CN112557479B - Method for distinguishing alpha-naphthol and isomer beta-naphthol thereof - Google Patents
Method for distinguishing alpha-naphthol and isomer beta-naphthol thereof Download PDFInfo
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 title claims abstract description 136
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 title claims abstract description 136
- 229950011260 betanaphthol Drugs 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000010355 oscillation Effects 0.000 claims abstract description 145
- 239000000126 substance Substances 0.000 claims abstract description 66
- 229910020366 ClO 4 Inorganic materials 0.000 claims abstract description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 35
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 claims description 14
- 239000001230 potassium iodate Substances 0.000 claims description 14
- 229940093930 potassium iodate Drugs 0.000 claims description 14
- 235000006666 potassium iodate Nutrition 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000000452 restraining effect Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- GCDVVDACUSFVPY-UHFFFAOYSA-N 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetrazacyclotetradeca-7,14-diene Chemical compound CC1=NCCNC(C)(C)CC(C)=NCCNC(C)(C)C1 GCDVVDACUSFVPY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 116
- 238000001228 spectrum Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000001629 suppression Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003712 anti-aging effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004451 qualitative analysis Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 102000036675 Myoglobin Human genes 0.000 description 1
- 108010062374 Myoglobin Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- PHJMFIJWEOTPEP-UHFFFAOYSA-I [Na+].[Na+].[Cr+3].[O-]C1=C(C=C(C=C1)[N+]([O-])=O)N=NC1=C([O-])C=CC2=C1C=CC=C2.[O-]C1=CC(=C2C=C(C=CC2=C1N=NC1=C([O-])C=CC2=C1C=CC=C2)[N+]([O-])=O)S([O-])(=O)=O Chemical compound [Na+].[Na+].[Cr+3].[O-]C1=C(C=C(C=C1)[N+]([O-])=O)N=NC1=C([O-])C=CC2=C1C=CC=C2.[O-]C1=CC(=C2C=C(C=CC2=C1N=NC1=C([O-])C=CC2=C1C=CC=C2)[N+]([O-])=O)S([O-])(=O)=O PHJMFIJWEOTPEP-UHFFFAOYSA-I 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004035 chlorins Chemical class 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
A method for distinguishing alpha-naphthol and isomer beta-naphthol thereof is characterized in that: application "H 2 SO 4 ‑KIO 3 ‑[NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 The chemical oscillation system is used as a distinguishing solution, and the distinction of alpha-naphthol and beta-naphthol is realized according to different influences of the alpha-naphthol and the beta-naphthol on the oscillation of the system. The potential oscillation map provided by the distinguishing method has intuitiveness, can distinguish alpha-naphthol and beta-naphthol conveniently and rapidly, and has simple equipment, high accuracy and easy operation and observation.
Description
Technical Field
The invention relates to a distinguishing method, in particular to a tetrazacyclotetradienyl nickel complex [ NiL](ClO 4 ) 2 A method for distinguishing isomers of alpha-naphthol and beta-naphthol by a catalytic chemical oscillation system comprises the steps of preparing 5,7,7,12,14, 14-hexamethyl-1, 4,8, 11-tetraazacyclotetradec-4, 11-diene as a ligand L, and belongs to the field of qualitative analysis chemistry.
Background
The isomers of alpha-naphthol and beta-naphthol play a significant role in each other in the respective fields. Alpha-naphthol, formula: c (C) 10 H 8 O, alpha-naphthol can be used as raw material of pesticide carbaryl, and can be used for preparing preservative and medicine for resisting mild rheumatism in the pharmaceutical industry. Is also an effective antioxidant for a plurality of aldehydes, mineral oil and vegetable oil, is widely used as a synthetic spice, a rubber anti-aging agent and a color former of color film, and is a basic raw material of organic synthesis industry, medical industry and dye industry. It is also used for producing plastics, rubber anti-ageing agent and colour film coupler. Beta-naphthol, formula: c (C) 10 H 8 O, beta-naphthol is an important organic raw material and dye intermediate for producing tobias acid, butyric acid and beta-naphthol-3-formic acid, and for producing anti-aging agent butyl, anti-aging agent DNP and other anti-aging agents, organic pigment and bactericide. Also used for producing dyes such AS acid orange Z, acid medium black T, bisphenol AS-SW, reactive brilliant orange X-GN, neutral black BGL, direct copper salt blue 2R, and the like. The reagent is used for measuring sulfonamide and arylamine substances by using a thin layer chromatography. The method is used for improving cathode polarization, refining crystallization and reducing pores in acid tinning.
