CN103881037A - Preparation method of smart material for separating indole in oil product - Google Patents
Preparation method of smart material for separating indole in oil product Download PDFInfo
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Abstract
The invention provides a preparation method of a smart material for separating indole in an oil product. The invention relates to a preparation method and application performance of a smart material on a silica gel surface, as proved by a research of simulating adsorption and separation performance of indole in the oil product, the smart material can effectively separate the indole in the oil product, and the invention belongs to the technical field of environmental pollution control chemistry. According to the preparation method provided by the invention, with silica gel as a carrier substrate, 4-vinyl pyridine (4-VP) as a functional monomer, indole as a template molecule, and ethylene glycol dimethacrylate (EGDMA) as a crosslinking agent, a novel smart material on a silica gel surface is prepared by adopting mass polymerization and surface imprinting technology. Meanwhile, the structural characteristics and adsorption properties of the material are researched, the result shows that the synthesis method of the material is feasible, the smart material provided by the invention can effectively separate the indole in the oil product, and compared with a traditional molecularly imprinted polymer, the smart material has a lager surface area, higher mechanical strength, high adsorption capacity and good selective separation property and elution recovery on the indole.
Description
Technical field
The invention belongs to environmental pollution control technical field of chemistry, relate to the performance characteristic of the indoles in a kind of preparation method and separating oil thereof of Silica Surface intelligent material, be specifically related to the preparation method of the intelligent material of indoles in a kind of separating oil.
Background technology
In petroleum products, the existence of nitrogen has all brought very large harm to the quality refining and oil product of the use of engine, environment, oil product.Nitride can participate in the reaction that strikes a bargain, larger on the stability impact of oil product; Nitrogenous compound in gasoline, diesel oil can generate nitrogen oxide NOx, wherein nitrogen peroxide (NO most importantly after burning
2).NO
2being the main source of pollution of atmospheric environment, is the immediate cause that forms photo-chemical smog and acid rain.Thereby develop ultralow nitrogen or become a very urgent research topic without nitrogen oil fuel.
Nitride in oil is divided into two classes, i.e. basic nitrogen compound and non basic nitrogen compound.So-called basic nitrogen compound, refers to the nitrogenate that can react with perchloric acid in glacial acetic acid solution.The basic nitrogen compound that has at present separated and identified mainly contains pyridine, quinoline, isoquinoline 99.9, naphthazin(e), aza-phenanthrenes etc. and homologue thereof.Non basic nitrogen compound is mainly pyrroles, indoles, carbazole etc. and homologue thereof, also has in addition important non basic nitrogen compound---the metal porphyrins of a class, and it mainly concentrates in residual oil.Wherein basic nitrogen can be deviate from by modes such as acid extractions, the strategy that non basic nitrogen will adopt two steps to walk.At present, the denitride technology of comparative maturity has hydrodenitrification technology, oxidation process denitrification technology, extraction denitride technology, complexing denitride technology, absorption denitride technology etc. both at home and abroad.Hydrodenitrification technology is a kind of denitrogenation method of widespread use in world wide.But, the reaction conditions of hydrodenitrification technical requirements high temperature, high pressure, and expend a large amount of hydrogen, producing ultralow nitrogen oil product can make denitrogenation cost sharply increase, be difficult to economically bear, and acid extraction denitride technology is difficult to non basic nitrogen effectively to be deviate from, so new denitride technology is devoted to develop in countries in the world.New denitride technology mainly contains oxidation process denitrification technology, absorption denitride technology bio-denitrification technology etc.Wherein, absorption denitride technology so that its denitrification effect is good, operational condition is gentle, facility investment and process cost is low, alkene in light gasoline fraction is not become domestic and international study hotspot by advantages such as octane value, sorbent material saturated, that do not reduce gasoline are renewable, low in the pollution of the environment.Can absorption denitride technology become countries in the world from now on and produce one of major technique of ultralow nitrogen clear gusoline, key be to find a kind of efficient, cheap, selectivity is high and can keep the sorbent systems in certain bed life-span, sorbent material just can meet the requirement of industrial design like this.If reach 1 year the work-ing life of sorbent material, the economic benefit of adsorbing denitrogenation is quite attracting.The advantages such as surface molecular printed material material has that loading capacity is high, selectivity good, reusable, efficient, high-absorbility, low-cost sorbent material.
