CN109666155A - A kind of cross-linking modified lignin chelating agent and preparation method thereof - Google Patents
A kind of cross-linking modified lignin chelating agent and preparation method thereof Download PDFInfo
- Publication number
- CN109666155A CN109666155A CN201710952822.3A CN201710952822A CN109666155A CN 109666155 A CN109666155 A CN 109666155A CN 201710952822 A CN201710952822 A CN 201710952822A CN 109666155 A CN109666155 A CN 109666155A
- Authority
- CN
- China
- Prior art keywords
- lignin
- crosslinking
- etherificate
- sodium hydroxide
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 92
- 238000004132 cross linking Methods 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000002738 chelating agent Substances 0.000 title claims abstract description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 90
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000926 separation method Methods 0.000 claims abstract description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 10
- 238000006266 etherification reaction Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims abstract description 5
- 235000019341 magnesium sulphate Nutrition 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- OJJMXFQXXKZRMG-UHFFFAOYSA-N hydroxymethyl(dimethyl)azanium;chloride Chemical group [Cl-].C[NH+](C)CO OJJMXFQXXKZRMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000007873 sieving Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 238000004065 wastewater treatment Methods 0.000 abstract description 3
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 abstract description 2
- 238000004537 pulping Methods 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000006071 cream Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/26—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof
- C02F2103/28—Nature of the water, waste water, sewage or sludge to be treated from the processing of plants or parts thereof from the paper or cellulose industry
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2397/00—Characterised by the use of lignin-containing materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
The invention discloses a kind of preparation methods of cross-linking modified lignin chelating agent, include the following steps: to add suitable quantity of water in crosslinking etherificate lignin, it stirs evenly, sodium hydroxide is slowly added dropwise, carbon disulfide is then added, is reacted at 50-60 DEG C, separation product after the reaction was completed, then magnesium sulfate is added, the reaction was continued, and the cross-linking modified lignin chelating agent is obtained after being separated, washed, dried after the reaction was completed.The present invention uses lignin for raw material, carries out first to it etherification modified, obtains crosslinking etherificate lignin and is then based on this further crosslinked by carbon disulfide, obtains a kind of adsorption of metal ions performance more preferably chelating agent.Have many advantages, such as that raw material sources are wide, it is at low cost, there is application value in fields such as pulping wastewater treatments.
Description
Technical field
The present invention relates to water treatment fields, and in particular to a kind of cross-linking modified lignin chelating agent and preparation method thereof.
Background technique
Novel Wastewater processing absorbent is developed using modified lignin resin, water purification quality not only can be improved and reduce cost,
And China is large agricultural country, lignin yield is at the forefront in the world, with lignin derivative production wastewater treatment adsorbent, favorably
In the development of lignin deep processing, and take full advantage of the Liginon Resource in China.There is presently no changed using lignin preparation
The report of property chelating agent.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of cross-linking modified lignin chelating agent, are deposited with solving background technique
Drawbacks described above.
The present invention realizes by the following technical solutions:
A kind of preparation method of cross-linking modified lignin chelating agent includes the following steps: to add in crosslinking etherificate lignin
Suitable quantity of water stirs evenly, and sodium hydroxide is slowly added dropwise, carbon disulfide is then added, and reacts at 50-60 DEG C, after the reaction was completed
Then separation product adds magnesium sulfate, the reaction was continued, and the crosslinking is obtained after being separated, washed, dried after the reaction was completed and is changed
Property lignin chelating agent.
The mass content of each component is as follows as a preferred technical solution:
Sodium hydroxide is made into the aqueous solution of 0.2g/mL as a preferred technical solution, and magnesium sulfate is made into the water of 0.1g/mL
Solution.
The crosslinking etherificate lignin is prepared with the following method as a preferred technical solution:
Step 1 mixes lignin and sodium hydroxide, and suitable quantity of water is added, is heated to 50-70 DEG C, is slowly added to epoxy second
Alkane is reacted, and is adjusted with acid pH value to neutrality, after being separated, washed, dried, is obtained crosslinking lignin；
The crosslinking lignin is dispersed in alcohol by step 2, etherifying agent and sodium hydroxide is added, in 40-60 DEG C of condition
Lower carry out etherification reaction obtains the crosslinking etherificate lignin after separation is dry.
200 mesh sieving rates of the lignin are greater than 95% as a preferred technical solution,.
As a preferred technical solution, in the crosslinking etherificate lignin preparation step, lignin, sodium hydroxide and epoxy
The mass ratio of ethane is 1:1.25:1.
