CN101270121A - Rhodamine 6G hydrazide salicylaldehyde azomethine, synthesizing process and application in measuring content of copper ion - Google Patents
Rhodamine 6G hydrazide salicylaldehyde azomethine, synthesizing process and application in measuring content of copper ion Download PDFInfo
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Abstract
The present invention relates to rhodamine 6G hydrazide salicylal azomethine, a synthesization method and an application in the content determination of cupric ions, which belong to the field of the analysis and determination of cupric ions in water sample. The molecular structural formula of the rhodamine 6G hydrazide salicylal azomethine is shown on the right, and the present invention discloses the synthesization method of the rhodamine 6G hydrazide salicylal azomethine and rhodamine 6G hydrazide salicylal azomethine solution used for the content determination of a small amount of cupric ions in water sample: 0 percent to 98.99 percent of ethanol, 99.99 percent to 1 percent of acetic acid / sodium acetate buffer solution with the pH value of 5 to 9, in which the total concentration of acetic acid is 1 to 100 millimoles per litre, 0.01 percent of N, N-dimethylformamide and 1ppm to 100ppm of rhodamine 6G hydrazide salicylal azomethine, all measured in mass percentage. By a spectrophotometer, the solution can be used for the accurate quantitative determination of 0.005ppm to 0.256ppm of cupric ions in water sample as well as the semiquantitative determination of no less than 0.075ppm of cupric ions in water sample by direct naked-eye observation on the change of colors.
Description
Technical field
The invention belongs to the assay determination field of cupric ion in the water sample, relate to and utilize a specific specificity that the organic dye solution of cupric ion colour developing is made solution and application thereof.
Background technology
Cupric ion is a kind of common heavy metal ion that extensively is present in the environment, and it benefits the works better of keeping body intravital the having in right amount of people, as participates in intravital hemoposieis, enzyme reaction and some redox processeses or the like.But,, then might cause a series of diseases, as Menkes syndromes and Wilson syndromes etc. as cupric ion shortage or excessive if the metabolic balance of intravital cupric ion is destroyed.Thereby the content that detects cupric ion in the various water quality relevant with the human lives is extremely important.China's drinking water standard (GB 5749-85) regulation copper in drinking water ion content must not be higher than 1.0ppm, and Seawater Quality Standards (GB 3097-1997) requires in the first to fourth class seawater that content of copper ion must not be higher than 0.005,0.01,0.05 respectively, 0.05ppm.
The method that is usually used in analyzing cupric ion at present has anodic stripping method, atomic absorption spectrometry, spectrophotometry and fluorescent spectrometry.Wherein ion chromatography, atomic absorption spectrometry instrument complexity, analytical test is consuming time longer; Spectrophotometry and fluorescent spectrometry instrument are easy, analyze rapidly, are more suitable for the analysis of content of copper ion in water sample.
There is following defective in the method for cupric ion (as National Standard Method GB 7474-87, cupral spectrophotometry) in the present known mensuration water sample:
1, need to use highly toxic organic solvent (as tetracol phenixin) to carry out extracting operation
2, complex operation is introduced error easily
3, transition metal ions interference such as iron, cobalt, nickel are bigger, often need to add masking reagent
Summary of the invention
For addressing these problems, the invention provides a kind of solution, its reagent possesses and mixes the back with the water sample that contains cupric ion and become red characteristic by colourless.When this solution is used for the mensuration of water sample cupric ion, only use nontoxic ethanol/water mixture as solvent, (only needing simple the mixing to get final product) simple to operate, very strong to the various ion immunity from interferencies beyond the cupric ion, and, can be used for naked eyes and directly observe red generation come cupric ion in the qualitative test water sample owing to showing redness (human eye is the most responsive to redness) and obvious to the colour developing of trace copper ion.
What the present invention used is spectrophotometry, utilizes the content of a specific specificity to cupric ion in the organic dye assay determination water sample of cupric ion colour developing.In addition, because the solution of indication of the present invention be redness to the colour developing of cupric ion, can realize that naked eyes directly observe semi-quantitative analysis.
The present invention is used for the ethanol/water mixing solutions of this organic dye the mensuration of multiple water sample content of copper ion.When with water sample to be measured and this solution with certain volume than after mixing, can whether become the roughly content that redness qualitatively judges cupric ion in the water sample by liquid by colourless, further can carry out accurate quantitative analysis at 475～550nm by spectrophotometer.
