CN106187729A - A kind of hydrazine hydrate detection filter paper bar and application thereof - Google Patents

A kind of hydrazine hydrate detection filter paper bar and application thereof Download PDF

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Publication number
CN106187729A
CN106187729A CN201610502439.3A CN201610502439A CN106187729A CN 106187729 A CN106187729 A CN 106187729A CN 201610502439 A CN201610502439 A CN 201610502439A CN 106187729 A CN106187729 A CN 106187729A
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filter paper
paper bar
hydrazine hydrate
salicylide
present
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CN106187729B (en
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李振
宋雨晨
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Wuhan University WHU
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Physics & Mathematics (AREA)
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  • Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

The present invention relates to a kind of hydrazine hydrate detection filter paper bar and application thereof, belong to hydrazine hydrate detection field.Described filter paper bar is impregnated with 4 (4 bromine butoxy) salicylide.The present invention is from 4 hydroxyl salicylides and Isosorbide-5-Nitrae dibromobutane, obtains 4 (4 bromine butoxy) salicylide by a step nucleophilic substitution, then filter paper bar is immersed in its ethanol solution, dries up and obtains detecting hydrazine hydrate filter paper bar.The filter paper bar of the present invention for hydrazine hydrate have obvious, quickly respond, selectivity is high, easy to use, applied widely, and the method with emergency monitoring hydrazine hydrate in real time that compensate for lacks.And the filter paper bar of the present invention is easy to make, low cost.

