CN103464119A - Preparation method and application of modified cysteine palm bark adsorbent - Google Patents
Preparation method and application of modified cysteine palm bark adsorbent Download PDFInfo
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Abstract
The invention discloses a preparation method and application technology of modified cysteine palm bark adsorbent. The preparation method and application technology of the modified cysteine palm bark adsorbent are characterized in that palm barks are placed into a container to be soaked with water and dried and smashed, the smashed palm barks are processed with isopropyl alcohol and a NaOH solution and then soaked and boiled with an epoxy chloropropane and NaOH mixed solution, suction filtration and drying are performed, and epoxy group palm tree barks are obtained. By mass, 3-11% of cysteine, 9-26% of epoxy group palm bark, 4-12% of sodium carbonate and 52-82% of water are added in a reactor, the sum of the percentages of all the components is 100%, the mixture is stirred and has an overflow reaction at the constant temperature of 50 +/- 3 DEG C for 4-8 hours, after the mixture is cooled, the mixture is washed with deionized water and processed in a suction filtration mode until filtrate is neutral, the mixture is placed in a vacuum drying box at 40 +/- 5 DEG C to be dried after being washed with a little amount of ethanol, and modified cysteine palm barks are obtained. The adsorbent is high in adsorption efficiency on metal ions and speed, good in desorbing performance, high in mechanical performance and regeneration capacity, low in cost and environmentally friendly.
Description
Technical field
The preparation method who the present invention relates to a kind of biological adsorption agent reaches the applied technical field to heavy metal adsorption, and particularly a kind of cysteine modification palm bark absorbent preparation method reaches heavy metal ion adsorbed application technology.
Background technology
Heavy metal, particularly mercury, cadmium, lead, chromium etc. have remarkable toxicity, and they can not be degraded by microorganisms in water body, and can only occur that various forms transform mutually and dispersion, enrichment process.Heavy metal has very high toxicity and carcinogenicity to the organism lived, and enrichment in vivo, accumulation produce very high toxicity, but also can produce enlarge-effect by food chain.The toxicity produced due to heavy metal can not biodegradation, exists the heavy metal ion in water body, soil environment day by day to be subject to people's attention.Remove heavy metal and usually adopt chemical precipitation method, flocculence, ion-exchange and electrolysis etc., but all there are the shortcomings such as expense is high, efficiency is low in these methods.In recent years, utilize natural polymer subbundle (as cotton, fiber crops, palm bark, luffa, bagasse, peanut shell etc.) modification to synthesize various adsorbents, that this adsorbent has is inexpensive, be easy to get, the advantage such as renewable, biodegradable.
Palm is perennial aiphyllium plant, 7 meters of Gao Keda; Dry upright, branch not, the palm-bark rain cape formed by leaf sheath is wrapped; Therefore the fiber of palm bark is very long, intensity is large, is typically used as the making mattress, is one of most valuable ecological resources, is a kind of renewable resource.Palm is extensively planted area on the south the Changjiang river at present, is very precious long fibered raw material.This natural macromolecular material application is made absorption and is had natural, green, biodegradable, mechanical strength is large, the characteristics such as resistance to corrosion is strong, the palm bark is reused repeatedly as adsorbent is renewable, and dyestuff is had to larger adsorption capacity, abroad the research of palm bark chemical modification and absorption property is reported seldom, Chinese Patent Application No. is: disclose a kind of preparation method and application of sulfydryl palm bark adsorbent in 201310147720.6 patent, it is characterized in that: in reactor, by following composition mass percent, add, thioglycolic acid: 30 ~ 45%, oxolane: 25 ~ 40%, alkalization palm bark: 20 ~ 35%, glacial acetic acid: 0.5 ~ 2.5%, the concentrated sulfuric acid: 0.15 ~ 0.3%, each component sum is absolutely, jump a queue, under 40 ~ 45 ℃, arrest reaction 48 ~ 60 h, then by deionized water, wash, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed in 35 ~ 45 ℃ of baking ovens dry, obtain sulfydryl palm bark adsorbent.Its sulfydryl palmitic acid bark adsorbent is to Cd
2+adsorption capacity can be up to 286mg/g, to Pb
2+maximal absorptive capacity be 521mg/g, to Cu
2+maximal absorptive capacity be 165mg/g, high adsorption rate can reach 98%.
