CN108479849A - The solid-loaded ionic-liquid catalyst and preparation method and application of synthesis of alkyl diphenyl ether - Google Patents
The solid-loaded ionic-liquid catalyst and preparation method and application of synthesis of alkyl diphenyl ether Download PDFInfo
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- CN108479849A CN108479849A CN201810131340.6A CN201810131340A CN108479849A CN 108479849 A CN108479849 A CN 108479849A CN 201810131340 A CN201810131340 A CN 201810131340A CN 108479849 A CN108479849 A CN 108479849A
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- diphenyl ether
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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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
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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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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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
Abstract
A kind of solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether, which is adsorbed in by ion liquid of quaternaries on atlapulgite, to be obtained, it is that atlapulgite is roasted into 36 h in 450 650 DEG C, it is added it in ion liquid of quaternaries after cooling, in 50 120 DEG C of temperature and has N2Under protective condition, 25 h are stirred, sealing is aged 12 24 h at room temperature, filters out solid matter, in 100 120 DEG C of dry 2 4h to get to solid-loaded ionic-liquid catalyst.The present invention has preparation process simple, and reaction condition is mild, corrodes small, cheap, high conversion rate, the segregative advantage of catalyst to equipment.
Description
Technical field
The present invention relates to a kind of solid-loaded ionic-liquid catalysts and preparation method and application of synthesis of alkyl diphenyl ether.
Background technology
Alkyl diphenyl ether has excellent low-temperature viscosity profiles, lower solidification point and excellent thermal stability, can make
The medium of plasticizer, lubricating oil and transformer for varnish, resin etc. etc. uses.In addition to this, alkyl diphenyl ether by sulfonation,
It is a kind of double type anion surfactant haveing excellent performance to neutralize the p alkylphenylaceticacid obtained later.It has
Higher surface-active, excellent water-soluble, preferable resistance to acid and alkali and compound property, can be with high temperature resistance, hard water resistance.With compared with
Strong application value is widely used in the fields such as daily use chemicals, emulsion polymerization, industry cleaning link and tertiary oil recovery.
The alkylation catalyst of common synthesis of alkyl diphenyl ether has anhydrous Aluminum chloride, boron fluoride and sulfuric acid etc., wherein with
The active highest of anhydrous Aluminum chloride.Although these traditional alkylating reagents have many advantages, such as cheap price, higher yield,
But it is higher to equipment requirement, environmental pollution is serious.People, which study more novel alkylation catalyst, at present mainly solid
Super acids, cation exchange resin and ionic-liquid catalyst etc..Solid super-strong acid as a kind of novel catalyst have compared with
The features such as good catalytic activity and small environmental pollution, but for liquid catalyst reaction, it is not easy to react relatively
And cost is higher.And although cation exchange resin shows more excellent performance, but its thermal stability hinders work
Industry metaplasia is produced.Ionic liquid has the characteristics that non-corrosive, not volatile, nontoxic and catalytic activity is high, receives extensive pass
Note.Such catalyst has been used in the alkylated reaction of alkene and diphenyl ether, as document " Determination of Acidity of ionic liquid and
Its diphenyl ether/laurylene alkylated reaction being catalyzed " (catalysis journal, 2004,25 (1))；Patent CN 1524839A use alkyl
Imidazoles, alkylammonium salt and metal halide synthetic are catalyst, and catalytic alkylation reagent is reacted with diphenyl ether prepares alkyl two
Phenylate.Ionic-liquid catalyst has many advantages, such as without notable vapour pressure, environmentally friendly, catalytic activity is high.But there is also certainly
Body problem, such as catalyst amount is big, expensive, reaction product is difficult to detach with catalyst system.
