CN104155255B - A kind of squaric amide derivant detects the method for RDX explosive - Google Patents
A kind of squaric amide derivant detects the method for RDX explosive Download PDFInfo
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- CN104155255B CN104155255B CN201410352880.9A CN201410352880A CN104155255B CN 104155255 B CN104155255 B CN 104155255B CN 201410352880 A CN201410352880 A CN 201410352880A CN 104155255 B CN104155255 B CN 104155255B
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- squaric amide
- amide derivant
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Abstract
The present invention relates to a kind of method that squaric amide derivant detects RDX explosive, belong to chemical sensing material field.Method of the present invention adopts synthesis to have optically active replacement squaric amide based chemical sensors, and with RDX molecule by after the interaction of intermolecular ydrogen bonding, the ultra-violet absorption spectrum of sensor has obvious absorption intensity to improve near 322nm.The present invention's replacement squaric amide chemical sensor synthetic method used is simple, sensing range is wide, detection sensitivity is high, is suitable for the quick detection to RDX, can be widely used in national defense industry and explosive detection field.
Description
Technical field
The present invention relates to a kind of method that squaric amide derivant detects RDX explosive, belong 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, not only significant to the detection of explosive weapon multiple on battlefield to the research of explosives sensor, also has profound significance in peace society in the safety of the people that safeguard one's country especially anti-terrorism.
Hexogen (RDX) is one of current widely used high energy, low sensitivity single chmical compound explosive, explosion velocity reaches about 8700m/s, detonate easily, be one of principal charge of the modern weapons ammunition after TNT (TNT) explosive, be widely used in composite explosives.At present, at home and abroad widely used as multiple formulas of main explosive by RDX.But the explosion accident in the explosive manufacturing shop again and again reported this year, and the generation of the public place such as business district, the airport attack of terrorism, researcher and the whole society all give the great attention of explosive detection.Especially the production later stage of explosive, in the process of pipeline cleaning and useless medicine process, understand the concrete explosive type and content that wherein contain, contribute to operating pointedly, production safety and cost control are had great significance.Literature survey found that, about the document of explosive detection mostly all for TNT explosive, about the documents and materials of RDX explosive detection are very few.Therefore, develop a kind of convenient, method that rapidly, effectively can detect RDX, become an extremely urgent research topic.
Summary of the invention
The object of this invention is to provide a kind of method that squaric amide derivant detects RDX explosive, the method can convenient, RDX can be detected rapidly, effectively, and then the research filling up RDX explosive detection is blank.
The object of the invention is to be achieved through the following technical solutions.
Squaric amide derivant detects a method for RDX explosive, and concrete steps are as follows:
Step one, with organic solvent, squaric amide derivant 1 is mixed with squaric amide derivant 1 dispersion liquid of concentration known;
Step 2, RDX explosive to be 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 RDX explosive and squaric amide derivant is respectively 0.5, and 1,2,5,10,20,50,100;
The ultra-violet absorption spectrum of the different mixed solution of step 3, determination step two gained, by the ultra-violet absorption spectrum 272nm place absorbance that records with RDX concentration determination corresponding relation, namely the standard equation y=a+bx of RDX is quantitatively detected, wherein y is the surveyed ultraviolet absorptivity corresponding containing RDX squaric amide sensor maximum absorption wavelength 272nm place, and x is the content (unit: 10 of RDX in sample
-5m), a=0.13, b=0.017;
Step 4, the testing sample containing RDX to be joined in DMF solution, be mixed with solution; Then join in squaric amide derivant 1 dispersion liquid of concentration known, measure ultra-violet absorption spectrum.By in the ultra-violet absorption spectrum of measured sample, the absorbance at 272nm place substitutes in the RDX quantitative criterion equation of step 3 gained, can determine the content of RDX in sample.
Organic solvent described in step one comprises: DMF (DMF) or dimethyl sulfoxide (DMSO).
The preparation method of described squaric amide derivant 1, concrete steps are as follows:
By square diethyl phthalate and aniline in molar ratio for 1:1 joins in container, add the mixed solvent of toluene/DMF (v/v, 19/1), add the catalyzer of lewis acid as reaction of 5% molar weight.Heat at 100 ~ 130 DEG C, reaction after 10 ~ 15 hours under the stirring rate of 10 ~ 60r/min, high speed centrifugation, rinse sediment with absolute methanol, drying can obtain squaric amide derivant 1.
