CN113603646A - Ionic liquid with temperature response performance, preparation method and application in treatment of oily sludge - Google Patents
Ionic liquid with temperature response performance, preparation method and application in treatment of oily sludge Download PDFInfo
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- CN113603646A CN113603646A CN202110973951.7A CN202110973951A CN113603646A CN 113603646 A CN113603646 A CN 113603646A CN 202110973951 A CN202110973951 A CN 202110973951A CN 113603646 A CN113603646 A CN 113603646A
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 108
- 239000010802 sludge Substances 0.000 title claims abstract description 51
- 230000004044 response Effects 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000003960 organic solvent Substances 0.000 claims abstract description 30
- 150000001450 anions Chemical class 0.000 claims abstract description 11
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 alkyl quaternary ammonium salt Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 4
- HZONRRHNQILCNO-UHFFFAOYSA-N 1-methyl-2h-pyridine Chemical compound CN1CC=CC=C1 HZONRRHNQILCNO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 25
- 229940125904 compound 1 Drugs 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 23
- 238000001035 drying Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229940125782 compound 2 Drugs 0.000 claims description 18
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 16
- 239000012265 solid product Substances 0.000 claims description 16
- 238000005303 weighing Methods 0.000 claims description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 14
- 229910021641 deionized water Inorganic materials 0.000 claims description 14
- 229910001510 metal chloride Inorganic materials 0.000 claims description 12
- 238000001291 vacuum drying Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 8
- 238000005119 centrifugation Methods 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- 239000011636 chromium(III) chloride Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 2
- 239000010779 crude oil Substances 0.000 abstract description 39
- 238000000605 extraction Methods 0.000 abstract description 27
- 238000004064 recycling Methods 0.000 abstract description 11
- 238000000926 separation method Methods 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 9
- 238000011065 in-situ storage Methods 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000003921 oil Substances 0.000 description 41
- 239000007788 liquid Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 23
- 239000012071 phase Substances 0.000 description 21
- 238000011084 recovery Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000004451 qualitative analysis Methods 0.000 description 6
- 238000004445 quantitative analysis Methods 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- 229910020881 PMo12O40 Inorganic materials 0.000 description 4
- 229910020628 SiW12O40 Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 3
- 150000005838 radical anions Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003027 oil sand Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F11/00—Treatment of sludge; Devices therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/04—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Treatment Of Sludge (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention relates to an ionic liquid with temperature response performance, a preparation method and application in treating oily sludge; the molecular formula of the ionic liquid is as follows: z [ XSO ]3A]m Yn(ii) a Wherein Z is a metal ion, particularly preferably Al3+、Cr3+(ii) a X is an alkyl side chain containing carbon atoms; a is N-methylimidazole, N-methylpyridine and alkyl quaternary ammonium salt; y is a heteropolyacid anion; m and n are for keeping the ionic liquid chargedBalance of charge and anion. The ionic liquid with temperature control performance is dissolved in an organic solvent when the temperature is raised, so that the ionic liquid becomes a homogeneous reaction system during reaction, and has the advantage of homogeneous extraction. And after the reaction is finished, the system is cooled to room temperature, the temperature-controlled ionic liquid can be gradually separated out from the organic solvent, the in-situ separation is realized, the subsequent recycling is convenient, the ionic liquid can be recycled for many times, the resources are saved, the crude oil extraction effect is obviously improved, and the extraction effect is higher than that of the existing extraction effect and is as high as 95.6%.
Description
Technical Field
The invention belongs to the field of harmless treatment of oil sludge and the technical field of green extraction, and relates to an extractant, in particular to a preparation method and application of an ionic liquid with temperature response performance, and a method for recycling and harmless treatment of oil-containing sludge by using the ionic liquid. Provides the ionic liquid with temperature response performance, the preparation method and the application in the treatment of oily sludge.
Background
Oily sludge is a solid waste rich in mineral oil, which is generated in the petroleum exploration and development industry and the petrochemical industry production industry, and is not inherently present in nature. The oily sludge mainly comprises oil, silt and water, wherein the water content is 20-50%, the oil content is 30-60%, and the solid content is 10-40%. The crude oil yield is estimated to be 1.6 multiplied by 10 per year in China at present8The oil-containing sludge produced by the method accounts for about 0.5-1% of the crude oil yield (nearly millions of tons of oil sludge, oil sand and the like are produced every year), and the oil-containing sludge and the like are accumulated in an oil tank for a long time due to the oil sludge discharge restriction policy of the environmental protection department, so that the operation device is not burdened, and the normal operation of oil field production is seriously hindered. In addition, the oily sludge has complex components, contains a large amount of organic pollutants, inorganic matters, heavy metals and even radioactive toxic substances, and is difficult to settle, so that the land structure and the underground water quality are deeply affected, the ecological structure is damaged, and the health of human bodies is seriously threatened. The oily sludge also contains various pathogenic bacteria, parasitic ova, homologues of benzene, anthracene, pyrene and other highly toxic substances, and the substances are exposed in the air for a long time and then can be infected infinitely. Fossil energy such as petroleum is a non-renewable resource, and thus oily sludge is efficiently treated in order to obtain good sludgeThe oil recovery rate not only accords with the development concept of sustainable development, but also accords with the development requirement of building an environment-friendly society.
