CN108048130A - It is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the method for phenolic compound hydrogenation deoxidation - Google Patents
It is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the method for phenolic compound hydrogenation deoxidation Download PDFInfo
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- B01J31/22—Organic complexes
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- B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- B01J37/0201—Impregnation
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/646—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of aromatic or heteroaromatic rings
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
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- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
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Abstract
It is a kind of to use 100 (Fe) SO of support type MIL3Na catalyst belongs to technical field of catalytic hydrogenation to the method for phenolic compound hydrogenation deoxidation.Specifically include following steps：(1) 100 (Fe) SO of support type MIL are synthesized3Na catalyst：MIL 100 (Fe) is first synthesized, then prepares MIL 100 (Fe) SO3Na carriers finally obtain support type MIL 100 (Fe) SO3Na catalyst；(2) by support type MIL 100 (Fe) SO3Na catalyst and phenolic compound are put into batch reactor, and hydrogenation deoxidation reaction is carried out under the conditions of 2~4MPa of hydrogen partial pressure, 100~250 DEG C of temperature, finally obtains hydrogenation deoxidation product.Catalyst made from this method has Superhydrophilic, and large specific surface area, tenor is high, and feed stock conversion is high, good product selectivity, stable in catalytic performance.
Description
(1) technical field
The present invention provides a kind of using support type MIL-100 (Fe)-SO3Na catalyst is to phenolic compound hydrogenation deoxidation
Method belongs to technical field of catalytic hydrogenation.
(2) background technology
MIL-100 is that one kind of French Antoine Lavoisier laboratory Ferey et al. synthesis has larger aperture and bigger serface
Metal-organic framework (MOFs) material, its aperture of document report be 2.5~3.0nm, specific surface area 3100m2/ g, pore volume
For 1.16cm3/g.Due to its excellent porous material characteristic, there is very high researching value in absorption, catalysis etc..MIL-
100 (Fe) are the ions centered on Fe, and benzenetricarboxylic acid is the porous material of ligand.
One of most significant feature of MOFs materials be exactly organic ligand in its pore passage structure easily by chemical method into
Row modification, the present invention carries out sulfonic acid funtionalized modification to MIL-100 (Fe), so as to obtain containing different sulfonic acid group quantity
MIL-101 (Fe) is used as carrier, and carried noble metal (such as ruthenium, rhodium, palladium, platinum etc.) obtains support type MIL-100 (Fe)-SO3Na
Catalyst can be used for carrying out hydrogenation deoxidation to biological oil base phenolic compound (phenol, guaiacol, cresols etc.).
(3) content of the invention
The present invention is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the side of phenolic compound hydrogenation deoxidation
Method specifically includes following steps：
(1) deionized water of the source of iron of 5~9mmol, the organic ligand of 2~5mmol and 10~50ml is weighed, 20~30
10~50min is stirred under the conditions of DEG C to dissolving, obtains mixed solution.
Source of iron described in step (1) is ferric nitrate, one kind in iron chloride, ferric acetyl acetonade；Organic ligand is equal benzene
One kind in tricarboxylic acid, trimethyl trimesate.
(2) by step (1) obtained by mixed solution, at 100~150 DEG C after 5~10h of hydro-thermal process, carry out at centrifugation
Reason, obtains sediment, then washs 3~5 times respectively with dimethylformamide, absolute ethyl alcohol, ammonium fluoride and deionized water, finally
5~12h is dried in vacuo at 50~100 DEG C to get to MIL-100 (Fe).
(3) MIL-100 (Fe) that step (2) obtains is put into the dichloromethane of 10~50ml, adds and reenter 0.1~0.3g
Chlorosulfonic acid, stir 10~50min, then filter, washed respectively 3~5 times with deionized water and acetone, finally 50~100
5~12h is dried in vacuo at DEG C to get to MIL-100 (Fe)-SO3Na carriers.
(4) MIL-100 (Fe)-SO for obtaining precious metal salt solution with step (3) is immersed in after water dissolution3Na carriers
On, load capacity is 1~3%, is then placed in baking oven dry 8~for 24 hours, and temperature is 80~120 DEG C, finally 10% hydrogen-
Reductase 12~4h in argon gas, temperature are 350~450 DEG C, obtain support type MIL-100 (Fe)-SO3Na catalyst.
Precious metal salt described in step (4) is nitric acid ruthenium, one kind in radium chloride, palladium nitrate, platinum chloride.
