CN103130718A - Magnetic ion liquid, preparation method of magnetic ion liquid and application of magnetic ion liquid - Google Patents
Magnetic ion liquid, preparation method of magnetic ion liquid and application of magnetic ion liquid Download PDFInfo
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- CN103130718A CN103130718A CN2012103817462A CN201210381746A CN103130718A CN 103130718 A CN103130718 A CN 103130718A CN 2012103817462 A CN2012103817462 A CN 2012103817462A CN 201210381746 A CN201210381746 A CN 201210381746A CN 103130718 A CN103130718 A CN 103130718A
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- ion liquid
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The invention relates to magnetic ion liquid, and particularly relates to the magnetic ion liquid, a preparation method of the magnetic ion liquid and application in reducing sulfur content in fuel oil in a catalytic oxidation mode of the magnetic ion liquid. The magnetic ion liquid is not only used as a catalyst but also used as an extraction agent in the reaction process. The magnetic ion liquid and oil products are immiscible in the reaction process, and the magnetic iron liquid has high catalytic activity, is capable of activating oxygen and separating ionic liquid and the oil products through an applied magnetic field after the reaction finishes, and facilitates recovery of the magnetic ion liquid and recycling of the magnetic ion liquid.
Description
Technical field
The present invention relates to magnetic ionic liquids, refer in particular to a kind of magnetic ionic liquids and preparation method thereof volume and reduce the purposes of sulphur content in fuel oil at catalyzed oxidation, and can pass through externally-applied magnetic field separating ionic liquid and fuel oil.
Background technology
The a large amount of SO that produce in sulfocompound combustion processes in fuel oil (gasoline or diesel oil)
x, be to form acid rain, cause the one of the main reasons of environmental pollution on a large scale, the mankind's health and the eubiosis of the earth in serious threat.Countries in the world are more and more stricter to the requirement of sulphur content in fuel oil; At present, although inorganic sulfur and the part organosulfur of the hydrodesulfurization of industrial extensive employing in can the effective elimination fuel oil is very low to the desulfuration efficiency with substituent thiophene, thionaphthene, dibenzothiophene and other thiophene derivant; For this reason, each state has all strengthened the research to other degree of depth process for sulfur removal, and as oxidation sweetening method, liquid-phase extraction method, direct absorption method, biological desulphurization method etc., wherein, the oxidation sweetening method is acknowledged as a very promising desulfurization technology; Yet, this method still exists a lot of difficulties in realizing industrialized process, especially the design of the cost of oxygenant and high activated catalyst also fails to be solved at all, therefore, the key of oxidation sweetening method is a kind of low cost of exploitation and highly active catalytic oxidation system, realizes cleaning, efficiently, the degree of depth removes organosulfur in fuel oil with it.
Ionic liquid is compared with traditional organic solvent as a kind of emerging " green solvent ", has many incomparable special performances, and mainly contain: fusing point is low, has wider liquid scope, can be in wide range the selective reaction temperature; Good acidity, and in very large range acid adjustable; Almost there is no vapour pressure, non-volatile, nonflammable and blast has been avoided a large amount of volatile organic solvent pollution on the environments and to operator's injury, has been the safe green replace solvents; Thermostability and chemical stability preferably; Can reuse.
Magnetic ionic liquids is the earliest by discoveries such as Hayashi, with [Bmim] Cl and FeCl
3React under nitrogen, can obtain magnetic ionic liquids [Bmim] Cl/FeCl
3, this ionic liquid can be responded to externally-applied magnetic field consumingly, has paramagnetism (Chem. Lett., Vol. 33,1590 ~ 1591,2004).
The research that ionic liquid is used for fuel desulfuration mainly contains two kinds of methods: direct abstraction desulfurization method and extraction coupling hydrogen peroxide oxidation doctor treatment; Li etc. also are used for the desulfurization of fuel oil with ion liquid abstraction and hydrogen peroxide oxidation combination, with 1-butyl-3-Methylimidazole iron(ic) chloride ([Bmim] Cl/FeCl
3) be extraction agent and catalyzer, the sulphur content in mould oil is reduced to 8 ppm (Green Chem. Vol. 11,810 ~ 815) by 1000 initial ppm;
Ionic liquid-catalyzed oxidation sweetening system ionic liquid after reaction of report is thorough not with separating usually of oil product, adopts magnetic field to control separating of ionic liquid and oil product, and present application does not in this respect also have report.
