CN111548377A - Novel method for purifying tannic acid - Google Patents
Novel method for purifying tannic acid Download PDFInfo
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- CN111548377A CN111548377A CN202010525844.3A CN202010525844A CN111548377A CN 111548377 A CN111548377 A CN 111548377A CN 202010525844 A CN202010525844 A CN 202010525844A CN 111548377 A CN111548377 A CN 111548377A
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- tannic acid
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- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000001263 FEMA 3042 Substances 0.000 title claims abstract description 47
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 title claims abstract description 47
- 235000015523 tannic acid Nutrition 0.000 title claims abstract description 47
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 title claims abstract description 47
- 229940033123 tannic acid Drugs 0.000 title claims abstract description 47
- 229920002258 tannic acid Polymers 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 87
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000001914 filtration Methods 0.000 claims abstract description 17
- 229940074391 gallic acid Drugs 0.000 claims abstract description 16
- 235000004515 gallic acid Nutrition 0.000 claims abstract description 16
- 239000000741 silica gel Substances 0.000 claims abstract description 11
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 7
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 229920001864 tannin Polymers 0.000 description 4
- 239000001648 tannin Substances 0.000 description 4
- 235000018553 tannin Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 240000003152 Rhus chinensis Species 0.000 description 2
- 235000014220 Rhus chinensis Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 244000307697 Agrimonia eupatoria Species 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000134400 Cotinus coggygria Species 0.000 description 1
- 235000015489 Emblica officinalis Nutrition 0.000 description 1
- 241000208690 Hamamelis Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 235000014360 Punica granatum Nutrition 0.000 description 1
- 240000004980 Rheum officinale Species 0.000 description 1
- 235000008081 Rheum officinale Nutrition 0.000 description 1
- 244000173853 Sanguisorba officinalis Species 0.000 description 1
- 235000008282 Sanguisorba officinalis Nutrition 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 241000388430 Tara Species 0.000 description 1
- 244000277583 Terminalia catappa Species 0.000 description 1
- 235000011517 Terminalia chebula Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 235000000125 common agrimony Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a novel method for purifying tannic acid, which comprises the steps of dissolving a crude tannic acid product in water, extracting with ethyl acetate, adding a certain amount of organic base or inorganic base or mixed base, fully stirring for reaction, filtering with silica gel or diatomite, continuously extracting with ethyl acetate for 3 times to obtain an ethyl acetate layer, combining the ethyl acetate layers, adding anhydrous sodium sulfate, removing the solvent by a reduced pressure distillation method, and drying in vacuum to obtain high-purity tannic acid, wherein the purity of the tannic acid obtained by the method disclosed by the invention can reach more than 99%, and the total content of gallic acid and pyro-beige acid is lower than 0.2%.
Description
Technical Field
The invention relates to a purification process research of tannic acid, in particular to a purification method for effectively removing impurities of gallic acid and pyromucic acid in tannic acid.
Technical Field
Tannic acid is present in the bark and fruit of various trees, such as Chinese gall, Turkey gall, tara pod, pomegranate, sumac leaf, cotinus coggygria, hamamelis, etc., and is also the main component of galls (galls) generated by insect attack on these trees, and the content is 50% -70%. In addition, more than 70% of the herbs such as sanguisorba officinalis, rheum officinale, myrobalan, cinnamon, mango, agrimony and the like contain a large amount of tannic acid. The tannic acid is widely applied to the fields of medicine, wine brewing, beverages, tanning, metallurgy, daily chemical industry and the like, and particularly, the high-purity tannic acid product has larger market demand. At present, the domestic tannin purification process mainly comprises unit purification methods such as activated carbon adsorption, macroporous resin adsorption, membrane separation technology, ion exchange technology, molecular distillation technology, freeze clarification, solvent extraction and the like and a multi-element combined purification method, wherein the activated carbon adsorption can generate a large amount of waste carbon, the activated carbon can also adsorb a large amount of tannin, the activated carbon is difficult to separate, and only 1% of gallic acid can be removed while the yield is low; macroporous resin adsorption is not suitable for large-scale industrial production, meanwhile, operation is inconvenient, a large amount of macroporous resin waste can be generated, and the separation effect of gallic acid is not ideal; the membrane separation technology is not suitable for industrial production, and the membrane is easy to block; ion exchange techniques have the same problems as macroporous resins; the molecular distillation technology has low efficiency, large power consumption, high cost and undesirable effect; in the freezing technology, under the condition that only 1 to 4 percent of gallic acid is contained and hydrogen bonds are formed between tannic acid and gallic acid molecules, the gallic acid cannot be removed and the requirement on the conditions is high; solvent extraction can only remove gums and proteins, but not gallic acid; although the multi-component combined purification method has relatively good effect, the method has multiple operation steps, low total yield and high production cost, is not suitable for industrial production, and is only suitable for preparing food-grade tannic acid in small quantity.
