CN106311327B - A kind of preparation method of the convertible selective polyalcohol catalyst of silver load - Google Patents
A kind of preparation method of the convertible selective polyalcohol catalyst of silver load Download PDFInfo
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- CN106311327B CN106311327B CN201610591864.4A CN201610591864A CN106311327B CN 106311327 B CN106311327 B CN 106311327B CN 201610591864 A CN201610591864 A CN 201610591864A CN 106311327 B CN106311327 B CN 106311327B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/063—Polymers comprising a characteristic microstructure
- B01J31/067—Molecularly imprinted polymers
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/063—Polymers comprising a characteristic microstructure
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
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Abstract
The present invention provides a kind of preparation method of the convertible selective polyalcohol catalyst of silver load.Function monomer used in the preparation method is the binary copolymerization function monomer system for constructing polymer molecule identification framework and movable function base side chain structure.Substrate and active component silver presoma are first dissolved in dimethyl sulfoxide and are complexed by this method, add function monomer, crosslinking agent and initiator, and nitrogen deoxidation is then led into solution, and sealing is placed on irradiation under ultraviolet lamp and causes polymerization, form catalyst precursor.Ag ion is through sodium borohydride reduction in catalyst precursor, products therefrom is after water, ethyl alcohol clean the substrate molecule of removing trace repeatedly, vacuum drying, the convertible selective polyalcohol catalyst of silver load is obtained, and the raw materials of industry such as isomer mixture that can be used for nitrobenzyl alcohol directly prepare p-aminophenyl methanol.The features such as simple, raw material is easy to get, is easy to operate the preparation method with technical principle, easily prepared.
Description
Technical field
The invention belongs to technical field of polymer materials, and in particular to a kind of convertible selective polymer of silver load
The preparation method of catalyst.
Background technique
Catalysis is the foundation stone of modern chemical industry, realizes that controllable, modulated catalytic action is that current industry is badly in need of solution
Great matter of science and technology certainly.Poly-N-isopropyl acrylamide (PNIPAm) with metal nanoparticle load is the poly- of representative
The development of mixture catalyst preparation method creates condition for the realization of this target.The reason is that polyalcohol catalyst
It is unique critical that hydrophilic amide base-hydrophobicity isopropyl design feature of middle PNIPAm forms it in an aqueous medium
Solution temperature (~32 DEG C).When being lower than critical-temperature, in polyalcohol catalyst in PNIPAm amide groups and aqueous media hydrogen
Key interaction promotes its dissolution in water, so that substrate be made to obtain the channel towards metal nanoparticle, catalysis is made
With being " on "；Conversely, when being higher than critical-temperature, hydrophilic amide base-hydrophobicity isopropyl phase in polyalcohol catalyst
Balance is broken, hydrophobic effect will play conclusive role, and polymer becomes insoluble in.At this point, water has become polymerization
The not good solvent of object is discharged from inside rapidly, causes substrate to lead to " blocking " of metallic nanoparticle subchannel, to make to be catalyzed
Effect obtains " closing ".By it is this it is unique in a manner of, metal nanoparticle load PNIPAm polyalcohol catalyst preparation
Method makes chemical reaction process obtain transition or " freezing " immediately by the temperature-sensitive phase transformation of carrier material critical temperature condition,
Preset position is skipped or rests on, to realize modulated catalytic action process
However, in practical applications, most catalytic action processes are related to being not a kind of simple chemical action process, lead to
Often it is related to multi-component reaction object and multistep catalytic action process, such as the isomer mixture raw material of industry of nitrobenzyl alcohol is direct
P-aminophenyl methanol etc. is prepared, catalysis reaction process need to be often controlled, needs to carry out selective control according to actual needs, that is, fills and exist perhaps
Selective catalysis effect is carried out in particular step, and other steps are then Conventional catalytic effect, to reduce the influence of side reaction.So
And based on existing using the PNIPAm of metal nanoparticle load as the preparation method of the polyalcohol catalyst of representative, people are only capable of
The control for realizing catalytic activity, and cannot achieve the preparation that selectively variable changes polyalcohol catalyst, and domestic and foreign literature and specially
Benefit is without related technology reports, so that people be forced to develop the new technology of polyalcohol catalyst preparation, new method.
