CN107739337A - A kind of cadmium, aluminium, the preparation method of lead ion chelating agent - Google Patents
A kind of cadmium, aluminium, the preparation method of lead ion chelating agent Download PDFInfo
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Abstract
The invention discloses a kind of preparation method of metal ion chelation agent, belong to analytical chemistry and environmental area.A kind of application more particularly to metal ion chelation agent preparation method and its in processing heavy metal ions in sewage.The preparation method of the chelating agent is：2 hydroxylated chalcones are obtained by o-hydroxyacetophenone and benzaldehyde reaction, the phenyl 1H pyrazolines of 4,5 dihydro 3 (2 hydroxy phenyl) of target product 5 are then made by the chalcone and hydration hydrazine reaction.The novel chelating agents cannot be only used for the complexing and detection of cadmium, aluminium, lead ion, and the analysis method based on the chelating agent is convenient, fast, sensitivity is good, moreover it can be used to deviates from cadmium in contaminant water, aluminium, lead ion, has a good application prospect.
Description
Technical field
The invention belongs to analytical chemistry and Environmental Chemistry field, and in particular to a kind of chelating agent, more particularly to a kind of cadmium,
Lead, the preparation method of chelate aluminum ion mixture and its application in terms of aluminium ion, the detection of heavy metal ion and in environment water process.
Background technology
Metal ion is widely existed in nature, and it is the important composition portion for the osmotic equilibrium for maintaining heterogeneous system
Point, and the necessary component of extensive enzyme reaction.But not all metal ion organism is required to, such as：
Cadmium ion, lead ion；In addition, some metal ions are required for organism but are not the The more the better of intake,
Such as：Aluminium ion.Cadmium is a kind of environmental contaminants and non-human required element, Excess free enthalpy can cause human body to be poisoned.World health
Cadmium is classified as the food contaminant of primary study by tissue；International cancer research institution（IARC）Cadmium is classified as human carcinogen, meeting
Serious harm is caused to human health；U.S.'s poisonous substance and disease registration administration（ATSDR）Cadmium is classified as into the 7th to be detrimental to health
Material；China is also that cadmium is classified as to one of key monitoring index for implementing prediction emission.The toxicity of compound of cadmium is bigger,
After environment is by cadmium pollution, it can be enriched with vivo, cause poisoning, the enrichment of cadmium into human body by food chain
Significantly, even stopped contact, the cadmium of most of accumulation in vivo is remained on and can stayed in the body, the acute poisoning symptom of cadmium
Show as：Nausea,vomiting,diarrhea, salivation then cause nervous centralis poisoning symptom, and severe patient can cause death；Long-term intake
Food containing cadmium, slow poisoning can be caused, be damaged renal tubule and glomerulus, also result in albuminuria, acidaminuria and sugar
Urine.In March, 2013,《South Daily》Report the exceeded rice of Hunan cadmium and enter the message of Guangdong Market, and make us staring
It is tongue-tied.Lead is widely applied to all trades and professions, and the pollution to environment is also increasingly heavier, and the health hazard to human body is also more and more tighter
Weight, at present, lead mainly affect health by way of air, drinking water and food.Lead and its compound enter people
Multiple organs such as the nerve of people, hematopoiesis, digestion, kidney will be damaged after body.After it enters human body, small part meeting is had
Discharge in human body, remaining major part can deposit in vivo.For adult, the invasion of lead can cause dizzy, weak, dizziness,
Sleepy, insomnia, anaemia, immunity degradation etc., there are metallic taste, artery sclerosis, digestive tract ulcer and scorching fundus hemorrhage in some mouths
Etc. symptom；For children, under same environmental condition, intake can be than several times of eminence of being grown up, and harm is extremely serious, can go out
Symptom, the severe patient such as existing hypoevolutism, poor appetite, inconvenient walking, insomnia, feeblemindedness, absent minded will cause
Brain tissue impairment, cause life-long disabilities；For pregnant woman, lead enters can be influenceed development of fetus, is caused abnormal by placenta obstacle in vivo
Shape, miscarriage or stillborn foetus etc..Aluminium, it is that metal element content is most abundant in the earth's crust, the 8% of about total mineralogical composition.The mankind
Development it is inseparable with aluminium.In contemporary society, aluminium has been widely used as construction material, electrical conduction, cooker and food
The many-side such as packaging, this, which is derived from it, has low-density, good electrical and thermal conductivity.In addition, the chemistry according to aluminium compound
Property, it is widely used in the purifying of water and clinical medicine.Pass through the accumulation of solid refuse and the discharge of chemical wastewater
The environmental pollution Deng caused by, it is important that acid rain is caused by air pollution, adds aluminium from Al2O3To Al3+Transformation, be changed into
Al3+Afterwards, taken in and deposited in vivo by people.Although aluminium is also a kind of indispensable element in human body, its amount
If intake is excessive, the bone, kidney and liver of people will especially be caused damage to brain and nervous system, such as op parkinson's
Syndrome and Alzheimer's disease.In addition, other biological can also be damaged, as plant growth course in, Al3+'s
Concentration abnormality, it can significantly suppress the growth of plant.Therefore, go to detect aluminium, lead, cadmium ion using a kind of chelating agent, especially
It is tracking they to be acted in life entity be a thing highly significant.