Summary of the invention
The present invention proposes a kind of preparation method of Silica Surface intelligent material, this material has highly selective, high-adsorption-capacity, long service life, low cost and other advantages to indoles, thereby reaches the object of organonitrogen in deep removal oil product.
The present invention is using silica gel as carrier, taking 4-vinylpridine (4-VP) as function monomer, indoles is template molecule, and ethylene glycol dimethacrylate (EGDMA) is linking agent, the different dibutyronitrile of azo (AIBN), as initiator, has synthesized Silica Surface intelligent material.
The technical solution used in the present invention is:
(1) MPS modifies Silica Surface:
First silica gel is soaked in hydrochloric acid soln and stir and make silica gel activating, then filter, be washed with distilled water to neutrality, be placed in vacuum drying oven and dry, then the silica gel after obtained activation is joined in toluene solution, then the γ adding wherein-(methacryloxypropyl) propyl trimethoxy silicane (MPS), heating is also constantly stirred, after the material obtaining is washed with toluene, methyl alcohol and ethanol successively, in vacuum drying oven, dry, obtain the silica gel that MPS modifies.
Wherein, the concentration of described hydrochloric acid soln is 10% ~ 20%; Silica gel after described activation and the ratio of toluene solution are 1-2g:40-60mL, and the volume ratio of wherein γ-(methacryloxypropyl) propyl trimethoxy silicane and toluene solution is: 3-5:40-60; The described 90-114 DEG C that is heated to.
(2) Silica Surface molecular imprinting layer is coated:
Silica gel, indoles and the 4-vinylpridine (4-VP) that take MPS modified are dissolved in chloroform.At room temperature stir, make the prepolymerization in mixed solution of template molecule and function monomer, make pre-assembled solution.
Wherein, the ratio of the silica gel of described MPS modified, indoles and vinyl pyridine is 1-2g:0.036-0.047g:0.12mL-0.018mL; The ratio of the silica gel of described chloroform and MPS modified is: 20-40mL:1-2g.
(3) wash-out of template molecule indoles and the generation of recognition site:
Linking agent ethylene glycol dimethacrylate (EGDMA) and the different dibutyronitrile of initiator azo (AIBN) are joined in the described mixing solutions of step (2), and ultrasonic dispersion in nitrogen environment then continues to stir in constant temperature oil bath.The polymkeric substance obtaining, successively with drying in vacuum drying oven after toluene, methyl alcohol and washing with alcohol, is made to intelligent sorbing material.
The ratio of the different dibutyronitrile of ethylene glycol dimethacrylate, azo adding wherein, and the silica gel of MPS modified is: 1.2 mL:0.01 g ~ 0.03, mL ~ 1.6 g:1-2g; Described constant temperature oil bath temperature is 65 DEG C.
(4) removal of template molecule indoles in intelligent material:
In intelligent material, the removal of template molecule indoles is to have extracted by Soxhlet, polymer template molecule is carried out to wash-out with the mixing solutions of methyl alcohol and acetic acid, and after vacuum drying oven inner drying, makes the intelligent material of indoles in specific adsorption oil product.
Wherein, the volume ratio of described methyl alcohol and acetic acid is 9:1.
Beneficial effect:
The present invention has synthesized novel silica gel surface intelligent material, and it is large that this intelligent material combines specific surface area, the advantage that mass transfer velocity is fast, and there is again the advantage of predetermined selectivity the while.Taking four vinyl pyridines (4-VP) as function monomer, indoles is template molecule, ethylene glycol dimethacrylate (EGDMA) is linking agent, the silica gel that γ-(methacryloxypropyl) propyl trimethoxy silicane (MPS) carries out finishing is as carrier matrix, the synthetic novel intelligent material that indoles is had to a specific selectivity has greatly reduced the phenomenon of functional group " embedding ", has improved mass transfer velocity and the adsorptive power of intelligent material.Investigated absorption property and the reusing of this intelligent material to the indoles in oil product, it is restorative that result shows that this intelligent material has larger loading capacity, better adsorption selectivity and good wash-out to indoles simultaneously.In sum, the synthetic novel intelligent material of present method, compared with traditional imprinted material, has physical strength high, has greatly reduced the phenomenon of functional group " embedding ", has improved mass transfer velocity, has increased adsorptive power and the selectivity of intelligent material.
Brief description of the drawings
Fig. 1 is the infared spectrum figure for preparing material, and wherein: a is activated silica gel, b is MPS finishing silica gel, and c is trace intelligent material, and d is non-marking material.