Be directly realized by the preparation that selectively variable changes polyalcohol catalyst, must fundamentally solve substrate selectivity and
The key technology of modulation property.Knowledge is derived from naturally, derived from the understanding and cognition to natural phenomena.After natural choosing in 1 years
It selects and evolves, natural biology and bio-tissue are made as this target to the immunology index of exotic and its with the compatible of environment
Realization create condition.Bio-tissue such as antibody etc. can identify specific exotic with high specificity, resist mechanism generation
The ability of exotic infringement, to generate immunization process.The type of antibody and composition are varied as far as possible, but resist on the whole
The structure of body molecule can be divided into constant region and variable region two parts.Wherein, constant region has metastable amino acid sequence, certainly
Determine the overall architecture of antibody molecule.In contrast, with the amino acid residue of sequence mutability, decision and antigen binding in variable region
Specificity.Biological environment of change such as temperature, pH, electrolyte etc. will cause variable region acute variation, cause its with it is external
The variation that object specifically interacts, in and/or destroy exotic toxin, to authorize natural biology to the immunologic mechanism of exotic
And its compatibility with environment.Although the immunology index of natural biology and its be its nature with environmental compatible mechanism, with catalysis
Agent exploitation is unrelated, but its partitioned organization is paved the way for the realization of selectivity and modulation property, new for polyalcohol catalyst preparation
The formation of technology, new method lays the foundation.
Summary of the invention
The purpose of the present invention is be directed to current industry great matter of science and technology urgently to be solved, provide it is a kind of silver load
The preparation method of convertible selective polyalcohol catalyst.Exotic is immunized this method introducing natural biology and its and environment
Compatible concept constructs two functions of polyalcohol catalyst --- polymerization is constructed with man-made antibody's technology i.e. molecular imprinting technology
The overall architecture of object molecular recognition, with movable function base side chain building can modulation specificity interaction, pass through temperature
Variation induces the variation of specificity interaction, to realize the preparation of convertible selective polyalcohol catalyst.The preparation
Monomer used by method and active component silver presoma are common monomer and ionic compound, and there is raw material to be easy to get, draw materials
The features such as convenience, principle are simple, easily prepared.
The present invention provides a kind of preparation methods of the convertible selective polyalcohol catalyst of silver load, according to following
Method carries out: substrate to be measured (i.e. template molecule) and active component silver presoma is first dissolved in dimethyl sulfoxide and is complexed, then
Function monomer, crosslinking agent and initiator is added, nitrogen deoxidation is then led into solution, sealing, which is placed on to irradiate under ultraviolet lamp, to be caused
Polymerization forms catalyst precursor.For Ag ion through sodium borohydride reduction, products therefrom is anti-through water, ethyl alcohol in catalyst precursor
After the substrate molecule of multiple cleaning removing trace, vacuum drying to get under highly selective, high temperature in a low temperature of silver load without selection
The polyalcohol catalyst of property.
The substrate to be measured is nitro compound, including p nitrobenzyl alcohol or nitro alcohol.
The active component silver presoma is silver iron compound, specially silver nitrate.
The function monomer is the binary copolymerization for constructing polymer molecule identification framework and movable function base side chain structure
Function monomer system, including contain long-chain functional group monomer and without chain monomer, wherein long-chain functional group monomer and without chain list
The molar ratio of both bodies is 1:4~8；
The long-chain functional group monomer is 10-HAD, 2- nonenoic acid or octadecenic acid；The no chain list
Body is acrylic acid；
The crosslinking agent is that there are two the polymerisable monomers of activity double key for tool, is N, N- methylene-bisacrylamide.
The initiator is that can carry out light-initiated initiator, is azodiisobutyronitrile.
The time of the logical nitrogen deoxidation is 5-10 minutes, ultraviolet lamp irradiation time is 20-30 hours.
The dosage of the dimethyl sulfoxide with can be completely dissolved substrate, active constituent silver presoma, function monomer, crosslinking agent and
Subject to initiator；
The molar ratio of the substrate to be measured and active component silver presoma dosage is less than or equal to Ag ion coordination number 2；
Dosage of crosslinking agent is the 10~15% of function monomer integral molar quantity；
Initiator amount be subject to can initiated polymerization, be function monomer gross mass 1~5%.
The present invention caters to current industry great matter of science and technology urgently to be solved, the silver-colored load aggregation object catalyst of preparation
The preparation of the raw materials of industry such as the isomer mixture that can be directly realized by the catalytic action selectively converted, and can be used for nitrobenzyl alcohol
P-aminophenyl methanol, has the following prominent advantages:
(1) compared with the preparation of the PNIPAm polyalcohol catalyst of conventional metals nanometer particle load, the present invention is constructed
The molecular recognition framework and molecular structure of polyalcohol catalyst realize what selectively variable changed with two functions such as temperature changes
Catalytic action ability；
(2) common man-made antibody is loaded with metal nanoparticle --- compared with the preparation of molecularly imprinted polymer catalyst,
Present invention introduces natural biologies to the Concept of Immunity of exotic, induces the variation specifically to interact by the variation of temperature, awards
Give synthetic polymer catalyst choice ability temperature controlled.
