CN109267088A - A kind of method of dihydromyricetin dehydrogenation - Google Patents
A kind of method of dihydromyricetin dehydrogenation Download PDFInfo
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- CN109267088A CN109267088A CN201811032759.2A CN201811032759A CN109267088A CN 109267088 A CN109267088 A CN 109267088A CN 201811032759 A CN201811032759 A CN 201811032759A CN 109267088 A CN109267088 A CN 109267088A
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- dihydromyricetin
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- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
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Abstract
The present invention relates to organic synthesis fields, and in particular to a kind of method of dihydromyricetin dehydrogenation, comprising the following steps: the pre-treatment of S01. electrode；S02. graphene formic acid benzene methanesulfonic acid modified in the electrode face finish that step S1 is obtained；S03. the cathode of modified electrode connection power supply step S2 obtained, the anode connection inert electrode of power supply；S04. it by the electrolysis system of step S3, is put into the solution containing dihydromyricetin；S05. electrolyte is put into ice domain after static 12 ~ 15h and is filtered.Promote the generation of dihydromyricetin dehydrogenation reaction using the method for electrochemistry.Reaction carries out being more advantageous to dihydromyricetin dehydrogenation under alkaline condition.The process of entire dihydromyricetin dehydrogenation has high conversion rate, the fast feature of conversion rate.
Description
Technical field
The present invention relates to organic synthesis fields, and in particular to a kind of method of dihydromyricetin dehydrogenation.
Background technique
Dihydromyricetin (3,5,7,3',4',5'-hexahydroxy-2,3-dihydroflavonol, dihydromyricetin,
DMY) DMY) it is a kind of polyphenol hydroxyl flavanonol, also known as ampelopsin, belong to flavone compound.Data shows dihydro poplar
Syphilis is largely present in Vitaceae ampelopsis, such as vine tea, that is, ampelopsis grossdentata, ampelopsis cantoniensis), leatherleaf porcelain ampelopsis,
Porcelain ampelopsis, Northeastern Caulis seu folium ampelopsis brevipedunculatae, Ampelopsis etc., wherein vine tea is especially special.Be distributed widely in China Guangdong, Guangxi,
In the young young stem and leaf of the porcelain ampelopsis of the provinces and regions such as Yunnan, Hunan, Hubei, Jiangxi, find two in its spring and summer children's young stem and leaf
The content of hydrogen myricetin reaches 20 % or more of sample dry weight, and the lobus cardiacus in spire is up to 40 % or more.
Currently, dihydromyricetin available on the market and myricetin, are mainly derived from the extraction of vine tea plant.For dihydro
For myricetin, since its content in vine tea is higher, extracting resulting dihydromyricetin can satisfy the demand in market.And
The source of myricetin is mainly strawberry tree, is the peculiar resource in China, still, since extraction process etc. is ready, at present for poplar
The research of syphilis is mainly derived from vine tea.
In view of the content of dihydromyricetin from Ampelopsis grossedentata is up to 25%, very big conversion space is remained.Therefore, one kind is developed
The conversion new method of dihydromyricetin to myricetin is to solve myricetin market top priority in short supply.
Summary of the invention
It is an object of the invention to overcome above-mentioned technical problem, it is supplied to a kind of method of dihydromyricetin dehydrogenation.
The purpose of the present invention is achieved by the following technical programs:
A kind of method of dihydromyricetin dehydrogenation, comprising the following steps:
S01. the pre-treatment of electrode；
S02. graphene formic acid benzene methanesulfonic acid modified in the electrode face finish that step S1 is obtained；
S03. the cathode of modified electrode connection power supply step S2 obtained, the anode connection inert electrode of power supply；
S04. it by the electrolysis system of step S3, is put into the solution containing dihydromyricetin；
S05. electrolyte is put into ice domain after static 12 ~ 15h and is filtered.
A kind of method of dihydromyricetin dehydrogenation, by, to methylbenzenesulfonic acid, then passing through electrification in electrode face finish
Learn the dehydrogenation reaction that reaction promotes dihydromyricetin.The graphene of the formic acid benzene methanesulfonic acid modification of electrode face finish, in electric current
Under the action of decompose and generate sulfur dioxide, then sulfur dioxide chemically reacts on negative electrode surface, and the transmitting of electronics is led to
External circuit completion is crossed, in anode electrode surface dehydrogenation chemical reaction occurs for dihydromyricetin.
