CN114047180A - Method for detecting chromate ions and dichromate ions - Google Patents
Method for detecting chromate ions and dichromate ions Download PDFInfo
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- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 title claims abstract description 24
- -1 dichromate ions Chemical class 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 20
- 150000001450 anions Chemical class 0.000 claims abstract description 46
- 238000001514 detection method Methods 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 230000005496 eutectics Effects 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 16
- VIHPSDJHXPAPCY-UHFFFAOYSA-N cyclopenta-1,3-diene 3-(2-cyclopenta-2,4-dien-1-ylphenyl)-1-phenylprop-2-en-1-one iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.O=C(C=Cc1ccccc1-[c-]1cccc1)c1ccccc1 VIHPSDJHXPAPCY-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000012544 monitoring process Methods 0.000 claims abstract description 9
- 229940077449 dichromate ion Drugs 0.000 claims abstract description 7
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 117
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 16
- 239000011259 mixed solution Substances 0.000 claims description 14
- 230000008859 change Effects 0.000 claims description 12
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 10
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 8
- 235000019743 Choline chloride Nutrition 0.000 claims description 8
- 229910004882 Na2S2O8 Inorganic materials 0.000 claims description 8
- 239000007832 Na2SO4 Substances 0.000 claims description 8
- 229910003243 Na2SiO3·9H2O Inorganic materials 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 8
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 8
- 229960003178 choline chloride Drugs 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 8
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- 238000000862 absorption spectrum Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 claims description 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Substances [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 5
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 5
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000002211 ultraviolet spectrum Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000011651 chromium Substances 0.000 description 29
- 150000002500 ions Chemical class 0.000 description 19
- 239000000523 sample Substances 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000012512 characterization method Methods 0.000 description 7
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 7
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- 238000009210 therapy by ultrasound Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000036039 immunity Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000013074 reference sample Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000006378 damage Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- SPKJCVZOZISLEI-UHFFFAOYSA-N cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-ylethanone;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CC(=O)C1=CC=C[CH-]1 SPKJCVZOZISLEI-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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- Chemical & Material Sciences (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses a dichromate ion and a chromate ion detection method, belongs to the field of chemical synthesis and anion detection, adopts DES (DES-catalyzed synthesis) to synthesize ferrocenyl chalcone, and has the advantages of simple operation, high yield, mild reaction conditions, short reaction time, environmental friendliness, low cost and the like, and a eutectic solvent can be reused. Due to the existence of unsaturated bonds, the invention also can selectively detect the compounds under different anions and has good recognition effect on the anions. And the compound can convert a microscopic anion recognition event into an anion receptor which is easy to detect macroscopically and changes the color of the solution or changes the ultraviolet spectrum, has the advantages of cheap instrument, simple operation, easy monitoring and the like in detection, and has important significance for detecting a water sample in the environment.
Description
Technical Field
The invention belongs to the field of chemical synthesis and anion detection, and relates to a method for detecting chromate ions and dichromate ions.
Background
Chalcone is one kind of flavonoid, exists in safflower, licorice and other plant species, and its mother body has bioactivity and pharmacological activity and may be used in resisting bacteria, diminishing inflammation, resisting tumor, resisting virus, etc; the ferrocene also has good biological activity, and the synthesized ferrocenyl chalcone has better activity by the principle of activity superposition, is used in the field of medicine, and plays a good role in the aspects of treating cancers, tumors and the like. Meanwhile, the ferrocenyl chalcone is an important intermediate for organic synthesis. Ferrocene derivatives containing a heterocycle may thus be prepared.
