CN108620124A - A kind of porous polymer solid acid catalyst for alkynes hydration reaction - Google Patents
A kind of porous polymer solid acid catalyst for alkynes hydration reaction Download PDFInfo
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- CN108620124A CN108620124A CN201810505342.7A CN201810505342A CN108620124A CN 108620124 A CN108620124 A CN 108620124A CN 201810505342 A CN201810505342 A CN 201810505342A CN 108620124 A CN108620124 A CN 108620124A
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- solid acid
- porous polymer
- polymer solid
- hydration reaction
- acid catalyst
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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
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/26—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydration of carbon-to-carbon triple bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
Abstract
The invention belongs to alkynes hydration catalyst technical fields, more particularly to a kind of porous polymer solid acid catalyst for alkynes hydration reaction, the solid acid is using lipid as solvent, solvent heat copolymerization is carried out by divinylbenzene (DVB), 1 vinyl imidazole (vim) or 4 vinylpyridines (VP), sodium p styrene sulfonate, then with 1,3 propane sultones react to form quaternary ammonium salt, by carrying out ion exchange with acid, porous polymer solid acid is ultimately formed.The present invention prepares porous polymer solid acid, has larger BET surface area, is layered the acid strength of nano-pore and enhancing, while its structure-controllable, easily operated, can be mass-produced, has broad application prospects.
Description
Technical field
The invention belongs to alkynes hydration catalyst technical fields, and in particular to a kind of for the porous poly- of alkynes hydration reaction
Close object solid acid catalyst.
Background technology
Alkynes hydration prepares the Atom economy of carbonyls up to 100%, and alkynes raw material is easy to get, product added value compared with
Height, therefore be concerned in prepared by modern extensive Chemical Manufacture and fine chemicals.Especially ketone is as chemistry and pharmacy
Important intermediate in industry, they are widely used by alkynes hydration reaction is produced.However, traditional alkynes hydration
Usually using highly toxic mercury (II) salt as the catalyst in aqueous sulfuric acid, this seriously constrains them in the industry for reaction
Extensive use.In order to overcome the toxicity of mercury salt, extensive exploitation use various organo-metallic catalysts, such as containing Au,
The compound of Pt, Ag, Ru.Although improving conversion ratio and selectivity, these catalyst also have the shortcomings that following at least one：
(1) expensive noble metal (Au, Pt, Ru, Ag etc.)；(2) high reaction temperature (>100℃)；(3) a large amount of excessive water and additional
Acid additives；(4) limited functional group compatibility.Recently, find several bronsted sour (such as TfOH, HNTf2) to alkynes
The aquation of hydrocarbon shows extraordinary catalytic activity.However, these methods usually require stoichiometry or excessive acid, this
Lead to the separation of acidic catalyst and is recycled for difficulty.Therefore, exploitation is hydrated anti-alkynes under green and temperate condition
It is still in demand that should have efficient novel acid catalyst.
Acidic ion liquid (ILs) has been successfully introduced into acid catalysis field as a kind of novel green reaction medium,
This depends on its unique property, the vapour pressure such as ignored, significant solubility, various structures etc..It is homogeneous in order to promote
The separation and reuse of ILs catalyst, in these years, the porous polymer ILs catalyst containing acidic site and IL groups
Synthesis had gained considerable attention.As high activity acid catalyst mesoporous polymer ionic liquid should have with
Under several features, include larger BET surface area, stronger acid strength and increase active site degree of exposure.
The many polymer ions liquid reported at present have low-down acidic site concentration and the porosity be mutually on duty,
Which has limited their applications as solid acid in various acid catalyzed reactions, especially in hydration reaction.Therefore, tool is prepared
It is still a kind of challenge to have bigger serface, superpower acid strength, controllable and high acid levels porous polymer.Based on above-mentioned feelings
Condition, we report the preparation of strong acidic ion liquid functional nano-porous polymer, have adjustable hydrophilic-hydrophobic net
Network, classifying nano porosity, big BET specific surface area and strong acid intensity.The porous polymer passes through divinylbenzene (DVB) and 1-
Vinyl imidazole (vim) or 4-vinylpridine (VP) exist in the functional monomer of sodium p styrene sulfonate carries out solvent
Thermal copolymerization then uses 1,3-propane sultone to form quaternary ammonium salt, then carries out ion exchange, the porous polymeric of synthesis with acid
Object (ionic liquid) solid acid has larger BET surface area, is layered the acid strength of nano-pore and enhancing.Above-mentioned new feature makes
They have excellent catalytic activity, and improve the hydrogenation that alkynes hydration generates the reusability and amine and phenylacetylene of ketone
Reactivity, even better than Amberlyst 15, phosphotungstic acid and sulfuric acid.This work largely expands porous polymer
Catalytic applications of (ionic liquid) solid acid in hydration and hydroamination, this converts the raw material of industry to high added value in industry
Chemicals develop a kind of green, the method for high efficiency and low cost.