Solid-loaded ionic-liquid catalyst is that either chemical method will be ionic liquid loaded to organic or nothing by physics
On machine material.Such catalyst is merged the high-specific surface area of support materials and ionic liquid good dissolubility, not only
The dosage of catalysis reaction intermediate ion liquid is considerably reduced, and the activity and selectivity of catalyst is improved,
More easily realize the separation of catalyst and product.Solid-loaded ionic-liquid catalyst has been used to catalytic alkylation reaction, such as document
“Supported Ionic Liquid Catalysis-A New Concept for Homogeneous
Hydroformylation Catalysis”(JACS 2002, 124(44):12932-3.), " Immobilised Ionic
Liquids as Lewis Acid Catalysts for the Alkylation of Aromatic Compounds with
Dodecene”(J. Catal., 2000, 196(1):86-94.) etc.；Patent CN 101049575A and CN 1387461A are public
It has opened one kind and ionic liquid is linked with carrier by the solid-loaded ionic-liquid catalyst to be formed in the form of covalent bond by silanizing agent,
The catalyst can be used for Friedel-Crafts reaction.But such solid-loaded ionic-liquid synthesis technology is complex and catalytic activity
It is relatively low, it is unfavorable for industrialized production.
Invention content
The object of the present invention is to provide it is a kind of it is at low cost, preparation process is simple, catalytic activity is high, catalyst amount is few, easy
The small solid-loaded ionic-liquid catalyst and preparation method and application for synthesis of alkyl diphenyl ether is corroded equipment in separation.
The solid-loaded ionic-liquid catalyst of the present invention, which is adsorbed in by ion liquid of quaternaries on atlapulgite, to be obtained,
Specific preparation method includes the following steps：
Atlapulgite is roasted into 3-6 h in 450-650 DEG C, is added it in ion liquid of quaternaries after cooling, in temperature
50-120 DEG C and there is N2 Under protective condition, 2-5 h are stirred, sealing is aged 12-24 h at room temperature, filters out solid matter, in
100-120 DEG C of dry 2-4h is to get to solid-loaded ionic-liquid catalyst.
The application of the solid-loaded ionic-liquid catalyst of the synthesis of alkyl diphenyl ether of the present invention, includes the following steps：
It is 1 in molar ratio by diphenyl ether and alkene:0.2-12 be added reactor in, then by synthesis of alkyl diphenyl ether it is immobilized from
Sub- liquid catalyst is added in reactant, and 2-4h is stirred to react at 70-160 DEG C, and entire reaction is in N2 Under protective condition into
Row, system is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, after supernatant liquid is washed with distilled water three times, warp
The complete raw material of unreacted is removed after vacuum distillation obtains alkyl diphenyl ether.
Ion liquid of quaternaries as described above is by quaternary ammonium salt (ethylamine hydrochloride EtNH3Cl, diethylamine hydrochloride
Et2NH2Cl, triethylamine hydrochloride Et3NHCl or trimethylamine hydrochloride Me3NHCl) with metal halide (AlCl3、ZnCl2Or FeCl3)
Synthesis, structure EtNH3Cl-AlCl3、Et2NH2Cl-AlCl3、Et3NHCl-AlCl3、Me3NHCl-AlCl3、Et3NHCl-
ZnCl2Or Et3NHCl-FeCl3Deng.Specific preparation method is according to document " Et3NHCl-AlCl3It is catalyzed benzene and 1- benzene alkane
The research of glycosylation reaction mechanism " (Chinese science:Chemistry, 2010 (5):461-466).
Atlapulgite as described above is 1 with ion liquid of quaternaries mass ratio:4-8.
The solid-loaded ionic-liquid catalyst dosage of synthesis of alkyl diphenyl ether as described above is alkene and diphenyl ether gross mass
0.5%-5%.
Alkene as described above is C6 -C24Linear chain or branched chain alkene.
The present invention provides a kind of solid-loaded ionic-liquid catalyst and preparation method and application of synthesis of alkyl diphenyl ether, tools
Have that preparation process is simple, reaction condition is mild, it is easily separated etc. excellent to corrode small, cheap, high conversion rate, catalyst to equipment
Point.