Disclosure of Invention
The invention aims to solve the problem of providing a method for purifying high-purity tannic acid, which has the advantages of simple process, convenient operation, low cost, high content of tannic acid and capability of effectively removing impurities of gallic acid and pyromucic acid.
The invention can limit the total content of gallic acid and pyro-acid in the tannic acid by controlling the amount of alkali. The technical scheme adopted for achieving the purpose is as follows:
a novel method for purifying tannic acid, the method comprising the steps of:
step A, dissolving, namely dissolving by using pure water, adding pure water according to the mass ratio of the crude tannic acid to the pure water of 1/2.5-5 to dissolve the crude tannic acid, stirring for 0.5-1 hour, and filtering insoluble impurities to obtain a solution A;
step B, deacidifying, namely adding organic base or inorganic base or mixed base into the solution A, stirring for 1-2 hours, then adding ethyl acetate for reaction, filtering by using silica gel or diatomite after the reaction to obtain a mixed solution of ethyl acetate and water, standing and separating to obtain an ethyl acetate layer, continuously adding ethyl acetate into a water layer for extraction, continuously extracting for 2 times, and combining the obtained ethyl acetate layers to obtain a solution B;
and C, drying and concentrating, adding anhydrous sodium sulfate into the solution B, standing for 1-2 h, removing the solvent by adopting a reduced pressure distillation method, and drying in vacuum to obtain a pure product of the tannic acid.
The pure water in the step A is deionized water, and the temperature of the water is-20 ℃ to 50 ℃.
The organic base in the step B comprises any one or a combination of more of triethylamine, sodium citrate, diethylamine, N-dimethylethylamine, N-dimethylethylenediamine amine, pyridine, piperidine and 4-methylpiperidine; the inorganic base includes NaOH, KOH, Mg (OH)2、Na2CO3、K2CO3、Li2CO3、Na3PO4、K3PO4、NaHCO3、LiOH、CsCO3Ammonia water, NH4OH、KHCO3、LiHCO3、NaHCO3One or more combinations thereof.
And in the step B, the weight part of the added organic base or inorganic base or mixed base is 2-10% of the weight of the solution A.
And B, adding ethyl acetate in the step B, wherein the weight of the ethyl acetate is 3-5 times of the mass of the crude product of the tannic acid.
The mesh number of the silica gel in the step B is 60-300 meshes.
And D, adding anhydrous sodium sulfate into the solution B in the step C, wherein the mass of the anhydrous sodium sulfate is 15-30% of that of the crude tannic acid.
And C, performing reduced pressure distillation at the temperature of 40-60 ℃ in the step C, wherein the vacuum degree of vacuum drying is-0.85-0.95 Mpa.
The purity of the purified product of tannic acid prepared by the method is more than 99%, and the total content of gallic acid and pyro-pakc is less than 0.2%.
Drawings
FIG. 1 is a chromatogram of the purity of tannic acid from Omnichem, Belgium.
FIG. 2 is a chromatogram of the purity of tannic acid sold by a company in China.
FIG. 3 is a chromatogram showing the purity of purified tannic acid in example 1 of the present invention.
Detailed description of the preferred embodiments
Example 1
Dissolving 100g of crude tannic acid in 500mL of water, stirring for 0.5h, filtering, slowly dropwise adding 1M NaOH solution into a water layer until the content of gallic acid is lower than 0.2% by HPLC (high performance liquid chromatography), stopping dropwise adding, adding 300mL of ethyl acetate, stirring for 1h, filtering by using a 1000mL Buchner funnel paved with a layer of silica gel or diatomite, washing a silica gel layer or a diatomite layer by using 500mL of ethyl acetate after filtering, separating to obtain an organic layer, extracting once by using 200mL of ethyl acetate and 100mL of ethyl acetate respectively, combining three organic phases, drying by using 20g of anhydrous sodium sulfate, standing for 2 h, filtering, decompressing to remove a solvent, and drying in vacuum to obtain high-purity tannic acid, wherein the content of tannic acid is higher than 99%, and the total content of gallic acid and pyrogallol is lower than 0.2%, which is shown in figure 1.
