CN110066242B - Compound for detecting p-phenylenediamine and preparation method thereof - Google Patents
Compound for detecting p-phenylenediamine and preparation method thereof Download PDFInfo
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- CN110066242B CN110066242B CN201811104022.7A CN201811104022A CN110066242B CN 110066242 B CN110066242 B CN 110066242B CN 201811104022 A CN201811104022 A CN 201811104022A CN 110066242 B CN110066242 B CN 110066242B
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- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 title claims abstract description 61
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- 238000002360 preparation method Methods 0.000 title description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- -1 4-formyl isonicotinic acid phenyl ester Chemical compound 0.000 claims abstract description 27
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- 238000009210 therapy by ultrasound Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 abstract description 15
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- 239000012043 crude product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 6
- 238000000527 sonication Methods 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
- 239000000118 hair dye Substances 0.000 description 4
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- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 4
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- 206010028980 Neoplasm Diseases 0.000 description 3
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- 238000005375 photometry Methods 0.000 description 3
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- 238000001291 vacuum drying Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
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- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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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
- G01N21/75—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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Abstract
The invention discloses a compound for detecting p-phenylenediamine, which has the chemical name of 4-formyl isonicotinic acid phenyl ester and has the chemical formula C13H9NO3. The compound is added into a methanol solution containing p-phenylenediamine, the solution is changed from colorless to orange yellow, the p-phenylenediamine can be rapidly detected through visual observation, the p-phenylenediamine can be rapidly, conveniently and selectively identified, and the compound can be used as a p-phenylenediamine detection reagent to detect whether the liquid contains the p-phenylenediamine.
Description
Technical Field
The invention belongs to the technical field of chemical detection, and relates to an organic compound capable of quickly identifying p-phenylenediamine and application of the compound in qualitative detection of the p-phenylenediamine.
Background
P-phenylenediamine is one of the simplest aromatic diamines, has certain water solubility, can be dissolved in methanol or ethanol and the like, and has wide application in the chemical field. For example, as a raw material for synthesizing p-phenylenediamine-based rubber antioxidants; the product is used as an intermediate for synthesizing high-crystallinity temperature-resistant polyurethane, aromatic polyamide fabric and other polymers; are also commonly used as the primary raw materials for the manufacture of azo dyes and sulfur fuels. With the rapid development of the chemical industry and the large amount of p-phenylenediamine, the demand of the p-phenylenediamine is increasing at home and abroad, and meanwhile, the process of producing and applying the p-phenylenediamine also generates a large amount of industrial waste liquid containing the p-phenylenediamine.
P-phenylenediamine is also often used by unskilled vendors to produce poor quality blacking hair dyes, such as the various "one-wash-and-black" shampoos sold in the market, which are actually hair dyes, and most of them are supplemented with chemicals such as p-phenylenediamine, but are fraudulently stained with herbal extracts, safe and healthy hair.
Animal experiments show that the p-phenylenediamine compounds can cause cancers of liver, mammary gland, thyroid gland, skin, urinary system or lymphatic system. P-phenylenediamine is also an internationally recognized strong sensitizing substance, has strong sensitization to human bodies, can cause toxic metabolism to deposit in organisms after long-term contact, can cause contact dermatitis and eczema, even can cause tumors, cancers and the like, and is harmful to human health. In addition, p-phenylenediamine is highly toxic to aquatic organisms. Therefore, the discharge of the p-phenylenediamine waste liquid or the use of the p-phenylenediamine-containing hair dye will cause a certain degree of pollution to the environment, and particularly cause serious toxic effects on human bodies. Based on the method, the establishment of the method for simply and quickly detecting the p-phenylenediamine with high sensitivity has very important significance.
