CN106044947B - A kind of ion-exchanger and preparation method thereof based on modified resin - Google Patents
A kind of ion-exchanger and preparation method thereof based on modified resin Download PDFInfo
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- CN106044947B CN106044947B CN201610526192.9A CN201610526192A CN106044947B CN 106044947 B CN106044947 B CN 106044947B CN 201610526192 A CN201610526192 A CN 201610526192A CN 106044947 B CN106044947 B CN 106044947B
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
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Abstract
It is to modify Amberlite XAD-4 resin by 5-sulphosalicylic acid to be made the invention discloses a kind of ion-exchanger based on modified resin.Gained ion-exchanger can be used in adsorbing Co in PTA waste water2+、Mn2+, removal rate is up to 90% or more；It and with after salt acid soak, can desorb, that is, there is good reproducibility.
Description
Technical field
The invention belongs to environmental friendly material fields, and in particular to a kind of ion-exchanger and its preparation based on modified resin
Method.
Background technique
P-phthalic acid (purified terephthalic acid, PTA) as production PET bottle, terylene fiber,
The important source material of polyester film, insecticide, dyestuff etc. is very widely used.When by by the end of April, 2014, Chinese PTA industry
Production capacity has been up to 36,000,000 tons/year.PTA production process includes oxidation and hydrofinishing Unit two.It is used in oxidation unit
Transition metals cobalt, manganese make catalyst, so containing a large amount of soluble aromatic acid by-products and Co in PTA waste water2+、Mn2+Metal from
Son.PTA refined unit needs to use a large amount of deionized waters as solvent, produces 1 ton of PTA for 3-4 tons of generation of waste water, China
PTA produce and generate about 100,000,000 tons of waste water in industrial year.Since PTA device technique water is all disposable, the country in prior art
There are no Sewage treatments to utilize successful precedent in same device, therefore quantity of wastewater effluent is very big in PTA production process.And PTA
Co in refined unit waste water2+、Mn2+The concentration of ion is respectively 13.2 ppm, 19.5 ppm.China is " dirty in publication in 1996
Water comprehensive discharge standard " clear stipulaties in (GB8978-1996): total cobalt, manganese maximal emission are in the second pollutant
2.0 mg/L are lower than 2 ppm.So if about 100,000,000 tons useless can be made by the metal ion treatment of dissolution to certain degree
Water recycling and reusing not only can greatly alleviate the pressure of the water resource use aspects of China, but also can be with Call Provision, manganese weight
Metal resource.It is mainly at present that the processing of cobalt, manganese ion in waste water is returned in the removal of COD to the processing of PTA industrial wastewater
Receipts are seldom related to.
Industrially it can be divided into two major classes, chemical method and physical chemistry using the technology of more processing metal ion at present
Method.Chemical method includes bioanalysis, electrolysis method, oxidation-reduction method and chemical precipitation method.And in physical-chemical process mainly by absorption method,
Ion-exchange, solvent extraction and UF membrane.However, existing processing method all haves the shortcomings that its respectively, such as inconvenient,
At high cost, low efficiency, reusable rate are low.Ion-exchange because its, it is renewable, can continuous dynamic adsorption, large amount of adsorption,
The theory at present for the clean and environmental protection of wastewater treatment and circular economy is agreed with.
Summary of the invention
The object of the present invention is to provide a kind of ion-exchanger based on modified resin, gained ion-exchanger can be moved continuously
State absorption recycles renewable, property and steadily removes cobalt in PTA waste water, manganese Metal ion.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of ion-exchanger based on modified resin is to modify Amberlite XAD-4 resin by 5-sulphosalicylic acid
It is made；The structure of gained ion-exchanger is as follows:
,
WhereinIndicate the basic skeleton structure of Amberlite XAD-4 resin.
