CN106645488A - Method used for measuring content of salicylaldoxime in water environment - Google Patents
Method used for measuring content of salicylaldoxime in water environment Download PDFInfo
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Abstract
The invention discloses a method used for measuring the content of salicylaldoxime in water environment. The method comprises following steps: 1, acetylbenzonitrile standard solutions of different concentration are prepared, and are subjected to gas chromatographic detection so as to obtain the ratio k of the response peak area to the concentration of acetylbenzonitrile; 2, a water solution containing salicylaldoxime is collected, pH value is adjusted to be higher than 7, an excess acetylation reagent and an organic solvent capable of separating from water are added for acetylation, and after reaction, an obtained organic phase is washed with water so as to remove the excess acetylation reagent; 3, the organic phase processed via washing is delivered into a bottle for gas chromatographic detection, and the concentration of salicylaldoxime in the water solution is calculated based on measure peak area and the ratio k. The method is high in accurate; the average relative standard deviation ranges from 2.1 to 8.4%; recovery rate is high; average recovery rate ranges from 88.7 to 92.7%; detection limit is as low as 2.13<mu>g/L; operation is convenient; sensitivity and repeatability are high; and quantification is accurate.
Description
Technical field
The present invention relates to a kind of method for determining salicylaldoxime content in water environment, belongs to sewage detection analytical technology neck
Domain.
Background technology
Salicylaldoxime contains multiple electron donors, with very strong coordination ability, possesses certain collecting ability and good
Selectivity, there is irreplaceable effect in Rare Earth Mine, the floatation process of oxide ore, be a kind of efficiency high, it is selective compared with
Good flotation collecting agent.Salicylaldoxime can with mineral surfaces selectively acting, so as to improve the hydrophobic performance of mineral surfaces,
Mineral are enable to be adsorbed in bubble surface and float.Therefore, salicylaldoxime plays conclusive effect in the flotation for realize mineral.
Meanwhile, salicylaldoxime also plays important purposes in terms of Pt, Cu, Zn, Ni and Pb sensitive analysis reagent is determined.On the other hand,
Salicylaldoxime is a class novel I II class antiarrhythmic drug, and through molecule is derivative etc., means can become a class efficiently, Gao Xuan
Estrogen receptor-β (ER β) selective agonist of selecting property, potential value of the salicylaldoxime in terms of biological medicine also excites section
The interest of scholars.
Salicylaldoxime is also generated while the life production to people brings contribution to ecological environmental and human health impacts
Threaten.In medicine production process, part salicylaldoxime can enter environment with waste water, its rat oral minimum lethal dose (MLD) 400mg/
kg.In terms of flotation, a remaining salicylaldoxime part can be entered in flotation concentrate and mine tailing after flotation, chelating moiety weight
Metal, affects the occurrence status and transportion and transformation of heavy metal, a part to increase concentration by migration, conversion and concentration
Plus tens times or even hundreds of times, enter in river, soil through various modes, eventually enter into human body, it is strong to environment and human body
Health is a kind of potential threat.Thus, set up a kind of quick, sensitive salicylaldoxime detection method dirty for smelting medicament is selected in environment
Dye monitoring and pollution source apportionment are significant.It is individually less to the research of salicylaldoxime both at home and abroad at present, be essentially all
For the research in terms of its mechanism of action, still lack a kind of effective salicylaldoxime quantitative approach.
The content of the invention
The purpose of present invention invention is to provide a kind of quantitative analysis method of salicylaldoxime in sewage, to help Xuan Ye enterprises
Monitor its smelting process Chinese medicine utilization rate and help environmental monitoring department comprehensive monitoring to select the discharge of industry enterprise pollution material
Amount.
The technical scheme is that, there is provided a kind of method for determining salicylaldoxime content in water environment, including following step
Suddenly：
(1) the acetylbenzene formonitrile HCN standard liquid of variable concentrations is prepared, gas chromatographic detection is carried out, acetylbenzene first is obtained
The response peak area of nitrile and the ratio k of its concentration；
(2) aqueous solution containing salicylaldoxime is taken, the aqueous solution is adjusted in alkalescence, excessive acetylation reagent and energy is added
Acetylization reaction is carried out with the organic solvent of water stratification；After the completion of reaction, wash organic phase and remove excessive acetylation reagent；
The process of liquid-liquid extraction can be completed while carrying out acetylization reaction；
(3) organic phase after water intaking is washed is placed in sample injection bottle, carries out gas chromatographic detection；According to measuring peak area and ratio
K calculates the concentration of salicylaldoxime in aqueous solution.
