CN110186882B - Fluorescent test paper for detecting nitro compounds and preparation method thereof - Google Patents
Fluorescent test paper for detecting nitro compounds and preparation method thereof Download PDFInfo
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- CN110186882B CN110186882B CN201910421262.8A CN201910421262A CN110186882B CN 110186882 B CN110186882 B CN 110186882B CN 201910421262 A CN201910421262 A CN 201910421262A CN 110186882 B CN110186882 B CN 110186882B
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- 150000002828 nitro derivatives Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000000243 solution Substances 0.000 claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004814 polyurethane Substances 0.000 claims abstract description 15
- 229920002635 polyurethane Polymers 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 9
- IZIJBCKLZLJDLX-UHFFFAOYSA-N OC1=C(C=C(C(=C1)CNC(C=C)=O)O)CNC(C=C)=O Chemical compound OC1=C(C=C(C(=C1)CNC(C=C)=O)O)CNC(C=C)=O IZIJBCKLZLJDLX-UHFFFAOYSA-N 0.000 claims description 5
- 238000002791 soaking Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000012456 homogeneous solution Substances 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 8
- 239000002360 explosive Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- -1 2-nitrotoluene (oNT) Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
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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
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- 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
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6447—Fluorescence; Phosphorescence by visual observation
-
- 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
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
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- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
本发明一种检测硝基化合物的荧光试纸及其制备方法，称取(N，N'‑((2,5‑二羟基‑1,4‑亚苯基)二(亚甲基))二丙烯酰胺、聚乙二醇单甲醚、无水四氢呋喃、六亚甲基二异氰酸酯和1,4‑二氮杂二环[2.2.2]辛烷加入干燥的容器中并混合成均匀的溶液；然后将溶液在60—80℃下加热6—8小时；在溶液粘稠后，加入乙醚并真空干燥得到荧光聚氨酯；将荧光聚氨酯溶解在乙腈和水的混合溶液中，然后将裁剪的纸片浸润、烘干得到检测硝基化合物的荧光试纸；本发明制备的荧光试纸，制备方法简单，原料易得，与硝基化合物接触，荧光消失，并且对TNP具有高灵敏度，该发明对于检测危险品的低成本提供了选择。
The present invention is a fluorescent test paper for detecting nitro compounds and a preparation method thereof. Amide, polyethylene glycol monomethyl ether, anhydrous tetrahydrofuran, hexamethylene diisocyanate, and 1,4-diazabicyclo[2.2.2]octane were added to a dry container and mixed into a homogeneous solution; then The solution is heated at 60-80 ℃ for 6-8 hours; after the solution is viscous, add ether and vacuum dry to obtain fluorescent polyurethane; dissolve the fluorescent polyurethane in a mixed solution of acetonitrile and water, and then infiltrate the cut paper, The fluorescent test paper for detecting nitro compounds is obtained by drying; the fluorescent test paper prepared by the present invention has simple preparation method, easy-to-obtain raw materials, and when contacted with nitro compounds, the fluorescence disappears, and has high sensitivity to TNP, and the invention has low performance for detecting dangerous goods. Cost provides options.
Description
Technical Field
The invention relates to a fluorescent test paper and a preparation method thereof, in particular to a fluorescent test paper for detecting nitro compounds and a preparation method thereof, belonging to the field of organic compound detection.
Background
The detection of explosives by simple and practical methods has become a crucial problem. Nitro-chemical combination is the main component of explosives, of which 2,4, 6-Trinitrophenol (TNP) (picric acid) is an extremely dangerous substance, a compound with a greater explosive power than other nitro-compounds such as 2-nitrotoluene (oNT), Nitrobenzene (NB) and 2,4, 6-trinitrotoluene (TNT). TNP is also used in industrial dyes and as a clinical chemical agent, which can cause serious pollution of irrigated land and groundwater supply, harmful to human health, and therefore, rapid and efficient detection of nitro compounds is required. At present, although various explosive detection technologies, such as gas chromatography spectroscopy (GC-MS), Surface Enhanced Raman Spectroscopy (SERS) and electrochemical methods, can accurately detect explosives, the methods have the disadvantages of expensive instruments, complex operation, inconvenience in carrying and the like.
Disclosure of Invention
The invention aims to provide the fluorescent test paper for detecting the nitro compound, which has simple preparation method and easily obtained raw materials, and can observe fluorescence under an ultraviolet lamp by naked eyes and the preparation method thereof.
The invention aims to provide the fluorescence test paper for detecting the nitro compound, which is prepared by the following steps:
the method comprises the following steps: preparing fluorescent polyurethane: weighing 0.5-1 g of N, N' - ((2, 5-dihydroxy-1, 4-phenylene) bis (methylene)) bisacrylamide, 1-2 g of polyethylene glycol monomethyl ether, 20-25 mL of anhydrous tetrahydrofuran, 1-2 g of hexamethylene diisocyanate, and 0.1-0.5 g of 1, 4-diazabicyclo [2.2.2] octane into a dry container and mixing to obtain a uniform solution; then heating the solution at 60-80 ℃ for 6-8 hours; adding ether after the solution is viscous, and performing vacuum drying to obtain fluorescent polyurethane;
step two: dissolving 0.1-0.3 g of fluorescent polyurethane in a mixed solution of acetonitrile and water, and then infiltrating and drying a cut paper sheet to obtain fluorescent test paper for detecting nitro compounds;
the invention also includes such features:
1. the ratio of acetonitrile to water is 1: 1 to 1.5;
2. soaking the paper sheet for 2-5 minutes;
3. the size of the paper sheet is 1-3cm multiplied by 2-5 cm.
