CN107602531A - A kind of 2 iodosobenzoic acid solution and its preparation method and application - Google Patents
A kind of 2 iodosobenzoic acid solution and its preparation method and application Download PDFInfo
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- CN107602531A CN107602531A CN201710805338.8A CN201710805338A CN107602531A CN 107602531 A CN107602531 A CN 107602531A CN 201710805338 A CN201710805338 A CN 201710805338A CN 107602531 A CN107602531 A CN 107602531A
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Abstract
This application discloses a kind of 2 iodosobenzoic acid solution and its preparation method and application.The 2 iodosobenzoic acid solution of the application, wherein containing solute, solvent and cosolvent, solute is 2 iodosobenzoic acids, and solvent is acetonitrile, and cosolvent is BFEE.The 2 iodosobenzoic acid solution of the application, in the case where BFEE is as cosolvent, can make 2 iodosobenzoic acids be dissolved in conventional organic solvent acetonitrile；As oxidant in use, alcohol can be efficiently oxidized into aldehydes or ketones at room temperature, the oxidation activity of 2 iodosobenzoic acids is considerably improved, saves the reaction time, improves production efficiency；And the difficulty of experiment post processing is reduced, laid a good foundation for the popularization and application of 2 iodosobenzoic acids.
Description
Technical field
The application is related to high price means of iodine chemical reagent field, more particularly to a kind of 2- iodosobenzoic acids solution and its preparation
Methods and applications.
Background technology
2- iodosobenzoic acids are typical hypervalent iodine reagents, and oxidant is used as in organic synthesis, can aoxidize alcohol
For aldehydes or ketones, referred to as IBX.IBX is found in 1893, C.Hartmann, V.Meyer by Hartman and Mayer,
Eur.J.Inorg.Chem.1893,26,1727-1732..Due to intermolecular strong interaction in lattice, people sent out at that time
Existing IBX is practically insoluble in any commonly employed organic solvent.1994, Frigerio and Santagostino had found that IBX can dissolve
In solvent dimethyl sulfoxide (DMSO) (abbreviation DMSO), and find that alcohol can be oxidized to aldehydes or ketones by IBX, M.Frigerio,
M.Santagostino,Tetrahedron 1994,35,8019-8022.., can be by the oxygen of alcohol because IBX reaction conditions are gentle
Change the stage for resting on aldehyde, and functional group compatibility is high, other functional groups will not be impacted, so IBX extensive uses
In organic synthesis.
Reaction equation one
As shown in reaction equation one, in DMSO solvents, IBX can react with alcohol 1, generate aldehydes or ketones 2 corresponding to alcohol 1.Due to
Intermolecular strong interaction in IBX lattices, in addition to DMSO, it is other not find that IBX can be dissolved at normal temperatures so far
Organic solvent.The reaction of IBX oxidation alcohol generally requires to be heated to reflux in other solvents, and IBX has blast at high temperature
Danger, it greatly limit its application.On the other hand, DMSO solvent boiling points are very high, it is difficult to removed with conventional roto-vap operation,
Very big trouble is caused to experiment post processing, it is not only time-consuming, it can also use substantial amounts of solvent extraction, waste of resource.Moreover,
Reactivities of the IBX in DMSO is not very high, if IBX reactivities can be improved, to saving the reaction time, improves efficiency meeting
Have very great help.
The content of the invention
The purpose of the application is to provide a kind of new 2- iodosobenzoic acid solution and its preparation method and application.
The application employs following technical scheme：
The one side of the application discloses a kind of 2- iodosobenzoic acids solution, and solute, solvent are contained in the solution and is helped
Solvent, wherein, solute is 2- iodosobenzoic acids, and solvent is acetonitrile, and cosolvent is BFEE.
It should be noted that the application's it is critical that by adding BFEE so that IBX can be dissolved in second
Nitrile, so as to obtain the 2- iodosobenzoic acid solution of the application.For the DMSO solution of 2- iodosobenzoic acids, this Shen
2- iodosobenzoic acid solution please, as alcohol oxidant in use, its activity is higher；In a kind of implementation of the application,
Under same concentrations, same amount and the same terms, the 2- iodosobenzoic acids solution of the application is in 4 minutes by phenmethylol oxygen
The yield for turning to benzaldehyde just reaches 88%, and benzyl alcohol oxidation is by the DMSO solution of 2- iodosobenzoic acids two hours or so
The yield of benzaldehyde is only about 70%.In addition, the 2- iodosobenzoic acids solution of the application using acetonitrile as solvent, and acetonitrile
It is low boiling point solvent, only about 82 DEG C of boiling point, therefore, easily removes, reduce experiment post-processing difficulty, is IBX popularization and application
Lay a good foundation.Also, the 2- iodosobenzoic acids solution of the application is prepared simply, due to adding for cosolvent BFEE
Add so that IBX can be dissolved in lower boiling conventional organic solvent acetonitrile at normal temperatures, and preparation technology is simple to operation.
