CN105044061A - High-selectivity method for detecting p-phenylenediamine in aqueous solution - Google Patents
High-selectivity method for detecting p-phenylenediamine in aqueous solution Download PDFInfo
- Publication number
- CN105044061A CN105044061A CN201510464161.0A CN201510464161A CN105044061A CN 105044061 A CN105044061 A CN 105044061A CN 201510464161 A CN201510464161 A CN 201510464161A CN 105044061 A CN105044061 A CN 105044061A
- Authority
- CN
- China
- Prior art keywords
- phenylenediamine
- ppd
- aqueous solution
- ethanol
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
The invention discloses a method for identifying p-phenylenediamine in an aqueous solution by using aggregation-induced enhanced emission mechanism. According to the method, by using the facts that salicylaldehyde and p-phenylenediamine can compound N, N'-bis (salicylidene)-p-phenylenediamine Schiff base having an aggregation-induced enhanced emission phenomenon, namely, the N, N'-bis (salicylidene)-p-phenylenediamine Schiff base is non-fluorescent or has relatively weak fluorescence in a good solvent (such as, ethyl alcohol), and has enhanced fluorescence in a poor solvent (such as, water), the in situ test for neutral molecules is achieved, and a novel method for detecting p-phenylenediamine in the aqueous solution is provided. The method is easy and efficient, and p-phenylenediamine can be detected from a mixture of isomerides such as o-phenylenediamine and m-phenylenediamine while the other two isomerides are not detected.
Description
Technical field
The present invention relates to reagent detection field, be specially a kind of method that high selectivity detects p-phenylenediamine (PPD) in aqueous solution.
Background technology
P-phenylenediamine (PPD) is as a kind of important industrial chemicals, be typically used as the synthesis of hair dye, but because it has strong sensitization to human body, and the strong oxidation product of the nucleophilicity that acts on DNA phase can be formed and improve cell carcinogenesis probability in human body, therefore, p-phenylenediamine (PPD) by internationally recognized be carcinogenic substance.Sewage that random discharge contains p-phenylenediamine (PPD) is severe contamination environment not only, also endangers the health of the mankind.The main measurement method of current p-phenylenediamine (PPD) has the methods such as square wave stripping voltammetry, vapor-phase chromatography and liquid phase chromatography, these detection methods not only complicated operation and also cost high.Adopt above detection method in addition, p-phenylenediamine (PPD) can not be distinguished from o-phenylenediamine and these isomerss of m-phenylene diamine.
Summary of the invention
The technical problem to be solved in the present invention overcomes existing p-phenylenediamine (PPD) detection method all complicated operation and high defects of cost, provides a kind of high selectivity to detect the detection method of p-phenylenediamine (PPD) in aqueous solution.
In order to solve the problems of the technologies described above, the invention provides following technical scheme:
High selectivity detects a method for p-phenylenediamine (PPD) in aqueous solution, comprises following step:
1), in the round-bottomed flask of 50mL, solvent 20 ~ 30mL is added;
2), in round-bottomed flask add salicylide 8 ~ 15mmol, add thermal agitation and salicylide is dissolved completely;
3), in round-bottomed flask, solution 3 ~ 5mmol to be measured is added; Stir, ambient temperatare puts 30 ~ 40 minutes;
4), stir after, take out 2mL solution, under 400nm excitation wavelength, carry out fluorescence spectrometry.
Further, step 1) in solvent be the mixed liquor of ethanol, acetic acid and water three, the volume ratio of preferred ethanol, acetic acid and water three is ethanol: acetic acid: water=5: 1: 19.
Further, step 4) in fluorescence spectrometry in the damping fluid that uses be pH=7.0 HEPES buffering is molten.
The present invention utilizes gathering Fluorescence Increasing mechanism to identify p-phenylenediamine (PPD) in aqueous, achieving centering molecule in situ detection, providing a kind of new method for detecting p-phenylenediamine (PPD) in aqueous.The method is simply efficient, and p-phenylenediamine (PPD) can be detected from the potpourri of o-phenylenediamine and these isomerss of m-phenylene diamine, and other two kinds of isomerss are not detected.
