CN104792759B - A kind of fluorescent test paper of Rapid Detection of Formaldehyde and preparation method and application - Google Patents
A kind of fluorescent test paper of Rapid Detection of Formaldehyde and preparation method and application Download PDFInfo
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- CN104792759B CN104792759B CN201510208510.2A CN201510208510A CN104792759B CN 104792759 B CN104792759 B CN 104792759B CN 201510208510 A CN201510208510 A CN 201510208510A CN 104792759 B CN104792759 B CN 104792759B
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Abstract
The invention discloses a kind of fluorescent test paper of energy Rapid Detection of Formaldehyde, it is to be made up of the unstressed configuration brightening agent test paper of load fluorescence probe naphthalimide derivative, wherein described fluorescent test paper is blackish green, length × width x thickness size is 100~75mm × 15~8mm × 1~0.5mm, the naphthalimide derivative content loaded on every fluorescent test paper is not less than 0.01mg, test paper for matrix is blackish green accurate pH test paper, the naphthalimide derivative for loading thereon is N amino 4 (1 piperazinyl) 1, 8 naphthalimides, or N amino 4 (1 piperidyl) 1, 8 naphthalimides, or N amino 4 (1 pyrrolidinyl) 1, 8 naphthalimides.The fluorescent test paper of energy Rapid Detection of Formaldehyde of the invention is easily prepared, easy to use, the formaldehyde in environment can quick and precisely be detected and judged.
Description
Technical field
The present invention relates to a kind of fluorescent test paper of Rapid Detection of Formaldehyde and preparation method and application, belong to analytical chemistry skill
Art field.
Background technology
Formaldehyde is a kind of colourless irritative gas soluble in water, can be absorbed by the body through respiratory tract.When in room air
Content of formaldehyde is 0.1mg/m3When just have peculiar smell and sense of discomfort；0.5mg/m3When eyes can be stimulated to cause shed tears；0.6mg/m3Shi Yin
Play throat discomfort or pain；Concentration is high again to cause Nausea and vomiting, cough, uncomfortable in chest, asthma even pulmonary emphysema；And in working as air
Formaldehyde reaches 30mg/m3When can at once cause death.Long Term Contact low dosage formaldehyde can cause chronic respiratory disease, new life
The reduction of youngster's constitution, chromosome abnormality, or even cause nasopharyngeal carcinoma.The formaldehyde of high concentration to nervous system, immune system, liver etc. all
It is toxic.Formaldehyde also has teratogenesis, carcinogenesis, according to epidemiology survey, the people of Long Term Contact formaldehyde, can cause nasal cavity, oral cavity,
Skin and gastral cancer.
The Analysis Methods for Formaldehyde of report mainly has four kinds at present：Spectrophotometer chemical analysis, electrochemical process, chromatography
And sensor method.
(1) spectrophotometer chemical analysis are the main quasi- detection methods of PARA FORMALDEHYDE PRILLS(91,95) in national standard, and it is based on not
A kind of qualitative and quantitative analysis method set up to the selective absorbing of electromagnetic radiation with the material of molecular structure, is room, spins
Fabric, formaldehyde in food detect a kind of most conventional method.This method needs formaldehyde and acetylacetone,2,4-pentanedione reagent, magenta-sulfurous
There is chemical reaction material of the generation with certain ultraviolet-ray visible absorbing, Jin Ertong in the developers such as acid, chromotropic acid, phloroglucin
Crossing spectrophotometer PARA FORMALDEHYDE PRILLS(91,95) carries out indirect detection, and operating process is complicated, cumbersome, time-consuming, and easily by the shadow of other aldehydes or ketones
Ring.
(2) electrochemical methods is based on electric current (voltammetry), electricity (coulometry), the current potential produced in chemical reaction
The change of (potentiometry), judges the method that the concentration of analyte in reaction system carries out quantitative analysis, is conventionally used for formaldehyde examination
Have polarography and potentiometry both.Polarogarphy is higher to the pre-treatment of sample requirement, and potentiometry is one newly to grind
Study carefully method, it is less in actual applications.
