CN107381600B - Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material - Google Patents
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/08—Simple or complex cyanides of metals
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- C01B19/00—Selenium; Tellurium; Compounds thereof
- C01B19/007—Tellurides or selenides of metals
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- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/06—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron
- C01B21/064—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with boron
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Abstract
The method for synthesizing inorganic cyanogen compound the present invention relates to carbon-to-carbon rupture and preparing one-dimensional coiled material from two-dimensional material, a small number of layer two-dimensional material dispersion liquids are mixed and stirred for reacting in proportion with metal salt solution under certain reaction condition, generate flocculent deposit, C-C key fracture in used solvent, generate cyanide, two-dimensional material is changed into one dimensional atom crystal coiled material, after filtration drying, obtains cyanide and one dimensional atom crystal coiled material.Compared with prior art, reaction condition of the present invention is mild, is not necessarily to high temperature and pressure; reaction speed is fast, three-waste free discharge, is environmental-friendly synthesis preparation method; prepare with scale can be achieved, not only there is important theory significance, but also there are also extensive real value and application prospects.
Description
Technical field
The invention belongs to organic syntheses and advanced function technical field of material, more particularly, to one kind with two-dimensional material
For the method that one-dimensional roll of material is prepared in raw material, and passes through carbon-to-carbon rupture and synthesize three key cyanide of carbon-to-nitrogen.
Background technique
Chemical bond activation is the important research direction of Synthetic Organic Chemistry, wherein can be made by the activation fracture of carbon-carbon bond
A series of standby noval chemical compounds with significant application value, therefore, the catalytic activation of carbon-carbon bond break to form new chemical bond at
For one of research hotspot in recent years.But fracture carbon-to-carbon singly-bound is not easy to, typically by using the gold of high activity
Belong to organic compound as catalyst and carry out catalytic cleavage, still, these catalysis reactions are sensitivity to air and water electrode, react item
Part is stringent, and the catalyst used is all not easy preparation and stores for a long time.Recently, studies have reported that using silver salt hydro-thermal/
The fracture of the high temperature and pressure catalysis carbon-carbon bond of solvent heat.But at normal temperature, carry out carbon-to-carbon fracture does not see report.
Carbon-to-nitrogen key compound is widely present in organism and nature, closely related with human lives, wherein is based on
The cyanogen compound of three key of carbon-to-nitrogen can synthesize a large amount of various drugs, pesticide, food additives and auxiliary chemicals etc., have extensively
Application value.It is general that carbon-nitrogen bond chemical combination is mainly obtained by complex reaction process using the catalyst based on platinum, copper or nickel
Object.The method that three key compound of carbon-to-nitrogen mainly uses Pintsch process synthesizes, and still, the report synthesized at room temperature is absolutely not.
With two-dimensional material graphene discovery and further investigation since, the two-dimensional atomic crystal material of similar graphene
Start to get more and more people's extensive concerning.Graphene and other two-dimensional materials such as BN, MoS2, WS2, MoSe2, NbSe2, TaSe2,
Bi2Te3 has important scientific valence because having excellent electricity, optics, calorifics, magnetics and mechanical performance, in many fields
Value and wide application prospect.Such as in microelectronic component, supercapacitor, hydrogen storage material, shielding material, anti-corrosion material, catalysis
Material, photoelectric material, the fields such as electromagnetic material are with important application prospects.These two-dimensional materials haveing excellent performance pass through volume
Mode can form the one-dimensional material of similar multi-walled carbon nanotube.The one-dimensional material of this similar multi-walled carbon nanotube, Yin Qite
The structure of different internal structure and edge non-close not only with the excellent properties of two-dimensional material, but also possesses two-dimensional material
Therefore the excellent properties not having become one of the hot spot studied recently.But currently, one-dimensional material is prepared by two-dimensional material
The research report of material is considerably less, moreover, the method reported not only low yield, but also method complexity, uses without practical preparation
Value.
Furthermore, it is possible to carry out carbon-to-carbon rupture synthesis three key compound of carbon-to-nitrogen simultaneously and prepared from two-dimensional material one-dimensional
The method of material has not been reported.
