The effects of base and stimulating central nervous system system, modern science has been deep into food, health care, doctor to the research of chlorogenic acid bioactivity
The multiple fields such as medicine and daily-use chemical industry.The main source of chlorogenic acid is extracted from natural plants, the country be always with honeysuckle,
The plant materials such as Cortex Eucommiae, foreign countries are mainly with coffee bean etc. for raw material.
Mainly have to the extracting method of chlorogenic acid at present: water extraction and alcohol precipitation method, stone mercaptans, lead salt precipitation, supercritical ultrasonics technology,
Enzyme process, extraction separation method, Thin-layer chromatography, Ultra filtration membrane method；The method of the above common chlorogenic acid extracting, itself is all
There is some defects, such as: energy consumption is high, extraction time is long, recovery rate is low, product purity is low.Thus existing general green original
Acid, which extracts, all to be combined using the above several method, is learnt from other's strong points to offset one's weaknesses, to improve the recovery rate and purity of chlorogenic acid, but current high-purity
Chlorogenic acid be typically all to use honeysuckle or Swertia patens as raw material extraction, the chlorogenic acid content of product is up to 99%, and
The chlorogenic acid content extracted from folium cortex eucommiae, Radix Salviae Miltiorrhizae, pueraria lobata and coffee bean is up to 98%, still contains a small amount of impurity, shadow
Its application in injection, anti-inflammatory injection and antibacterial specific drug is rung.
High-quality coffee bean is mainly used for processing coffee at present, wherein not obtaining very there are also most such as dead beans
Coffee can be mentioned significantly the directly use of dead beans by good utilisation with stock sentimental taste if substandard products coffee bean is made full use of
The planting income of high coffee；And coffee bean Content of Chlorogenic Acid is high, the coffee bean chlorogenic acid content of Yunnan Province is up to 14%, and
Price is low.Use coffee bean as the substitution of the medicinal materials such as honeysuckle, folium cortex eucommiae, both substantially increases the utilization of the residues such as coffee bean
Efficiency, improves the added value of coffee bean, and get rid of the dependence of the medicinal materials such as honeysuckle, folium cortex eucommiae, and complete incidence graph market is to gold
The wilderness demand of the medicinal materials such as honeysuckle flower, folium cortex eucommiae extends the medicinal source resource that chlorogenic acid extracts raw material.
To sum up, how from high-purity chlorogenic acid product is extracted in coffee bean, (chlorogenic acid more than especially 99% purity is produced
Product), become China's chlorogenic acid industry essential step in line with international standards, and establish the important technology branch of China's coffee industry
It holds.
Summary of the invention
The purpose of the present invention is to solve disadvantages existing in the prior art, and the one kind proposed is separated from coffee bean
The technique for purifying 99% chlorogenic acid.
To achieve the goals above, present invention employs following technical solutions:
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean, comprising the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2, extract, concentration: taking parts by weight is 1 part of coffee bean coarse powder A, is mentioned with 5-10 parts of 10~95% alcohol refluxs
It takes three times, combined extract, and is concentrated into 2-4 times of coffee bean coarse powder A weight, obtain concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 40~80% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: S4 by stripping liquid C by nanofiltration membrane treatment, obtains nanofiltration refined solution D；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 2-4 hours, cold filtration,
Filtrate decompression is concentrated into small size, crystallizes 12~24 hours, obtains crystal crude product E；
S6, centrifugation, recrystallization: crystal crude product E is centrifuged, and obtained precipitating is recrystallized 2-3 times with Diluted Alcohol, after filtering
Recrystallize wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 70~80 DEG C, is used after dry
Pulverizer crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G.
Preferably, in S3, the model of macroporous absorbent resin is specially AB-8, X-5, NK-2, NKA-2, NK-9, D3520,
Any one of D101 and WLD.
Preferably, in S4, nanofiltration membrane is specially DL series material seperation film, and flux is 500 molecular weight, and nanofiltration membrane is clipped in
The centre of two layers of microfiltration membranes；Microfiltration membranes are specially any one of high score subclass microfiltration membranes or inorganic ceramic micro-filtration membrane, microfiltration membranes
Pore diameter range be 0.2-2um.