Description

A kind of hydrazine hydrate detection filter paper bar and application thereof
Technical field
The present invention relates to a kind of hydrazine hydrate detection filter paper bar and application thereof, belong to hydrazine hydrate detection field.
Background technology
Hydrazine hydrate is colourless transparent oil liquid also known as hydrazine hydrate, sterling, has light ammonia taste, and reproducibility is extremely strong.Hydrazine hydrate For a kind of important fine chemical material, it is mainly used in synthesizing the foaming agent such as D1PA, AC, TSH；Can also be used for reactor and boiler Carbon dioxide removal and the cleaning treatment agent of deoxidation；Pesticide producing is raticide, herbicide, plant growing blender etc. produce The important source material of product；Medical industry is used for produce tuberculosis, diabetes medicine；Steam power plant and nuclear power plant are used as Recirculated water anticorrosive additive；In addition 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 refine, novel polymeric initiators.The range of application of hydrazine hydrate is also being continuously increased, but what it had High toxicity attracts attention.Hydrazine hydrate belongs to hypertoxic type material, LD50For 129mg/kg, by sucking, eating, percutaneous The modes such as absorption are taken in, and in the internal metabolic function affecting carbohydrate and fat, have hemolytic, damage liver, Make blood glucose reduction, blood hydropenia, and cause anemia, central nervous system during acute poisoning, can be damaged.Its steam can corrode mucosa, Stimulate corrosion eyes and skin, occur that redness is suppurated.
Detection method for hydrazine hydrate rests on test in laboratory mostly, by potentiostatic method, cyclic voltammetry, ion Chromatography, colorimetry, New UV Spectrophotometric analytic process, to technological means such as methylamino phenenyl formaldehyde spectrophotographys to it matchmakers such as sewage The mensuration of content in Jie.But the method detected by Instrumental Analysis is the longest, complex steps does not have promptness, at present Still the method lacking on-the-spot emergency monitoring.
The features such as fluorescent optical sensor is fast owing to having response, highly sensitive, simple to operate, received greatly in the last few years Pay close attention to.The feature of fluorescent optical sensor makes it be made up the weak point of Instrumental Analysis, meets an urgent need for promptness detection and scene Monitoring has the application in terms of obvious advantage, especially filter paper bar, has tempting prospect especially.But conventional fluorescent sensor Because there is rigid planar structure, intramolecular forms π-π interaction and causes aggregation inducing fluorescent quenching (ACQ) phenomenon, at height The when of concentration or solid-state, fluorescence intensity drastically reduces and even disappears.Although scientists have employed various physically or chemically Method reduce or prevent the gathering of fluorescence molecule, prevent organic fluorescence molecule as introduced spirocyclic ring scaffold or big steric group The multiple methods such as gathering, enhancing Intramolecular electron transfer transition, cross stacking, J-state of aggregation, dipole cross stacking eliminate poly- The impact of collection Fluorescence quenching effect, but less effective and complex steps.
Calendar year 2001, this loyalty academician seminar of Tang reported first one class has the chemical combination of aggregation-induced emission (AIE) character Thing, the luminescence when solution state of this compounds is the most weak or the most luminous, and has high fluorescence quantum yield when solid-state.This luminescence Behavior overcomes the defect of ACQ effect, causes great interest and the extensive concern of people.Systematic research work shows to assemble The mechanism of induced luminescence is in solution state, the nonradiative relaxation that the energy of this quasi-molecule is mainly formed by the rotating manner of aromatic ring Passage dissipates, and during solid-state, owing to Internal Rotations of Molecules is obstructed, nonradiative relaxation channel jam, energy is by fluorescent emission Mode consumes.Aggregation-induced emission effect has the spy of good prospect, especially its solid luminescent in fluorescent optical sensor field Property, more conform to the application of filter paper bar sensing, have simpler operability, Portability than liquid sensing, apply in reality In have more preferable prospect.
Summary of the invention
The technical problem to be solved in the present invention is to provide test strip and the application thereof of a kind of hydrazine hydrate.Present invention profit By the characteristic of aggregation-induced emission effect solid luminescent, with the form of filter paper bar, hydrazine hydrate is detected cleverly, have and Time, easy, efficiently, the characteristic such as portable.
The technical scheme realizing the object of the invention is:
A kind of hydrazine hydrate detection filter paper bar, is impregnated with 4-(4-bromine butoxy)-salicylide in described filter paper bar.
The present invention hydrazine hydrate detection filter paper bar, by filter paper bar in 4-(4-bromine butoxy)-salicylide solution brewed after Dry up gained.
Present invention also offers the preparation method of above-mentioned filter paper bar, comprise the following steps:
(1) under condition of nitrogen gas, after 4-hydroxyl salicylide acetone solution, potassium carbonate and 18-crown-6,50 DEG C reaction are added After 1 hour, add Isosorbide-5-Nitrae-dibromobutane, sucking filtration use washing with acetone filter cake after react two hours, the pale yellow solution obtained use Anhydrous sodium sulfate is dried, with petroleum ether as eluent, product is used silica gel chromatography column purification, vacuum drying, obtains compound 4-(4-bromine butoxy)-salicylide；The structural formula of described compound 4-(4-bromine butoxy)-salicylide is
(2) cutting suitable size filter paper bar, is immersed in the ethanol solution of 4-(4-bromine butoxy)-salicylide
12 hours；After taking-up, hair dryer dries up and continues to employ.
The method that present invention also offers use above-mentioned filter paper bar detection hydrazine hydrate:
Take out filter paper bar, be placed in the solution or the air that need monitoring, take out after 10 to 30 seconds and dry up, use ultra violet lamp Filter paper bar, if there is yellow fluorescence, then there is hydrazine hydrate in explanation, otherwise then without.
The present invention utilizes 4-(4-bromine butoxy)-salicylide not possess fluorescence, but generates AIE after reacting with hydrazine hydrate and divide , there is yellow fluorescence in son, is the process of " turn-on ", it is achieved the sensing to hydrazine hydrate.Raw material 4-(4-bromine butoxy)-water Poplar aldehyde is readily synthesized, and the making of filter paper bar and the process of use are very simple, use condition and range extensive, are the bar of 3-14 at pH All can use under part, sensor monitoring can be carried out for the hydrazine hydrate that (accompanying drawing 2) in (accompanying drawing 1) in solution and air exists, have Good application prospect.
Accompanying drawing explanation
Fig. 1, filter paper bar of the present invention responds for variable concentrations hydrazine hydrate.
Fig. 2, filter paper bar of the present invention is for the response of gaseous state hydrazine hydrate.
Detailed description of the invention
In order to be more fully understood that present disclosure, below in conjunction with specific embodiment, present disclosure is made furtherly Bright, but the protection content of the present invention is not limited to following example.
Raw material used in the embodiment of the present invention can be buied by market, or available methods known in the art synthesize Arrive.
The synthesis of embodiment 1 compound 1 and the preparation of filter paper bar
Synthetic route is as follows:
Under condition of nitrogen gas, after 4-hydroxyl salicylide acetone solution, add potassium carbonate and 18-crown-6,50 degree reaction 1 is little Shi Hou, adds Isosorbide-5-Nitrae-dibromobutane.Sucking filtration use washing with acetone filter cake after reacting two hours.The pale yellow solution obtained is with anhydrous Sodium sulfate is dried, with petroleum ether as eluent, product is used silica gel chromatography column purification, vacuum drying, obtains compound 1, produces Rate is 75%；The structural formula of described 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。
Cutting same size filter paper bar, uniformly immerses (4*10 in compound 1 ethanol solution by filter paper bar-4Mol/L), seal 12 hours are stood after container.Take out filter paper bar with clean tweezers afterwards and dry up with hair-dryer, being placed in vacuum drying oven Take out after being dried 2h, it is not necessary to keep away oxygen lucifuge, preserve stand-by.
After the embodiment of the present invention collects organic facies, it is to use anhydrous Na2SO4It is dried, it would however also be possible to employ other desiccant, only Want to remove the moisture in organic facies and not react with organic facies.
Embodiment 2 compound 1 filter paper bar is for detecting the using method of hydrazine hydrate in solution
Taking out the compound 1 filter paper bar of embodiment 1 preparation preserved, be immersed in containing variable concentrations hydrazine hydrate is to be measured In liquid, or by drop to be measured on filter paper bar.Dry up after waiting 10 to 30 seconds, be placed under fluorescent lamp observation.If there being fluorescence, then deposit At hydrazine hydrate, on the contrary then without, as shown in Figure 1.
Embodiment 3 compound 1 filter paper bar using method of hydrazine hydrate in detected gas is taken out the embodiment 1 preserved and is made Standby compound 1 filter paper bar, is directly placed in air to be measured after 10 to 30 seconds, takes out and is placed under fluorescent lamp observation.If having , then there is hydrazine hydrate in fluorescence, on the contrary then without, as shown in Figure 2.