Fig. 2 is the kinetics of adsorption analytical results of prepared material.
Fig. 3 is the adsorption isothermal line diagram of prepared material.
Fig. 4 is the selection competitive analysis result of prepared material.
Fig. 5 is the absorption regeneration analytical results of prepared material.
Embodiment
In conjunction with lower mask body embodiment, the present invention will be further described.
embodiment 1:
Have specific adsorption Indole Molecular intelligent material preparation in three steps: MPS to Silica Surface modify, coated, the wash-out of template molecule indoles and the generation of recognition site of Silica Surface molecular imprinting layer.
Preferred version: first by silica gel with soaking in 10% HCl and stirring 24 h, then filter, be washed with distilled water to neutrality (being that pH value is 7), be placed in 60 DEG C of vacuum drying ovens and dry 24 h.Then the silica gel after 1 obtained g activation is joined in the toluene solution of 60 mL, add wherein again γ-(methacryloxypropyl) propyl trimethoxy silicane (MPS) of 5 mL, being heated to 114 DEG C constantly stirs after 24 h, after the material obtaining is once washed with toluene, methyl alcohol and ethanol, in the vacuum drying oven of 60 DEG C, dry 24 h.Accurately take the silica gel of 1 g MPS modified, the 4-VP of the indoles of 0.047 g and 0.18 mL is dissolved in the chloroform of 40 mL.At room temperature stir 6 h, make the prepolymerization in mixed solution of template molecule and function monomer.Then the initiator A IBN of the linking agent EGDMA of 1.6 mL and 0.03 g is joined in mixing solutions, ultrasonic 15 min in nitrogen environment then continue to stir 24 h in 65 DEG C of constant temperature oil baths.The polymkeric substance obtaining is used toluene, methyl alcohol and washing with alcohol post-drying successively.Finally use methyl alcohol/acetic acid (90/10, v/v) mixing solutions to carry out wash-out 72 h to polymer template molecule, and in vacuum drying oven 60 DEG C of dry 24 h.
embodiment 2:
First by silica gel with soaking in 15% HCl and stirring 24 h, then filter, be washed with distilled water to neutrality (being that pH value is 7), be placed in 60 DEG C of vacuum drying ovens and dry 24 h.Then the silica gel after 1.5 obtained g activation is joined in the toluene solution of 40 mL, add wherein again γ-(methacryloxypropyl) propyl trimethoxy silicane (MPS) of 3 mL, being heated to 110 DEG C constantly stirs after 24 h, after the material obtaining is once washed with toluene, methyl alcohol and ethanol, in the vacuum drying oven of 60 DEG C, dry 24 h.Accurately take the silica gel of 1.5 g MPS modifieds, the 4-VP of the indoles of 0.36 g and 0.12 mL is dissolved in the chloroform of 20 mL.At room temperature stir 7 h, make the prepolymerization in mixed solution of template molecule and function monomer.Then the initiator A IBN of the linking agent EGDMA of 1.5 mL and 0.02 g is joined in mixing solutions, ultrasonic 15 min in nitrogen environment then continue to stir 24 h in 65 DEG C of constant temperature oil baths.The polymkeric substance obtaining is used toluene, methyl alcohol and washing with alcohol post-drying successively.Finally use methyl alcohol/acetic acid (90/10, v/v) mixing solutions to carry out wash-out 72 h to polymer template molecule, and in vacuum drying oven 60 DEG C of dry 24 h.
embodiment 3:
First by silica gel with soaking in 20% HCl and stirring 24 h, then filter, be washed with distilled water to neutrality (being that pH value is 7), be placed in 60 DEG C of vacuum drying ovens and dry 24 h.Then the silica gel after 2 obtained g activation is joined in the toluene solution of 50 mL, add wherein again γ-(methacryloxypropyl) propyl trimethoxy silicane (MPS) of 4 mL, being heated to 114 DEG C constantly stirs after 24 h, after the material obtaining is once washed with toluene, methyl alcohol and ethanol, in the vacuum drying oven of 60 DEG C, dry 24 h.Accurately take the silica gel of 2 g MPS modifieds, the 4-VP of the indoles of 0.040 g and 0.15 mL is dissolved in the chloroform of 30 mL.At room temperature stir 8 h, make the prepolymerization in mixed solution of template molecule and function monomer.Then the initiator A IBN of the linking agent EGDMA of 1.2 mL and 0.01 g is joined in mixing solutions, ultrasonic 15 min in nitrogen environment then continue to stir 24 h in 65 DEG C of constant temperature oil baths.The polymkeric substance obtaining is used toluene, methyl alcohol and washing with alcohol post-drying successively.Finally use methyl alcohol/acetic acid (90/10, v/v) mixing solutions to carry out wash-out 72 h to polymer template molecule, and in vacuum drying oven 60 DEG C of dry 24 h.