(3) chromatogram has powerful separation efficiency, is difficult to be disturbed by sample substrate and reagent color, to complex sample
Detection is sensitive, accurate, can be directly used for the analysis detection of PARA FORMALDEHYDE PRILLS(91,95) in room, textile, food.This method is needed in sample
After formaldehyde performs the derivatization treatment using derivating agents such as DNPH, imidazoles, ethyl mercaptan, hydrazine sulfates, then it is measured,
But chromatography is higher to equipment requirement, the derivatization time is long, and the step operation process such as extraction is loaded down with trivial details, is not suitable for general experiment
Room and the field quick detection of family, it is difficult to meet the market demand.
(4) electrochemical sensor is relatively simple for structure, and cost, wherein high-quality properties of product are stable, is measured than relatively low
Scope and resolution ratio can reach the requirement of Indoor Environment Detection substantially.This method has the disadvantage that suffered interfering material is more, and due to electrolysis
There is irreversible chemical reaction and be consumed in matter, therefore its working life is typically shorter with tested formaldehyde gas.Optical pickocff
Price is somewhat expensive, and volume is larger, is not suitable on line real time, is restricted its popularity for using.
Above-mentioned four kinds of Analysis Methods for Formaldehyde are difficult while accomplish with low cost, easy to operate and quick detection, therefore, it is difficult to
Meet the demand of market PARA FORMALDEHYDE PRILLS(91,95) quick detection.
XRF receives much concern because sensitivity for analysis is high, selectivity is strong and easy to use, but is currently based on
In the market does not retrieve the simple machine or articles for use based on fluorescence analysis of commercialization.
Known test paper species is various, such as pH test paper, but about being used to detect the examination of formaldehyde based on fluorescence analysis mechanism
Paper yet there are no report.
The content of the invention
In view of the shortcomings of the prior art, the problem to be solved in the present invention is to provide a kind of fluorescence examination of energy Rapid Detection of Formaldehyde
Paper and its application.
The fluorescent test paper of energy Rapid Detection of Formaldehyde of the present invention, by the nothing of load fluorescence probe naphthalimide derivative
Fluorescent whitening agent test paper is constituted, it is characterised in that：The fluorescent test paper is blackish green, and length × width x thickness size is 100~75mm
× 15~8mm × 1~0.5mm, the naphthalimide derivative content loaded on every fluorescent test paper is not less than 0.01mg；Wherein use
It is blackish green accurate pH test paper in the test paper of matrix, the naphthalimide derivative for loading thereon is N- amino -4- (1- piperazines
Base) -1,8- naphthalimides, or N- amino -4- (1- piperidyls) -1,8- naphthalimides, or N- amino -4- (1- pyrrolidinyls) -
1,8- naphthalimides.
The fluorescent test paper preferred size of above-mentioned energy Rapid Detection of Formaldehyde is long × and width x thickness is 75mm × 10mm × 0.7mm,
The naphthalimide derivative is preferably N- amino -4- (1- piperazinyls) -1,8- naphthalimides.
It is of the present invention can Rapid Detection of Formaldehyde fluorescent test paper preparation method, step is：
(1) N- amino -4- (1- piperazinyls) -1, the 8- naphthalimides for being solvent compound concentration as 1mM with methyl alcohol, or N- ammonia
Base -4- (1- piperidyls) -1,8- naphthalimides, or N- amino -4- (1- pyrrolidinyls) -1,8- naphthalimide solution；
(2) blackish green accurate pH test paper is immersed in during step (1) prepares solution, is taken out afterwards within 10 minutes, at room temperature
Dry, that is, obtain blackish green, the non-blooming energy Rapid Detection of Formaldehyde under uviol lamp fluorescent test paper.
Above-mentioned naphthalimide derivative is 4 naphthalimide derivatives containing different substituents group, and its general structure is such as
Under：
The preparation method of above-mentioned naphthalimide derivative is：Hydrazine hydrate, the bromo- 1,8- naphthalic anhydrides of 4- and ethanol are added
Flowed back 4~5 hours in single-necked flask, filtered after being cooled to room temperature, drying obtains light gray solid；By this solid and anhydrous
Piperazine (3eq) or piperidines (3eq), glycol monoethyl ether are added in single-necked flask, the lower backflow of nitrogen protection 6~8 hours, are cooled to
Vacuum distillation obtains dark brown viscous solid after room temperature；This sticky solid is washed with water and methanol mixed solvent, naphthoyl is obtained final product
Imine derivative.