At present, the detection method of p-phenylenediamine in waste liquid comprises a diazonium method, a flow injection-photometric analysis method and a repression kinetic photometric method. The diazo salt method is more conventional, and because other aromatic primary amines can also have diazotization reaction, the selectivity is poor, and the operation is complicated because the diazotization reaction is carried out in an ice bath. The flow injection photometry method detects p-phenylenediamine by the formation of a blue dye of p-phenylenediamine and aniline in the presence of potassium persulfate under acidic conditions, wherein the dye has a characteristic absorption peak at a wavelength of 660 mm. The method has strong specificity, requires accurate solution preparation, detection parameter setting and working curve establishment during detection, has relatively complex operation, gradually changes the color of a product within 2 hours, and is difficult to detect by a common photometer. The inhibition kinetics photometry has high measurement precision and accuracy, has specific requirements on reaction temperature, time and the like, also uses instruments such as a spectrophotometer, a constant temperature bath and the like, has complicated operation process and is limited to a certain extent. Based on the method, the research and development of the simple, convenient and effective detection method of p-phenylenediamine with low cost has important significance and wide commercial prospect.
Kaliyappan, t. et al report a compound, phenyl 4-formylisonicotinate (Molecular and Liquid Crystals, 2015, 606, 1-11.), but only with reference to its chemical structure and no study of the use of this compound. In particular, the application research of the method in chemical detection is not involved.
Disclosure of Invention
The invention aims to provide a compound for detecting p-phenylenediamine and a preparation method thereof.
It is another object of the present invention to provide a method for rapidly and directly detecting p-phenylenediamine using the compound.
The chemical name of the compound for detecting p-phenylenediamine is 4-formyl isonicotinic acid phenyl ester, and the chemical formula is C13H9NO3Having the following structural formula:
the preparation method of the compound of the invention comprises the following steps:
the compound is prepared by taking p-hydroxybenzaldehyde, isonicotinoyl chloride hydrochloride and triethylamine as raw materials and reacting in a mixed solvent system of chloroform and methanol.
Specifically, in the preparation method, the reaction temperature is 20-65 ℃.
Further, the reaction time is 24-60 hours.
Furthermore, the volume ratio of the chloroform to the methanol is 1: 0.5-1.5.
Preferably, the molar ratio of the p-hydroxybenzaldehyde to the isonicotinoyl chloride hydrochloride to the triethylamine is 1: 1-2: 1-3.
More specifically, the preparation method of the compound of the invention comprises the following steps: dissolving p-hydroxybenzaldehyde, isonicotinoyl chloride hydrochloride and triethylamine in a mixed solvent of chloroform and methanol, reacting at a reaction temperature, and removing the solvent after the reaction is finished to obtain a crude product of the compound.
A small amount of residual raw materials and by-products remain in the crude product obtained by the above preparation, and it is necessary to refine it.
Furthermore, the invention provides a simple, but not limiting, purification method for the crude compound, which comprises:
and adding the obtained crude product into dichloromethane, heating, refluxing and stirring for 5 minutes, naturally cooling to room temperature, performing suction filtration, and drying the solid in vacuum to obtain the compound.
The compound prepared by the invention can be used for qualitatively detecting p-phenylenediamine.
In particular, the compounds of the present invention can be used to qualitatively detect the presence of p-phenylenediamine in solutions or industrial effluents.
Specifically, the compound can be used for detecting whether industrial production solutions such as rubber anti-aging agents, polymer intermediates, azo dyes, black hair dyes and the like or discharged industrial waste liquids contain p-phenylenediamine or not.
The method for qualitatively detecting p-phenylenediamine by using the compound comprises the following steps:
and concentrating the solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 4-formyl isonicotinic acid phenyl ester is added into a small bottle, heated and ultrasonically treated for 5 minutes, and then the solution is kept stand for 30 minutes to observe whether the solution changes from colorless to orange yellow.
In the qualitative detection method, the detection limit of the p-phenylenediamine is 1wt per thousand. Namely, if the color of the solution to be detected changes from colorless to orange yellow, the content of the p-phenylenediamine in the solution to be detected reaches more than 1 wt%.
Further, in the above-mentioned qualitative determination method, it is preferable that the concentration of 4-formylisonicotinic acid phenyl ester in the solution to be determined is higher than 2mg/mL, as the optimum concentration for observing whether or not the solution is discolored.
The compound of the invention can quickly and simply detect p-phenylenediamine and can simultaneously carry out single selective recognition on the p-phenylenediamine. Organic amines such as octylamine, dodecylamine, hexadecylamine, ethylenediamine, hexamethylenediamine, decamethylenediamine, p-phenylenediamine and the like are selected and detected under the same condition, and the solution is obviously changed from colorless to orange yellow only when the compound meets the p-phenylenediamine.