Summary of the invention
The purpose of the present invention is for carbon-to-carbon singly-bound break to form new chemical bond, three key compound of carbon-to-nitrogen preparation and
Two-dimensional material be rolled into one-dimensional material method there are the problem of, provide it is a kind of can both carry out carbon-to-carbon singly-bound fracture, synthesis carbon-to-nitrogen
Two-dimensional material can also be become the new method of one-dimensional material volume by three key compounds, and the new method reaction condition is mild, without height
Warm high pressure, reaction speed is fast, three-waste free discharge, is environmental-friendly synthesis preparation method, and can realize prepare with scale, not only
With important theory significance, and there are also extensive real value and application prospects.
The purpose of the present invention can be achieved through the following technical solutions:
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, by a small number of layer two-dimensional materials
Dispersion liquid is mixed and stirred for reacting in proportion with metal salt solution under certain reaction condition, the C-C in used solvent
Key fracture generates cyanide, and two-dimensional material is changed into one dimensional atom crystal coiled material, generates flocculent deposit and obtains after filtration drying
To cyanide and one dimensional atom crystal coiled material.
A small number of layer two-dimensional material dispersion liquids be a small number of layer two-dimensional materials are dispersed in concentration obtained in small molecule solvent be 1
The solution of~10mg/100ml.
Metal salt solution is that silver nitrate is dissolved in concentration obtained in small molecule solvent for the molten of 1~10mg/100ml
Liquid.
A small number of layer two-dimensional materials be two-dimensional atomic crystal material, including but not limited to the number of plies be 1-10 layers graphene, BN,
MoS2、WS2、MoSe2、NbSe2、TaSe2Or Bi2Te3Material.
Graphene, BN, the MoS of a small number of layer two-dimensional materials for 1-6 layers as a preferred technical solution,2Or WS2Material.
Small molecule solvent is ethyl alcohol.
The mass ratio control of a small number of layer two-dimensional materials and metal salt is 15:1~1:1.
A small number of layer two-dimensional material dispersion liquids and metal salt solution are mixed anti-under conditions of at 10-30 DEG C
Answer 10~120min.
Reaction temperature is 15-25 DEG C as a preferred technical solution, and the time that reaction is mixed is 30~60min.
This method can realize that C-C key is broken under mild reaction conditions, form cyanide, and two-dimensional material is turned
Become one-dimensional material, be that solvent and graphene are expressed as follows as the reaction mechanism of two-dimensional material using ethyl alcohol: graphene has catalysis
Agent function reduces energy required for the carbon-to-carbon rupture in reactant, ionizes out in nitrate solution under its effect
Nitrate ion, under the action of graphene catalysis, nitrate ion and alcohol generation esterification be (similar acetic acid and ethyl alcohol
Esterification), under the action of nitro electrophilic, the hydrogen on carbon atom is activated, and in the solution under the action of active oxygen, is taken off
Hydroxide loses a molecular water, forms nitrous anhydride compound, and under the action of further nitro electrophilic, nitrous anhydride compound is de-
The CO2 of a molecule is removed, realizes the fracture of C-C key, forms nitromethane, nitromethane forms cyanide intermediate by deoxidation, after
Person forms cyanide metal salt further across cyanide, so that end reaction is carried out to cyanide metal salt direction；Together
When, graphene changes the electron density distribution on its molecule under the action of being formed by cyanide metal salt, passes through reduction
Grapheme two-dimension material forms the initial energy barrier of one-dimensional material, and triggering grapheme two-dimension material starts to change, in intermolecular model moral
Under the action of Hua Li, by dropping low-surface-energy, final grapheme two-dimension material is transformed into graphene one-dimensional material.Entire reaction energy
The main reason for enough occurring is: grapheme two-dimension material plays the role of catalyst, and under catalysis, reactant occurs a series of
Esterification, dehydration and decarboxylic reaction, the cyanide metal salt of formation are the power for promoting entire reaction balanced sequence, meanwhile, institute
The metal cyanides of formation is uneven induction of the electron density distribution of grapheme two-dimension material, drives grapheme two-dimension material to drop
The direction that low-surface-energy reduces is transformed into the progress of one-dimensional material direction.
