CN109365002A - A kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction - Google Patents
A kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction Download PDFInfo
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- CN109365002A CN109365002A CN201811253590.3A CN201811253590A CN109365002A CN 109365002 A CN109365002 A CN 109365002A CN 201811253590 A CN201811253590 A CN 201811253590A CN 109365002 A CN109365002 A CN 109365002A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 46
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 36
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 18
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 17
- 238000006352 cycloaddition reaction Methods 0.000 title claims abstract description 12
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000012621 metal-organic framework Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 230000005389 magnetism Effects 0.000 claims abstract description 8
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 3
- -1 compound Tetrafluoroborate Chemical class 0.000 claims description 10
- 239000013148 Cu-BTC MOF Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 6
- 238000009938 salting Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000000696 magnetic material Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002184 metal Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UINDRJHZBAGQFD-UHFFFAOYSA-N 2-ethyl-1-methylimidazole Chemical compound CCC1=NC=CN1C UINDRJHZBAGQFD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
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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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/33—Electric or magnetic properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction, belong to fine chemistry industry synthesis application field.The present invention is using carbon dioxide and epoxychloropropane as raw material, using magnetic ionic liquids immobilized AlCl_3 catalyst as catalyst, 100-130 DEG C of reaction 18-48h；The magnetic ionic liquids immobilized AlCl_3 catalyst are as follows: the immobilized 1- amine ethyl-3-methylimidazole tetrafluoroborate in the cavity of magnetic MOF compound；Wherein: the magnetism MOF compound is Fe3O4@HKUST-1.Catalyst prepared by the present invention directly organic ion liquid catalyst it is immobilized in the lar nanometric cavities of metal-organic framework materials, preparation method is simple, operation be easy, catalyst combines the Common advantages of magnetic material, metal-organic framework materials and ionic liquid.
Description
Technical field
The present invention relates to a kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction, belong to
In fine chemistry industry synthesis application field.
Background technique
Carbon dioxide and epoxide cycloaddition reaction are the important channels of carbon dioxide activation conversion, and product is ring-type
Carbonic ester is widely used in high boiling solvent, fine chemicals intermediate and polymer monomer.Metal complex, quaternary ammonium salt and
The homogeneous catalysts such as ionic liquid can effectively be catalyzed carbon dioxide and epoxide cycloaddition reaction, but homogeneous catalyst separation
Recycling is difficult, and product aftertreatment technology is complicated, limits its industrial application.Immobilized homogenous catalyst can avoid this to ask
Topic, such as metal complex, ionic liquid and quaternary ammonium salt are carried on solid carrier, it can prepare for carbon dioxide and epoxidation
Close the catalyst of object cycloaddition reaction.Compared with homogeneous catalyst, heterogeneous catalyst activity is low, severe reaction conditions, and exploitation is high
Effect, easily separated and recyclable heterogeneous catalyst are of great significance.But since there is still a need for make for the separation of product and catalyst
With the methods of centrifugation, can't be widely applied to industrially come.
Summary of the invention
The present invention is solved by applying magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction
The above problem.
The present invention provides a kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction,
Using carbon dioxide and epoxychloropropane as raw material, using magnetic ionic liquids immobilized AlCl_3 catalyst as catalyst, 100-130 DEG C of reaction
18-48h；Wherein, the dosage of the carbon dioxide of every 1MPa dosage, epoxychloropropane is 14-48mmol, and the dosage of catalyst is
30-100mg；The magnetic ionic liquids immobilized AlCl_3 catalyst are as follows: the immobilized 1- amine ethyl-in the cavity of magnetic MOF compound
3- methyl imidazolium tetrafluoroborate；Wherein: the magnetism MOF compound is Fe3O4@HKUST-1。
1- amine ethyl-3-methylimidazole tetrafluoroborate ([AEMIm] BF of the present invention4) structural formula it is as follows:
The present invention is preferably that the supported quantity of the 1- amine ethyl-3-methylimidazole tetrafluoroborate is 1.57-2.14mmol/
g。
The present invention is preferably the magnetic ionic liquids immobilized AlCl_3 catalyst the preparation method comprises the following steps: by 1- amine ethyl -3- first
Base tetrafluoroborate is immobilized in the cavity of magnetic MOF compound.
The present invention is preferably that the preparation method of the magnetic ionic liquids immobilized AlCl_3 catalyst includes the following steps: 1. to pass through
Paddling process is impregnated in Fe3O4HKUST-1 film is coated on surface, obtains magnetic MOF compound；2. magnetic MOF compound is dispersed in
In 1- amine ethyl-3-methylimidazole tetrafluoro boric acid salting liquid, the magnetism MOF compound and 1- amine ethyl-3-methylimidazole four
The weight ratio of borofluoride is 0.8-1.2:0.3-0.5, obtains magnetic ionic liquids immobilized AlCl_3 catalyst.
