CN112225658A - Method for extracting oleic acid from tea oil - Google Patents
Method for extracting oleic acid from tea oil Download PDFInfo
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- CN112225658A CN112225658A CN202011087194.5A CN202011087194A CN112225658A CN 112225658 A CN112225658 A CN 112225658A CN 202011087194 A CN202011087194 A CN 202011087194A CN 112225658 A CN112225658 A CN 112225658A
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- Prior art keywords
- tea oil
- oil
- oleic acid
- namely
- extracting
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- 239000010495 camellia oil Substances 0.000 title claims abstract description 58
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 36
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 36
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 36
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 36
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000003921 oil Substances 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 26
- 239000000194 fatty acid Substances 0.000 claims description 26
- 229930195729 fatty acid Natural products 0.000 claims description 26
- 150000004665 fatty acids Chemical class 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000004927 clay Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 235000019198 oils Nutrition 0.000 description 32
- 239000000243 solution Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 2
- 241000526900 Camellia oleifera Species 0.000 description 1
- 235000005295 Elaeagnus orientalis Nutrition 0.000 description 1
- 244000223021 Elaeagnus orientalis Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of tea oil extraction, and particularly relates to a method for extracting oleic acid from tea oil, which comprises the following extraction steps: step one, hydrolysis, namely adding alkaline alcohol water into tea oil, and stirring to hydrolyze the tea oil; and step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 2 and 5, so as to separate an oil layer. According to the invention, through the combination of hydrolysis, layering and liquid separation, the hydrolyzed solution can be layered, so that an oil layer can be completely separated from a residual liquid layer, and the reaction of the rest liquid layers in subsequent steps is prevented, so that the purity of the oil layer is reduced.
Description
Technical Field
The invention belongs to the technical field of tea oil extraction, and particularly relates to a method for extracting oleic acid from tea oil.
Background
The tea oil is obtained from seeds of camellia oleifera trees of the family Theaceae, is also called tea seed oil and camellia oil, is a unique woody oil in China and is mainly distributed in southern provinces such as Hunan, Jiangxi, Guangxi, Guangdong and the like. The fatty acid composition of tea oil is very similar to that of olive oil, the best woody edible plant oil recognized in the world, and thus tea oil is also known as "oriental olive oil". The content of unsaturated fatty acid in the tea oil is up to 90 percent, wherein the content of oleic acid is 75 to 83 percent, the content of linoleic acid is 7.4 to 13 percent, the content of unsaponifiable matters is less than 1 percent, the oleic acid is the highest of all vegetable oil and is an excellent raw material for extracting the oleic acid, in the existing method for extracting the oleic acid from the tea oil, the extraction process of most of the oleic acid is complex, and the extraction process is easily interfered by various factors, so that the content of the extracted oleic acid is lower.
Disclosure of Invention
To solve the problems set forth in the background art described above. The invention provides a method for extracting oleic acid from tea oil, which has the characteristics of simple process and high content of extracted oleic acid.
In order to achieve the purpose, the invention provides the following technical scheme: a method for extracting oleic acid from tea oil comprises the following extraction steps:
step one, hydrolysis, adding alkaline alcohol water into the tea oil, and stirring to hydrolyze the tea oil.
And step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 2 and 5, so as to separate an oil layer.
And step three, separating liquid, namely separating the obtained layered liquid to separate an oil layer.
And step four, washing and drying, washing the separated oil layer with water, adding anhydrous sodium sulfate for drying after the oil layer is washed to be neutral, and hydrolyzing to obtain the tea oil fatty acid oil.
And step five, decoloring, namely uniformly mixing activated clay and the tea oil fatty acid oil, then adding petroleum ether at the temperature of 20-50 ℃, stirring for 30-40min, and finally filtering the activated clay to obtain the treated fatty acid.
And step six, purifying, namely preparing the fatty acid into a to-be-prepared solution of 400mg/ml, and then separating and purifying the to-be-prepared solution by using a chromatographic column.
And seventhly, drying, namely drying the purified solution to obtain high-purity oleic acid, wherein the oleic acid content can reach more than 98%.
Preferably, the alkaline aqueous alcohol is a mixture of sodium hydroxide and aqueous methanol.
Preferably, the weight ratio of the alkaline pure water to the tea oil in the first step is 1: 10, then mixing them evenly, and refluxing them for 2-8 h.
Preferably, the ratio of the mixture to the hydrochloric acid in the second step is 1: 3.
Preferably, the base in the basic alcohol is potassium hydroxide and the alcohol in the basic alcohol is ethanol.
Preferably, the tea oil fatty acid oil in the fifth step is mixed with 0.5-8% of activated clay.
Preferably, petroleum ether is replaced by n-hexane.