Accompanying drawing explanation
Accompanying drawing is used to provide a further understanding of the present invention, and forms a part for instructions, together with embodiments of the present invention for explaining the present invention, is not construed as limiting the invention.In the accompanying drawings:
Fig. 1 is the synthetic route chart of double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases;
Fig. 2 is the fluorescence emission spectrum of double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases in ethanol-water mixed solvent;
Fig. 3 is o-phenylenediamine, m-phenylene diamine and p-phenylenediamine (PPD) three kinds of phenylenediamines and the reacted change in fluorescence figure of salicylide.
Embodiment
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described, should be appreciated that preferred embodiment described herein is only for instruction and explanation of the present invention, is not intended to limit the present invention.
Embodiment
High selectivity detects a method for p-phenylenediamine (PPD) in aqueous solution, comprises following step:
1), in the round-bottomed flask of 50mL, add the mixed solvent 20 ~ 30mL of ethanol, acetic acid and water three, the volume ratio of ethanol, acetic acid and water three is ethanol: acetic acid: water=5: 1: 19;
2), in round-bottomed flask add salicylide 8 ~ 15mmol, add thermal agitation and salicylide is dissolved completely;
3), in round-bottomed flask, solution 3 ~ 5mmol to be measured is added; Stir, ambient temperatare puts 30 ~ 40 minutes;
4), stir after, take out 2mL solution, under 400nm excitation wavelength, carry out fluorescence spectrometry, damping fluid is that the HEPES buffering of pH=7.0 is molten.
Whether strengthened by fluorescence spectrometry fluorescence intensity, whether can judge in solution to be measured containing p-phenylenediamine (PPD).
Salicylide and p-phenylenediamine (PPD) can synthesize double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases, as shown in Figure 1;
Use ethanol-water mixed solvent, 10 μMs of double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases to be increased in the neutral buffered aqueous solution (10mMHEPES, pH value is 7.0) of 90% by 10% gradually at volume fraction of ethanol carries out probing into of gathering Fluorescence Increasing character.Double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases is fluorescence emission spectrum in different volumes fractional content ethanol/water mixing buffer solution, is that in the 10mMHEPES aqueous buffer solution of 7.0, excitation wavelength is 400nm in pH value.
As seen from Figure 2, double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases has gathering Enhancement of Fluorescence, namely in the good solvent (such as ethanol) unstressed configuration or fluorescence more weak, and in poor solvent (such as water) Fluorescence Increasing.This may be because double salicylaldehyde contracting p-phenylenediamine (PPD) schiff bases two amino are distant, spatially be conducive to making salicylide hydroxyl form intramolecular hydrogen bond with contiguous nitrogen-atoms, thus phenolic hydroxyl group and carbon-nitrogen double bond are fixed in stable " hexatomic ring " structure, fluorescence obviously strengthens.
Salicylide 2mM and each 0.5PPM of o-phenylenediamine, m-phenylene diamine and p-phenylenediamine (PPD) is added under ethanol, acetic acid, water mixed solvent condition (v: v: v=5: 1: 19) in 50mL round-bottomed flask, after room temperature is placed 30 minutes, take out 2mL wherein, carry out fluorescence spectrometry, excitation wavelength is 400nm.
As seen from Figure 3, under same test condition, o-phenylenediamine, ask phenylenediamine and p-phenylenediamine (PPD) 0.5PPM tri-kinds of phenylenediamines, only have p-phenylenediamine (PPD) to be detected after adding salicylide, therefore the method can be used for identification and the detection of p-phenylenediamine (PPD) in aqueous solution.And p-phenylenediamine (PPD) significantly strengthens with fluorescence after salicylide reaction, fluorescence intensity almost adds 800 times, and o-phenylenediamine, m-phenylene diamine add salicylide after fluorescence intensity there is no significant change, therefore the method can be used for effective detection of p-phenylenediamine (PPD) in aqueous solution.
