CN109851803A - A kind of preparation method and application of the metal porous coordination polymer of glycosyl - Google Patents
A kind of preparation method and application of the metal porous coordination polymer of glycosyl Download PDFInfo
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- CN109851803A CN109851803A CN201811606241.5A CN201811606241A CN109851803A CN 109851803 A CN109851803 A CN 109851803A CN 201811606241 A CN201811606241 A CN 201811606241A CN 109851803 A CN109851803 A CN 109851803A
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Abstract
The present invention discloses a kind of preparation method and application of porous coordination coordination polymer of glycosyl, preparation method, which includes the following steps, to be contained skeleton or polymerization reaction generation Porous coordination polymer occurs for the various organic compounds with asymmetric carbon atom such as monosaccharide of the part containing hydroxyl, aldehyde radical or ketone group, disaccharides or polysaccharide and the salt ball milling containing each metal ion species, it is heated to 400-1200 DEG C of carbonization, obtains the porous carbon materials based on Porous coordination polymer.Porous carbon materials based on chiral Porous coordination polymer of the invention have hierarchical porous structure, aperture is adjustable, at low cost, preparation process is simple, stability is good, safety is good, easy to use and repeatable recycling uses, and can be used for the various fields such as gas absorption, chiral separation, catalysis and gas storage.
Description
Technical field
The present invention relates to a kind of using sugar as the synthetic method of the chiral porous metals coordination polymer of organic ligand, especially relates to
And ligand is the various organic compounds with asymmetric carbon atom such as the monosaccharide containing hydroxyl, aldehyde radical or ketone group, disaccharides or polysaccharide
And the salt containing each metal ion species occurs polymerization reaction and generates Porous coordination polymer.
Background technique
Porous coordination polymer (PCP) or metal organic frame (MOF) are a kind of organic inorganic hybridization porous materials, it has
Have the advantages that structure designability is good, specific surface area is high, performance is abundant, be concerned in recent years, and in gas absorption point
It is had been widely used from numerous areas such as, energy storage device, catalysis, medicament slow releases.Usual Porous coordination polymer, by organic
Ligand and metal ion or metal cluster are constituted, and organic ligand plays structural support effect, and metal ion or metal cluster play sky
Between node act on, traditional organic ligand is with containing the groups such as polycarboxylic acid, imidazoles, in order to obtain special Space expanding,
Organic ligand usually requires multi-step design synthesis, higher cost；Furthermore the further drawback of Porous coordination polymer is stability
Poor, once decomposing, the toxicity of organic ligand would have to be considered wherein；Therefore cheap, safe and inexpensive porous
The exploitation of the synthetic method of organic coordination polymer, is just particularly important.
The derivatization of MOF material is also nearest scientific research field hot spot, can obtain all kinds of porous carbons, more by being controllably pyrolyzed
The materials such as hole carbon-metal, nano-metal particle.Since molecule and atom are uniformly distributed in MOF material and specific surface area is high, because
The material of this this kind of derivatization generally has better controllability and uniformity, can be widely applied to supercapacitor, secondary
Battery, fuel cell, in water electrolysis hydrogen production gas.But natively there is the problems such as at high cost, low output in the synthesis of MOF material,
Carbonization treatment is carried out as raw material using it, and defect is clearly present in economic cost.And set out with the metal porous polymer of glycosyl, into
The development and application exploratory development of row porous material, can greatly reduce the synthesis cost of novel carbon-based material, so that MOF
The application prospect of derived material is more bright and clear.
Hydrothermal/solvent thermal synthesis is the system of the most widely used organic metal Porous coordination polymer in synthetic method
Preparation Method, metal salt and organic ligand are capable of forming target in closed high temperature and pressure system, by the crystallization of long period
Material.This method equipment investment is small, synthesis cost is low, it can be difficult to being prepared on a large scale.The present invention is using ball-milling method preparation coordination
Porous polymer can once prepare a large amount of material, be suitble to pilot scale and amplification.