Preferably, it is described to methylbenzenesulfonic acid modification graphene preparation method the following steps are included:
S11. highly oxidized graphene oxide is made by oxidizing process；
S12. the graphene oxide that takes step S11 to obtain and 12h is heated to reflux to methylbenzenesulfonic acid；
S13. the obtained solution of step S12 is filtered；
S14. the obtained filter residue of step S13 is dissolved into the ethanol solution of 60%-70%, evaporation drying of then pressurizeing.
There are oxygen-containing functional group abundant, such as hydroxyl in the graphene oxide obtained using oxidizing process, surface.Graphene oxide
The hydroxyl on surface and the carboxyl on methylbenzenesulfonic acid is reacted, methylbenzenesulfonic acid will be modified in electrode surface.
Preferably, in the step S04, the solution of dihydromyricetin is the Tri-n-Propylamine aqueous solution that pH is 8.0 ~ 8.2.
The generation of dihydromyricetin dehydrogenation reaction is more advantageous under alkaline environment.
Preferably, the electrolysis system in the step S04, is provided with salt bridge between anodic dissolution and cathode solution.
Preferably, the inert electrode is platinum electrode.
The present invention has following technical effect that compared with prior art
A kind of method of dihydromyricetin dehydrogenation carries out modified electrode using the graphene being modified with to methylbenzenesulfonic acid.Using
The method of electrochemistry promotes the generation of dihydromyricetin dehydrogenation reaction.Reaction carries out being more advantageous to dihydromyricetin under alkaline condition
Plain dehydrogenation.The process of entire dihydromyricetin dehydrogenation is with high conversion rate, the fast feature of conversion rate.
Specific embodiment
The present invention can be explained further and illustrate in conjunction with following specific embodiments and comparative example, but specific embodiment is not
There is any type of restriction to the present invention.Test method without specific conditions in lower example embodiment, usually according to this field
Normal condition or the condition suggested according to manufacturer.Those skilled in the art is done any non-on the basis of the present invention
Substantive variation and replacement belongs to scope of the present invention.
Embodiment 1
Dihydromyricetin 2g is taken to carry out dehydrogenation by the following method
A kind of method of dihydromyricetin dehydrogenation, comprising the following steps:
S01. the pre-treatment of electrode；
S02. graphene formic acid benzene methanesulfonic acid modified in the electrode face finish that step S1 is obtained；
S03. the cathode of modified electrode connection power supply step S2 obtained, the anode connection inert electrode of power supply；
S04. it by the electrolysis system of step S3, is put into the solution containing dihydromyricetin；
S05. electrolyte is put into ice domain after static 15h and is filtered.
Further, to methylbenzenesulfonic acid modification graphene preparation method the following steps are included:
S11. highly oxidized graphene oxide is made by oxidizing process；
S12. the graphene oxide that takes step S11 to obtain and 12h is heated to reflux to methylbenzenesulfonic acid；
S13. the obtained solution of step S12 is filtered；
S14. the obtained filter residue of step S13 is dissolved into 70% ethanol solution, evaporation drying of then pressurizeing.
Further, in step S04, the solution of dihydromyricetin is the Tri-n-Propylamine aqueous solution that pH is 8.2.
Further, the electrolysis system in step S04, is provided with salt bridge between anodic dissolution and cathode solution.
Further, inert electrode is platinum electrode.
The conversion ratio for calculating dihydromyricetin is 28.6%.
Embodiment 2
Dihydromyricetin 2g is taken to carry out dehydrogenation by the following method
A kind of method of dihydromyricetin dehydrogenation, comprising the following steps:
S01. the pre-treatment of electrode；
S02. graphene formic acid benzene methanesulfonic acid modified in the electrode face finish that step S1 is obtained；
S03. the cathode of modified electrode connection power supply step S2 obtained, the anode connection inert electrode of power supply；
S04. it by the electrolysis system of step S3, is put into the solution containing dihydromyricetin；
S05. electrolyte is put into ice domain after static 12h and is filtered.
Further, to methylbenzenesulfonic acid modification graphene preparation method the following steps are included:
S11. highly oxidized graphene oxide is made by oxidizing process；
S12. the graphene oxide that takes step S11 to obtain and 12h is heated to reflux to methylbenzenesulfonic acid；
S13. the obtained solution of step S12 is filtered；
S14. the obtained filter residue of step S13 is dissolved into 60% ethanol solution, evaporation drying of then pressurizeing.
Further, in step S04, the solution of dihydromyricetin is the Tri-n-Propylamine aqueous solution that pH is 8.0.
Further, the electrolysis system in step S04, is provided with salt bridge between anodic dissolution and cathode solution.
Further, inert electrode is platinum electrode.