Last it is noted that the foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, although with reference to previous embodiment to invention has been detailed description, for a person skilled in the art, it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein portion of techniques feature.Within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (4)
1. high selectivity detects a method for p-phenylenediamine (PPD) in aqueous solution, it is characterized in that, comprises following step:
1), in the round-bottomed flask of 50mL, solvent 20 ~ 30mL is added;
2), in round-bottomed flask add salicylide 8 ~ 15mmol, add thermal agitation and salicylide is dissolved completely;
3), in round-bottomed flask, solution 3 ~ 5mmol to be measured is added; Stir, ambient temperatare puts 30 ~ 40 minutes;
4), stir after, take out 2mL solution, under 400nm excitation wavelength, carry out fluorescence spectrometry.
2. a kind of high selectivity as claimed in claim 1 detects the method for p-phenylenediamine (PPD) in aqueous solution, it is characterized in that, described step 1) in solvent be the mixed liquor of ethanol, acetic acid and water three.
3. a kind of high selectivity as claimed in claim 2 detects the method for p-phenylenediamine (PPD) in aqueous solution, it is characterized in that, described step 1) in solvent be ethanol, the volume ratio of acetic acid and water three is ethanol: acetic acid: water=5: 1: 19.
4. a kind of high selectivity as claimed in claim 1 detects the method for p-phenylenediamine (PPD) in aqueous solution, it is characterized in that, described step 4) in fluorescence spectrometry in the damping fluid that uses be pH=7.0 HEPES buffering is molten.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510464161.0A CN105044061A (en) | 2015-07-25 | 2015-07-25 | High-selectivity method for detecting p-phenylenediamine in aqueous solution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510464161.0A CN105044061A (en) | 2015-07-25 | 2015-07-25 | High-selectivity method for detecting p-phenylenediamine in aqueous solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105044061A true CN105044061A (en) | 2015-11-11 |
Family
ID=54450774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510464161.0A Pending CN105044061A (en) | 2015-07-25 | 2015-07-25 | High-selectivity method for detecting p-phenylenediamine in aqueous solution |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105044061A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110530834A (en) * | 2019-08-28 | 2019-12-03 | 西南交通大学 | A method of rapidly and efficiently detecting trace p-phenylenediamine |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102721674A (en) * | 2012-05-24 | 2012-10-10 | 北京化工大学 | Quaternary fluorescence enhancement system of Eu-vanillin type Schiff base-phenanthroline-Zn, preparation method and application |
| CN102735662A (en) * | 2012-07-19 | 2012-10-17 | 贵州大学 | High sensitivity and high selectivity fluorescence emission spectrum analysis method for zinc ions |
| CN103254149A (en) * | 2013-05-07 | 2013-08-21 | 山西大学 | Aminonaphthol Schiff base compound and preparation method and application thereof |
| CN103320118A (en) * | 2013-05-08 | 2013-09-25 | 济南大学 | Schiff base cooper ion fluorescence probe and preparation method thereof |
| CN104193706A (en) * | 2014-04-30 | 2014-12-10 | 西北师范大学 | 1,5-diaminonaphthalene bilateral Schiff base, preparation thereof and applications of the 1,5-diaminonaphthalene bilateral Schiff base as acceptor molecule in mercury ion detection |
| CN104311450A (en) * | 2014-09-23 | 2015-01-28 | 西北师范大学 | Bis-schiff base sensor capable of circulation monitoring of copper ions, synthesis and applications thereof |
-
2015
- 2015-07-25 CN CN201510464161.0A patent/CN105044061A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102721674A (en) * | 2012-05-24 | 2012-10-10 | 北京化工大学 | Quaternary fluorescence enhancement system of Eu-vanillin type Schiff base-phenanthroline-Zn, preparation method and application |
| CN102735662A (en) * | 2012-07-19 | 2012-10-17 | 贵州大学 | High sensitivity and high selectivity fluorescence emission spectrum analysis method for zinc ions |
| CN103254149A (en) * | 2013-05-07 | 2013-08-21 | 山西大学 | Aminonaphthol Schiff base compound and preparation method and application thereof |