The cyclodextrin metal-organic framework materials for having there is document report to prepare based on cyclodextrin and alkali metal ion
There is more environmental-friendly characteristic can be used in diformazan by (CD-MOF, J.Am.Chem.Soc., 2015,137,5706), CD-MOF
The separation of benzene homologue.Different, the invention patent is ligand using extensive carbohydrate, using the method for ball milling, inexpensive,
Large-scale preparation has the novel porous coordination polymer of chirality function, and can prepare the carbon-based function of series by derivatization
It can material.
Summary of the invention
The purpose of the present invention is obtain to have the chiral metal porous coordination polymer of glycosyl as ligand using all kinds of glycan molecules
And be applied to various gas absorptions, chiral separation, catalysis, water process etc..
Sugared selection includes: monosaccharide (erythrose, Su Li sugar, arabinose, ribose, xylose, lyxose, Portugal in the present invention
Grape sugar, mannose, fructose, galactolipin etc.), disaccharides (lactose, sucrose, maltose etc.), polysaccharide (glycogen, xylose, starch, fiber
Element etc.) one or more of mixing；The selection of metal ion from conventional transition metal to main group metal, mainly include Zn,
The metal ions such as Mg, Cu, Co, Fe, Ni, Cd, Ag, Pd, Pt, Pb, other metal ions and metal cluster can significantly with hydroxyl shape
Also within this range at coordination.
The main method of synthesis is solid-phase ball milling method and water heating kettle synthetic method.The method of the present invention raw material sources are extensive, synthesis
Process is solvent-free, and green non-pollution is suitble to a large amount of preparations.This method has wide application space, such as with chiral sugar for ligand
The Porous coordination polymer of preparation also has chirality, can apply in chiral drug detaching direction；Carbohydrate is Edible material, with
The micro elements needed by human such as Zn, Mg preparation Porous coordination polymer can carry medicine, sustained release, in terms of have it is wide
Application space；Using polysaccharide such as cheap cellulose, starch as raw material, the porous polymer of acquisition can be in terms of sewage treatment
It is applied.
These glycosyl Porous coordination polymers can get carbon-based new material application in the energy by further pyrolysis processing
Field.
Technical solution of the present invention:
The selection of carbohydrate ligands: being contained with skeleton or monosaccharide of the part containing hydroxyl, aldehyde radical or ketone group, disaccharides or polysaccharide etc.
It is various that there is asymmetric carbon atom.
With sugar be ligand proportionally mixed with metal salt, then with a certain amount of alkali (potassium carbonate, sodium carbonate, sodium bicarbonate,
Saleratus) mixing, a series of metal porous coordination polymers of glycosyl with chirality can be prepared by ball-milling treatment.
The derivatization of glycosyl Porous coordination polymer: above-mentioned steps polymer obtained is weighed into a certain amount, lazy
Property atmosphere in, be carbonized under 400 DEG C of -1200 DEG C of different temperatures using tube furnace, then sufficiently wash material with pure water
Material 2-3 times removes salt, obtains porous carbon or porous carbon and metallic composite.
Salt containing same metal ion polymerize with the different sugar polymerization mix preparation containing hydroxyl, aldehyde radical or ketone group
Structure, the crystalline state of object carbon material are similar, will not change its structure.
Salt containing different types of metal ion is prepared with the sugared polymerization mix of the same race containing hydroxyl, aldehyde radical or ketone group
The structure of polymer carbon material, crystalline state it is different, its structure can be changed.
Utilize the salt containing different types of metal ion and the sugared polymerization mix of the same race containing hydroxyl, aldehyde radical or ketone group
The polymer of preparation and independent saccharide raw material carry out the test of circular dichroism spectrometer, it was demonstrated that the Porous coordination polymer of preparation has hand
Property.
The filling of splitter, it is mixed by solvent of methanol, ethyl alcohol or acetonitrile using the Porous coordination polymer of preparation as filler
Slurry in filled therewith to stainless steel chromatographic column, will be used for the research of high performance liquid chromatography chiral separation using high-pressure plunger pump, chiral
Separating effect is analyzed with refractometer.