The compound can be synthesized by one-step reaction, and the preparation process and the post-treatment are very simple. When the method is used for detecting p-phenylenediamine in solution or waste liquid, other detection reagents do not need to be prepared, other large-scale instruments are not needed, the operation is simple and convenient, and the limiting conditions of time, temperature and the like are small. In addition, in the detection process, the color development is fast and stable, and the existence of the p-phenylenediamine can be determined by directly observing the change of the solution color. Factories, enterprises or individuals can complete rapid detection by themselves completely, and the method can be popularized and applied.
Drawings
FIG. 1 is an infrared spectrum of phenyl 4-formylisonicotinate prepared in example 1.
FIG. 2 is a mass spectrum of phenyl 4-formylisonicotinate prepared in example 1.
FIG. 3 shows the methanol-extracted concentrated solutions of octylamine, dodecylamine, hexadecylamine, ethylenediamine, hexamethylenediamine, decamethylenediamine, and p-phenylenediamine.
FIG. 4 is a photograph showing the color reaction of the solution when the compound of the present invention is detected in various organic amines.
Detailed Description
The following examples are only preferred embodiments of the present invention and are not intended to limit the present invention in any way. Various modifications and alterations to this invention will become apparent to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Example 1
1.0g of p-hydroxybenzaldehyde, 2.6g of isonicotinoyl chloride hydrochloride and 2.3g of triethylamine were added to 120mL of a chloroform-methanol mixture (volume ratio: 1) and reacted at 25 ℃ for 48 hours. After the reaction is finished, the solution is dried in vacuum to obtain a crude product. And adding the obtained crude product into dichloromethane, heating, refluxing and stirring for 5 minutes, naturally cooling to room temperature, performing suction filtration, and performing vacuum drying on the solid to obtain the 4-formyl isonicotinic acid phenyl ester.
Fig. 1 is an infrared spectrum of 4-formylisonicotinic acid phenyl ester, wherein characteristic peaks at 3440 in the spectrum are C ═ O stretching vibration (overtone), characteristic peaks at 1730 and 1683 are C ═ O stretching vibration of ester group and aldehyde group respectively, and characteristic peaks at 1256 are C — O — C stretching vibration, which indicates that 4-formylisonicotinic acid phenyl ester is successfully prepared.
FIG. 2 is a mass spectrum of 4-formylisonicotinic acid phenyl ester, wherein the characteristic peak at 249.8 in the mass spectrum is the ion proton peak of the target product added with sodium, and no hetero peak exists in the mass spectrum, which proves that the purity of the prepared 4-formylisonicotinic acid phenyl ester is higher.
Example 2
1.0g of p-hydroxybenzaldehyde, 2.2g of isonicotinoyl chloride hydrochloride and 1.7g of triethylamine were added to 100mL of a chloroform-methanol mixture (volume ratio: 1: 0.5) and reacted at 45 ℃ for 38 hours. After the reaction is finished, the solution is dried in vacuum to obtain a crude product. And adding the obtained crude product into dichloromethane, heating, refluxing and stirring for 5 minutes, naturally cooling to room temperature, performing suction filtration, and performing vacuum drying on the solid to obtain the 4-formyl isonicotinic acid phenyl ester.
Example 3
1.0g of p-hydroxybenzaldehyde, 1.7g of isonicotinoyl chloride hydrochloride and 1.1g of triethylamine were added to 80mL of a chloroform-methanol mixture (volume ratio: 1.5), and the mixture was reacted at 62 ℃ for 25 hours. After the reaction is finished, the solution is dried in vacuum to obtain a crude product. And adding the obtained crude product into dichloromethane, heating, refluxing and stirring for 5 minutes, naturally cooling to room temperature, performing suction filtration, and performing vacuum drying on the solid to obtain the 4-formyl isonicotinic acid phenyl ester.
Application example 1
2mg of p-phenylenediamine was mixed into 100mL of water to prepare a simulated industrial waste stream.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. Adding 3mg of 4-formylisonicotinic acid phenyl ester into a small bottle, heating and carrying out ultrasonic treatment for 5 minutes, standing for 30 minutes, and observing that the solution is changed from colorless to orange yellow, which indicates that the solution to be tested contains p-phenylenediamine.