Preparation method is as follows:
(1) 3 ~ 5 g Amberlite XAD-4 resins are dissolved in 10 ~ 20 mL octanols, the chlorine of 20 ~ 30 mL is then added
5 ~ 10 g anhydrous acid catalysts are added portionwise in methylating agent under stirring, after reacting 2 ~ 10 h at 40 ~ 90 DEG C, successively with third
After ketone, hydrochloric acid, distilled water cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) after step (1) resulting chloromethylation products sufficiently being impregnated 2 h in 30 mL solvents, 2 ~ 5 g 5- are added
Sulfosalicylic acid, after reacting 24 ~ 72 h at 70 ~ 100 DEG C, after successively being cleaned with acetone, hydrochloric acid, distilled water, at 60 DEG C
Dry 8 h are to get the ion-exchanger based on modified resin.
Chloromethyl agent as described in step (1) is methylene chloride or chloromethyl methyl ether.
Anhydrous acid catalysts as described in step (1) are aluminum trichloride (anhydrous) or anhydrous zinc chloride.
Solvent described in step (2) is dichloroethanes, nitrobenzene or N-N- dimethylformamide.
Gained can be used for adsorbing Co in PTA waste water based on the ion-exchanger of modified resin2+、Mn2+；Preferred adsorption bar
Part are as follows: 25 DEG C of adsorption temp, pH=4,90 ~ 120 min of adsorption time.Then it impregnates to 120 in the hydrochloric acid of 2 mol/L ~
240 min can have the function that parsing.
Remarkable advantage of the invention:
(1) present invention gained ion-exchanger specific surface is big, and large amount of adsorption can be applied to Co in processing PTA waste water2+、Mn2 +；Ion-exchanger material is easily separated, can continuous dynamic adsorption.And easy to operate, green non-pollution, cobalt, manganese in processed waste water
Ion concentration is below 2 ppm, has reached national emission standard.
(2) the 5-sulphosalicylic acid functional agent used in the present invention, in the preparation process for having got rid of conventional ion exchanger resin
Sulfonation process, do not use the concentrated sulfuric acid with strong oxidizing property, oleum, chlorosulfonic acid as sulfonated reagent, solve biography
A large amount of spent acid discharge bring problem of environmental pollutions and production safety problem in technique of uniting.
Detailed description of the invention
Fig. 1 is the infrared of Amberlite XAD-4 and the ion-exchanger 2 based on modified resin in the embodiment of the present invention 2
Map.
Fig. 2 is the influence that time and temperature adsorb heavy metal ion capacity to 2 intermediate ion exchanger 2 of the embodiment of the present invention,
Fig. 2 (a) is cobalt ions, and Fig. 2 (b) is manganese ion.
Fig. 3 is the shadow that different pH value adsorb heavy metal ion capacity to gained ion-exchanger 2 in the embodiment of the present invention 2
It rings.
Fig. 4 is the experiment of 2 intermediate ion exchanger of the embodiment of the present invention, 2 adsorption and desorption regeneration cycle, and Fig. 4 (a) is cobalt ions,
Fig. 4 (b) is manganese ion.
Specific embodiment
Using the content of element in ion-exchanger of the elemental microanalysis method measurement based on modified resin.
Using Fourier transformation infrared spectrometer (Spectrum 2000) to above-mentioned Amberlite XAD-4 and based on changing
Property resin ion-exchanger carry out infrared analysis.
Cobalt, manganese ion are measured using inductively coupled plasma atomic emission spectrometry (ICP-AES) Optima 8000
Concentration.
Embodiment 1
The preparation of ion-exchanger 1 based on modified resin the following steps are included:
(1) 2 g Amberlite XAD-4 resins are dissolved in 10 mL octanols, 30 mL methylene chloride is then added, stir
It mixes down and 5 g anhydrous zinc chlorides is added portionwise, after 10 h are reacted at 40 DEG C；After successively being cleaned with acetone, hydrochloric acid, distilled water,
Dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 2 g step (1) resulting chloromethylation products are sufficiently impregnated into 2 h in 30 mL dichloroethanes (DCE),
Then 2g 5-sulphosalicylic acid is added, 24 h are reacted at 70 DEG C, after difference is successively cleaned with acetone, hydrochloric acid, distilled water, in
Dry 8 h are at 60 DEG C to get ion-exchanger 1；Elemental analysis, theoretical value: C, 57.49；H, 4.19；S, 9.58%；Experiment value:
C, 73.14；H, 5.77；S, 5.27%.
