CN1276926C - Tannic acid purifying process - Google Patents
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- CN1276926C CN1276926C CN 02130628 CN02130628A CN1276926C CN 1276926 C CN1276926 C CN 1276926C CN 02130628 CN02130628 CN 02130628 CN 02130628 A CN02130628 A CN 02130628A CN 1276926 C CN1276926 C CN 1276926C
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Abstract
The present invention relates to a purification method for gallnut tannic acid. The purity of the industrial gallnut tannic acid produced by a conventional method is only between 70 and 80%. The purification method for the gallnut tannic acid adopts a physical method for separating, refining and purifying tannic acid. In the method, the means such as cooling settling, separating by an ion exchange method, solution decolorizing, solution purifying, solution extraction refining, purifying by a chromatogram method, etc. are adopted. The present invention adopts brewing tannic acid products with the molecular weight in a range between 1400 and 1700, the purity reaches higher than 99%, the color is ecru, and the present invention meets the requirement of brewing industry.
Description
Technical field:
The application relates to a kind of method of purification of the Weibull that uses in beer industry.
Background technology:
In recent years, Chinese gallotanninic acid obtains more and more widely application at China's beer industry, and the use of domestic nearly various schools of thinkers brew-house proves: the different steps in beer production is added Weibull, can improve the non-biostability of beer, extends the shelf life; Can also improve simultaneously the ageing resistance of finished beer, improve the local flavor of beer.As far back as 1997, that China relevant department has introduced is Belgian " preserve make red " product, at first be used for the clarification of barley juice of beer and the processing of fermented liquid, after 1998, " the logical edible Weibull in Shen " and the medicinal Weibull of Chinese forest-science academy of Changchun development are also used in brewing industry successively.On this basis, we are according to the particular requirement of brewage, work out to be suitable for adsorbing the proteic a new generation of beer and to brewage that to use Weibull, principal feature be molecular chain.Through strict screening, can optionally catch the labile protein matter in the beer, the purity height, of light color.
Brewageing with Weibull is with the distinctive forest resourceies of China---Turkey-galls is a raw material, adopts the physical method lixiviate, makes with extra care, purifies and strict molecular screening, produces the efficient stable agent to human body safety.Because to compare result of use obvious with other stablizer, the effect height, consumption is few, can significantly reduce processing cost, thus product extremely the user welcome, have good market outlook.
Summary of the invention:
The present invention is in order to overcome above-mentioned shortcoming, and the method for purification of the Weibull that a kind of cost is low, speed is fast, purity is high beer uses is provided.
The industrial Chinese gallotanninic acid of producing with flooding is brown or the light brown powder shape, and it is a kind of mixture, contains materials such as a small amount of carbohydrate, polyphenol, inorganic salt, plant pigments, protein, lipid.The Weibull molecule has stronger polarity, easily is dissolved in water and some organic solvents, as alcohol, acetate, ethyl acetate, methyl alcohol, acetone etc., and is not dissolved in organic solvents such as benzene, chloroform, sherwood oil, dithiocarbonic anhydride.The tannin aqueous acid shows the hemicolloid state, presents different disperse phase under different concentration and temperature condition, Weibull can be carried out initial gross separation according to these characteristics.
Impurity beyond the Weibull of enumerating previously belongs to the material that be eliminated in fermented wine is produced, content is few more good more, and the Weibull purity requirement of using for clarify beer reaches 96%.The separation of so-called Weibull is meant with the method beyond the chromatogram Weibull is carried out preliminary separation, refining, purifying.Just Weibull and non-tannis acid are separated, perhaps the Weibull branch is made different components, obtain the Weibull mixture of roughing out.The separation method of having studied maturation at present or being applied has hide powder method, the precipitator method, dialysis or ultrafiltration process, crystallization process, solvent lixiviate or solvent precipitation.Some method is generally adopted in industrial production, the method that has is isolated Weibull from raw material purity reaches more than 95%, both made after chromatography is applied, some method still has using value very much, still needs the broken color spectrometry to carry out the processing of last stage.