Below to adopt embodiment 1(preferred version) effect of the intelligent material for preparing:
1. the sign of intelligent material
To the silica gel after modifying and synthetic intelligent material capable infrared scan (Fig. 1) analyze.
As shown in Figure 1, in spectral line a, H-O charateristic avsorption band is presented at 3448 cm to Infrared Characterization
1place, illustrates that silica gel is successfully activated, and Silica Surface has been introduced to a large amount of oh groups.At 2978 cm
1chu Wei – CH
2-,, – CH
3-and the flexible absorption peak of C=O.This show MPS by grafting successfully the Silica Surface in activation, thereby introduced a large amount of two keys at Silica Surface.In spectral line c, C=N vibration absorption peak is presented at 1640 cm
– 1, 1455 cm
– 1chu Wei – CH
2– CH
2the charateristic avsorption band of –.The appearance of these absorption peaks has illustrated that 4VP and EDGMA are successfully wrapped in Silica Surface.Spectral line d is the charateristic avsorption band spectrum of non-marking material, similar to the absorption peak of intelligent material, therefore pattern of descriptive parts molecule is successfully removed.
2. kinetics of adsorption analysis
The consumption of fixing intelligent material is 10 mg, and 6 mL starting point concentrations are 500 mg L
-1indoles solution, between 25-45 DEG C of temperature range, investigate the kinetics of adsorption of intelligent material to indoles, be respectively 10 min, 20min, 30min by the contact reacts time changing between sorbent material and adsorbate, 40min, 60min, 90min, 120min, 150min, 180min assesses the impact of the adsorption rate of intelligent material on indoles.Result as shown in Figure 2, start 30min in, intelligent material is quite fast to the adsorption rate of indoles, shows that indoles is easy to enter the VOID POSITIONS of polymer materials; Subsequently adsorptive capacity gradually increasing amount reduce and reach equilibrium stage, the time that reaches balance is approximately 40min.In the time of 25 DEG C, this intelligent material is 45.74 mg g to the maximum to the equilibrium adsorption capacity of indoles
-1.It has larger adsorptive capacity to Indole Molecular is due to the hydrogen bond action between superpolymer and Indole Molecular, and this large amount of pore structure in intelligent material surface provides and more binding site.
In order further to study the kinetics of adsorption of this intelligent material to Indole Molecular, pseudo-first-order kinetics equation (1) and accurate second-order kinetic equation formula (2) and standard deviation (3) application are as follows:
Here q
eand q
tloading capacity while representing respectively equilibrium adsorption capacity and time t, and k
1(min
– 1) and k
2(g mg
-1min
-1) be respectively pseudo-first-order and the accurate secondary rate constant of kinetics of adsorption.K
1by drawing log (q
e– q
t) graphic representation of t is calculated to k
2by drawing t/q
tgraphic representation to t calculates.Represent standard deviation, and be respectively adsorption experiment value and calculated value, N is the number of data point in experiment.
Relation conefficient (the R that has obtained providing in table 1 by calculating us
2) and [Δ q (%)].Relatively these values, we find that accurate second-order kinetics model-fitting has gone out higher relation conefficient.Therefore, this intelligent material more accords with second-order kinetics model to the absorption behavior of Indole Molecular and confirms that this adsorption process is a chemisorption process.