Cysteine is a kind of common amino acid, there is effective detoxication and anti-aging effects, therefore there do not is the problem of contaminated environment, in addition the mercapto groups on cysteine side chain and carboxylic group be all can with the functional group of heavy metal combination, adopt the cysteine modification to prepare adsorbent report is also arranged, Li Qing etc., studied cysteine modified mesoporous material absorption Hg
2+, (Li Qing etc., the cysteine modified mesoporous material is to Hg
2+high selectivity separation and concentration performance study, analytical chemistry, 2013,41(1): 93 ~ 97); Yang Yaling etc., studied the cysteine using modified bagasse to Cd
2+absorption property, it is to Cd
2+maximum adsorption capacity be: 122.75mg/g, (Yang Yaling etc., epoxychloropropane and cysteine using modified bagasse are to Cd
2+absorption, Yunnan chemical, 2010,34(1), 11 ~ 14).Utilizing the standby adsorbent of cysteine modification palm leather, have the character that sulfydryl and some heavy metal ion have very strong huge legendary turtle cooperation to use, have again the advantages such as renewable, degradable, the environmental protection of natural polymer be friendly, cheap, is important living resources.Utilize cysteine modification palm leather to obtain adsorbent and have no report.
Summary of the invention
One of purpose of the present invention is to provide a kind of cysteine modification palm bark absorbent preparation method, mainly make the cysteine modification palm bark adsorbent that obtains larger as the adsorption capacity of Heavy Metals in Waters adsorbent, by regulating the difference of pH value, can make heavy metal ion reach the purpose of separation.
Purpose of the present invention is achieved through the following technical solutions.
A kind of cysteine modification palm bark absorbent preparation method is characterised in that the method has following processing step:
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, putting into container is soaked in water 24 ~ 48 hours, after vacuum drying, pulverized, the palm bark of drying and crushing be take to the ratio that solid-to-liquid ratio is 50 ~ 100g/L, with the NaOH solution of isopropyl alcohol and 1.0 ~ 3.5mol/L, be the mixed solution of 1:4 ~ 10 by volume, soaking at room temperature 12 ~ 20h, boil 10 ~ 30nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 50 ~ 60 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: above-mentioned pretreatment palm bark is pressed to 100 ~ 200g/L solid-to-liquid ratio, press the mixed solution of 1:3 ~ 6 volume ratios with the NaOH solution of epoxychloropropane and 1.0 ~ 3.5mol/L, soaking at room temperature 12 ~ 20 h, boil again 10 ~ 20min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ~ 65 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add cysteine by following composition mass percent: 3 ~ 11%, and epoxy radicals palm bark: 9 ~ 26%, sodium carbonate: 4 ~ 12%; Water: 52 ~ 82%, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 4 ~ 8 h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark, wherein the mass ratio of cysteine and sodium carbonate is between 1:1 ~ 1.5.
Another object of the present invention be to provide a kind of cysteine modification palm bark adsorbent in aqueous systems to heavy metal ion, as Cd
2+, Pb
2+, Hg
2+, Cu
2+absorption, characteristics are: deionized water for the cysteine modification palm bark adsorbent for preparing is soaked to 2 ~ 4h, by static method absorption.
The ring cysteine modification palm bark adsorbent prepared is soaked to 2 ~ 4h by deionized water, by dynamic method absorption.
Advantage of the present invention and effect are:
(1) the cysteine modification palm bark adsorbent that the present invention obtains has good physical and chemical stability and excellent mechanical strength, the adsorption capacity that compares heavy metal with modified peanut, bagasse is large, wear-resisting, Reusability often, can reach more than 10 times;
(2) absorption and the wash-out of the cysteine modification palm bark adsorbent that the present invention obtains to the Heavy Metals in Waters ion, adsorption efficiency is high, and speed is fast, and desorption performance is good, can in wider soda acid scope, use;
(3) good stability, be the natural green product, biodegradable;
(4) the synthetic condition of crossing range request is easily controlled, and energy consumption is low, simple to operate, in whole production process, without " three wastes " discharge, belongs to process for cleanly preparing, is easy to suitability for industrialized production.