Used minority layer two-dimensional material can make catalyst, while itself is during the reaction, can be changed into one
Material is tieed up, this is another technical characteristic outstanding of the technical program.A small number of layer two-dimensional materials have special surface-active,
It is completely different with three-dimensional block materials with big specific surface area and electron density, just as graphene more than graphite active height,
With excellent properties such as excellent electricity, calorifics, mechanics.These a small number of layer two-dimensional materials have very high catalytic activity, can lure
Esterification occurs for the nitrate anion led in organic matter such as ethyl alcohol and nitrate, and a series of oxidative dehydrogenation of further occurrence loses
Hydrone, meanwhile, take off CO2 molecule.If not if a small number of layer two-dimensional materials, on the one hand, there is no catalytic activity, on the other hand,
Material thickness is too thick, and the driving force for forming one-dimensional material is not enough to realize the formation of one-dimensional material.
Compared with prior art, the invention has the characteristics that:
1, in terms of carbon-to-carbon singly-bound fracture and cyanogen compound synthesis, reaction condition of the present invention is mild, at room temperature can be fast
Speed carries out, and does not need high temperature and pressure, does not need complicated metallic catalyst, does not also need strong acid, highly basic etc., has important reason
By meaning and practical application value
2, in terms of two-dimensional material is converted into one-dimensional roll of material, the one-dimensional roll of material yield of generation is high, and reaction condition
Mildly, it carries out at normal temperatures and pressures, is not necessarily to special installation, simple process and low cost is suitble to amplification production, and reaction raw materials are suitable
It is wide with range, it is applicable to including but not limited to graphene, BN, MoS2、WS2Etc. two-dimensional atomic crystals material.
3, carbon-to-carbon rupture, cyanide are formed and two-dimensional material is converted into one-dimensional material and can carry out simultaneously.
Detailed description of the invention
Fig. 1 is the electron scanning micrograph that embodiment 1 prepares the one-dimensional volume of graphene；
Fig. 2 is the electron scanning micrograph that embodiment 2 prepares BN volumes；
Fig. 3 is that embodiment 3 prepares MoS2The electron scanning micrograph of volume；
Fig. 4 is that embodiment 4 prepares WS2The electron scanning micrograph of volume；
Fig. 5 is the Raman spectrum structural analysis figure for the cyanide that embodiment 1 is prepared；
Fig. 6 is the infared spectrum structural analysis figure for the cyanide that embodiment 1 is prepared；
Fig. 7 is the X-ray powder diffraction structural analysis figure for the cyanide that embodiment 1 is prepared.
Specific embodiment
The present invention is described in detail with specific embodiment below in conjunction with the accompanying drawings.Following embodiment will be helpful to this field
Technical staff further understand the present invention, but the invention is not limited in any way.It should be pointed out that the general of this field
For logical technical staff, without departing from the inventive concept of the premise, various modifications and improvements can be made.These are belonged to
Protection scope of the present invention.
Embodiment 1
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, using following steps:
(1) in ethanol by 2-5 layers of grapheme material dispersion, the graphene dispersing solution that concentration is 10mg/100mL is obtained
100mL；
(2) in ethanol by silver nitrate dissolution, it prepares and obtains the metal salt solution 50ml that concentration is 5mg/100mL；
(3) solution for preparing step (1), (2) mixes, and under conditions of 20 DEG C, stirs 10 minutes, is used
Solvent in the fracture of C-C key, generate cyanide, two-dimensional grapheme material is changed into one dimensional atom crystal coiled material, obtains black
Color flocky precipitate；
(4) precipitation and separation for obtaining step (3) is dry, obtains the one-dimensional coiled material of graphene and cyanogen compound.
Fig. 1 is the electron scanning micrograph that the present embodiment prepares the one-dimensional volume of graphene, it can be seen from the figure that this hair
The graphene roll structural integrity of bright preparation.The Raman spectrum structural analysis figure for the cyanide that Fig. 5-7 respectively reaction process obtains,
The x-ray powder for the cyanide that the infared spectrum structural analysis figure and reaction process for the cyanide that reaction process obtains obtain spreads out
Penetrate structural analysis figure.The RAM spectrum of Fig. 5 shows to contain cyanide ion in sample, and the infrared spectroscopy of Fig. 6 shows to contain cyanogen in sample
Radical ion, XRD show that sample cyanide salt is silver cyanide, contain one-dimensional graphite really to prove to be prepared in flocculent deposit
Alkene coiled material and cyanogen compound.