pseudo-first-order kinetic model and the accurate second-order kinetics model parameter of table 1 intelligent material to indoles absorption
3. determining of adsorption isothermal line
According to experimental technique, this intelligent material of point another name 10mg, in a series of 10 mL band plug bottles, adds respectively concentration to be respectively 100 – 800 mg L
-1indoles solution, between 25-45 DEG C of temperature range, carry out the adsorption experiment of 3 h, detect the equilibrium concentration of indoles solution by high resolution gas chromatography method, and calculate its loading capacity, draw adsorption isothermal curve, its result as shown in Figure 3, the loading capacity of this intelligent material increases along with the rising of indoles strength of solution, and temperature gets over high-adsorption-capacity and decline on the contrary, equilibrium adsorption behavior can be calculated and be obtained by Langmuir adsorption isotherm equation (4) and Freundlich adsorption isotherm equation (5) respectively:
C
e/q
e = C
e/q
m + 1/(q
mK
L) (4)
lnq
e = lnC
e/n + lnK
F (5)
Wherein q
e(mg g
-1) and C
e(mg l
-1) be to be respectively the concentration of indoles in the loading capacity of indole-MIPs and balanced solution, q
m(mg g
-1) be the calculated value of loading capacity on individual layer, K
d(mg l
-1) be Langmuir constant (relevant to the avidity of adsorption site), K
fbe all Freundlich constant and shown respectively adsorptive power and adsorption strength with n.K
fwith n can be from logq
eto logC
elinear relationship calculate.
Adopt Langmuir and Freundlich adsorption isotherm line model to carry out matching to adsorpting data, its fitting result is shown in table 2.Freundlich equation has used in the adsorption process of non-covalent material, and Langmuir equation is used to describe the monolayer adsorption between adsorptive and adsorbate.Can find out from fitting result, this intelligent material more meets Langmuir Isothermal Model to the adsorption process of indoles, has illustrated that the binding site on synthetic intelligent material is limited.Meanwhile, as can be seen from Figure 3 adsorptive capacity reduces with the rising of temperature, this be due to the bonding force of hydrogen bond when the higher temperature a little less than, so suitable cooling contributes to the absorption of intelligent material to indoles.
table 2 Langmuir adsorption isotherm equation and Freundlich adsorption isotherm equation model parameter
4. the impact of temperature on Adsorption thermodynamics parameter
In order to investigate the impact of temperature on Adsorption thermodynamics parameter, standard free energy Δ G °, S ° of H ° of standard enthalpy change Δ and standard entropy change Δ calculate by following equation (6) and (7):
lnK
c = –ΔH°/RT + ΔS°/R (6)
ΔG° = RTlnK
c (7)
Wherein
k c the equilibrium constant, can pass through (
c p / C s ) calculate.
c p represent the equilibrium adsorption capacity of indole-MIPs to indoles,
c s it is the equilibrium concentration of indoles in solution.Thermodynamical coordinate is as shown in table 3.G ° of negative value Δ confirmed that adsorption process is a spontaneous process.In addition, negative value Δ H ° has represented that adsorption process is an exothermic process.
the Adsorption thermodynamics parameter of table 3 intelligent material to indoles
5. the selectivity of intelligent material
(sorbent material consumption is 10 mg, adds 6 mL concentration to be 500 mg L under the same conditions
-1mixing solutions, shake 3.0 at 25 DEG C and h) investigate intelligent material and the absorption of non-imprinted material to indoles and its analog 3-skatole, quinoline and BT, the results are shown in Figure 4.As we can see from the figure intelligent material to the absorption of indoles higher than other analog, also the absorption to indoles higher than non-printed material material, even this explanation other analogs disturb around under, this intelligent material still has higher specific recognition capability to indoles.
6. the reusing of intelligent material
The intelligent material of our synthesized is carried out to adsorption/desorption replica test ten times, and the adsorptive power of ten round-robin tests of intelligent material is shown in Fig. 5.As shown in Figure 5, after ten adsorption and desorption tests, adsorptive power has a little to decline, and is 86% of initial adsorption ability.This illustrates that this intelligent material has good wash-out reproducibility, and in elution process, a little pore structure is destroyed simultaneously.