Specific implementation mode
Following instance is intended to further illustrate the present invention, without limiting the present invention.
Embodiment 1
（1）EtNH3Cl-AlCl3The preparation of ionic liquid
0.5mol ethylamine hydrochlorides are added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
EtNH3Cl is less than 50 DEG C, by the AlCl of 1mol with temperature controlled water baths3It is added portionwise in flask by quantitative funnel.It waits for
AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to EtNH3Cl-AlCl3Ionic liquid
Body.
（2）The preparation of catalyst
100g atlapulgites are roasted into 6h in 450 DEG C, are added it to equipped with 400g EtNH after cooling3Cl-AlCl3Ionic liquid
In the four-hole bottle of body.In 120 DEG C of temperature and there is N2 Under protective condition, 2h is stirred.Sealing is aged for 24 hours at room temperature.Filter out solid
Substance, dry 2h is to get to solid-loaded ionic-liquid catalyst in 100 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C6ɑ-alkene is 1 in molar ratio:2 are added in four-hole bottles, then by alkene and diphenyl ether gross mass
0.5% catalyst is added in reactant.Reaction mixture stirs 2h at being 160 DEG C in temperature, and entire reaction is in N2 Ceiling
It is carried out under part.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water three
After secondary, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtains alkyl diphenyl ether.Product efficient liquid phase
Chromatography detects, and diphenyl ether conversion ratio is 90.4%.
Embodiment 2
（1）Et2NH2Cl-AlCl3The preparation of ionic liquid
0.5mol diethylamine hydrochloric acid is added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
Salt Et2NH2Cl is less than 50 DEG C, by the AlCl of 1mol with temperature controlled water baths3It is added portionwise in flask by quantitative funnel.
Wait for AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to Et2NH2Cl-AlCl3From
Sub- liquid.
（2）The preparation of catalyst
100g atlapulgites are roasted into 4h in 550 DEG C, are added it to equipped with 600g Et after cooling2NH2Cl-AlCl3Ionic liquid
In the four-hole bottle of body, in 90 DEG C of temperature and there is N2 Under protective condition, 3h is stirred.It is aged 12h at room temperature.Solid matter is filtered out,
Dry 4h is to get to solid-loaded ionic-liquid catalyst in 120 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C12 ɑ-alkene is 1 in molar ratio:0.2 is added in four-hole bottle, then by alkene and diphenyl ether gross mass
2.0% catalyst is added in reactant.Reaction mixture stirs 3h at being 90 DEG C in temperature, and entire reaction is in N2 Ceiling
It is carried out under part.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water three
After secondary, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtains alkyl diphenyl ether.Product efficient liquid phase
Chromatography detects, C12 ɑ-olefin conversion is 88.4%.
Embodiment 3
（1）Et3NHCl-AlCl3The preparation of ionic liquid
0.5mol triethylamine hydrochlorides are added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
Et3NHCl is less than 50 DEG C, by the AlCl of 1mol with temperature controlled water baths3It is added portionwise in flask by quantitative funnel.It waits for
AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to Et3NHCl-AlCl3Ionic liquid
Body.
（2）The preparation of catalyst
100g atlapulgites are roasted into 3h in 650 DEG C, are added it to equipped with 800g Et after cooling3NHCl-AlCl3Ionic liquid
In the four-hole bottle of body, in temperature 50 C and there is N2 Under protective condition, 5h is stirred.After sealing, it is aged at room temperature for 24 hours.It filters out solid
Body substance, dry 3h is to get to solid-loaded ionic-liquid catalyst in 110 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C24 ɑ-alkene is 1 in molar ratio:12 are added in four-hole bottles, then by alkene and diphenyl ether gross mass
5% catalyst is added in reactant.Reaction mixture stirs 4h at being 70 DEG C in temperature, and entire reaction is in N2 Protective condition
Lower progress.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water three times
Afterwards, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtain alkyl diphenyl ether.Product high-efficient liquid phase color
Spectrum detection, diphenyl ether conversion ratio are 87.3%.