Embodiment 2
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, using following steps:
(1) in ethanol by 4-6 layers of BN material dispersion, the graphene dispersing solution that concentration is 10mg/100mL is obtained
50mL；
(2) in ethanol by silver nitrate dissolution, compound concentration is the metal salt solution 50ml of 5mg/100mL；
(3) solution for preparing step (1), (2) mixes, and under conditions of 10 DEG C, stirs 120 minutes, is adopted
C-C key fracture in solvent, generates cyanide, two-dimensional BN material is changed into one dimensional atom crystal coiled material, obtains white
Flocculent deposit；
(4) precipitation and separation for obtaining step (3) is dry, obtains one-dimensional BN coiled material and cyanogen compound.
Fig. 2 is the electron scanning micrograph that the present embodiment prepares BN volumes.It can be seen from the figure that prepared by the present invention
BN volume structure is complete, is one-dimensional linear material.
Embodiment 3
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, using following steps:
(1) by 6-10 layers of MoS2Material disperses the MoS for taking concentration to be 10mg/100mL in ethanol2A small number of layer dispersion liquids
100mL；
(2) in ethanol by silver nitrate dissolution, compound concentration is the metal salt solution 50ml of 2mg/100mL；
(3) solution for preparing step (1), (2) mixes, and under conditions of 30 DEG C, stirs 30 minutes, obtains ash
Color flocculent deposit；
(4) precipitation and separation for obtaining step (3) is dry, obtains one-dimensional MoS2Coiled material and cyanogen compound.
Fig. 3 is that the present embodiment prepares MoS2The electron scanning micrograph of volume.It can be seen from the figure that prepared by the present invention
MoS2Volume structure is complete, is one-dimensional linear material.
Embodiment 4
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, using following steps:
(1) by 1-3 layers of WS2Material disperses a small number of layer WS for taking concentration to be 10mg/100mL in ethanol2Dispersion liquid
100mL；
(2) in ethanol by silver nitrate dissolution, compound concentration is the metal salt solution 100ml of 1mg/100mL；
(3) solution for preparing step (1), (2) mixes, and under conditions of 15 DEG C, stirs 60 minutes, obtains ash
Color flocculent deposit；
(4) precipitation and separation for obtaining step (3) is dry, obtains one-dimensional WS2Coiled material and cyanogen compound.
Fig. 4 is that the present embodiment prepares WS2The electron scanning micrograph of volume.It can be seen from the figure that prepared by the present invention
WS2Volume structure is complete, is one-dimensional linear material.
Embodiment 5
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, by the two dimension of 3-6 layers of structure
TaSe2Material dispersion liquid and silver nitrate solution hybrid reaction 60min under conditions of 15 DEG C, wherein TaSe2Material dispersion liquid is
By TaSe2Material disperses in ethanol, and concentration is controlled in 1mg/100ml, and silver nitrate solution is to dissolve silver nitrate in ethanol,
Concentration is controlled in 10mg/100ml, TaSe2The control of the mass ratio of two-dimensional material and silver nitrate is 15:1, during the reaction, institute
C-C key fracture in the solvent of use, generates cyanide, and two-dimensional material is changed into one dimensional atom crystal coiled material, and it is cotton-shaped heavy to generate
It forms sediment, after filtration drying, obtains cyanide and one dimensional atom crystal coiled material.
Embodiment 6
Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, by the two dimension of 4-8 layers of structure
Bi2Te3Material dispersion liquid and silver nitrate solution hybrid reaction 30min under conditions of 25 DEG C, wherein Bi2Te3Material dispersion liquid
It is by Bi2Te3Material dissolves in ethanol, and concentration is controlled in 2mg/100ml, and silver nitrate solution is that silver nitrate is dissolved in ethyl alcohol
In, concentration is controlled in 8mg/100ml, TaSe2The control of the mass ratio of two-dimensional material and silver nitrate is 10:1, during the reaction,
C-C key fracture in used solvent, generates cyanide, and two-dimensional material is changed into one dimensional atom crystal coiled material, generates cotton-shaped
Precipitating, after filtration drying, obtains cyanide and one dimensional atom crystal coiled material.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring substantive content of the invention.
