CN110596067A - Formaldehyde detection method - Google Patents
Formaldehyde detection method Download PDFInfo
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- CN110596067A CN110596067A CN201910958486.2A CN201910958486A CN110596067A CN 110596067 A CN110596067 A CN 110596067A CN 201910958486 A CN201910958486 A CN 201910958486A CN 110596067 A CN110596067 A CN 110596067A
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The invention relates to a method for detecting formaldehyde, which takes a compound with a structure shown as a formula I as a fluorescent color developing agent of saccharin sodium. The formaldehyde detection method provided by the invention is convenient and easy to implement, high in sensitivity and strong in anti-interference performance, and can be used for quickly detecting formaldehyde.
Description
Technical Field
The invention relates to a method for detecting formaldehyde by fluorescence color development, belonging to the technical field of detection.
Background
Formaldehyde is widely used in the fields of food industry, textile industry, construction industry, chemical engineering, pharmaceutical engineering and the like. However, excessive intake of exogenous formaldehyde can seriously harm human health. Formaldehyde was identified in 2004 by the international agency for research on cancer (IARC) as a class 1 carcinogen. The world health organization international agency for research on cancer (IARC) announced in its publication No. 153 in 2004, 6 months that formaldehyde rose from 2 classes of carcinogens to 1 class of carcinogens. Chronic respiratory diseases, nasopharyngeal carcinoma, colon cancer, brain tumor, cell nucleus gene mutation and the like can be caused by long-term exposure to low-dose formaldehyde. Therefore, the formaldehyde concentration monitoring device is particularly important for monitoring the formaldehyde concentration of food, air, water quality, building materials, textile materials, daily necessities and the like.
The existing methods for detecting the concentration of formaldehyde mainly comprise ultraviolet spectrophotometry, liquid chromatography, gas chromatography, electrochemical sensor method and the like. The methods for detecting formaldehyde by gas chromatography and liquid chromatography are complicated, expensive in instruments, and poor in specificity, and carbonyl-containing compounds such as acetaldehyde and acetone cause interference. The electrochemical sensor method also has larger interferents to influence the test result, such as volatile gases of phenol and alcohol, and the wind speed also influences the test result in use. The fluorescence color development method has strong specificity and sensitivity, can generally measure the concentration of formaldehyde by using an external standard method, has the characteristics of simplicity, convenience and economy, and is suitable for being popularized to portable colorimetric instruments.
The fluorescence color development test of formaldehyde needs a color developing agent with specificity to formaldehyde, and the national standard GB/T16129-. In the national standard GB/T18204.26-2000 method for measuring formaldehyde in public place air, formaldehyde and 3-methyl-2-benzothiazole hydrazone hydrochloride form oxazine, and the concentration of the formaldehyde is measured by developing blue-green color in the presence of acidic ammonium ferric sulfate. The color development conditions are alkaline and acidic, respectively. For some analytes that are unstable under alkaline or acidic conditions, the above method obviously produces large errors in detection.
Disclosure of Invention
The invention aims to solve the technical problem of providing a formaldehyde detection method which is convenient and easy to implement, can be used under a neutral condition, and has high sensitivity, strong anti-interference performance and high detection speed.
The invention provides a technical scheme for solving the technical problems, which comprises the following steps: a method for detecting formaldehyde, which uses a compound with a structure shown as a formula I as a fluorescent color developing agent of formaldehyde,
the method for detecting the formaldehyde comprises the following specific steps: the fluorescence color developing agent is prepared into an aqueous solution with the concentration of 1 x 10 < -8 > mol/L-1 x 10 < -5 > mol/L, the formaldehyde absorption liquid to be detected is added into the aqueous solution of the fluorescence color developing agent, the fluorescence intensity is detected by adopting a fluorescence photometry, the fluorescence intensity is in direct proportion to the formaldehyde content, and the formaldehyde content in the formaldehyde absorption liquid is judged according to the fluorescence intensity.
The formaldehyde detection method comprises the steps of firstly detecting formaldehyde standard products with different concentrations by using the aqueous solution of the fluorescent color developing agent, drawing a content curve of the standard products, then detecting the formaldehyde absorption liquid to be detected by using the aqueous solution of the fluorescent color developing agent, and calculating the formaldehyde content in the formaldehyde absorption liquid by using a standard curve method.