As a preferred technical solution, in the crosslinking etherificate lignin preparation step, the acid is that 25wt% acetic acid is molten
Liquid, the sodium hydroxide are configured to the aqueous solution of mass concentration 25%.
As a preferred technical solution, in the crosslinking etherificate lignin preparation step, the alcohol is ethyl alcohol.
As a preferred technical solution, in the crosslinking etherificate lignin preparation step, each component quality contains in step 2
It measures as follows:
100 parts of lignin of crosslinking,
5-10 parts of sodium hydroxide,
10-25 parts of etherifying agent.
As a preferred technical solution, in the crosslinking etherificate lignin preparation step, etherifying agent is hydroxymethyl dimethylamine
Hydrochloride, etherification reaction time are 2-6 hours.
The present invention uses lignin for raw material, it is carried out first it is etherification modified, obtain crosslinking etherificate lignin, then with
It based on this, is further crosslinked by carbon disulfide, obtains a kind of adsorption of metal ions performance more preferably chelating agent.This kind of chelating
Agent has many advantages, such as that raw material sources are wide, at low cost, has application value in fields such as pulping wastewater treatments.
Specific embodiment
The present invention is illustrated below by specific embodiment, but is not intended to limit the present invention.
Embodiment 1
1. lignin is stirred with mass concentration for 25% sodium hydroxide solution, water-bath at 65 DEG C by 1:5 in mass ratio
Heating.Ethylene oxide identical with lignin quality is slowly added dropwise, adjusts pH to 7.0 with 25% acetic acid solution, staticly settles half
Hour, by separation, wash, it is dry, obtain crosslinking lignin.
2. to lignin carry out it is etherification modified, by lignin dispersion in ethanol, be added lignin quality 8% NaOH with
And the hydroxymethyl dimethylamine hydrochloride of lignin quality 18%, it is reacted 5 hours under the conditions of 50 DEG C, it is spare after separation is dry.
3. accurately weighing a certain amount of crosslinking etherificate lignin, the lignin cream that quality is 20% is made, stirs evenly.It is slow
It is slow that 0.2g/mL sodium hydroxide is added dropwise, carbon disulfide is then added, reacts 2h in 50 DEG C of water-bath.Taking-up adds 0.1g/
ML Adlerika, the reaction was continued 15min.Wherein, by mass, ratio is as follows for each reactant of this step:
100 parts of lignin of etherificate
200 parts of 0.2g/mL sodium hydroxide
70 parts of carbon disulfide
300 parts of 0.1g/mL Adlerika
3. after reaction stops, washing, filters, successively washed 2 times with acetone, ether later.
4. then vacuum drying obtains double cross connection lignin etherifying agent.
Embodiment 2
1. lignin is stirred with mass concentration for 25% sodium hydroxide solution, water-bath at 65 DEG C by 1:5 in mass ratio
Heating.Ethylene oxide identical with lignin quality is slowly added dropwise, adjusts pH to 7.0 with 25% acetic acid solution, staticly settles half
Hour, by separation, wash, it is dry, obtain crosslinking lignin.
2. to lignin carry out it is etherification modified, by lignin dispersion in ethanol, be added lignin quality 8% NaOH with
And the hydroxymethyl dimethylamine hydrochloride of lignin quality 18%, it is reacted 5 hours under the conditions of 50 DEG C, it is spare after separation is dry.
3. accurately weighing a certain amount of crosslinking etherificate lignin, the lignin cream that quality is 20% is made, stirs evenly.It is slow
It is slow that 0.2g/mL sodium hydroxide is added dropwise, carbon disulfide is then added, reacts 2h in 50 DEG C of water-bath.Taking-up adds 0.1g/
ML Adlerika, the reaction was continued 15min.Wherein, by mass, ratio is as follows for each reactant of this step:
100 parts of lignin of etherificate
150 parts of 0.2g/mL sodium hydroxide
60 parts of carbon disulfide
300 parts of 0.1g/mL Adlerika
3. after reaction stops, washing, filters, successively washed 2 times with acetone, ether later.
4. then vacuum drying obtains double cross connection lignin etherifying agent.
Embodiment 3
1. lignin is stirred with mass concentration for 25% sodium hydroxide solution, water-bath at 65 DEG C by 1:5 in mass ratio
Heating.Ethylene oxide identical with lignin quality is slowly added dropwise, adjusts pH to 7.0 with 25% acetic acid solution, staticly settles half
Hour, by separation, wash, it is dry, obtain crosslinking lignin.
2. to lignin carry out it is etherification modified, by lignin dispersion in ethanol, be added lignin quality 8% NaOH with
And the hydroxymethyl dimethylamine hydrochloride of lignin quality 18%, it is reacted 5 hours under the conditions of 50 DEG C, it is spare after separation is dry.