It should be added that after organic reaction, generally use rotary evaporation obtains crude product except solvent, then carries out
Silica gel column chromatography separates, then rotary evaporation obtains target product.And the 2- iodosobenzoic acid solution of the application is used as oxygen
Agent, can directly carry out silica gel column chromatography separation after reaction, rotary evaporation removes solvent, obtains target product.Wherein, cosolvent
The boron trifluoride molecule of BFEE is attracted on silica gel, and ether molecule rotary evaporation removes.Due to acetonitrile low boiling point,
Ether is volatile, therefore, greatly reduces experiment post-processing difficulty.
Preferably, the dosage of cosolvent is more than or equal to the solute of 1 equivalent.
It should be noted that the solute that the dosage of cosolvent is more than or equal to 1 equivalent refers to that the amount of the material of cosolvent is
At least one times of solute.Under normal circumstances, when no cosolvent adds, IBX is insoluble in acetonitrile, and adds cosolvent,
Realize IBX and be dissolved in acetonitrile at normal temperatures so that IBX has widely application.It is appreciated that the addition of cosolvent is direct
The amount that IBX is dissolved in acetonitrile is influenceed, finally, influences the concentration of 2- iodosobenzoic acids in 2- iodosobenzoic acid solution；For etc.
For the acetonitrile of amount, cosolvent addition is higher, and the solubility of 2- iodosobenzoic acids in the solution is higher.
The another side of the application discloses application of the 2- iodosobenzoic acids solution of the application in alcohol oxidation.
The another side of the application discloses application of the 2- iodosobenzoic acid solution of the application in oxidant.
It should be noted that the key of the application is by adding cosolvent so that IBX can be dissolved in acetonitrile, solve
When DMSO is as solvent, experiment post-processing difficulty is big, it is time-consuming, take the problems such as resource.It is appreciated that utilizing 2- iodoxy benzene
After the DMSO solution of formic acid aoxidizes to alcohol, when extracting its product, or DMSO is evaporated, produced or being extracted with extractant
Thing；The former is because DMSO boiling points are higher about 189 DEG C, it is difficult to rotary evaporation, and IBX has explosion danger under high temperature, therefore, it is difficult to reality
It is existing；The latter is not only time-consuming, and extraction needs to expend a large amount of solvents.And the 2- iodosobenzoic acid solution of the application, with acetonitrile
As solvent, the boiling point of acetonitrile is very low, very easily can be removed solvent by the way of rotary evaporation, therefore reduce reality
Test the difficulty of post processing.Therefore, the applicable field of the DMSO solution of 2- iodosobenzoic acids or 2- iodosobenzoic acids institute is all
The 2- iodosobenzoic acid solution of the application can be used, includes but are not limited to alcohol oxidation.The 2- iodoxy benzene first of the application
Acid solution, various aromatic alcohols are preferably particularly to alcohol, and phenyl ring connection substitution class alcohol has the oxidation effectiveness of more efficient.
The preparation method of the 2- iodosobenzoic acid solution for simultaneously also disclosing the application again of the application, including by solute
2- iodosobenzoic acids and cosolvent are added in solvent acetonitrile, are mixed at room temperature using ultrasonic wave, are made 2- iodosobenzoic acids
Acetonitrile is dissolved in, 2- iodosobenzoic acid solution is made；Wherein, cosolvent is BFEE.
It should be noted that the application's by adding cosolvent it is critical that enable 2- iodosobenzoic acids in room
Acetonitrile is dissolved under temperature, wherein, room temperature refers to the normal temperature of 25 left and right, i.e., the normal room temperature that need not additionally heat.Ultrasonic wave mixes
The time of conjunction, it is completely dissolved and is defined by 2- iodosobenzoic acids, generally in 5-20 minutes, the equivalent of cosolvent is higher, dissolving
Time is shorter.
The application's simultaneously also discloses a kind of mixed solvent for 2- iodosobenzoic acids again, and the mixed solvent includes
Main solvent acetonitrile and cosolvent, wherein, cosolvent is BFEE.
