CN104155272B - A kind of method of squaric amide derivant detection TNT explosive - Google Patents
A kind of method of squaric amide derivant detection TNT explosive Download PDFInfo
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- CN104155272B CN104155272B CN201410354335.3A CN201410354335A CN104155272B CN 104155272 B CN104155272 B CN 104155272B CN 201410354335 A CN201410354335 A CN 201410354335A CN 104155272 B CN104155272 B CN 104155272B
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Abstract
The method that the present invention relates to a kind of squaric amide derivant detection TNT explosive, belongs to chemical sensing material field.The method of the present invention adopts synthesis to have optically active replacement squaric amide compound, and the TNT molecule interaction by intermolecular hydrogen bonding, responds at ultra-violet absorption spectrum and making a choice property of fluorescence spectrum respectively.After replacing squaric amide compound and TNT effect, uv absorption wavelength has very strong red shift, and obvious cancellation occurs fluorescence.Replacement squaric amide chemical sensor synthetic method used by the present invention is simple, detection range is wide, detection sensitivity is high, is suitable for 10-6Mol/L to 10-3The quick detection of mol/L TNT；Adopt the inventive method quick detection to TNT, it is possible to judged by the change of naked-eye observation sensor solution color, can be widely applied to national defense industry and public safety field.
Description
Technical field
The method that the present invention relates to a kind of squaric amide derivant detection TNT explosive, belongs to chemical sensing material field.
Background technology
Society, peaceful development is the common theme of countries in the world, but, terrorist activities is rampant in recent years, utilize explosive to carry out conventional means that the attack of terrorism is terrorist, national security in serious threat, and the research of explosives sensor is not only significant to the detection of explosive weapon multiple on battlefield, also has profound significance in peace society is to the safety especially anti-terrorism of the people that safeguard one's country.
Explosive category is a lot, the dangerous materials such as most explosives all contain nitro compound, wherein trinitrotoluene (TNT) is most widely used, it is the composition contained by multiple explosive or attaches product and degradation product, now have been developed that and multiple can be used for explosive TNT detection method, such as wave spectrum Detection Techniques, chemical sensitisation technology, biosensor technique, microelectromechanical systems (MEMS) sensor technology etc., sensor based on fluorescent chemicals has highly sensitive, selectivity is good, cost is low, the feature such as convenient, can be rapid, effectively detect trace explosive, therefore fluorescent chemicals sensor develops rapidly for the technology of explosive detection.
Fluorescent material, as sensing material, by the change of fluorescent intensity, can realize the detection to detected material and signal transmission.Increasingly receiving publicity in recent ten years, this is primarily due to them and demonstrates the photoelectric property of some uniquenesses, can make at New Generation Optical electrical part and obtain various application in the research of chemical-biological fluorescent optical sensor.
The method report of TNT explosive detection has a variety of, including high performance liquid chromatography (Rahimi-Nasrabadi, M.；Zahedi,M.M.；Pourmortazavi,S.M.；Heydari,R.；Rai,H.；Jazayeri,J.；Javidan, A.Microchim.Acta, 2012,177, P145), gas chromatography-mass spectrography (Berg, M.；Bolotin,J.；Hofstetter, T.B.Anal.Chem., 2007,79, P2386), ion migration mass spectrum (Dasary, S.S.R.；Singh,A.K.；Senapati,D.；Yu,H.T.；Ray, P.C.J.Am.Chem.Soc.2009,131, P13806), surface enhanced raman spectroscopy (Guerra-Diaz, P.；Gura,S.；Almirall, J.R.Anal.Chem.2010,82, P2826), nanotechnology (Li, X.；Liu,S.；Wu,Z.；Jiang, J.ActaChim.Sinica, 2014,72, P563) etc..But, these analyze methods, and some needs expensive analytical tool, and some needs loaded down with trivial details sensor preparation process, detection cycle long, all has certain deficiency.
Summary of the invention
The invention aims to solution prior art detection technique cost intensive, the problem to analytical tool precision requirement height and detection cycle length, it is provided that the method for a kind of squaric amide derivant detection TNT explosive.
It is an object of the invention to be achieved through the following technical solutions.