(3) the technology of the present invention principle is simple, easy to operate, easily prepared, and required equipment requirement is not high, it is easy to accomplish big rule
Mould industrialized production.
Detailed description of the invention
Fig. 1 is the technical principle of silver load aggregation object catalyst prepared by the embodiment of the present invention 1.
Fig. 2 is the FT-IR spectrum of silver load aggregation object catalyst prepared by the embodiment of the present invention 1.
Fig. 3 is the XRD spectrum of silver load aggregation object catalyst prepared by the embodiment of the present invention 1.
Fig. 4 is the TEM photo of silver load aggregation object catalyst prepared by the embodiment of the present invention 1.
Fig. 5 is the substrate dynamic desorption volt-ampere DCV figure of silver load aggregation object catalyst prepared by the embodiment of the present invention 1
Fig. 6 is the dynamic light scattering DLS transformation curve of silver load aggregation object catalyst prepared by the embodiment of the present invention 1.
Fig. 7 is the convertible selective catalysis effect of silver load aggregation object catalyst prepared by the embodiment of the present invention 1, A-25
DEG C, B-50 DEG C.
Fig. 8 is the convertible selective catalysis effect of silver load aggregation object catalyst prepared by the embodiment of the present invention 2, A-30
DEG C, B-45 DEG C.
Fig. 9 is the convertible selective catalysis effect of silver load aggregation object catalyst prepared by the embodiment of the present invention 3, A-28
DEG C, B-40 DEG C.
Figure 10 is the convertible selective catalysis effect of load aggregation object catalyst prepared by the embodiment of the present invention 4, A-25
DEG C, B-50 DEG C.
Specific embodiment
It is for a more detailed description to the present invention with embodiment below.These embodiments are only best mode for carrying out the invention
Description, rather than the limitative examples of the scope of the invention.Without departing substantially from substantive content of the present invention, that makes is aobvious and easy
The replacement or improvement seen belong to the range of embodiment of the present invention description.
Embodiment 1:
The technical principle of polyalcohol catalyst preparation is shown in Fig. 1, constructs two kinds of different function of polymer i.e. molecular recognition framework
And binary function monomer system used in movable function base side chain structure is the 10-HAD and propylene of molar ratio 1:4
Acid.Substrate p nitrobenzyl alcohol (4mmol) and silver-colored presoma silver nitrate (2mmol) are first dissolved in 20mL dimethyl sulfoxide and carry out network
Conjunction forms template molecule, and function monomer 10-HAD (6mmol) and acrylic acid (24mmol), crosslinking agent N, N is added
Methylene-bisacrylamide (3mmol) and initiator azodiisobutyronitrile (0.1g) then lead to (8 points of nitrogen deoxidation into solution
Clock), sealing is placed on irradiation under ultraviolet lamp and causes polymerization (24 hours), forms catalyst precursor.Ag in catalyst precursor
Ion is restored through excess sodium borohydrate (20mmol), and products therefrom cleans the p-nitrophenyl first of removing trace through water, ethyl alcohol repeatedly
After alcohol, it is dried in vacuo and (is labeled as " AgPR-ST ", wherein Ag to get the convertible selective polyalcohol catalyst to silver load
It is polyalcohol catalyst for Nano silver grain, PR, the specificity interaction that S is modulation property, T is substrate).
For the sake of comparison, prominent two functions such as modulation property and molecule distinguishability, the present embodiment is under similarity condition
Also reference polymer catalyst AgPR-S, AgPR-T and PR-ST are prepared for.Wherein, AgPR-S is the non-choosing with modulation property
Selecting property polyalcohol catalyst is prepared in addition to not having the trace using substrate, remaining is identical as preparing for AgPR-ST；AgPR-T
For can not modulation selective polymerisation object catalyst, preparation is except using in addition to long-chain function base monomer, remaining and AgPR-ST phase
Together；PR-ST is the polymer support of AgPR-ST, is prepared that using silver-colored presoma, remaining is not identical in AgPR-ST.