Summary of the invention
The present invention relates to a kind of magnetic ionic liquids catalyzed oxidation and reduce sulphur content in fuel oil, and can pass through magnetic resolution ionic liquid and fuel oil under externally-applied magnetic field, these ionic liquids meet following general formula:
Q
+[M
n+X
mY
N-m+1]
-Or [Q
+]
2[M
n+X
mY
N-m+2]
2-Or [Q
+]
3[M
n+X
mY
N-m+3]
3-
Positively charged ion in the present invention comes Q
+The expression quaternary ammonium cation (
), glyoxaline cation (
), pyridylium (
) Huo quaternary phosphine positively charged ion (
).
[0007]On positively charged ion, substituting group is identical or different straight-chain paraffin or H, and carbonatoms is 1-16.
M in the present invention
n+Be Fe, Co or the Ni metal ion of n for Oxidation Number; X, Y are Cl
-, Br
-, CN
-Or SCN
-, m equals n, is 2 or 3.
In the present invention, the magnetic of magnetic ionic liquids comes from transition-metal Fe, Co, Ni, is owing to existing not paired single electron to produce in transition metal.
The preparation method of magnetic ionic liquids in the present invention: the Q of 1:1 weighing in molar ratio
+X
-With alkyl chloride yl carboxylic acid or the Q of 1:1 weighing in molar ratio
+X
-With cycloalkanes sulfonic acid, Q
+For quaternary ammonium cation (
), glyoxaline cation (
), pyridylium (
) Huo quaternary phosphine positively charged ion (
), X
-Be Cl
-Or Br
-, 1:0.5～1:2 is at 90 ℃ of reaction 24 h in molar ratio with MXn again for reaction 24 h under 60 ℃, the product that obtains, and M is that Oxidation Number is Fe, Co or the Ni metal ion of n, and X is Cl
-, Br
-, CN
-Or SCN
-, n is 2 or 3, makes magnetic ionic liquids, 50 ℃ of oven dry in vacuum drying oven.
[0011]In the present invention, magnetic ionic liquids is used for the method for fuel oil oxidation sweetening: the fuel oil type: (1) mould oil is that dibenzothiophene is dissolved in octane, and being made into sulphur content is 500 ppm mould oils; (2) diesel oil is diesel oil after hydrotreatment, and sulphur content is 150 ppm; (3) FCC gasoline, sulphur content are 300 ppm; In autoclave, with oil product and magnetic ionic liquids by volume 5:1 add, pass into pure oxygen or air in reactor, react at setting pressure and temperature, by externally-applied magnetic field, ionic liquid is separated with oil product after reaction, oil product adopts GC-FID to detect the content of oily medium sulphide content, calculates desulfurization degree:
In the present invention, magnetic ionic liquids can extract the fuel oil medium sulphide content.
In the present invention, magnetic ionic liquids can activate pure oxygen or air.
In the present invention, magnetic ionic liquids and fuel oil do not dissolve each other.
In the present invention, magnetic ionic liquids finishes and can separate by externally-applied magnetic field in reaction.
In the present invention, magnetic ionic liquids can recycle or can regenerate.
Oxidation reaction condition of the present invention is gentle, and temperature of reaction is at 5～70 ℃.
Reaction pressure of the present invention is 0.5～5MPa.
In 5～30 minutes reaction times of the present invention, reacted preferably 10 minutes.
The invention provides a kind of Magnetic Fluids, magnetic ionic liquids in reaction process not only as catalyzer, also as extraction agent, magnetic ionic liquids does not dissolve each other with oil product in reaction process, magnetic ionic liquids has high catalytic activity, can activate oxygen, can pass through externally-applied magnetic field separating ionic liquid and oil product after reaction, be convenient to the recovery of magnetic ionic liquids and recycle.