Metal ion removal aspect in water contains metal with what the Porous coordination polymer of acquisition was added to various concentration
In the solution of ion, by the stirring of different time (0-75min), with Cd2+、Cu2+、Pb2+、Fe3+、Zn2+、Co2+、Sn4+Deng from
Exchange and capture occur for son, and ion concentration is analyzed using x-ray fluorescence spectrometry instrument (XRF).
The gas absorption of the derivatization porous carbon of Porous coordination polymer separates, gas absorption using gas absorption instrument into
Row CO2、CH4、N2Isoequilibrium absorption test, the control of temperature are carried out with liquid nitrogen and thermostatic circulation bath, and gas separating experiment will
Porous carbon is filled in progress breakthrough of gas behavior in packed column and is verified.
The advantages of the present invention are:
The metal porous coordination polymer of the glycosyl of the invention, raw material sources extensively, green, at a low price, synthetic method green, letter
Just, it is easy amplification, there is chirality, molecular structure, pore size can easily be accommodated the Porous coordination polymer of preparation, stability and peace
Good perfection can be used for separating, water process, medicament slow release etc., can also further derive and turn to the compound use of porous carbon sill of sheet
In energy field.
Detailed description of the invention
Fig. 1 is the XRD diagram for the part glycosyl Porous coordination polymer that the present invention obtains.
Fig. 2 is the infrared figure for the part glycosyl Porous coordination polymer that the present invention obtains.
Fig. 3 is the nitrogen adsorption isotherm figure for the glycosyl Porous coordination polymer that the present invention obtains.
Fig. 4 is the graph of pore diameter distribution for the glycosyl Porous coordination polymer that the present invention obtains.
Fig. 5 is the circular dichroism spectrogram of the sucrose-Co base and sucrose-Ni base Porous coordination polymer that obtain in the present invention.
Fig. 6 is the circular dichroism spectrogram of the fructose-Co base and fructose-Ni base Porous coordination polymer that obtain in the present invention.
Fig. 7 is glycosyl Porous coordination polymer underwater gold category ion cleaning front and back concentration in the present invention.
Fig. 8 is the nitrogen adsorption isotherm figure of the derivative porous carbon of glycosyl Porous coordination polymer in the present invention.
Fig. 9 is the flue gas mask data of the derivative porous carbon of glycosyl Porous coordination polymer in the present invention.
Specific embodiment
Embodiment 1:
(1) sucrose (600mg), zinc acetate (Zn (OAC) are taken2, 300mg) and potassium carbonate (1200mg) be added to clean ball
In grinding jar, weighing is added in ball grinder, and complexation reaction occurs for ball milling 20min on planetary ball mill, is prepared containing sugarcane
Sugar-Zn Porous coordination polymer, the Porous coordination polymer after reaction is with deionized water repeated flushing 3 times.X-ray diffraction characterization
Show that the Porous coordination polymer prepared with polyose metal belongs to amorphous materials.Infrared data shows glycosyl ligand and metal
Ion is successfully coordinated.Gas absorption test shows that the coordination polymer of acquisition is porous structure, and specific surface area is higher.
Embodiment 2:
(1) fructose (600mg), zinc acetate (Zn (OAC)2, 300mg) and potassium carbonate (1200mg) be added to clean ball milling
In tank, weighing is added in ball grinder, and complexation reaction occurs for ball milling 20min on planetary ball mill, is prepared containing sucrose-
Zn Porous coordination polymer, the Porous coordination polymer after reaction is with deionized water repeated flushing 3 times.
(2) polymer for preparing step (1) is from potassium hydroxide (KOH) according to different mass ratio (1:0,1:1,1:2
Deng) grinding in agate mortar is added uniformly, is then carbonized in inert gas to resulting materials, with 2-5 DEG C/min from room
Temperature is warming up to 400-800 DEG C, keeps the temperature 2h, is cooled to room temperature, acquires black solid.Resulting black solid is subjected to pickling
(1M HCl) washs a night, then uses pure water 2 times, to remove sylvite.It is dried in vacuum overnight, obtains at 80 DEG C later
Porous carbon materials based on Porous coordination polymer of the invention.