Preferably, in step (2), the pH of the aqueous solution is adjusted in alkalescence using sodium carbonate or sodium acid carbonate.Sodium carbonate and carbon
Sour hydrogen sodium can not only provide alkaline environment, can to generate carbon dioxide with the reaction of the acetylation reagent such as acetic anhydride, two
The gas of carbonoxide rises, and can promote the mixing of two-phase, so as to carry out while realizing derivatization with extraction.
Preferably, the concentration of sodium carbonate or sodium acid carbonate is 4%-6% (m/v, g/mL), most preferably 5% (m/ in the aqueous solution
V, g/mL).
Preferably, in step (2), before adding acetylation reagent, inorganic salts are added in aqueous, it is water-soluble for adjusting
Liquid ionic strength, wherein inorganic salts are to utilize salting-out effect, are easy to material to be transferred in organic phase.
Preferably, the inorganic salts are sodium chloride, and the concentration of sodium chloride is 0.5%-2% (m/v, g/mL) in the aqueous solution,
Most preferably 0.5% (m/v, g/mL).
Preferably, in step (2), acetylation reagent is acetic anhydride.Acetic anhydride is relatively inexpensive acetylation reagent, also may be used
To select other acetylation reagents, such as：TFAA.
Preferably, in step (2), the proportion of the organic solvent is lighter than water, consequently facilitating sampling.
Preferably, the selection of organic solvent will ensure good with the layered effect of water, good to target substance dissolubility, extract second
Acyl group benzonitrile is complete, and chromatographic behavior is good.The organic solvent is preferred fragrance hydro carbons and cyclic hydrocar-bons organic solvent, especially
It is cycloalkane organic solvent, specifically, the optional toluene of organic solvent or hexamethylene, preferred hexamethylene.
Preferably, in step (2), 0.8-2mL acetic anhydrides and 4-5mL organic solvents are added in the aqueous solution per 25mL, is had
Machine solvent is toluene or hexamethylene.
Preferably, the condition of gas chromatographic detection is：Chromatographic apparatus is Agilent 7890A gas-chromatographies, and chromatographic column is
HP-5MS, 30m × 0.25 μm of 250 μ m；Heating schedule is 80 DEG C of initial temperature, keeps 5min, then is raised to 120 with 10 DEG C/min speed
DEG C, 1min is kept, finally 180 DEG C are raised to 5 DEG C/min speed, keep 1min；Injector temperature is 200 DEG C；Detector is
ECD, 220 DEG C of temperature；Splitless injecting samples, carrier gas is nitrogen, flow velocity 1.0mL/min, the μ L of sample size 1.0.
Salicylaldoxime is detected using gas-chromatography, the not good peak type such as swarming, tailing peak can be produced.This mainly by
In dehydration and Beckmann rearrangement can occur under the high temperature conditions, and the high temperature meeting of gas chromatographic sample introduction mouth and detector
Cause part salicylaldoxime to react, change into benzonitrile, benzoxazoles and N- phenyl formamides, it is quantitative so as to carry out
Detection.And suitable derivatization reagent is selected, and salicylaldoxime is converted into heat-staple material, it is easy to enter using gas chromatography
Row qualitative and quantitative detection.Cyano group is carried in derivatization product, selects ECD (electron capture detector (ECD)) to be detected, beneficial to target
The detection of thing, effectively reduces detection limit.
The present invention using external standard method to measure the aqueous solution in salicylaldoxime concentration, first, test acetylbenzene formonitrile HCN mark
The relation of the concentration of quasi- solution and the response peak area of acetylbenzene formonitrile HCN, its relation is linear, show that peak area is dense with it
The ratio k of degree；Acetylization reaction is recycled, makes salicylaldoxime derive the acetylbenzene formonitrile HCN of chemical conversion good stability, tested,
By the acetylbenzene formonitrile HCN content for measuring, according to the ratio of the amount of relative material the content of salicylaldoxime is calculated.
Wherein, the equation of salicylaldoxime derivative reaction such as formula (1).Because acetylation reagent is excessively added, salicylide
Oxime compares 1 with acetoxyl group benzonitrile by the amount of material:1 is reacted, and finally measures derivatization product (acetoxyl group benzonitrile)
Concentration be initial salicylaldoxime concentration.Final salicylaldoxime concentration (CSalicylaldoxime) computing formula such as formula (2).
