CN109705168A - A kind of double-core nickel coordination compound and the preparation method and application thereof - Google Patents
A kind of double-core nickel coordination compound and the preparation method and application thereof Download PDFInfo
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- CN109705168A CN109705168A CN201910040803.2A CN201910040803A CN109705168A CN 109705168 A CN109705168 A CN 109705168A CN 201910040803 A CN201910040803 A CN 201910040803A CN 109705168 A CN109705168 A CN 109705168A
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 60
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 239000011259 mixed solution Substances 0.000 claims abstract description 9
- 239000002244 precipitate Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 235000019441 ethanol Nutrition 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 claims abstract description 5
- MJFCDPLEATUOPF-UHFFFAOYSA-L dichloronickel;triphenylphosphane Chemical compound Cl[Ni]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MJFCDPLEATUOPF-UHFFFAOYSA-L 0.000 claims abstract description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052786 argon Inorganic materials 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- GCNLQHANGFOQKY-UHFFFAOYSA-N [C+4].[O-2].[O-2].[Ti+4] Chemical compound [C+4].[O-2].[O-2].[Ti+4] GCNLQHANGFOQKY-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 13
- 239000001569 carbon dioxide Substances 0.000 abstract description 9
- 229910001453 nickel ion Inorganic materials 0.000 abstract description 6
- 230000001376 precipitating effect Effects 0.000 abstract description 6
- 230000001699 photocatalysis Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 3
- 238000006664 bond formation reaction Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 6
- VOKXPKSMYJLAIW-UHFFFAOYSA-N nickel;phosphane Chemical compound P.[Ni] VOKXPKSMYJLAIW-UHFFFAOYSA-N 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- 230000008016 vaporization Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000002447 crystallographic data Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000011941 photocatalyst Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000239290 Araneae Species 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000002803 fossil fuel Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010181 polygamy Effects 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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Abstract
The invention discloses a kind of double-core nickel coordination compounds and the preparation method and application thereof.Complex is [(dmbpy)2Ni2Cl4(H2O)2], molecular structural formula C24H28Cl4N4Ni2O2, wherein dmbpy is 4,4'- dimethyl -2,2'- bipyridyl, and Ni is bivalent nickel ion, and form is solid crystals.The crystal of the complex belongs to anorthic system, P-1 space group.4,4'- dimethyl -2,2'- bipyridyl and nickel ion pass through chlorine bridged bond formation binuclear molecule structure.The preparation method comprises the following steps: by triphenylphosphine dichloride nickel [NiCl2(PPh3)2] reacted in acetonitrile solution with 4,4'- dimethyl -2,2'- bipyridyl and obtain green precipitate, then precipitating is dissolved in the mixed solution of acetonitrile and ethyl alcohol, green crystal is obtained by slow solvent flashing.The present invention can be used as a kind of photochemical catalyst, GHG carbon dioxide is changed into methane gas and CO with high added value.Preparation process of the present invention is simple, easily implements, product purity and yield are higher, have a good application prospect in the photocatalytic conversion field of carbon dioxide.
Description
Technical field
The present invention relates to complex field of material technology, especially dinuclear metal complex and preparation method thereof
With application, more particularly, to a kind of double-core nickel coordination compound and the preparation method and application thereof.
Background technique
The energy majority that the mankind use at present is from fossil fuel, such as petroleum, coal etc..Due to the combustion of fossil fuel
Burning releases a large amount of CO2, serious challenge is brought to global environment problem.By CO2It is reduced to the change with high added value
The imagination for learning fuel, is that this solves the problems, such as one of this effective ways.In order to realize the purpose, it can use visible light catalytic
Restore CO2, obtain the new fuel such as CO, methane.Seeking efficient photochemical catalyst is to solve CO2The key point of reduction.Traditional
Photochemical catalyst generally selects noble metal compound, such as Ru, Ir, Pt, Pd complex.This kind of compound due to fancy price with
And harsh synthesis condition, so that it is not easily accomplished large-scale industrial production.But light is prepared into using cheap metal nickel and is urged
Agent, the report for restoring carbon dioxide, which is not much, to be seen, especially this kind of cheap metal compound is turned for carbon dioxide
It is even more extremely rare for turning to the report of methane.Select such compound that there is low-cost huge advantage as photochemical catalyst,
With high potential value.
Summary of the invention
In view of this, it is an object of the invention to 4,4'- dimethyl -2,2'- bipyridine ligand and dichloride triphenyl
Phosphine nickel [NiCl2(PPh3)2] it is that raw material using simple and easy method prepares novel double-core nickel coordination compound, with this
Complex is catalyst, applied to the reduction of photocatalysis carbon dioxide, obtains the methane gas with high added value and CO.
In order to solve above-mentioned technical problem, the present invention is adopted the following technical solutions:
(1) a kind of photocatalyst material is provided
The catalyst material is [(dmbpy)2Ni2Cl4(H2O)2], wherein dmbpy represents organic ligand 4,4'- dimethyl-
2,2'- bipyridyls, Ni are bivalent nickel ion, the nickel ion and organic ligand 4 of the catalyst material, 4'- dimethyl -2,2'- connection
Pyridine forms double-core nickel coordination compound by chlorine bridged bond.