Compared with the prior art, the invention has the beneficial effects that:
1. according to the invention, through the combination of hydrolysis, layering and liquid separation, the hydrolyzed solution can be layered, so that an oil layer can be completely separated from a residual liquid layer, the reaction of the rest liquid layers in subsequent steps is prevented, and the purity of the oil layer is reduced.
2. According to the method, the separated oil layer is reacted through the steps of washing, drying, decoloring, purifying and drying, so that the purity of the oleic acid can be improved, and the content of the oleic acid can be improved in the subsequent drying process.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The invention provides the following technical scheme: a method for extracting oleic acid from tea oil comprises the following extraction steps:
step one, hydrolysis, adding alkaline alcohol water into the tea oil, and stirring to hydrolyze the tea oil.
And step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 3, so as to separate an oil layer.
And step three, separating liquid, namely separating the obtained layered liquid to separate an oil layer.
And step four, washing and drying, washing the separated oil layer with water, adding anhydrous sodium sulfate for drying after the oil layer is washed to be neutral, and hydrolyzing to obtain the tea oil fatty acid oil.
And step five, decoloring, namely uniformly mixing activated clay and the tea oil fatty acid oil, then adding petroleum ether at the temperature of 30 ℃, stirring for 30min, and finally filtering to remove the activated clay to obtain the treated fatty acid.
And step six, purifying, namely preparing the fatty acid into 350mg/ml solution to be prepared, and then separating and purifying the solution by using a chromatographic column.
And seventhly, drying, namely drying the purified solution to obtain high-purity oleic acid, wherein the oleic acid content can reach more than 98.1%.
Specifically, the alkaline alcohol water is formed by mixing sodium hydroxide and a methanol aqueous solution, and the weight ratio of the alkaline pure water to the tea oil in the first step is 1: and 10, then uniformly mixing the mixture, and refluxing the mixture for 5 hours, wherein the ratio of the mixture to the hydrochloric acid in the step two is 1: 4.
Specifically, the alkali in the alkaline alcohol can be potassium hydroxide and sodium ethoxide, the alcohol in the alkaline alcohol can be one of ethanol, butanol and isopropanol, the tea oil fatty acid oil in the step five is mixed with 4% of activated clay, and the petroleum ether can be replaced by one of n-hexane and ethyl acetate.
Example 2
The invention provides the following technical scheme: a method for extracting oleic acid from tea oil comprises the following extraction steps:
step one, hydrolysis, adding alkaline alcohol water into the tea oil, and stirring to hydrolyze the tea oil.
And step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 4, so as to separate an oil layer.
And step three, separating liquid, namely separating the obtained layered liquid to separate an oil layer.
And step four, washing and drying, washing the separated oil layer with water, adding anhydrous sodium sulfate for drying after the oil layer is washed to be neutral, and hydrolyzing to obtain the tea oil fatty acid oil.
And step five, decoloring, namely uniformly mixing activated clay and the tea oil fatty acid oil, then adding petroleum ether at the temperature of 40 ℃, stirring for 35min, and finally filtering to remove the activated clay to obtain the treated fatty acid.
And step six, purifying, namely preparing the fatty acid into a to-be-prepared solution of 400mg/ml, and then separating and purifying the to-be-prepared solution by using a chromatographic column.
And seventhly, drying, namely drying the purified solution to obtain high-purity oleic acid, wherein the oleic acid content can reach more than 98.5%.
Specifically, the alkaline alcohol water is formed by mixing sodium hydroxide and a methanol aqueous solution, and the weight ratio of the alkaline pure water to the tea oil in the first step is 1: and 10, then uniformly mixing the mixture, and refluxing the mixture for 7 hours, wherein the ratio of the mixture to hydrochloric acid in the step two is 1:2.
Specifically, the alkali in the alkaline alcohol can be potassium hydroxide and sodium ethoxide, the alcohol in the alkaline alcohol can be one of ethanol, butanol and isopropanol, the tea oil fatty acid oil in the step five is mixed with 6.5% of activated clay, and the petroleum ether can be replaced by one of n-hexane and ethyl acetate.
Example 3
The invention provides the following technical scheme: a method for extracting oleic acid from tea oil comprises the following extraction steps:
step one, hydrolysis, adding alkaline alcohol water into the tea oil, and stirring to hydrolyze the tea oil.
And step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 5, so as to separate an oil layer.
And step three, separating liquid, namely separating the obtained layered liquid to separate an oil layer.
And step four, washing and drying, washing the separated oil layer with water, adding anhydrous sodium sulfate for drying after the oil layer is washed to be neutral, and hydrolyzing to obtain the tea oil fatty acid oil.
And step five, decoloring, namely uniformly mixing activated clay and the tea oil fatty acid oil, then adding petroleum ether at 50 ℃, stirring for 40min, and finally filtering to remove the activated clay to obtain the treated fatty acid.