FT-IR spectrum, XRD spectrum and the TEM photo of these types of catalyst is set forth in Fig. 2, Fig. 3 and Fig. 4, to its group
It is characterized at, structure and form, shows that AgPR-ST catalyst obtained is composition designed by the present invention, structure and shape
State, wherein the Nano silver grain of the size containing 10-15nm.
It prepares catalyst to measure the molecule distinguishability of substrate by the desorption of catalyst surface immunoabsorbent substrate, passes through substrate
The current potential size of volt-ampere DCV figure is desorbed in dynamic, obtains catalyst to the affinity (bottom 10mg Catalyst Adsorption about 1nmol of substrate
Object；Supporting electrolyte: concentration is the KCl of 0.01mmol/mL；10mL).By comparison, the introducing pair of bionical immunology index is obtained
The influence of catalyst and substrate interaction, the result is shown in Fig. 5.Bionical immunologic mechanism introduces and (contains molecular recognition function) and is poly-
Mixture catalyst AgPR-ST, PR-ST and AgPR-T are rendered obvious by out compared with the higher affinity of AgPR-S for being free of molecular recognition function
Power shows that the AgPR-ST of preparation is the catalyst with molecule distinguishability designed by the present invention.
The modulation property for preparing catalyst is measured by dynamic light scattering DLS.The polymerization for including by comparing long-chain function base
Object catalyst and the polyalcohol catalyst for being free of long-chain function base obtain long-chain function base to preparing the temperature sensitive transformation behavior of catalyst
Influence (determination condition: 10mg catalyst is scattered in 10mL aqueous media), the result is shown in Fig. 6.Long-chain function base introduce to
The preparation of AgPR-ST catalyst, is granted by AgPR-ST Thermo-sensitive transformation ability, and transition point appears in about 40 DEG C.
The selectivity of catalyst can modulation catalytic action: based on the measurement to polyalcohol catalyst modulation property, selecting respectively
It selects 25 DEG C and 50 DEG C above and below transition point and compares measurement.Catalytic performance test uses following system: with specificity
Substrate p nitrobenzyl alcohol and the like nitro alcohol is reduced to probe reaction, is by 1.5mL concentration of substrate
The solution of 0.2mmol/mL is added in the sodium borohydride aqueous solution that 1.5mL concentration is 2.0mmol/mL.The present embodiment is made
The AgPR-ST and reference catalyst obtained is added on above-mentioned system respectively, makes the concentration 0.05mg/mL of catalyst, is measured,
As a result see Fig. 7 (PR-ST is not because showing obvious activity, therefore not listing without active constituent Nano silver grain).At 25 DEG C
Under the conditions of, AgPR-ST is similar to AgPR-T, shows highly selective catalytic action to specific substrate p nitrobenzyl alcohol；Phase
Than under, under the conditions of 50 DEG C, AgPR-ST becomes similar to AgPR-S, to p nitrobenzyl alcohol and the like ortho-nitrophenyl first
Alcohol does not show selectivity.The AgPR-ST catalyst of preparation show selectivity can modulation catalytic action feature.
Embodiment 2:
It is operated with embodiment 1, long-chain function monomer is changed to 2- nonenoic acid (6mmol), it is other to be grasped completely with embodiment 1
Make, the silver-colored load aggregation object catalyst AgPR-ST that obtained transition point is about 38 DEG C.It is surveyed in the identical catalysis of same embodiment 1
Under the conditions of examination, it is selected above and compares measurement lower than 30 DEG C of transition point and 45 DEG C, the result is shown in Fig. 8.In 30 DEG C of conditions
Under, AgPR-ST is similar to AgPR-T, shows highly selective catalytic action to specific substrate p nitrobenzyl alcohol；Compared to it
Under, under the conditions of 45 DEG C, AgPR-ST becomes similar to AgPR-S, does not have to p nitrobenzyl alcohol and the like nitro alcohol
Have and shows selectivity.The AgPR-ST catalyst of preparation also show that selectivity can modulation catalytic action feature.
Embodiment 3:
It is operated with embodiment 1, long-chain function monomer is changed to octadecenic acid (3mmol), it is other to be grasped completely with embodiment 1
Make, the silver-colored load aggregation object catalyst AgPR-ST that obtained transition point is about 34 DEG C.It is surveyed in the identical catalysis of same embodiment 1
Under the conditions of examination, it is selected above and compares measurement lower than 28 DEG C of transition point and 40 DEG C, the result is shown in Fig. 9.In 28 DEG C of conditions
Under, AgPR-ST is similar to AgPR-T, shows highly selective catalytic action to specific substrate p nitrobenzyl alcohol；Compared to it
Under, under the conditions of 40 DEG C, AgPR-ST becomes similar to AgPR-S, does not have to p nitrobenzyl alcohol and the like nitro alcohol
Have and shows selectivity.The AgPR-ST catalyst of preparation also show that selectivity can modulation catalytic action feature.