The present invention has the following advantages:
1, oxygen is cheap and easy to get, is a kind of Green Oxidant, and therefore, this reaction conditions is gentle, does not need it
Its organic solvent, harmless to human and environment.
2, the magnetic ionic liquids effect of extracting that screens is good, and catalytic activity is high, can be with sulphur content in fuel oil
Drop to below 50 ppm.
3, magnetic ionic liquids and oil product do not dissolve each other, after reaction finishes, and under externally-applied magnetic field, magnetic ion liquid
Body separates with fuel oil thoroughly, and ionic liquid can repeatedly recycle.
Embodiment
Give further instruction below by example to the present invention.
The fuel oil type: (1) mould oil is that dibenzothiophene (DBT) is dissolved in octane, and being made into sulphur content is 500 ppm mould oils; (2) diesel oil is diesel oil after hydrotreatment, and sulphur content is 150 ppm; (3) FCC gasoline, sulphur content are 300 ppm.
Example 1-9In autoclave, with oil product and magnetic ionic liquids by volume 5:1 add, pass into oxygen in reactor, react under design temperature and pressure, by externally-applied magnetic field, ionic liquid is separated with oil product after reaction, oil product adopts GC-FID to detect the content of oily medium sulphide content, calculates desulfurization degree, the results are shown in following table.
Claims (4)
1. magnetic ionic liquids, it is characterized in that: described ionic liquid meets following general formula:
Q
+[M
n+X
mY
N-m+1]
-, [Q
+]
2[M
n+X
mY
N-m+2]
2-Or [Q
+]
3[M
n+X
mY
N-m+3]
3-
Q
+The expression quaternary ammonium cation (
), glyoxaline cation (
), pyridylium (
) Huo quaternary phosphine positively charged ion (
), on positively charged ion, substituting group is identical or different straight-chain paraffin or H, the straight-chain paraffin carbonatoms is 1-16;
M
n+Be Fe, Co or the Ni metal ion of n for Oxidation Number; X, Y are Cl
-, Br
-, CN
-Or SCN
-, m equals n, is 2 or 3.
2. the preparation method of a kind of magnetic ionic liquids as claimed in claim 1, is characterized in that: the Q of 1:1 weighing in molar ratio
+X
-With alkyl chloride yl carboxylic acid or the Q of 1:1 weighing in molar ratio
+X
-With cycloalkanes sulfonic acid, Q
+For quaternary ammonium cation (
), glyoxaline cation (
), pyridylium (
) Huo quaternary phosphine positively charged ion (
), X
-Be Cl
-Or Br
-, 1:0.5～1:2 is at 90 ℃ of reaction 24 h in molar ratio with MXn again for reaction 24 h under 60 ℃, the product that obtains, and M is that Oxidation Number is Fe, Co or the Ni metal ion of n, and X is Cl
-, Br
-, CN
-Or SCN
-, n is 2 or 3, makes magnetic ionic liquids, 50 ℃ of oven dry in vacuum drying oven.
3. a kind of magnetic ionic liquids as claimed in claim 1 reduces the purposes of sulphur content in fuel oil at catalyzed oxidation, it is characterized in that: in autoclave, with oil product and magnetic ionic liquids by volume 5:1 add, pass into pure oxygen or air in reactor, react at setting pressure and temperature, by externally-applied magnetic field, ionic liquid is separated with oil product after reaction.
4. a kind of magnetic ionic liquids as claimed in claim 3 reduces the purposes of sulphur content in fuel oil at catalyzed oxidation, and it is characterized in that: temperature of reaction is at 5～70 ℃, and reaction pressure is 0.5～5MPa, 5～30 minutes reaction times.