Nineteen eighty-two Nishizawa isolates 8 kinds of compounds with Chinese Turkey-galls; contain a plurality of galloyl in each molecule; obtain B-D-glucose and gallic acid after the hydrolysis; galloyl is oxidative deformation in air; so avoid contacting when producing Weibull, adopt the operation of closed equipment low temperature short period of time as far as possible with air.Separate, the purification Weibull generally carries out in solution, through a series of separation, refining, purifying finally obtains pure solution, concentrates, drying again, produces pure Weibull product.
The method of purification of Weibull of the present invention comprises the following steps:
The first step: cooling precipitation: water is joined in the industrial tannic acid that purity is 70-80%, make degree Beaume reach 6-8 ° of Be ' after the dissolving, put into heavy clear jar, send into refrigerating chamber, supernatant liquid is taken in the cooling clarification;
Second step: ion exchange method is separated: successively above-mentioned clear liquid is carried out ion-exchange by anionite-exchange resin, Zeo-karb, obtain the solution after the ion-exchange;
The 3rd one: solution decolouring with purify: with the solution after the ion-exchange by gac and filtered through silica gel;
The 4th step: the extracting and refining of solution: the solution extraction operating process is divided three phases: a, with mixing solutions after the above-mentioned filtration and ethyl acetate solvent thorough mixing, the mixed solution of Weibull after filtering dissolved in this solvent, ethyl acetate severe is little, rise gradually, remaining filtration back mixing solutions is than great, descend gradually, be divided into the weight liquid layer; B, its weight liquid layer is separated in separator; C, reclaim ethyl acetate in a vacuum, the Weibull ethyl ester liquid behind the evaporation of acetic acid ethyl ester is sent to next procedure and carries out purifying;
The 5th step: chromatography purification: steam the solution dissolve with ethanol after the ethyl acetate, inject glucose gel LH-20 post, carry out wash-out repeatedly with 1: 1 ethanol-water solution, then, enter the reduction vaporization system to reclaim ethanolic soln, remaining solute partly is pure Weibull and imports the oven dry of aluminum drip pan, 150 ℃ of drying temperatures, 2 hours time, adopt omnipotent masher with the exsiccant solid block Weibull shape (60-80 order) of claying into power, be the Weibull product of being developed.
Wherein in the first step, the cooling clarifying temp is-3 to 0 ℃.In second step, anionite-exchange resin is No. 704 weakly base resins, and Zeo-karb is No. 732 highly acidic resins.
The principle of this purification process is specific as follows:
1. the cooling of the Weibull aqueous solution precipitates
The Weibull of producing with flooding contains multiple composition and impurity, must clarify through overcooling before refining, otherwise the inaccessible specification of quality of refining effect not only simultaneously also can increase processing cost.
When the Weibull aqueous solution is met when cold, cloth youth movement slows down than macroparticle, and then generation precipitation, tannic acid solution generation layering, the upper strata is the Weibull colloidal dispersion, lower floor is Weibull colloid part and thick dispersed system, wherein contain resin, vegetable-protein and starch etc., adopt decantation or centrifuging with precipitation separately to produce to brewage and to take cooled supernatant liquid with Weibull, the clarification operation is preferably in the refrigerating chamber to be carried out, the Turkey-galls vat liquor is put into heavy clear jar, send into refrigerating chamber, the constant temperature cooling, after some time, can reach the layering purpose.Trial-production also can adopt the cooling tank mode to cool off for be pilot.
At first the Turkey-galls vat liquor is put into special cooling tank, be cooled to design temperature under constantly stirring, clarify with being pumped in the settling tank, supernatant liquid is used to produce brewage uses Weibull, and lower sediment thing hydrolyzable is made gallic acid.
Cooling tank and settling tank should have been adopted stainless material or glass-ceramic manufacturing, avoid with ironware contacting in the experimentation, in order to avoid produce chemical transformation, the tank skin lagging material is selected good heat insulating, light specific gravity, moisture-proof, material that fire performance is good.
Because Weibull colloidal solution settling velocity is slow, clarifying process selects for use the intermittent type less expensive a little.