The specific embodiment
Embodiment 1
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 24h that is soaked in water, pulverized after vacuum drying, palm bark 10g by drying and crushing, with the mixed solution of 40mL isopropyl alcohol and 160mL 1.0mol/L NaOH, soaking at room temperature 15h, boil 20nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 55 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 10g, mixed solution with 20mL epoxychloropropane and 100mL3.0mol/L NaOH, soaking at room temperature 12 h, boil again 15min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 4g, epoxy radicals palm bark: 10g, sodium carbonate: 5g; Water: 81mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 5 h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 2
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 40h that is soaked in water, pulverized after vacuum drying, palm bark 20g by drying and crushing, with the mixed solution of 50mL isopropyl alcohol and 300mL 2.0mol/L NaOH, soaking at room temperature 12h, boil 30nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 50 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 20g, mixed solution with 30mL epoxychloropropane and 180mL2.0mol/L NaOH, soaking at room temperature 20 h, boil again 10min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 60 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 4g, epoxy radicals palm bark: 10g, sodium carbonate: 5g; Water: 81mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 6h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 3
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 32h that is soaked in water, pulverized after vacuum drying, palm bark 30g by drying and crushing, with the mixed solution of 50mL isopropyl alcohol and 250mL 3.0mol/L NaOH, soaking at room temperature 20h, boil 10nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 60 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 20g, mixed solution with 50mL epoxychloropropane and 150mL3.5mol/L NaOH, soaking at room temperature 15 h, boil again 20min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 6g, epoxy radicals palm bark: 12g, sodium carbonate: 6.5g; Water: 31mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 8 h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 4
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 24h that is soaked in water, pulverized after vacuum drying, palm bark 10g by drying and crushing, with the mixed solution of 40mL isopropyl alcohol and 160mL 1.0mol/L NaOH, soaking at room temperature 15h, boil 20nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 55 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 10g, mixed solution with 20mL epoxychloropropane and 100mL3.0mol/L NaOH, soaking at room temperature 12 h, boil again 15min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 4g, epoxy radicals palm bark: 6g, sodium carbonate: 5g; Water: 35mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 5 h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 5
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 40h that is soaked in water, pulverized after vacuum drying, palm bark 20g by drying and crushing, with the mixed solution of 50mL isopropyl alcohol and 300mL 2.0mol/L NaOH, soaking at room temperature 12h, boil 30nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 50 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 20g, mixed solution with 30mL epoxychloropropane and 180mL2.0mol/L NaOH, soaking at room temperature 20 h, boil again 10min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 60 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 5g, epoxy radicals palm bark: 10g, sodium carbonate: 5g; Water: 30mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 6h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 6
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, put into the container 32h that is soaked in water, pulverized after vacuum drying, palm bark 30g by drying and crushing, with the mixed solution of 50mL isopropyl alcohol and 250mL 3.0mol/L NaOH, soaking at room temperature 20h, boil 10nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 60 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: by above-mentioned pretreatment palm bark 20g, mixed solution with 50mL epoxychloropropane and 150mL3.5mol/L NaOH, soaking at room temperature 15 h, boil again 20min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add respectively cysteine: 3g, epoxy radicals palm bark: 18g, sodium carbonate: 4g; Water: 75mL, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 7h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
Embodiment 7
Cysteine modification palm bark prepared by above embodiment, adopt chemical method to detect its sulfhydryl content identical.
Cysteine modification palm bark application process: the cysteine modification palm bark prepared is spent to ionized water and soaks 2 h, by a kind of be static adsorptive method, another kind is dynamic adsorption method, and adsorption of metal ions is applied.
Measure absorption property with static adsorptive method, get the metal ion solution 20mL of variable concentrations, the cysteine modification palm bark that adds under the same conditions equivalent, concussion absorption 0.5 h gets clear liquid, by the concentration of metal ion in the atomic absorption detecting clear liquid, according to metal ion solution change in concentration before and after absorption, calculate adsorption rate.
Measure absorption property by dynamic method, by a certain amount of cysteine modification palm bark with the wet method adsorption column of packing into, get the metal ion solution of variable concentrations, regulate the pH value with diluted acid and diluted alkaline, flow velocity with 2 mL/min passes through adsorption column, by the amount of metal ion of adsorbing on atomic absorption detecting filtered fluid and post, calculate thus adsorption rate.