Embodiment 4:
It is operated with embodiment 1, active constituent presoma is changed to nickel nitrate (2mmol), it is other to be grasped completely with embodiment 1
Make, ni-loaded catalyst NiPR-ST is made.Under the identical catalysis test condition of same embodiment 1, the result is shown in Figure 10.
The NiPR-ST catalyst of preparation also show selectivity can modulation catalytic action feature, show that Ag of the present invention load is convertible
Preparation of the preparation method of the polyalcohol catalyst of selectivity in the convertible selective polyalcohol catalyst of other Metal Supporteds
In have certain applicability.
Claims (6)
1. a kind of preparation method of the convertible selective polyalcohol catalyst of silver load, which is characterized in that as follows
It carries out: substrate to be measured and active component silver presoma is first dissolved in dimethyl sulfoxide and is complexed, add function monomer, crosslinking
Then agent and initiator lead to nitrogen deoxidation into solution, sealing is placed on irradiation under ultraviolet lamp and causes polymerization, before forming catalyst
Body is driven, forming Ag ion in catalyst precursor, through sodium borohydride reduction, products therefrom cleans removing trace through water, ethyl alcohol repeatedly
Substrate molecule after, vacuum drying is to get to the silver-colored disposable polyalcohol catalyst of carried selective；
The substrate to be measured is nitro compound, and active component silver presoma is silver iron compound；
The function monomer is the binary copolymerization function of constructing polymer molecule identification framework and movable function base side chain structure
Monomer system, including containing long-chain functional group monomer and without chain monomer, the long-chain functional group monomer is 10- hydroxyl -2-
Decylenic acid, 2- nonenoic acid or octadecenic acid；The no chain monomer is acrylic acid；Wherein, long-chain functional group monomer and without chain list
The molar ratio of both bodies is 1:4~8.
2. a kind of preparation method of the convertible selective polyalcohol catalyst of silver load according to claim 1,
It is characterized in that, the substrate to be measured is p nitrobenzyl alcohol or nitro alcohol, and active component silver presoma is silver nitrate.
3. a kind of preparation method of the convertible selective polyalcohol catalyst of silver load according to claim 1,
It is characterized in that, the crosslinking agent is N, and N- methylene-bisacrylamide, the initiator is azodiisobutyronitrile.
4. a kind of preparation method of the convertible selective polyalcohol catalyst of silver load according to claim 1,
It is characterized in that, the time of the logical nitrogen deoxidation is 5-10min, ultraviolet lamp irradiation time is 20-30h.
5. a kind of preparation method of the convertible selective polyalcohol catalyst of silver load according to claim 1,
It is characterized in that, the molar ratio of the substrate to be measured and active component silver presoma dosage is less than or equal to Ag ion coordination number 2；Crosslinking
Agent dosage is the 10~15% of function monomer integral molar quantity；Initiator amount is the 1~5% of function monomer gross mass.
6. a kind of preparation method preparation of the convertible selective polyalcohol catalyst of silver load according to claim 1
Polyalcohol catalyst, which is characterized in that the isomer mixture that the polyalcohol catalyst can be used for nitrobenzyl alcohol is direct
Prepare p-aminophenyl methanol.
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| CN104162451A (en) * | 2014-07-16 | 2014-11-26 | 江苏大学 | Preparation method of high selectivity and specificity nickel-based catalyst |
| CN104353494A (en) * | 2014-07-16 | 2015-02-18 | 江苏大学 | Preparation method of intelligent nickel-based catalyst with automatic on/off control function |
| CN104959163A (en) * | 2015-05-19 | 2015-10-07 | 江苏大学 | Controllable and adjustable metal nanoparticle-loaded polymer catalyst and preparation method thereof |
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2016
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| CN104162451A (en) * | 2014-07-16 | 2014-11-26 | 江苏大学 | Preparation method of high selectivity and specificity nickel-based catalyst |
| CN104353494A (en) * | 2014-07-16 | 2015-02-18 | 江苏大学 | Preparation method of intelligent nickel-based catalyst with automatic on/off control function |
| CN104959163A (en) * | 2015-05-19 | 2015-10-07 | 江苏大学 | Controllable and adjustable metal nanoparticle-loaded polymer catalyst and preparation method thereof |
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