It should be noted that the key of the application is to allow 2- iodosobenzoic acids to be dissolved in low boiling by cosolvent
Conventional organic solvent acetonitrile, reduce the experiment post-processing difficulties of 2- iodosobenzoic acid oxidants, i.e., compared to DMSO, second
Nitrile is easier to remove, therefore so that 2- iodosobenzoic acids can widely be applied to each field.It is appreciated that because 2-
Iodosobenzoic acid is practically insoluble in any organic solvent in addition to DMSO, which greatly limits its application, and the application
Mixed solvent, due to added with cosolvent, alloing 2- iodosobenzoic acids to be dissolved in acetonitrile, it is difficult to not only reduce experiment post processing
Degree, and also improves the activity of 2- iodosobenzoic acids, therefore, compared to DMSO, the mixed solvent of the application be it is a kind of more
It is suitable for the solvent of 2- iodosobenzoic acids.
It is appreciated that for the acetonitrile of equivalent, the amount of cosolvent is higher, the 2- iodoxies that mixed solvent can dissolve
Benzoic acid amount is more, and therefore, the in the mixed solvent of the application does not limit the amount of cosolvent specifically；In general, the amount of cosolvent
More than the amount of the material of dissolved 2- iodosobenzoic acids.
A kind of 2- iodosobenzoic acids for simultaneously also disclosing chemical modification again of the application, the 2- iodoxies of the chemical modification
Yl benzoic acid is the complex that boron trifluoride and 2- iodosobenzoic acids form, wherein, boron trifluoride molecule and 2- iodoxies
The oxygen atom of carbonyl in yl benzoic acid molecule forms coordinate bond, forms complex.
It should be noted that the application research is found, BFEE can make 2- iodosobenzoic acids be dissolved in acetonitrile,
It destroys intermolecular I-O in IBX lattices it is critical that boron trifluoride molecule and IBX carbonylic oxygen atom formation coordinate bond
Key, so that IBX can be dissolved in acetonitrile.That is, the 2- iodosobenzoic acids of modification are coordinated by boron trifluoride, not only
DMSO can be dissolved in, but also conventional organic solvent acetonitrile can be dissolved in, therefore, than the 2- iodoxy benzene of no chemical modification
Formic acid has wider purposes.Because boron trifluoride molecule electron-withdrawing power is strong, the electronics of oxidation center iodine atom is reduced
Density, IBX oxidisability is improved, therefore, boron trifluoride coordination modification will not only weaken IBX activity, can carry on the contrary
Its high oxidisability.In a kind of implementation of the application, the 2- iodosobenzoic acids of chemical modification are dissolved in acetonitrile, as oxidation
Agent, its oxidation yield to phenmethylol just reaches 88% in 4 minutes, without the DMSO solution of the 2- iodosobenzoic acids of modification
The yield of two hours is only about 70%.
It should be added that increase the principle of IBX oxidisability according to BFEE, in IBX DMSO solution
Middle addition BFEE, can equally strengthen oxidisability；But the application research is found, because the S atom in DMSO is matched somebody with somebody
Capability is very strong, causes boron trifluoride preferential and DMSO is coordinated, only when BFEE high amount, can just there is part three
Boron fluoride molecule and IBX coordinations, strengthen IBX oxidisability, experiment display, it is necessary to add 160 equivalents in IBX DMSO solution
BFEE, reaction rate about improves 5 times, and effect can not show a candle to add the IBX acetonitrile solutions of BFEE.And
And BFEE, as cosolvent, its addition is excessive, is had little significance for organic synthesis.
The application's simultaneously also discloses the application of acetonitrile and BFEE as 2- iodosobenzoic acid solvents again.
The beneficial effect of the application is：
The 2- iodosobenzoic acid solution of the application, in the case where BFEE is as cosolvent, using acetonitrile as
Solvent, alcohol can be efficiently oxidized to aldehydes or ketones at room temperature.The 2- iodosobenzoic acids solution as oxidant in use,
The oxidation activity of 2- iodosobenzoic acids is considerably improved, saves the reaction time, improves production efficiency；And reduce
The difficulty of post processing is tested, is laid a good foundation for the popularization and application of 2- iodosobenzoic acids.