Embodiment 2
The preparation of ion-exchanger 2 based on modified resin the following steps are included:
(1) 5 g Amberlite XAD-4 resins are dissolved in 20 mL octanols, 30 mL chloromethyl methyl ethers are then added,
10 g aluminum trichloride (anhydrous)s are added portionwise under stirring, after 10 h are reacted at 90 DEG C；It is successively clear with acetone, hydrochloric acid, distilled water
After washing, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 1 g step (1) resulting chloromethylation products are placed in 30 mL nitrobenzenes and sufficiently impregnate 2 h, then plus
Enter 3 g 5-sulphosalicylic acids, 72 h is reacted at 100 DEG C, after difference is successively cleaned with acetone, hydrochloric acid, distilled water, in 60
Dry 8 h are at DEG C to get the ion-exchanger 2(Amberlite XAD-4 [5-sulfosalicylic based on modified resin
Acid])；Elemental analysis, theoretical value: C, 57.49；H, 4.19；S, 9.58%；Experiment value: C, 61.13；H, 4.56；S, 8.58%.
Using Fourier transformation infrared spectrometer (Spectrum 2000) to Amberlite XAD-4 and ion-exchanger 2
Infrared analysis is carried out, resulting infrared spectrum is as shown in Fig. 1, infrared right with ion-exchanger 2 by Amberlite XAD-4
Than discovery: compared to Amberlite XAD-4,1663.2 cm-1The absorption peak at place is the stretching vibration peak of carboxylic acid (C=O key),
1346.6 cm-1、1201.6 cm-1、1036.1 cm-1The absorption peak at place is the neighbouring asymmetry of sulfonic group (C-S key) and symmetrical
Stretching vibration peak illustrates that 5-sulphosalicylic acid functional agent is successfully grafted on Amberlite XAD-4 resin, prepares and is based on changing
The ion-exchanger of property resin.
Embodiment 3
The preparation of ion-exchanger 3 based on modified resin the following steps are included:
(1) 4 g Amberlite XAD-4 resins are dissolved in 10 mL octanols, 30 mL methylene chloride is then added, stir
It mixes down and 5 g aluminum trichloride (anhydrous)s is added portionwise, it is successively clear with acetone, hydrochloric acid, distilled water respectively after 10 h are reacted at 40 DEG C
After washing, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 3 g step (1) resulting chloromethylation products are abundant in 30 mL N-N- dimethylformamides (DMF)
2 h are impregnated, 5 g 5-sulphosalicylic acids are then added, 72 h are reacted at 100 DEG C, successively use acetone, hydrochloric acid, distillation respectively
After water cleaning, dry 8 h are at 60 DEG C to get the ion-exchanger 3 based on modified resin；Elemental analysis, theoretical value: C,
57.49；H, 4.19；S, 9.58%；Experiment value: C, 65.99；H, 5.05；S, 7.24%.
Embodiment 4
The preparation of ion-exchanger 4 based on modified resin the following steps are included:
(1) 5 g Amberlite XAD-4 resins are dissolved in 10 mL octanols, 30 mL chloromethyl methyl ethers are then added,
10 g anhydrous zinc chlorides are added portionwise under stirring, after 10 h are reacted at 80 DEG C, successively use acetone, hydrochloric acid, distilled water respectively
After cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 3 g step (1) resulting chloromethylation products are sufficiently impregnated into 2 h in 30 mL dichloroethanes (DCE),
Then 5 g 5-sulphosalicylic acids are added, 48 h are reacted at 100 DEG C, after difference is successively cleaned with acetone, hydrochloric acid, distilled water,
Dry 8 h are at 60 DEG C to get the ion-exchanger 4 based on modified resin；Elemental analysis, theoretical value: C, 57.49；H,
4.19；S, 9.58%；Experiment value: C, 64.08；H, 4.85；S, 7.77%.