The present invention has synthesized a kind of novel substance: rhodamine 6G hydrazide salicylaldehyde azomethine is characterized in that molecular structural formula is as follows:
Its outward appearance is the colourless lightpink pressed powder that arrives, and is dissolved in N, and dinethylformamide, methylene dichloride are slightly soluble in ethanol, and be water insoluble.Molecular formula C
33H
32N
4O
3, electron spray(ES) soft ionization positive ion mass spectrum signal is a mass-to-charge ratio 533.3, the hydrogen nuclear magnetic resonance spectrum signal in deuterochloroform is (chemical shift, the ppm of unit): 1.30 (6 hydrogen), 1.87 (6 hydrogen), 3.20 (4 hydrogen), 3.45～3.65 (2 hydrogen), 6.31 (2 hydrogen), 6.44 (2 hydrogen), (6.75 1 hydrogen), 6.86 (1 hydrogen), 7.05 (1 hydrogen), (7.12 1 hydrogen), 7.15 (1 hydrogen), 7.52 (2 hydrogen), (8.00 1 hydrogen), 9.12 (1 hydrogen), 10.91 (1 hydrogen).
The synthetic method of rhodamine 6G hydrazide salicylaldehyde azomethine is characterized in that, comprises the steps:
1) rhodamine 6G with 1 equivalent quality is dissolved in the ethanol of 20～60 equivalent qualities, adds the hydrazine hydrate of 0.25～4 equivalent quality, reacts 8～48 hours down at 30～80 degrees centigrade, cools off, and filters out the precipitation of generation;
2) with the above-mentioned resolution of precipitate of 1 equivalent quality in the volume ratio of 15～1000 equivalent qualities is 3: 1～1: 3 ethanol/dichloromethane mixed solvent, the salicylic aldehyde that adds 0.5～4 equivalent quality, reacted 12～96 hours down at 50～75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine.
Use the solution that rhodamine 6G hydrazide salicylaldehyde azomethine carries out micro-investigating copper ion content in the water sample, it is characterized in that, comprise the various components of following quality percentage composition: 0～98.99% ethanol, 99.99 the acetic acid of～1%pH value 5～9/sodium acetate buffer solution, the acetic acid total concn is every liter 1～100 mmole in this buffered soln, 0.01%N, dinethylformamide and 1～100ppm rhodamine 6G hydrazide salicylaldehyde azomethine.
The application of above-mentioned solution, it is characterized in that, water sample to be measured and described solution were mixed in 9: 1 by volume to 1: 9,10～45 times degrees centigrade place 1～60 minute after, by spectrophotometer in 475～550nm scope or naked eyes directly observation the water sample of copper ions is carried out assay determination.
The concrete synthetic method that is used for the novel organic dye rhodamine 6G hydrazide salicylaldehyde azomethine of water sample investigating copper ion content among the present invention: in 15～500 milliliters of ethanol, add 0.24～24 gram rhodamine 6G and 0.25～25 milliliter of hydrazine hydrate successively, reacted 8～48 hours down at 30～80 degrees centigrade, cool off, filter out the precipitation of generation.With 0.043～21.5 gram gained resolution of precipitate in 30～300 ml volumes ratio is 3: 1～1: 3 ethanol/dichloromethane mixed solvent, reacted 12～96 hours down at 50～75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, dry, obtain rhodamine 6G hydrazide salicylaldehyde azomethine, productive rate 52～91%.
The invention provides a kind of solution that is used for the micro-investigating copper ion content of water sample, this solution is formulated by above-mentioned rhodamine 6G hydrazide salicylaldehyde azomethine, it is characterized in that, comprise the various components of following quality percentage composition: 0～98.99% ethanol, 99.99 the acetic acid of～1%pH value 5～9/sodium acetate buffer solution (the acetic acid total concn is every liter 1～100 mmole in this solution), 0.01%N, dinethylformamide and 1～100ppm rhodamine 6G hydrazide salicylaldehyde azomethine.
The application of above-mentioned solution, it is characterized in that, during use water sample to be measured and above-mentioned solution were mixed in 9: 1 by volume to 1: 9,10～45 times degrees centigrade place 1～60 minute after, by spectrophotometer in 475～550nm scope or naked eyes directly observation the water sample of copper ions is carried out assay determination.This solution is at least the linear response range of cupric ion in tap water and river water sample: 0.005～0.256ppm.Detectability 0.0007ppm.Most of transition metal ions, inorganic salts are all noiseless during in analyte at least 10 times of concentration.Trace copper ionic best effort environment is in the mensuration water sample: rhodamine 6G hydrazide salicylaldehyde azomethine 5ppm, 95% massfraction ethanol, the acetic acid of 5% massfraction pH=7/sodium acetate buffer solution (the acetic acid total concn is 0.01 mole every liter), solution and testing sample mixed volume were than 1: 1, room temperature (30 degrees centigrade) was placed 3～5 minutes down, and spectrophotometer detects wavelength 530nm.