For the checking and the inspection of matrix effect of the method, embodied by recovery of standard addition.To not containing salicylaldoxime
Water sample adds respective concentration salicylaldoxime standard liquid, determines and target substance concentration is extracted in organic phase, substitutes into formula (3) and calculates
The rate of recovery.
CSalicylaldoxime=k × peak area (2)
Wherein, R% represents recovery of standard addition；CfRepresent measured salicylaldoxime concentration, VfFor upper organic phase volume；C0
Represent spiked levels in initial water sample, V0For water phase volume.
The invention has the beneficial effects as follows：
1st, the present invention realizes carrying out the derivatization of salicylaldoxime with a step is extracted, and saves time, efficiently, easy to operate.
2nd, the present invention adjusts the Acidity of Aikalinity of solution using carbonate or bicarbonate, controls alkaline environment；On the other hand, may be used
With acetylation reagent reaction, the CO of generation2Gas contributes to the rapid realization of solution extraction process.
3rd, the determination method of the salicylaldoxime that the present invention is provided, the accuracy rate of the method is high, and average relative standard is inclined
Difference is 2.1%-8.4%；The rate of recovery is high, and average recovery rate is 88.7%-92.7%；Detection limit is low, up to 2.13 μ g/L, with behaviour
Work is easy, sensitivity is high, reproducible, quantitative accurately advantage.The method can be environmental wastewater, especially select smelting sewage to carry
For monitoring, it is easy to the control of sewage disposal；Meanwhile, provide supervision and management foundation for corresponding supervision department.
Description of the drawings
Fig. 1 represents impact of the different NaCl concentrations to extraction efficiency；
Fig. 2 represents different Na2CO3The impact of concentration on extraction efficiency.
Specific embodiment
With reference to embodiment, the invention will be further described.
Embodiment 1
Analysis to salicylaldoxime in certain mining area sewage draining exit waste water, analytical procedure includes：
1. 0.01,0.02,0.1,0.5,1 μ g mL are measured respectively using GC-ECD-1Acetylbenzene formonitrile HCN standard liquid,
The ratio k of the response peak area and its concentration that obtain acetylbenzene formonitrile HCN is 0.9993；
2. under room temperature, the waste water containing salicylaldoxime is taken, add 1.25g Na2CO3, 0.12g NaCl are settled to 25mL.
1mL acetic anhydrides (AA), 5mL hexamethylenes is added after about five minutes, to take upper organic phase, in adding 50mL centrifuge tubes, use 8 simultaneously
～10mL deionized waters wash away the acetic anhydride in organic phase, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
It is 0.078 μ g mL to obtain salicylaldoxime concentration in water environment-1。
Embodiment 2
Analysis to salicylaldoxime in Xiang River sewage draining exit waste water, analytical procedure includes：
1. 0.01,0.02,0.1,0.5,1 μ g mL are measured respectively using GC-ECD-1Acetylbenzene formonitrile HCN standard liquid,
The ratio k of the response peak area and its concentration that obtain acetylbenzene formonitrile HCN is 0.9989；
2. under room temperature, the waste water containing salicylaldoxime is taken, add 1g Na2CO3, 0.1g NaCl (m/v) are settled to 20mL.
0.8mL acetic anhydrides (AA), 4mL hexamethylenes is added after about five minutes, to take upper organic phase, in adding 50mL centrifuge tubes, use simultaneously
8～10mL deionized waters wash away the acetic anhydride in organic phase, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
Salicylaldoxime concentration in water environment is obtained, is not detected.
4. wastewater sample is taken again, salicylaldoxime standard liquid is added, and obtains concentration for 1 μ g mL-1Mark-on waste water sample
Product, repeat 2～3 steps, are calculated salicylaldoxime concentration for 0.92 μ g mL-1, therefore the method rate of recovery is up to 92%.