Invention content
For the problems of the prior art, the present invention provides a kind of porous polymer solid acid for alkynes hydration reaction
Catalyst has larger BET surface area, is layered the acid strength of nano-pore and enhancing, while its structure-controllable, easily operated,
It can be mass-produced, have broad application prospects.
To realize the above technical purpose, the technical scheme is that：
A kind of porous polymer solid acid catalyst for alkynes hydration reaction, the solid acid using lipid as solvent,
It is carried out by divinylbenzene (DVB), 1- vinyl imidazoles (vim) or 4-vinylpridine (VP), sodium p styrene sulfonate molten
Agent thermal copolymerization reacts, and then reacts to form quaternary ammonium salt with 1,3-propane sultone, by carrying out ion exchange, most end form with acid
At porous polymer solid acid.
The preparation method of the porous polymer solid acid catalyst is in accordance with the following steps：
Step 1, azodiisobutyronitrile is dissolved in lipid solvent, divinylbenzene is then added, added after stirring evenly
Enter 1- vinyl imidazoles or 4-vinylpridine carries out high-temperature solvent thermal response, obtains mixed reaction solution；
Step 2, by mixed reaction solution room temperature slow evaporation until solvent volatilize completely, obtain carrier material；
Step 3, carrier is put into toluene, 1,3-propane sultone is then added and carries out the quaternized processing of high temperature, passes through
It is washed using ethyl alcohol after filter, vacuum drying obtains sediment；
Step 4, sediment is put into the toluene solvant of acid and is handled, then dichloromethane used to wash, be dried in vacuo
To porous polymer solid acid.
Lipid solvent in the step 1 uses Ethyl formate, one or more of methyl acetate or ethyl acetate.
The reaction temperature of the high-temperature solvent thermal response in the step 1 is 80-160 DEG C, when the stirring of the stirring
Between 6-36h.
Mass concentration of the sediment in toluene solvant in the step 3 is 25-50g/L, the quaternized place of high temperature
For reason using being handled under room temperature, temperature is 100-160 DEG C, processing time 12-36h, the vacuum drying temperature after the ethyl alcohol washing
Degree is 80-120 DEG C, drying time 12-36h.
Acid in the step 4 uses HSO3CF3Or H2SO4；The CH2Cl2Vacuum drying temperature after washing is 100-
160 DEG C, drying time 24-48h.
Evaporation in the step 2 carries out under normal pressure.
Catalyst in the step 4 is used for alkynes hydration reaction.
The method of the alkynes hydration reaction is as follows：By catalyst and phenylacetylene, the mixing of deionized water and trifluoroethanol
Solution reacts in microwave tube, then utilizes its product of chromatography.
From the above, it can be seen that the present invention has following advantages：
1. the present invention prepares porous polymer solid acid, there is larger BET surface area, be layered the acid of nano-pore and enhancing
Intensity.Its structure-controllable simultaneously, it is easily operated, it can be mass-produced, have broad application prospects.
2. the present invention, which prepares porous polymer solid acid, has excellent catalytic activity, and significantly improves alkynes hydration
Generate the hydrogenation of the reusability and amine and phenylacetylene of ketone, even better than Amberlyst 15, phosphotungstic acid and sulfuric acid.
A kind of reaction process of green is provided for alkynes hydration reaction.
Description of the drawings
Fig. 1 is the infrared spectrum of porous ion liquid solid acid prepared by embodiment 1 to embodiment 4
Specific implementation mode
In conjunction with Fig. 1, the specific embodiment that the present invention will be described in detail, but any limit is not done to the claim of the present invention
It is fixed.
Embodiment 1
A kind of porous polymer solid acid catalyst for alkynes hydration reaction
Carrier synthesizes：2.0g DVB and 0.5g VP are added to the solution containing 0.07g AIBN and 30mL ethyl acetate
In.After being stirred at room temperature 12 hours, solvent heat treatment 24 hours, then slowly steaming at room temperature at 120 DEG C by mixed liquor
Send out solvent 2 days.Obtaining has the product (PDVB-VP-0.5) of whole pattern.
