CN101781216A - Novel process for preparing propylgallate directly from gallnuts - Google Patents
Novel process for preparing propylgallate directly from gallnuts Download PDFInfo
- Publication number
- CN101781216A CN101781216A CN200910226621A CN200910226621A CN101781216A CN 101781216 A CN101781216 A CN 101781216A CN 200910226621 A CN200910226621 A CN 200910226621A CN 200910226621 A CN200910226621 A CN 200910226621A CN 101781216 A CN101781216 A CN 101781216A
- Authority
- CN
- China
- Prior art keywords
- tenox
- preparing
- gallnuts
- propylgallate
- filtrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 235000010388 propyl gallate Nutrition 0.000 title claims abstract description 8
- 239000000473 propyl gallate Substances 0.000 title claims abstract description 7
- 229940075579 propyl gallate Drugs 0.000 title claims abstract description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000007670 refining Methods 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims description 17
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 230000011218 segmentation Effects 0.000 claims description 2
- 239000002594 sorbent Substances 0.000 claims description 2
- 238000009834 vaporization Methods 0.000 claims description 2
- 230000008016 vaporization Effects 0.000 claims description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract description 28
- 229940074391 gallic acid Drugs 0.000 abstract description 14
- 235000004515 gallic acid Nutrition 0.000 abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000012043 crude product Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000004065 wastewater treatment Methods 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- 239000010842 industrial wastewater Substances 0.000 abstract description 2
- 239000010865 sewage Substances 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- -1 Gallic acid ester Chemical class 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 2
- 241000208225 Rhus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 1
- 241001518926 Cladrastis Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 235000014220 Rhus chinensis Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 229920001461 hydrolysable tannin Polymers 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000007063 yellowwood Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a novel process for preparing propylgallate directly from gallnuts. The process comprises: taking horned galls or gallnuts as raw materials; performing extraction at room temperature through n-propanol; performing decoloration through activated carbon and refined kieselguhr adsorbent; obtaining a crude product by subjecting the obtained product and supersaturated n-propanol to chemical reaction under the catalysis of an acid catalyst; and refining and drying the crude product. The process has the advantages of adopting gallnut raw materials to react with n-propanol for preparing the propylgallate, ensuring high product yield, less impurity and good edible medicinal safety of products, reducing the consumption of acidic/alkaline activated carbon and other auxiliary materials, greatly reducing production cost, avoiding high-concentration sewage discharge caused during the preparation of gallic acid, reducing the pressure of industrial wastewater treatment and contributing to environmental management and protection.
Description
Technical field
The present invention relates to a kind of method for preparing Tenox PG, particularly by the method for natural product preparing propylgallate directly from gallnuts.
Background technology
Turkey-galls is the insect gall that the Turkey-galls aphid colonizes in stimulates the leaf cell hyperplasia to form on several summer host plant compound leaves such as the blue or green bran poplar of Anacardiaceae Rhus, Root of Redpunjab Sumac and yellow wood, is China's important resource insect product, the conventional Chinese medicine material that state-promulgated pharmacopoeia is recorded.
Turkey-galls is a biological organism.Main organic components is a Chinese tannin, and the angle doubly reaches 66.6%, and tripe doubly reaches 72.5%, and doubly flower reaches 36.6%.Chinese tannin belongs to the hydrolyzable tannin, under the effect of acid, alkali or enzyme, hydrolyzable becomes gallic acid and polyvalent alcohol, can prepare the various derivatives relevant with gallic acid thus, becomes the precursor of multiple synthetic drugs, important fine chemical products such as foodstuff additive.
Tenox PG is a gallic acid esterification derivative, be excellent property, antioxidant safe in utilization, be widely used in vegetables oil, animal tallow, food, medicine and the makeup, being made as lipid by U.S. FDA and the FAO of Food and Argriculture OrganizationFAO and the WHO of World Health Organization approval or be rich in the antioxidant of oily based food, is the legal antioxidant of the European Community.Gallic acid ester still is good free-radical scavengers, can delay body aging, suppresses the hepatic tissue lipid peroxidation, and liver injury has provide protection.That Tenox PG also has is antimicrobial, platelet aggregation-against, multiple pharmacologically active such as anticancer, in recent years as the bulk drug and the pharmaceutical excipient of the Gallate propyl ester preparation of soldier, coronary heart disease, diabetes in the control brain.