Example 2
Dissolving 100g crude tannic acid in 500mL water, stirring for 0.5h, filtering, adding saturated NaHCO dropwise into water layer3Adding 300mL of ethyl acetate into the aqueous solution until no bubbles are generated, stirring for 1h, filtering by using a 1000mL Buchner funnel paved with a layer of silica gel or diatomite, washing a silica gel layer or a diatomite layer by using 100mL of ethyl acetate after filtering, separating the liquid into an organic layer, respectively extracting once by using 200mL of ethyl acetate and 100mL of ethyl acetate, combining three organic phases, drying by using 20g of anhydrous sodium sulfate, standing for 2 h, filtering, decompressing to remove the solvent, and drying in vacuum to obtain the high-purity tannic acid, wherein the content of the tannic acid is more than 99%, and the total content of the gallic acid and the pyromucic acid is lower than that of the high-purity0.2%。
Example 3
Dissolving 100g of crude tannic acid in 500mL of water, stirring for 1h, filtering, adding dropwise saturated aqueous ammonia solution into a water layer until no bubbles are generated, adding 500mL of ethyl acetate, stirring for 1h, filtering with a 1000mL Buchner funnel paved with a layer of silica gel or diatomite, washing a silica gel layer or a diatomite layer with 100mL of ethyl acetate after filtering, separating to an organic layer, extracting with 200mL of ethyl acetate and 100mL of ethyl acetate respectively once, combining three organic phases, drying with 20g of anhydrous sodium sulfate, standing for 2 h, filtering, removing the solvent under reduced pressure, and vacuum drying to obtain the high-purity tannic acid, wherein the content of tannic acid is more than 99%, and the total content of gallic acid and pyromucic acid is less than 0.2%.
In order to further verify the remarkable progress of the method of the present invention, tannic acid (sample No. 1) by omnihem, belgium, tannic acid sold by a certain domestic company (sample No. 2), and a purified product of tannic acid purified by the method of example 1 of the present invention (sample No. 3) were analyzed by HPLC. The instrument is Agilent 1260 high performance liquid chromatography, and the chromatographic conditions are as follows: eluent is 0.3% phosphoric acid aqueous solution: methanol = 75: 25, elution time 10 minutes, column temperature 30 ℃ and wavelength 276. The purity of the three tannins obtained by the analysis is shown in table 1, and the chromatograms are shown in fig. 1-3.
TABLE 1 comparison of the purity of tannins obtained by different purification methods
Claims (10)
1. A novel method for purifying tannic acid, comprising the steps of:
step A, dissolving, namely dissolving by using pure water, adding pure water according to the mass ratio of the crude tannic acid to the pure water of 1/2.5-5 to dissolve the crude tannic acid, stirring for 0.5-1 hour, and filtering insoluble impurities to obtain a solution A;
step B, deacidifying, namely adding organic base or inorganic base or mixed base into the solution A, stirring for 1-2 hours, then adding ethyl acetate for reaction, filtering by using silica gel or diatomite after the reaction to obtain a mixed solution of ethyl acetate and water, standing and separating to obtain an ethyl acetate layer, continuously adding ethyl acetate into a water layer for extraction, continuously extracting for 2 times, and combining the obtained ethyl acetate layers to obtain a solution B;
and C, drying and concentrating, adding anhydrous sodium sulfate into the solution B, standing for 1-2 h, removing the solvent by adopting a reduced pressure distillation method, and drying in vacuum to obtain a pure product of the tannic acid.
2. The method as claimed in claim 1, wherein the pure water in step A is deionized water and the water temperature is-20 ℃ to 50 ℃.
3. The novel method for purifying tannic acid of claim 1, wherein the organic base in step B comprises any one or more of triethylamine, sodium citrate, diethylamine, N-dimethylethylamine, N-dimethylethylenediamine, pyridine, piperidine, and 4-methylpiperidine; the inorganic base includes NaOH, KOH, Mg (OH)2、Na2CO3、K2CO3、Li2CO3、Na3PO4、K3PO4、NaHCO3、LiOH、CsCO3Ammonia water, NH4OH、KHCO3、LiHCO3、NaHCO3One or more combinations thereof.
4. The method of claim 1, wherein the anhydrous sodium sulfate is added when the purity is above 99%.
5. The method as claimed in claim 1, wherein the weight portion of the organic base or inorganic base or mixed base added in step B is 2-10% of the weight of the solution A.
6. The method as claimed in claim 1, wherein the amount of ethyl acetate added in step B is 3-5 times the weight of the crude tannic acid.
7. The method as claimed in claim 1, wherein the silica gel in step B has a mesh size of 60-300 mesh.
8. The method as claimed in claim 1, wherein the mass of the anhydrous sodium sulfate added to the solution B in the step C is 15-30% of the crude product of tannic acid.
9. The method as claimed in claim 1, wherein the temperature of the vacuum distillation in step C is 40-60 deg.C, and the vacuum degree of vacuum drying is-0.85-0.95 MPa.
10. The method as claimed in any one of claims 1 to 7, wherein the purity of the purified tannic acid is greater than 99% and the total content of gallic acid and pyro-gallic acid is less than 0.2%.
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| CN1398871A (en) * | 2002-09-10 | 2003-02-26 | 北京富邦博尔生物科技有限公司 | Tannic acid purifying process |
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| CN105622679A (en) * | 2014-10-31 | 2016-06-01 | 陕西启源科技发展有限责任公司 | Preparation method of edible tannic acid |
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