CN108373147A - A kind of preparation method and applications of alkynyl carbon material - Google Patents
A kind of preparation method and applications of alkynyl carbon material Download PDFInfo
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- CN108373147A CN108373147A CN201810047016.6A CN201810047016A CN108373147A CN 108373147 A CN108373147 A CN 108373147A CN 201810047016 A CN201810047016 A CN 201810047016A CN 108373147 A CN108373147 A CN 108373147A
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- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
- H01M4/583—Carbonaceous material, e.g. graphite-intercalation compounds or CFx
- H01M4/587—Carbonaceous material, e.g. graphite-intercalation compounds or CFx for inserting or intercalating light metals
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
The present invention relates to a kind of preparation method and applications of alkynyl carbon material, and the carbon material is one alkynes powder of class graphite, by phenyl-hexahalide（C6X6）, calcium carbide（CaC2）It is placed in vacuum ball grinder with ball milling pearl, absolute ethyl alcohol is added；Ball grinder is sealed, inert gas is vacuumized or be passed through to ball grinder；The molar ratio of phenyl-hexahalide and calcium carbide is 1:6~1:18；By planetary ball mill with 400 ~ 600 revs/min of rate ball milling 6 ~ 18 hours；Washing is dried, and washing, drying is to get to one alkynes powder of class graphite.Preparation method of the present invention simplifies technological process.The present invention relates to preparation methods compared with existing cross-coupling reaction, and it is simple to simplify required equipment, is suitable for industrialized production.
Description
Technical field
The invention belongs to carbon material fields, and in particular to a kind of preparation method and applications of alkynyl carbon material.
Background technology
Graphite alkene material is after graphene, another is known as the new carbon of super material, because its is unique
Electric property and electrochemical properties, and gather around and have wide practical use in fields such as the energy, electronics, catalysis.Ideal graphite alkene
It is to be connected phenyl ring by several acetylene bonds, is formed by sp2Hydbridized carbon atoms and sp3The two dimensional surface net that hybridized atom conjugation is constituted
The carbon material of network structure.
2010, the good academician seminars of Chinese Academy of Sciences Li Yu passed through Glaser-Hay cross-coupling reactions synthetic graphite two for the first time
Alkynes（Graphdiyne types）, then caused the upsurge of graphite alkene research.On this basis, the projects such as Liu Zhongfan, Sakamoto
Group has further developed the technologies such as graphite alkene nm wall array, graphite alkene nanobelt, has pushed the research of graphite alkene.Currently,
Graphite diine realizes excellent property in application aspects such as lithium ion battery, sodium-ion battery, fuel cell, ultracapacitors
Energy.However, it is existing by Cu catalysis or high-temperature catalytic Glaser-Hay cross-coupling reaction synthetic graphite diines technique
It needs to use six alkynyl benzene (hexaethynylbenzene) of presoma, which cannot achieve industrialization, limit at present
The popularization of the technique.
The present invention proposes that one kind using phenyl-hexahalide and calcium carbide as raw material, passing through one alkynes of mechanochemical reaction synthetic graphite
（Graphyne types）New method.By the mechanical ball mill of planetary ball mill, directly obtained at normal temperatures containing one alkynes of graphite
Powder, remove impurity by washing, obtain one alkynes of pure graphite, pass through the connection of 1 acetylene bond between the phenyl ring of one alkynes of graphite.Phase
Than in existing method, this method simplifies synthesis procedure, and device requirement is low.
Invention content
The purpose of the present invention is to provide a kind of process is simple, a kind of preparation method of the low alkynyl carbon material of device requirement
And its application.
A kind of preparation method of alkynyl carbon material provided by the invention, the carbon material are one alkynes powder of class graphite, specifically
Steps are as follows：
（1）By phenyl-hexahalide（C6X6）, calcium carbide（CaC2）It is placed in vacuum ball grinder with ball milling pearl, absolute ethyl alcohol is added；Ball sealer
Grinding jar vacuumizes ball grinder or is passed through inert gas；The molar ratio of phenyl-hexahalide and calcium carbide is 1:6~1:18；
（2）By planetary ball mill with 400 ~ 600 revs/min of rate ball milling 6 ~ 18 hours；
（3）Take out step（2）The unreacted calcium carbide of removal is washed with deionized in the sample that ball milling is completed；
（4）By step（3）Obtained product is dried with 40 ~ 90 DEG C, and is pulverized；
（5）By step（4）Obtained product washing, removes unreacted phenyl-hexahalide；
（6）By step（5）Obtained product is with 40 ~ 90 DEG C of drying to get to one alkynes powder of graphite.
In the present invention, phenyl-hexahalide can be any in hexachloro-benzene, hexabromobenzene or hexaiodo benzene.
In the present invention, the control of ball material mass ratio is 20:1~100:1.