The application of fluorescent test paper formaldehyde in detection air or water of energy Rapid Detection of Formaldehyde of the present invention.
On fluorescent test paper of the present invention load naphthalimide derivative as formaldehyde specific probe, can be with formaldehyde
Chemically react, generate corresponding hydrazone, the content of formaldehyde in determinand can be determined by the fluorescence intensity for detecting hydrazone.Substantially
Assay method is：It is specificity with 20~50 μM of naphthalimide derivatives in the acetonitrile containing 5% acetic acid under room temperature condition
Probe, the acetonitrile solution of formaldehyde is added in probe system, determines solution fluorescence intensity, is contained as formaldehyde according to determination data
The evaluation index of amount.
Concrete application of the fluorescent test paper of energy Rapid Detection of Formaldehyde of the present invention in detection formaldehyde in air：First will be contained
The air of aldehyde is passed into acetonitrile solution, after treating that formaldehyde is substantially soluble in acetonitrile, this is dissolved in and is dripped on fluorescent test paper, then
Whether the viewed under ultraviolet radiation by fluorescent test paper in 365nm wavelength there is chartreuse fluorescence.Judgement air is whether there is according to fluorescence
In whether contain formaldehyde.
The concrete application of fluorescent test paper formaldehyde in water is detected of energy Rapid Detection of Formaldehyde of the present invention：The aqueous solution is dense
Then contracting is dripped on fluorescent test paper with improving concentration of formaldehyde, and then the viewed under ultraviolet radiation by fluorescent test paper in 365nm wavelength is
No generation chartreuse fluorescence.Whether contain formaldehyde in whetheing there is judgement water according to fluorescence.
The beneficial effects of the invention are as follows：Prepared fluorescent test paper load can carry out having for quick specific reaction with formaldehyde
Machine fluorescence probe naphthalimide derivative particularly N- amino -4- (1- piperazinyls) -1,8- naphthalimides, by fluorescence signal
Producing PARA FORMALDEHYDE PRILLS(91,95) carries out qualitative detection, can carry out fast qualitative detection to the formaldehyde in water or air.The fluorescence for being loaded is visited
Pin is 4 naphthalimide derivatives containing different substituents group, and with high specific, detection process will not receive other components
Interference, and sensitivity is high, with good fluorescence emission spectral property (400~500nm).In addition the fluorescence probe is inexpensively easy
, can be obtained through chemical synthesis, and synthesis technique is simple and easy to apply.Further, provided by the present invention for the glimmering of detection formaldehyde
Light test paper is easily prepared, easy to use, formaldehyde that can be in quick detection environment.
Brief description of the drawings
Fig. 1 is N- amino -4- (1- piperazinyls) -1,8- naphthalimides1H NMR spectras.
Fig. 2 is the fluorescent test paper photo of Rapid Detection of Formaldehyde of the present invention.
Fig. 3 is selective collection of illustrative plates of N- amino -4- (1- the piperazinyls) -1,8- naphthalimides to different material
Wherein：1 to 9 is respectively：1：Probe N- amino -4- (1- piperazinyls) -1,8- naphthalimides, 2：Formaldehyde, 3：Acetaldehyde,
4：2,4- 4-dihydroxy benzaldehydes, 5：Terephthalaldehyde, 6：P-methoxybenzal-dehyde, 7：Trichloroacetaldehyde, 8：M-hydroxybenzaldehyde, 9：
Parahydroxyben-zaldehyde.
Fig. 4 is the linear relationship data of N- amino -4- (1- piperazinyls) -1,8- naphthalimides and formaldehyde.
Fig. 5 is the photo of fluorescent test paper PARA FORMALDEHYDE PRILLS(91,95) real-time monitoring of the present invention
Wherein：A holes are：Control point (acetonitrile containing 5% acetic acid drips to the point formed on test paper), B holes are：The acetonitrile of formaldehyde
Solution drips to the point formed on test paper, and C holes are：Imaging of the corresponding A under 395nm irradiations, unstressed configuration, D holes are：Correspondence B exists
Imaging under 395nm irradiations, there is fluorescence.
Specific embodiment
With reference to embodiment and accompanying drawing, the present invention will be further described, the naphthalimide derivative with N- amino-
As a example by 4- (1- piperazinyls) -1,8- naphthalimides, but it is not limited only to this.