Since alpha-naphthol and its isomer beta-naphthol belong to positional isomers, the molecular formulas of the alpha-naphthol and the beta-naphthol are identical and the structures of the alpha-naphthol and the beta-naphthol are similar, so that some physical and chemical properties of the alpha-naphthol and the beta-naphthol are similar, the alpha-naphthol and the beta-naphthol are difficult to distinguish, and the given analysis of the alpha-naphthol and the beta-naphthol brings difficulty. The currently reported methods for detecting alpha-naphthol and the isomer beta-naphthol thereof mainly comprise thin layer chromatography, gas chromatography, spectrophotometry and high performance liquid chromatography. However, the identification method for distinguishing the two is not reported, so that a qualitative analysis method with good distinguishing effect, simple and quick operation and easy judgment of the result is very necessary. The two structures are shown in the structural formula (I)
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Alpha-naphthol beta-naphthol
The structures of alpha-naphthol and beta-naphthol of structural formula (I)
Disclosure of Invention
The invention aims to provide a novel, convenient and quick distinguishing method for alpha-naphthol and beta-naphthol, namely, application of NiL](ClO 4 ) 2 The distinguishing method of the catalytic chemical oscillation system for the alpha-naphthol and the beta-naphthol is an electrochemical oscillation system method developed based on the sensitive response of the complex catalytic chemical oscillation system for the alpha-naphthol and the beta-naphthol. Specifically, samples (alpha-naphthol and beta-naphthol) with the same concentration to be distinguished are respectively added into two groups of chemical oscillation systems, and the distinction of the samples to be distinguished is realized according to different influences of the samples to be distinguished on the chemical oscillation systems: if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a longer period of restraining time, the added sample to be distinguished is alpha-naphthol; if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a short period of restraining time, the added sample to be distinguished is beta-naphthol; and the invention deals withThe sample time is short, the measurement condition is simple and easy to control, and the popularization and the application are convenient.
The invention solves the technical problems and adopts the following technical scheme:
the invention provides a distinguishing method for alpha-naphthol and beta-naphthol, which is characterized in that:
ethanol is used as a solvent to prepare a solution of a sample to be distinguished;
application "H 2 SO 4 - KIO 3 - [NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 The chemical oscillation system is used as a distinguishing solution, the potential oscillation map of the chemical oscillation system is recorded, and the solutions of the alpha-naphthol and the beta-naphthol of the samples to be distinguished are respectively added into two groups of distinguishing solutions (chemical oscillation systems) at any stable potential lowest point, so that qualitative analysis of the samples to be distinguished is realized according to different influences of the samples to be distinguished on the chemical oscillation system: if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a longer period of restraining time, the added sample to be distinguished is alpha-naphthol; if the chemical oscillation is restrained after the solution to be distinguished is added, the oscillation is recovered after a short period of restraining time, and then the added sample to be distinguished is beta-naphthol.
Any stable potential minimum point generated by oscillation refers to any potential minimum point from 3 rd to 25 th generated by oscillation.
The tetraazacyclotetradiene nickel complex of the invention is [ NiL](ClO 4 ) 2 Wherein ligand L is 5,7,7,12,14, 14-hexamethyl-1, 4,8, 11-tetraazacyclotetradec-4, 11-diene. [ NiL](ClO 4 ) 2 The structure is shown as (II)
Structural formula (II) [ NiL ]](ClO 4 ) 2 Is of the structure of (a)
The structure of the complex and key structure chlorins of myoglobin, hemoglobin, chlorophyll and some metalloenzymes in living bodiesThe rings being very similar, this is done by [ NiL](ClO 4 ) 2 The catalyzed chemical oscillation reaction is similar to biochemical oscillations within plant and animal cells. Therefore, the system has stable vibration amplitude, long vibration life and sharp response to alpha-naphthol and beta-naphthol.