Preferably, in S6, the concentration of Diluted Alcohol is 5%-25%.
Preferably, in S6, filtering uses Buchner funnel.
Compared with prior art, the beneficial effects of the present invention are:
1. the present invention has gathered the excellent of several separation methods using absorption-nanofiltration membrane-recrystallization coupling separating technology
Gesture, and the shortcoming for the method for being separately separated is avoided simultaneously；Particle i.e. in absorption, the process rinsed removal material liquid is miscellaneous
Matter and ion avoid the pollution problem of subsequent nano-filtration film, in use, nanofiltration membrane to be clipped in the centre of two layers of microfiltration membranes, antipollution
Excellent performance improves the service life and operation stability of nanofiltration membrane；Nanofiltration membrane further obstructs the macromolecular unfavorable to crystallization
The organic matters such as albumen, cellulose guarantee the high-purity of chlorogenic acid to improve the purity of crystalline rate and crystallized product.
2. in technique proposed by the present invention, extraction-desorption-recrystallization is all made of ethanol water as solvent, avoid making
With unsafe organic reagent, chlorogenic acid finished product purity is up to 99%, more taller than low-producing layer post separation, finished product safety
It reliably, can direct industrial applications without post-processing.
3. the present invention has the advantages that easy to operate, environmentally protective and is conducive to industrialized production, while finished product chlorogenic acid
(> 99%) with high purity can satisfy new drug development, chemical reagent and in the requirement of the high-purity of biochemical analysis and chemical industry.
Detailed description of the invention
Fig. 1 is a kind of flow chart for the technique that 99% chlorogenic acid is isolated and purified from coffee bean proposed by the present invention；
Fig. 2 is the HPLC map and chlorogenic acid purity analysis of finished product G in the embodiment of the present invention 4.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.
Embodiment 1:
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean, comprising the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: being taken coffee bean coarse powder 100g, is successively returned via 20% ethyl alcohol of 800ml, 700ml and 600ml
Stream extracts 3 times, and reflux extracting time is respectively 2 hours, 1.5 hours and 1 hour, merges No. 3 extracting solutions, 0.01~
0.06MPa reduced under vacuum, is concentrated into 280ml, obtains concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 45% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: stripping liquid C is passed through the nanofiltration membrane treatment of 500 molecular weight, obtains nanofiltration refined solution D by S4；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 2.5 hours, cold filtration,
Filtrate decompression is concentrated into small size, crystallizes 14 hours, obtains crystal crude product E；
Centrifugation, recrystallization: S6 crystal crude product E is centrifuged, obtained precipitating will be recrystallized with 10% ethyl alcohol recrystallization 2 times
Good material filtered on buchner funnel, must recrystallize wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 75 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G, analyzes through HPLC (high performance liquid chromatography) tracing detection, at
Chlorogenic acid content in product G is 99.23%.
Embodiment 2:
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean, comprising the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: being taken coffee bean coarse powder 100g, is successively returned via 40% ethyl alcohol of 800ml, 700ml and 600ml
Stream extracts 3 times, and reflux extracting time is respectively 2 hours, 1.5 hours and 1 hour, merges No. 3 extracting solutions, 0.01~
0.06MPa reduced under vacuum, is concentrated into 350ml, obtains concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 55% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: stripping liquid C is passed through the nanofiltration membrane treatment of 500 molecular weight, obtains nanofiltration refined solution D by S4；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 3 hours, cold filtration, filter
Liquid is concentrated under reduced pressure into small size, crystallizes 16 hours, obtains crystal crude product E；
Centrifugation, recrystallization: S6 crystal crude product E is centrifuged, obtained precipitating will be recrystallized with 15% ethyl alcohol recrystallization 2 times
Good material filtered on buchner funnel, must recrystallize wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 75 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G, analyzes through HPLC (high performance liquid chromatography) tracing detection, at
Chlorogenic acid content in product G is 99.16%.