The method of a kind of squaric amide derivant detection TNT explosive, specifically comprises the following steps that
Step one, with organic solvent, squaric amide derivant 1 is configured to squaric amide derivant 1 dispersion liquid of concentration known；
Step 2, TNT explosive is joined in squaric amide derivant 1 dispersion liquid of step one gained, be configured to the mixed solution of variable concentrations；The mol ratio of TNT explosive and squaric amide derivant respectively 0.5,1,2,5,10,20,50,100；
Step 3, the ultra-violet absorption spectrum of determination step two gained difference mixed solution or fluorescence spectrum, the change of the ultraviolet absorptivity at the 276nm place recorded and TNT concentration are determined corresponding relation, namely the normal equation one: y=a+bx of detection by quantitative TNT is obtained, wherein y is the ultraviolet absorptivity that the mixed solution containing TNT squaric amide derivant 1 surveyed is corresponding at maximum absorption wavelength 276nm place, x is the concentration of TNT in sample, unit: 10-5M, a=0.11, b=0.019；The change of the 561nm place fluorescence intensity level recorded and TNT concentration are determined corresponding relation, namely the normal equation two: y=a+bx of detection by quantitative TNT is obtained, wherein y is the fluorescence intensity level that the mixed solution containing TNT squaric amide derivant 1 surveyed is corresponding at 561nm place, x is the concentration of TNT in sample, unit: 10-5M, a=1.78, b=0.34；
Step 4, the testing sample containing TNT is joined in DMF solution, be configured to solution；It is then added in squaric amide derivant 1 dispersion liquid of concentration known of step one gained, measure ultra-violet absorption spectrum or the fluorescence spectrum of gained mixed solution, the 276nm place ultraviolet absorptivity of measured mixed solution is substituted in the TNT quantitative criterion equation one of step 3 gained；Or the 561nm place fluorescence intensity level of measured mixed solution is substituted in the TNT quantitative criterion equation two of step 3 gained, namely can determine that the content of TNT in sample；
Organic solvent described in step one includes: N,N-dimethylformamide (DMF) or dimethyl sulfoxide (DMSO).
The preparation method of described squaric amide derivant 1, specifically comprises the following steps that
Side's diethyl phthalate and aniline are joined in there-necked flask for 1:1 in molar ratio, adds the mixed solvent that volume ratio is the toluene of 19:1 and DMF, add the lewis acid catalyst as reaction of 5% mole.Heat at 100～130 DEG C, under the mixing speed of 10～60r/min after reaction 10～15 hours, high speed centrifugation, rinse precipitate with absolute methanol, dry can obtain squaric amide derivant 1.
In the present invention, lewis acid used is trifluoromethayl sulfonic acid zinc or p-methyl benzenesulfonic acid zinc.
Reaction equation is as follows:
Beneficial effect
1, the method for a kind of squaric amide derivant detection TNT explosive of the present invention, squaric amide derivant based chemical sensors prepared by the present invention, ultra-violet absorption spectrum and fluorescent spectrometry is used all to achieve the detection by quantitative to TNT respectively, detecting instrument is relatively inexpensive and reaction is quick, analytical cycle is greatly shortened, testing cost effectively reduces, can rapidly, effectively detect trace TNT explosive, it is suitable for being widely used in national defense industry field, produces direct Social benefit and economic benefit.
2, the method for a kind of squaric amide derivant detection TNT explosive of the present invention, with side's diethyl phthalate for raw material, is prepared for squaric amide derivant 1 by one-step synthesis reaction, and only single step reaction, reaction condition is gentle, and post-reaction treatment is simple, and products therefrom productivity is higher.
Accompanying drawing explanation
Fig. 1 is the synthesis schematic diagram of squaric amide derivant 1 in the present invention；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure synthesizing squaric amide derivant 1 in the present invention；
Fig. 3 is the quantitative ultraviolet spectrogram of squaric amide derivant 1 and TNT explosive in the present invention；
Fig. 4 is the graph of a relation of squaric amide derivant 1 ultra-violet absorption spectrum 276nm place ultraviolet absorptivity and added TNT explosive mol ratio in the present invention；
Fig. 5 is the quantitative fluorescence spectrogram of squaric amide derivant 1 and TNT explosive in the present invention, and excitation wavelength is 278nm；
Fig. 6 is the 561nm place fluorescence intensity graph of a relation with added TNT explosive mol ratio of squaric amide derivant 1 in the present invention.
Detailed description of the invention
Below in conjunction with embodiment, the present invention will be further described with accompanying drawing.
Embodiment 1, squaric amide derivant 1 preparation:
Synthetic route as shown in Figure 1, the aniline of the square diethyl phthalate of 50 μ L and 60 μ L is dissolved in toluene/N, in the 30mL mixed solution of dinethylformamide=19:1, and add 13.8mg trifluoromethayl sulfonic acid zinc catalyst, temperature from ambient is risen to 100 DEG C, moderate-speed mixer 8 hours, reactant liquor is through high speed centrifugation, gained precipitation absolute methanol rinses, and yield 99%, product nucleus magnetic hydrogen spectrum is as shown in Figure 2.
