CN106187729B - A kind of hydrazine hydrate detection filter paper item and its application - Google Patents

A kind of hydrazine hydrate detection filter paper item and its application Download PDF

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CN106187729B
CN106187729B CN201610502439.3A CN201610502439A CN106187729B CN 106187729 B CN106187729 B CN 106187729B CN 201610502439 A CN201610502439 A CN 201610502439A CN 106187729 B CN106187729 B CN 106187729B
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filter paper
paper item
hydrazine hydrate
salicylide
solution
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CN106187729A (en
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李振
宋雨晨
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Wuhan University WHU
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • G01N21/6402—Atomic fluorescence; Laser induced fluorescence
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems

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  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

The present invention relates to a kind of hydrazine hydrate detection filter paper item and its applications, belong to hydrazine hydrate detection field.4- (4- bromine butoxy)-salicylide is impregnated in the filter paper item.The present invention is to obtain 4- (4- bromine butoxy)-salicylide by a step nucleophilic substitution, then filter paper item is immersed in its ethanol solution, drying obtains detection hydrazine hydrate filter paper item from 4- hydroxyl salicylide and Isosorbide-5-Nitrae-dibromobutane.Filter paper item of the invention has obvious, quick response for hydrazine hydrate, and selectivity is high, easy to use, applied widely, compensates for and lacks in real time with the method for emergency monitoring hydrazine hydrate.And filter paper item of the invention is easy to make, it is low-cost.