Embodiment 5
The preparation of ion-exchanger 5 based on modified resin the following steps are included:
(1) 5 g Amberlite XAD-4 resins are dissolved in 10 mL octanols, 30 mL methylene chloride is then added, stir
It mixes down and 8 g aluminum trichloride (anhydrous)s is added portionwise, 10 h are reacted at 90 DEG C.Products therefrom successively uses acetone, hydrochloric acid, steaming respectively
After distilled water cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) by 2 g step (1) resulting chloromethylation products in equipped with 2 h are sufficiently impregnated in 30 mL nitrobenzenes, so
After 5 g 5-sulphosalicylic acids are added, react 72 h at 100 DEG C, after difference is successively cleaned with acetone, hydrochloric acid, distilled water, in
Dry 8 h are at 60 DEG C to get the ion-exchanger 5 based on modified resin；Elemental analysis, theoretical value: C, 57.49；H, 4.19；
S, 9.58%；Experiment value: C, 62.03；H, 4.65；S, 8.33%.
Embodiment 6
The preparation of ion-exchanger 6 based on modified resin the following steps are included:
(1) 5 g Amberlite XAD-4 resins are dissolved in 20 mL octanols, 30 mL chloromethyl methyl ethers are then added,
10 g anhydrous zinc chlorides are added portionwise under stirring, after 10 h are reacted at 90 DEG C, successively use acetone, hydrochloric acid, distilled water respectively
After cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 3 g step (1) obtained chloromethylation products are filled in 30 mL N-N- dimethylformamides (DMF)
Sub-dip steeps 2 h, and 5 g 5-sulphosalicylic acids are then added, and 36 h are reacted at 70 DEG C, successively use acetone, hydrochloric acid, distillation respectively
After water cleaning, dry 8 h are at 60 DEG C to get the ion-exchanger 6 based on modified resin；Elemental analysis, theoretical value: C,
57.49；H, 4.19；S, 9.58%；Experiment value: C, 65.49；H, 4.50；S, 7.38%.
Embodiment 7
The preparation of ion-exchanger 7 based on modified resin the following steps are included:
(1) 5 g Amberlite XAD-4 resins are dissolved in 10 mL octanols, 30 mL methylene chloride is then added, stir
It mixes down and 8 g aluminum trichloride (anhydrous)s is added portionwise, it is successively clear with acetone, hydrochloric acid, distilled water respectively after 10 h are reacted at 90 DEG C
After washing, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 3 g step (1) obtained chloromethylation products are sufficiently impregnated 2 in 30 mL dichloroethanes (DCE)
Then 5 g 5-sulphosalicylic acids are added in h, 72 h are reacted at 80 DEG C, and difference is successively cleaned with acetone, hydrochloric acid, distilled water
Afterwards, 8 h are dried at 60 DEG C to get the ion-exchanger 7 based on modified resin；Elemental analysis, theoretical value: C, 57.49；H,
4.19；S, 9.58%；Experiment value: C, 62.41；H, 4.69；S, 8.23%.
Embodiment 8
The preparation of ion-exchanger 8 based on modified resin the following steps are included:
(1) by 5 g Amberlite XAD-4 resins be dissolved in 10 mL octanols be added 100 mL three-necked flasks in, then plus
Enter 30 mL chloromethyl methyl ethers, 10 g anhydrous zinc chlorides are added portionwise under stirring, after 10 h are reacted at 90 DEG C, respectively successively
After being cleaned with acetone, hydrochloric acid, distilled water, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 3 g step (1) resulting chloromethylation products are sufficiently impregnated into 2 h in 30 mL nitrobenzenes, then plus
Enter 5 g 5-sulphosalicylic acids, 48 h is reacted at 100 DEG C, after difference is successively cleaned with acetone, hydrochloric acid, distilled water, in 60
Dry 8 h are at DEG C to get the ion-exchanger 8 based on modified resin；Elemental analysis, theoretical value: C, 57.49；H, 4.19；S,
9.58%；Experiment value: C, 61.48；H, 4.59；S, 8.48%.