In the present invention, the amount of absolute ethyl alcohol need to not there be ball milling pearl at least.
In the present invention, the inert atmosphere is nitrogen（N2）Or argon gas（Ar）.
The one alkynes power applications of graphite obtained using preparation method of the present invention are in catalysis material, electrochemistry or lithium-ion electric
Pond negative material.
Experiment shows that one alkynes material of class graphite prepared by the present invention is a kind of p-type semiconductor, can be applied to electrochemistry
Field.
Experiment shows that one alkynes material of graphite prepared by the present invention has good Photocatalytic activity, can be applied to
Photocatalysis degradation organic contaminant.
Experiment shows that one alkynes material of graphite prepared by the present invention has certain storage lithium activity, can be applied to lithium ion battery
Negative material.
Graphite alkene is a kind of new carbon newly proposed in recent years, is possessed widely in fields such as the energy, electronics, catalysis
Application prospect.Currently, the preparation method of graphite alkene is only by handing over cross-coupling reaction to prepare graphite diine one kind, presoma
Preparation difficulty is big, and sample yield is relatively low.Therefore, one alkynes material of graphite is prepared by the big preparation method of this amount of mechanochemical reaction
There is good foreground at two aspect of preparation and application of graphite alkene.
Compared with prior art, the present invention has following outstanding feature：
（1）The present invention is prepared for a kind of novel graphite alkynes material（One alkynes of graphite）
（2）The present invention relates to preparation methods compared with existing cross-coupling reaction, simplifies technological process.
（3）The present invention relates to preparation methods compared with existing cross-coupling reaction, and it is simple to simplify required equipment, is suitble to
In industrialized production.
Present invention substantive distinguishing features outstanding and marked improvement can be emerged from from following embodiment, but are not limited to
This.
Description of the drawings
Fig. 1 is the one alkynes powder preparing processes schematic diagram of graphite in embodiment 1.
Fig. 2 is the full spectrum of the x-ray photoelectron spectroscopy of the one alkynes powder of graphite in embodiment 1.
Fig. 3 is the carbon spectrum of the x-ray photoelectron spectroscopy of the one alkynes powder of graphite in embodiment 1.
Fig. 4 is the Raman pattern of the one alkynes powder of graphite in embodiment 1.
Fig. 5 is the photo-catalytic degradation of methyl-orange curve graph of the one alkynes sample of graphite in embodiment 1
Fig. 6 is the diffusing reflection absorption spectrum of the one alkynes powder of graphite in embodiment 2.
Fig. 7 is the linear sweep voltammetry spectrum of the one alkynes electrode of graphite in embodiment 2.
Fig. 8 is the not special Schottky curve of the one alkynes electrode of graphite in embodiment 2.
Fig. 9 is the energy band diagram of the one alkynes sample of graphite in embodiment 2.
Figure 10 is applied to cycle performance curve when negative electrode of lithium ion battery for the one alkynes sample of graphite in embodiment 3, fills
Discharge current density is 100 milliamperes/gram, ranging from 0.01 ~ 3.0 volt of charging/discharging voltage.
Specific implementation mode
The specific implementation of the present invention is described further below in conjunction with example and attached drawing, but the implementation and protection of the present invention
It is without being limited thereto.
Embodiment 1
With 1:20 ball material mass ratio, according to 1:6 molar ratio weighs hexachloro-benzene（C6Cl6）And calcium carbide（CaC2）, it is placed in ball milling
In tank, absolute ethyl alcohol is added to no mistake abrasive material.Seal ball grinder.Pass through planetary ball mill ball milling with 400 revs/min of rate
18 hours.The sample that ball milling is completed is taken out, makes that the unreacted calcium carbide of removal is washed with deionized.Hot benzene is reused after drying
Washing removes unreacted phenyl-hexahalide, directly obtains one alkynes powder of graphite.
Measure 50 milliliters of methyl orange solutions（10 mg/litres）, be added 50 milligrams of samples, stand 3 hours after, with it is ultraviolet-can
Light-exposed irradiation carries out photocatalytic degradation reaction.Every 20 minutes, the absorbance of solution is measured using UV-vis absorption spectrum
Variation.
The full spectrum of the x-ray photoelectron spectroscopy of sample（Fig. 2）Illustrate, the oxygen element that sample is brought into addition to surface contamination
Outside, it is only made of carbon.The carbon of the x-ray photoelectron spectroscopy of sample is composed（Fig. 3）With Raman pattern（Fig. 4）Illustrate in sample
Carbon only exists sp2Hydridization and sp3Hydridization two states, in conjunction with Fig. 2, it is thus identified that sample is one alkynes of graphite.Sample is ultraviolet again can
Light-exposed lower photo-catalytic degradation of methyl-orange curve（Fig. 5）Illustrate that one alkynes sample of graphite has photocatalysis degradation organic contaminant performance.