The concentration of the fluorescent color developing agent in the aqueous solution of the fluorescent color developing agent is 1 × 10-7mol/L～1×10-5mol/L。
The concentration of the fluorescent color developing agent in the aqueous solution of the fluorescent color developing agent is 1 × 10-7mol/L～1×10-6mol/L。
The fluorescence intensity measured by the above-mentioned fluorometric method was measured at 633nm after excitation at 545 nm.
The preparation method of the fluorescent color developing agent comprises the steps of dissolving a compound with a structure shown as a formula II in an organic solvent, adding nitrobenzaldehyde and a catalyst, and reacting to generate a compound with a structure shown as a formula I, wherein the reaction formula is as follows:
the reaction time is 5-24 h, and the reaction temperature is 5-37 ℃.
The catalyst is sodium triacetate borohydride, and the organic solvent is tetrahydrofuran.
The molar ratio of the compound with the structure shown as the formula II to the p-nitrobenzaldehyde is 1:1 to 1:10, and the molar ratio of the catalyst to the compound with the structure shown as the formula II is 1: 0.5-1: 1.5.
The invention has the positive effects that:
(1) the formaldehyde detection method adopts a novel fluorescent color developing agent, and the fluorescent color developing phenomenon can occur when the novel fluorescent color developing agent interacts with formaldehyde. The purpose of detecting formaldehyde is achieved. Forms fluorescent association with formaldehyde, and can be excited by 545nm, and the emission peak is 633 nm. The formaldehyde detection method of the invention is used for detecting formaldehyde and other common air pollutants, such as: gas molecules such as sulfur dioxide, acetaldehyde, toluene, ammonia gas, hydrogen sulfide and the like do not generate fluorescence, which shows that the method has a high-selectivity fluorescence color development effect on formaldehyde. The method is convenient and easy to implement, high in sensitivity and strong in anti-interference performance, can be used for quickly detecting the formaldehyde, and is particularly suitable for quickly detecting the formaldehyde content in the air.
(2) The formaldehyde detection method only needs to prepare the fluorescent agent into an aqueous solution according to a certain concentration, and the concentration is preferably 1 x 10-8mol/L～1×10-5And mol/L, the fluorescence intensity can be detected by adopting a fluorescence photometry method, and the content can be drawn by adopting a standard curve method by using a standard substance so as to calculate the specific content.
Drawings
FIG. 1 shows fluorescence spectra of formaldehyde at different concentrations detected by the fluorescent developer of example 1.
FIG. 2 is a fluorescence spectrum of formaldehyde and other interference factors detected using the fluorescent color developer of example 1.
FIG. 3 is a NMR spectrum of a compound of formula I in example 1.
Detailed Description
Example 1
The molecular structure of the fluorescent color developing agent of the embodiment is shown as formula I:
the NMR spectrum of the compound is shown in FIG. 3.
The fluorescent color developing agent of this example is prepared by dissolving 120mg (0.21mmol) of the compound having the structure shown in formula II in 10mL of tetrahydrofuran, sequentially adding 100mg (0.65mmol) of p-nitrobenzaldehyde, 100. mu.L (1.6mmol) of glacial acetic acid and 180mg (0.9mmol) of sodium triacetate borohydride, and stirring at room temperature for 18 hours. Glacial acetic acid is used as a cosolvent of the paranitrobenzaldehyde, and is beneficial to promoting the mixing of the paranitrobenzaldehyde and other substances. The reaction formula is as follows:
after the reaction was complete, 50mL of saturated sodium bicarbonate solution was poured, extracted 4 times with 30mL of ethyl acetate, and the organic phase was dried in vacuo. Washing with water, methanol and anhydrous ether for several times. And (5) drying in vacuum. The yield was 70%.
Wherein, the compound with the structure shown in the formula II is an externally purchased reagent, and the synthetic route of the compound is as follows:
wherein the compound with the structure shown in the formula III is the extract of mangosteen.
Example 2
The preparation method of the fluorescent color developing agent of this embodiment is to dissolve 120mg (0.21mmol) of the compound having the structure shown in formula II in 10mL of tetrahydrofuran, sequentially add 100mg (0.65mmol) of p-nitrobenzaldehyde 180mg (0.9mmol) of sodium triacetate borohydride, and stir at room temperature for 18 hours. After the reaction was complete, 50mL of saturated sodium bicarbonate solution was poured, extracted 4 times with 30mL of ethyl acetate, and the organic phase was dried in vacuo. Washing with water, methanol and anhydrous ether for several times. And (5) drying in vacuum. The yield was 70%.
