CN107381600A - Carbon-carbon bond fracture synthesis cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material - Google Patents
Carbon-carbon bond fracture synthesis cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material Download PDFInfo
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- CN107381600A CN107381600A CN201710600318.7A CN201710600318A CN107381600A CN 107381600 A CN107381600 A CN 107381600A CN 201710600318 A CN201710600318 A CN 201710600318A CN 107381600 A CN107381600 A CN 107381600A
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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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- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B19/00—Selenium; Tellurium; Compounds thereof
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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 present invention relates to the method that carbon-carbon bond fracture synthesizes inorganic cyanogen compound and one-dimensional coiled material is prepared from two-dimensional material, a small number of layer two-dimensional material dispersion liquids under certain reaction condition are mixed and stirred for reacting in proportion with metal salt solution, generate flocculent deposit, C C keys fracture in used solvent, generate cyanide, two-dimensional material is changed into one dimensional atom crystal coiled material, after filtered drying, obtains cyanide and one dimensional atom crystal coiled material.Compared with prior art, reaction condition of the present invention is gentle, without HTHP; reaction speed is fast, three-waste free discharge, is environment-friendly synthesis preparation method; prepare with scale can be achieved, not only with important theory significance, and also extensive real value and application prospect.
Description
Technical field
The invention belongs to organic synthesis and advanced function technical field of material, more particularly, to one kind with two-dimensional material
The method of one-dimensional roll of material is prepared for raw material, and the key cyanide of carbon-to-nitrogen three is synthesized by carbon-to-carbon rupture.
Background technology
Chemical bond activation is the important research direction of Synthetic Organic Chemistry, wherein, it 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 into
For one of study 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 and carry out catalytic cleavage as catalyst, still, these catalytic reactions are sensitivity to air and water electrode, react bar
Part is strict, and the catalyst used is all not easy to prepare and deposited for a long time.Recently, studies have reported that using silver salt hydro-thermal/
The fracture of the HTHP catalysis carbon-carbon bond of solvent heat.But at normal temperatures, 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, it is based on
The cyanogen compound of the key of carbon-to-nitrogen three can synthesize substantial amounts of various medicines, agricultural chemicals, 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
Thing.The key compound of carbon-to-nitrogen three is mainly synthesized using the method for Pintsch process, and still, the report synthesized at room temperature does not have completely.
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 science valency in many fields because having excellent electricity, optics, calorifics, magnetics and mechanical performance
Value and wide application prospect.Such as in microelectronic component, ultracapacitor, hydrogen storage material, shielding material, anti-corrosion material, catalysis
The fields such as material, photoelectric material, electromagnetic material have important application prospect.The two-dimensional material of these excellent performances passes 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
Different internal structure and the structure of edge non-close, the not only excellent properties with two-dimensional material, but also possess two-dimensional material
The excellent properties not having, therefore, turn into one of focus studied recently.But at present, 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, and method is complicated, is used without actual prepare
Value.
Furthermore, it is possible to the carbon-to-carbon rupture synthesis key compound of carbon-to-nitrogen three is carried out simultaneously and is prepared from two-dimensional material one-dimensional
The method of material has no report.
The content of the invention
The purpose of the present invention be for carbon-to-carbon singly-bound break to form new chemical bond, the key compound of carbon-to-nitrogen three prepare and
Two-dimensional material is rolled into the problem of one-dimensional material method is present, there is provided a kind of both to have carried out carbon-to-carbon singly-bound fracture, synthesis carbon-to-nitrogen
Three key compounds, two-dimensional material can also be become to the new method of one-dimensional material volume, the new method reaction condition is gentle, without height
Warm high pressure, reaction speed is fast, three-waste free discharge, is environment-friendly synthesis preparation method, and can realize prepare with scale, not only
With important theory significance, and also extensive real value and application prospect.
The purpose of the present invention can be achieved through the following technical solutions：
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared 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 is broken, and generates cyanide, and two-dimensional material is changed into one dimensional atom crystal coiled material, generates flocculent deposit, after filtered drying, obtains
To cyanide and one dimensional atom crystal coiled material.
A small number of layer two-dimensional material dispersion liquids are that a small number of layer two-dimensional materials are dispersed in the concentration that is obtained in small molecule solvent is 1
~10mg/100ml solution.
Metal salt solution is that silver nitrate is dissolved in the concentration that is obtained in small molecule solvent is the molten of 1~10mg/100ml
Liquid.
A small number of layer two-dimensional materials are two-dimensional atomic crystal material, including but not limited to the number of plies be the graphenes of 1-10 layers, BN,
MoS2、WS2、MoSe2、NbSe2、TaSe2Or Bi2Te3Material.
As preferable technical scheme, a small number of layer two-dimensional materials are graphene, BN, MoS of 1-6 layers2Or WS2Material.
Small molecule solvent is ethanol.
The mass ratio control of described a small number of layer two-dimensional materials and metal salt is 15:1~1:1.
Described a small number of layer two-dimensional material dispersion liquids, under conditions of 10-30 DEG C, mix instead with metal salt solution
Answer 10~120min.