The PDVB-VP-0.5 carriers of preparation and 1,3-propane sultone is quaternized, then with HSO3CF3Carry out ion friendship
Change synthesis PDVB- [C3VP][SO3CF3]-0.5(C3Represent the quaternizing agent of 1,3- propane sultones).Specifically, violent
1.0g PDVB-VP-0.5 are added in 25mL toluene under stirring, 0.25g 1,3-propane sultone is then added.At 100 DEG C
Under after quaternized 24 hours, product is collected by filtration, is washed with a large amount of ethyl alcohol and is dried in vacuo 18h at 80 DEG C.Then by gained
Sample uses the HSO3CF3 in toluene solvant to handle 24 hours at room temperature, with a large amount of CH2Cl2Washing and the vacuum at 120 DEG C
Dry 24 hours to obtain PDVB- [C3VP][SO3CF3] -0.5 porous polymer solid acid.
Embodiment 2
A kind of porous polymer solid acid catalyst for alkynes hydration reaction
Carrier synthesizes：2.0g DVB and 0.2g VP are added to the solution containing 0.07g AIBN and 30mL Ethyl formates
In.After being stirred at room temperature 12 hours, solvent heat treatment 36 hours, then slowly steaming at room temperature at 100 DEG C by mixed liquor
Send out solvent 2 days.Obtaining has the product (PDVB-VP-0.2) of whole pattern.
The PDVB-VP-0.2 carriers of preparation and 1,3-propane sultone is quaternized, then with H2SO4Carry out ion exchange
Synthesize PDVB- [C3VP][SO4] -0.2 (C3 represents the quaternizing agent of 1,3- propane sultones).Specifically, with vigorous stirring
1.0g PDVB-VP-0.2 are added in 35mL toluene, 0.25g 1,3-propane sultone is then added.The quaternary ammonium at 130 DEG C
After changing 24 hours, product is collected by filtration, washed with a large amount of ethyl alcohol and dries 12h at 100 DEG C.Then by gained sample in room temperature
The lower H in toluene solvant2SO4Processing 24 hours, with a large amount of CH2Cl2Wash and be dried in vacuo at 140 DEG C 18 hours with
Obtain PDVB- [C3VP][SO4] -0.2 porous polymer solid acid.
Embodiment 3
A kind of porous polymer solid acid catalyst for alkynes hydration reaction
Carrier synthesizes：2.0g DVB and 0.4g vim are added to the solution containing 0.05g AIBN and 30mL methyl acetates
In.After being stirred at room temperature 24 hours, solvent heat treatment 36 hours, then slowly steaming at room temperature at 100 DEG C by mixed liquor
Send out solvent 2 days.Obtaining has the product (PDVB-vim-0.4) of whole pattern.
The PDVB-vim-0.4 carriers of preparation and 1,3-propane sultone is quaternized, then with HSO3CF3Carry out ion friendship
Change synthesis PDVB- [C3vim][SO3CF3]-0.4(C3Represent the quaternizing agent of 1,3- propane sultones).Specifically, violent
1.0g PDVB-vim-0.4 are added in 35mL toluene under stirring, 0.30g 1,3-propane sultone is then added.140
At DEG C after quaternized 36 hours, product is collected by filtration, washed with a large amount of ethyl alcohol and is dried in vacuo 12h at 80 DEG C.Then by institute
Sample is obtained at room temperature with the HSO in toluene solvant3CF3Processing 24 hours, with a large amount of CH2Cl2It washs and true at 140 DEG C
The dry 36h of sky is to obtain PDVB- [C3vim][SO3CF3] -0.4 porous polymer solid acid.
Embodiment 4
A kind of porous polymer solid acid catalyst for alkynes hydration reaction
Carrier synthesizes：2.0g DVB and 0.6g vim are added to the solution containing 0.09g AIBN and 30mL ethyl acetate
In.After being stirred at room temperature 26 hours, solvent heat treatment 36 hours, then slowly steaming at room temperature at 140 DEG C by mixed liquor
Send out solvent 2 days.Obtaining has the product (PDVB-vim-0.6) of whole pattern.