Embodiment 4
（1）Me3NHCl-AlCl3The preparation of ionic liquid
0.5mol trimethylamine hydrochlorides are added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
Me3NHCl is less than 50 DEG C, by the AlCl of 1mol with temperature controlled water baths3It is added portionwise in flask by quantitative funnel.It waits for
AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to Me3NHCl-AlCl3Ionic liquid
Body.
（2）The preparation of catalyst
100g atlapulgites are roasted into 4h in 450 DEG C, are added it to equipped with 600g Me after cooling3NHCl-AlCl3Ionic liquid
In the four-hole bottle of body, in 100 DEG C of temperature and there is N2 Under protective condition, 3h is stirred.After sealing, it is aged at room temperature for 24 hours.It filters out solid
Body substance, dry 2h is to get to solid-loaded ionic-liquid catalyst in 120 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C10 Branched-chain alkene is 1 in molar ratio:8 are added in four-hole bottles, then by alkene and diphenyl ether gross mass
3.0% catalyst is added in reactant.Reaction mixture stirs 3h at being 90 DEG C in temperature, and entire reaction is in N2 Ceiling
It is carried out under part.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water three
After secondary, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtains alkyl diphenyl ether.Product efficient liquid phase
Chromatography detects, and diphenyl ether conversion ratio is 93.2%.
Embodiment 5
（1）Et3NHCl-ZnCl2The preparation of ionic-liquid catalyst
0.5mol triethylamine hydrochloride salt is added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
Et3NHCl is less than 50 DEG C, by the ZnCl of 1mol with temperature controlled water baths2It is added portionwise in flask by quantitative funnel.It waits for
AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to Et3NHCl-ZnCl2Ionic liquid
Body.
（2）The preparation of catalyst
100g atlapulgites are roasted into 5h in 550 DEG C, are added it to equipped with 500g Et after cooling3NHCl-ZnCl2Ionic liquid
In the four-hole bottle of body, in 110 DEG C of temperature and there is N2 Under protective condition, 4h is stirred.After sealing, it is aged 18h at room temperature.It filters out solid
Body substance, dry 4h is to get to solid-loaded ionic-liquid catalyst in 120 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C16Branched-chain alkene is 1 in molar ratio:4 are added in four-hole bottles, then by alkene and diphenyl ether gross mass
4.0% catalyst is added in reactant.Reaction mixture stirs 4h at being 70 DEG C in temperature, and entire reaction is in N2 Ceiling
It is carried out under part.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water three
After secondary, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtains alkyl diphenyl ether.Product efficient liquid phase
Chromatography detects, and diphenyl ether conversion ratio is 84.2%.
Embodiment 6
（1）Et3NHCl-FeCl3The preparation of ionic-liquid catalyst
0.5mol triethylamine hydrochloride salt is added in the round-bottomed flask equipped with condenser, constant pressure funnel and mechanical stirring device
Et3NHCl is less than 50 DEG C, by the FeCl of 1mol with temperature controlled water baths3It is added portionwise in flask by quantitative funnel.It waits for
AlCl3After being all added, bath temperature is adjusted to 80 DEG C, in N2 The lower stirring 5h of protection is to get to Et3NHCl-FeCl3Ionic liquid
Body.
（2）The preparation of catalyst
100g atlapulgites are roasted into 2h in 650 DEG C, are added it to equipped with 700g Et after cooling3NHCl-FeCl3Ionic liquid
In the four-hole bottle of body, in 100 DEG C of temperature and there is N2 Under protective condition, 3h is stirred.After sealing, it is aged at room temperature for 24 hours.It filters out solid
Body substance, dry 2h is to get to solid-loaded ionic-liquid catalyst in 120 DEG C of baking ovens.