The advantage and the positively effect of invention:
1, solution provided by the invention can be by there being the colourless cupric ion that becomes in red colour developing pattern (enhancing of 475～550nm absorbancy) the quantitative assay water sample, and sensitivity is very high, detectability 0.7ppb, and linearity range is wide, is at least 0.005～0.256ppm.
2, solution provided by the invention is with low cost, makes simply, does not contain the toxicity organic solvent.
When 3, solution provided by the invention cupric ion in water sample is measured, be not subjected to the interference (noiseless when interferent concentration decuples copper ion concentration at least) of most of transition metal ions and inorganic salts.
When 4, solution provided by the invention is used for water sample cupric ion mensuration, but naked eyes are directly observed qualitative test.
Description of drawings
Fig. 1 the invention process example seven solution are used to test the absorption spectrum variation synoptic diagram of 0～0.64ppm cupric ion water sample.
Embodiment
Rhodamine 6G hydrazide salicylaldehyde azomethine among the present invention is a kind of novel substance, schematic arrangement as shown in Figure 1, its chemical synthesis process is as follows:
1) rhodamine 6G with 1 equivalent quality is dissolved in the ethanol of 20～60 equivalent qualities, adds the hydrazine hydrate of 0.25～4 equivalent quality, reacts 8～48 hours down at 30～80 degrees centigrade, cools off, and filters out the precipitation of generation;
2) with the above-mentioned resolution of precipitate of 1 equivalent quality in the volume ratio of 15～1000 equivalent qualities is 3: 1～1: 3 ethanol/dichloromethane mixed solvent, the salicylic aldehyde that adds 0.5～4 equivalent quality, reacted 12～96 hours down at 50～75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine.
The composition of the solution of indication of the present invention:
0～98.99% ethanol, the acetic acid of 99.99～1%pH value 5～9/sodium acetate buffer solution (the acetic acid total concn is every liter 1～100 mmole in this solution), 0.01%N, dinethylformamide and 1～100ppm rhodamine 6G hydrazide salicylaldehyde azomethine.
Utilize the trace copper ion in this measured in solution water sample:
Water sample to be measured was mixed with above-mentioned solution behind the membrane filtration after filtration in 9: 1 by volume to 1: 9, behind hand vibration mixing, placed 1～60 minute down in 10～45 degrees centigrade.Afterwards liquid is transferred in the cuvette, under 475～550nm, measures by spectrophotometer.Determine at first that by the series of standards sample copper ion concentration is to the absorbancy working curve, again water samples such as tap water, river are carried out analytical test, prove that at last method of the present invention can realize quantitative analysis to the cupric ion in 0.005～0.256ppm scope in the water sample at least.Interference simultaneously, selectivity test show, most of salts, as sodium, potassium, magnesium, calcium salt, with transition metal ion iron, cobalt, nickel, zinc, cadmium, mercury, lead and vitriol, hydrochloride, nitrate, phosphoric acid salt etc., at least up to 10 times under the concentration of cupric ion to method of the present invention all noiseless (error is less than 5%).
Embodiment:
Embodiment one to three is the chemosynthesis of rhodamine 6G hydrazide salicylaldehyde azomethine.
Embodiment one
In 15 milliliters of ethanol, add 0.24 gram rhodamine 6G and 0.96 gram hydrazine hydrate successively, reacted 8 hours down, cool off, filter out the precipitation of generation at 30 degrees centigrade.With 0.043 gram gained resolution of precipitate in 30 ml volumes ratio is 3: 1 ethanol/dichloromethane mixed solvent, add 0.172 gram salicylic aldehyde, reacted 12 hours down at 50 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine, productive rate 52%.
Embodiment two
In 500 milliliters of ethanol, add 24 gram rhodamine 6Gs and 24 gram hydrazine hydrates successively, reacted 48 hours down, cool off, filter out the precipitation of generation at 80 degrees centigrade.With 21.5 gram gained resolution of precipitates in 300 ml volumes ratio is 1: 3 ethanol/dichloromethane mixed solvent, add 21.5 gram salicylic aldehydes, reacted 96 hours down at 75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine, productive rate 91%.
Embodiment three
In 50 milliliters of ethanol, add 2.4 gram rhodamine 6Gs and 0.6 gram hydrazine hydrate successively, reacted 24 hours down, cool off, filter out the precipitation of generation at 60 degrees centigrade.With 2.15 gram gained resolution of precipitates in 30 ml volumes ratio is 1: 1 ethanol/dichloromethane mixed solvent, add 1.08 gram salicylic aldehydes, reacted 24 hours down at 75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine, productive rate 78%.