Embodiment 3:
(1) maltose (600mg), nickel acetate (Ni (OAC) 2,300mg) and potassium carbonate (1200mg) are added to clean ball
In grinding jar, weighing is added in ball grinder, and complexation reaction occurs for ball milling 20min on planetary ball mill, prepares maltose-
Ni Porous coordination polymer, the Porous coordination polymer after reaction is with deionized water repeated flushing 3 times.
(2) polymer for preparing step (1) is from potassium hydroxide (KOH) according to different mass ratio (1:0,1:1,1:2
Deng) grinding in agate mortar is added uniformly, is then carbonized in inert gas to resulting materials, with 2-5 DEG C/min from room
Temperature is warming up to 400-800 DEG C, keeps the temperature 2h, is cooled to room temperature, acquires black solid.Resulting black solid is subjected to pickling
(1M HCl) washs a night, then uses pure water 2 times, to remove sylvite.It is dried in vacuum overnight, obtains at 80 DEG C later
Porous carbon materials based on Porous coordination polymer of the invention.
Embodiment 4:
(1) alpha-D-glucose (800mg), zinc acetate (Zn (OAC)2, 300mg) and potassium carbonate (1200mg) be added to completely
Ball grinder in, weighing be added in ball grinder, on planetary ball mill ball milling 20min occur complexation reaction, prepare and contain
There is alpha-D-glucose-Zn Porous coordination polymer, the Porous coordination polymer after reaction is with deionized water repeated flushing 3 times.
(2) alpha-D-glucose-Zn Porous coordination polymer carries out circular dichroism spectra detection, obtains apparent chiral signal.
(3) using methanol as solvent, alpha-D-glucose-Zn Porous coordination polymer is beaten, by high-pressure plunger pump by α-
In stainless steel high performance liquid chromatography (HPLC) column that it is 8mm to internal diameter that D-Glucose-Zn Porous coordination polymer, which is filled, it will prepare
HPLC column be connected in liquid chromatograph and carry out separation test.
Embodiment 5:
(1) cyclodextrin (700mg), zinc acetate (Ni (OAC)2, 300mg) and potassium carbonate (1200mg) be added to clean ball
In grinding jar, weighing is added in ball grinder, and complexation reaction occurs for ball milling 20min on planetary ball mill, prepares cyclodextrin-
Zn Porous coordination polymer, the Porous coordination polymer after reaction is with deionized water repeated flushing 3 times.
(2) polymer prepared by step (1) is placed in and fills FeCl2、PbCl2、ZnCl2、SnCl4In solution, by not
The stirring of same time (0-75min) is chosen supernatant liquor in different time sections and is detected, done with original solution ions content
It compares, the Fe in the time of stirring longer solution3+、Pb2+、Sn4+、Zn2+Plasma content significantly reduces, and illustrates the glycosyl of preparation
Porous coordination polymer has the function of that exchange and capture occur for metal ion, can be used for the purification of metal ions in sewage.
Fig. 1 is the XRD diagram for the part glycosyl Porous coordination polymer that the present invention obtains, and shows the porous metals coordination of synthesis
Polymer is unbodied noncrystalline compound.
Fig. 2 is the infrared figure for the part glycosyl Porous coordination polymer that the present invention obtains, and shows that the porous polymeric of synthesis has
The signal of polysaccharide group.
Fig. 3 is the nitrogen adsorption isotherm figure for the glycosyl Porous coordination polymer that the present invention obtains, and shows the porous of synthesis
Polymer belongs to micro- composite mesoporous porous material.
Fig. 4 is the graph of pore diameter distribution for the glycosyl Porous coordination polymer that the present invention obtains, and shows pore size distribution information for multistage
Pore size distribution is distributed from 0.5nm-5nm.
Fig. 5 is the circular dichroism spectrogram of the sucrose-Co base and sucrose-Ni base Porous coordination polymer that obtain in the present invention, table
The sucrose base Porous coordination polymer of bright synthesis has chiral signal, and chiral signal is originated from polysaccharide.
Fig. 6 is the circular dichroism spectrogram of the fructose-Co base and fructose-Ni base Porous coordination polymer that obtain in the present invention, table
The fructosyl Porous coordination polymer of bright synthesis has chiral signal, and chiral signal is originated from polysaccharide.