The conversion ratio for calculating dihydromyricetin is 28.4%.
Comparative example 1
Dihydromyricetin 2g is taken to carry out dehydrogenation by the following method
Above-mentioned dihydromyricetin is dissolved in dehydrated alcohol, the sodium pyrosulfate that mass fraction is 20% is added, is reacted at 90 DEG C
5h.The conversion ratio of dihydromyricetin is 20.75%.
Claims (5)
1. a kind of method of dihydromyricetin dehydrogenation, which comprises the following steps:
S01. the pre-treatment of electrode；
S02. graphene formic acid benzene methanesulfonic acid modified in the electrode face finish that step S1 is obtained；
S03. the cathode of modified electrode connection power supply step S2 obtained, the anode connection inert electrode of power supply；
S04. it by the electrolysis system of step S3, is put into the solution containing dihydromyricetin；
S05. electrolyte is put into ice domain after static 12 ~ 15h and is filtered.
2. the method for dihydromyricetin dehydrogenation according to claim 1, which is characterized in that it is described to methylbenzenesulfonic acid modification
The preparation method of graphene the following steps are included:
S11. highly oxidized graphene oxide is made by oxidizing process；
S12. the graphene oxide that takes step S11 to obtain and 12h is heated to reflux to methylbenzenesulfonic acid；
S13. the obtained solution of step S12 is filtered；
S14. the obtained filter residue of step S13 is dissolved into the ethanol solution of 60%-70%, evaporation drying of then pressurizeing.
3. the method for dihydromyricetin dehydrogenation according to claim 1, which is characterized in that in the step S04, dihydromyricetin
The solution of element is the Tri-n-Propylamine aqueous solution that pH is 8.0 ~ 8.2.
4. the method for dihydromyricetin dehydrogenation according to claim 1, which is characterized in that the electrolysis system in the step S04
System, is provided with salt bridge between anodic dissolution and cathode solution.
5. the method for dihydromyricetin dehydrogenation according to claim 1, which is characterized in that the inert electrode is platinum electrode.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112851614A (en) * | 2020-12-28 | 2021-05-28 | 江苏天晟药业股份有限公司 | Preparation method of myricetin |
Citations (5)
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| CN103682105A (en) * | 2013-12-24 | 2014-03-26 | 中国科学技术大学 | Composite anode buffer layer, polymer solar cell and preparation methods of composite anode buffer layer and polymer solar cell |
| CN103871753A (en) * | 2014-02-26 | 2014-06-18 | 江苏昊华精细化工有限公司 | Preparing method of hydrophilic graphene film |
| CN105294630A (en) * | 2015-11-20 | 2016-02-03 | 陕西嘉禾生物科技股份有限公司 | Preparation method of myricetin |
| CN106145100A (en) * | 2016-07-01 | 2016-11-23 | 国家地质实验测试中心 | The preparation method of sulfonated graphene and the method for detection heavy metal ion thereof |
| CN108586409A (en) * | 2018-04-12 | 2018-09-28 | 铜仁学院 | A kind of preparation method being converted into myricetin with efficient dihydromyricetin |
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2018
- 2018-09-05 CN CN201811032759.2A patent/CN109267088A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103682105A (en) * | 2013-12-24 | 2014-03-26 | 中国科学技术大学 | Composite anode buffer layer, polymer solar cell and preparation methods of composite anode buffer layer and polymer solar cell |
| CN103871753A (en) * | 2014-02-26 | 2014-06-18 | 江苏昊华精细化工有限公司 | Preparing method of hydrophilic graphene film |
| CN105294630A (en) * | 2015-11-20 | 2016-02-03 | 陕西嘉禾生物科技股份有限公司 | Preparation method of myricetin |
| CN106145100A (en) * | 2016-07-01 | 2016-11-23 | 国家地质实验测试中心 | The preparation method of sulfonated graphene and the method for detection heavy metal ion thereof |
| CN108586409A (en) * | 2018-04-12 | 2018-09-28 | 铜仁学院 | A kind of preparation method being converted into myricetin with efficient dihydromyricetin |
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| ZIVKO SANICANIN: ""Electrochemical syntheis of heterocyclic compounds-XVII.anodic oxidation of 2"-hydroxychalocones"", 《ELECTROCHIMICA ACTA》 * |
| 鲁宽科等: ""黄烷酮电解氧化合成黄酮"", 《兰州大学学报（自然科学版）》 * |
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| CN112851614A (en) * | 2020-12-28 | 2021-05-28 | 江苏天晟药业股份有限公司 | Preparation method of myricetin |
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