2. ion exchange method is separated
After the tannic acid solution cooling clarification, in its clear liquor, also have gallic acid, many condensed gallic acids, inorganic salts and pigment etc., therefore brewage when use Weibull in production, must through making with extra care, purification processes.
The method of purification of Weibull is a lot, through screening, considers from refining effect and security standpoint, tentatively selects three kinds of production process routes; 1. ethanolic soln leaching method; 2. ethyl acetate extraction; 3. ion exchange method.More than three kinds of methods, can both reach specified requirement from quality product, consider from energy expenditure and organic solvent requirement again, the back a kind of method production cost low.
Ion-exchange is similar with adsorption process, be to reject away by the macromolecular compound that ion exchange resin will have an active ion, positively charged ion and gallic acids such as the calcium that is about to contain in the Weibull, magnesium, iron, many condensed gallic acids, negatively charged ion such as organic pigment are removed away by ion-exchange.
Ion exchange resin is a kind of particulate, the solid of holey by a stable macromole charged group and other some can the composition by the metathetical ion, is not dissolved in water, also be not dissolved in electrolyte solution, can from solution, draw ion and carry out from exchange.
This testing apparatus is a vertical Glass tubing that has inlet and outlet device, and promptly ion exchange process carries out in the Glass tubing exchange column.Solution sees through fixed bed from top to bottom, carries out ion-exchange (absorption), after ion exchange resin uses a stage, and can also leaching regeneration.Except adsorbed ionic ion exchange resin can recycle, also can replenish a part of resin at any time according to the exchange effect.
Fixed-bed ion exchange device, resin in the exchange column remains static, processed solution flows along fixed-direction in exchange column, this system device is simple, and technical maturity is convenient to operation, convenient management, be the purification style that generally adopts on water purification and the chemical industry, shortcoming is that the exchange capacity of resin utilization ratio is low, and the regeneration expense is bigger.
3. solution decolouring and purification
Turkey-galls with the hot water lixiviate, though adopt the cooling clarification, the ion-exchange purification separation has been removed most resins, starch, inorganic salts and pigment, but can not reach requirement of high purity, use Weibull purity in order further to improve to brewage, gac and silica gel continuous filtration are adopted in experiment.Gac has tangible decolorization to liquid, remove the contaminant particles on the local flavor, silica gel is the tasteless vesicular particulate matter of a kind of white, can optionally absorb colloid and protein particulate material, improve the purity of brewageing with tannic acid solution, filtration unit is one and has the glass cylinder of importing and exporting up and down that the cylinder bottom is provided with the sieve end.
4. the extracting and refining of solution
Extraction is to utilize solvent that the difference of substance dissolves ability is separated, and normally carries out in liquid phase, and the solvent that can be used as Weibull is a lot, and ethyl acetate is one of extraction solvent preferably.The ethyl acetate boiling point is slightly soluble in water for 77.1 ℃, is colourless flammable liquid, and its steam and air mixed form the fried limit 2.2～11.2% (volume) of the fried property mixture combustion of combustion.Its advantage is good to the solvability of Weibull, and as resin, starch, inorganic salt do not have solvency action, can reach isolating purpose like this to non-tannis acid.Solubleness is very little between ethyl acetate and the water, and difference in specific gravity is big, and layering forms two kinds of liquid phases rapidly, is convenient to reclaim.
The solution extraction operating process is divided three phases: a, the Weibull mixed solution that is extracted and solvent thorough mixing make Weibull dissolve in the solvent from processed mixed solution; B, extraction finish back weight liquid layer and separate in separator, obtain extraction phase and extracting phase; C, the solvent of extraction phase is reclaimed, recycled.
Extraction plant is the glass cylinder of sealing up and down, fills Raschig ring (porcelain) in the tube, and solvent enters from the bottom, flow out on top, and the mixed solution of Weibull is then gone against the stream with solvent, two kinds of liquid fully contacts between the stopping composition space, Weibull constantly changes in the ethyl acetate in the solution, ethyl acetate severe is little, rises gradually, enters storage tank from cat head, Weibull in the Weibull blended liquid phase reduces gradually, impurity increases gradually and since solution than great drop to tower gradually at the bottom of, enter receptor.