Claims (9)
1. method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material, which is characterized in that this method will
A small number of layer two-dimensional material dispersion liquids are mixed and stirred for reacting in proportion with metal salt solution under certain reaction condition, generate wadding
Shape precipitates, and the C-C key fracture in used solvent generates cyanide, and two-dimensional material is changed into one dimensional atom crystal coiled material, passes through
After filtration drying, cyanide and one dimensional atom crystal coiled material are obtained；The metal salt solution is to dissolve silver nitrate in ethanol
Obtained solution.
2. the method that carbon-to-carbon rupture according to claim 1 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, a small number of layer two-dimensional material dispersion liquids are that a small number of layer two-dimensional materials are dissolved in small molecule solvent to obtain
Concentration be 1~10mg/100ml solution.
3. the method that carbon-to-carbon rupture according to claim 1 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, the metal salt solution is the solution of 1~10mg/100ml of concentration.
4. the method that carbon-to-carbon rupture according to claim 2 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, a small number of layer two-dimensional materials are two-dimensional atomic crystal material, be graphene, BN that the number of plies is 1-10 layers,
MoS2、WS2、MoSe2、NbSe2、TaSe2Or Bi2Te3Material.
5. carbon-to-carbon rupture according to claim 2 or 4 synthesizes cyanide and prepares the side of one-dimensional coiled material from two-dimensional material
Method, which is characterized in that preferred 1-6 layers of the graphene of a small number of layer two-dimensional materials, BN, MoS2Or WS2Material.
6. the method that carbon-to-carbon rupture according to claim 2 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, the small molecule solvent is ethyl alcohol.
7. the method that carbon-to-carbon rupture according to claim 1 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, the mass ratio control of a small number of layer two-dimensional materials and metal salt is 15:1~1:1.
8. the method that carbon-to-carbon rupture according to claim 1 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, a small number of layer two-dimensional material dispersion liquids and metal salt solution reaction temperature be 10-30 DEG C under conditions of,
10~120min of reaction is mixed.
9. the method that carbon-to-carbon rupture according to claim 8 synthesizes cyanide and prepares one-dimensional coiled material from two-dimensional material,
It is characterized in that, reaction temperature is preferably 15-25 DEG C, the time that reaction is mixed is preferably 30~60min.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102083786A (en) * | 2007-10-12 | 2011-06-01 | 隆萨有限公司 | Method for the preparation of organic nitrates |
| CN102874844A (en) * | 2012-10-25 | 2013-01-16 | 河南银城科技股份有限公司 | Method for producing silver potassium cyanide |
| CN106629588A (en) * | 2016-11-22 | 2017-05-10 | 哈尔滨理工大学 | Technology for fusing carbon-carbon bonds of carbon nanotubes by means of electron beam irradiation |
-
2017
- 2017-07-21 CN CN201710600318.7A patent/CN107381600B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102083786A (en) * | 2007-10-12 | 2011-06-01 | 隆萨有限公司 | Method for the preparation of organic nitrates |
| CN102874844A (en) * | 2012-10-25 | 2013-01-16 | 河南银城科技股份有限公司 | Method for producing silver potassium cyanide |
| CN106629588A (en) * | 2016-11-22 | 2017-05-10 | 哈尔滨理工大学 | Technology for fusing carbon-carbon bonds of carbon nanotubes by means of electron beam irradiation |
Non-Patent Citations (2)
| Title |
|---|
| Carbon-Nitrogen Bond-Forming Reactions of Palladacycles with Hypervalent Iodine Reagents;Allison R.Dick et al.;《Organometallics》;20070216(第26期);1365-1370 |
| Ethanol Electro-oxidation on Palladium Revisited Using Polarization Modulation Infrared Reflection Absorption Spectroscopy (PM-IRRAS) and Density Functional Theory (DFT): Why Is It Difficult To Break the C−C Bond;Evans A. Monyoncho et al.;《ACS Catalysis》;20160628(第6期);4894-4906 |
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