CN110066242A - A kind of compound and preparation method thereof detecting p-phenylenediamine - Google Patents
A kind of compound and preparation method thereof detecting p-phenylenediamine Download PDFInfo
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- CN110066242A CN110066242A CN201811104022.7A CN201811104022A CN110066242A CN 110066242 A CN110066242 A CN 110066242A CN 201811104022 A CN201811104022 A CN 201811104022A CN 110066242 A CN110066242 A CN 110066242A
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- 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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- 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 kind of for detecting the compound of p-phenylenediamine, and the chemical name of the compound is 4- formoxyl isonicotinic acid phenyl ester, chemical formula C13H9NO3.The compound of the present invention is added in the methanol solution containing p-phenylenediamine, solution can by it is colourless be changed into it is orange-yellow, p-phenylenediamine can be quickly detected by naked-eye observation, and can it is quick, convenient, selectively identify p-phenylenediamine, it can be used as p-phenylenediamine detection reagent, whether contain p-phenylenediamine in detecting liquid.
Description
Technical field
The invention belongs to technical field of chemical detection, are related to a kind of organic compound that can quickly identify p-phenylenediamine, with
And the compound is used for the application of qualitative detection p-phenylenediamine.
Background technique
P-phenylenediamine is one of simplest aromatic diamines, has certain water solubility, can be dissolved in methanol or ethyl alcohol etc.,
It is had a wide range of applications in chemical field.For example, being used as the raw material of synthesis p-phenylenediamine rubber aging inhibitor；As the high knot of synthesis
The intermediate of the polymer such as heat resistant polyurethane, the aromatic polyamides fabric of brilliant degree；It is also commonly used for manufacture azo dyes and vulcanization combustion
The primary raw material of material.With the rapid development of chemical industry and a large amount of uses of p-phenylenediamine, the demand of domestic and international p-phenylenediamine
Measure it is growing, while produce and application p-phenylenediamine process also produce industrial wastes largely containing p-phenylenediamine.
P-phenylenediamine also usually is used to produce the dyeing agent of poor quality by wicked business, such as sells in the market more
Kind of " one wash black " shampoo, shows that it is essentially all hair dye by detection, most of to be all added to the chemistry such as p-phenylenediamine
Substance is turned on herbaceous plant essence, safe and healthy camouflage but to cheat consumer.
It is found by animal experiment, oxidation will lead to liver, mammary gland, thyroid gland, skin, urinary system
Or the cancer of lymphatic system.P-phenylenediamine is also internationally recognized strong allergenic substance, has stronger sensitization to human body, for a long time
Contact will lead to toxic metabolic in the intracorporal deposition of machine, contact dermatitis, eczema can be caused, or even cause tumour, cancer etc., danger
Evil human health.In addition, p-phenylenediamine has strong toxicity to aquatic object.Therefore, it discharges the waste liquid of p-phenylenediamine or makes
With the dyeing agent containing p-phenylenediamine, it will cause a degree of pollution to environment, especially generated to human body serious
Toxic action.Based on this, a kind of method for establishing highly sensitive, simple and fast detection p-phenylenediamine has highly important meaning
Justice.
Currently, the detection method of p-phenylenediamine has diazonium salt method, flow injection-analytical photometry, suppresses power in waste liquid
Learn photometry.Diazonium salt method is more conventional, and because diazo-reaction can also occur for other aromatic primary amines, therefore selectivity is poor, simultaneously
It to carry out, operate more complex in ice bath.Flow injection spectrophotometry is then p-phenylenediamine and aniline according under acid condition
Blue dyes is formed in the presence of potassium peroxydisulfate, this dyestuff is detected pair with this in 660mm wavelength existing characteristics absorption peak everywhere
Phenylenediamine.The method specificity is strong, and when detection needs accurate formulation solution, detection parameters are arranged, establish working curve, operates phase
To complexity, and product color gradually changes in 2 hours, and common photometer is difficult to detect.Inhibitory kinetic-spectorophtometry, measurement
Preci-sion and accuracy is higher, has specific requirement to reaction temperature, time etc., while also to use spectrophotometer, perseverance
The instruments such as warm slot, operating process is cumbersome, using being subject to certain restrictions.Based on this, low in cost, simple and effective pair is researched and developed
The detection method of phenylenediamine, is not only of great significance, while also having extensive commercial promise.