Embodiment 1：The preparation of N- amino -4- (1- piperazinyls) -1,8- naphthalimides
By hydrazine hydrate (80%, 62.5mg, 1mmol), the bromo- 1,8- naphthalic anhydrides (276mg, 1mmol) of 4- and ethanol
(10mL) is added in 50mL single-necked flasks, is flowed back 4 hours, is filtered after being cooled to room temperature, and drying obtains light gray solid 240mg.
This solid and Piperazine anhydrous (258mg, 3mmol), glycol monoethyl ether (10mL) are added in 50mL single-necked flasks, nitrogen is protected
The lower backflow of shield 6 hours, vacuum distillation obtains dark brown viscous solid after being cooled to room temperature.
Column chromatography (eluant, eluent is the methyl alcohol containing 5% triethylamine) purifies this sticky solid, obtains yellow solid.Gained is yellow
Color solid and 10mL distilled water, 5mL methyl alcohol are added in 50mL single port bottles, are stirred 24 hours at room temperature, and filtering is dried pale yellow
Color product, yield 67%.The probe1H NMR spectras are shown in Fig. 1.
1H NMR(DMSO,400MHz):δ 8.45 (t, J=7.6Hz, 2H), 8.37 (d, J=8.0Hz, 1H), 7.79 (t, J
=8.4Hz, 1H), 7.27 (d, J=7.6Hz, 1H), 5.76 (s, 2H), 3.15 (s, 4H), 3.00 (s, 4H), 2.43 (s, 1H)
.13C NMR(DMSO-d6,400MHz):δ160.9,155.9,132.7,131.2,128.1,126.7,125.7,122.6,
115.9,52.2,44.8.HRMS(ESI):[M+H]+m/z 297.1347,calcd for C16H17N4O2 +297.1346。
Embodiment 2：The preparation of the fluorescent test paper of Rapid Detection of Formaldehyde of the present invention
(1) N- amino -4- (1- piperazinyls) -1,8- naphthalimide solution for being solvent compound concentration as 1mM with methyl alcohol；
(2) blackish green accurate pH test paper (length × width x thickness is 75mm × 10mm × 0.7mm) is immersed in step (1) system
In standby solution, take out afterwards within 10 minutes, dry at room temperature, that is, obtain blackish green, the non-blooming energy quick detection under uviol lamp
The fluorescent test paper (see Fig. 2) of formaldehyde.
Embodiment 3:Selectivity of N- amino -4- (1- the piperazinyls) -1,8- naphthalimides to different material
8 parts of the 10 of 5mL μM of N- amino -4- (1- piperazinyls) -1,8- naphthalimide probe acetonitrile solutions are prepared in advance (to contain
5% acetic acid), then respectively to sequentially added in 8 parts of systems 50 μ L concentration be 10mM formaldehyde, acetaldehyde, 2,4- dihydroxy
Benzaldehyde, terephthalaldehyde, P-methoxybenzal-dehyde, trichloroacetaldehyde, m-hydroxybenzaldehyde and parahydroxyben-zaldehyde acetonitrile solution.
Then fluoroscopic examination (λ is carried outEx=380nm, λEm=513nm)；Fluorescence intensity in each system is calculated, Fig. 3 is as a result seen.
Embodiment 4：The linear relationship of N- amino -4- (1- piperazinyls) -1,8- naphthalimides and formaldehyde
The acetonitrile solution system of the formaldehyde that 1mL concentration is 0~5mM gradients is prepared, it is 50 then respectively to add 9mL concentration
μM probe acetonitrile solution (contain 5% acetic acid), carry out fluoroscopic examination (λEx=380nm, λEm=513nm), it is glimmering in each system of calculating
Luminous intensity, sets up fluorescence intensity and concentration of hydrogen sulfide standard curve, and standard curve is shown in Fig. 4.
The Monitoring lower-cut of fluorescence probe N- amino -4- (1- piperazinyls) -1,8- naphthalimide PARA FORMALDEHYDE PRILLS(91,95)s of the present invention is
0.53ppm (S/N=3).
Embodiment 5：The application of the fluorescent test paper of Rapid Detection of Formaldehyde of the present invention
Fluorescence probe N- amino -4- (1- piperazinyls) -1,8- naphthalimides have faint fluorescence, but itself and formaldehyde in itself
The product hydrazone of reaction has very strong fluorescence.