Support type MIL-100 (Fe)-SO3Na catalyst can be used for the hydrogenation deoxidation of phenolic compound to react, and method is：
By support type MIL-100 (Fe)-SO3Na catalyst and be put into phenolic compound in batch reactor, Hydrogen Vapor Pressure 2~
4MPa carries out hydrogenation deoxidation under the conditions of 100~250 DEG C of temperature and reacts 1~10h, finally obtains in phenolic compound hydrogenation deoxidation
Product.
It is recited above in phenolic compound be phenol, guaiacol, one kind in cresols.
The advantage of the invention is that：
1st, it is proposed by the present invention a kind of using support type MIL-100 (Fe)-SO3Na catalyst is hydrogenated with phenolic compound de-
The method of oxygen, support type MIL-100 (the Fe)-SO prepared in this method3Na catalyst has large specific surface area, tenor
The advantages that height, multiple aperture is distributed.
2nd, it is proposed by the present invention a kind of using support type MIL-100 (Fe)-SO3Na catalyst is hydrogenated with phenolic compound de-
The method of oxygen, support type MIL-100 (Fe)-SO that this method obtains3Na catalyst has Superhydrophilic, and catalytic activity is good,
Feed stock conversion is high, and selectivity of product is high, stable in catalytic performance.
(4) illustrate
Fig. 1：It is proposed by the present invention a kind of using support type MIL-100 (Fe)-SO3Na catalyst is hydrogenated with phenolic compound
The process flow chart of the method for deoxidation.
(5) specific embodiment
The technical characterstic of the present invention is described in detail below in conjunction with the drawings and specific embodiments, as shown in Figure 1.
Embodiment 1：
The present invention is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the side of phenolic compound hydrogenation deoxidation
Method specifically includes following steps：
(1) deionized water of the source of iron of 7mmol, the organic ligand of 3.5mmol and 30ml is weighed, is stirred under the conditions of 25 DEG C
30min obtains mixed solution to dissolving.
Source of iron described in step (1) is ferric nitrate；Organic ligand is trimesic acid.
(2) by step (1) obtained by mixed solution, at 120 DEG C after hydro-thermal process 7h, carry out centrifugal treating, sunk
Then starch washs 4 times, finally the vacuum at 70 DEG C respectively with dimethylformamide, absolute ethyl alcohol, ammonium fluoride and deionized water
Dry 8h is to get to MIL-100 (Fe).
(3) MIL-100 (Fe) that step (2) obtains is put into the dichloromethane of 30ml, adds the chlorosulfonic acid for reentering 0.2g,
Stir 30min, then filter, 45 times are washed respectively with deionized water and acetone, be finally dried in vacuo at 70 DEG C 8h to get to
MIL-100(Fe)-SO3Na carriers.
(4) MIL-100 (Fe)-SO for obtaining precious metal salt solution with step (3) is immersed in after water dissolution3Na carriers
On, load capacity 2% is then placed in baking oven dry 12h, and temperature is 100 DEG C, is finally reduced in 10% hydrogen-argon
3h, temperature are 400 DEG C, obtain support type MIL-100 (Fe)-SO3Na catalyst.
Precious metal salt described in step (4) is nitric acid ruthenium.
Support type MIL-100 (Fe)-SO3Na catalyst can be used for the hydrogenation deoxidation of phenolic compound to react, and method is：
By support type MIL-100 (Fe)-SO3It Na catalyst and is put into phenolic compound in batch reactor, in Hydrogen Vapor Pressure
3MPa carries out hydrogenation deoxidation reaction 5h under the conditions of 150 DEG C of temperature, finally obtains in phenolic compound hydrogenation deoxidation product.
It is recited above in phenolic compound be phenol.
The result shows that support type MIL-100 (Fe)-SO3The conversion ratio of Na catalyst Pyrogentisinic Acids is 97%, the selection of product
Property is 96%, and catalytic effect is notable.
Embodiment 2：
The present invention is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the side of phenolic compound hydrogenation deoxidation
Method specifically includes following steps：
(1) deionized water of the source of iron of 5mmol, the organic ligand of 2mmol and 10ml is weighed, is stirred under the conditions of 20 DEG C
10min obtains mixed solution to dissolving.
Source of iron described in step (1) is iron chloride；Organic ligand is trimesic acid.
(2) by step (1) obtained by mixed solution, at 100 DEG C after hydro-thermal process 10h, carry out centrifugal treating, sunk
Then starch washs 3 times, finally the vacuum at 50 DEG C respectively with dimethylformamide, absolute ethyl alcohol, ammonium fluoride and deionized water
Dry 12h is to get to MIL-100 (Fe).