Prepare as stated above the application of cysteine modification palm bark in adsorption of metal ions.Cysteine modification palm bark of the present invention the adsorption of metal ions field be applied as directly to water body in absorption and the wash-out of each metal ion species.Its method is:
(1) for containing K
+, Na
+, Ca
2+, Mg
2+, Ba
2+, Al
3+, Cu
2+, Zn
2+, Cd
2+, Fe
3+, Ag
+, Co
2+, Ni
2+, Pb
2+, Se
4+, Pt
4+, Pd
2+, Au
3+in one or more staying water system, adopt cysteine modification palm bark to carry out water treatment with the method for Static Adsorption, get cysteine modification palm bark and be immersed in staying water system, 0.5 h is adsorbed in concussion, its Adsorption law is as follows:
A. for alkali and alkaline earth metal ions if any K
+, Na
+, Ca
2+, Mg
2+, Ba
2+, Al
3+deng not adsorbing, do not affect the absorption property of cysteine modification palm bark while having alkali and alkaline earth metal ions in sample thus.
B. for precious metal ion, stronger absorption property is arranged, the strong and weak order of absorption is: Pt
4+au
3+?
?pd
2+ag
+.
C. heavy metal ion is also had to stronger absorption property, the strong and weak order of absorption is: Se
4+, Ag
+cu
2+fe
3+, Pb
2+zn
2+cd
2+co
2+, Ni
2+.
Adsorption capacity is relevant with the factors such as pH value of sulfhydryl content consumption, adsorption temp, solution system in cysteine modification palm bark.
(2) for containing K
+, Na
+, Ca
2+, Mg
2+, Ba
2+, Al
3+, Cu
2+, Zn
2+, Cd
2+, Fe
3+, Ag
+, Co
2+, Ni
2+, Pb
2+, Se
4+, Pt
4+, Pd
2+, Au
3+in one or more staying water system, adopt cysteine modification palm bark to carry out water treatment by the method for Dynamic Adsorption, the rule of its absorption is the same, and the pH value of adsorption capacity and sulfhydryl content consumption, adsorption temp, solution system in cysteine modification palm bark, the factors such as flow velocity of solution are relevant.
The cysteine modification palm bark obtained is to Cd
2+adsorption capacity can be up to 295mg/g, to Pb
2+maximal absorptive capacity be 533mg/g, to Cu
2+maximal absorptive capacity be 179mg/g, Hg
2+maximal absorptive capacity be 492mg/g, high adsorption rate can reach 99%.
Claims (5)
1. a cysteine modification palm bark absorbent preparation method is characterised in that the method has following processing step:
(1) palm bark pretreatment: the palm bark is cut into small pieces, wash with water and remove earth and impurity, putting into container is soaked in water 24 ~ 48 hours, after vacuum drying, pulverized, the palm bark of drying and crushing be take to the ratio that solid-to-liquid ratio is 50 ~ 100g/L, with the NaOH solution of isopropyl alcohol and 1.0 ~ 3.5mol/L, be the mixed solution of 1:4 ~ 10 by volume, soaking at room temperature 12 ~ 20h, boil 10 ~ 30nim, cooling rear extremely neutral with the deionized water washing, suction filtration, 50 ~ 60 ℃ of oven dry, obtain pretreatment palm bark;
(2) epoxy radicals palm leather is standby: above-mentioned pretreatment palm bark is pressed to 100 ~ 200g/L solid-to-liquid ratio, press the mixed solution of 1:3 ~ 6 volume ratios with the NaOH solution of epoxychloropropane and 1.0 ~ 3.5mol/L, soaking at room temperature 12 ~ 20 h, boil again 10 ~ 20min, cooling rear extremely neutral with the deionized water washing, ethanol washing is again dried after suction filtration under 55 ~ 65 ℃, obtains epoxy radicals palm bark;
(3) cysteine modification palm leather is standby: in reactor, add cysteine by following composition mass percent: 3 ~ 11%, and epoxy radicals palm bark: 9 ~ 26%, sodium carbonate: 4 ~ 12%; Water: 52 ~ 82%, each component sum is absolutely, in 50 ± 3 ℃ of constant temperature, stirring, back flow reaction 4 ~ 8 h, after cooling, with deionized water washing, suction filtration, till being neutrality to filtrate, with after a small amount of ethanol washing, be placed on drying in 40 ± 5 ℃ of vacuum drying chambers, obtain cysteine modification palm bark.