Fig. 7 is glycosyl Porous coordination polymer underwater gold category ion cleaning front and back concentration in the present invention, illustrates porous polymeric
Object has metal pollutant processing capacity.
Fig. 8 is the nitrogen adsorption isotherm figure of the derivative porous carbon of glycosyl Porous coordination polymer in the present invention, illustrates to derive
Porous carbon have high specific surface area.
Fig. 9 is the flue gas mask data of the derivative porous carbon of glycosyl Porous coordination polymer in the present invention, illustrates porous carbon
With flue gas CO2/N2Separating capacity, and being capable of circular regeneration use.
Various embodiments provided by the invention can be combined with each other in any way as needed, be obtained by this combination
Technical solution, it is also within the scope of the invention.
Obviously, in the case where not departing from theory and method of the invention, those skilled in the art can to the present invention into
The various modification and variations of row.If being in claim and its equivalent program of the invention to these modification and variations of the invention
In range, then the present invention also will include these modification and variations.
Claims (4)
1. a kind of preparation method of the metal porous coordination polymer of glycosyl, it is characterised in that: contain skeleton or part is contained
Hydroxyl, the monosaccharide of aldehyde radical or ketone group, disaccharides or the various organic compounds with asymmetric carbon atom of polysaccharide with contain various metals
The salt of ion occurs polymerization reaction and generates Porous coordination polymer.
2. the preparation method of the metal porous coordination polymer of glycosyl according to claim 1, it is characterised in that: match porous
Position polymer is uniformly mixed from pore creating material according to different mass ratioes, under inert gas conditions with 2-5 DEG C/min heating rate
It is heated to 400-1200 DEG C of carbonization 2-6h, obtains the porous carbon materials based on Porous coordination polymer.
3. the preparation method of the metal porous coordination polymer of glycosyl according to claim 1, it is characterised in that: carbohydrate and gold
Belonging to salt can be optionally combined；From conventional transition metal to main group metal, ligand is matched from simple hydroxyl for the selection of metal center ion
Body is to heterocyclic ligand, mixed ligand.
4. the application of the metal porous coordination polymer of any one of the claim 1-3 glycosyl, it is characterised in that: gained is porous to match
Position polymer application field includes that gas absorption, chiral separation, underwater gold category ion cleaning, catalysis and gas storage ring protect field
In.
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|---|---|---|---|---|
| CN113527703A (en) * | 2021-07-16 | 2021-10-22 | 淮阴师范学院 | Metal carbon-based coordination polymer, preparation method and application thereof in synthesis of 2, 5-furandimethanol |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101618047A (en) * | 2009-08-11 | 2010-01-06 | 聊城大学 | Preparation method and application of nanocomposite of silver, chitosan and/or derivative thereof |
| CN101654529A (en) * | 2009-09-15 | 2010-02-24 | 聊城大学 | Preparation method and application of chitosan and/or metal composite of chitosan derivative |
| CN101781374A (en) * | 2010-02-04 | 2010-07-21 | 聊城大学 | Preparation method and application of copper compound with chitosan and/or derivatives thereof |
| CN101844742A (en) * | 2010-05-27 | 2010-09-29 | 复旦大学 | Bioactive nano porous material and preparation method thereof |
| WO2011116222A2 (en) * | 2010-03-17 | 2011-09-22 | Northwestern University | Nanoporous carbohydrate frameworks and the sequestration and detection of molecules using the same |
| CN103303912A (en) * | 2013-07-05 | 2013-09-18 | 黑龙江大学 | Preparation method of high-specific-surface-area porous nitrogen-doped graphitizing carbon nanomaterial |