[NiL](ClO 4 ) 2 The preparation of (2) comprises two steps: 1) Preparation of L.2HClO 4 The method comprises the steps of carrying out a first treatment on the surface of the 2) From L.2HClO 4 Preparation of NiL](ClO 4 ) 2 。
1) Preparation of L.2HClO 4 ：
98.5mL of ethylenediamine was placed in a 500mL three-necked flask, and 126mL of 70% perchloric acid was slowly added dropwise with stirring over 120 minutes under ice-bath conditions. The initial reaction was vigorous with white smoke generation, so the drop rate was controlled to l drops every 5 seconds. The dropping speed can be accelerated properly as the reaction proceeds until the dropping is completed, and a transparent solution is obtained. 224mL of anhydrous acetone was added to the clear solution, still under ice-water bath, and stirred vigorously, the solution quickly becoming cloudy while forming a very viscous mixture. Still in the ice-water bath for 2-3 hours to allow for adequate reaction. The obtained product is transferred to a buchner funnel for suction filtration and separation, and is fully washed by acetone, thus obtaining pure white solid. Recrystallizing the pure self-colored solid in hot methanol-water solution, and vacuum drying with silica gel desiccant to obtain 80g white crystal L.2HClO 4 。
Reference is made to:
1.Curtis, N. F. and Hay, R. W. , J. Chem. Soc. , Chem. Commun. , 1966, p. 534.
2.Gang Hu, Panpan Chen, Wei Wang, Lin Hu, Jimei Song, LingguangQiu, Juan Song, E1ectrochimica Acta, 2007, Vol. 52, pp. 7996-8002.
3. Lin Hu, Gang Hu, Han-Hong Xu, J. Ana1. Chem. , 2006, Vol. 61, NO. 10, pp. 1021-1025.
4. hu Gang, doctor's paper, p25-27, fertilizer combination, 2005.
2) From L.2HClO 4 Preparation of NiL](ClO 4 ) 2 ：
Will 11g Ni(AC) 2 4H 2 O and 21g of L.2HClO 4 Placing in 500mL three-necked flask, dissolving in 250mL methanol, refluxing in hot water bath for 3 hours, finally generating yellow precipitate, filtering, concentrating filtrate in hot water bath to l/2 of original volume, standing overnight, and crystallizing completely to obtain yellow crystal. The yellow crystals were transferred to a buchner funnel and washed with methanol, recrystallized in a hot ethanol-water solution and dried in vacuo to give 8g of [ NiL ]](ClO 4 ) 2 Bright yellow crystals.
Reference is made to:
1. N. F. Curtis, J. Chem. Soc. Dolton Tran. , 1972, Vol. 13, 1357.
2. hu Gang, doctor's paper, p42-43, fertilizer combination, 2005.
2) From L.2HClO 4 Preparation of NiL](ClO 4 ) 2 ：
11g Ni (AC) 2 4H 2 O and 21g of L.2HClO 4 Placing in 500mL three-necked flask, dissolving in 250mL methanol, refluxing in hot water bath for 3 hours, finally generating yellow precipitate, filtering, concentrating filtrate in hot water bath to l/2 of original volume, standing overnight, and crystallizing completely to obtain yellow crystal. The yellow crystals were transferred to a buchner funnel and washed with methanol, recrystallized in a hot ethanol-water solution and dried in vacuo to give 8g of [ NiL ]](ClO 4 ) 2 Bright yellow crystals.
Reference is made to:
1. N. F. Curtis, J. Chem. Soc. Dolton Tran. , 1972, Vol. 13, 1357.
2. hu Gang, doctor's paper, p42-43, fertilizer combination, 2005.
The distinguishing method is different from the prior art in that the invention applies' H 2 SO 4 -KIO 3 -[NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 The chemical oscillation system is used as a distinguishing solution, and the distinction between alpha-naphthol and beta-naphthol is realized by different influences of the alpha-naphthol and the beta-naphthol on the potential oscillation spectrum of the distinguishing solution.