For decomposition and the oxidation of avoiding Weibull, under vacuum, reclaim ethyl acetate usually, the Weibull ethyl ester liquid behind the evaporation of acetic acid ethyl ester is sent into next procedure and is carried out purifying
5 chromatography purifications
Steam the Weibull ethyl ester liquid dissolve with ethanol after the ethyl acetate, inject glucose gel LH-20 post, carry out wash-out with ethanol-water solution (1: 1), LH-20 has stronger adsorptive power and resolution capability to Weibull.Wash-out can be obtained ideal results repeatedly.
Weibull behind the purifying, alcohol-water mixing solutions, enter the reduction vaporization system to reclaim ethanolic soln, remaining solute partly is pure Weibull and imports the oven dry of aluminum drip pan, 150 ℃ of drying temperatures, 2 hours time, be dried to the solid block Weibull and adopt the omnipotent masher shape (60-80 order) of claying into power, be the Weibull product of being developed.
Nineteen eighty-two N:shizawa etc. study it, the Chinese tannin acid mixture is made up of five to 12 galloyl glucose, molecular-weight average 1434, each glucosyl group on average have 8.3 galloyl, its chemical structural formula is
In fact Chinese gallotanninic acid is not single compound, but contains the mixture of the poly-gallate fat of many glucose, just before chromatography is used, they can't be separated.
Protein in the beer can optionally combine with gallotannic acid and form sheet protein-Weibull composite precipitation thing, low molecular gallotannic acid is difficult to form precipitation, high molecular gallotannic acid is caught proteic weak effect, think at present can and protein form rapidly sedimentary gallotannic acid molecular weight between 1400-1700, in order to improve its result of use, gallotannic acid must screen, and is the effect of each step purifying below.
1. the extraction of industrial tannic acid: the purity of industrial tannic acid is 70-80%, and Weibull content is relevant with extracting condition (water quality, temperature, time) purifying method.
2. cooling clarification: Chinese gallotanninic acid when the solution degree Beaume in 6-8 ° of Be ', temperature during near freezing point, the throw out that produces is more, rest time is long more under these conditions, the throw out that produces is many more, supernatant liquid is a Weibull colloidal solution, content can reach 85-90%, sends to further refining.The turbid liquid of lower floor is thick Weibull colloid, contains impurity such as resin, vegetable-protein, starch and metal ion, the turbid liquid of lower floor can be discarded during experiment need not, be used for producing gallic acid during batch process.
3. refining: in flooding Turkey-galls raw material process, the material that is dissolved out with Weibull contains gallic acid, many condensed gallic acids, vegetable-protein, chlorophyll, resin, starch and inorganic salt etc.The process that these non-tannis acid compositions are separated gradually is called refining.Weibull purified method is a lot, as methods such as absorption, ion-exchange, dialysis and filtration, crystallization, solvent lixiviate and solvent depositions.The method that this experiment is adopted is as follows:
(1) ion-exchange: behind Weibull aqueous solution process negatively charged ion, the cation sites, can remove part band polar gallic acid, many condensed gallic acids and calcium, magnesium, iron plasma, thus make Weibull purity bring up to 90-95%.
(2) decolouring and purification: utilize the adsorption of activated carbon and silica gel porous mass, so that the Weibull aqueous solution reaches the purpose of deodorization aufhellung color, silica gel can be removed impurity such as a part of protein, resin.
(3) extraction: utilize the solubleness of different compounds in solvent different excessively, Weibull is separated from impurity, this experiment selects for use ethyl acetate to obtain good separating effect as solvent, makes Weibull purity bring up to 97-98%.