| CN103320118A (en) * | 2013-05-08 | 2013-09-25 | 济南大学 | Schiff base cooper ion fluorescence probe and preparation method thereof |
| CN104193706A (en) * | 2014-04-30 | 2014-12-10 | 西北师范大学 | 1,5-diaminonaphthalene bilateral Schiff base, preparation thereof and applications of the 1,5-diaminonaphthalene bilateral Schiff base as acceptor molecule in mercury ion detection |
| CN104311450A (en) * | 2014-09-23 | 2015-01-28 | 西北师范大学 | Bis-schiff base sensor capable of circulation monitoring of copper ions, synthesis and applications thereof |
Non-Patent Citations (1)
| Title |
|---|
| 边延江等: "三种席夫碱聚集荧光增强性质及构效关系的研究", 《化学研究与应用》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110530834A (en) * | 2019-08-28 | 2019-12-03 | 西南交通大学 | A method of rapidly and efficiently detecting trace p-phenylenediamine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Ratiometric fluorescence probe for hydrazine vapor detection and biological imaging | |
| Bruemmer et al. | Development of a general aza-cope reaction trigger applied to fluorescence imaging of formaldehyde in living cells | |
| Nguyen et al. | Recent progress in the development of fluorescent probes for hydrazine | |
| Manna et al. | Recent developments in fluorometric and colorimetric chemodosimeters targeted towards hydrazine sensing: present success and future possibilities | |
| Yu et al. | A novel benzothiazole-based fluorescent probe for cysteine detection and its application on test paper and in living cells | |
| Cao et al. | A fluorescent probe for distinguish detection of formaldehyde and acetaldehyde | |
| CN109232444A (en) | A kind of camphor base fluorescent probe and preparation method thereof for detecting hydrazine | |
| CN105295899B (en) | Ratiometric fluorescent probe for detecting hydrogen sulfide and application of ratiometric fluorescent probe | |
| Wei et al. | A two-step responsive colorimetric probe for fast detection of formaldehyde in weakly acidic environment | |
| Bao et al. | Selective colorimetric sensing for F− by a cleft-shaped anion receptor containing amide and hydroxyl as recognition units | |
| CN109867611A (en) | A kind of for red wine and in vivo water-soluble two-photon hydrogen sulfide fluorescence probe and its preparation method and application of sulfurated hydrogen detection | |
| CN107033158B (en) | A kind of colorimetric fluorescence probe and preparation method thereof of hypersensitive analysis mercury ion | |
| CN107814808A (en) | A kind of near-infrared response type two-photon fluorescence probe and its preparation method and application | |
| CN106565721A (en) | Fluorescent reagent for selectively recognizing lysine and methionine and recognition application thereof | |
| CN107417671A (en) | A kind of coumarin derivative of the substitution containing quinoline and preparation method thereof and the application on Ratio-type pH fluorescence probes | |
| CN110669026B (en) | Fluorescent probe molecule for detecting nitrite and preparation method thereof | |
| CN107098915A (en) | A kind of response type fluorescence probe for distinguishing sulfhydryl compound and its synthetic method and application | |
| CN107266397B (en) | A kind of preparation and application of thiocarbamates hypochlorous acid fluorescence probe | |
| CN108658838A (en) | A kind of formaldehyde fluorescence probe based on seven methine indoles cyanines and preparation method thereof and application method | |
| CN107353300A (en) | A kind of preparation and application of phenylboronic acid hypochlorous acid colorimetric fluorescence probe | |
| CN105400508A (en) | Method for detecting concentration of hydrazine | |
| He et al. | Highly enantioselective fluorescent sensor for chiral recognition of amino acid derivatives | |
| CN105044061A (en) | High-selectivity method for detecting p-phenylenediamine in aqueous solution | |
| CN106967038B (en) | A kind of synthesis and application of the fluorescence probe of Dual channel detection hydrogen sulfide | |
| CN105038765B (en) | A kind of preparation method and applications with AIEE property high selectivity cryanide ion fluorescence probes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20151111 |
|
| RJ01 | Rejection of invention patent application after publication |