Claims (3)

1. a hydrazine hydrate detection filter paper bar, is impregnated with 4-(4-bromine butoxy)-salicylide in described filter paper bar.
2. the preparation method of filter paper bar described in claim 1, comprises the following steps:
(1) under condition of nitrogen gas, after 4-hydroxyl salicylide acetone solution, add potassium carbonate and 18-crown-6,50 DEG C reaction 1 is little Shi Hou, adds Isosorbide-5-Nitrae-dibromobutane, and sucking filtration use washing with acetone filter cake after reacting two hours, the pale yellow solution obtained is with anhydrous Sodium sulfate is dried, with petroleum ether as eluent, product is used silica gel chromatography column purification, vacuum drying, obtains compound 4-(4- Bromine butoxy)-salicylide；
(2) cutting suitable size filter paper bar, is immersed in the ethanol solution of 4-(4-bromine butoxy)-salicylide 12 hours； After taking-up, hair dryer dries up and continues to employ.
3. use the method for filter paper bar detection hydrazine hydrate described in claim 1, it is characterised in that:
Take out filter paper bar, be placed in the solution or the air that need monitoring, take out after 10 to 30 seconds and dry up, use ultra violet lamp filter paper Bar, if there is yellow fluorescence, then there is hydrazine hydrate in explanation, otherwise then without.
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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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108033974A (en) * 2018-01-19 2018-05-15 中国石油大学(华东) A kind of fluorescent probe compounds and its preparation method and application

Citations (1)

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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

Patent Citations (1)

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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
XIANHONG HUANG等: "A highly selective fluorescence turn-on detection of cyanide based on the aggregation of tetraphenylethylene molecules induced by chemical reaction", 《CHEM. COMMUN.》 *
周秋兰等: "一种新型水合肼荧光比率探针的合成及应用研究", 《湖南师范大学自然科学学报》 *
魏瑞瑞: "基于聚集诱导荧光的肼二腙类荧光探针和刺激响应材料", 《中国博士学位论文全文数据库 工程科技I辑》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108033974A (en) * 2018-01-19 2018-05-15 中国石油大学(华东) A kind of fluorescent probe compounds and its preparation method and application

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