Embodiment 3:
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean, comprising the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: being taken coffee bean coarse powder 100g, is successively returned via 55% ethyl alcohol of 800ml, 700ml and 600ml
Stream extracts 3 times, and reflux extracting time is respectively 2 hours, 1.5 hours and 1 hour, merges No. 3 extracting solutions, 0.01~
0.06MPa reduced under vacuum, is concentrated into 300ml, obtains concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 65% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: stripping liquid C is passed through the nanofiltration membrane treatment of 500 molecular weight, obtains nanofiltration refined solution D by S4；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 3.5 hours, cold filtration,
Filtrate decompression is concentrated into small size, crystallizes 18 hours, obtains crystal crude product E；
Centrifugation, recrystallization: S6 crystal crude product E is centrifuged, obtained precipitating will be recrystallized with 20% ethyl alcohol recrystallization 2 times
Good material filtered on buchner funnel, must recrystallize wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 75 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G, analyzes through HPLC (high performance liquid chromatography) tracing detection, at
Chlorogenic acid content in product G is 99.35%.
Embodiment 4:
A kind of technique isolating and purifying 99% chlorogenic acid from coffee bean, comprising the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: being taken coffee bean coarse powder 100g, is successively returned via 75% ethyl alcohol of 800ml, 700ml and 600ml
Stream extracts 3 times, and reflux extracting time is respectively 2 hours, 1.5 hours and 1 hour, merges No. 3 extracting solutions, 0.01~
0.06MPa reduced under vacuum, is concentrated into 400ml, obtains concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 75% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: stripping liquid C is passed through the nanofiltration membrane treatment of 500 molecular weight, obtains nanofiltration refined solution D by S4；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 4.5 hours, cold filtration,
Filtrate decompression is concentrated into small size, crystallizes 22 hours, obtains crystal crude product E；
Centrifugation, recrystallization: S6 crystal crude product E is centrifuged, obtained precipitating will be recrystallized with 20% ethyl alcohol recrystallization 3 times
Good material filtered on buchner funnel, must recrystallize wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 75 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G, analyzes through HPLC (high performance liquid chromatography) tracing detection, at
Chlorogenic acid content in product G is 99.61%.
Comparative example:
It is comparison with 104876824 A of patent CN " a kind of technique for isolating and purifying chlorogenic acid from coffee bean " comprising
Following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: being taken coffee bean coarse powder 100g, is successively returned via 75% ethyl alcohol of 800ml, 700ml and 600ml
Stream extracts 3 times, and reflux extracting time is respectively 2 hours, 1.5 hours and 1 hour, merges No. 3 extracting solutions, 0.01~
0.06MPa reduced under vacuum, is concentrated into 400ml, obtains concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, first uses
Macroporous absorbent resin is washed, water-solubility impurity is removed, then desorbed with 75% ethyl alcohol, obtains stripping liquid C；
S4, decoloration, crystallization: active carbon being added into stripping liquid C, and return stirring decolourizes 4.5 hours, cold filtration, filtrate
It is concentrated under reduced pressure into small size, crystallizes 22 hours, obtains crystal crude product E；
Centrifugation, recrystallization: S5 crystal crude product E is centrifuged, obtained precipitating will be recrystallized with 20% ethyl alcohol recrystallization 3 times
Good material filtered on buchner funnel, must recrystallize wet product F；
S6, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 75 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G, analyzes through HPLC (high performance liquid chromatography) tracing detection, at
Chlorogenic acid content in product G is 98.24%.
1 process conditions of table and product quality
As shown in table 1, optimum producting condition of the invention are as follows: the concentration 75% for extracting ethyl alcohol desorbs the concentration of ethyl alcohol
75%, concentration of alcohol 20% is recrystallized, is recrystallized 3 times, the purity of finished product G Content of Chlorogenic Acid is up to 99.61%；By embodiment 4
Compared with comparative example, the present invention, which is used, similarly purifies condition with comparative example, only before chlorogenic acid crystallization, using nanofiltration
Film is filtered stripping liquid C, filters off albumen, cellulose of macromolecular etc., avoids two sides during condensing crystallizing
The negative effect in face: first is that these big molecular impurities influence crystal yields, second is that big molecular impurity can also be settled with crystallized product
And then the purity of finished product G Content of Chlorogenic Acid is influenced, to guarantee the high yield and high-purity of chlorogenic acid finished product G, make of the invention green
Ortho acid product can satisfy new drug development, chemical reagent and in the requirement of the high-purity of biochemical analysis and chemical industry.