Dichromate ion (Cr)2O7 2-) And chromate ion (CrO)4 2-) Is widely applied in the industrial production processes of electroplating, metallurgy, pigment production, leather tanning, wood preservation and the like, and hexavalent chromium [ Cr (VI)]The Cr (VI) has carcinogenicity, the strong oxidizing property of the Cr (VI) can damage DNA and interfere the repair of the DNA, the Cr (VI) can also damage the skeleton of liver cells and even cause the death of the liver cells, and the probability of respiratory cancer is greatly improved when the Cr (VI) with high concentration is contacted for a long time, so that the research on the Cr (VI) with high efficiency and accuracy can cause harm to the health of human bodies2O7 2-And CrO4 2-The method has important significance in the fields of human health, environmental management, clinical medicine and the like.
It is important to design a receptor compound having high affinity and selectivity for anions. The method can convert a microscopic anion recognition event into an anion receptor which is easy to detect macroscopically and has solution color change or ultraviolet spectrum change, and has the advantages of cheap instrument, simplicity in operation, easiness in monitoring and the like in detection, so that the method is particularly concerned by people.
Disclosure of Invention
The invention aims to overcome the defects of Cr in the prior art2O7 2-And CrO4 2-The detection method of (2) is not easily recognized in other molecules, secondly due to Cr2O7 2-And CrO4 2-The ion solution has corresponding color and is easy to be confused with other ions, so that the dichromate ions and the chromate ion detection method are providedThe method is carried out.
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
a method for detecting chromate ions and dichromate ions comprises the following steps:
step 1) preparing a eutectic solvent;
step 2) mixing the acetyl ferrocene, the aromatic aldehyde and the eutectic solvent, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished to obtain a mixed solution;
step 3) mixing the mixed solution with deionized water, performing suction filtration after solid is separated out, and sequentially washing and drying a filter cake to obtain ferrocenyl chalcone;
step 4), preparing a ferrocenyl chalcone solution to obtain a solution to be detected;
preparing an anion solution;
step 5) mixing the anion solution with the solution to be detected to obtain a detection solution, observing the color change of the detection solution, and identifying whether chromate ions and dichromate ions exist in the anion solution based on the color change of the detection solution;
and testing the ultraviolet absorption spectrum of the detection solution, and calculating to obtain the contents of chromate ions and dichromate ions in the anion solution.
Preferably, the eutectic solvent is a mixed solution of choline chloride and urea.
Preferably, the molar ratio of choline chloride, urea, acetyl ferrocene and aromatic aldehyde is 1: (1-4): 0.1: (0.1-0.15).
Preferably, the anionic solution is C6H5COONa、NaHSO3、NaF、CH3COONa、NaBr、 Na2Cr2O7·2H2O、Na2CO3、Na2SO4、Na2S、Na2S2O8、Na2C2O4、Na2SiO3·9H2O、 NaH2PO4·2H2O, NaI, NaCl and K2CrO4The mixed solution of (1).
Preferably, the volume ratio of the anion solution to the solution to be tested is 100: 1.
preferably, when the anion solution and the solution to be measured are mixed, the concentration of the anion solution is 1X 10-2mol/L；
The concentration of the solution to be measured is 1X 10-4mol/L。
Preferably, whether chromate ions and dichromate ions exist in the anion solution is identified based on the color change of the detection solution, specifically: when the detection solution changes from light yellow to dark yellow, the anion solution contains Cr2O7 2-。
Preferably, whether chromate ions and dichromate ions exist in the anion solution is identified based on the color change of the detection solution, specifically: under the irradiation of 365nm ultraviolet lamp, the solution turns from colorless to yellow, and the anion solution contains Cr2O7 2-And CrO4 2-。
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a dichromate ion and a chromate ion detection method, which adopts DES to catalyze and synthesize ferrocenyl chalcone, and has the advantages of simple operation, high yield, mild reaction conditions, short reaction time, environmental protection, low cost and the like, and the eutectic solvent can be reused. Due to the existence of unsaturated bonds, the invention also can selectively detect the compounds under different anions and has good recognition effect on the anions. And the compound can convert a microscopic anion recognition event into an anion receptor which is easy to detect in a macroscopic manner and changes in solution color or ultraviolet spectrum, has the advantages of cheap instrument, simplicity in operation, easiness in monitoring and the like in detection, and has important significance for detecting a water sample in an environment.