As preferable technical scheme, reaction temperature is 15-25 DEG C, and the time for mixing reaction is 30~60min.
This method can under gentle reaction condition realizes that C-C keys are broken, and forms cyanide, and two-dimensional material is turned
It is changed into one-dimensional material, is that the reaction mechanism of solvent and graphene as two-dimensional material is expressed as follows using ethanol：Graphene has catalysis
Agent function, under its effect, the energy required for the carbon-to-carbon rupture in reactant is reduced, is ionized out in nitrate solution
Nitrate ion, in the presence of graphene catalysis, nitrate ion and alcohol generation esterification be (similar acetic acid and ethanol
Esterification), in the presence of nitro electrophilic, the hydrogen on carbon atom is activated, and in the solution in the presence of active oxygen, is taken off
Hydroxide loses a molecular water, forms nitrous anhydride compound, in the presence of further nitro electrophilic, nitrous anhydride compound takes off
The CO2 of a molecule is removed, realizes that C-C keys are broken, 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 in the presence of the cyanide metal salt formed, 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
In the presence of Hua Li, by reducing surface energy, final grapheme two-dimension material is transformed into graphene one-dimensional material.Whole reaction energy
Enough occur the main reason for be：Grapheme two-dimension material serves the effect 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 whole 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, it is transformed into the progress of one-dimensional material direction.
Used a small number of layer two-dimensional materials can make catalyst, while itself is during the course of the reaction, can be changed into one
Material is tieed up, this is another technical characteristic protruded 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 is high more than graphite active,
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
Lead organic matter such as ethanol and esterification occurs with the nitrate anion in nitrate, and a series of oxidative dehydrogenation further occurs and loses
Hydrone, meanwhile, take off CO2 molecules.If not if a small number of layer two-dimensional materials, on the one hand, without 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：
1st, in terms of carbon-to-carbon singly-bound fracture and cyanogen compound synthesis, reaction condition of the present invention is gentle, at room temperature can be fast
Speed is carried out, it is not necessary to HTHP, it is not necessary to complicated metallic catalyst, it is not required that strong acid, highly basic etc., have important reason
By meaning and actual application value
2nd, 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
Gently, carry out at normal temperatures and pressures, without special installation, technique is simple, and cost is cheap, is adapted to amplification production, and reaction raw materials are fitted
It is wide with scope, it is applicable to including but not limited to graphene, BN, MoS2、WS2Etc. two-dimensional atomic crystal material.
3rd, carbon-to-carbon rupture, cyanide are formed and two-dimensional material is converted into one-dimensional material and can carried out simultaneously.
Brief description of the drawings
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.
Embodiment
The present invention is described in detail with specific embodiment below in conjunction with the accompanying drawings.Following examples will be helpful to this area
Technical staff further understand the present invention, but the invention is not limited in any way.It should be pointed out that to the general of this area
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
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, using following steps：
(1) it is the grapheme material of 2-5 layers is scattered in ethanol, obtain the graphene dispersing solution that concentration is 10mg/100mL
100mL；
(2) by silver nitrate dissolving in ethanol, prepare and obtain the metal salt solution 50ml that concentration is 5mg/100mL；
(3) solution that step (1), (2) prepare to obtain is mixed, under conditions of 20 DEG C, stirs 10 minutes, used
Solvent in the fracture of C-C keys, generate cyanide, two-dimentional grapheme material is changed into one dimensional atom crystal coiled material, obtains black
Color flocky precipitate；
(4) precipitation for obtaining step (3) separates drying, 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 that this hair
The graphene roll structural integrity of bright preparation.Fig. 5-7 be respectively course of reaction obtain cyanide Raman spectrum structural analysis figure,
The x-ray powder for the cyanide that the infared spectrum structural analysis figure and course of reaction for the cyanide that course of reaction obtains obtain spreads out
Penetrate structural analysis figure.Fig. 5 RAM spectrum show to contain cyanide ion in sample, and Fig. 6 infrared spectrum shows to contain cyanogen in sample
Radical ion, XRD show that sample cyanide salt is silver cyanide, contain one-dimensional graphite in flocculent deposit really so as to prove to be prepared
Alkene coiled material and cyanogen compound.
Embodiment 2
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, using following steps：
(1) it is the BN materials of 4-6 layers is scattered in ethanol, obtain the graphene dispersing solution that concentration is 10mg/100mL
50mL；
(2) by silver nitrate dissolving in ethanol, compound concentration is 5mg/100mL metal salt solution 50ml；
(3) solution that step (1), (2) prepare to obtain is mixed, under conditions of 10 DEG C, stirs 120 minutes, adopted
C-C keys fracture in solvent, generates cyanide, two-dimentional BN materials are changed into one dimensional atom crystal coiled material, obtain white
Flocculent deposit；
(4) precipitation for obtaining step (3) separates drying, obtains one-dimensional BN coiled materials and cyanogen compound.
Fig. 2 is the electron scanning micrograph that the present embodiment prepares BN volumes.It can be seen that prepared by the present invention
BN volume structures are complete, are one-dimensional linear material.