The method of the heavy metal ion including detection cadmium, lead ion has atomic absorption spectrography (AAS), atomic emission spectrum at present
Method, inductively coupled plasma mass spectrometry etc.；Aluminum ions method is detected, there is graphite furnace atomic absorption spectrometry, electric heating in recent years
Atomic absorption spectrum and inductively coupled plasma atomic emission spectrum etc..Generally, these methods are more or less has
Some defects, as sample instrument is expensive, detection time is long, is unable to real-time on-site detection, complex operation and for micro
The detection of ion is less sensitive etc., and certain limitation is received in the application of reality.The chelating agent developed at present is general only
Can be with a kind of metallic ion coordination（Referenced patents：The synthesis side of Zibo Jin Ding Electro-optical Technology, INC. (US) 62 Martin Road, Concord, Massachusetts 017 heavy metal chelants
Method:China, 104495998.2015-04-08；A kind of chelating agents of Zhejiang University and its application:China, 101735264.2010-
06-16；A kind of heavy metal chelants of Yangzhou Haicheng Bioisystech Co., Ltd:China, 105664417.2016-06-15).
Synthesis step is more in the synthetic method of heavy metal chelant, and the chelating agent being synthesized does not relate to just in heavy metal
And to the metal ion beyond heavy metal；And for a kind of chelating agent and its application and a kind of this two inventions of heavy metal chelant
In, the former has chelation to all metal ions, and the latter just simply has chelation to a kind of heavy metal ion, this
The application of sample in many aspects is just not intended to that effect reached.Therefore, it is contemplated that develop a kind of testing cost it is low,
Detection time is short, easy to operate, can remove several metal ion chelation agents of more than one in contaminant water, i.e. cadmium, aluminium, lead metal
The chelating agent of ion, and it is applied to the fields such as medical science, industry, food.
The content of the invention
It is an object of the invention to provide a kind of system that can chelate cadmium, lead heavy metal ion and aluminum ions chelating agent simultaneously
Preparation Method.The chelating agent has good selectivity and sensitivity in without water-ethanol to aluminium, lead, cadmium ion, especially to aluminium from
Son, add after each metal ion species and do not cause spectrum significantly to change.The present invention is realized to two heavy metal species ion cadmiums
With lead and the aluminum ions high selectivity of trace detection, and before having wide application in fields such as medical science, food, industry
Scape.