Drawings
FIG. 1 is a FT-IR spectrum of 1-phenyl-3-ferrocenyl ketene;
FIG. 2 is 1-phenyl-3-ferrocenylenone1H NMR spectrum;
FIG. 3 is 1-phenyl-3-ferrocenylKetene13C NMR spectrum;
FIG. 4 shows the addition of Cr to the 1-phenyl-3-ferrocenylenone2O7 2-Ultraviolet-visible absorption spectrum of the ion;
FIG. 5 shows the addition of CrO to the 1-phenyl-3-ferrocenylenone pair4 2-Ultraviolet-visible absorption spectrum of the ion;
FIG. 6 shows 1-phenyl-3-ferrocenylenone vs. Cr2O7 2-Interference immunity of the ions;
FIG. 7 shows 1-phenyl-3-ferrocenylenone vs. CrO4 2-Interference immunity of the ions;
FIG. 8 is a graph showing the effect of the number of times of repeated use of the eutectic solvent on the yield of ferrocenyl chalcone.
Detailed Description
The invention is described in further detail below with reference to the accompanying drawings:
example 1
Preparation of 1-phenyl-3-ferrocenyl ketene
Adding 11mmol choline chloride and 22mmol urea into a reaction vessel, and stirring at 80 ℃ to obtain a colorless transparent solution, namely the eutectic solvent. Adding 1.1mmol of acetylferrocene and 1.3mmol of benzaldehyde, carrying out reflux reaction, and monitoring by TLC until the reaction is finished; after the reaction is finished, adding a small amount of water into the reaction container, separating out solids, carrying out suction filtration, washing a filter cake with water, drying to obtain the 1-phenyl-3-ferrocenyl ketene, and evaporating the filtrate for reuse.
The structure characterization result and the infrared characterization data of the product are shown in figure 1: IR (KBr) v 3093cm-1(-CH＝), 1674cm-1(C＝O),1624cm-1(C＝C),1493cm-1,1450cm-1(Ar,Fc),742cm-1, 702cm-1(Ar-H)。
The characterization data of the hydrogen spectra are shown in FIG. 2:1H NMR(DMSO-d6,400MHz)δ:4.25(s,5H,Fc-H), 4.63(s,2H,Fc-H),4.95(s,2H,Fc-H),7.14-7.18(d,1H,＝CH),7.29-7.68(m,5H,Ph-H), 7.81-7.85(d,1H,＝CH).
characterization data of the carbon spectra are shown in FIG. 3:13C NMR(DMSO-d6,100MHz)δ:192.47,140.38, 134.70,129.63,128.46,127.79,122.46,80.12,72.31,69.63,69.25.
example 2
Preparation of 1- (4-methyl) phenyl-3-ferrocenylenone
Adding 11mmol choline chloride and 22mmol urea into a reaction vessel, and stirring at 80 ℃ to obtain a colorless transparent solution, namely the eutectic solvent. Adding 1.1mmol of acetyl ferrocene and 1.3mmol of 4-methylbenzaldehyde, carrying out reflux reaction, and monitoring by TLC until the reaction is finished; after the reaction is finished, adding a small amount of water into the reaction container, separating out solids, carrying out suction filtration, washing a filter cake with water, drying to obtain the 1- (4-methyl) phenyl-3-ferrocenyl ketene, and evaporating the filtrate for reuse.
The structural characterization data for the product is: IR (KBr) v 3098cm-1(-CH＝),2980,1370cm-1(-CH3), 1647cm-1(C＝O),1590cm-1(C＝C),1503cm-1,1434cm-1(Ar,Fc),809cm-1(Ar-H).