Embodiment four to ten is used for the mensuration of water sample content of copper ion for solution of the present invention.
Prepared following several solns, number consecutively is A, B, C, D, E, F, G, H, I.
A：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 5 gram pH=5,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
B：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 5 gram pH=7,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
C：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 5 gram pH=9,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
D：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 1 mmole in this solution) of 5 gram pH=7,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
E：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 100 mmole in this solution) of 5 gram pH=7,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
F：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 5 gram pH=7,0.05 gram N, dinethylformamide, 50 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
G：
495 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 5 gram pH=7,0.05 gram N, dinethylformamide, 0.5 milligram of rhodamine 6G hydrazide salicylaldehyde azomethine
H：
0 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 500 gram pH=7,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
I：
250 gram ethanol, acetic acid/sodium acetate buffer solution (the acetic acid total concn is every liter 10 mmole in this solution) of 250 gram pH=7,0.05 gram N, dinethylformamide, 5 milligrams of rhodamine 6G hydrazide salicylaldehyde azomethines
Embodiment four
With solution A, B, C, D, E, F, G Tsing-Hua University's drinking public water supply, distilled water, deionized water are analyzed, mixed in 1: 9,1: 1,9: 1 according to solution A～G and analyzed sample, in 475,530, absorbancy can not detect in the 550nm place increases, do not record and contain cupric ion (being lower than detectability).Use aas determination also really not detect copper, prove that this group solution does not produce 475～550nm absorbancy increase signal to the water sample of copper ions not.In addition, in tap water, add 16.0 respectively, behind the cupric ion standard substance (analytical pure Salzburg vitriol) of 64.0ppb, mixed in 1: 9,1: 1,9: 1 according to solution A～G and analyzed sample, use the same method again it is carried out spectrophotometry at the 530nm place, detect cupric ion: 15.1,63.3ppb (A solution mixes at 1: 9), 15.7,64.2ppb (A solution mixes at 1: 1), 16.2,63.1ppb (A solution mixes at 9: 1); 16.3,64.5ppb (B solution mix at 1: 9), 15.2,64.1ppb (B solution mixes at 1: 1), 16.4,63.3ppb (B solution mixes at 9: 1); 16.5,64.7ppb (C solution mix at 1: 9), 15.6,64.2ppb (C solution mixes at 1: 1), 15.6,63.8ppb (C solution mixes at 9: 1); 16.1,64.2ppb (D solution mix at 1: 9), 15.8,64.3ppb (D solution mixes at 1: 1), 15.7,63.8ppb (D solution mixes at 9: 1); 15.4,63.6ppb (E solution mix at 1: 9), 15.5,63.8ppb (E solution mixes at 1: 1), 15.2,63.1ppb (E solution mixes at 9: 1); 16.1,64.2ppb (F solution mix at 1: 9), 16.3,64.5ppb (F solution mixes at 1: 1); 15.3,62.8ppb (G solution mix at 1: 1), 15.5,63.4ppb (G solution mixes at 9: 1); The rate of recovery is all between 94～106%.Prove that method of the present invention is very accurate to trace copper ionic measurement in the tap water.
Embodiment five
With Solution H, I Tsing-Hua University's drinking public water supply is measured, mixed at 1: 1, in 475,530,550nm place can not detect the absorbancy increase, do not record and contain cupric ion (being lower than detectability) according to solution and analyzed sample.Use aas determination also really not detect copper, prove that this group solution does not produce 475～550nm absorbancy increase signal to the water sample of copper ions not.In addition, in tap water, add 16.0 respectively, behind the cupric ion standard substance (analytical pure Salzburg vitriol) of 64.0ppb, mix at 1: 1 according to solution and analyzed sample, use the same method again it is carried out spectrophotometry at the 530nm place, detect cupric ion: 15.1,62.8ppb (Solution H); 15.5,63.2ppb (solution I).The rate of recovery is all between 94～106%, and is respond well.
Embodiment six
With solution B with after the Tsing-Hua University's drinking public water supply that adds the 64.0ppb cupric ion mixes by 1: 1 volume ratio, under 10 degrees centigrade, placed respectively 60,30,15 minutes, under 30 degrees centigrade, placed respectively 30,15,3 minutes, under 45 degrees centigrade, placed respectively 15,3,1 minutes, with spectrophotometer 475,530, the 550nm place measures, obtain the result to be:
The rate of recovery is all between 95～105%, and is respond well.