(3) MIL-100 (Fe) that step (2) obtains is put into the dichloromethane of 10ml, adds the chlorosulfonic acid for reentering 0.1g,
Stir 10min, then filter, 3 times are washed respectively with deionized water and acetone, be finally dried in vacuo at 50 DEG C 12h to get to
MIL-100(Fe)-SO3Na carriers.
(4) MIL-100 (Fe)-SO for obtaining precious metal salt solution with step (3) is immersed in after water dissolution3Na carriers
On, load capacity 1% is then placed in baking oven dry 8h, and temperature is 120 DEG C, is finally reduced in 10% hydrogen-argon
4h, temperature are 350 DEG C, obtain support type MIL-100 (Fe)-SO3Na catalyst.
Precious metal salt described in step (4) is radium chloride.
Support type MIL-100 (Fe)-SO3Na catalyst can be used for the hydrogenation deoxidation of phenolic compound to react, and method is：
By support type MIL-100 (Fe)-SO3It Na catalyst and is put into phenolic compound in batch reactor, in Hydrogen Vapor Pressure
2MPa carries out hydrogenation deoxidation reaction 1h under the conditions of 250 DEG C of temperature, finally obtains in phenolic compound hydrogenation deoxidation product.
It is recited above in phenolic compound be guaiacol.
The result shows that support type MIL-100 (Fe)-SO3Na catalyst is 94% to the conversion ratio of guaiacol, product
Selectivity is 95%, and catalytic effect is notable.
Embodiment 3：
The present invention is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the side of phenolic compound hydrogenation deoxidation
Method specifically includes following steps：
(1) deionized water of the source of iron of 9mmol, the organic ligand of 5mmol and 50ml is weighed, is stirred under the conditions of 30 DEG C
50min obtains mixed solution to dissolving.
Source of iron described in step (1) is ferric acetyl acetonade；Organic ligand is trimethyl trimesate.
(2) by step (1) obtained by mixed solution, at 150 DEG C after hydro-thermal process 5h, carry out centrifugal treating, sunk
Then starch is washed 5 times respectively with dimethylformamide, absolute ethyl alcohol, ammonium fluoride and deionized water, finally true at 100 DEG C
The dry 5h of sky is to get to MIL-100 (Fe).
(3) MIL-100 (Fe) that step (2) obtains is put into the dichloromethane of 50ml, adds the chlorosulfonic acid for reentering 0.3g,
Stir 50min, then filter, 5 times are washed respectively with deionized water and acetone, be finally dried in vacuo at 100 DEG C 5h to get to
MIL-100(Fe)-SO3Na carriers.
(4) MIL-100 (Fe)-SO for obtaining precious metal salt solution with step (3) is immersed in after water dissolution3Na carriers
On, load capacity 3%, being then placed in drying in baking oven, for 24 hours, temperature is 80 DEG C, is finally reduced in 10% hydrogen-argon
2h, temperature are 450 DEG C, obtain support type MIL-100 (Fe)-SO3Na catalyst.
Precious metal salt described in step (4) is palladium nitrate.
Support type MIL-100 (Fe)-SO3Na catalyst can be used for the hydrogenation deoxidation of phenolic compound to react, and method is：
By support type MIL-100 (Fe)-SO3It Na catalyst and is put into phenolic compound in batch reactor, in Hydrogen Vapor Pressure
4MPa carries out hydrogenation deoxidation reaction 10h under the conditions of 100 DEG C of temperature, finally obtains in phenolic compound hydrogenation deoxidation product.
It is recited above in phenolic compound be cresols.
The result shows that support type MIL-100 (Fe)-SO3The conversion ratio of Na catalyst paracresol is 91%, the selection of product
Property is 90%, and catalytic effect is notable.