Kaliyappan, T. etc. report a kind of compound 4- formoxyl isonicotinic acid phenyl ester (Molecular Crystals
And Liquid Crystals, 2015,606,1-11.), but its chemical structure has been only related to, it is not directed to the application of the compound
Research.Specifically, more it is not directed to its application study in terms of chemical detection.
Summary of the invention
The object of the present invention is to provide it is a kind of detect p-phenylenediamine compound, and preparation method thereof.
The method that the compound is provided for fast direct earthing detection p-phenylenediamine is the second object of the present invention.
Chemical name of the present invention for detecting the compound of p-phenylenediamine is 4- formoxyl isonicotinic acid phenyl ester, is changed
Formula is C13H9NO3, have following structure formula:
Compound of the present invention the preparation method is as follows:
Using parahydroxyben-zaldehyde, different nicotinoyl chloride hydrochloride and triethylamine as raw material, in chloroform and methanol mixed solvent system
Middle reaction is prepared.
Specifically, in above-mentioned preparation method, reaction temperature is 20~65 DEG C.
Further, the reaction time is 24~60 hours.
Further, the volume ratio of the chloroform and methanol is 1: 0.5~1.5.
Preferably, parahydroxyben-zaldehyde, different nicotinoyl chloride hydrochloride, triethylamine mole dosage ratio be 1: 1~2: 1~3.
More specifically, the preparation method of compound of the present invention is: first by parahydroxyben-zaldehyde, different nicotinoyl chloride hydrochloride
It is dissolved in chloroform and methanol mixed solvent with triethylamine, is reacted under reaction temperature, after the reaction was completed, obtained after removing solvent
To the crude product of the compound.
A small amount of surplus stock and by-product are also remained in the above-mentioned crude product being prepared, needs to refine it.
In turn, the present invention purifies the crude product of compound using a kind of simple but infinite method of purification,
Method is as follows:
Obtained crude product is added in methylene chloride, stirring is heated to reflux after five minutes, is naturally cooled to room
Temperature filters, and solid is dried in vacuo to get the compound.
Compound prepared by the present invention can be used for qualitative detection p-phenylenediamine.
Particularly, whether the compound of the present invention can be used in qualitative detection solution or industrial wastes containing to benzene two
Amine.
Specifically, it is black to can be used for detecting rubber anti-ageing agent, intermediate polymer, azo dyes, dye for the compound
Whether contain p-phenylenediamine in the production solution of industry such as hair agent or the industrial wastes of discharge.
The method of compound characterization detection p-phenylenediamine of the present invention is as follows:
Solution vacuum concentrated by rotary evaporation to be detected is arrived into 1mL or so, the methanol of 1mL is added thereto after mixing, is pipetted
1mL mixed liquor is into bottle.4- formoxyl isonicotinic acid phenyl ester is added in bottle, simultaneously ultrasound is heated and after five minutes, stands 30 minutes
Afterwards, whether observation solution from colourless becomes orange-yellow.
In above-mentioned qualitative checking method, the detection of p-phenylenediamine is limited to 1wt ‰.I.e. if solution colour to be detected is by colourless
Become orange-yellow, then illustrates that the content of p-phenylenediamine in solution to be detected has reached ‰ or more 1wt.
In turn, it is preferable that in above-mentioned qualitative checking method, the concentration of 4- formoxyl isonicotinic acid phenyl ester is big in solution to be detected
It is the optium concentration observing solution and whether changing colour when 2mg/mL.
Compound of the present invention can quickly and easily detect p-phenylenediamine, while can be to p-phenylenediamine
Carry out single selective identification.Select octylame, lauryl amine, cetylamine, ethylenediamine, hexamethylene diamine, decamethylene diamine, p-phenylenediamine etc. organic
Amine is detected under the same conditions, and only solution just can be by colourless obvious when encountering p-phenylenediamine for the compound of the present invention
It is changed into orange-yellow.