Embodiment 9
The preparation of ion-exchanger 9 based on modified resin the following steps are included:
(1) by 5 g Amberlite XAD-4 resins be dissolved in 20 mL octanols be added 100 mL three-necked flasks in, then plus
Enter 30 mL methylene chloride, 8 g aluminum trichloride (anhydrous)s are added portionwise under stirring and are successively used respectively after reacting 10 h at 90 DEG C
After acetone, hydrochloric acid, distilled water cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) 2 g step (1) resulting chloromethylation products are abundant in 30 mL N-N- dimethylformamides (DMF)
2 h are impregnated, 5 g 5-sulphosalicylic acids are then added, 72 h are reacted at 100 DEG C, successively use acetone, hydrochloric acid, distillation respectively
After water cleaning, dry 8 h are at 60 DEG C to get the ion-exchanger 9 based on modified resin；Elemental analysis, theoretical value: C,
57.49；H, 4.19；S, 9.58%；Experiment value: C, 61.56；H, 4.61；S, 8.43%.
Ion-exchanger 2 based on modified resin is for adsorbing Co in PTA waste water2+、Mn2+Process conditions screening experiment:
1, time and temperature screening experiment
Taking 200 mL cobalts, manganese Metal ion concentration is 100 ppm titers in 250 mL conical flasks, and 0.3 g is added
Ion-exchanger 2 prepared by the present invention based on modified resin, respectively under the conditions of 20 DEG C, 25 DEG C, 30 DEG C, water bath with thermostatic control
160 rpm of oscillator, separated in time sampling, is surveyed using inductively coupled plasma atomic emission spectrometry (ICP-AES)
Determine cobalt, manganese ion concentration, investigates the influence with temperature to adsorption effect in different times.
From the result of Fig. 2:
(1) adsorbance increases as the temperature rises, illustrates that adsorption process is the endothermic reaction, therefore in certain temperature
Range increases temperature, is conducive to adsorb, but temperature adsorption capacity is influenced it is smaller, for energy conservation, the considerations of economic benefits,
Preferably 25 DEG C of the present invention are optimum temperature.
(2) adsorption rate in 0 ~ 60 min is very fast, and adsorbance reaches 90%, adsorbs after 60 min slowly, may be by interior
It extends influence, in order to make absorption sufficiently achieve balance, subsequent adsorbtion experimental period is set to 120 min.
2, influence of the different pH value to adsorption of metal ions amount
200 mL are taken respectively, concentration is the cobalt of 100 ppm, manganese Metal ion titer in 7 250 mL conical flasks, point
The 0.3 g ion-exchanger 2 prepared by the present invention based on modified resin is not added, adjusting pH is respectively 1,2,3,4,5,6,7, In
It 25 DEG C, under 160 rpm of thermostatic control oscillator vibration, is sampled after 120 min, utilizes inductively coupled plasma atomic emission spectrum
Method (ICP-AES) measures cobalt, manganese ion concentration, the adsorbance under the conditions of calculating respectively.
Shown by Fig. 3: the adsorbance of metal ion increases with pH and is increased, and has maximum value when pH is 4.Its reason may
It is the H when pH is smaller, in one side solution+Competitive Adsorption can occur with cobalt, manganese ion；On the other hand, adsorbent surface holds
Easily protonation generates repulsive interaction to cobalt, manganese ion, is unfavorable for adsorbing.After pH value increases, H+Interference reduce, band itself
The material of negative electrical charge and positively charged metal ion are easier to that ion exchange occurs, so that adsorption capacity increases.