1H NMR(400MHz,DMSO-d6),δ:2.43(s,3H,-CH3),4.23(s,5H,Fc-H),4.62(s, 2H,Fc-H),4.93(s,2H,Fc-H),7.12～7.16(d,1H,＝CH),7.27～7.30(d,2H,Ph-H), 7.58～7.60(d,2H,Ph-H),7.80～7.84(d,1H,＝CH).
13C NMR(100MHz,DMSO-d6),δ:192.58,140.43,140.09,131.85,129.42, 127.79,122.46,80.12,72.31,69.63,69.25,21.06。
Example 3
Preparation of 1- (4-hydroxy) phenyl-3-ferrocenylenone
Adding 11mmol choline chloride and 22mmol urea into a reaction vessel, and stirring at 80 ℃ to obtain a colorless transparent solution, namely the eutectic solvent. Adding 1.1mmol of acetyl ferrocene and 1.3mmol of 4-hydroxybenzaldehyde, carrying out reflux reaction, and monitoring by TLC until the reaction is finished; after the reaction is finished, adding a small amount of water into the reaction container, separating out solids, carrying out suction filtration, washing a filter cake with water, drying to obtain the 1- (4-hydroxy) phenyl-3-ferrocenyl ketene, and evaporating the filtrate for reuse.
The structural characterization data for the product is: IR (KBr) v 3465cm-1(-OH),3075cm-1(-CH＝), 1653cm-1(C＝O),1585cm-1(C＝C),1503cm-1,1434cm-1(Ar,Fc),812cm-1(Ar-H).
1H NMR(400MHz,DMSO-d6),δ:4.23(s,5H,Fc-H),4.62(s,2H,Fc-H),4.93(s, 2H,Fc-H),7.12～7.16(d,1H,＝CH),7.27～7.30(d,2H,Ph-H),7.58～7.60(d,2H,Ph-H), 7.80～7.84(d,1H,＝CH),9.59(s,1H,-OH)。
13C NMR(100MHz,DMSO-d6),δ:193.58,136.42,134.02,129.12,123.79, 121.46,80.12,72.31,69.63,69.25,21.06
Example 4
Preparation of 1- (4-nitro) phenyl-3-ferrocenylenone
Adding 11mmol choline chloride and 22mmol urea into a reaction vessel, and stirring at 80 ℃ to obtain a colorless transparent solution, namely the eutectic solvent. Adding 1.1mmol of acetyl ferrocene and 1.3mmol of 4-nitrobenzaldehyde, carrying out reflux reaction, and monitoring by TLC until the reaction is finished; after the reaction is finished, adding a small amount of water into the reaction container, separating out solids, carrying out suction filtration, washing a filter cake with water, drying to obtain the 1- (4-nitro) phenyl-3-ferrocenyl ketene, and evaporating the filtrate for reuse.
The structural characterization data for the product is: IR (KBr) v 3096cm-1(-CH＝),1658cm-1(C＝O), 1583cm-1(C＝C),1507cm-1,1458cm-1(Ar,Fc),1365cm-1(-N＝O),815cm-1(Ar-H).
1H NMR(DMSO-d6,400MHz)δ:4.24(s,5H,Fc-H),4.54(s,2H,Fc-H),4.80(s,2H, Fc-H),7.26-7.29(d,1H,＝CH),7.57-7.59(d,2H,Fc-H),7.80-7.82(d,2H,Fc-H), 8.12-8.13(d,1H,＝CH).
13C NMR(DMSO-d6,100MHz)δ:192.65,137.44,134.00,129.55,124.99,123.81, 121.48,80.01,72.81,69.75,69.40.