To realize goal of the invention, experimental program is specific as follows：Synthesized by research and probe a kind of to cadmium, lead, aluminium ion tool
There is the chelating agent that specific identification acts on, and use it for cadmium, lead, aluminum ions processing.The chelating agent is 4,5- dihydros -3-（2-
Hydroxy phenyl）- 5- phenyl -1H- pyrazoles, its chemical structural formula are as follows：
The synthetic method of the compound：
The synthesis of 2- hydroxylated chalcones：By benzaldehyde（6.8g, 0.05mol）And o-hydroxyacetophenone（5.4g, 0.051mol）One
Rise to be blended in 65mL absolute ethyl alcohol and be stirred, then 13g potassium hydroxide is added in the mixture of stirring, this reaction
Heating water bath 5 hours first at 35 DEG C, then temperature be increased to 70 DEG C of heating water baths and flow back 1-2 hours.After the completion of reaction,
Adjusted as adding dense HCl pH of mixture by obtained by 5-6, and use ethyl acetate（350mL）Extraction, then to extracting
Anhydrous magnesium sulfate is added in organic layer.Then evaporation organic layer, by residue dry-packing to silicagel column, the post oil
Ether：Ethyl acetate=3：1 elution.By evaporating organic solvent, dried at 35 DEG C, obtained yellow particle shape solid
（0.74g）IR (KBr) υmax (cm-1): 3400 (b, OH), 3058.89, 2925.88, 1658.67 (C=O),
1602.74, 1564.16, 1488.94 (C=C), 1217.00 (C-O). 1H-NMR (400 MHz, DMSO-d6): δH
(ppm): 11.50 (1H, s, C2’-OH), 8.25 (d, 1H, H-6, J = 7.32 Hz), 8.06 (d, 1H, H-
β, vinylic, J = 15.60 Hz), 7.95 (d, 2H, H-2’, H-6’, J = 8.72 Hz), 7.82 (d,
1H, H-α, vinylic, J = 16.00 Hz), 7.56 (m, 3H, H-3, H-4, H-5), 7.00 (d, 2H, H-
3’, H-5’, J = 8.28 Hz). 13C-NMR (75MHz, DMSO-d6): δC (ppm): 193.50, 161.90,
143.28, 136.45, 135.49, 133.43, 130.96, 130.87, 129.03, 122.51, 120.71,
119.20, 117.75. QTOF-MSES+: [M +]+(in ESI†) = 225.25 (100%); Analysis
calculated for C15H12O2: C, 80.20%; H, 6.68%; Found: C, 80.16%; H, 6.70%。
The synthesis of chelating agent：By 2- hydroxylated chalcones and hydrazine hydrate（2g）It is mixed in 50mL dimethylformamide（DMF）
In, and add sodium hydroxide (5.6g) and heating stirring is carried out at 78 DEG C 5 hours.After the completion of reaction, by adding dense HCl by institute
The pH for obtaining mixture is adjusted to 7, and uses water（350mL）Extraction, ethyl acetate is then added into organic layer and is dissolved, and
Anhydrous magnesium sulfate is added in this organic layer.Similarly, organic layer is evaporated, by residue dry-packing to silicagel column, the post is used
Petroleum ether：Ethyl acetate=4.5：1 elution is purified.By evaporating organic solvent, obtain dark-brown powdered solid
Body（0.13g）.
The data IR (KBr) of productn max(cm-1)3580, 3410 (b,OH), 3376, 3318,(C=N) 2180,
2240, 2838, 2256(C=N), 1673, 1576, 1511, 1489(C=C), 1369, 1315, 1259(C-O),
1225, 1174, 1116, 1077, 1035, 1009, 853, 839, 810, 789, 748, 726(C-H) .1HNMR
δ: 8.01 (s, 2H), 7.57–7.31 (m, 6H), 5.88 (s, 2H), 3.88 (ddd, J = 13.9, 9.4,
6.1 Hz, 2H), 2.87–2.70 (m, 1H), 1.67–1.43 (m, 2H), 1.30 (dt, J = 14.7, 7.3
Hz, 3H), 0.87 (t, J = 7.3 Hz, 3H); 3C NMR (75 MHz, CDCl3): δ 118.1, 120.3,
121.7, 123.9, 124.8, 125.6, 127.9, 129.1, 129.3, 130.2, 131.2, 131.8, 136.6,
157.2, 154.6, 178.5. MS (ESI): m/z 239.00 [M++Na]+. Analysis calculated for
C15H14N2O(239.42):C, 77.80%; H, 5.00%; N, 12.37%. Found: C, 77.81%; H , 5.07%;
N, 12.35%.
。
。
Specific description of the invention：
By this chelating agent using absolute ethyl alcohol as solvent solution-forming, UV/vis is recorded on Agilent 8453UV/vis spectrometers
Spectrum, scanning range 250-450nm；Fluorescence spectral measuring is carried out on Hitachi F-7000 sepectrophotofluorometers, is swashed
Hair wavelength is 380nm.The test of Absorption and fluorescence spectrum, respectively with 1cm cuvettes, 3mL this chelating agent is pipetted every time
Ethanol solution in cuvette, be separately added into Zn of the same volume with concentration with pipettor2+、Mg2+、Cr3+、Fe3+、Mn2+、
K+、Ni2+、Sr2+、Al3+、Ag+、Hg2+、pb2+、Cu2+、Cd2+Deng the salting liquid of metal ion, with uv-visible absorption spectra and
Fluorescence spectrum studies the spectral quality of this chelating agent and different metal ions interaction, so as to illustrate this chelating agent to three kinds from
The selectivity of son.