Under above-mentioned preferred adsorption conditions, ion-exchanger obtained by above-described embodiment is used for adsorption of cobalt, manganese ion
Experiment:
200 mL are taken, ion concentration is the cobalt of 100 ppm, manganese Metal titer in 250 mL conical flasks, and 0.3 g is added
Ion-exchanger obtained by above-described embodiment samples after 120 min under 25 DEG C, 160 rpm of thermostatic control oscillator vibration, utilizes electricity
Feel coupled plasma-atomic emission spectrometry (ICP-AES) and measure cobalt, manganese ion concentration, calculates the absorption of cobalt, manganese ion
Amount, acquired results are listed in table 1.
Table 1: ion-exchanger obtained by above-described embodiment is for adsorbing the adsorbance of the cobalt in PAT waste water, manganese ion
As can be known from the results of Table 1: present invention gained ion-exchanger can be used for adsorbing cobalt, manganese ion in PAT waste water.
The desorption experiment of 2 ion-exchanger 2 of the gained based on modified resin of embodiment:
Using the hydrochloric acid of 2 mol/L as strippant, the ion-exchanger 2 for adsorbing cobalt, manganese ion is desorbed again
It is raw.Fig. 4 is the desorption and regenerated effect of ion-exchanger 2 during 4 adsorption-desorption cycles.All in all, hydrochloric acid conduct
Strippant, after 4 circulations, desorption efficiency reaches 90% or more, and adsorption capacity decline is smaller, thus present invention gained from
Sub- exchanger is as Co in processing PTA waste water2+、Mn2+The excellent ionic exchanger of metal ion, it is reusable.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (4)
1. a kind of preparation method of the ion-exchanger based on modified resin, it is characterised in that: the ion-exchanger is to pass through
5-sulphosalicylic acid is modified Amberlite XAD-4 resin and is made, and the structure of gained ion-exchanger is as follows:
, whereinIndicate the basic of Amberlite XAD-4 resin
Skeleton structure；Preparation method, comprising the following steps:
(1) 3 ~ 5 g Amberlite XAD-4 resins are dissolved in 10 ~ 20 mL octanols, the chloromethyl of 20 ~ 30 mL is then added
5 ~ 10 g anhydrous acid catalysts are added portionwise in agent under stirring, after reacting 2 ~ 10 h at 40 ~ 90 DEG C, successively use acetone, salt
After acid, distilled water cleaning, dry 8 h, obtain chloromethylation products at 60 DEG C；
(2) after step (1) resulting chloromethylation products sufficiently being impregnated 2 h in 30 mL solvents, 2 ~ 5 g 5- sulfo groups are added
Salicylic acid, after reacting 24 ~ 72 h at 70 ~ 100 DEG C, after successively being cleaned with acetone, hydrochloric acid, distilled water, dry 8 at 60 DEG C
H is to get the ion-exchanger based on modified resin.
2. preparation method according to claim 1, it is characterised in that: chloromethyl agent as described in step (1) is dichloro
Methane or chloromethyl methyl ether.
3. preparation method according to claim 1, it is characterised in that: anhydrous acid catalysts as described in step (1) are nothing
Water alchlor or anhydrous zinc chloride.
4. preparation method according to claim 1, it is characterised in that: solvent described in step (2) is dichloroethanes, nitre
Base benzene or N-N- dimethylformamide.
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| CN103551129A (en) * | 2013-11-15 | 2014-02-05 | 天津工业大学 | Preparation and application of heavy metal ion adsorption fiber with wide pH application range |
| CN103819589A (en) * | 2014-03-12 | 2014-05-28 | 李京昊 | Salicylic acid-type polystyrene chelate ion exchange resin |
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| CN103551129A (en) * | 2013-11-15 | 2014-02-05 | 天津工业大学 | Preparation and application of heavy metal ion adsorption fiber with wide pH application range |
| WO2015076586A1 (en) * | 2013-11-20 | 2015-05-28 | Samsung Electronics Co., Ltd. | Composition for electrode of capacitive deionization apparatus, and electrode including same |
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