Example 5
1-phenyl-3-ferrocenylenone on Cr2O7 2-Selective detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2Cr2O7·2H2O,Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O, NaH2PO4·2H2Anion salts such as O, NaI, NaCl, etc. are prepared in a 1X 10 configuration using ultrapure water-2The anionic solution of (2) for use. Accurately measuring 3ml of to-be-detected solution of 1-phenyl-3-ferrocenyl ketene by using a pipette, reserving one sample tube as a blank reference sample, respectively adding 30 mu l of the 15 test anion solutions into the rest 15 to-be-detected solutions by using the pipette, ultrasonically oscillating the 16 groups of samples, standing to uniformly disperse the samples, and then observing the color change of the 1-phenyl-3-ferrocenyl ketene. In the presence of Cr2O7 2-The ion solution is dark yellow, and the color of the solution added with other anion solutions is consistent with that of the solution to be detected of the 1-phenyl-3-ferrocenyl ketene. Under the irradiation of 365nm ultraviolet lamp, adding Cr2O7 2-The color of the ion changes from colorless to yellow, and the color of the other anion solution is added with 1-phenyl-3-The color of the solution to be detected of the ferrocenyl ketene is consistent. Thereby detecting Cr in the sample to be detected2O7 2-Ions.
Example 6
1-phenyl-3-ferrocenylenone para CrO4 2-Selective detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O,NaH2PO4·2H2O,NaI, NaCl,K2CrO4Plasma salt prepared with ultrapure water at a ratio of 1 × 10-2The anionic solution of (2) for use. Accurately measuring 3ml of to-be-detected solution of 1-phenyl-3-ferrocenyl ketene by using a pipette gun, placing one sample tube as a blank reference sample, respectively adding 30 mu l of the 15 test anion solutions into the rest 15 to-be-detected solutions by using the pipette gun, ultrasonically oscillating the 16 groups of samples, standing to uniformly disperse the samples, and then observing the color change of the 1-phenyl-3-ferrocenyl ketene. Adding CrO4 2-The ion and solution is dark yellow, and the color of the solution added with other anion is consistent with that of the solution to be detected of the 1-phenyl-3-ferrocenyl ketene. Under the irradiation of 365nm ultraviolet lamp, CrO is added4 2-The color of the ion changes from colorless to yellow, and the color of the solution added with other anions is consistent with that of the solution to be detected of the 1-phenyl-3-ferrocenyl ketene. Thereby detecting CrO in the sample to be detected4 2-Ions.
Example 7
1-phenyl-3-ferrocenylenone on Cr2O7 2-Selective detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2Cr2O7·2H2O,Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O, NaH2PO4·2H2Anion salts such as O, NaI, NaCl, etc. are prepared in a 1X 10 configuration using ultrapure water-2The anionic solution of (2) for use. Accurately measuring 3ml of to-be-tested solution of 1-phenyl-3-ferrocenyl ketene by using a liquid transfer gun, placing one sample tube as a blank reference sample, respectively adding 30 mu l of the 15 test anion solutions into the rest 15 to-be-tested solutions by using the liquid transfer gun, ultrasonically oscillating the 16 groups of samples, standing to uniformly disperse the samples, and then testing the ultraviolet-visible absorption spectrum of the 1-phenyl-3-ferrocenyl ketene. As can be seen from FIG. 4, the addition of Cr2O7 2-The ions show absorption peaks at 294nm and 372nm, and the figure shows that the added Cr2O7 2-Increased ultraviolet absorption intensity compared to other anions; it is demonstrated that 1-phenyl-3-ferrocenyl ketene can selectively identify Cr2O7 2-Ions.
Example 8
1-phenyl-3-ferrocenylenone para CrO4 2-Selective detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O,NaH2PO4·2H2O,NaI, NaCl,K2CrO4Plasma salt prepared with ultrapure water at a ratio of 1 × 10-2The anionic solution of (2) for use. By pipettingAccurately measuring 3ml of to-be-tested solution of 1-phenyl-3-ferrocenyl ketene by a gun, placing one sample tube as a blank reference sample, respectively adding 30 mu l of the 15 test anion solutions into the other 15 to-be-tested solutions by using a liquid-transferring gun, ultrasonically oscillating the 16 groups of samples, standing to uniformly disperse the samples, and then testing the ultraviolet-visible absorption spectrum of the 1-phenyl-3-ferrocenyl ketene. As can be seen from FIG. 5, the addition of CrO4 2-Absorption peaks at 295nm and 347nm, from which it can be seen that CrO was added4 2-CrO in contrast to other anions4 2-The ultraviolet absorption intensity of (2) is enhanced; it is demonstrated that 1-phenyl-3-ferrocenyl ketene can selectively recognize CrO4 2-Ions.