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| CN201210381746.2A CN103130718B (en) | 2012-10-10 | 2012-10-10 | A kind of magnetic ionic liquids and its production and use |
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| CN103450088A (en) * | 2013-09-22 | 2013-12-18 | 辽宁石油化工大学 | Novel sulfonic acid functionalized rhenium ionic liquid and preparation method and application thereof |
| CN103467384A (en) * | 2013-09-22 | 2013-12-25 | 辽宁石油化工大学 | Novel carboxylic acid functional rhenium iron liquid and preparation method and application thereof |
| CN103834432A (en) * | 2014-03-24 | 2014-06-04 | 中国科学院山西煤炭化学研究所 | Method for extracting, oxidizing and desulfuring fuel oil in ionic liquid |
| CN104316620A (en) * | 2014-11-12 | 2015-01-28 | 吉林大学 | Detection method of trace triazine herbicide |
| CN105238434A (en) * | 2015-10-22 | 2016-01-13 | 昆明理工大学 | Method for directional adjustment and control of liquid phase catalysis biomass thermal cracking by means of magnetic ion liquid |
| CN105368405A (en) * | 2015-10-22 | 2016-03-02 | 昆明理工大学 | Novel application of magnetic ionic liquid |
| CN113025371A (en) * | 2021-03-11 | 2021-06-25 | 中国矿业大学(北京) | Ionic liquid for extracting phenolic compounds from oil and screening method thereof |
| CN114561643A (en) * | 2022-03-16 | 2022-05-31 | 四川大学 | Chemical polishing solution for aluminum material and polishing method thereof |
| CN114573854A (en) * | 2022-03-16 | 2022-06-03 | 江苏大学 | Preparation method of quaternary phosphonium third porous ionic liquid |
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Cited By (16)
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|---|---|---|---|---|
| CN103467384A (en) * | 2013-09-22 | 2013-12-25 | 辽宁石油化工大学 | Novel carboxylic acid functional rhenium iron liquid and preparation method and application thereof |
| CN103467384B (en) * | 2013-09-22 | 2015-05-13 | 辽宁石油化工大学 | Novel carboxylic acid functional rhenium iron liquid and preparation method and application thereof |
| CN103450088A (en) * | 2013-09-22 | 2013-12-18 | 辽宁石油化工大学 | Novel sulfonic acid functionalized rhenium ionic liquid and preparation method and application thereof |
| CN103834432B (en) * | 2014-03-24 | 2016-01-27 | 中国科学院山西煤炭化学研究所 | A kind of method of ionic liquid intermediate fuel oil extraction oxidation sweetening |
| CN103834432A (en) * | 2014-03-24 | 2014-06-04 | 中国科学院山西煤炭化学研究所 | Method for extracting, oxidizing and desulfuring fuel oil in ionic liquid |
| CN104316620A (en) * | 2014-11-12 | 2015-01-28 | 吉林大学 | Detection method of trace triazine herbicide |
| CN104316620B (en) * | 2014-11-12 | 2016-01-20 | 吉林大学 | A kind of detection method of trace triazine herbicide |
| CN105368405A (en) * | 2015-10-22 | 2016-03-02 | 昆明理工大学 | Novel application of magnetic ionic liquid |
| CN105238434A (en) * | 2015-10-22 | 2016-01-13 | 昆明理工大学 | Method for directional adjustment and control of liquid phase catalysis biomass thermal cracking by means of magnetic ion liquid |
| CN105238434B (en) * | 2015-10-22 | 2017-03-08 | 昆明理工大学 | The method orienting regulation and control liquid-phase catalysis biomass through pyrolysis using magnetic ionic liquids |
| CN105368405B (en) * | 2015-10-22 | 2019-01-04 | 昆明理工大学 | The new application of magnetic ionic liquids |
| CN113025371A (en) * | 2021-03-11 | 2021-06-25 | 中国矿业大学(北京) | Ionic liquid for extracting phenolic compounds from oil and screening method thereof |
| CN113025371B (en) * | 2021-03-11 | 2022-03-01 | 中国矿业大学(北京) | Ionic liquid for extracting phenolic compounds from oil and screening method thereof |
| CN114561643A (en) * | 2022-03-16 | 2022-05-31 | 四川大学 | Chemical polishing solution for aluminum material and polishing method thereof |
| CN114573854A (en) * | 2022-03-16 | 2022-06-03 | 江苏大学 | Preparation method of quaternary phosphonium third porous ionic liquid |
| CN114573854B (en) * | 2022-03-16 | 2023-08-04 | 江苏大学 | Preparation method of quaternary phosphonium third-class porous ionic liquid |
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