Compound of the present invention can be synthesized by single step reaction, preparation process and post-processing very simple.For
Without preparing other detection reagents during p-phenylenediamine in detection solution or waste liquid, there are no need other large-scale instruments, operation
Simplicity, the restrictive conditions very little such as time, temperature.In addition, colour developing is fast and stablizes, by directly observing solution face in detection process
The variation of color can determine the presence whether there is or not p-phenylenediamine.Factory, enterprise or individual can voluntarily complete quickly to detect completely, can
Carry out popularity application.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of 4- formoxyl isonicotinic acid phenyl ester prepared by embodiment 1.
Fig. 2 is the mass spectrogram of 4- formoxyl isonicotinic acid phenyl ester prepared by embodiment 1.
Fig. 3 is the methanol extraction concentration of octylame, lauryl amine, cetylamine, ethylenediamine, hexamethylene diamine, decamethylene diamine, p-phenylenediamine
Liquid.
Fig. 4 is solution chromogenic reaction photo when the compounds of this invention detects various organic amines.
Specific embodiment
Following embodiments are only the preferred technical solution of the present invention, are not used to carry out any restrictions to the present invention.For
For those skilled in the art, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made
Any modification, equivalent substitution, improvement and etc., should all be included in the protection scope of the present invention.
Embodiment 1
The triethylamine of the parahydroxyben-zaldehyde of 1.0g, the different nicotinoyl chloride hydrochloride of 2.6g and 2.3g is added to 120mL's
In chloroform and methyl alcohol mixed liquor (volume ratio 1: 1), reacted 48 hours under the conditions of 25 DEG C.After reaction, by solution vacuum
It is spin-dried for obtaining crude product.Obtained crude product is added in methylene chloride, is heated to reflux stirring after five minutes, it is naturally cold
But room temperature is arrived, is filtered, solid is dried in vacuo to get 4- formoxyl isonicotinic acid phenyl ester.
Fig. 1 is the infrared spectrogram of 4- formoxyl isonicotinic acid phenyl ester, 3440 in figure at characteristic peak be that C=O stretching vibration is (general
Frequently), characteristic peak is respectively the C=O stretching vibration of ester group and aldehyde radical at 1730,1683, and characteristic peak is the flexible vibration of C-O-C at 1256
It is dynamic, illustrate successfully to be prepared for 4- formoxyl isonicotinic acid phenyl ester.
Fig. 2 is the mass spectrogram of 4- formoxyl isonicotinic acid phenyl ester, 249.8 in figure at characteristic peak be ion that target product adds sodium
Proton peak does not have miscellaneous peak in map, it was demonstrated that the 4- formoxyl isonicotinic acid phenyl ester purity of preparation is higher.
Embodiment 2
The triethylamine of the parahydroxyben-zaldehyde of 1.0g, the different nicotinoyl chloride hydrochloride of 2.2g and 1.7g is added to 100mL's
In chloroform and methyl alcohol mixed liquor (volume ratio 1: 0.5), reacted 38 hours under the conditions of 45 DEG C.After reaction, solution is true
Sky is spin-dried for obtaining crude product.Obtained crude product is added in methylene chloride, stirring is heated to reflux after five minutes, by its nature
It is cooled to room temperature, is filtered, solid is dried in vacuo to get 4- formoxyl isonicotinic acid phenyl ester.
Embodiment 3
The triethylamine of the parahydroxyben-zaldehyde of 1.0g, the different nicotinoyl chloride hydrochloride of 1.7g and 1.1g is added to the chlorine of 80mL
In imitative and methyl alcohol mixed liquor (volume ratio 1: 1.5), reacted 25 hours under the conditions of 62 DEG C.After reaction, by solution vacuum
It is spin-dried for obtaining crude product.Obtained crude product is added in methylene chloride, is heated to reflux stirring after five minutes, it is naturally cold
But room temperature is arrived, is filtered, solid is dried in vacuo to get 4- formoxyl isonicotinic acid phenyl ester.
Application examples 1
2mg p-phenylenediamine is mixed into 100mL water, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 3mg is added in bottle, simultaneously ultrasound 5 is heated
It after minute, after standing 30 minutes, observes that solution becomes orange-yellow from colourless, illustrates to simulate in solution to be measured containing to benzene two
Amine.