Air containing formaldehyde is passed into acetonitrile solution (containing 5% acetic acid), after treating that formaldehyde is substantially soluble in acetonitrile,
This is dissolved in and is dripped on fluorescent test paper, then whether the viewed under ultraviolet radiation by fluorescent test paper in 365nm wavelength occurs light yellow green
Color fluorescence.Whether contain formaldehyde in whetheing there is judgement air according to fluorescence.If so, formaldehyde can react shape with the probe on test paper
Into a point for chartreuse (see Fig. 5).Wherein：A is：Control point (acetonitrile containing 5% acetic acid drips to the point formed on test paper),
B is：The acetonitrile solution of formaldehyde drips to the point formed on test paper, and C is：Imaging of the corresponding A under 395nm irradiations, unstressed configuration, D is：
Imagings of the correspondence B under 395nm irradiations, there is fluorescence.
Claims (4)
1. it is a kind of can Rapid Detection of Formaldehyde fluorescent test paper, by the unstressed configuration brightening agent of load fluorescence probe naphthalimide derivative
Test paper is constituted, it is characterised in that：The fluorescent test paper for blackish green, length × width x thickness size for 100~75mm × 15~8mm ×
1~0.5mm, the naphthalimide derivative content loaded on every fluorescent test paper is not less than 0.01mg；Wherein it is used for the examination of matrix
Paper is blackish green accurate pH test paper, and the naphthalimide derivative for loading thereon is N- amino -4- (1- piperazinyls) -1,8- naphthoyls
Imines, or N- amino -4- (1- piperidyls) -1,8- naphthalimides, or N- amino -4- (1- pyrrolidinyls) -1,8- naphthalimides.
2. it is according to claim 1 can Rapid Detection of Formaldehyde fluorescent test paper, it is characterised in that：The fluorescent test paper size
Length × width x thickness is 75mm × 10mm × 0.7mm, and the naphthalimide derivative is N- amino -4- (1- piperazinyls) -1,8- naphthalenes
Acid imide.
3. described in claim 1 can Rapid Detection of Formaldehyde fluorescent test paper preparation method, step is：
(1) N- amino -4- (1- piperazinyls) -1, the 8- naphthalimides for being solvent compound concentration as 1mM with methyl alcohol, or N- amino -
4- (1- piperidyls) -1,8- naphthalimides, or N- amino -4- (1- pyrrolidinyls) -1,8- naphthalimide solution；
(2) blackish green accurate pH test paper is immersed in during step (1) prepares solution, is taken out afterwards within 10 minutes, dried at room temperature,
Obtain blackish green, the non-blooming energy Rapid Detection of Formaldehyde under uviol lamp fluorescent test paper.
4. the application of fluorescent test paper formaldehyde in detection air or water of energy Rapid Detection of Formaldehyde described in claim 1 or 2.
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105372217B (en) * | 2015-11-17 | 2018-03-27 | 济南大学 | A kind of formaldehyde fluorescence probe and preparation method thereof, application |
| CN106008342B (en) * | 2016-05-20 | 2018-08-21 | 济南大学 | A kind of fluorescence probe and preparation method thereof detecting formaldehyde in cytase body |
| CN109384719B (en) * | 2017-08-10 | 2021-11-05 | 湖南超亟检测技术有限责任公司 | Fluorescent molecular probe for detecting formaldehyde, synthetic method, preparation and application of test paper |
| CN107607529B (en) * | 2017-08-18 | 2019-12-06 | 广东省药品检验所（广东省药品质量研究所、广东省口岸药品检验所） | Rapid screening method for formaldehyde in perfume |
| CN107478632B (en) * | 2017-09-22 | 2019-12-24 | 南昌航空大学 | Method for detecting pH value through fluorescence of pH test paper |
| CN108444962B (en) * | 2018-03-05 | 2021-01-12 | 北京化工大学 | Perylene-based formaldehyde colorimetric probe and formaldehyde fluorescent test paper, and preparation method and use method thereof |
| CN110836882B (en) * | 2019-11-22 | 2022-05-10 | 曲阜师范大学 | Adopts N-P-4-HN @ UiO-66-NH2Method for determining HCHO content of composite material |
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