Example 3
The fluorescent color developing agent of this embodiment is prepared by dissolving 120mg (0.21mmol) of the compound having the structure shown in formula II in 10mL of tetrahydrofuran, sequentially adding 50(0.325mmol) of p-nitrobenzaldehyde, 100. mu.L (1.6mmol) of glacial acetic acid and 180mg (0.9mmol) of sodium triacetate borohydride, and stirring at room temperature for 18 hours. After the reaction was complete, 50mL of saturated sodium bicarbonate solution was poured, extracted 4 times with 30mL of ethyl acetate, and the organic phase was dried in vacuo. Washing with water, methanol and anhydrous ether for several times. And (5) drying in vacuum. The yield was 70%.
Application example
The formaldehyde in this application example was detected by preparing an aqueous solution from the fluorescent color-developing agent synthesized in example 1, the concentration of the fluorescent color-developing agent being 1X 10-6mol/L. Adding formaldehyde with standard concentration, exciting at 545nm, and measuring the intensity of emission peak at 633nm to obtain a fluorescence spectrum, as shown in FIG. 1.
A standard curve was then generated and the concentration gradient set up, see table 1.
TABLE 1 fluorescence absorption curve standard concentration setting table
| Pipe number | 1 | 2 | 3 | 4 | 5 | 6 |
| Formaldehyde content (μ g/mL) | 0.0000 | 0.1196 | 0.2393 | 0.4785 | 0.9570 | 1.4356 |
| Formaldehyde (ug) | 0.0000 | 0.5982 | 1.1964 | 2.3925 | 4.7850 | 7.1778 |
| Absorption number | 0.0720 | 0.4020 | 0.4500 | 0.8280 | 1.3560 | 1.9890 |
The standard curve was obtained as y-0.2473 x +0.1768 with an R value of 0.995 and good linearity. From this, it can be seen that the fluorescence intensity is linearly proportional to the formaldehyde content. Taking the concentration of high and low formaldehyde as 0.1 mug/mL and 1.4 mug/mL respectively, adding a fluorescence color developing agent respectively, testing the absorbance of a fluorescence spectrum, and calculating a theoretical value according to a standard curve. The procedure was repeated 6 times and the precision of the method was determined to obtain the data shown in Table 2. Wherein AVERAGE is the AVERAGE of 6 tests; STDEV is the standard deviation, which reflects the degree of dispersion of the data from the mean; CV is the coefficient of variation, reflecting the precision of the method.
TABLE 2 precision of the detection method at different formaldehyde concentrations
| Numbering | LOW | HIGH |
| 1 | 0.1008 | 1.4529 |
| 2 | 0.0982 | 1.5086 |
| 3 | 0.1008 | 1.5064 |
| 4 | 0.0992 | 1.5071 |
| 5 | 0.1045 | 1.4607 |
| 6 | 0.1010 | 1.4986 |
| AVERAGE | 0.1000 | 1.4890 |
| STDEV | 0.0020 | 0.0184 |
| CV | 1.97％ | 1.23％ |
In the data in table 2, it is proved that the CV value of the method reaches below 2% at both high concentration and low concentration of the standard curve, which indicates that the precision of the method for measuring the formaldehyde concentration is good.
The formaldehyde detection method of the application example is adopted to respectively detect the fluorescence intensity of the solution containing sulfur dioxide, acetaldehyde, toluene, ammonia gas and hydrogen sulfide. Wherein the concentration of the solution containing sulfur dioxide, acetaldehyde, toluene, ammonia gas and hydrogen sulfide is 1 × 10–5mol/L, concentration of formaldehyde solution is 1X 10–6The obtained fluorescence spectrum is shown in FIG. 2. Therefore, the interference factors such as sulfur dioxide, acetaldehyde, toluene, ammonia gas and hydrogen sulfide do not interfere with the fluorescence response to formaldehyde.
The reagents used in the present invention are chemically pure at concentrations not otherwise specified.
It should be understood that the above examples are only for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And such obvious variations or modifications which fall within the spirit of the invention are intended to be covered by the scope of the present invention.
Claims (10)
1. A formaldehyde detection method is characterized in that: a compound with a structure shown as a formula I is used as a fluorescent color developing agent of formaldehyde,
。
2. formaldehyde according to claim 1The detection method is characterized by comprising the following specific steps: the fluorescent color developing agent is prepared to have the concentration of 1 × 10-8mol/L～1×10-5Adding the formaldehyde absorption liquid to be detected into the aqueous solution of the fluorescent color developing agent in mol/L aqueous solution, detecting the fluorescence intensity by adopting a fluorescence photometry, wherein the fluorescence intensity is in direct proportion to the formaldehyde content, and judging the formaldehyde content in the formaldehyde absorption liquid according to the fluorescence intensity.