Embodiment 3
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, using following steps：
(1) by the MoS of 6-10 layers2Material is scattered in ethanol, takes the MoS that concentration is 10mg/100mL2A small number of layer dispersion liquids
100mL；
(2) by silver nitrate dissolving in ethanol, compound concentration is 2mg/100mL metal salt solution 50ml；
(3) solution that step (1), (2) prepare to obtain is mixed, under conditions of 30 DEG C, stirs 30 minutes, obtain ash
Color flocculent deposit；
(4) precipitation for obtaining step (3) separates drying, 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 that prepared by the present invention
MoS2Volume structure is complete, is one-dimensional linear material.
Embodiment 4
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, using following steps：
(1) by the WS of 1-3 layers2Material is scattered in ethanol, takes a small number of layer WS that concentration is 10mg/100mL2Dispersion liquid
100mL；
(2) by silver nitrate dissolving in ethanol, compound concentration is 1mg/100mL metal salt solution 100ml；
(3) solution that step (1), (2) prepare to obtain is mixed, under conditions of 15 DEG C, stirs 60 minutes, obtain ash
Color flocculent deposit；
(4) precipitation for obtaining step (3) separates drying, 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 that prepared by the present invention
WS2Volume structure is complete, is one-dimensional linear material.
Embodiment 5
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, by the two dimension of 3-6 Rotating fields
TaSe2Material dispersion liquid and silver nitrate solution hybrid reaction 60min under conditions of 15 DEG C, wherein, TaSe2Material dispersion liquid is
By TaSe2Material is scattered 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 course of the reaction, institute
C-C keys 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
Form sediment, after filtered drying, obtain cyanide and one dimensional atom crystal coiled material.
Embodiment 6
Carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, by the two dimension of 4-8 Rotating fields
Bi2Te3Material dispersion liquid and silver nitrate solution hybrid reaction 30min under conditions of 25 DEG C, wherein, Bi2Te3Material dispersion liquid
It is by Bi2Te3Material is dissolved in ethanol, and concentration is controlled in 2mg/100ml, and silver nitrate solution is that silver nitrate is dissolved in into ethanol
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 course of the reaction,
C-C keys fracture in used solvent, cyanide is generated, two-dimensional material is changed into one dimensional atom crystal coiled material, and generation is cotton-shaped
Precipitation, after filtered drying, obtains cyanide and one dimensional atom crystal coiled material.
The specific embodiment of the present invention is described above.It is to be appreciated that the invention is not limited in 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 the substantive content of the present invention.
Claims (9)
1. carbon-to-carbon rupture synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material, it is characterised 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, generation wadding
Shape precipitates, and the C-C keys fracture in used solvent, generates cyanide, 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.
2. carbon-to-carbon rupture according to claim 1 synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material,
Characterized in that, described 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. a kind of method that one-dimensional roll of material is prepared from two-dimensional material according to claim 1, it is characterised in that described
Metal salt solution is that silver nitrate is dissolved in the solution that the concentration obtained in small molecule solvent is 1~10mg/100ml.
4. carbon-to-carbon rupture according to claim 2 synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material,
Characterized in that, described a small number of layer two-dimensional materials are two-dimensional atomic crystal material, including but not limited to the number of plies is 1-10 layers
Graphene, BN, MoS2、WS2、MoSe2、NbSe2、TaSe2Or Bi2Te3Material.
5. the carbon-to-carbon rupture according to claim 2 or 4 synthesizes cyanide and the side of one-dimensional coiled material is prepared from two-dimensional material
Method, it is characterised in that graphene, BN, MoS of the described preferred 1-6 layers of a small number of layer two-dimensional materials2Or WS2Material.
6. the carbon-to-carbon rupture according to Claims 2 or 3 synthesizes cyanide and the side of one-dimensional coiled material is prepared from two-dimensional material
Method, it is characterised in that described small molecule solvent is ethanol.
7. carbon-to-carbon rupture according to claim 1 synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material,
Characterized in that, the mass ratio control of described a small number of layer two-dimensional materials and metal salt is 15:1~1:1.
8. carbon-to-carbon rupture according to claim 1 synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material,
Characterized in that, described a small number of layer two-dimensional material dispersion liquids and metal salt solution be under conditions of reaction temperature is 10-30 DEG C,
Mix 10~120min of reaction.
9. carbon-to-carbon rupture according to claim 8 synthesizes cyanide and the method that one-dimensional coiled material is prepared from two-dimensional material,
Characterized in that, reaction temperature is preferably 15-25 DEG C, the time for mixing reaction is preferably 30~60min.
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| CN201710600318.7A CN107381600B (en) | 2017-07-21 | 2017-07-21 | Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material |
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| CN201710600318.7A CN107381600B (en) | 2017-07-21 | 2017-07-21 | Method carbon-to-carbon rupture synthesis cyanide and prepare one-dimensional coiled material from two-dimensional material |
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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 |
|---|
| ALLISON R.DICK ET AL.: "Carbon-Nitrogen Bond-Forming Reactions of Palladacycles with Hypervalent Iodine Reagents", 《ORGANOMETALLICS》 * |
| EVANS A. MONYONCHO ET AL.: "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", 《ACS CATALYSIS》 * |
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