The PDVB-vim-0.6 carriers of preparation and 1,3-propane sultone is quaternized, then with HSO3CF3Carry out ion friendship
Change synthesis PDVB- [C3vim][SO3CF3]-0.6(C3Represent the quaternizing agent of 1,3- propane sultones).Typically, violent
1.0g PDVB-vim-0.6 are added in 40mL toluene under stirring, 0.35g 1,3-propane sultone is then added.140
At DEG C after quaternized 36h, product is collected by filtration, washed with a large amount of ethyl alcohol and is dried in vacuo for 24 hours at 160 DEG C.Then by gained
Sample uses the HSO in toluene solvant at room temperature3CF336h is handled, with a large amount of CH2Cl2It washs and vacuum is dry at 120 DEG C
It is dry for 24 hours to obtain PDVB- [C3vim][SO3CF3] -0.6 porous polymer solid acid.
Fig. 1 be embodiment 1- embodiments 4 prepare porous conjunction object solid acid catalyst in infrared spectrum, embody catalyst
Structure.
Test condition
The activity rating of catalyst is carried out on the magnetic force heating stirring reaction unit of German IKA companies：44mg is catalyzed
The phenylacetylene of 0.4mmol is added in agent, in the deionized water of 0.8mmol and the mixed solution of 2ml trifluoroethanols, reacts in microwave tube
Middle progress.Rotating speed is 1000 turns/min, and reactant is collected by centrifugation after reacting 18h.Qualitative and quantitative result passes through respectively
Thermo Trace 1300GC-ISQ and GC-FID (Agilent 7890B) are analyzed.Chromatographic column (polymethyl siloxane
30m × 0.32mm × 1 μm) flow rate of carrier gas 30mL/min, column temperature, air inlet and detector temperature are respectively 180,200 and 250
℃。
The catalyst prepared using embodiment 1- embodiments 4 is catalysis material, activity rating such as following table
In conclusion the present invention has the following advantages：
1. the present invention prepares porous polymer solid acid, there is larger BET surface area, be layered the acid of nano-pore and enhancing
Intensity.Its structure-controllable simultaneously, it is easily operated, it can be mass-produced, have broad application prospects.
2. the present invention, which prepares porous polymer solid acid, has excellent catalytic activity, and significantly improves alkynes hydration
Generate the hydrogenation of the reusability and amine and phenylacetylene of ketone, even better than Amberlyst 15, phosphotungstic acid and sulfuric acid.
A kind of reaction process of green is provided for alkynes hydration reaction.
It is understood that above with respect to the specific descriptions of the present invention, it is merely to illustrate the present invention and is not limited to this
Technical solution described in inventive embodiments.It will be understood by those of ordinary skill in the art that still can be carried out to the present invention
Modification or equivalent replacement, to reach identical technique effect；As long as meet use needs, all protection scope of the present invention it
It is interior.
Claims (9)
1. a kind of porous polymer solid acid catalyst for alkynes hydration reaction, it is characterised in that：The solid acid is with fat
Class is solvent, passes through divinylbenzene (DVB), 1- vinyl imidazoles (vim) or 4-vinylpridine (VP), p styrene sulfonic acid
Sodium carries out solvent heat copolymerization, then reacts to form quaternary ammonium salt with 1,3-propane sultone, by carrying out ion friendship with acid
It changes, ultimately forms porous polymer solid acid.
2. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 1, feature
It is：The preparation method of the porous polymer solid acid catalyst is in accordance with the following steps：
Step 1, azodiisobutyronitrile is dissolved in lipid solvent, divinylbenzene is then added, be stirring evenly and then adding into 1-
Vinyl imidazole or 4-vinylpridine carry out high-temperature solvent thermal response, obtain mixed reaction solution；
Step 2, by mixed reaction solution room temperature slow evaporation until solvent volatilize completely, obtain carrier material；
Step 3, carrier is put into toluene, 1,3-propane sultone is then added and carries out the quaternized processing of high temperature, after filtering
It is washed using ethyl alcohol, vacuum drying obtains sediment；
Step 4, sediment is put into the toluene solvant of acid and is handled, then dichloromethane is used to wash, vacuum drying obtains more
Pore polymer solid acid.
3. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：Lipid solvent in the step 1 uses Ethyl formate, one or more of methyl acetate or ethyl acetate.
4. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：The reaction temperature of the high-temperature solvent thermal response in the step 1 is 80-160 DEG C, the mixing time 6- of the stirring
36h。
5. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：Mass concentration of the sediment in toluene solvant in the step 3 is 25-50g/L, and the quaternized processing of high temperature is adopted
With being handled under room temperature, temperature is 100-160 DEG C, processing time 12-36h, and the vacuum drying temperature after the ethyl alcohol washing is
80-120 DEG C, drying time 12-36h.
6. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：Acid in the step 4 uses HSO3CF3Or H2SO4；The CH2Cl2Vacuum drying temperature after washing is 100-160
DEG C, drying time 24-48h.
7. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：Evaporation in the step 2 carries out under normal pressure.
8. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 2, feature
It is：Catalyst in the step 4 is used for alkynes hydration reaction.
9. a kind of porous polymer solid acid catalyst for alkynes hydration reaction according to claim 8, feature
It is：The method of the alkynes hydration reaction is as follows：By catalyst and phenylacetylene, the mixed solution of deionized water and trifluoroethanol
It is reacted in microwave tube, then utilizes its product of chromatography.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909389A (en) * | 2020-08-06 | 2020-11-10 | 山东师范大学 | Covalent organic framework material and preparation method and application thereof |
| CN112246282A (en) * | 2020-11-05 | 2021-01-22 | 中国科学院兰州化学物理研究所苏州研究院 | Acidic porous polymer catalyst, and preparation method and application thereof |
| CN112808310A (en) * | 2019-11-18 | 2021-05-18 | 六盘水师范学院 | Amphiphilic organic porous polymer solid acid catalyst and preparation method and application thereof |
| CN115318338A (en) * | 2022-07-19 | 2022-11-11 | 武汉理工大学 | Porous polymer-based ionic liquid solid acid catalyst and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103706396A (en) * | 2014-01-06 | 2014-04-09 | 北京化工大学 | Preparation method of polydivinylbenzene-ionic liquid-polyacid catalysts and application thereof |
| CN105753668A (en) * | 2016-03-11 | 2016-07-13 | 江南大学 | Oxygen-participative alkyne green oxidative carbonylation reaction under promotion effects of visible light |
| CN106854159A (en) * | 2015-12-09 | 2017-06-16 | 中国科学院大连化学物理研究所 | A kind of method of phenylacetylene carbonyl compound into unsaturated aromatic ester |
| CN107297222A (en) * | 2017-06-14 | 2017-10-27 | 东南大学 | A kind of preparation of poly ion liquid solid acid catalyst and its application process |
-
2018
- 2018-05-24 CN CN201810505342.7A patent/CN108620124A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103706396A (en) * | 2014-01-06 | 2014-04-09 | 北京化工大学 | Preparation method of polydivinylbenzene-ionic liquid-polyacid catalysts and application thereof |
| CN106854159A (en) * | 2015-12-09 | 2017-06-16 | 中国科学院大连化学物理研究所 | A kind of method of phenylacetylene carbonyl compound into unsaturated aromatic ester |
| CN105753668A (en) * | 2016-03-11 | 2016-07-13 | 江南大学 | Oxygen-participative alkyne green oxidative carbonylation reaction under promotion effects of visible light |
| CN107297222A (en) * | 2017-06-14 | 2017-10-27 | 东南大学 | A kind of preparation of poly ion liquid solid acid catalyst and its application process |
Non-Patent Citations (3)
| Title |
|---|
| FUJIAN LIU: "Transesterification Catalyzed by Ionic Liquids on Superhydrophobic Mesoporous Polymers: Heterogeneous Catalysts That Are Faster than Homogeneous Catalysts", 《J. AM. CHEM. SOC.》 * |
| RAJKUMAR KORE: "Hydration of alkynes using Bronsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4", 《JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL》 * |
| WENBO LIU: "Metal-Free Markovnikov-Type Alkyne Hydration under Mild Conditions", 《ORG. LETT.》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112808310A (en) * | 2019-11-18 | 2021-05-18 | 六盘水师范学院 | Amphiphilic organic porous polymer solid acid catalyst and preparation method and application thereof |
| CN112808310B (en) * | 2019-11-18 | 2022-09-06 | 六盘水师范学院 | Amphiphilic organic porous polymer solid acid catalyst and preparation method and application thereof |
| CN111909389A (en) * | 2020-08-06 | 2020-11-10 | 山东师范大学 | Covalent organic framework material and preparation method and application thereof |
| CN111909389B (en) * | 2020-08-06 | 2022-04-15 | 山东师范大学 | Covalent organic framework material and preparation method and application thereof |
| CN112246282A (en) * | 2020-11-05 | 2021-01-22 | 中国科学院兰州化学物理研究所苏州研究院 | Acidic porous polymer catalyst, and preparation method and application thereof |
| CN115318338A (en) * | 2022-07-19 | 2022-11-11 | 武汉理工大学 | Porous polymer-based ionic liquid solid acid catalyst and preparation method and application thereof |
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Application publication date: 20181009 |