Embodiment 3
Analysis to salicylaldoxime in Dexing copper mine mining area nearby water sample, analytical procedure includes：
1. 0.01,0.02,0.1,0.5,1 μ g mL are measured respectively using GC-ECD-1Acetylbenzene formonitrile HCN standard liquid,
The ratio k of the response peak area and its concentration that obtain acetylbenzene formonitrile HCN is 0.9991；
2. under room temperature, the waste water containing salicylaldoxime is taken, add 1.25g Na2CO3, 0.12g NaCl (m/v) are settled to
25mL.1mL acetic anhydrides (AA), 5mL hexamethylenes is added after about five minutes, to take upper organic phase, add 50mL centrifuge tubes simultaneously
In, the acetic anhydride in organic phase is washed away with 8～10mL deionized waters, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
Salicylaldoxime concentration in water environment is obtained, is not detected.
4. wastewater sample is taken again, salicylaldoxime standard liquid is added, and obtains concentration for 10 μ g mL-1Mark-on waste water sample
Product, repeat 2～3 steps, are calculated salicylaldoxime concentration for 9.15 μ g mL-1, therefore the method rate of recovery is up to 91.5%.
Embodiment 4
The investigation of extractant
1. measure 0.05 respectively using GC-ECD, 0.1,0.5,1, the acetylbenzene formonitrile HCN standard liquid of 2mg/L, obtain second
The response peak area of acyl group benzonitrile is 0.9991 with the ratio k of its concentration；
2. under room temperature, 9 parts of ionized water (three kinds of extractants, each three parallel samples) is removed, added in each sample
1.25g Na2CO3, 0.12g NaCl are the salicylaldoxime Standard Stock solutions of 100mg/L with addition 0.2mL concentration, are settled to
20mL.1mL acetic anhydrides (AA) are added, 5mL hexamethylenes, n-hexane and toluene (three samples of each extractant condition are separately added into
This), after about five minutes, upper organic phase is taken, in adding 50mL centrifuge tubes, washed away in organic phase with 8～10mL deionized waters
Acetic anhydride, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
Salicylaldoxime concentration in water environment is obtained, using formula 3 each specimen extraction efficiency is calculated, and calculated under the conditions of every kind of NaCl concentration
The mean value and relative standard deviation of three parallel samples.
4. can be found by final data analysis, more than 90% recovery can reach using 5mL hexamethylenes or the extraction of 5mL toluene
Efficiency.But the behavior of hexamethylene gas-chromatography is better than toluene.Therefore suitable extraction can be selected in hexamethylene and toluene according to actual conditions
Take agent.
Embodiment 5
The investigation of sodium chloride concentration
1. measure 0.05 respectively using GC-ECD, 0.1,0.5,1, the acetylbenzene formonitrile HCN standard liquid of 2mg/L, obtain second
The response peak area of acyl group benzonitrile is 0.9991 with the ratio k of its concentration；
2. under room temperature, 15 parts of ionized water (five kinds of Variation of Salinity Condition, each three parallel samples) is removed, be separately added into 0,
0.1st, 0.2,0.6,1g NaCl (three samples of each NaCl concentration condition), add the 0.2mL concentration to be in each sample
The salicylaldoxime Standard Stock solutions of 100mg/L, add 1g Na2CO3, it is settled to 20mL.0.8mL acetic anhydrides are added simultaneously
(AA), 4mL hexamethylenes, after about five minutes, take upper organic phase, in adding 50mL centrifuge tubes, are washed away with 8～10mL deionized waters
Acetic anhydride in organic phase, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
Salicylaldoxime concentration in water environment is obtained, using formula (3) each specimen extraction efficiency is calculated, and calculate every kind of NaCl concentration condition
The mean value and relative standard deviation of lower three parallel samples, obtains Fig. 1.
4. can find that NaCl concentration can reach in the range of 0.5%-2% (m/v, g/mL) by final data analysis
More than 90% organic efficiency, most preferable concentrations 0.5% (m/v, g/mL).
Embodiment 6
The investigation of concentration of sodium carbonate
1. measure 0.05 respectively using GC-ECD, 0.1,0.5,1, the acetylbenzene formonitrile HCN standard liquid of 2mg/L, obtain second
The response peak area of acyl group benzonitrile is 0.9991 with the ratio k of its concentration；
2. under room temperature, 18 parts of ionized water (six kinds of concentration conditions, each three parallel samples) is removed, be separately added into 0,
0.04th, 0.2,0.4,1,2g NaCl (each Na2CO3Three samples of concentration conditions), addition 0.2mL concentration is in each sample
The salicylaldoxime Standard Stock solutions of 100mg/L, add 0.1g NaCl, are settled to 20mL.0.8mL acetic anhydrides are added simultaneously
(AA), 4mL hexamethylenes, after about five minutes, take upper organic phase, in adding 50mL centrifuge tubes, are washed away with 8～10mL deionized waters
Acetic anhydride in organic phase, after washing twice, sample introduction.