Absorption-nanofiltration membrane-recrystallization integrated separation technique multiplication effect: the present invention uses absorption-nanofiltration membrane-recrystallization
The separating technology of coupling makes purity > 99% of chlorogenic acid finished product G, and tracing it to its cause is because the present invention has gathered several separation sides
The advantage of method, and the shortcoming for the method for being separately separated is avoided simultaneously.Separation process analysis: it is gone in absorption, the process rinsed
Except the granule foreign and ion in material liquid, avoid subsequent nano-filtration film pollution problem (because fouling membrane mostly due to nocuousness from
Son and dust impurity, which will lead to, makes membrane lifetime decline to a great extent), to improve the service life and operation stability of nanofiltration membrane；Nanofiltration
Film is further obstructed to the organic matters such as unfavorable albumen, the cellulose of macromolecular are crystallized, to improve crystalline rate and crystallization production
The purity of object guarantees the high-purity of chlorogenic acid.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (5)
1. a kind of technique for isolating and purifying 99% chlorogenic acid from coffee bean, which comprises the following steps:
S1 is crushed: coffee bean be crushed 10 meshes first, obtain coffee bean coarse powder A；
S2 is extracted, concentration: taking parts by weight is 1 part of coffee bean coarse powder A, extracts three with 5-10 parts of 10~95% alcohol refluxs
It is secondary, combined extract, and it is concentrated into 2-4 times of coffee bean coarse powder A weight, obtain concentrate B；
S3, adsorbing separation: being added water into concentrate B, stir evenly, centrifugation, takes the upper macroporous absorbent resin of filtrate, is first washed with water
Macroporous absorbent resin removes water-solubility impurity, then is desorbed with 40~80% ethyl alcohol, obtains stripping liquid C；
Nanofiltration membrane treatment: S4 by stripping liquid C by nanofiltration membrane treatment, obtains nanofiltration refined solution D；
S5, decoloration, crystallization: active carbon being added into nanofiltration refined solution D, and return stirring decolourizes 2-4 hours, cold filtration, filtrate
It is concentrated under reduced pressure into small size, crystallizes 12~24 hours, obtains crystal crude product E；
S6, centrifugation, recrystallization: crystal crude product E is centrifuged, and obtained precipitating is recrystallized 2-3 times with Diluted Alcohol, is obtained after filtering and is tied again
Brilliant wet product F；
S7, dry, powder processed: being put into oven drying for recrystallization wet product F, and drying temperature is 70~80 DEG C, uses and crushes after dry
Machine crushes, and through 80 meshes point, obtains powdered chlorogenic acid finished product G.
2. a kind of technique for isolating and purifying 99% chlorogenic acid from coffee bean according to claim 1, which is characterized in that institute
It states in S3, the model of macroporous absorbent resin is specially appointing in AB-8, X-5, NK-2, NKA-2, NK-9, D3520, D101 and WLD
It is a kind of.
3. a kind of technique for isolating and purifying 99% chlorogenic acid from coffee bean according to claim 1, which is characterized in that institute
It states in S4, nanofiltration membrane is specially DL series material seperation film, and flux is 500 molecular weight, and the nanofiltration membrane is clipped in two layers of micro-filtration
The centre of film；The microfiltration membranes are specially any one of high score subclass microfiltration membranes or inorganic ceramic micro-filtration membrane, the microfiltration membranes
Pore diameter range be 0.2-2um.
4. a kind of technique for isolating and purifying 99% chlorogenic acid from coffee bean according to claim 1, which is characterized in that institute
It states in S6, the concentration of Diluted Alcohol is 5%-25%.
5. a kind of technique for isolating and purifying 99% chlorogenic acid from coffee bean according to claim 1, which is characterized in that institute
It states in S6, filtering uses Buchner funnel.
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Application publication date: 20181228 |