At present, how industrial preparation Tenox PG draws powder with Turkey-galls or import tower is raw material, and acidifying, alkalization or enzymeization prepare gallic acid, are that precursor and n-propyl alcohol esterification are synthesized into again with the gallic acid.The production method technical process is long, and supplementary product onsumptions such as gallic acid raw material and soda acid and gac are big, and environmental pollution is serious, the cost for wastewater treatment height.
Summary of the invention
The object of the present invention is to provide a kind ofly directly to prepare the method for synthesizing gallic acid propyl ester by Turkey-galls, technical process is short, and supplies consumption is few, and production cost is low, and is environmentally friendly.
The present invention with the Turkey-galls angle doubly or tripe doubly be raw material, under an acidic catalyst catalysis, realize by chemical reaction that with the supersaturation n-propyl alcohol step comprises:
(1) powder essence: with Turkey-galls raw material sorting removal of impurities deironing, powder essence is standby to the 30-50 order.
(2) lixiviate: gallnut extract is put into extractor, add gallnut extract weight 6-10 n-propyl alcohol doubly, stir, at room temperature soak and extracted 4-6 hour.
(3) rough: the lixiviate feed liquid is filtered, filtrate is gone into retort, the smart diatomite adsorbant decolouring that adds gac and the 5-10% of gallnut extract weight 3-5%, remove by filter sorbent material, the an acidic catalyst that adds gallnut extract weight 5-10% in the filtrate, 70-90 ℃ was reacted 3-5 hour down, cool to room temperature, filtering and impurity removing matter, filtrate are at 120 ℃ of following reduction vaporizations, and the polynary azeotropic of segmentation reclaims n-propyl alcohol, add 5-10 times of water in the enriched material, heating cooled to 5-15 ℃ of crystallization 5-8 hour after making its dissolving, and crystallization centrifuging gets the Tenox PG coarse-grain.
(4) refining: the Tenox PG coarse-grain is put into retort; with 8-12 times of water; 60-90 ℃ of dissolving, the gac of adding mixing solutions weight 1-3% in the solution, decolouring, filtration; get filtrate; be cooled to 5-15 ℃ of crystallization 5-8 hour, the centrifuging dehydration is with pure water thorough washing material; until PH is that 6.0-7.0 gets final product, and dewaters to shut down in 1 hour and gets material.
(5) drying: the wet crystal of Tenox PG changes the vacuum drier drying over to, gets the Tenox PG product.
Described an acidic catalyst is that concentration is 80% sulfuric acid.
The present invention is direct and n-propyl alcohol supersaturation prepared in reaction Tenox PG with the natural product Turkey-galls, has following advantage:
1, adopting the high natural product Turkey-galls of gallic acid content is raw material and n-propyl alcohol prepared in reaction Tenox PG, and it is good that product yield height, impurity are few, product eats medicinal security.
2, save the multiple working procedure that Turkey-galls prepares gallic acid, reduced supplementary product onsumptions such as soda acid gac, greatly reduced production cost, favourablely improved clean environment production.
3, avoided preparing the high-concentration sewage discharging that causes in the gallic acid process, alleviated Industrial Wastewater Treatment pressure, enabling environment is administered and protection.
Embodiment
The invention will be further described below in conjunction with embodiment.
Embodiment 1:
Raw material Turkey-galls angle doubly, powder essence is crossed 40 mesh sieves, gets 1000 milliliters of angle times powder 100g, n-propyl alcohols, in 50 ℃ stir extract 4 hours after, add 5g gac, the smart diatomite adsorbant decolouring of 10g 30 minutes in the feed liquid, subsequently vacuum filtration.It is 25 milliliters in 80% sulfuric acid that filtrate adds catalyst concn, 80 ℃ down reaction be cooled to 20 ℃ of filtrations after 5 hours, filtrate evaporated under reduced pressure concentrates, and reclaims the solvent n-propyl alcohol that steams; Concentrate material with 80 ℃ of 500mL hot water dissolvings, stir, be cooled to 15 ℃, crystallization centrifuging, gallic acid propyl alcohol 56.8g is wet brilliant, crude product is with 750 ml water heating for dissolving, with 2g activated carbon decolorizing 30 minutes, vacuum filtration, filtrate is cooled to 10 ℃ of crystallizations 5 hours, centrifuging, washing material is 6.0-7.0 until PH, gets filter cake, vacuum-drying (60 ℃), get Tenox PG finished product 32.6g, content 99.5%.