Description

A kind of hydrazine hydrate detection filter paper item and its application
Technical field
The present invention relates to a kind of hydrazine hydrate detection filter paper item and its applications, belong to hydrazine hydrate detection field.
Background technique
Hydrazine hydrate is also known as hydrazine hydrate, and sterling is colourless transparent oil liquid, there is light ammonia taste, and reproducibility is extremely strong.Hydrazine hydrate For a kind of important fine chemical material, it is mainly used for synthesizing the foaming agents such as D1PA, AC, TSH；It can also be used for reaction kettle and boiler Carbon dioxide removal and deoxidation cleaning treatment agent；It is produced in pesticide producing for raticide, herbicide, plant growth blender etc. The important source material of product；For producing the drug for the treatment of tuberculosis, anti-diabetic in medical industry；It is used as in steam power plant and nuclear power plant Recirculated water anticorrosive additive；Furthermore it can be also used for the products such as rocket fuel, developed dye, rubber chemicals, dyestuff production, Noble metal cleans the purposes such as refining, novel polymeric initiators.The application range of hydrazine hydrate is also being continuously increased, but it has High toxicity attracts attention.Hydrazine hydrate belongs to high poison substance, LD50For 129mg/kg, by sucking, eating, percutaneously The modes such as absorption are taken in, and damage liver with hemolytic in the metabolic function for influencing carbohydrate and fat in vivo, It reduces blood glucose, blood water shortage, and causes anaemia, when acute poisoning can damage central nervous system.Its steam can corrode mucous membrane, , there is redness suppuration in stimulation corrosion eyes and skin.
Laboratory testing is rested on for the detection method of hydrazine hydrate mostly, passes through potentiostatic method, cyclic voltammetry, ion Chromatography, colorimetric method, New UV Spectrophotometric analytic approach, to technological means such as methylamino phenenyl formaldehyde spectrophotometry to it in matchmakers such as sewage The measurement of content in Jie.But it is taken a long time by the method for instrument analysis detection, complex steps, and does not have timeliness, at present Still lack the method for live emergency monitoring.
The features such as fluorescent optical sensor is due to having response fastly, high sensitivity, easy to operate, received greatly in recent years Concern.The characteristics of fluorescent optical sensor, enables it to make up the shortcoming of instrument analysis, meets an urgent need for timeliness detection and scene Monitoring has the application in terms of apparent advantage, especially filter paper item, even more there is tempting prospect.But conventional fluorescent sensor Because intramolecular, which forms π-π interaction, leads to aggregation inducing fluorescent quenching (ACQ) phenomenon, in height there are rigid planar structure When concentration or solid-state, fluorescence intensity, which drastically reduces, even to disappear.Although scientists use it is various physically or chemically Method reduce or prevent the aggregation of fluorescent molecule, such as introducing spirocyclic ring scaffold or big steric group prevents organic fluorescence molecule A variety of methods such as aggregation, enhancing Intramolecular electron transfer transition, cross stacking, J- state of aggregation, dipole cross stacking are poly- to eliminate Collect the influence of Fluorescence quenching effect, but less effective and complex steps.
2001, this loyalty academician seminar of Tang reported a kind of chemical combination with aggregation-induced emission (AIE) property for the first time Object, such compound shine very weak in solution state or do not shine, and in solid-state with high fluorescence quantum yield.This shines Behavior overcomes the defect of ACQ effect, causes the great interest and extensive concern of people.Systematic research work shows to assemble The mechanism of induced luminescence is in solution state, and the energy of such molecule mainly passes through the nonradiative relaxation that the rotating manner of aromatic ring is formed Channel is dissipated, and when solid-state, since Internal Rotations of Molecules is obstructed, nonradiative relaxation channel jam, energy passes through fluorescent emission Mode consumes.Aggregation-induced emission effect has the spy of good prospect, especially its solid luminescent in fluorescent optical sensor field Property, it is more in line with the application of filter paper item sensing, has simpler operability, Portability compared with liquid sensing, in practical application In have better prospect.
Summary of the invention
The technical problem to be solved in the present invention is that providing the test strip and its application of a kind of hydrazine hydrate.Benefit of the invention With the characteristic of aggregation-induced emission effect solid luminescent, cleverly hydrazine hydrate is detected in the form of filter paper item, have and When, it is easy, efficiently, the characteristics such as portable.
Realizing the technical solution of the object of the invention is:
A kind of hydrazine hydrate detects filter paper item, is impregnated with 4- (4- bromine butoxy)-salicylide in the filter paper item.
Hydrazine hydrate of the invention detects filter paper item, by filter paper item in 4- (4- bromine butoxy)-salicylide solution it is brewed after Drying gained.
The present invention also provides the preparation methods of above-mentioned filter paper item, comprising the following steps:
(1) under condition of nitrogen gas, after 4- hydroxyl salicylide acetone solution, potassium carbonate and 6,50 DEG C of 18- crown- reactions is added After 1 hour, be added Isosorbide-5-Nitrae-dibromobutane, reaction two hours after filter and use acetone washing filter cake, obtain pale yellow solution use After anhydrous sodium sulfate is dry, using petroleum ether as eluent, by product silica gel chromatograph column purification, vacuum drying obtains compound 4- (4- bromine butoxy)-salicylide；The structural formula of compound 4- (4- bromine the butoxy)-salicylide is
(2) suitable size filter paper item is cut, is immersed in the ethanol solution of 4- (4- bromine butoxy)-salicylide
12 hours；Hair dryer drying is continued to employ after taking-up.
The present invention also provides the methods for using above-mentioned filter paper item detection hydrazine hydrate:
Filter paper item is taken out, is placed in the solution or air for needing to monitor, drying is taken out after 10 to 30 seconds, with ultraviolet light irradiation Filter paper item illustrates if there is yellow fluorescence there are hydrazine hydrate, on the contrary then nothing.
The present invention does not have fluorescence using 4- (4- bromine butoxy)-salicylide, but divides with AIE is generated after hydration hydrazine reaction There is yellow fluorescence, the as process of " turn-on " in son, realizes the sensing to hydrazine hydrate.Raw material 4- (4- bromine butoxy)-water Poplar aldehyde is readily synthesized, and the production and use process very simple of filter paper item, and use condition is in extensive range, in the item that pH is 3-14 It all can be used, can have under part for hydrazine hydrate existing for (attached drawing 2) carries out sensor monitoring in (attached drawing 1) and air in solution Good application prospect.
Detailed description of the invention
Fig. 1, filter paper item of the present invention respond various concentration hydrazine hydrate.
Fig. 2, response of the filter paper item of the present invention for gaseous state hydrazine hydrate.
Specific embodiment
In order to better understand the content of the present invention, the contents of the present invention are made furtherly combined with specific embodiments below Bright but of the invention protection content is not limited to following embodiment.
Raw material used in the embodiment of the present invention can be bought by market, or can be synthesized with methods known in the art It arrives.
The synthesis of 1 compound 1 of embodiment and the preparation of filter paper item
Synthetic route is as follows:
Under condition of nitrogen gas, after 4- hydroxyl salicylide acetone solution, potassium carbonate is added and 6,50 degree of 18- crown- reactions 1 are small Isosorbide-5-Nitrae-dibromobutane is added in Shi Hou.It is filtered after reaction two hours and with acetone washing filter cake.Obtained pale yellow solution is with anhydrous After sodium sulphate is dry, using petroleum ether as eluent, by product silica gel chromatograph column purification, vacuum drying obtains compound 1, produces Rate is 75%；The structural formula of the compound 1 is 1H-NMR(300MHz,CDCl3)δ(ppm):11.49 (s,1H),9.72(s,1H),7.45-7.42(d,1H),6.55-6.52(d,1H),6.41(s,1H),4.07-4.03(t,2H), 3.51-3.47(t,2H),2.09-1.95(m,4H)；1C-NMR(300MHz,CDCl3)δ(ppm):166.30,164.71, 135.52,115.42,108.86,101.35,67.67,33.38,29.49,27.83。
Identical size filter paper item is cut, filter paper item is uniformly immersed into (4*10 in 1 ethanol solution of compound-4Mol/L), seal 12 hours are stood after container.Filter paper item is taken out with clean tweezers afterwards and is dried up with hair dryer, and juxtaposition is in a vacuum drying oven It takes out after dry 2h, is protected from light without keeping away oxygen, saved stand-by.
It is to use anhydrous Na after collecting organic phase in the embodiment of the present invention2SO4It is dry, other desiccant can also be used, only Want to remove the moisture in organic phase and not with organic phase reaction.
2 compound of embodiment, 1 filter paper item is used to detect the application method of hydrazine hydrate in solution
1 filter paper item of compound prepared by the embodiment 1 saved is taken out, the to be measured of the hydrazine hydrate containing various concentration is immersed in In liquid, or by drop to be measured on filter paper item.It is dried up after waiting 10 to 30 seconds, is placed under fluorescent lamp and observes.If there is fluorescence, deposit In hydrazine hydrate, on the contrary then nothing, as shown in Figure 1.
3 compound of embodiment, 1 filter paper item takes out the embodiment 1 saved for the application method of hydrazine hydrate in detection gas and makes Standby 1 filter paper item of compound, directly places it in air to be measured after 10 to 30 seconds, and taking-up, which is placed under fluorescent lamp, to be observed.If having , then there is hydrazine hydrate in fluorescence, on the contrary then nothing, as shown in Figure 2.