In the epoch that industry is increasingly flourishing, environmental pollution also result in the concern of people, and the health of the mankind and ring
Border is closely bound up.The pollution of heavy metal at present not only to people, also damages to other biologies, so as to have influence on whole life
Thing circle.This chelating agent can remove them with three kinds of cadmium, aluminium, lead ions bindings from sewage.This chelating agent is dissolved
Pipette 10mL this solution every time with pipettor in 250mL absolute ethyl alcohols, then to addition same volume in each reagent bottle with dense
The Zn of degree2+、Mg2+、Cr3+、Fe3+、Mn2+、K+、Ni2+、Sr2+、Al3+、Ag+、Hg2+、pb2+、Cu2+、Cd2+Salt Deng metal ion is molten
Liquid, it is irradiated under Agilent 8453UV/vis spectrometers（See accompanying drawing 3 in detail）.The sewage of industry is taken to survey it again
Examination, takes 50mL sewage in separatory funnel, adds the chelating agent that 10mL is dissolved in ethyl acetate, mixes, after standing, finally
Reach separation, remove cadmium, aluminium, the effect of lead ion, in triplicate after, take remaining sewage solution to be observed in reagent bottle
（Accompanying drawing 4）.
Advantages of the present invention：1.4,5- dihydro -3-（2- hydroxy phenyls）- 5- phenyl -1H- pyrazoles is that this chelating agent can be same
When with three kinds of cadmium, aluminium, lead ion chelatings, the time is saved in water treatment procedure, it is fast, the effect of water process can be improved
Rate；2. this chelating agent has obvious fluorescence phenomenon after being combined with cadmium, aluminium, lead ion, high sensitivity, be advantageous in water process
Separation；3. the synthesis step of this chelating agent is easy, itself is solid powder, is easy to store, and cost is low, popularizing application prospect
It is good.
Brief description of the drawings
Fig. 1 is this chelating agent and the uv absorption spectra of different metal ions.
Fig. 2 is the fluorescence spectra of this chelating agent and different metal ions.
Fig. 3 be under uviol lamp chelating agent to the UV absorption figure of different metal ions.
It is ultraviolet under the irradiation of Agilent 8453UV/vis spectrometers that Fig. 4 is that sewage before and after the processing is blended in chelating agent
Figure.
Fig. 5 is the mass spectrum of chelating agent.
Embodiment
Fig. 1 is chelating agent and the uv absorption spectra of different metal ions.In order to probe into chelating agent to aluminium, lead, cadmium from
The selectivity of son, respectively with 1cm cuvettes, pipettes the 3mL ethanol solution of chelating agent in cuvette, is distinguished with dropper every time
Add 0.05mL, 1 × 10-2Mol/L metal ions（Zn2+、Mg2+、Cr3+、Fe3+、Mn2+、K+、Ni2+、Sr2+、Al3+、Ag+、Hg2 +、pb2+、Cu2+、Cd2+）Salting liquid, observe its UV-vis change, its ultraviolet spectrogram in addition to aluminium, lead, cadmium ion,
In the presence of other metal ions, the UV absorption of chelating agent is gone up substantially to be changed without for what.Thus have to this several ion good
Good selectivity.
Fig. 2 is the fluorescence spectra of chelating agent and different metal ions.In order to probe into chelating agent to cadmium, aluminium, lead ion
Sensitivity, respectively with 1cm cuvettes, the 3mL ethanol solution of chelating agent is pipetted every time in cuvette, is separately added into dropper
0.05mL、1×10-2Mol/L metal ions（Zn2+、Mg2+、Cr3+、Fe3+、Mn2+、K+、Ni2+、Sr2+、Al3+、Ag+、Hg2+、pb2+、
Cu2+、Cd2+）Salting liquid, the change of fluorescence pattern is observed, in its fluorescence spectra, it is evident that it can be seen that to aluminium, lead,
Cadmium ion has stronger fluorescence intensity, and other metal ions do not have very strong fluorescence intensity.Thus chelating agent pair
Lead, aluminium, the remolding sensitivity of cadmium ion chelating are preferable.