The Ionic liquid (ILs for short) is a molten salt which is liquid at room temperature, structurally and completely consists of an anion part and a cation part, and has the advantages of low vapor pressure, low melting point, high stability, wide electrochemical window, adjustable structure and the like. In addition, it has a wide range of applications in various fields due to its ductile physical and chemical properties. The use of ionic liquid provides a more sustainable chemical extraction method for recycling and harmless treatment of oily sludge, and has proved to have good potential in enhancing the solvent extraction of crude oil. However, although the homogeneous extractant can improve the extraction effect, it cannot be recovered and separated by a simple method after the reaction is finished, which causes a great deal of resource waste, and the heterogeneous extractant is often limited in application due to poor mass transfer effect.
Patent CN110386753A researches that an ionic liquid-based oil sludge acidic separation treatment agent is used for treating oil sludge, the separation treatment agent is mainly a mixture consisting of ionic liquid and auxiliary materials, petroleum hydrocarbon is effectively stripped, separated and enriched, resource utilization and harmless treatment of the oil sludge are realized, and the oil content of the recovered oil sludge can reach 89.6%. Patent CN110272174A researches an alkaline separating agent mainly composed of ionic liquid, bio-based active substances and auxiliary materials for treating oil sludge, and the oil content of the recovered oil sludge can reach 90.1%.
The ionic liquid has higher cost, and the method for recovering the ionic liquid after reaction such as rotary evaporation is mostly adopted in the invention, so that the ionic liquid is greatly lost, and a large amount of resources are wasted. The invention aims to realize the in-situ separation of the ionic liquid and a reaction system at the same time of finishing the reaction on the basis of continuously improving the recovery rate of crude oil, thereby realizing the cyclic utilization of resources.
Disclosure of Invention
The invention aims to provide an ionic liquid with temperature response performance, a preparation method and application in treating oily sludge, wherein the ionic liquid can form a homogeneous system with a reaction system when the temperature is increased, so that the reaction is facilitated, and when the temperature is reduced to room temperature after the reaction is finished, the ionic liquid is self-formed into a phase, can be separated from the system in situ, and is convenient for subsequent recycling.
The invention also provides a preparation method of the temperature-controlled ionic liquid.
The invention also provides application of the temperature-controlled ionic liquid in treatment of oily sludge.
According to the temperature-controlled ionic liquid provided by the invention, anions are heteropoly acid radical anions, and cations consist of metal ions and derivatives of imidazole, pyridine and quaternary ammonium salt with long paraffin.
The temperature-controlled ionic liquid provided by the invention is a UCST type ionic liquid, is mutually soluble with a solvent at the temperature of higher than 60 ℃, and can be separated from the solvent in situ at the temperature of lower than 60 ℃.
The technical scheme of the invention is as follows:
an ionic liquid with temperature response performance, which has a molecular formula as follows: z [ XSO ]3A]m Yn；
Wherein Z is a metal ion, particularly preferably Al3+、Cr3+(ii) a X is an alkyl side chain containing carbon atoms; a is N-methylimidazole, N-methylpyridine and alkyl quaternary ammonium salt; y is a heteropolyacid anion; m and n are the cation-anion ratio for keeping the charge balance of the ionic liquid.
The heteropoly acid radical anion is phosphomolybdate anion, phosphotungstic acid radical anion, silicotungstic acid radical anion or phosphomolybdovanadate radical anion.
A preparation method of an ionic liquid with temperature response performance comprises the following steps:
1) weighing 1, 3-propane sultone, adding the 1, 3-propane sultone into a container, adding toluene for dissolving, adding N-methylimidazole or pyridine derivative or quaternary ammonium salt derivative, reacting at the temperature of 50-120 ℃ for 1-12h, washing a solid product obtained after the reaction by using ethyl acetate, and then conveying the solid product into a vacuum drying oven for drying to obtain a compound 1;
2) dissolving the compound 1 in water, dropwise adding a heteropoly acid aqueous solution with the same molar weight as the compound 1 in the stirring process, after dropwise adding, raising the temperature to 60-100 ℃ at the temperature rise rate of 1-10 ℃ per minute, reacting for 1-10h, finally filtering and taking out the solid precipitate, and sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3) dissolving the compound 2 in deionized water at the temperature of 50-120 ℃, then mixing and adding the compound with metal chloride, and reacting for 1-6h at the temperature of 90-120 ℃ to obtain the ionic liquid with the temperature control function.
In the step 1), the volume ratio of the 1, 3-propane sultone to the toluene is 0.1-1: 1; the addition amount of the N-methylimidazole or pyridine derivative or quaternary ammonium salt derivative is 0.013mol-0.065 mol.
In the step 3), the metal chloride is specifically AlCl3Or CrCl3(ii) a The molar ratio of the metal chloride to the compound 2 is 1: 0.1-1.