Example 9
1-phenyl-3-ferrocenylenone on Cr2O7 2-Interference immunity detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2Cr2O7·2H2O,Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O, NaH2PO4·2H2Anion salts such as O, NaI, NaCl, etc. are prepared in a 1X 10 configuration using ultrapure water-2The anionic solution of (2) for use. Accurately measuring 3mL of probe 1-phenyl-3-ferrocenyl ketene solution to be detected in 16 sample tubes by using a pipette, reserving a group of blank reference samples, adding 30 mu L of prepared anion solution into the rest 15 1-phenyl-3-ferrocenyl ketene solutions to be detected by using the pipette, and adding 30 mu L of Cr into the sample tubes2O7 2-And (4) ultrasonically oscillating all solution samples, standing to uniformly disperse the solution samples, and then measuring the ultraviolet spectrum of the solution samples. As can be seen from FIG. 4, the absorbance of the solution when 15 anions were added dropwise was compared with that of 1-phenyl-3-bisThe absorption degrees of the ferrocenyl ketene solutions to be tested are similar, and only Cr is contained2O7 2-The absorption strength of ions is enhanced, which shows that the 1-phenyl-3-ferrocenyl ketene to-be-detected solution can selectively identify Cr2O7 2-Ions; adding Cr again after adding the anionic solution to the 1-phenyl-3-ferrocenylenone2O7 2-Ionic solutions, as can be seen in fig. 6, the absorption strength is significantly enhanced. Description of 1-phenyl-ferrocenyl-enone for Cr2O7 2-The ion selective recognition method has good selective recognition effect, other ions do not interfere the selective recognition effect, and the ion selective recognition method can be applied to actual detection.
Example 10
1-phenyl-3-ferrocenylenone para CrO4 2-Interference immunity detection of
The 1-phenyl-3-ferrocenyl ketene adopts DMF, H2Dissolving in 1:1 mixed solution to obtain 1 × 10 concentration solution- 4And (3) carrying out ultrasonic treatment on the solution to be detected in mol/L. C is to be6H5COONa,NaHSO3,NaF,CH3COONa,NaBr, Na2CO3,Na2SO4,Na2S,Na2S2O8,Na2C2O4,Na2SiO3·9H2O,NaH2PO4·2H2O,NaI, NaCl,K2CrO4Plasma salt prepared with ultrapure water at a ratio of 1 × 10-2The anionic solution of (2) for use. Accurately measuring 3mL of probe 1-phenyl-3-ferrocenyl ketene solution to be detected in 16 sample tubes by using a pipette, reserving a group of sample tubes as blank reference samples, adding 30 mu L of prepared anion solution into the other 15 1-phenyl-3-ferrocenyl ketene solutions to be detected by using the pipette, and adding 30 mu L of CrO into the sample tubes4 2-And (4) ultrasonically oscillating all solution samples, standing to uniformly disperse the solution samples, and then measuring the ultraviolet spectrum of the solution samples. As can be seen from FIG. 7, when the absorbance of the solution added with 15 kinds of anions is similar to that of the solution to be tested of 1-phenyl-3-ferrocenylketene, only CrO is present4 2-The absorption strength of the ions is enhanced,this shows that the 1-phenyl-3-ferrocenyl ketene to-be-detected solution can selectively identify CrO4 2-Ions; adding CrO again after adding the anionic solution to 1-phenyl-3-ferrocenylenone4 2-Ionic solutions, as can be seen from the figure, the absorption strength is significantly enhanced. Description of 1-phenyl-ferrocenyl-enone on CrO4 2-The ion selective recognition method has good selective recognition effect, other ions do not interfere the selective recognition effect, and the ion selective recognition method can be applied to actual detection.