And step six, purifying, namely preparing the fatty acid into 500mg/ml solution to be prepared, and then separating and purifying the solution by using a chromatographic column.
And seventhly, drying, namely drying the purified solution to obtain high-purity oleic acid, wherein the oleic acid content can reach more than 98.9%.
Specifically, the alkaline alcohol water is formed by mixing sodium hydroxide and a methanol aqueous solution, and the weight ratio of the alkaline pure water to the tea oil in the first step is 1: and 10, then uniformly mixing the mixture, and refluxing the mixture for 7.5 hours, wherein the ratio of the mixture to the hydrochloric acid in the step two is 1: 2.9.
Specifically, the alkali in the alkaline alcohol can be potassium hydroxide and sodium ethoxide, the alcohol in the alkaline alcohol can be one of ethanol, butanol and isopropanol, the tea oil fatty acid oil in the step five is mixed with 7% of activated clay, and the petroleum ether can be replaced by one of n-hexane and ethyl acetate.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A method for extracting oleic acid from tea oil is characterized in that: the method for extracting the oleic acid from the tea oil comprises the following extraction steps:
step one, hydrolysis, namely adding alkaline alcohol water into tea oil, and stirring to hydrolyze the tea oil;
step two, layering, namely adding hydrochloric acid into the hydrolyzed mixture, and adjusting the pH value of the hydrolyzed mixture to be between 2 and 5, so as to separate an oil layer;
step three, separating liquid, namely separating the obtained layered liquid to separate an oil layer;
washing and drying, namely washing the separated oil layer with water, adding anhydrous sodium sulfate to dry after the oil layer is washed to be neutral, and hydrolyzing to obtain the tea oil fatty acid oil;
step five, decoloring, namely uniformly mixing activated clay and tea oil fatty acid oil, then adding petroleum ether at the temperature of 20-50 ℃, stirring for 30-40min, and finally filtering the activated clay to obtain treated fatty acid;
step six, purifying, namely preparing the fatty acid into a to-be-prepared solution of 400mg/ml, and then separating and purifying the to-be-prepared solution by using a chromatographic column;
and seventhly, drying, namely drying the purified solution to obtain high-purity oleic acid, wherein the oleic acid content can reach more than 98%.
2. The method for extracting oleic acid from tea oil according to claim 1, wherein: the alkaline alcohol water is formed by mixing sodium hydroxide and a methanol water solution.
3. The method for extracting oleic acid from tea oil according to claim 1, wherein: the weight ratio of the alkaline pure water to the tea oil in the first step is 1: 10, then mixing them evenly, and refluxing them for 2-8 h.
4. The method for extracting oleic acid from tea oil according to claim 1, wherein: in the second step, the mixture and the hydrochloric acid are mixed in a ratio of 1: 3.
5. The method for extracting oleic acid from tea oil according to claim 1, wherein: the alkali in the alkaline alcohol is potassium hydroxide, and the alcohol in the alkaline alcohol is ethanol.
6. The method for extracting oleic acid from tea oil according to claim 1, wherein: and mixing the tea oil fatty acid oil obtained in the step five with 0.5-8% of activated clay.
7. The method for extracting oleic acid from tea oil according to claim 1, wherein: petroleum ether can also be replaced by n-hexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011087194.5A CN112225658A (en) | 2020-10-12 | 2020-10-12 | Method for extracting oleic acid from tea oil |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011087194.5A CN112225658A (en) | 2020-10-12 | 2020-10-12 | Method for extracting oleic acid from tea oil |
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| CN202011087194.5A Pending CN112225658A (en) | 2020-10-12 | 2020-10-12 | Method for extracting oleic acid from tea oil |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845362A (en) * | 2010-06-22 | 2010-09-29 | 中南林业科技大学 | Method for gathering oleic acid from tea-seed oil |
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN107739296A (en) * | 2017-09-30 | 2018-02-27 | 武汉欧米嘉生物医药有限公司 | A kind of method that oleic acid is collected from tea oil |
| CN108753466A (en) * | 2018-05-24 | 2018-11-06 | 华南理工大学 | A kind of tea oil linoleic acid and its preparation method and application |
-
2020
- 2020-10-12 CN CN202011087194.5A patent/CN112225658A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845362A (en) * | 2010-06-22 | 2010-09-29 | 中南林业科技大学 | Method for gathering oleic acid from tea-seed oil |
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN107739296A (en) * | 2017-09-30 | 2018-02-27 | 武汉欧米嘉生物医药有限公司 | A kind of method that oleic acid is collected from tea oil |
| CN108753466A (en) * | 2018-05-24 | 2018-11-06 | 华南理工大学 | A kind of tea oil linoleic acid and its preparation method and application |
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