A preparation method of fluorescent test paper for detecting nitro compounds comprises the following steps:
the method comprises the following steps: preparing fluorescent polyurethane: weighing 0.5-1 g of N, N' - ((2, 5-dihydroxy-1, 4-phenylene) bis (methylene)) bisacrylamide, 1-2 g of polyethylene glycol monomethyl ether, 20-25 mL of anhydrous tetrahydrofuran, 1-2 g of hexamethylene diisocyanate, and 0.1-0.5 g of 1, 4-diazabicyclo [2.2.2] octane into a dry container and mixing to obtain a uniform solution; then heating the solution at 60-80 ℃ for 6-8 hours; adding ether after the solution is viscous, and performing vacuum drying to obtain fluorescent polyurethane;
step two: dissolving 0.1-0.3 g of fluorescent polyurethane in a mixed solution of acetonitrile and water, and then infiltrating and drying a cut paper sheet to obtain fluorescent test paper for detecting nitro compounds;
the ratio of acetonitrile to water is 1: 1 to 1.5;
soaking the paper sheet for 2-5 minutes;
the size of the paper sheet is 1-3cm multiplied by 2-5 cm.
Compared with the prior art, the invention has the beneficial effects that:
the fluorescent test paper prepared by the invention has the advantages of simple preparation method and easily obtained raw materials, can observe fluorescence by naked eyes under an ultraviolet lamp, is contacted with a nitro compound, has no fluorescence, has high sensitivity to TNP, and provides a choice for detecting dangerous goods at low cost.
Drawings
FIG. 1 is a graph showing the fluorescence response of the test strip of example 1 at different concentrations of NP and TNP.
Detailed Description
The present invention will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the protection scope of the present invention is not limited to the following embodiments.
A fluorescent test paper for detecting nitro compounds and a preparation method thereof, the preparation steps are as follows:
step 1, preparing fluorescent polyurethane, weighing p-HABAN, N' - ((2, 5-dihydroxy-1, 4-phenylene) di (methylene)) diacrylamide, 0.5-1 g), polyethylene glycol monomethyl ether (1-2 g), anhydrous tetrahydrofuran (20-25 mL), hexamethylene diisocyanate (1-2 g) and 1, 4-diazabicyclo [2.2.2] octane (0.1-0.5 g) according to a certain mass ratio, and adding the mixture into a dry two-neck round-bottom flask. The solution is heated at 60-80 ℃ for 6-8 hours under nitrogen. After the clear solution became very viscous, the product precipitated from excess ether and was then dried under vacuum for some time to give the product.
Step 2, dissolve the product (0.1-0.3 g) in acetonitrile: and (2) soaking a paper sheet cut into a size of (1-3) cm x (2-5) cm in a solution of a water (1: 1-1.5 v/v) solution in acetonitrile containing a product: taking out and drying the paper after 2-5min in the mixed solution of water to obtain the fluorescent paper.
Example 1:
p-HABA (0.72g), polyethylene glycol monomethyl ether (1.19g), anhydrous tetrahydrofuran (24mL), hexamethylene diisocyanate (1.80g) and 1, 4-diazabicyclo [2.2.2] octane (0.35g) were weighed into a dry two-necked round-bottomed flask. The solution was heated at 75 ℃ for 8 hours under nitrogen atmosphere. After the clear solution became very viscous, the product precipitated from excess ether and was then dried under vacuum for 24h to give the product.
0.11g of the product was dissolved in acetonitrile: in a solution of aqueous solution (1: 1v/v) (10mM), then a paper sheet cut to a size of 1 cm. times.4 cm was soaked in acetonitrile containing the product: and (3) taking out and drying the mixed solution of water (10mM) after 3min to obtain a fluorescent paper sheet.
FIG. 1 is a graph showing fluorescence response behavior of test strips prepared according to example 1 of the present invention at different concentrations of NP and TNP. It can be obviously seen that the fluorescence of the test paper is weaker and weaker along with the increase of the concentration of the nitro compound, and the test paper has higher sensitivity to TNP.
Example 2:
p-HABA (0.72g), polyethylene glycol monomethyl ether (1.19g), anhydrous tetrahydrofuran (24mL), hexamethylene diisocyanate (1.80g) and 1, 4-diazabicyclo [2.2.2] octane (0.35g) were weighed into a dry two-necked round-bottomed flask. The solution was heated at 75 ℃ for 8 hours under nitrogen atmosphere. After the clear solution became very viscous, the product precipitated from excess ether and was then dried under vacuum for 24h to give the product.
0.11g of the product was dissolved in acetonitrile: in a solution of aqueous solution (1: 1.5v/v) (10mM), then a paper sheet cut to a size of 1cm × 4cm was soaked in acetonitrile containing the product: and (3) taking out and drying the mixed solution of water (10mM) after 3min to obtain a fluorescent paper sheet.
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
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