Embodiment seven
With solution B Tsing-Hua University's drinking public water supply is carried out the standard copper ion and add test, solution and testing sample mixed volume were than 1: 1, room temperature (30 degrees centigrade) was placed 3～5 minutes down, and spectrophotometer detects wavelength 530nm, and the absorption spectrum that obtains variation and typical curve are as shown in Figure 2.Linear good, linearity range is at least 0.005～0.256ppm.10 blank tests record to detect and are limited to 0.7ppb.Add 10 times of interfering substances simultaneously: sodium, potassium, magnesium, calcium salt to copper ion concentration, with transition metal ion iron, cobalt, nickel, zinc, cadmium, mercury, lead and vitriol, hydrochloride, nitrate, phosphoric acid salt etc., the mensuration of cupric ion is all disturbed small (error is less than 5%).
Embodiment eight
With solution B river, Tsing-Hua University school river is analyzed, solution and testing sample mixed volume were than 1: 1, and room temperature (30 degrees centigrade) was placed 3～5 minutes down, and spectrophotometer detects wavelength 530nm, and detecting copper ion concentration is 7.8ppb.Use atomic absorption spectrometry to detect copper content and be 8.1ppb.Proof present method can realize quantitative assay to the cupric ion of trace in the river.In addition, in this river, behind the adding 16.0ppb cupric ion, in kind it is measured with solution B again, detect cupric ion 23.0ppb, the rate of recovery 97%.Prove that method of the present invention to trace copper ionic measurement in the river accurately.
Embodiment nine
With solution B certain copper staining water sample is analyzed (copper ions 0.064ppm, iron 0.50ppm, mercury 0.50ppm, manganese 1.0ppm, zinc 1.0ppm, each 100ppm of sodium K-Mg-Ca, salt acid group and each 200ppm of nitrate radical), solution and testing sample mixed volume were than 1: 1, room temperature (30 degrees centigrade) was placed 3～5 minutes down, spectrophotometer detects wavelength 530nm, and detecting copper ion concentration is 0.068ppm.In addition, in this water sample, behind the adding 0.064ppm cupric ion, in kind it is measured with solution B again, detect cupric ion 0.139ppm, the rate of recovery 105%.
Embodiment ten
The water sample that will contain the 0.30ppm cupric ion with transfer in the vial after solution B is mixed by 1: 1 volume ratio.Behind hand vibration mixing, placed 3～5 minutes down in room temperature (30 degrees centigrade).Can observe solution obviously reddens.And the water sample of copper ions can't not observe any color by same process of the test.In addition,, obtain variable color contrast figure, can carry out the sxemiquantitative test to containing the water sample that is not less than the 0.075ppm cupric ion by the directly more red degree of depth of naked eyes according to this figure by being the series of standards solution of 0～0.60ppm with quadrat method copper test ion content.
Claims (4)
1, rhodamine 6G hydrazide salicylaldehyde azomethine is characterized in that, molecular structural formula is as follows:
2, the synthetic method of rhodamine 6G hydrazide salicylaldehyde azomethine as claimed in claim 1 is characterized in that, comprises the steps:
1) rhodamine 6G with 1 equivalent quality is dissolved in the ethanol of 20～60 equivalent qualities, adds the hydrazine hydrate of 0.25～4 equivalent quality, reacts 8～48 hours down at 30～80 degrees centigrade, cools off, and filters out the precipitation of generation;
2) with the above-mentioned resolution of precipitate of 1 equivalent quality in the volume ratio of 15～1000 equivalent qualities is 3: 1～1: 3 ethanol/dichloromethane mixed solvent, the salicylic aldehyde that adds 0.5～4 equivalent quality, reacted 12～96 hours down at 50～75 degrees centigrade, removal of solvent under reduced pressure, clean solid residue with ethanol, drying obtains rhodamine 6G hydrazide salicylaldehyde azomethine.
3, application rights requires 1 described rhodamine 6G hydrazide salicylaldehyde azomethine to be used for the solution of the micro-investigating copper ion content of water sample, it is characterized in that, comprise the various components of following quality percentage composition: 0～98.99% ethanol, 99.99 the acetic acid of～1%pH value 5～9/sodium acetate buffer solution, the acetic acid total concn is every liter 1～100 mmole in this buffered soln, 0.01%N, dinethylformamide and 1～100ppm rhodamine 6G hydrazide salicylaldehyde azomethine.
4, as the application of solution as described in the claim 3, it is characterized in that, water sample to be measured and described solution were mixed in 9: 1 by volume to 1: 9,10～45 times degrees centigrade place 1～60 minute after, by spectrophotometer in 475～550nm scope or naked eyes directly observation the water sample of copper ions is carried out assay determination.
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