Alpha-naphthol and beta-naphthol are useful in distinguishing between solutions (chemistryOscillating system) of a distinguishable concentration range of 2.5 x 10 -6 -1×10 -5 mol/L。
The concentration range which can be distinguished by the solution to be distinguished is the optimal concentration range which is determined through experiments. In the concentration range, the influence difference of the alpha-naphthol and the beta-naphthol on the distinguishing solution is obvious, so that the method is easy to observe and analyze and easy to distinguish. In addition, the concentration ranges of the components in the discrimination solution (chemical oscillation system) are shown in table 1, and the optimal solution of the discrimination solution (chemical oscillation system) obtained through a plurality of experiments is shown in table 2:
table 1: concentration ranges of the components in the chemical oscillation system
| Sulfuric acid (mol/L) | Potassium iodate (mol/L) | [NiL](ClO 4 ) 2 (mol/L) | Malonic acid (mol/L) | Hydrogen peroxide (mol/L) |
| 0.0246468-0.025 | 0.0175-0.021 | 6.4875×10 -4 -8.65×10 -4 | 0.125-0.165 | 1.35-1.52 |
Table 2: optimal concentration of each component in chemical oscillation system
| Sulfuric acid (mol/L) | Potassium iodate (mol/L) | [NiL](ClO 4 ) 2 (mol/L) | Malonic acid (mol/L) | Hydrogen peroxide (mol/L) |
| 0.025 | 0.01855 | 8.65×10 -4 | 0.15 | 1.5 |
The specific experimental steps are as follows:
1. preparing a distinguishing solution according to the concentration range specified in Table 1, inserting a prepared working electrode (platinum electrode) and a reference electrode (calomel electrode) into the solution, connecting the other end of the working electrode to a data acquisition device (Go | LINK) through an amplifier (Instrument Amplifier), connecting the working electrode to a computer, opening a log lite program in the computer to set the acquisition time and the sampling speed, and then rapidly clicking a start key to monitor the potential of the solution, so as to obtain an acquired E-t curve (curve of potential value changing with time), namely a chemical potential oscillation map (at the moment, a sample to be tested is not added) to serve as a blank. And (3) respectively and rapidly adding the solutions of the samples to be distinguished into two groups of distinguishing solutions with the same concentration as each component in the blank control experiment at any stable potential minimum point generated by oscillation, and realizing qualitative analysis of the samples to be distinguished according to different oscillation responses of the samples to be distinguished to a chemical oscillation system. The method comprises the following steps: if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a longer period of restraining time, the added sample to be distinguished is alpha-naphthol; if the chemical oscillation is restrained after the solution to be distinguished is added, the oscillation is recovered after a short period of restraining time, and then the added sample to be distinguished is beta-naphthol.
Basic parameters of the chemical potential oscillation spectrum include:
oscillation amplitude: the difference in potential between one lowest potential and the next highest potential during oscillation.
Oscillation period: the time required to go from one lowest (high) potential to the next lowest (high) potential during oscillation.
Highest potential: the highest potential point appears in the system during stable oscillation.
Lowest potential: the lowest potential point of the system appears when the oscillation is stabilized.
Time of inhibition (t) in ): the time required for oscillation to resume is from the time when oscillation is suppressed after the liquid to be measured is added.
Oscillation life: the time from the start to the end of the oscillation during the oscillation.
Drawings
FIG. 1 is an oscillation pattern of a discrimination solution (chemical oscillation system) in example 1 when a sample to be discriminated is not added.
FIG. 2 is a diagram of example 1, incorporating 2.5X10 -6 After mol/L alpha-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
FIG. 3 is a diagram of example 1, incorporating 2.5X10 -6 And after the mol/L beta-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
FIG. 4 is a diagram showing the oscillation pattern of the discrimination solution (chemical oscillation system) in example 2 when the sample to be discriminated is not added.
FIG. 5 is a diagram of example 2 incorporating 5X 10 -6 After mol/L alpha-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
FIG. 6 is a 5X 10 addition in example 2 -6 And after the mol/L beta-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
FIG. 7 is a diagram showing the oscillation pattern of the discrimination solution (chemical oscillation system) in example 3 when the sample to be discriminated is not added.
FIG. 8 is a schematic diagram of example 3, incorporating 1X 10 -5 After mol/L alpha-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
FIG. 9 is a schematic diagram of example 3, incorporating 1X 10 -5 And after the mol/L beta-naphthol, an oscillation response spectrum is obtained by a chemical oscillation system.
Detailed Description
Example 1:
the feasibility of the method for distinguishing alpha-naphthol from beta-naphthol according to the invention was verified in this example as follows:
(1) Preparing a solution
Firstly, preparing 0.025mol/L sulfuric acid as stock solution by using 98% concentrated sulfuric acid and distilled water, then respectively preparing 0.14mol/L potassium iodate solution and 0.0173mol/L [ NiL ] by using 0.025mol/L sulfuric acid solution](ClO 4 ) 2 Solution, 2mol/L malonic acid solution and 4mol/L hydrogen peroxide solution. Into a 50mL small beaker were successively added 14.7mL of a 0.025mol/L sulfuric acid solution, 5.3mL of a 0.14mol/L potassium iodate solution, 2.0mL of a 0.0173mol/L [ NiL ]](ClO 4 ) 2 Solution, 3mL of 2mol/L malonic acid solution and 15.0mL of 4mol/L hydrogen peroxide solution to ensure "H 2 SO 4 - KIO 3 - [NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 "the concentration of each component in the chemical oscillation system is sulfuric acid 0.025mol/L, potassium iodate 0.01855mol/L, [ NiL ]](ClO 4 ) 2 8.65×10 -4 mol/L, malonic acid 0.15mol/L and hydrogen peroxide 1.5mol/L;
simultaneously ethanol is used as a solvent to prepare an alpha-naphthol solution and a beta-naphthol solution with the mol/L of 0.002 respectively.