Embodiment 2
With 1:50 ball material mass ratio, according to 1:12 molar ratio weighs hexabromobenzene（C6Br6）And calcium carbide（CaC2）, it is placed in true
In empty ball grinder, absolute ethyl alcohol is added to no mistake abrasive material.Ball grinder is sealed, to being passed through nitrogen after ball grinder（N2）.With 500 turns/
Minute rate pass through planetary ball mill ball milling 12 hours.
After the sample completed to ball milling according to 1 the method for example is washed and dried, by sample and polyethylene glycol, ethyl
Cellulose, ethyl alcohol are according to mass ratio：9：9：1：1 mixing, magnetic agitation 2 ~ 10 hours at 40 ~ 90 DEG C.Obtained slurry is revolved
Be applied on electro-conductive glass, after drying in Muffle furnace with 260 ~ 300 DEG C under conditions of anneal, remove polyethylene glycol, ethyl cellulose
The surfactants such as element.Using conducting wire, conducting resinl, insulating cement etc. by the electrode package after annealing to get electric to the work of sample
Pole.
The diffusing reflection absorption spectrum of sample（Fig. 6）It is middle to there is absorption band edge, illustrate that sample is semiconductor, 2.2 electronics of band gap
Volt.The linear sweep voltammetry of sample electrode is composed as shown in fig. 7, relative to -0.5 volt to -1.2 volts of saturated calomel electrode
There is an electric current platform in place, which is to be influenced can be ignored by electric field due to minority carrier, only is influenced to make by diffusion
At；The electric current is that negative current illustrates that the sample is p-type semiconductor.Relative to -0.7 volt of saturated calomel electrode to -0.4
Volt place occur a zero current platform, illustrate sample the potential region be ideal polarizable electrode.The not spy of sample electrode
Schottky curve（Fig. 8）It confirmed that sample is p-type semiconductor, and measure the flat-band potential of sample（Fermi level）.Due to p-type
The fermi level of semiconductor is approximately equal to valence band, and in conjunction with the band gap that Fig. 5 is obtained, Fig. 9 is the energy of the one alkynes sample of graphite in embodiment 2
Band figure
Embodiment 3
With 1:100 ball material mass ratio, according to 1:18 molar ratio weighs hexaiodo benzene（C6I6）And calcium carbide（CaC2）, it is placed in true
In empty ball grinder, absolute ethyl alcohol is added to full of ball grinder.Ball grinder is sealed, planetary ball is passed through with 500 revs/min of rate
Grinding machine ball milling 12 hours, and washed and dried according to the sample that 1 the method for example completes ball milling.
With 8:1:1 mass ratio weighs active material（One alkynes powder of graphite）, conductive agent（Super P fine powders）And bonding
Agent（Kynoar）, solvent is added（1-Methyl-2-Pyrrolidone）In, it is stirred into slurry under dry atmosphere.It will slurry
Material is uniformly applied on copper foil, is placed in vacuum drying chamber and is dried 24 hours with 60 DEG C of temperature, is cut into a diameter of 14 millimeters
Disk is assembled into the button cell of CR2016 types in the glove box full of argon gas after weighing.Wherein, lithium metal is used as to electricity
Pole, 1 M LiPF6EC/DMC（Volume ratio is 1:1）Solution is as electrolyte, using Celgard-2300 diaphragms.Constant current fills
Discharge test carries out in LAND test systems, and charging and discharging currents density is 100 milliamperes/gram, charging/discharging voltage ranging from 0.01
~ 3.0 volts.
The cycle performance of the one alkynes material of graphite in 0.1 ~ 3.0 volt of voltage range is as shown in Figure 10.As can be seen that
Under the current density of 100 milliamperes/gram, sample possesses certain storage lithium performance.
Claims (6)
1. a kind of preparation method of alkynyl carbon material, the carbon material is one alkynes powder of class graphite, it is characterised in that specific steps
It is as follows：
（1）By phenyl-hexahalide（C6X6）, calcium carbide（CaC2）It is placed in ball grinder with ball milling pearl, absolute ethyl alcohol is added；Seal ball milling
Tank vacuumizes ball grinder or is passed through inert gas；The molar ratio of phenyl-hexahalide and calcium carbide is 1:6~1:18；
（2）By planetary ball mill with 400 ~ 600 revs/min of rate ball milling 6 ~ 18 hours；
（3）Take out step（2）The unreacted calcium carbide of removal is washed with deionized in the sample that ball milling is completed；
（4）By step（3）Obtained product is dried with 40 ~ 90 DEG C, and is pulverized；
（5）By step（4）Obtained product washing, removes unreacted phenyl-hexahalide；
（6）By step（5）Obtained product is with 40 ~ 90 DEG C of drying to get to one alkynes powder of graphite.