Brief description of the drawings
Fig. 1 is the yield figure that benzyl alcohol oxidation is benzaldehyde in the embodiment of the present application, wherein, ▲ curve is the 2- of the application
Iodosobenzoic acid solution changes over time curve as oxidation yield of the oxidant to phenmethylol, ● curve is 2- iodoxy benzene
For the DMSO solution of formic acid as oxidation curve of the oxidant to phenmethylol, ■ curves are that 2- iodosobenzoic acids are not adding trifluoro
The solution obtained during acetonitrile is directly dissolved in as oxidation curve of the oxidant to phenmethylol when changing borate ether.
Embodiment
2- iodosobenzoic acids are used as oxidant in organic synthesis, and still, 2- iodosobenzoic acids are except being dissolved in
Beyond DMSO, any commonly employed organic solvent is practically insoluble in.And the DMSO solution of 2- iodosobenzoic acids makes as oxidant
Used time, the problems such as experiment post-processing difficulty height, complex process be present.Therefore, if 2- iodosobenzoic acids can be dissolved in it is conventional
Organic solvent, then can largely be beneficial to popularization and application of the 2- iodosobenzoic acids as oxidant.
The application has found that 2- iodosobenzoic acids, can in the case where adding cosolvent by lot of experiments and research
It is dissolved in acetonitrile.And acetonitrile is conventional low boiling point solvent, this greatly reduces the difficulty that experiment post processing removes solvent.Not only such as
This, 2- iodosobenzoic acids and cosolvent are dissolved in acetonitrile and higher oxidation activity are also obtained, and can greatly shorten the reaction time,
Improve production efficiency.In a kind of implementation of the application, using BFEE as cosolvent, by 2- iodoxy benzene first
Acid is dissolved in acetonitrile, obtains 2- iodosobenzoic acid solution, uses the solution to benzyl alcohol oxidation for benzaldehyde, in 4 minutes
Yield is just up to 88%；And the corresponding solution that 2- iodosobenzoic acids are directly dissolved in DMSO, the yield of two hours is just only about
70%.It can be seen that the 2- iodosobenzoic acid solution oxide activity of the application greatly improves, the reaction time is shortened, improves life
Produce efficiency.
Some professional terms is explained as follows in the application：
2- iodosobenzoic acids：Typical hypervalent iodine reagent, is used as oxidant in organic synthesis, can be oxidized to alcohol
Aldehydes or ketones, referred to as IBX；The reagent C used in the embodiment of the present application AS is entered for 61717-82-6 2- iodosobenzoic acids
Row experiment.
Oxidant：In redox reaction, the material for obtaining electronics is referred to as oxidant, correspondingly, loses electronics
Material is referred to as reducing agent.Oxidant has oxidisability, obtains the reduction of electronics chemical valence, reduction reaction occurs, obtains reduzate.
Dimethyl sulfoxide (DMSO)：A kind of organic compounds containing sulfur, molecular formula are (CH3)2SO, it is the transparent of no color or smell under normal temperature
Liquid, is a kind of hygroscopic flammable liquid, abbreviation DMSO.With highly polar, higher boiling, heat endurance is good, non-proton and water
Miscible characteristic, 189 degrees Celsius of boiling point, most of organic matters such as ethanol, propyl alcohol, benzene and chloroform can be dissolved in, be commonly used for organic anti-
Answer solvent.
Acetonitrile：Alias methyl cyanide, cyanogen methane, molecular formula CH3CN；For colourless liquid, 82 degree of boiling point, water and alcohol can be dissolved in,
It is commonly used for organic solvent.
The application is described in further detail below by specific embodiment.Following examples only are entered to advance to the application
One step illustrates, should not be construed as the limitation to the application.
Embodiment
This example carries out nuclear-magnetism experiment first in nuclear magnetic tube using a small amount of oxidant, and more different oxidants are by phenmethylol
It is oxidized to the speed of benzaldehyde；Reaction product does not separate, and directly calculates yield by nuclear magnetic spectrogram.It is determined that BFEE
After effect, then the amplification test of the conventional Small Amount in laboratory is carried out, amplification test is separated, purified, weighing after completing, nuclear-magnetism
After spectrogram confirms that product is correct, yield is calculated according to weighing.
Wherein, different oxidants refer to used by this example：(1) this example added with BFEE and be dissolved in acetonitrile
IBX solution；(2) as a comparison, IBX is directly dissolved in DMSO, the IBX of acquisition DMSO solution；(3) as a comparison,
BFEE is not added, IBX is directly dissolved in acetonitrile, the IBX comparative solutions of acquisition.Experiment process in detail is as follows：
First, nuclear-magnetism is tested
It is as follows that this example carries out each oxidant of nuclear-magnetism experiment and preparation method thereof：
IBX solution：BFEE is added into IBX, then adds appropriate acetonitrile solvent, after ultrasonic about 10 minutes,
Obtain the IBX solution of this example.When nuclear-magnetism is tested, 1.4mg IBX, 2.8mg boron trifluoride second are specifically added in nuclear magnetic tube
The acetonitrile of ether and 0.5mL, reacted with 0.54mg phenmethylol.