Embodiment 2, squaric amide derivant 1 preparation:
The aniline of the square diethyl phthalate of 120 μ L and 155 μ L is dissolved in toluene/N, in the 30mL mixed solution of dinethylformamide=19:1, and add 160mg p-methyl benzenesulfonic acid zinc catalyst, temperature from ambient is risen to 100 DEG C, moderate-speed mixer 10 hours, reactant liquor is through high speed centrifugation, and gained precipitation absolute methanol rinses, yield 96%.
Embodiment 3, squaric amide derivant 1 preparation:
The aniline of the square diethyl phthalate of 40mL and 51mL is dissolved in the 100mL mixed solution of toluene/DMF=19:1, temperature from ambient is risen to 120 DEG C, moderate-speed mixer 9 hours, reactant liquor is through high speed centrifugation, and gained precipitation absolute methanol rinses, yield 94%.
Embodiment 4, squaric amide derivant 1 preparation:
The aniline of the square diethyl phthalate of 100mL and 115mL is dissolved in the 150mL mixed solution of toluene/DMF=19:1, temperature from ambient is risen to 100 DEG C, moderate-speed mixer 12 hours, reactant liquor through high speed centrifugation, precipitation rinse with absolute methanol, yield 85%.
Embodiment 5, squaric amide derivant 1 the preparation of dispersion liquid
Squaric amide derivant 1 being joined respectively and being configured to concentration in solvent is 1 × 10-5The solution of mol/L, solvent is DMSO or DMF.The dispersion liquid of squaric amide derivant 1 of preparation can be used for respectively under ultra-violet absorption spectrum (Fig. 3, Fig. 4) and fluorescence spectrum (Fig. 5, Fig. 6) to the qualitative of TNT explosive and detection by quantitative.From the quantitative analytical data of Fig. 4 and Fig. 6, the quantitative measurement standard equation to TNT explosive when ultra-violet absorption spectrum and fluorescence spectrum of squaric amide derivant in the present invention can be respectively obtained.
Further describe the present invention quantitative judge to TNT below in conjunction with example to detect.
Embodiment 6
For verifying the accuracy of TNT explosive detection method of the present invention and reliability, adopt the five groups of samples manually prepared containing TNT explosive, the content of its TNT respectively 10-5,1.5×10-5, 5 × 10-5, 10-4, 3 × 10-4.Gathering ultra-violet absorption spectrum after stirring, adopt detection method medium ultraviolet absorption spectrometry that the TNT content of said sample is detected, its testing result is as shown in the table.
Table one: the quantitative judge of TNT is detected by sample user's amide derivatives 1 in DMF solvent
| Sample | 1 | 2 | 3 | 4 | 5 |
| Theoretical content | 10-5 | 1.5×10-5 | 5×10-5 | 10-4 | 3×10-4 |
| Detection level | 0.98×10-5 | 1.47×10-5 | 4.97×10-5 | 1.03×10-4 | 3.02×10-4 |
Result shown in table one is it can be seen that adopt the inventive method to the actually detected value of TNT content and the content value added when making sample, and namely theoretical content is essentially identical, has less range of error.
Embodiment 7
Adopting the sample identical with embodiment 6, use fluorescent spectrometry in the present invention by squaric amide derivant 1, the quantitative judge of TNT in above-mentioned preparation sample to be detected in DMSO, concrete outcome is shown in following table.
Table two: the quantitative judge of TNT is detected by sample user's amide derivatives 1 in DMSO solvent
| Sample | 1 | 2 | 3 | 4 | 5 |
| Theoretical content | 10-5 | 1.5×10-5 | 5×10-5 | 10-4 | 3×10-4 |
| Detection level | 0.98×10-5 | 1.48×10-5 | 5.02×10-5 | 1.02×10-4 | 2.97×10-4 |
Embodiment 8
Adopting the sample identical with embodiment 6, use the fluorescent spectrometry of the present invention by squaric amide derivant 1, the quantitative judge of TNT in above-mentioned preparation sample to be detected in DMF, concrete outcome is shown in following table.
Table three: the quantitative judge of TNT is detected by sample user's amide derivatives 1 in DMF solvent
| Sample | 1 | 2 | 3 | 4 | 5 |
| Theoretical content | 10-5 | 1.5×10-5 | 5×10-5 | 10-4 | 3×10-4 |
| Detection level | 0.96×10-5 | 1.49×10-5 | 4.98×10-5 | 1.01×10-4 | 3.02×10-4 |
Result shown in table three is it can be seen that adopt the inventive method to the actually detected value of TNT content and the content value added when making sample, and namely theoretical content is essentially identical, has less range of error.