(4) purifying: modern chromatography is one of main method for preparing at present Weibull pure sample and related compound thereof.The chromatographic process qualitative, quantitative analysis that has been applied to Weibull has paper chromatography, fiberboard and silica-gel plate chromatogram, column chromatography, high performance liquid chromatography, drop counter current chromatography, gel permeation chromatography, gas liqud chromatography.Column chromatography is selected in this experiment for use, and column chromatography is the main method for preparing pure Weibull and related compound at present, is suitable for suitability for industrialized production.It is stationary phase that dextrane gel sephadexLH-20 is adopted in this experiment, and it has stronger adsorptive power and resolving power, and ethanol--water is that moving phase is carried out wash-out to Weibull, has obtained separating effect preferably, and finished product Weibull content reaches more than 99% in employing.
Advantage of the present invention is carried out initial gross separation at first adopting the cooling defecation method, and industrial tannic acid purity is improved 10-15%, has reduced the subsequent disposal load.Selected ethyl acetate, alcohol solvent all are industrial solvent commonly used, and be cheap, and the burning-point height is safe in utilization.Present method column chromatography is purified and selected LH-20 for use is stationary phase, has very strong adsorptive power and resolving power, and absorbing tannin acid molecule amount is 1400-1700.Adopt and the ethyl acetate Weibull aqueous solution liquid-phase extraction energy expenditure in the time that solution concentration can being saved.It is light beige that this technology obtains the Weibull color, and purity is up to more than 99%, and total recovery rate is more than 75% of theoretical yield.
Description of drawings:
Fig. 1 is a Weibull purifying technique equipment flowsheet, and institute's employing equipment and pipeline all must not use the charcoal steel work, can adopt materials such as stainless steel, copper, pottery, plastics.
In Fig. 1, the meaning of each digitized representation is as follows:
1, industrial tannic acid dissolving tank 2, refrigerated cylinder 3, pump 4, clarifying tank 5, anion exchanger 6, cation exchanger 7, activated charcoal filter 8, filtered through silica gel device 9, ethyl acetate header tank 10, extraction tower 11, Weibull aqueous solution storage tank 12, Weibull ethyl ester liquid storage tank 13, pump 14, vaporizer (heating chamber) 15, vaporizer (separate chamber) 16, vacuum pump 17, aqueous ethanolic solution header tank 18, LH-20 post 19, pump 20, scraper-type vaporizer 21, vacuum pump 22, compartment dryer
Fig. 2 is a Weibull purifying technique synoptic diagram.Industrial tannic acid is dissolved in water, and through the cooling precipitation, the turbid liquid of lower floor is discarded, stay supernatant liquor, pass through negatively charged ion, cationic exchange then, the use of can regenerating of negatively charged ion, positively charged ion, solution after the exchange is sloughed pigment, through filtered through silica gel through activated carbon decolorizing, elimination colloid albumen then, adds solvent extraction, vacuum-evaporation is to reclaim solvent, solution after the extraction adds solvent purification again through column chromatography, and reduction vaporization reclaims solvent, thereby obtains the high Weibull of purity.
Embodiment 1:
Get Weibull content and be 71% industrial Chinese gallotanninic acid, carry out purifying according to above-mentioned processing step, the test result of each processing step such as following table 1, test result explanation in this form, purification process by the application, Weibull content can reach 98.8%, can satisfy the service requirements in the wine brewing fully.
Embodiment 2:
Get Weibull content and be 75.5% industrial Chinese gallotanninic acid, carry out purifying according to above-mentioned processing step, the test result of each processing step such as following table 1, test result explanation in this form, purification process by the application, Weibull content can reach 99.4%, can satisfy the service requirements in the wine brewing fully.