(2) Oscillation pattern
The potential oscillation pattern of the chemical oscillation system was recorded by a computer equipped with a log lite program, and FIG. 1 shows the potential oscillation pattern of the chemical oscillation system at a typical concentration (sulfuric acid 0.025mmol/L, potassium iodate 0.01855mol/L, [ NiL ]](ClO 4 ) 2 8.65×10 -4 mol/L, 0.15mol/L malonic acid and 1.5mol/L hydrogen peroxide), and the oscillation pattern of the sample to be detected is not added into the distinguishing solution, so as to serve as a blank control. To two sets of discrimination solutions each having the same concentration as the above concentration, 50. Mu.L of 0.002mol/L of alpha-naphthol and beta-naphthol were added, respectively, so that the concentrations thereof in the discrimination solutions were 2.5X10 -6 The mol/L, the time of each addition is at the 6 th potential lowest point of the oscillation spectrum, and the obtained oscillation response spectrum is shown in figure 2 and figure 3 respectively.
(3) Differentiation of
Beta-naphthol as an alpha-naphthol and an isomer thereof has different effects on a chemical oscillation system due to different spatial structures. Comparing FIG. 2 and FIG. 3, it can be seen that the addition of alpha-naphthol results in the suppression of chemical oscillations and the recovery of oscillations after a longer period of suppression time; the addition of beta-naphthol suppresses the chemical oscillation and resumes the oscillation after a short period of suppression. From the above experiments, it is known that the distinction between alpha-naphthol and beta-naphthol can be achieved by comparing the variation of the oscillation patterns.
Taking two solutions (one is alpha-naphthol solution and the other is beta-naphthol solution, but the two solutions are not distinguished) of samples to be distinguished, which are prepared in advance, and marking one of the solutions as a sample 1 and the other as a sample 2;
preparing two groups of chemical oscillation solutions with the same concentration of each component as the concentration, respectively collecting corresponding oscillation patterns, and respectively adding 50 mu L of sample 1 and sample 2 with 0.002mol/L at the lowest point of 7 th potential to ensure that the concentration of each component in the distinguishing solution is 2.5X10 -6 mol/L。
Analysis and comparison show that: the addition of sample 1 suppressed the chemical oscillation and recovered the oscillation after a longer period of time (oscillation pattern corresponding to fig. 2, not corresponding to fig. 3), while the addition of sample 2 suppressed the chemical oscillation and recovered the oscillation after a shorter period of time (oscillation pattern corresponding to fig. 3, not corresponding to fig. 2). Thus, sample 1 is an α -naphthol solution and sample 2 is a β -naphthol solution, thereby achieving a distinction between α -naphthol solution and β -naphthol solution.
Example 2:
the feasibility of the method for distinguishing alpha-naphthol from beta-naphthol according to the invention was verified in this example as follows:
(1) Preparing a solution
Firstly, preparing 0.025mol/L sulfuric acid as stock solution by using 98% concentrated sulfuric acid, then respectively preparing 0.14mol/L potassium iodate solution and 0.0173mol/L [ NiL ] by using 0.025mol/L sulfuric acid solution](ClO 4 ) 2 Solution, 2mol/L malonic acid solution and 4mol/L hydrogen peroxide solution; into a 50mL small beaker were added sequentially 15.0mL of 0.025mol/L sulfuric acid solution, 5.3mL of 0.14mol/L potassium iodate solution, 2mL of 0.0173mol/L [ NiL ]](ClO 4 ) 2 Solution, 2.7mL of 2mol/L malonic acid solution, 15mL of 4mol/L hydrogen peroxide solution to ensure "H 2 SO 4 - KIO 3 - [NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 "the concentration of each component in the chemical oscillation system is sulfuric acid 0.025mol/L, potassium iodate 0.01855mol/L, [ NiL ]](ClO 4 ) 2 8.65×10 -4 mol/L, malonic acid 0.135mol/L and hydrogen peroxide 1.5mol/L;
simultaneously ethanol is used as a solvent to prepare an alpha-naphthol solution and a beta-naphthol solution with the mol/L of 0.002 respectively.