The present invention is preferably that the concentration of the 1- amine ethyl-3-methylimidazole tetrafluoro boric acid salting liquid is 1.5-2mg/mL.
The present invention dissolves the solvent of the 1- amine ethyl-3-methylimidazole tetrafluoroborate at least one in water and ethyl alcohol
Kind.
Magnetic MOF compound is preferably dispersed in 1- amine ethyl-3-methylimidazole tetrafluoro boric acid salting liquid by the present invention,
45-55 DEG C of stirring 12-24h.
Magnetic MOF compound is preferably dispersed in 1- amine ethyl-3-methylimidazole tetrafluoro boric acid salting liquid by the present invention,
45-55 DEG C of stirring 12-24h, washing, magnetic capture obtain magnetic ionic liquids immobilized AlCl_3 catalyst.
HKUST-1 of the present invention has metal unsaturation vacancy, can when being activated under the conditions of being greater than 100 DEG C
So that metallic site sloughs the hydrone or organic solvent molecule of absorption, metal unsaturation vacancy is exposed.
The invention has the following beneficial effects: the present invention will have high epoxidation by a kind of rear synthesis modification method of chemical anchoring
Ionic liquid [AEMIm] BF of catalytic activity4It is introduced into the lar nanometric cavities of magnetic MOF compound, then passes through amino and metal
The effect that chemical bond occurs for unsaturated vacancy carrys out immobilized [AEMIm] BF4Ionic-liquid catalyst prepares a kind of novel magnetism
Supported ionic liquids catalyst.The method using magnetic MOF compound solid-loaded ionic-liquid combines magnetic material, MOFs
The Common advantages of porous material and ionic-liquid catalyst are metal-organic framework materials in magnetic material and heterogeneous catalysis
A bridge is provided using providing a new platform, while also for heterogeneous catalysis and homogeneous ionic-liquid catalyst.
Compared with the background art: catalyst prepared by the present invention directly has in metal organic ion liquid catalyst is immobilized
In the lar nanometric cavities of machine framework material, preparation method is simple, and operation is easy, and it is organic that catalyst combines magnetic material, metal
The Common advantages of framework material and ionic liquid.To CO under the conditions of relatively mild2Cycloaddition reaction show preferably to urge
The excellent performance changing activity and reusing.Catalyst prepared by the present invention is with catalytic activity is good, stability is high, product separation
It is simple and quick, preparation process is environmentally protective and the excellent performance that may be reused, industrially practical application with higher
Property.
Detailed description of the invention
3 width of attached drawing of the present invention,
Fig. 1 is Fe described in embodiment 13O4@Cu(OH)3NO3、Fe3O4@HKUST-1 and IL/Fe3O4The XRD of@HKUST-1 is composed
Figure；
It is obtained by Fig. 1, IL/Fe3O4@HKUST-1 is Fe3O4With the composite material of HKUST-1, with pure phase Fe3O4And HKUST-1
It compares, IL/Fe3O4The position of@HKUST-1 characteristic peak is consistent, but diffraction peak intensity has a little difference, is illustrated modified
Catalyst still keeps the crystal structure of complete HKUST-1.
Fig. 2 is Fe described in embodiment 13O4@Cu(OH)3NO3、Fe3O4@HKUST-1 and IL/Fe3O4The FT-IR of@HKUST-1
Spectrogram；
It is obtained by Fig. 2, with Fe3O4@Cu(OH)3NO3And Fe3O4@HKUST-1 is compared, the catalyst of immobilized magnetic ionic liquids
There is the characteristic peak of the C=C stretching vibration of the characteristic peak and imidazole ring of apparent N-H bending vibration, and in Fe3O4@
HKUST-1 and IL/Fe3O4In@HKUST-1, nitro N=O stretching vibration characteristic peak disappears instead C=O double bond is stretched
Contracting vibration, it was demonstrated that HKUST-1 is synthesized and is stabilized, and is consistent with synthesis process.
Fig. 3 is Fe described in embodiment 13O4、Fe3O4@HKUST-1 and IL/Fe3O4The N of@HKUST-12Physical absorption desorption
Isothermal curve and pore-size distribution；
It is obtained by Fig. 3, due to compound, the Fe of HKUST-13O4The specific surface area of@HKUST-1 is much larger than Fe3O4, Fe3O4@
After the immobilized magnetic ionic liquids of HKUST-1, adsorbance is reduced, and Kong Rongyu specific surface area reduces, and illustrates that magnetic ionic liquids are consolidated
It is loaded in the cavity of skeleton.
Specific embodiment
Following non-limiting embodiments can with a person of ordinary skill in the art will more fully understand the present invention, but not with
Any mode limits the present invention.
Test method described in following embodiments is unless otherwise specified conventional method；The reagent and material, such as
Without specified otherwise, commercially obtain.