(2) method of above-mentioned double-core nickel coordination compound is prepared
The preparation method includes the following steps；
S1. by 4,4'- dimethyl -2,2'- bipyridyl and [NiCl2(PPh3)2] be uniformly mixed in acetonitrile solution；
S2. it is passed through argon gas in the mixed liquor obtained by step S1, stirs lower reaction 6~24 hours.After reaction, it obtains green
Color precipitating；
S3. the green precipitate obtained by the mixed solution dissolving step S2 of acetonitrile and ethyl alcohol, slowly volatilizees, it is needle-shaped to obtain green
Crystal.
Further, 4,4'- dimethyl -2,2'- bipyridyl and [NiCl in the step S12(PPh3)2] molar ratio be 1:
0.5~1:1.
Further, the reaction temperature of the step S2 is 50 DEG C~80 DEG C.
Further, in the mixed solution of the step S3, the volume ratio of acetonitrile is 20~80%.
(3) application of double-core nickel coordination compound
Using the double-core nickel coordination compound as catalyst, applied to the photo catalytic reduction of carbon dioxide, carbon dioxide
Be converted to methane gas and CO.
The present invention has the advantages that compared with prior art:
Firstly, be utilized 4, the characteristics of dimethyl -2, the 2'- bipyridyl polygamy site 4'-, reach and nickel ion is formed and is coordinated
The purpose of compound.Tonghua chlorine bridged bond has obtained the coordination structure of double-core nickel.
Double-core nickel coordination compound has the multiple chloride ions and hydrone being coordinated with nickel ion in the present invention, is being catalyzed
Ligand substituting in have the characteristics that be easy to slough.
Secondly, metallic nickel feature cheap and easy to get is utilized using nickel coordination compound.
Third, photocatalyst material preparation of the invention is simple, and favorable reproducibility, yield is high, and product purity is high.
4th, photocatalyst structure of the invention is stablized, and thermal stability is high.
Detailed description of the invention
Fig. 1 is the molecular structure of double-core nickel coordination compound.
Fig. 2 is the single crystal samples of double-core nickel coordination compound and the powder diffraction comparison diagram of monocrystalline simulation.The figure proves, institute
The diffraction maximum of powder diffraction of single crystal samples and simulation of synthesis is consistent, illustrates that the sample purity of synthesis is high, and be target product.
Fig. 3 is the coordination structure figure of double-core nickel coordination compound.The chart is bright, and nickel ion forms double-core by chlorine bridged bond
Complex, and there are two hydrones to participate in coordination, the coordination of chloride ion and hydrone provides catalysis instead for catalytic process
Answer site.
Fig. 4 is the cyclic voltammogram of double-core nickel coordination compound.The bright synthesized double-core nickel coordination compound tool of the chart
There is big oxidation-reduction potential, embodies high catalytic activity.
Fig. 5 is to detect figure using double-core nickel coordination compound as the product gas phase chromatography of photochemical catalyst.The chart it is bright
Using double-core nickel coordination compound be catalyst when, can be carbon dioxide reduction be methane and carbon monoxide.
Fig. 6 is the product mass spectrogram tracked using isotope.Isotope tracking test shows methane and carbon monoxide
From the carbon dioxide sample being added, the validity of catalyst is further demonstrated.
Specific embodiment
The present invention is described in further details combined with specific embodiments below.
(1) double-core nickel coordination compound material is prepared
Embodiment 1
By 36.65mg (0.2mmol) 4,4'- dimethyl -2,2'- bipyridyl, 131.24mg (0.2mmol) dichloride triphen
Base phosphine nickel is added in 50mL acetonitrile and is uniformly mixed；It is passed through argon gas in gained mixed liquor, is stirred to react at 50 DEG C 20 hours
Later, green precipitate is obtained；Above-mentioned precipitating is dissolved with the mixed solution of acetonitrile and ethyl alcohol, wherein the volume of acetonitrile is 50%.It is slow
Slow vaporization 2 weeks, obtain green single crystal samples.
Embodiment 2
By 36.65mg (0.2mmol) 4,4'- dimethyl -2,2'- bipyridyl, 65.62mg (0.1mmol) dichloride triphen
Base phosphine nickel is added in 40mL acetonitrile and is uniformly mixed；It is passed through argon gas in gained mixed liquor, is stirred to react at 60 DEG C 15 hours
Later, green precipitate is obtained；Above-mentioned precipitating is dissolved with the mixed solution of acetonitrile and ethyl alcohol, wherein the volume of acetonitrile is 50%.It is slow
Slow vaporization 2 weeks, obtain green single crystal samples.