(2) Oscillation pattern
The potential oscillation spectrum of the chemical oscillation system is recorded by a computer with a log lite program, and the difference between oscillation responses generated by alpha-naphthol and beta-naphthol is inspected. FIG. 4 is a graph showing oscillation patterns when the solution was not added to the test sample, and used as a blank. Adding 100 mu L of 0.002mol/L alpha-naphthol solution and beta-naphthol solution into two groups of distinguishing solutions with the concentration of each component being the same as that of the distinguishing solution, so that the concentration of the distinguishing solution is 5 multiplied by 10 -6 The mol/L, the time of each addition is at the 6 th potential lowest point of the oscillation spectrum, and the obtained oscillation response spectrums are respectively shown in fig. 5 and 6.
(3) Differentiation of
Beta-naphthol as an alpha-naphthol and an isomer thereof has different effects on a chemical oscillation system due to different spatial structures. Comparing FIG. 5 and FIG. 6, it can be seen that the addition of alpha-naphthol results in the suppression of chemical oscillations and the recovery of oscillations after a longer period of suppression time; the addition of beta-naphthol suppresses the chemical oscillation and resumes the oscillation after a short period of suppression. From the above experiments, it is known that the distinction between alpha-naphthol and beta-naphthol can be achieved by comparing the variation of the oscillation patterns.
Taking two solutions (one is alpha-naphthol solution and the other is beta-naphthol solution, but the two solutions are not distinguished) of samples to be distinguished, which are prepared in advance, and marking one of the solutions as a sample 1 and the other as a sample 2;
preparing two groups of chemical oscillation solutions with the concentration of each component being the same as that of the solution, respectively collecting corresponding oscillation patterns, and respectively adding 100 mu L of 0.002mol/L of sample 1 and sample 2 at the 6 th potential minimum point to ensure that the concentration of the sample 1 and the sample 2 in the distinguishing solution is 5 multiplied by 10 -6 mol/L。
Analysis and comparison show that: the addition of sample 1 suppressed the chemical oscillation and recovered the oscillation after a longer period of time (oscillation pattern corresponding to fig. 5, not corresponding to fig. 6), while the addition of sample 2 suppressed the chemical oscillation and recovered the oscillation after a shorter period of time (oscillation pattern corresponding to fig. 6, not corresponding to fig. 5). Thus, sample 1 is an α -naphthol solution and sample 2 is a β -naphthol solution, thereby achieving a distinction between α -naphthol solution and β -naphthol solution.
Example 3:
the feasibility of the method for distinguishing alpha-naphthol from beta-naphthol according to the invention is verified according to the following steps:
(1) Preparing a solution
Firstly, preparing 0.025mol/L sulfuric acid as stock solution by using 98% concentrated sulfuric acid and distilled water, then respectively preparing 0.14mol/L potassium iodate solution and 0.0173mol/L [ NiL ] by using 0.025mol/L sulfuric acid solution](ClO 4 ) 2 Solution, 2mol/L malonic acid solution and 4mol/L hydrogen peroxide solution. 15mL of 0.025mol/L sulfur were added sequentially to a 50mL small beakerAcid solution, 5mL of 0.14mol/L potassium iodate solution, 1.8mL of 0.0173mol/L [ NiL](ClO 4 ) 2 Solution, 3.0mL of 2mol/L malonic acid solution and 15.2mL of 4mol/L hydrogen peroxide solution to ensure "H 2 SO 4 - KIO 3 - [NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 The concentration of each component in the chemical oscillation system is sulfuric acid 0.025mol/L, potassium iodate 0.0175mol/L, [ NiL ]](ClO 4 ) 2 7.785×10 -4 mol/L, malonic acid 0.15mol/L and hydrogen peroxide 1.52mol/L;
simultaneously ethanol is used as a solvent to prepare an alpha-naphthol solution and a beta-naphthol solution with the mol/L of 0.002 respectively.