Fig. 3 be under uviol lamp chelating agent to the UV absorption figure of different metal ions.In Agilent 8453UV/vis
Under the irradiation of spectrometer, containing aluminium, lead, cadmium ion reagent bottle in, there is obvious fluorescence phenomenon, and added with other ions
Phenomenon in reagent bottle has such phenomenon can be so as to being the same without the phenomenon in the reagent bottle for adding metal ion
In the resolution chelate in water process and non-chelated thing, while it also illustrate that the sensitivity of this chelating agent.
Fig. 4 be after sewage before and after the processing mixes with chelating agent under the irradiation of Agilent 8453UV/vis spectrometers
Ultraviolet figure.50mL sewage is taken in separatory funnel, the chelating agent (0.05g) that addition 10mL is dissolved in 250mL ethyl acetate is mixed
Close, take mixed liquor 10mL now to be observed in reagent bottle under uviol lamp, after mixed liquor is stood, finally reach separation,
Remove cadmium, aluminium, the effect of lead ion, in triplicate after, take remaining sewage solution 10mL to be carried out in reagent bottle under uviol lamp
Observation.After both are contrasted, the sewage after discovery processing does not almost have fluorescence phenomenon.Reach by a kind of chelating agent
Remove two heavy metal species ions and excessive aluminum ions effect that will be harmful.
Claims (5)
1. a kind of cadmium, lead, chelate aluminum ion mixture, it is characterised in that：This chelating agent is made by 2- hydroxylated chalcones and hydrazine hydrate, i.e.,
For 4,5- dihydros -3-（2- hydroxy phenyls）- 5- phenyl -1H- pyrazolines, its structure are as follows：
。
2. a kind of cadmium, lead, the preparation method of chelate aluminum ion mixture, it is characterised in that：
1）Absolute ethyl alcohol makees solvent, and benzaldehyde and o-hydroxyacetophenone are mixed together in reaction bulb, temperature control in 35 DEG C,
After stirring 5 hours, temperature rises to 75 DEG C of backflow a few hours；
2）After the completion of reaction, PH, extraction, water removal and evaporation solvent is adjusted, obtains pale yellow powder shape solid；
3）Obtained product is purified by column chromatography；
4）In the case where sodium hydroxide is as catalyst, 2- hydroxylated chalcones and hydrazine hydrate are mixed, a few hours is stirred at 70 DEG C, enters
Row 2）In step, obtained crude product；
5）By crude product in the case where petrol ether/ethyl acetate is solvent, purified to obtain brown powder solid i.e.
For cadmium, lead, aluminum ions chelating agent.
3. a kind of cadmium according to claim 2, lead, the preparation method of chelate aluminum ion mixture, it is characterised in that：In step 3
The ratio for carrying out column chromatography purifying solvent petrol ether/ethyl acetate used is 3:1.
4. a kind of cadmium according to claim 2, lead, the preparation method of chelate aluminum ion mixture, it is characterised in that：In step 5
The ratio for carrying out column chromatography purifying solvent petrol ether/ethyl acetate used is 4.5:1.
5. a kind of cadmium according to claim 2, lead, the preparation method of chelate aluminum ion mixture, it is characterised in that：In step 4
The mol ratio of 2- hydroxylated chalcones and hydrazine hydrate is 1:1.
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| CN111533741A (en) * | 2020-05-21 | 2020-08-14 | 江南大学 | Macrocyclic compound with hydrophobic inner cavity and preparation method thereof |
| CN111792990A (en) * | 2019-04-09 | 2020-10-20 | 中国科学院上海药物研究所 | Unsaturated ketone compound, preparation method and application thereof |
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| WO2020046382A1 (en) | 2018-08-31 | 2020-03-05 | Northwestern University | Substituted heterocycles as c-myc targeting agents |
| CN114174265A (en) * | 2018-08-31 | 2022-03-11 | 西北大学 | Substituted heterocycles as c-MYC targeting agents |
| EP3844152A4 (en) * | 2018-08-31 | 2022-10-26 | Northwestern University | Substituted heterocycles as c-myc targeting agents |
| CN111792990A (en) * | 2019-04-09 | 2020-10-20 | 中国科学院上海药物研究所 | Unsaturated ketone compound, preparation method and application thereof |
| CN111533741A (en) * | 2020-05-21 | 2020-08-14 | 江南大学 | Macrocyclic compound with hydrophobic inner cavity and preparation method thereof |
| CN111533741B (en) * | 2020-05-21 | 2021-04-30 | 江南大学 | Macrocyclic compound with hydrophobic inner cavity and preparation method thereof |
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