In the present invention, lewis acid used is trifluoromethayl sulfonic acid zinc, p-toluenesulfonic acid zinc.
Reaction equation is as follows:
Beneficial effect
1, a kind of squaric amide derivant of the present invention detects the method for RDX explosive, squaric amide derivant based chemical sensors prepared by the present invention, the quick detection to RDX is achieved by use ultra-violet absorption spectrum, possess highly sensitive, selectivity is good, and cost is low, the feature such as convenient, can rapidly, effectively detect trace RDX explosive, national defense industry field can be widely used in, produce direct Social benefit and economic benefit.
2, a kind of squaric amide derivant of the present invention detects the method for RDX explosive, and with square diethyl phthalate for raw material, prepared squaric amide derivant 1, only single step reaction by one-step synthesis reaction, reaction conditions is gentle, and post-reaction treatment is simple, and products therefrom productive rate 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 qualitative ultraviolet spectrogram of squaric amide derivant 1 and RDX explosive in the present invention;
Fig. 4 is the quantitative ultraviolet spectrogram of squaric amide derivant 1 and RDX explosive in the present invention;
Fig. 5 be in the present invention squaric amide derivant 1 at the graph of a relation of 272nm place ultraviolet absorptivity and RDX explosive concentration.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention will be further described.
The preparation of embodiment 1, squaric amide derivant:
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 the 30mL mixed solution of toluene/DMF=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, and gained precipitation absolute methanol rinses, yield 99%, the nucleus magnetic hydrogen spectrum of product as shown in Figure 2.
The preparation of embodiment 2, squaric amide derivant:
The aniline of the square diethyl phthalate of 120 μ L and 155 μ L is dissolved in the 30mL mixed solution of toluene/DMF=19:1, and add 160mg p-toluenesulfonic acid zinc catalyst, temperature from ambient is risen to 100 DEG C, moderate-speed mixer 10 hours, reactant liquor is through high speed centrifugation, gained precipitation absolute methanol rinses, yield 96%.
The preparation of embodiment 3, squaric amide derivant:
The square diethyl phthalate of 40mL and the aniline of 51mL are dissolved in the 100mL mixed solution of toluene/DMF=19:1, temperature from ambient are 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%.
The preparation of embodiment 4, squaric amide derivant:
The square diethyl phthalate of 100mL and the aniline of 115mL are dissolved in the 150mL mixed solution of toluene/DMF=19:1, temperature from ambient are risen to 100 DEG C, moderate-speed mixer 12 hours, reactant liquor through high speed centrifugation, precipitation absolute methanol rinse, yield 85%.
The preparation of embodiment 5, sensor solution
Being joined in solvent by squaric amide derivant 1 respectively and being mixed with concentration is 1 × 10
-5the solution of mol/L, solvent is DMSO or DMF.After preparation, sensor solution can be used for the quantitative and qualitative analysis detection of RDX explosive, as shown in Figure 3-Figure 5.The standard equation that the present invention, squaric amide derivant quantitatively detects for RDX can be obtained from the quantitative analytical data of Fig. 5.
Further describe the present invention below in conjunction with example to detect the quantitative judge of RDX.
Embodiment 6
For verifying accuracy and the reliability of the detection method of RDX of the present invention, adopt artificial for preparation is containing five groups of samples of RDX explosive, the content of its RDX is respectively 10
-5, 1.5 × 10
-5, 5 × 10
-5, 10
-4, 3 × 10
-4.After stirring, gather fluorescence spectrum, adopt the RDX content of detection method to said sample to detect, its testing result is as shown in the table.
Table one: sample user amide derivatives 1 detects the quantitative judge of RDX 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 |
From the result shown in table one, adopt the inventive method to the actual detected value of RDX content and the content value added when making sample, namely theoretical content is substantially identical, has less error range.
Embodiment 7
Adopt the testing conditions substantially identical with instantiation 6, in DMSO solvent, use probe compound 1 to detect the quantitative judge of RDX in above-mentioned preparation sample, concrete outcome sees the following form.
Table two: sample user amide derivatives 1 detects the quantitative judge of RDX 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 |
From the result shown in table two, adopt the inventive method to the actual detected value of RDX content and the content value added when making sample, namely theoretical content is substantially identical, has less error range.
From shown result, although employ probe compound 1 respectively in DMF and DMSO, adopt the present invention all can obtain testing result comparatively accurately to the detection method of RDX content, and there is less error.