Application example 2
3mg of p-phenylenediamine was mixed into 100mL of chloroform to prepare a simulated industrial waste.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. Adding 3mg of 4-formylisonicotinic acid phenyl ester into a small bottle, heating and carrying out ultrasonic treatment for 5 minutes, standing for 30 minutes, and observing that the solution is changed from colorless to orange yellow, which indicates that the solution to be tested contains p-phenylenediamine.
Application example 3
A simulated industrial waste stream was prepared by mixing 4mg of p-phenylenediamine with 200mL of ethyl acetate.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 4mg of 4-formylphenyl isonicotinate is added into a small bottle, and after heating and ultrasonic treatment for 5 minutes and standing for 30 minutes, the solution is observed to be changed from colorless to orange yellow, which indicates that the solution to be tested is simulated to contain p-phenylenediamine.
Comparative example 1
A simulated industrial waste stream was prepared by mixing 4mg of octylamine into 100mL of chloroform.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 3mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
Comparative example 2
3mg of dodecylamine was mixed into 100mL of chloroform to prepare a simulated industrial waste.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 3mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
Comparative example 3
3mg of hexadecylamine was mixed into 100mL of chloroform to prepare a simulated industrial waste liquid.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 5mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
Comparative example 4
A simulated industrial waste stream was prepared by mixing 4mg of ethylenediamine into 100mL of chloroform.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 5mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
Comparative example 5
A simulated industrial waste stream was prepared by mixing 5mg of hexamethylenediamine in 100mL of chloroform.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 4mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
Comparative example 6
A simulated industrial waste stream was prepared by mixing 4mg of decamethylenediamine into 100mL of chloroform.
And concentrating the simulated solution to be detected to about 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be detected, uniformly mixing, and transferring 1mL of mixed solution into a small bottle. 4mg of 4-formylphenyl isonicotinate was added to the vial, and after heating and sonication for 5 minutes, and after standing for 30 minutes, the solution was observed to remain colorless, indicating that the simulated test solution contained no p-phenylenediamine.
In FIG. 3, the numbers a to g are vials of methanol-extracted concentrated solutions of p-phenylenediamine, octylamine, dodecylamine, hexadecylamine, ethylenediamine, hexamethylenediamine, and decamethylenediamine in application example 2 and comparative examples 1 to 6, respectively. In FIG. 4, the numbers a to g are vials of application example 2 and comparative examples 1 to 6, respectively.
As can be seen from the figure, the solution in vial No. 4a, i.e. the chloroform solution containing p-phenylenediamine, is obviously changed from colorless to orange yellow, while the color in other vials is basically not changed greatly compared with that before the detection reagent is added, which indicates that the 4-formylisonicotinic acid phenyl ester can be used for simply and conveniently carrying out single identification detection on p-phenylenediamine.
Claims (2)
1. The application of the compound 4-formyl isonicotinic acid phenyl ester in detecting whether the solution contains p-phenylenediamine or not.
2. A method for detecting p-phenylenediamine in a solution by using the compound as claimed in claim 1, which comprises the steps of concentrating the solution to be detected to 1mL by vacuum rotary evaporation, adding 1mL of methanol into the solution to be uniformly mixed, transferring 1mL of mixed solution into a small bottle, adding 4-formylisonicotinic acid phenyl ester into the small bottle, heating and carrying out ultrasonic treatment for 5 minutes, standing for 30 minutes, and converting the colorless solution into orange yellow, namely, the presence of p-phenylenediamine in the detected solution is indicated.
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Citations (2)
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| CN101672794A (en) * | 2009-09-23 | 2010-03-17 | 广东省药品检验所 | Rapid semi-quantitative detection method of phenylenediamine substances |
| CN106706620A (en) * | 2016-12-15 | 2017-05-24 | 厦门海荭兴仪器股份有限公司 | Rapid benzoyl peroxide detection method and kit |
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| CN101672794A (en) * | 2009-09-23 | 2010-03-17 | 广东省药品检验所 | Rapid semi-quantitative detection method of phenylenediamine substances |
| CN106706620A (en) * | 2016-12-15 | 2017-05-24 | 厦门海荭兴仪器股份有限公司 | Rapid benzoyl peroxide detection method and kit |
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