(2) Oscillation pattern
The potential oscillation pattern of the chemical oscillation system was recorded by a computer equipped with a log lite program, and FIG. 7 is the oscillation pattern of the above-mentioned discrimination solution without the test sample added, as a blank. 200. Mu.L of 0.002mol/L alpha-naphthol solution and beta-naphthol solution were added to two sets of discrimination solutions each having the same concentration as the above-mentioned concentration, respectively, so that the concentrations thereof in the discrimination solutions were 1X 10 -5 The mol/L, the time of each addition is at the 6 th potential lowest point of the oscillation spectrum, and the obtained oscillation response spectrums are respectively shown in fig. 8 and 9.
(3) Differentiation of
Beta-naphthol as an alpha-naphthol and an isomer thereof has different effects on a chemical oscillation system due to different spatial structures. Comparing FIG. 8 and FIG. 9, it can be seen that the addition of alpha-naphthol results in the suppression of chemical oscillations and the recovery of oscillations after a longer period of suppression time; the addition of beta-naphthol suppresses the chemical oscillation and resumes the oscillation after a short period of suppression. From the above experiments, it is known that the distinction between alpha-naphthol and beta-naphthol can be achieved by comparing the variation of the oscillation patterns.
Taking two solutions (one is alpha-naphthol solution and the other is beta-naphthol solution, but the two solutions are not distinguished) of samples to be distinguished, which are prepared in advance, and marking one of the solutions as a sample 1 and the other as a sample 2;
preparing two groups of chemical oscillation solutions with the concentration of each component being the same as that of the solution, respectively collecting corresponding oscillation patterns, and respectively adding 200 mu L of sample 1 and sample 2 with the concentration of 0.002mol/L at the 6 th potential minimum point to ensure that the concentration of the sample 1 and the sample 2 in the distinguishing solution is 1 multiplied by 10 -5 mol/L。
Analysis and comparison show that: the addition of sample 1 suppressed the chemical oscillation and recovered the oscillation after a longer period of time (oscillation pattern corresponding to fig. 8, not corresponding to fig. 9), while the addition of sample 2 suppressed the chemical oscillation and recovered the oscillation after a shorter period of time (oscillation pattern corresponding to fig. 9, not corresponding to fig. 8). Thus, sample 1 is an α -naphthol solution and sample 2 is a β -naphthol solution, thereby achieving a distinction between α -naphthol solution and β -naphthol solution.
From the examples above, it can be seen that smaller or larger concentrations of alpha-naphthol solution and beta-naphthol solution can also be distinguished by the process of the invention.
Claims (3)
1. A method for distinguishing alpha-naphthol and isomer beta-naphthol thereof is characterized in that:
ethanol is used as a solvent to prepare a solution of a sample to be distinguished;
application "H 2 SO 4 -KIO 3 -[NiL](ClO 4 ) 2 Malonic acid-H 2 O 2 The chemical oscillation system is used as a distinguishing solution, the potential oscillation map of the change of the potential of the chemical oscillation system along with time is recorded, and the solutions of the alpha-naphthol or the beta-naphthol of the sample to be distinguished are respectively added into the two groups of distinguishing solutions at any one of the 3 rd to 25 th potential minimum points generated by oscillation, so that the distinction of the sample to be distinguished is realized according to different influences of the sample to be distinguished on the chemical oscillation system: if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a longer period of restraining time, the added sample to be distinguished is alpha-naphthol; if chemical oscillation is restrained after the solution to be distinguished is added, and oscillation is recovered after a short period of restraining time, the added sample to be distinguished is beta-naphthol;
[NiL](ClO 4 ) 2 wherein L is 5,7,7,12,14,14-hexamethyl-1, 4,8, 11-tetraazacyclotetradec-4, 11-diene; the molar concentrations of the components in the distinguishing solution are: 0.0246468-0.025mol/L sulfuric acid, 0.0175-0.021mol/L potassium iodate, [ NiL ]](ClO 4 ) 2 6.4875×10 -4 -8.65×10 -4 mol/L, 0.125-0.165mol/L malonic acid and 1.35-1.52mol/L hydrogen peroxide.
2. The method according to claim 1, characterized in that: the molar concentration of each component in the solution was determined to be 0.025mol/L of sulfuric acid, 0.01855mol/L of potassium iodate, [ NiL ]](ClO 4 ) 2 8.65×10 -4 mol/L, malonic acid 0.15mol/L and hydrogen peroxide 1.5mol/L.
3. The method according to claim 1, characterized in that: the distinguishable concentration range of the sample to be distinguished in the distinguishing solution is 2.5×10 -6 -1×10 -5 mol/L。
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