After the reaction is finished, the filtrate can be reused after being evaporated; the result of reusing the eutectic solvent for 5 times is shown in fig. 8, and the result shows that the eutectic solvent still has good catalytic activity after being reused for 5 times.
In conclusion, the invention discloses a synthetic method of ferrocenyl chalcone and Cr pair thereof2O7 2-And CrO4 2-The identification is that the ferrocenyl chalcone is synthesized by DES catalysis, the operation is simple, the yield is high, the reaction condition is mild, the reaction time is short, the environment is protected, the cost is low, the eutectic solvent can be reused, and the ferrocenyl chalcone can better detect Cr in the environment2O7 2-And CrO4 2-。
The above-mentioned contents are only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and any modification made on the basis of the technical solution according to the technical idea proposed by the present invention falls within the protection scope of the claims of the present invention.
Claims (8)
1. A method for detecting chromate ions and dichromate ions is characterized by comprising the following steps:
step 1) preparing a eutectic solvent;
step 2) mixing the acetyl ferrocene, the aromatic aldehyde and the eutectic solvent, carrying out reflux reaction, and monitoring by TLC (thin layer chromatography) until the reaction is finished to obtain a mixed solution;
step 3) mixing the mixed solution with deionized water, performing suction filtration after solid is separated out, and sequentially washing and drying a filter cake to obtain ferrocenyl chalcone;
step 4), preparing a ferrocenyl chalcone solution to obtain a solution to be detected;
preparing an anion solution;
step 5) mixing the anion solution with the solution to be detected to obtain a detection solution, observing the color change of the detection solution, and identifying whether chromate ions and dichromate ions exist in the anion solution based on the color change of the detection solution;
and testing the ultraviolet absorption spectrum of the detection solution, and calculating to obtain the contents of chromate ions and dichromate ions in the anion solution.
2. The method for detecting chromate ion and dichromate ion as claimed in claim 1, wherein the eutectic solvent is a mixed solution of choline chloride and urea.
3. The method of claim 2, wherein the molar ratio of choline chloride, urea, acetyl ferrocene, and aromatic aldehyde is 1: (1-4): 0.1: (0.1-0.15).
4. The method for detecting chromate ion and dichromate ion according to claim 1, wherein the anion solution is C6H5COONa、NaHSO3、NaF、CH3COONa、NaBr、Na2Cr2O7·2H2O、Na2CO3、Na2SO4、Na2S、Na2S2O8、Na2C2O4、Na2SiO3·9H2O、NaH2PO4·2H2O, NaI, NaCl and K2CrO4The mixed solution of (1).
5. The method for detecting chromate ion and dichromate ion according to claim 1, wherein the volume ratio of the anion solution to the solution to be detected is 100: 1.
6. the method for detecting chromate ion and dichromate ion according to claim 1, wherein the concentration of the anion solution is 1 x 10 when the anion solution and the solution to be measured are mixed-2mol/L；
The concentration of the solution to be measured is 1X 10-4mol/L。
7. The method for detecting chromate ions and dichromate ions according to claim 1, wherein the presence or absence of chromate ions and dichromate ions in the anion solution is recognized based on a color change of the detection solution, and specifically: when the detection solution changes from light yellow to dark yellow, the anion solution contains Cr2O7 2-。
8. The method for detecting chromate ions and dichromate ions according to claim 1, wherein the presence or absence of chromate ions and dichromate ions in the anion solution is recognized based on a color change of the detection solution, and specifically: under the irradiation of 365nm ultraviolet lamp, the solution turns from colorless to yellow, and the anion solution contains Cr2O7 2-And CrO4 2-。
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