3. accurately weighing a certain amount of crosslinking etherificate lignin, the lignin cream that quality is 20% is made, stirs evenly.It is slow
It is slow that 0.2g/mL sodium hydroxide is added dropwise, carbon disulfide is then added, reacts 2h in 50 DEG C of water-bath.Taking-up adds 0.1g/
ML Adlerika, the reaction was continued 15min.Wherein, by mass, ratio is as follows for each reactant of this step:
100 parts of lignin of etherificate
180 parts of 0.2g/mL sodium hydroxide
70 parts of carbon disulfide
310 parts of 0.1g/mL Adlerika
3. after reaction stops, washing, filters, successively washed 2 times with acetone, ether later.
4. then vacuum drying obtains double cross connection lignin etherifying agent.
Embodiment 4
1. lignin is stirred with mass concentration for 25% sodium hydroxide solution, water-bath at 65 DEG C by 1:5 in mass ratio
Heating.Ethylene oxide identical with lignin quality is slowly added dropwise, adjusts pH to 7.0 with 25% acetic acid solution, staticly settles half
Hour, by separation, wash, it is dry, obtain crosslinking lignin.
2. to lignin carry out it is etherification modified, by lignin dispersion in ethanol, be added lignin quality 8% NaOH with
And the hydroxymethyl dimethylamine hydrochloride of lignin quality 18%, it is reacted 5 hours under the conditions of 50 DEG C, it is spare after separation is dry.
3. accurately weighing a certain amount of crosslinking etherificate lignin, the lignin cream that quality is 20% is made, stirs evenly.It is slow
It is slow that 0.2g/mL sodium hydroxide is added dropwise, carbon disulfide is then added, reacts 2h in 50 DEG C of water-bath.Taking-up adds 0.1g/
ML Adlerika, the reaction was continued 15min.Wherein, by mass, ratio is as follows for each reactant of this step:
100 parts of lignin of etherificate
200 parts of 0.2g/mL sodium hydroxide
80 parts of carbon disulfide
320 parts of 0.1g/mL Adlerika
3. after reaction stops, washing, filters, successively washed 2 times with acetone, ether later.
4. then vacuum drying obtains double cross connection lignin etherifying agent.
Comparative example
Using both sexes lignin chelating agent as comparative sample, configuration quality concentration be 0.03% Cr2+Solution, 0.002% Cu2 +Solution, 0.006% Ni2+Solion, fixing metal ions/chelating agent mass ratio are 0.10, chelating agent are added, placement is shaken
Bed constant temperature oscillation, is drawn off after a period of time, is centrifugated, and obtains supernatant liquor, measures the ion concentration in supernatant, meter
Calculate complexation of metal ions content.Concrete outcome such as table 1:
Table 1
As can be seen from the table, adsorption of metal ions effect of the invention is substantially better than comparative example.
The above shows and describes the basic principle, main features and advantages of the invention.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (10)
1. a kind of preparation method of cross-linking modified lignin chelating agent, which comprises the steps of: in crosslinking etherificate wood
Add suitable quantity of water in quality, stirs evenly, sodium hydroxide is slowly added dropwise, carbon disulfide is then added, reacted at 50-60 DEG C, instead
Separation product after the completion of answering, then adds magnesium sulfate, and the reaction was continued, and institute is obtained after being separated, washed, dried after the reaction was completed
State cross-linking modified lignin chelating agent.
2. the method as described in claim 1, which is characterized in that the mass content of each component is as follows:
3. the method as described in claim 1, which is characterized in that sodium hydroxide is made into the aqueous solution of 0.2g/mL, and magnesium sulfate is made into
The aqueous solution of 0.1g/mL.
4. the method as described in claim 1, which is characterized in that the crosslinking etherificate lignin is prepared with the following method:
Step 1 mixes lignin and sodium hydroxide, and suitable quantity of water is added, is heated to 50-70 DEG C, be slowly added to ethylene oxide into
Row reaction is adjusted with acid pH value to neutrality, after being separated, washed, dried, obtains crosslinking lignin；
The crosslinking lignin is dispersed in alcohol by step 2, and etherifying agent and sodium hydroxide is added, under the conditions of 40-60 DEG C into
Row etherification reaction obtains the crosslinking etherificate lignin after separation is dry.
5. method as claimed in claim 4, which is characterized in that 200 mesh sieving rates of the lignin are greater than 95%.
6. method as claimed in claim 4, which is characterized in that in the crosslinking etherificate lignin preparation step, lignin, hydrogen
The mass ratio of sodium oxide molybdena and ethylene oxide is 1:1.25:1.