Compbined test data show, the beneficial effect that user's amide derivatives of the present invention carries out quantitative detecting method to RDX adopts lower-cost equipment to detect RDX content, measuring speed is fast, and simple, convenient, measurement result is accurate, reliable, reproducible.
Claims (4)
1. detect a method for RDX explosive with squaric amide derivant, it is characterized in that: concrete steps are as follows:
Step one, with organic solvent, squaric amide derivant 1 is mixed with squaric amide derivant 1 dispersion liquid of concentration known;
Step 2, RDX explosive to be 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 RDX explosive and squaric amide derivant is respectively 0.5, and 1,2,5,10,20,50,100;
The ultra-violet absorption spectrum of the different mixed solution of step 3, determination step two gained, by the ultra-violet absorption spectrum 272nm place absorbance that records with RDX concentration determination corresponding relation, namely the standard equation y=a+bx of RDX is quantitatively detected, wherein y is the surveyed ultraviolet absorptivity corresponding containing RDX squaric amide sensor maximum absorption wavelength 272nm place, x is the content of RDX in sample, and unit is 10
-5m, a=0.13, b=0.017;
Step 4, the testing sample containing RDX to be joined in DMF solution, be mixed with solution; Then join in squaric amide derivant 1 dispersion liquid of concentration known, measure ultra-violet absorption spectrum; By in the ultra-violet absorption spectrum of measured sample, the absorbance at 272nm place substitutes in the RDX quantitative criterion equation of step 3 gained, can determine the content of RDX in sample;
The chemical structural formula of described squaric amide derivant 1 is as follows:
2. a kind of squaric amide derivant as claimed in claim 1 detects the method for RDX explosive, it is characterized in that: the organic solvent described in step one comprises: DMF or dimethyl sulfoxide.
3. a kind of squaric amide derivant as claimed in claim 1 detects the method for RDX explosive, it is characterized in that: the preparation method of described squaric amide derivant 1 is: by square diethyl phthalate and aniline in molar ratio for 1:1 joins in container, add the mixed solvent of toluene/DMF, the two v/v is 19/1, adds the catalyzer of lewis acid as reaction of 5% molar weight; Heat at 100 ~ 130 DEG C, reaction after 10 ~ 15 hours under the stirring rate of 10 ~ 60r/min, high speed centrifugation, rinse sediment with absolute methanol, drying can obtain squaric amide derivant 1.
4. a kind of squaric amide derivant as claimed in claim 3 detects the method for RDX explosive, it is characterized in that: described lewis acid is trifluoromethayl sulfonic acid zinc, p-toluenesulfonic 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103724255A (en) * | 2014-01-07 | 2014-04-16 | 大连理工大学 | Preparation method of compounds used for detecting explosive RDX (Research Department eXplosive) and based on acylamino dihydropyridine structure |
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| US7666684B2 (en) * | 2006-10-11 | 2010-02-23 | Massachusetts Institute Of Technology | Determination of explosives including RDX |
| ES2345809B1 (en) * | 2009-03-31 | 2011-07-29 | Universitat De Les Illes Balears | TRIPODAL COMPOUND BASED ESCUARAMIDE, PROCESS OF OBTAINING, SYSTEM CHEMICAL CONTAINER AND PROCEDURE FOR THE DETECTION OF POLYCARBYXYLATES. |
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| CN103724255A (en) * | 2014-01-07 | 2014-04-16 | 大连理工大学 | Preparation method of compounds used for detecting explosive RDX (Research Department eXplosive) and based on acylamino dihydropyridine structure |
Non-Patent Citations (2)
| Title |
|---|
| N,N’-Diarylsquaramides： General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing;Ali Rostami et al.;《Journal of organic chemistry》;20100520;第75卷(第12期);第3983-3992页 * |
| The Squaramide versus Urea Contest for Anion Recognition;Valeria Amendola et al.;《Chemistry-A European Journal》;20101231;第16卷(第14期);第4368-4380页 * |
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Inventor after: Li Xin Inventor after: Li Lijie Inventor after: Shu Qinghai Inventor after: Jin Shaohua Inventor after: Wang Yuqiao Inventor before: Li Lijie Inventor before: Shu Qinghai Inventor before: Jin Shaohua Inventor before: Li Xin Inventor before: Wang Yuqiao |
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Granted publication date: 20160120 Termination date: 20180723 |