Table 1
Claims (3)
1, a kind of purification process of Weibull is characterized in that comprising the following steps:
The first step: cooling precipitation: water is joined in the industrial tannic acid that purity is 70-80%, make degree Beaume reach 6-8 ° of Be ' after the dissolving, put into heavy clear jar, send into refrigerating chamber, supernatant liquid is taken in the cooling clarification;
Second step: ion exchange method is separated: successively above-mentioned clear liquid is carried out ion-exchange by anionite-exchange resin, Zeo-karb, obtain the solution after the ion-exchange;
The 3rd one: solution decolouring with purify: with the solution after the ion-exchange by gac and filtered through silica gel;
The 4th step: the extracting and refining of solution: the solution extraction operating process is divided three phases: a, with mixing solutions after the above-mentioned filtration and ethyl acetate solvent thorough mixing, the mixed solution of Weibull after filtering dissolved in this solvent, ethyl acetate severe is little, rise gradually, remaining filtration back mixing solutions is than great, descend gradually, be divided into the weight liquid layer; B, its weight liquid layer is separated in separator; C, reclaim ethyl acetate in a vacuum, the Weibull ethyl ester liquid behind the evaporation of acetic acid ethyl ester is sent to next procedure and carries out purifying;
The 5th step: chromatography purification: steam the solution dissolve with ethanol after the ethyl acetate, inject glucose gel LH-20 post, carry out wash-out repeatedly with 1: 1 ethanol-water solution, then, enter the reduction vaporization system to reclaim ethanolic soln, remaining solute partly is pure Weibull and imports the oven dry of aluminum drip pan, 150 ℃ of drying temperatures, 2 hours time, it is Powdered to adopt omnipotent masher that exsiccant solid block Weibull is worn into the 60-80 purpose, is the Weibull product behind the purifying.
2, according to the purification process of the Weibull of claim 1, wherein in the first step, the cooling clarifying temp is-3 to 0 ℃.
3, according to the purification process of the Weibull of claim 1, wherein in second step, anionite-exchange resin is No. 704 weakly base resins, and Zeo-karb is No. 732 highly acidic resins.
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Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101433557B (en) * | 2007-11-12 | 2012-02-15 | 天津天士力制药股份有限公司 | Effective component of galla chinensis as well as preparation method and use thereof |
| CN101433558B (en) * | 2007-11-12 | 2011-11-30 | 天津天士力制药股份有限公司 | Effective component of galla chinensis as well as preparation method and use thereof |
| CN101433560B (en) * | 2007-11-13 | 2012-07-04 | 天津天士力制药股份有限公司 | Effective component of galla chinensis as well as preparation method and use thereof |
| CN101507737B (en) * | 2008-02-15 | 2012-06-06 | 天津天士力制药股份有限公司 | Active components of gallnut and preparation method and use thereof |
| CN101879436B (en) * | 2010-07-15 | 2011-11-30 | 南京工业大学 | Decolorizing column and method for decolorizing DHA (docosahexaenoic acid) grease at normal temperature by using same |
| CN102020682B (en) * | 2010-11-09 | 2013-06-05 | 南京泽朗农业发展有限公司 | Preparation method of neuchebulagicacid |
| CN103265585A (en) * | 2013-06-14 | 2013-08-28 | 遵义师范学院 | Novel method for purifying tannic acid |
| CN112341504A (en) * | 2015-12-21 | 2021-02-09 | 河北科技师范学院 | Method for optimizing conditions for extracting tannin from grape seeds by organic solvent extraction method |
| CA3018893A1 (en) | 2016-03-28 | 2017-10-05 | Syneurx International (Taiwan) Corp. | Compositions containing tannic acids and uses thereof |
| CN109320565A (en) * | 2018-11-14 | 2019-02-12 | 云南博泽林化工有限公司 | Deimpurity method is gone during a kind of medical tannic acid of extraction |
| CN109316776A (en) * | 2018-11-14 | 2019-02-12 | 云南博泽林化工有限公司 | A kind of impurity removed system extracting medical tannic acid with Chinese gall |
| US11154531B2 (en) | 2020-02-08 | 2021-10-26 | Syneurx International (Taiwan) Corp. | Compounds and pharmaceutical uses thereof |
| KR20230004765A (en) | 2020-04-23 | 2023-01-06 | 신유알엑스 인터내셔널 (타이완) 코포레이션 | COMPOUNDS AND PHARMACEUTICAL USES THEREOF |
| CN111548377A (en) * | 2020-06-10 | 2020-08-18 | 贵阳单宁科技有限公司 | Novel method for purifying tannic acid |
| CN113484438A (en) * | 2021-07-08 | 2021-10-08 | 宁夏农产品质量标准与检测技术研究所(宁夏农产品质量监测中心) | Method for detecting tannic acid in wine grapes and wines |
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