7. method as claimed in claim 4, which is characterized in that in the crosslinking etherificate lignin preparation step, the acid is
25wt% acetic acid solution, the sodium hydroxide are configured to the aqueous solution of mass concentration 25%.
8. method as claimed in claim 4, which is characterized in that in the crosslinking etherificate lignin preparation step, the alcohol is
Ethyl alcohol.
9. method as claimed in claim 4, which is characterized in that in the crosslinking etherificate lignin preparation step, in step 2
Each component mass content is as follows:
100 parts of lignin of crosslinking,
5-10 parts of sodium hydroxide,
10-25 parts of etherifying agent.
10. method as claimed in claim 4, which is characterized in that in the crosslinking etherificate lignin preparation step, etherifying agent is
Hydroxymethyl dimethylamine hydrochloride, etherification reaction time are 2-6 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710952822.3A CN109666155A (en) | 2017-10-13 | 2017-10-13 | A kind of cross-linking modified lignin chelating agent and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710952822.3A CN109666155A (en) | 2017-10-13 | 2017-10-13 | A kind of cross-linking modified lignin chelating agent and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109666155A true CN109666155A (en) | 2019-04-23 |
Family
ID=66138709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710952822.3A Pending CN109666155A (en) | 2017-10-13 | 2017-10-13 | A kind of cross-linking modified lignin chelating agent and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109666155A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113214004A (en) * | 2021-05-11 | 2021-08-06 | 深圳市华创汇能技术有限公司 | Preparation method and application of chelating lignin-based water-retention slow-release copper fertilizer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106589405A (en) * | 2016-12-22 | 2017-04-26 | 上海东升新材料有限公司 | Lignin metal ion chelating agent and preparation method thereof |
-
2017
- 2017-10-13 CN CN201710952822.3A patent/CN109666155A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106589405A (en) * | 2016-12-22 | 2017-04-26 | 上海东升新材料有限公司 | Lignin metal ion chelating agent and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113214004A (en) * | 2021-05-11 | 2021-08-06 | 深圳市华创汇能技术有限公司 | Preparation method and application of chelating lignin-based water-retention slow-release copper fertilizer |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106563417B (en) | A kind of Biosorbent for heavy metals and preparation method thereof | |
| CN109092265B (en) | Cellulose-based adsorbent modified by polyimidazole ionic liquid and preparation method and application thereof | |
| US9950319B2 (en) | High exchange-capacity anion exchange resin with dual functional-groups and method of synthesis thereof | |
| JP6473803B2 (en) | Extraction method of chlorogenic acid from Tochu leaves | |
| CN105080505B (en) | A kind of tangerine peel, orange peel, the method for comprehensive utilization of shaddock ped | |
| CN102527348B (en) | Lignin heavy metal ion adsorbent and preparation method thereof | |
| CN107236057B (en) | A kind of biodegrading process obtaining Dalteparin Sodium | |
| CN107266606B (en) | New process for extracting fucosan sulfate from kelp processing waste liquid | |
| CN109666155A (en) | A kind of cross-linking modified lignin chelating agent and preparation method thereof | |
| CN105859983A (en) | Modified lignin chelator and preparation method thereof | |
| CN107583613A (en) | A kind of Two New Cationic Starches ether derivant Dye Adsorption material and preparation method thereof | |
| CN115746171A (en) | Method for preparing enoxaparin sodium | |
| CN113877550A (en) | Preparation method of polymeric adsorbent for boron element in water phase | |
| CN107597076A (en) | A kind of aminocellulose and its application | |
| CN108715617A (en) | Native cellulose prepares carboxymethyl cellulose ammonium | |
| CN109320650B (en) | Preparation method of macroporous weakly-alkaline acrylic anion exchange resin | |
| CN108218948B (en) | Preparation method of sodium aescinate | |
| CN103214331A (en) | Method for removing cadmium in rice protein hydrolysate | |
| CN111655663B (en) | Methods for producing polyphenol compositions from bagasse | |
| CN104292161B (en) | A kind of process for purification along atracurium besilate | |
| CN106589405A (en) | Lignin metal ion chelating agent and preparation method thereof | |
| CN103979710B (en) | Treatment method for starch processing waste water | |
| CN106693922A (en) | Sewage substrate improver | |
| KR101753452B1 (en) | Method for preparing adsorbent from Waste fiber and adsorbent thereof | |
| CN106317284A (en) | Extraction-elution resin chelated with P507 extraction agent and preparation method and application of extraction-elution resin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190423 |
|
| RJ01 | Rejection of invention patent application after publication |