Claims (4)
1. a kind of use support type MIL-100 (Fe)-SO3Na catalyst exists to the method for phenolic compound hydrogenation deoxidation, feature
In this method specifically includes following steps：
(1) deionized water of the source of iron of 5~9mmol, the organic ligand of 2~5mmol and 10~50ml is weighed, in 20~30 DEG C of items
10~50min is stirred under part to dissolving, obtains mixed solution；
(2) by step (1) obtained by mixed solution, at 100~150 DEG C after 5~10h of hydro-thermal process, carry out centrifugal treating, obtain
To sediment, then washed respectively 3~5 times with dimethylformamide, absolute ethyl alcohol, ammonium fluoride and deionized water, finally 50
5~12h is dried in vacuo at~100 DEG C to get to MIL-100 (Fe)；
(3) MIL-100 (Fe) that step (2) obtains is put into the dichloromethane of 10~50ml, adds the chlorine for reentering 0.1~0.3g
Sulfonic acid stirs 10~50min, then filters, washed respectively 3~5 times with deionized water and acetone, finally at 50~100 DEG C
5~12h is dried in vacuo to get to MIL-100 (Fe)-SO3Na carriers；
(4) MIL-100 (Fe)-SO for obtaining precious metal salt solution with step (3) is immersed in after water dissolution3On Na carriers, load
It measures as 1~3%, dry 8 are then placed in baking oven~for 24 hours, temperature is 80~120 DEG C, finally hydrogen-argon in 10% also
2~4h of original, temperature are 350~450 DEG C, obtain support type MIL-100 (Fe)-SO3Na catalyst.
It is 2. according to claim 1 a kind of using support type MIL-100 (Fe)-SO3Na catalyst is hydrogenated with phenolic compound
The method of deoxidation, it is characterised in that：The source of iron is ferric nitrate, one kind in iron chloride, ferric acetyl acetonade；Organic ligand is
One kind in trimesic acid, trimethyl trimesate.
It is 3. according to claim 1 a kind of using support type MIL-100 (Fe)-SO3Na catalyst is hydrogenated with phenolic compound
The method of deoxidation, it is characterised in that：The precious metal salt is nitric acid ruthenium, one kind in radium chloride, palladium nitrate, platinum chloride.
4. support type MIL-100 (Fe)-SO according to claim 13Na catalyst can be used for the hydrogenation of phenolic compound to take off
Oxygen reacts, and method is：By support type MIL-100 (Fe)-SO3Na catalyst and it is put into batch reactor in phenolic compound
In, hydrogenation deoxidation 1~10h of reaction is carried out under the conditions of 2~4MPa of Hydrogen Vapor Pressure, 100~250 DEG C of temperature, is finally obtained in phenol
Class compound hydrogenation deoxidation product；The phenolic compound is phenol, one kind in guaiacol, cresols.
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| CN201711157424.9A CN108048130A (en) | 2017-11-20 | 2017-11-20 | It is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the method for phenolic compound hydrogenation deoxidation |
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| CN201711157424.9A CN108048130A (en) | 2017-11-20 | 2017-11-20 | It is a kind of to use support type MIL-100 (Fe)-SO3Na catalyst is to the method for phenolic compound hydrogenation deoxidation |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110624608A (en) * | 2019-09-24 | 2019-12-31 | 山东建筑大学 | Preparation process and application of Fe-based metal organic framework solid acid catalyst |
| CN111855764A (en) * | 2020-07-14 | 2020-10-30 | 暨南大学 | Electrochemical sensor for detecting bisphenol A and preparation method and application thereof |
| CN112521619A (en) * | 2020-11-13 | 2021-03-19 | 太原理工大学 | Anion post-displacement green synthesis MIL-101(Cr) -X-Method (2) |
| CN116139857A (en) * | 2023-02-25 | 2023-05-23 | 湘潭大学 | Composite catalyst for preparing hydrocarbon fuel by deoxidization and preparation method thereof |
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2017
- 2017-11-20 CN CN201711157424.9A patent/CN108048130A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110624608A (en) * | 2019-09-24 | 2019-12-31 | 山东建筑大学 | Preparation process and application of Fe-based metal organic framework solid acid catalyst |
| CN111855764A (en) * | 2020-07-14 | 2020-10-30 | 暨南大学 | Electrochemical sensor for detecting bisphenol A and preparation method and application thereof |
| CN111855764B (en) * | 2020-07-14 | 2022-07-26 | 暨南大学 | Application of electrochemical sensor for detecting bisphenol A in electronic refuse dump dust |
| CN112521619A (en) * | 2020-11-13 | 2021-03-19 | 太原理工大学 | Anion post-displacement green synthesis MIL-101(Cr) -X-Method (2) |
| CN112521619B (en) * | 2020-11-13 | 2022-04-01 | 太原理工大学 | Anion post-displacement green synthesis MIL-101(Cr) -X-Method (2) |
| CN116139857A (en) * | 2023-02-25 | 2023-05-23 | 湘潭大学 | Composite catalyst for preparing hydrocarbon fuel by deoxidization and preparation method thereof |
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