IBX DMSO solution：1.4mg IBX, 0.5mL DMSO are added in nuclear magnetic tube, is entered with 0.54mg phenmethylol
Row reaction.
IBX comparative solutions：1.4mg IBX, 0.5mL acetonitrile are added in nuclear magnetic tube, is carried out with 0.54mg phenmethylol
Reaction.
Nuclear-magnetism tests obtained yield figure result as shown in figure 1, wherein, ▲ curve is the IBX solution oxide products of this example
Yield change over time curve, ● curve changes over time for the yield of the DMSO solution oxidation product of IBX as a comparison
Curve, ■ curves change over time curve for the yield of IBX comparative solution oxidation products as a comparison.
Fig. 1 result shows that for IBX solution in 4min, the yield of benzaldehyde has reached 88%, as in Fig. 1 ▲ curve
Shown, when reacting 45min, yield is up to 95%, consequently reaches reaction balance, and benzaldehyde yield maintains about 95%；
IBX DMSO solution is in reaction 102min, benzaldehyde yield only about 66%, in Fig. 1 ● shown in curve；And IBX comparative solutions,
Because IBX not dissolved in acetonitrile, the benzaldehyde yield of two hours is only about 15%, as shown in ■ curves in Fig. 1.It can be seen that trifluoro
Changing borate ether can not only make IBX be dissolved in acetonitrile, and can also improve IBX oxidation activity, greatly speed up IBX Oxybenzene methyl alcohols
Reaction rate.
2nd, scale-up
This example is exaggerated experiment to IBX solution, specific as follows：
IBX solution：IBX 134.4mg, BFEE 170.3mg are weighed, both are added in 2.0mL acetonitriles, is surpassed
After sound about 10 minutes, visually observe IBX and be completely dissolved in acetonitrile, that is, obtain the IBX solution of this example.
43.3mg phenmethylols are taken to be mixed with 2mL oxidizing agent solutions, room temperature under stirring condition without being aoxidized in 5mL flasks
Reaction.The reaction equation of oxidation reaction is as follows：
Reaction is separated after completing using silica gel column chromatography, and then rotary evaporation removes solvent and obtains benzaldehyde product.Adopt
Use 500MHz1H NMR nucleus magnetic hydrogen spectrums identify benzaldehyde product.And using the yield of balance measurement benzaldehyde, the yield of benzaldehyde
According to formula：[(108 × m) ÷ (106 × 43.3)] × 100% calculates, and wherein m is the weight of the benzaldehyde product weighed, single
Position is mg.
Using1The result of H NMR nucleus magnetic hydrogen spectrums identification shows that its oxidation product is benzaldehyde.Using balance measurement benzene first
The yield of aldehyde, and by the oxidation product of yield formula calculating IBX solution, as a result show, separation, title after reaction in three minutes terminates
Benzaldehyde 40.3mg is restored, yield is up to 95%.
Result above shows the kinetic curve that the oxidisability of IBX solution monitors in real time after extensive magnitude with nuclear-magnetism test
Substantially it is consistent.It can be seen that BFEE can not only make IBX be dissolved in acetonitrile, and IBX oxidation activity can also be improved, greatly
The reaction rate of fast IBX Oxybenzene methyl alcohols.
On the basis of being tested more than, this example has further carried out oxidation test to different alcohol, as a result shows, except benzene
Beyond methanol can be oxidized, 1- benzyl carbinols, p nitrobenzyl alcohol and cinnamyl alcohol can be by the quick oxygen of IBX solution of this example
Change.Wherein, phenmethylol and 1- benzyl carbinols are all the representatives of aromatic alcohol, and phenmethylol is the representative of primary alconol, and 1- benzyl carbinols are secondary alcohol
Represent；P nitrobenzyl alcohol is the representative of phenyl ring connect substituent；Therefore, it can confirm that the IBX solution of this example can be to fragrance
Alcohol, phenyl ring connection substitution class alcohol carry out Quick Oxidation.