| CN103769058A (en) * | 2014-01-08 | 2014-05-07 | 浙江大学 | Preparation method of carbonized chitosan adsorbent, adsorbent and application method of absorbent |
| CN105642243A (en) * | 2016-01-20 | 2016-06-08 | 南京中医药大学 | Preparation method of chitosan-based activated carbon containing transition metal ions |
| CN105814118A (en) * | 2014-06-06 | 2016-07-27 | 西北大学 | Carbohydrate-mediated purification of petrochemicals |
| CN106188200A (en) * | 2016-08-01 | 2016-12-07 | 南宁市泽威尔饲料有限责任公司 | The preparation method of sucrose zinc complex |
| CN107840334A (en) * | 2017-12-19 | 2018-03-27 | 中国石油大学(华东) | A kind of atomic hole porous carbon materials and preparation method thereof |
| CN108070090A (en) * | 2016-11-14 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of sugar-metal coordinating polymer material and preparation method thereof |
| CN108070091A (en) * | 2016-11-14 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of chirality sugar-metal coordinating polymer material and preparation method thereof |
| CN108851004A (en) * | 2018-05-23 | 2018-11-23 | 中盐金坛盐化有限责任公司 | The preparation method and applications of carbohydrate metal complex |
-
2018
- 2018-12-27 CN CN201811606241.5A patent/CN109851803A/en active Pending
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101618047A (en) * | 2009-08-11 | 2010-01-06 | 聊城大学 | Preparation method and application of nanocomposite of silver, chitosan and/or derivative thereof |
| CN101654529A (en) * | 2009-09-15 | 2010-02-24 | 聊城大学 | Preparation method and application of chitosan and/or metal composite of chitosan derivative |
| CN101781374A (en) * | 2010-02-04 | 2010-07-21 | 聊城大学 | Preparation method and application of copper compound with chitosan and/or derivatives thereof |
| WO2011116222A2 (en) * | 2010-03-17 | 2011-09-22 | Northwestern University | Nanoporous carbohydrate frameworks and the sequestration and detection of molecules using the same |
| CN101844742A (en) * | 2010-05-27 | 2010-09-29 | 复旦大学 | Bioactive nano porous material and preparation method thereof |
| CN103303912A (en) * | 2013-07-05 | 2013-09-18 | 黑龙江大学 | Preparation method of high-specific-surface-area porous nitrogen-doped graphitizing carbon nanomaterial |
| CN103769058A (en) * | 2014-01-08 | 2014-05-07 | 浙江大学 | Preparation method of carbonized chitosan adsorbent, adsorbent and application method of absorbent |
| CN105814118A (en) * | 2014-06-06 | 2016-07-27 | 西北大学 | Carbohydrate-mediated purification of petrochemicals |
| CN105642243A (en) * | 2016-01-20 | 2016-06-08 | 南京中医药大学 | Preparation method of chitosan-based activated carbon containing transition metal ions |
| CN106188200A (en) * | 2016-08-01 | 2016-12-07 | 南宁市泽威尔饲料有限责任公司 | The preparation method of sucrose zinc complex |
| CN108070090A (en) * | 2016-11-14 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of sugar-metal coordinating polymer material and preparation method thereof |
| CN108070091A (en) * | 2016-11-14 | 2018-05-25 | 中国科学院大连化学物理研究所 | A kind of chirality sugar-metal coordinating polymer material and preparation method thereof |
| CN107840334A (en) * | 2017-12-19 | 2018-03-27 | 中国石油大学(华东) | A kind of atomic hole porous carbon materials and preparation method thereof |
| CN108851004A (en) * | 2018-05-23 | 2018-11-23 | 中盐金坛盐化有限责任公司 | The preparation method and applications of carbohydrate metal complex |
Non-Patent Citations (4)
| Title |
|---|
| SHI, F，等: "Mechanochemical Phosphorylation and Solubilisation of beta-D-Glucan from Yeast Saccharomyces cerevisiae and Its Biological Activities", 《PLOS ONE》 * |
| 刘志华 ，等: "基于环糊精配体骨架化合物的铜离子电化学行为及其检测", 《分析测试学报》 * |
| 王雪松，等: "糖类的金属络合物", 《化学通报》 * |
| 鲁彦: "新型糖-金属配合物结构与性质的研究", 《万方中国学位论文全文数据库》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527703A (en) * | 2021-07-16 | 2021-10-22 | 淮阴师范学院 | Metal carbon-based coordination polymer, preparation method and application thereof in synthesis of 2, 5-furandimethanol |
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Application publication date: 20190607 |