Application examples 2
3mg p-phenylenediamine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 3mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observes that solution is changed into orange-yellow by colourless, illustrate to simulate in solution to be measured containing to benzene two
Amine.
Application examples 3
4mg p-phenylenediamine is mixed into 200mL ethyl acetate, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 4mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observes that solution is changed into orange-yellow by colourless, illustrate to simulate in solution to be measured containing to benzene two
Amine.
Comparative example 1
4mg octylame is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 3mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
Comparative example 2
3mg lauryl amine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 3mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
Comparative example 3
3mg cetylamine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 5mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
Comparative example 4
4mg ethylenediamine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 5mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
Comparative example 5
5mg hexamethylene diamine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 4mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
Comparative example 6
4mg decamethylene diamine is mixed into 100mL chloroform, preparation simulation industrial wastes.
The solution to be measured of above-mentioned simulation is arrived into 1mL or so by vacuum concentrated by rotary evaporation, the methanol of 1mL is added thereto mixing
After uniformly, 1mL mixed liquor is pipetted into bottle.The 4- formoxyl isonicotinic acid phenyl ester of 4mg is added in bottle, simultaneously ultrasound 5 is heated
After minute, after standing 30 minutes, observe solution be still it is colourless, illustrate to simulate in solution to be measured without p-phenylenediamine.
In Fig. 3, number a~g be respectively p-phenylenediamine in application examples 2 and comparative example 1~6, octylame, lauryl amine, cetylamine,
Ethylenediamine, hexamethylene diamine, decamethylene diamine methanol extraction concentrate bottle.In Fig. 4, number a~g is respectively application examples 2 and comparative example 1
~6 bottle.
It can be seen from the figure that solution in 4a bottle, the i.e. chloroformic solution containing p-phenylenediamine are obviously by colourless transformation
To be orange-yellow, and color is compared with being added before detection reagent in other bottles, not big variation substantially, illustrates that 4- formoxyl is different
Niacin phenyl ester simply and easily can carry out single identity detection to p-phenylenediamine.
Claims (3)
1. compound 4- formoxyl isonicotinic acid phenyl ester is in the application of qualitative detection p-phenylenediamine.
2. whether compound described in claim 1 contains p-phenylenediamine in detection solution as p-phenylenediamine detection reagent
Using.
3. the use of the method for p-phenylenediamine in compound test solution described in claim 1 being to rotate solution vacuum to be detected
It is concentrated to 1mL or so, the methanol of 1mL is added thereto after mixing, pipettes 1mL mixed liquor into bottle.By 4- formoxyl
Isonicotinic acid phenyl ester be added bottle in, heat and ultrasound after five minutes, stand 30 minutes after, solution by it is colourless be changed into it is orange-yellow, i.e.,
Indicate that there are p-phenylenediamine in detection solution.
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| CN201811104022.7A CN110066242B (en) | 2018-09-07 | 2018-09-07 | Compound for detecting p-phenylenediamine and preparation method thereof |
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| CN201811104022.7A CN110066242B (en) | 2018-09-07 | 2018-09-07 | Compound for detecting p-phenylenediamine and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2018
- 2018-09-07 CN CN201811104022.7A patent/CN110066242B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (4)
| Title |
|---|
| A. ANTHONYSAMY ET AL.: "Synthesis, spectral, thermal and electrochemical studies of nickel (II) complexes with N2O2 donor ligands", 《INORGANIC CHEMISTRY COMMUNICATIONS》 * |
| AROCKIAM ANTHONYSAMY ET AL.: "Synthesis, spectroscopic, structural and electrochemical studies of nickel(II) and copper(II) complexes derived from 2-hydroxy-4-methacryloyloxybenzaldehyde", 《TRANSITION MET CHEM》 * |
| LI-HUA LIU ET AL.: "Methacrylate-bonded covalent-organic framework monolithiccolumns for high performance liquid chromatography", 《JOURNAL OF CHROMATOGRAPHY A》 * |
| P. KANDASAMY ET AL.: "Synthesis and Liquid Crystal Properties of Supramolecular Side-Chain Liquid-Crystalline Polymers Containing Poly(acrylic acid) Intermolecular Hydrogen Bonds", 《MOLECULAR CRYSTALS AND LIQUID CRYSTALS》 * |
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