Embodiment 2:
Raw material Turkey-galls tripe doubly, powder essence is crossed 40 mesh sieves, gets 1000 milliliters of tripe times powder 100g, n-propyl alcohols, in 50 ℃ stir extract 4 hours after, add 5g gac, the smart diatomite adsorbant decolouring of 10g 30 minutes in the feed liquid, subsequently vacuum filtration.Filtrate adds 25 milliliters of catalyst sulfuric acids, and 80 ℃ are reacted after 5 hours down, are cooled to 20 ℃ of filtrations, and filtrate evaporated under reduced pressure concentrates, and reclaims the solvent n-propyl alcohol that steams; Concentrate material with 80 ℃ of 500mL hot water dissolvings, stir, be cooled to 15 ℃, crystallization centrifuging, gallic acid propyl alcohol 61.2g is wet brilliant, crude product is with 750 ml water heating for dissolving, with 2g activated carbon decolorizing 30 minutes, vacuum filtration, filtrate is cooled to 10 ℃ of crystallizations 5 hours, centrifuging, washing material is 6.0-7.0 until PH, gets filter cake, vacuum-drying (60 ℃), get Tenox PG finished product 35.4g, content 99.2%.
Embodiment 3:
Raw material Turkey-galls angle doubly, powder essence is crossed 40 mesh sieves, gets 600 milliliters of angle times powder 100g, n-propyl alcohols, in 50 ℃ stir extract 4 hours after, add 5g gac, the smart diatomite adsorbant decolouring of 10g 30 minutes in the feed liquid, subsequently vacuum filtration.Filtrate adds catalyzer and adds 25 milliliters in sulfuric acid, and 80 ℃ are reacted after 5 hours down, are cooled to 20 ℃ of filtrations, and filtrate evaporated under reduced pressure concentrates, and reclaims the solvent n-propyl alcohol that steams; Concentrate material with 80 ℃ of 500mL hot water dissolvings, stir, be cooled to 15 ℃, crystallization centrifuging, gallic acid propyl alcohol 51.6g is wet brilliant, crude product is with 450 ml water heating for dissolving, with 2g activated carbon decolorizing 30 minutes, vacuum filtration, filtrate is cooled to 10 ℃ of crystallizations 5 hours, centrifuging, washing material is 6.0-7.0 until PH, gets filter cake, vacuum-drying (60 ℃), get Tenox PG finished product 30.4g, content 98.5%.
Claims (2)
1. novel process for preparing propylgallate directly from gallnuts is characterized in that step comprises:
(1) powder essence: with Turkey-galls raw material sorting removal of impurities deironing, powder essence is standby to the 30-50 order.
(2) lixiviate: gallnut extract is put into extractor, add gallnut extract weight 6-10 n-propyl alcohol doubly, stir, at room temperature soak and extracted 4-6 hour.
(3) rough: the lixiviate feed liquid is filtered, filtrate is gone into retort, the smart diatomite adsorbant decolouring that adds gac and the 5-10% of gallnut extract weight 3-5%, remove by filter sorbent material, the an acidic catalyst that adds gallnut extract weight 5-10% in the filtrate, 70-90 ℃ was reacted 3-5 hour down, cool to room temperature, filtering and impurity removing matter, filtrate are at 120 ℃ of following reduction vaporizations, and the polynary azeotropic of segmentation reclaims n-propyl alcohol, add 5-10 times of water in the enriched material, heating cooled to 5-15 ℃ of crystallization 5-8 hour after making its dissolving, and crystallization centrifuging gets the Tenox PG coarse-grain.
(4) refining: the Tenox PG coarse-grain is put into retort; with 8-12 times of water; 60-90 ℃ of dissolving, the gac of adding mixing solutions weight 1-3% in the solution, decolouring, filtration; get filtrate; be cooled to 5-15 ℃ of crystallization 5-8 hour, the centrifuging dehydration is with pure water thorough washing material; until PH is that 6.0-7.0 gets final product, and dewaters to shut down in 1 hour and gets material.
(5) drying: the wet crystal of Tenox PG changes the vacuum drier drying over to, gets the Tenox PG product.