Claims (6)
1. a preparation method for the intelligent material of indoles in separating oil, is characterized in that, carries out according to following steps:
(1) MPS modifies Silica Surface:
First silica gel is soaked in hydrochloric acid soln and stir and make silica gel activating, then filter, be washed with distilled water to neutrality, be placed in vacuum drying oven and dry, then the silica gel after obtained activation is joined in toluene solution, γ-(methacryloxypropyl) propyl trimethoxy silicane adding wherein again, heating is also constantly stirred, after the material obtaining is washed with toluene, methyl alcohol and ethanol successively, in vacuum drying oven, dry, obtain the silica gel that γ-(methacryloxypropyl) propyl trimethoxy silicane is modified;
(2) Silica Surface molecular imprinting layer is coated:
The silica gel, indoles and the 4-vinylpridine that take γ-(methacryloxypropyl) propyl trimethoxy silicane modified are dissolved in chloroform; At room temperature stir, make the prepolymerization in mixed solution of template molecule and function monomer, make pre-assembled solution;
(3) wash-out of template molecule indoles and the generation of recognition site:
Linking agent ethylene glycol dimethacrylate and the different dibutyronitrile of initiator azo are joined in the mixing solutions of step (2) gained, and ultrasonic dispersion in nitrogen environment then continues to stir in constant temperature oil bath; The polymkeric substance obtaining, successively with drying in vacuum drying oven after toluene, methyl alcohol and washing with alcohol, is made to intelligent sorbing material;
(4) removal of template molecule indoles in intelligent material:
In intelligent material, the removal of template molecule indoles is to have extracted by Soxhlet, polymer template molecule is carried out to wash-out with the mixing solutions of methyl alcohol and acetic acid, and after vacuum drying oven inner drying, make the Silica Surface intelligent material of indoles in specific adsorption oil product.
2. the preparation method of the intelligent material of indoles in a kind of separating oil according to claim 1, is characterized in that, described in step (1), the concentration of hydrochloric acid soln is 10% ~ 20%; Silica gel after described activation and the ratio of toluene solution are 1-2g:40-60mL, and the volume ratio of wherein γ-(methacryloxypropyl) propyl trimethoxy silicane and toluene solution is: 3-5:40-60; The described 90-114 DEG C that is heated to.
3. the preparation method of the intelligent material of indoles in a kind of separating oil according to claim 1, it is characterized in that, the ratio of silica gel, indoles and the vinyl pyridine of γ described in step (2)-(methacryloxypropyl) propyl trimethoxy silicane modified is 1-2g:0.036-0.047g:0.12mL-0.018mL; The ratio of the silica gel of described chloroform and γ-(methacryloxypropyl) propyl trimethoxy silicane modified is: 20-40mL:1-2g.
4. the preparation method of the intelligent material of indoles in a kind of separating oil according to claim 1, it is characterized in that, the ratio of the silica gel of the different dibutyronitrile of ethylene glycol dimethacrylate, azo adding described in step (3) and γ-(methacryloxypropyl) propyl trimethoxy silicane modified is: 1.2 mL:0.01 g ~ 0.03, mL ~ 1.6 g:1-2g; Described constant temperature oil bath temperature is 65 DEG C.
5. the preparation method of the intelligent material of indoles in a kind of separating oil according to claim 1, is characterized in that, the volume ratio of the described methyl alcohol of step (4) and acetic acid is 9:1.
6. the preparation method of the intelligent material of indoles in a kind of separating oil according to claim 1, is characterized in that, prepared Silica Surface intelligent material is for specific adsorption oil product indoles.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105457600A (en) * | 2015-11-26 | 2016-04-06 | 王金明 | Method for preparing denitrifying adsorbent |
| US10828322B1 (en) | 2019-11-29 | 2020-11-10 | Claves Life Sciences Limited | Molecularly imprinted polymers for sequestering acetate and other molecules |
| CN115678606A (en) * | 2022-09-30 | 2023-02-03 | 中国石油大学(北京) | High-value utilization method of sulfur-containing nitrogen-containing pyrolysis diesel oil |
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| CN102702565A (en) * | 2012-06-12 | 2012-10-03 | 福州大学 | Preparation method and application of indole acetic acid (IAA) molecularly imprinted polymer (MIP) |
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| CN102702565A (en) * | 2012-06-12 | 2012-10-03 | 福州大学 | Preparation method and application of indole acetic acid (IAA) molecularly imprinted polymer (MIP) |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105457600A (en) * | 2015-11-26 | 2016-04-06 | 王金明 | Method for preparing denitrifying adsorbent |
| US10828322B1 (en) | 2019-11-29 | 2020-11-10 | Claves Life Sciences Limited | Molecularly imprinted polymers for sequestering acetate and other molecules |
| US10940459B1 (en) | 2019-11-29 | 2021-03-09 | Claves Life Sciences Limited | Molecularly imprinted polymers for sequestering acetate and other molecules |
| CN115678606A (en) * | 2022-09-30 | 2023-02-03 | 中国石油大学(北京) | High-value utilization method of sulfur-containing nitrogen-containing pyrolysis diesel oil |
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