3. The method for detecting formaldehyde according to claim 2, wherein: the method comprises the steps of firstly detecting formaldehyde standard products with different concentrations by using the aqueous solution of the fluorescent color developing agent, drawing a content curve of the standard products, then detecting the formaldehyde absorption liquid to be detected by using the aqueous solution of the fluorescent color developing agent, and calculating the formaldehyde content in the formaldehyde absorption liquid by using a standard curve method.
4. The method for detecting formaldehyde according to claim 2, wherein: the concentration of the fluorescent color developing agent in the aqueous solution of the fluorescent color developing agent is 1 multiplied by 10-7mol/L～1×10-5mol/L。
5. The method for detecting formaldehyde according to claim 4, wherein: the concentration of the fluorescent color developing agent in the aqueous solution of the fluorescent color developing agent is 1 multiplied by 10-7mol/L～1×10-6mol/L。
6. The method for detecting formaldehyde according to any one of claims 1 to 5, wherein: the fluorescence intensity measured by the fluorometry method was measured at 545nm excitation and 633 nm.
7. The method for detecting formaldehyde according to any one of claims 1 to 5, wherein: the preparation method of the fluorescent color developing agent comprises the steps of dissolving a compound with a structure shown as a formula II in an organic solvent, adding nitrobenzaldehyde and a catalyst, and reacting to generate a compound with a structure shown as a formula I, wherein the reaction formula is as follows:
。
8. the method for detecting formaldehyde according to claim 7, wherein: the reaction time is 5-24 h, and the reaction temperature is 5-37 ℃.
9. The method for detecting formaldehyde according to claim 7, wherein: the catalyst is sodium triacetate borohydride, and the organic solvent is tetrahydrofuran.
10. The method for detecting formaldehyde according to claim 7, wherein: the molar ratio of the compound with the structure shown as the formula II to the p-nitrobenzaldehyde is 1:1 to 1:10, and the molar ratio of the catalyst to the compound with the structure shown as the formula II is 1: 50-1: 5000.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004200A (en) * | 2021-02-03 | 2021-06-22 | 台州学院 | Formaldehyde concentration and pH value dual-response type probe based on naphthalimide derivative, and preparation and application thereof |
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| CN106802291A (en) * | 2017-01-16 | 2017-06-06 | 杭州柘大飞秒检测技术有限公司 | A kind of detection method of saccharin sodium |
| CN108219776A (en) * | 2018-02-05 | 2018-06-29 | 三峡大学 | A kind of enhanced fluorescence probe, preparation method and the application on detection formaldehyde |
| US20180215773A1 (en) * | 2015-08-21 | 2018-08-02 | The Regents Of The University Of California | Homoallylamines as formaldehyde-responsive triggers |
| CN108484414A (en) * | 2018-05-03 | 2018-09-04 | 北京化工大学 | A kind of formaldehyde fluorescence probe and formaldehyde examination piece and preparation method thereof based on tetraphenylethylene, formaldehyde examination piece application method |
| CN110117229A (en) * | 2018-02-05 | 2019-08-13 | 中国医学科学院药物研究所 | Fluorescent probe and the preparation method and application thereof |
-
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- 2019-10-10 CN CN201910958486.2A patent/CN110596067A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180215773A1 (en) * | 2015-08-21 | 2018-08-02 | The Regents Of The University Of California | Homoallylamines as formaldehyde-responsive triggers |
| CN106802291A (en) * | 2017-01-16 | 2017-06-06 | 杭州柘大飞秒检测技术有限公司 | A kind of detection method of saccharin sodium |
| CN108219776A (en) * | 2018-02-05 | 2018-06-29 | 三峡大学 | A kind of enhanced fluorescence probe, preparation method and the application on detection formaldehyde |
| CN110117229A (en) * | 2018-02-05 | 2019-08-13 | 中国医学科学院药物研究所 | Fluorescent probe and the preparation method and application thereof |
| CN108484414A (en) * | 2018-05-03 | 2018-09-04 | 北京化工大学 | A kind of formaldehyde fluorescence probe and formaldehyde examination piece and preparation method thereof based on tetraphenylethylene, formaldehyde examination piece application method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113004200A (en) * | 2021-02-03 | 2021-06-22 | 台州学院 | Formaldehyde concentration and pH value dual-response type probe based on naphthalimide derivative, and preparation and application thereof |
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