Claims (3)

1. a kind of hydrazine hydrate detects filter paper item, 4- (4- bromine butoxy)-salicylide is impregnated in the filter paper item.
2. the preparation method of filter paper item described in claim 1, comprising the following steps:
(1) under condition of nitrogen gas, after 4- hydroxyl salicylide acetone solution, potassium carbonate is added and 6,50 DEG C of 18- crown- reactions 1 are small Isosorbide-5-Nitrae-dibromobutane is added in Shi Hou, filters after reaction two hours and with acetone washing filter cake, and obtained pale yellow solution is with anhydrous After sodium sulphate is dry, using petroleum ether as eluent, by product silica gel chromatograph column purification, vacuum drying obtains compound 4- (4- Bromine butoxy)-salicylide；
(2) suitable size filter paper item is cut, 12 hours in the ethanol solution of 4- (4- bromine butoxy)-salicylide are immersed in； Hair dryer drying is continued to employ after taking-up.
3. using the method for the detection hydrazine hydrate of filter paper item described in claim 1, it is characterised in that:
Filter paper item is taken out, is placed in the solution or air for needing to monitor, drying is taken out after 10 to 30 seconds, with ultraviolet light irradiation filter paper Item illustrates if there is yellow fluorescence there are hydrazine hydrate, on the contrary then nothing.
CN201610502439.3A 2016-06-29 2016-06-29 A kind of hydrazine hydrate detection filter paper item and its application Active CN106187729B (en)

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CN108033974B (en) * 2018-01-19 2019-05-07 中国石油大学(华东) A kind of fluorescent probe compounds and its preparation method and application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150192589A1 (en) * 2014-01-08 2015-07-09 Agency For Science, Technology And Research Method using fluorescent turn-on probes for cell-specific detection

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Publication number Priority date Publication date Assignee Title
US20150192589A1 (en) * 2014-01-08 2015-07-09 Agency For Science, Technology And Research Method using fluorescent turn-on probes for cell-specific detection

Non-Patent Citations (3)

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Title
A highly selective fluorescence turn-on detection of cyanide based on the aggregation of tetraphenylethylene molecules induced by chemical reaction;Xianhong Huang等;《Chem. Commun.》;20121231;第48卷;第12195-12197页 *
一种新型水合肼荧光比率探针的合成及应用研究;周秋兰等;《湖南师范大学自然科学学报》;20150531;第38卷(第3期);第48-52页 *
基于聚集诱导荧光的肼二腙类荧光探针和刺激响应材料;魏瑞瑞;《中国博士学位论文全文数据库 工程科技I辑》;20140715(第7期);摘要 *

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