2. preparation method according to claim 1, it is characterised in that phenyl-hexahalide is to appoint in hexachloro-benzene, hexabromobenzene or hexaiodo benzene
It is a kind of.
3. preparation method according to claim 1, it is characterised in that the control of ball material mass ratio is 20:1~100:1.
4. preparation method according to claim 1, it is characterised in that the amount of absolute ethyl alcohol need to not there be ball milling pearl at least.
5. preparation method according to claim 1, it is characterised in that the inert atmosphere is nitrogen（N2）Or argon gas
（Ar）.
6. a kind of one alkynes power applications of the graphite that preparation method as described in claim 1 obtains are in catalysis material, electrochemistry
Or lithium ion battery negative material.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108946698A (en) * | 2018-08-18 | 2018-12-07 | 复旦大学 | A method of based on benzene precursor preparation γ type graphite list alkynes nano-carbon material |
| CN110371946A (en) * | 2019-08-12 | 2019-10-25 | 安徽工业大学 | A kind of naphthalyne carbon material, preparation method and application |
| CN113083234A (en) * | 2021-03-08 | 2021-07-09 | 西北大学 | Adsorbent for adsorbing dye-containing wastewater, preparation method and application |
| CN113104838A (en) * | 2021-04-30 | 2021-07-13 | 天津工业大学 | Preparation method of plasma fluorine-doped modified gamma-type graphite single alkyne carbon material |
| CN113651311A (en) * | 2021-07-16 | 2021-11-16 | 西安理工大学 | Alkynyl carbon material, preparation method thereof and composite electrode |
| CN114436244A (en) * | 2021-12-06 | 2022-05-06 | 中国地质大学（武汉） | Preparation method of graphite diyne |
| CN115010126A (en) * | 2022-07-08 | 2022-09-06 | 北方民族大学 | Method for preparing graphite diyne by using alkynyl negative ions |
| CN115124026A (en) * | 2022-06-28 | 2022-09-30 | 天津工业大学 | Bamboo-like gamma-type graphite monoalkyne material and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105948015A (en) * | 2016-04-27 | 2016-09-21 | 北京化工大学 | Method for synthesizing carbyne nano-material from calcium carbide and polyhalohydrocarbon as raw materials through ball-milling |
| CN108083272A (en) * | 2017-12-27 | 2018-05-29 | 复旦大学 | A kind of preparation method of graphite alkene carbon material |
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2018
- 2018-01-18 CN CN201810047016.6A patent/CN108373147A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105948015A (en) * | 2016-04-27 | 2016-09-21 | 北京化工大学 | Method for synthesizing carbyne nano-material from calcium carbide and polyhalohydrocarbon as raw materials through ball-milling |
| CN108083272A (en) * | 2017-12-27 | 2018-05-29 | 复旦大学 | A kind of preparation method of graphite alkene carbon material |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108946698A (en) * | 2018-08-18 | 2018-12-07 | 复旦大学 | A method of based on benzene precursor preparation γ type graphite list alkynes nano-carbon material |
| CN108946698B (en) * | 2018-08-18 | 2021-08-20 | 复旦大学 | Method for preparing gamma-type graphite single alkyne nano carbon material based on benzene precursor |
| CN110371946A (en) * | 2019-08-12 | 2019-10-25 | 安徽工业大学 | A kind of naphthalyne carbon material, preparation method and application |
| CN113083234A (en) * | 2021-03-08 | 2021-07-09 | 西北大学 | Adsorbent for adsorbing dye-containing wastewater, preparation method and application |
| CN113083234B (en) * | 2021-03-08 | 2022-08-09 | 西北大学 | Adsorbent for adsorbing dye-containing wastewater, preparation method and application |
| CN113104838A (en) * | 2021-04-30 | 2021-07-13 | 天津工业大学 | Preparation method of plasma fluorine-doped modified gamma-type graphite single alkyne carbon material |
| CN113651311A (en) * | 2021-07-16 | 2021-11-16 | 西安理工大学 | Alkynyl carbon material, preparation method thereof and composite electrode |
| CN114436244A (en) * | 2021-12-06 | 2022-05-06 | 中国地质大学（武汉） | Preparation method of graphite diyne |
| CN114436244B (en) * | 2021-12-06 | 2023-10-17 | 中国地质大学（武汉） | Preparation method of graphite diyne |
| CN115124026A (en) * | 2022-06-28 | 2022-09-30 | 天津工业大学 | Bamboo-like gamma-type graphite monoalkyne material and preparation method thereof |
| CN115010126A (en) * | 2022-07-08 | 2022-09-06 | 北方民族大学 | Method for preparing graphite diyne by using alkynyl negative ions |
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Application publication date: 20180807 |