2. according to the cysteine modification palm bark absorbent preparation described in claim 1, it is characterized in that: in step (2), the volume ratio of the NaOH solution of epoxychloropropane and 1.0 ~ 3.5mol/L is 1:3 ~ 6.
3. according to the cysteine modification palm bark absorbent preparation described in claim 1, it is characterized in that: in step (3), the mass ratio of cysteine and sodium carbonate is between 1:1 ~ 1.5.
4. according to the cysteine modification palm bark absorbent preparation described in claim 1, it is characterized in that: the cysteine described in step (3) is Cys or D-Cys.
5. according to the cysteine modification palm bark absorbent preparation described in claim 1, it is characterized in that: to Cd in water
2+, Pb
2+, Hg
2+, Cu
2+the application of absorption.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104289187A (en) * | 2014-09-10 | 2015-01-21 | 济南大学 | Preparation of dimethyl diallyl ammonium chloride modified towel gourd vegetable sponge adsorbent |
| CN104289189A (en) * | 2014-09-10 | 2015-01-21 | 济南大学 | Preparation of dimethyl diallyl ammonium chloride modified palm tree bark adsorbent |
| CN104624164A (en) * | 2015-01-24 | 2015-05-20 | 浙江工商大学 | L-cysteine-modified cellulose, as well as preparation method and application thereof |
| CN105664869A (en) * | 2016-02-17 | 2016-06-15 | 济南大学 | Preparation of lauramidopropyl betaine modified palm tree bark adsorbent |
| CN106423072A (en) * | 2016-09-21 | 2017-02-22 | 广东环境保护工程职业学院 | Graphene oxide-sulfhydryl compound composite capable of adsorbing heavy metal ions and preparation method of graphene oxide-sulfhydryl compound composite |
| CN107226507A (en) * | 2017-06-26 | 2017-10-03 | 云南圣清环保科技有限公司 | A kind of preparation method of the cysteine-modifying celluloses of L for removal of heavy metal ions |
| CN107552016A (en) * | 2017-08-17 | 2018-01-09 | 江苏理工学院 | A kind of preparation method and applications of cysteine-modifying Organic Polymer Monolithic Columns |
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| CN104289187A (en) * | 2014-09-10 | 2015-01-21 | 济南大学 | Preparation of dimethyl diallyl ammonium chloride modified towel gourd vegetable sponge adsorbent |
| CN104289189A (en) * | 2014-09-10 | 2015-01-21 | 济南大学 | Preparation of dimethyl diallyl ammonium chloride modified palm tree bark adsorbent |
| CN104289187B (en) * | 2014-09-10 | 2016-08-24 | 济南大学 | A kind of preparation of dimethyl diallyl ammonium chloride modified loofah sponge adsorbent |
| CN104289189B (en) * | 2014-09-10 | 2016-10-26 | 济南大学 | A kind of dimethyl diallyl ammonium chloride modifies the preparation of palm bark adsorbent |
| CN104624164A (en) * | 2015-01-24 | 2015-05-20 | 浙江工商大学 | L-cysteine-modified cellulose, as well as preparation method and application thereof |
| CN104624164B (en) * | 2015-01-24 | 2017-04-12 | 浙江工商大学 | L-cysteine-modified cellulose, as well as preparation method and application thereof |
| CN105664869A (en) * | 2016-02-17 | 2016-06-15 | 济南大学 | Preparation of lauramidopropyl betaine modified palm tree bark adsorbent |
| CN106423072A (en) * | 2016-09-21 | 2017-02-22 | 广东环境保护工程职业学院 | Graphene oxide-sulfhydryl compound composite capable of adsorbing heavy metal ions and preparation method of graphene oxide-sulfhydryl compound composite |
| CN107226507A (en) * | 2017-06-26 | 2017-10-03 | 云南圣清环保科技有限公司 | A kind of preparation method of the cysteine-modifying celluloses of L for removal of heavy metal ions |
| CN107552016A (en) * | 2017-08-17 | 2018-01-09 | 江苏理工学院 | A kind of preparation method and applications of cysteine-modifying Organic Polymer Monolithic Columns |
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