2. novel process for preparing propylgallate directly from gallnuts according to claim 1 is characterized in that, described an acidic catalyst is that concentration is 80% sulfuric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910226621 CN101781216B (en) | 2009-12-10 | 2009-12-10 | Novel process for preparing propylgallate directly from gallnuts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910226621 CN101781216B (en) | 2009-12-10 | 2009-12-10 | Novel process for preparing propylgallate directly from gallnuts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101781216A true CN101781216A (en) | 2010-07-21 |
| CN101781216B CN101781216B (en) | 2013-07-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910226621 Active CN101781216B (en) | 2009-12-10 | 2009-12-10 | Novel process for preparing propylgallate directly from gallnuts |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351705A (en) * | 2011-08-25 | 2012-02-15 | 江西新先锋医药有限公司 | Propylgallate compound and pharmaceutical composition thereof |
| CN102988421A (en) * | 2012-11-21 | 2013-03-27 | 江苏大学 | Extract of effective components of antineoplastic gallnut as well as preparation method and application thereof |
| CN106187762A (en) * | 2016-06-30 | 2016-12-07 | 宁波市江东林清环保科技有限公司 | A kind of preparation method of propylgallate |
| CN111848393A (en) * | 2020-06-17 | 2020-10-30 | 遵义市倍缘化工有限责任公司 | Method for treating wastewater from production of gallic acid and propyl gallate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1887850A (en) * | 2006-07-24 | 2007-01-03 | 乐山三江生化科技有限公司 | Direct synthesis process of propyl gallate with Tala powder |
-
2009
- 2009-12-10 CN CN 200910226621 patent/CN101781216B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1887850A (en) * | 2006-07-24 | 2007-01-03 | 乐山三江生化科技有限公司 | Direct synthesis process of propyl gallate with Tala powder |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351705A (en) * | 2011-08-25 | 2012-02-15 | 江西新先锋医药有限公司 | Propylgallate compound and pharmaceutical composition thereof |
| CN102988421A (en) * | 2012-11-21 | 2013-03-27 | 江苏大学 | Extract of effective components of antineoplastic gallnut as well as preparation method and application thereof |
| CN102988421B (en) * | 2012-11-21 | 2015-06-10 | 江苏大学 | Extract of effective components of antineoplastic gallnut as well as preparation method and application thereof |
| CN106187762A (en) * | 2016-06-30 | 2016-12-07 | 宁波市江东林清环保科技有限公司 | A kind of preparation method of propylgallate |
| CN106187762B (en) * | 2016-06-30 | 2019-01-11 | 河北兴润生物科技股份有限公司 | A kind of preparation method of propylgallate |
| CN111848393A (en) * | 2020-06-17 | 2020-10-30 | 遵义市倍缘化工有限责任公司 | Method for treating wastewater from production of gallic acid and propyl gallate |
| CN111848393B (en) * | 2020-06-17 | 2023-06-06 | 遵义市倍缘化工有限责任公司 | Treatment method of wastewater from gallic acid and propyl gallate production |
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| Publication number | Publication date |
|---|---|
| CN101781216B (en) | 2013-07-17 |
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Address after: 427000 Xixi Zhangjiajie economic and Technological Development Zone, Yongding District, Zhangjiajie, Hunan Patentee after: JIURUI BIOLOGY & CHEMISTRY CO.,LTD. Address before: 427000 Xixi Zhangjiajie economic and Technological Development Zone, Yongding District, Zhangjiajie, Hunan Patentee before: ZHANGJIAJIE AOWEI SCIENCE & TECHNOLOGY Co.,Ltd. |
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Denomination of invention: Direct Preparation of Propyl gallate from Galla Chinensis Effective date of registration: 20230628 Granted publication date: 20130717 Pledgee: Bank of Communications Co.,Ltd. Zhangjiajie branch Pledgor: JIURUI BIOLOGY & CHEMISTRY CO.,LTD. Registration number: Y2023980046143 |
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Denomination of invention: Direct preparation process of propyl gallate from gallnuts Granted publication date: 20130717 Pledgee: Bank of Communications Co.,Ltd. Zhangjiajie branch Pledgor: JIURUI BIOLOGY & CHEMISTRY CO.,LTD. Registration number: Y2024980025097 |
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