In addition, this example is further right, BFEE makes IBX be dissolved in acetonitrile, and the principle for improving its oxidation activity is entered
Go and furtherd investigate and analyze, as a result found, the addition of BFEE, made boron trifluoride molecule and IBX ketonic oxygen former
Son forms coordinate bond, intermolecular I-O keys in IBX lattices is destroyed, so that IBX can be dissolved in acetonitrile.It is also, borontrifluoride
Electron-withdrawing power of boron molecule itself is strong, reduces the electron density of oxidation center iodine atom, this improves IBX oxidisability,
The energy barrier that rate determining step reduction eliminates is reduced, so as to improve reaction rate.
Speculated according to principles above, the examination of the lewis acid reagent of other electron deficients or the electron deficient with coordination property
Agent also can make IBX be dissolved in acetonitrile, and improve IBX oxidisability, numerous to list herein.
Above content is to combine the further description that specific embodiment is made to the application, it is impossible to assert this Shen
Specific implementation please is confined to these explanations.For the application person of an ordinary skill in the technical field, do not taking off
On the premise of conceiving from the application, some simple deduction or replace can also be made, should all be considered as belonging to the protection of the application
Scope.
Claims (8)
- A kind of 1. 2- iodosobenzoic acids solution, it is characterised in that：Contain solute, solvent and cosolvent in the solution, it is described Solute is 2- iodosobenzoic acids, and the solvent is acetonitrile, and the cosolvent is BFEE.
- 2. 2- iodosobenzoic acids solution according to claim 1, it is characterised in that：The dosage of the cosolvent be more than or Equal to the solute of 1 equivalent.
- 3. application of the 2- iodosobenzoic acids solution according to claim 1 or 2 in alcohol oxidation.
- 4. application of the 2- iodosobenzoic acids solution according to claim 1 or 2 in oxidant.
- 5. the preparation method of 2- iodosobenzoic acids solution according to claim 1 or 2, it is characterised in that：Including will be molten Matter 2- iodosobenzoic acids and cosolvent are added in solvent acetonitrile, are mixed at room temperature using ultrasonic wave, are made 2- iodoxy benzene first Acid is dissolved in acetonitrile, and the 2- iodosobenzoic acids solution is made；The cosolvent is BFEE.
- A kind of 6. mixed solvent for 2- iodosobenzoic acids, it is characterised in that：The mixed solvent includes main solvent acetonitrile And cosolvent, the cosolvent are BFEE.
- A kind of 7. 2- iodosobenzoic acids of chemical modification, it is characterised in that：The 2- iodosobenzoic acids of the chemical modification are The complex of boron trifluoride and 2- iodosobenzoic acids composition, wherein, boron trifluoride molecule and 2- iodosobenzoic acids point The oxygen atom of carbonyl in son forms coordinate bond, forms the complex.
- 8. the application of acetonitrile and BFEE as 2- iodosobenzoic acid solvents.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072166A (en) * | 2021-03-25 | 2021-07-06 | 北京建筑大学 | Oxidation treatment method for smelly substances in water |
| CN111116333B (en) * | 2019-12-27 | 2023-10-20 | 泛亚（武汉）食品科技有限公司 | High-molecular-load oxidant containing iodine with high valence, preparation method and application |
-
2017
- 2017-09-08 CN CN201710805338.8A patent/CN107602531B/en active Active
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| DAIZE MO ET AL.: "Facile electrochemical polymerization of 2-(thiophen-2-yl)furan and the enhanced capacitance properties of its polymer in acetonitrile electrolyte containing boron trifluoride diethyl etherate", 《ELECTROCHIMICA ACTA》 * |
| HACER DOLAS ET AL.: "An impedance-morphology study on poly(3-methylthiophene) coated electrode obtained in boron trifluoride diethyl etherate-acetonitrile", 《SYNTHETIC METALS》 * |
| JINGKUN XU ET AL.: "Low potential electrochemical polymerization of 3-chlorothiophene in mixed electrolytes of boron trifluoride diethyl etherate and trifluoroacetic acid", 《JOURNAL OF ELECTROANALYTICAL CHEMISTRY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111116333B (en) * | 2019-12-27 | 2023-10-20 | 泛亚（武汉）食品科技有限公司 | High-molecular-load oxidant containing iodine with high valence, preparation method and application |
| CN113072166A (en) * | 2021-03-25 | 2021-07-06 | 北京建筑大学 | Oxidation treatment method for smelly substances in water |
| CN113072166B (en) * | 2021-03-25 | 2022-03-01 | 北京建筑大学 | Oxidation treatment method for smelly substances in water |
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