Embodiment 9
Adopting testing conditions substantially the same manner as Example 8, in DMSO, user's amide derivatives 1 is to the quantitative judge detection of TNT in above-mentioned preparation sample, and concrete outcome is shown in following table.
Table four: the quantitative judge of TNT is detected by sample user's amide derivatives 1 in DMSO solvent
Result shown in table four is it can be seen that adopt the inventive method to the actually detected value of TNT content and the content value added when making sample, and namely theoretical content is essentially identical, has less range of error.
From shown result, employ squaric amide derivant 1 as sensor, no matter in DMF or DMSO solvent, no matter adopt ultraviolet absorption spectroscopy or fluorescent spectrometry, adopt the present invention that the detection method of TNT content all can be obtained accurate testing result, and there is less error.
Compbined test data show, TNT is carried out quantitative detecting method and provides the benefit that TNT content is detected by the lower-cost equipment of employing by user's amide derivatives of the present invention, measuring speed is fast, and simple, convenient, measurement result is accurate, reliable, reproducible.
Claims (4)
1. the method detecting TNT explosive by squaric amide derivant, it is characterised in that: specifically comprise the following steps that
Step one, with organic solvent, squaric amide derivant 1 is configured to squaric amide derivant 1 dispersion liquid of concentration known；
Step 2, TNT explosive is joined in squaric amide derivant 1 dispersion liquid of step one gained, be configured to the mixed solution of variable concentrations；The mol ratio of TNT explosive and squaric amide derivant respectively 0.5,1,2,5,10,20,50,100；
Step 3, the ultra-violet absorption spectrum of determination step two gained difference mixed solution or fluorescence spectrum, the ultraviolet absorptivity at the 276nm place recorded and TNT concentration are determined corresponding relation, namely the normal equation one: y=a+bx of detection by quantitative TNT is obtained, wherein y is the ultraviolet absorptivity that the mixed solution containing TNT squaric amide derivant 1 surveyed is corresponding at maximum absorption wavelength 276nm place, x is the concentration of TNT in sample, unit: 10-5M, a=0.11, b=0.019；The change of the 561nm place fluorescence intensity level recorded and TNT concentration are determined corresponding relation, namely the normal equation two: y=a+bx of detection by quantitative TNT is obtained, wherein y is the fluorescence intensity level that the mixed solution containing TNT squaric amide derivant 1 surveyed is corresponding at 561nm place, x is the concentration of TNT in sample, unit: 10-5M, a=1.78, b=0.34；
Step 4, the testing sample containing TNT is joined in DMF solution, be configured to solution；It is then added in squaric amide derivant 1 dispersion liquid of concentration known of step one gained, measure ultra-violet absorption spectrum or the fluorescence spectrum of gained mixed solution, the 276nm place ultraviolet absorptivity of measured mixed solution is substituted in the TNT quantitative criterion equation one of step 3 gained；Or the 561nm place fluorescence intensity level of measured mixed solution is substituted in the TNT quantitative criterion equation two of step 3 gained, namely can determine that the content of TNT in sample；
The chemical structural formula of described squaric amide derivant 1 is as follows:
2. the method for a kind of squaric amide derivant as claimed in claim 1 detection TNT explosive, it is characterised in that: the organic solvent described in step one includes: DMF or dimethyl sulfoxide.
3. the method for a kind of squaric amide derivant as claimed in claim 1 detection TNT explosive, it is characterized in that: the preparation method of described squaric amide derivant 1 is: join in there-necked flask for 1:1 in molar ratio by side's diethyl phthalate and aniline, add toluene and N that volume ratio is 19:1, the mixed solvent of dinethylformamide, adds the lewis acid catalyst as reaction of 5% mole；Heat at 100～130 DEG C, under the mixing speed of 10～60r/min after reaction 10～15 hours, high speed centrifugation, rinse precipitate with absolute methanol, dry can obtain squaric amide derivant 1.
4. the method for a kind of squaric amide derivant as claimed in claim 3 detection TNT explosive, it is characterised in that: described lewis acid is trifluoromethayl sulfonic acid zinc or p-methyl benzenesulfonic acid zinc.
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| CN104865204B (en) * | 2015-01-16 | 2018-03-30 | 北京理工大学 | A kind of method for F colorimetric detections |
| CN104897595A (en) * | 2015-05-21 | 2015-09-09 | 四川大学 | Method for simultaneously measuring contents of HMX, RDX and TNT in PBX explosive by ultraviolet spectrometry |
| CN106167500B (en) * | 2016-06-08 | 2018-07-31 | 华中科技大学 | A kind of compound and preparation method thereof for explosive TNT detection and analysis |
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