Embodiment 3
By 36.65mg (0.2mmol) 4,4'- dimethyl -2,2'- bipyridyl, 98.28mg (0.15mmol) dichloride triphen
Base phosphine nickel is added in 60mL acetonitrile and is uniformly mixed；It is passed through argon gas in gained mixed liquor, is stirred to react at 70 DEG C 15 hours
Later, green precipitate is obtained；Above-mentioned precipitating is dissolved with the mixed solution of acetonitrile and ethyl alcohol, wherein the volume of acetonitrile is 60%.It is slow
Slow vaporization 2 weeks, obtain green single crystal samples.
Embodiment 4
By 36.65mg (0.2mmol) 4,4'- dimethyl -2,2'- bipyridyl, 65.62mg (0.1mmol) dichloride triphen
Base phosphine nickel is added in 40mL acetonitrile and is uniformly mixed；It is passed through argon gas in gained mixed liquor, is stirred to react at 70 DEG C 10 hours
Later, green precipitate is obtained；Above-mentioned precipitating is dissolved with the mixed solution of acetonitrile and ethyl alcohol, wherein the volume of acetonitrile is 70%.It is slow
Slow vaporization 2 weeks, obtain green single crystal samples.
(2) measurement of double-core nickel structure of coordination compound
Table 1: the parameter list of double-core nickel coordination compound crystal
Sizeable monocrystalline is chosen under the microscope, at temperature T=293 (2) K, in Rigaku R-AXIS
On SPIDER diffractometer, Mo-K ray is used with through graphite monochromator monochromatizationIt is collected in a manner of ω-φ
Diffraction data.Absorption correction is carried out by ABSCOR program.It is parsed using direct method using SHELXTL program and refined structure.
Whole non-hydrogen atom coordinates first are determined with difference function method and least square method, and non-hydrogen atom coordinate and anisotropic parameters carry out
Complete matrix least square method amendment, then the hydrogen atom position of main body framework is obtained with theoretical hydrogenation method, then use least square method
Refine is carried out to crystal structure.The partial parameters of crystallography point diffraction data collection and structure refinement see the above table 1.
Powder diffraction data collection is completed on Rigaku D-MAX 2200VPC diffractometer.
Single crystal diffraction is completed on Rigaku R-AXIS SPIDER diffractometer.
Gas chromatographic detection is completed in SHIMADZU GC-2014C.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention.For those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways.There is no necessity and possibility to exhaust all the enbodiments.It is all this
Made any modifications, equivalent replacements, and improvements etc., should be included in the claims in the present invention within the spirit and principle of invention
Protection scope within.
Claims (8)
1. a kind of double-core nickel coordination compound, which is characterized in that the chemical formula of the complex is [(dmbpy)2Ni2Cl4
(H2O)2], wherein dmbpy 4,4'- dimethyl -2,2'- bipyridyl, the complex form double-core nickel by chlorine bridged bond
Coordination structure.
2. double-core nickel coordination compound according to claim 1, which is characterized in that the crystal of the complex belongs to
Anorthic system, space group P-1, cell parameter are respectively as follows:B=10.1220 (10),
3. the method for preparing double-core nickel coordination compound as described in claim 1, comprising the following steps:
S1. by 4,4'- dimethyl -2,2'- bipyridyl and triphenylphosphine dichloride nickel [NiCl2(PPh3)2] mixed in acetonitrile
It is even；
S2. it is passed through argon gas in the mixed liquor obtained by step S1, stirs lower reaction 6~24 hours, obtains green precipitate；
S3. the mixed solution of green precipitate acetonitrile obtained by step S2 and ethyl alcohol is dissolved, is slowly volatilized, obtain the needle-shaped crystalline substance of green
Body.
4. preparation method according to claim 3, which is characterized in that 4,4'- dimethyl -2,2'- joins in the step S1
Pyridine ligand and triphenylphosphine dichloride nickel [NiCl2(PPh3)2] molar ratio be 1:0.5~1:1.
5. preparation method according to claim 3, which is characterized in that the reaction temperature of the step S2 is 50 DEG C~80
℃。
6. preparation method according to claim 3, which is characterized in that in the mixed solution of the step S3, the body of acetonitrile
Product is than being 20~80%.
7. application of the double-core nickel coordination compound as described in claim 1 as photochemical catalyst.
8. application according to claim 7, which is characterized in that using the complex as catalyst, titanium dioxide
Carbon conversion is methane gas and CO.
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| CN112341501A (en) * | 2020-11-12 | 2021-02-09 | 云南师范大学 | Tetranuclear nickel-based complex with tetramethyl phenanthroline as ligand, and synthesis method and photocatalytic application thereof |
| CN112341501B (en) * | 2020-11-12 | 2023-06-20 | 云南师范大学 | Tetranuclear nickel-based complex with tetramethyl phenanthroline as ligand, and synthesis method and photocatalysis application thereof |
| JP2022129732A (en) * | 2021-02-25 | 2022-09-06 | 株式会社豊田中央研究所 | Carbon dioxide reduction catalyst, carbon dioxide reduction device, and artificial photosynthesis device |
| JP7291165B2 (en) | 2021-02-25 | 2023-06-14 | 株式会社豊田中央研究所 | Carbon dioxide reduction catalyst, carbon dioxide reducer, and artificial photosynthesis device |
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