3. gained derivatization peak areas and acetylbenzene formonitrile HCN curve comparison in step (1), are calculated using external standard method
Salicylaldoxime concentration in water environment is obtained, using formula (3) each specimen extraction efficiency is calculated, and calculate every kind of Na2CO3Concentration bar
The mean value and relative standard deviation of lower three parallel samples of part, obtains Fig. 2.
4. can be found by final data analysis, Na2CO3Concentration can reach 80% in the range of 4%-6% (m/v, g/mL)
Above organic efficiency, most preferable concentrations 5% (m/v, g/mL).
Claims (10)
1. it is a kind of determine water environment in salicylaldoxime content method, it is characterised in that comprise the following steps：
(1) the acetylbenzene formonitrile HCN standard liquid of variable concentrations is prepared, gas chromatographic detection is carried out, acetylbenzene formonitrile HCN is obtained
Response peak area and its concentration ratio k；
(2) take the aqueous solution containing salicylaldoxime, adjust the aqueous solution in alkalescence, add excessive acetylation reagent and can be with
The organic solvent of water stratification carries out acetylization reaction；After the completion of reaction, wash organic phase and remove excessive acetylation reagent；
(3) organic phase after water intaking is washed is placed in sample injection bottle, carries out gas chromatographic detection；According to measuring peak area and ratio k meter
Calculate the concentration of salicylaldoxime in the aqueous solution.
2. the method for claim 1, it is characterised in that in step (2), adjusts water-soluble using sodium carbonate or sodium acid carbonate
The pH of liquid is in alkalescence.
3. method as claimed in claim 2, it is characterised in that the concentration of sodium carbonate or sodium acid carbonate is 4%- in the aqueous solution
6%g/mL。
4. the method as described in any one of claim 1-3, it is characterised in that in step (2), before adding acetylation reagent,
Inorganic salts are added in aqueous.
5. method as claimed in claim 4, it is characterised in that the inorganic salts are sodium chloride, and sodium chloride is dense in the aqueous solution
Spend for 0.5%-2% g/mL.
6. the method for claim 1, it is characterised in that in step (2), acetylation reagent is acetic anhydride.
7. the method for claim 1, it is characterised in that in step (2), the proportion of the organic solvent is lighter than water.
8. method as claimed in claim 7, it is characterised in that the organic solvent is cyclic hydrocar-bons organic solvent.
9. the method for claim 1, it is characterised in that in step (2), in the aqueous solution per 25mL 0.8-2mL is added
Acetic anhydride and 4-5 mL organic solvents, organic solvent is toluene or hexamethylene.
10. the method for claim 1, it is characterised in that the condition of gas chromatographic detection is：Chromatographic apparatus is
Agilent 7890A gas-chromatographies, chromatographic column is HP-5MS；Heating schedule be 80 DEG C of initial temperature, keep 5 min, then with 10 DEG C/
Min speed is raised to 120 DEG C, keeps 1 min, is finally raised to 180 DEG C with 5 DEG C/min speed, keeps 1 min；Injector temperature
For 200 DEG C；Detector is ECD, 220 DEG C of temperature；Splitless injecting samples, carrier gas is nitrogen, the mL/min of flow velocity 1.0, sample size
1.0 μL。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116217430A (en) * | 2022-12-31 | 2023-06-06 | 江苏艾科维科技股份有限公司 | Separation and purification method of high-concentration anhydrous aldoxime |
| CN116217430B (en) * | 2022-12-31 | 2024-05-31 | 江苏艾科维科技股份有限公司 | Separation and purification method of high-concentration anhydrous aldoxime |
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| CN104089914A (en) * | 2014-07-07 | 2014-10-08 | 中蓝连海设计研究院 | Method for quickly measuring concentration of hydroximic acid used as mineral separation collecting agent |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116217430A (en) * | 2022-12-31 | 2023-06-06 | 江苏艾科维科技股份有限公司 | Separation and purification method of high-concentration anhydrous aldoxime |
| CN116217430B (en) * | 2022-12-31 | 2024-05-31 | 江苏艾科维科技股份有限公司 | Separation and purification method of high-concentration anhydrous aldoxime |
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