（3）The synthesis of alkyl diphenyl ether
By diphenyl ether and C14Branched-chain alkene is 1 in molar ratio:0.8 is added in four-hole bottle, then by alkene and diphenyl ether gross mass
2.5% catalyst be added in reactant.Reaction mixture stirs 3h at being 120 DEG C in temperature, and entire reaction is in N2 Protection
Under the conditions of carry out.System is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, and supernatant liquid is washed with distilled water
After three times, unreacted complete alkene and diphenyl ether are removed after vacuum distillation, finally obtains alkyl diphenyl ether.The efficient liquid of product
Phase chromatography detects, C14Branched-chain alkene conversion ratio is 82.1%.
Claims (7)
1. a kind of solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether, it is characterised in that catalyst is by quaternary ammonium salt ion
Liquid adsorption is in obtaining on atlapulgite.
2. a kind of solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as described in claim 1 has preparation method, special
Sign is to include the following steps：
Atlapulgite is roasted into 3-6 h in 450-650 DEG C, is added it in ion liquid of quaternaries after cooling, in temperature
50-120 DEG C and there is N2 Under protective condition, 2-5 h are stirred, sealing is aged 12-24 h at room temperature, filters out solid matter, in
100-120 DEG C of dry 2-4h is to get to solid-loaded ionic-liquid catalyst.
3. a kind of preparation method of the solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as claimed in claim 2, special
Sign is that the ion liquid of quaternaries is EtNH3Cl-AlCl3、Et2NH2Cl-AlCl3、Et3NHCl-AlCl3、
Me3NHCl-AlCl3、Et3NHCl-ZnCl2Or Et3NHCl-FeCl3。
4. a kind of solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as claimed in claim 2 has preparation method, special
Sign is that the atlapulgite and ion liquid of quaternaries mass ratio are 1:4-8.
5. a kind of application of the solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as described in claim 1, feature exist
In including the following steps：
It is 1 in molar ratio by diphenyl ether and alkene:0.2-12 be added reactor in, then by synthesis of alkyl diphenyl ether it is immobilized from
Sub- liquid catalyst is added in reactant, and 2-4h is stirred to react at 70-160 DEG C, and entire reaction is in N2 Under protective condition into
Row, system is divided into liquid-solid two layers after reaction, and decompression, which filters, removes solid, after supernatant liquid is washed with distilled water three times, warp
The complete raw material of unreacted is removed after vacuum distillation obtains alkyl diphenyl ether.
6. a kind of application of the solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as claimed in claim 5, feature exist
In the 0.5%-5% that the solid-loaded ionic-liquid catalyst dosage of the synthesis of alkyl diphenyl ether is alkene and diphenyl ether gross mass.
7. a kind of application of the solid-loaded ionic-liquid catalyst of synthesis of alkyl diphenyl ether as claimed in claim 5, feature exist
In the alkene be C6 -C24Linear chain or branched chain alkene.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115106125A (en) * | 2022-08-08 | 2022-09-27 | 中国石油大学(华东) | Preparation method and application of solid acid catalyst loaded with ionic liquid |
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2018
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| CN1524839A (en) * | 2003-02-27 | 2004-09-01 | 北京大学 | Method for synthesizing linear alkyl diphenyl ether |
| CN1594253A (en) * | 2003-09-10 | 2005-03-16 | 大连化工研究设计院 | Synthesis method of long carbon chain alkyl diphenyl ether/long carbon chain alkyl substituted diphenyl ether |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115106125A (en) * | 2022-08-08 | 2022-09-27 | 中国石油大学(华东) | Preparation method and application of solid acid catalyst loaded with ionic liquid |
| CN115106125B (en) * | 2022-08-08 | 2023-09-05 | 中国石油大学(华东) | Preparation method and application of ionic liquid-loaded solid acid catalyst |
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Application publication date: 20180904 |