Embodiment 1
A kind of preparation method of magnetic ionic liquids immobilized AlCl_3 catalyst, the preparation method include the following steps:
I. magnetic Nano Fe3O4Preparation: first by the C of 1mmol6H5Na2O7·2H2O, the NaOH and 0.2mol of 4mmol
NaNO3It is added to after mixing in 19mL deionized water, is stirred evenly on magnetic stirring apparatus, and be heated at 100 DEG C transparent
Solution；Again by the FeSO of 1mL4·4H2O is added rapidly in above-mentioned clear solution, in 100 DEG C of heating 1h, naturally cools to room
Temperature, magnet are collected, are scattered in deionized water, ultrasonic 10min, and repeated multiple times, are washed out, are dried to obtain magnetic Nano
Fe3O4；
II. the preparation of magnetism MOF compound: first by above-mentioned magnetic Nano Fe3O4In 110 DEG C of vacuum drying 12h；In room temperature
Under, then by the magnetic Nano Fe of 98mg3O4It is scattered in the Cu (NO of 30mL3)2·3H2In the ethanol water of O, Cu (NO3)2·
3H2The concentration of the ethanol water of O is 0.02g/mL, and ethanol water includes 25mL ethyl alcohol and 5mL water, and stirring for 24 hours, is centrifuged,
Washing, is dried to obtain magnetic MOF compound；
III. 100mg magnetism MOF compound the preparation of catalyst: is dispersed in [AEMIm] BF of 20mL4In solution,
[AEMIm]BF4The concentration of solution is 2mg/mL, and 65 DEG C of stirrings for 24 hours, until solvent evaporates, are washed, magnetic capture is urged
Agent.
Embodiment 2
The application of magnetic ionic liquids immobilized AlCl_3 catalyst prepared by embodiment 1 in carbon dioxide cycloaddition reaction, will
Catalyst and 29mmol epoxychloropropane prepared by 30mg embodiment 1 is added in stainless steel reactor, is sealed, after ventilation,
The CO for being passed through 1MPa is stirred at room temperature down2, and 120 DEG C of reactions for 24 hours, after reaction, cool down and release in reactor under stiring
Remaining CO2, by the catalyst in reaction solution by magnetic capture, take supernatant liquor to analyze conversion ratio on gas chromatograph to be
93%, it is 100% that selectivity is analyzed on GC-MS.
Claims (7)
1. a kind of application of magnetic ionic liquids immobilized AlCl_3 catalyst in carbon dioxide cycloaddition reaction, it is characterised in that: with
Carbon dioxide and epoxychloropropane are raw material, using magnetic ionic liquids immobilized AlCl_3 catalyst as catalyst, 100-130 DEG C of reaction
18-48h；
Wherein, the carbon dioxide of every 1MPa dosage, the dosage of epoxychloropropane are 14-48mmol, and the dosage of catalyst is 30-
100mg；
The magnetic ionic liquids immobilized AlCl_3 catalyst are as follows: the immobilized 1- amine ethyl -3- methyl in the cavity of magnetic MOF compound
Tetrafluoroborate；
Wherein: the magnetism MOF compound is Fe3O4@HKUST-1。
2. application according to claim 1, it is characterised in that: the 1- amine ethyl-3-methylimidazole tetrafluoroborate
Supported quantity is 1.57-2.14mmol/g.
3. application according to claim 2, it is characterised in that: the preparation side of the magnetic ionic liquids immobilized AlCl_3 catalyst
Method are as follows: 1- amine ethyl-3-methylimidazole tetrafluoroborate is immobilized in the cavity of magnetic MOF compound.
4. application according to claim 3, it is characterised in that: the preparation side of the magnetic ionic liquids immobilized AlCl_3 catalyst
Method includes the following steps:
1. by dipping paddling process in Fe3O4HKUST-1 film is coated on surface, obtains magnetic MOF compound；
2. magnetic MOF compound is dispersed in 1- amine ethyl-3-methylimidazole tetrafluoro boric acid salting liquid, the magnetism MOF is multiple
The weight ratio for closing object and 1- amine ethyl-3-methylimidazole tetrafluoroborate is 0.8-1.2:0.3-0.5, obtains magnetic ionic liquids
Immobilized AlCl_3 catalyst.
5. application according to claim 4, it is characterised in that: the 1- amine ethyl-3-methylimidazole tetrafluoroborate is molten
The concentration of liquid is 1.5-2mg/mL.
6. application according to claim 5, it is characterised in that: magnetic MOF compound is dispersed in 1- amine ethyl -3- methyl
In tetrafluoroborate solution, 45-55 DEG C of stirring 12-24h.
7. application according to claim 6, it is characterised in that: magnetic MOF compound is dispersed in 1- amine ethyl -3- methyl
In tetrafluoroborate solution, 45-55 DEG C of stirring 12-24h is washed, and magnetic capture obtains magnetic ionic liquids solid-carrying type and urges
Agent.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114806723A (en) * | 2021-12-14 | 2022-07-29 | 曲阜师范大学 | Magnetic mesoporous polyion liquid interface catalytic hydrogenation reaction and biodiesel preparation |
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