The application method of the temperature-controlled ionic liquid in the treatment of the oily sludge is utilized; the method comprises the following steps:
1) weighing a sample of dehydrated oil sludge, putting the sample into a container, adding an organic solvent, fully mixing the sample and the organic solvent, and putting the mixture into an oil bath kettle for stirring;
2) adding temperature-controlled ionic liquid, starting to heat to 60-120 ℃, and reacting for 1-12 h;
3) after the reaction, the reaction system was centrifuged and the content was measured.
The organic solvent in the step 1) is n-heptane, carbon tetrachloride, toluene, petroleum ether, ethyl acetate or butyl acetate; the mass ratio of the addition amount of the organic solvent to the oil sludge sample is 1: 0.01-10; the stirring speed is 500r/min-3000 r/min.
The volume ratio of the addition amount of the organic solvent to the temperature-controlled ionic liquid in the step 2) is 0.1-10: 1.
The centrifugation speed in the step 3) is 1000r/min-5000 r/min; the centrifugation time is 5-30 min.
In application, the ionic liquid can be recycled.
The ionic liquid with the temperature response property is applied to form a double-liquid-phase extraction system with an organic solvent so as to improve the recovery rate of crude oil in oily sludge.
Compared with the prior art, the technical method provided by the invention has the technical progress that:
(1) the ionic liquid with the temperature control performance can be dissolved in an organic solvent when the temperature is increased, so that the ionic liquid becomes a homogeneous reaction system during reaction, and has the advantage of homogeneous extraction. After the reaction is finished, the system is cooled to room temperature, and the temperature-controlled ionic liquid can be gradually separated out from the organic solvent, so that in-situ separation is realized, the subsequent recycling is facilitated, and the defects of homogeneous phase and heterogeneous phase mass separating agents are overcome;
(2) the temperature-controlled ionic liquid provided by the invention can enhance the solubility of an extracting agent in a sample, assists an organic solvent to jointly complete the extraction of crude oil in oily sludge, can be recycled for multiple times, saves resources, and also obviously improves the extraction effect of the crude oil, which is higher than the existing extraction effect and is as high as 95.6%;
(3) the method for preparing the temperature-controlled ionic liquid and the technology for extracting the crude oil from the oily sludge provided by the invention have the advantages of efficient and environment-friendly process, mild and feasible reaction conditions and simple requirements on equipment.
The invention is suitable for the field of harmless treatment of oil sludge and the technical field of green extraction.
Detailed Description
Example 1
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1, 3-propane sultone into a three-neck flask, then adding 10mL of toluene for dissolving, then adding 0.013mol of 1-butyl-3-methylimidazole, reacting at the temperature of 50 ℃ for 1 hour, washing a solid product after reaction with ethyl acetate, then sending the solid product into a drying oven for drying, and then obtaining a compound 1;
2. dissolving the compound 1 in deionized water, stirring, gradually dropwise adding an aqueous solution containing phosphomolybdic acid in an equal molar amount to the compound 1 during stirring, raising the temperature to 60 ℃ at a rate of 2 ℃ per minute after dropwise adding, and reacting for 1 h. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 50 ℃ and subsequently reacted with the metal chloride AlCl3Mixing and adding according to the molar ratio of 1:0.1, and then reacting for 1h at 90 ℃ to obtain the ionic liquid Al [ SO ] with temperature control performance3BMIM]0.5PMo12O40。
Selecting Al [ SO ]3BMIM]0.5PMo12O40As a temperature control ionic liquid, n-heptane as an organic solvent is combined into a temperature control reaction system to carry out crude oil extraction and recovery on oily sludge:
1. firstly, weighing 10g of dehydrated oil sludge into a three-neck flask, adding 100mL of organic solvent n-heptane solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 500 r/min;
2. adding 100mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 60 ℃ at the rate of 2 ℃ per minute and reacting for 1h, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugal rate is 1000r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after centrifugation for 5 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of n-heptane and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate reaches 92.1%, and the structure of the crude oil product is almost the same as that of the crude oil product. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
Example 2
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1, 3-propane sultone into a three-neck flask, then adding 3.3mL of toluene for dissolving, then adding 0.026mol of 1-butyl-3-methylimidazole, reacting for 1h at the temperature of 70 ℃, washing a solid product after reaction with ethyl acetate, then sending the solid product into a drying oven for drying, and then obtaining a compound 1;
2. dissolving the compound 1 in deionized water, stirring, gradually dropwise adding an aqueous solution containing phosphotungstic acid in an equimolar amount with the compound 1 in the stirring process, raising the temperature to 70 ℃ at a rate of 5 ℃ per minute after dropwise adding, and reacting for 5 hours. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 75 ℃ and subsequently reacted with the metal chloride AlCl3Mixing and adding the components according to a molar ratio of 8:1, and then reacting for 6 hours at 70 ℃ to obtain the ionic liquid Al [ SO ] with temperature control performance3BMIM]0.5PW12O40。
Selecting Al [ SO ]3BMIM]0.5PW12O40As a temperature control type ionic liquid, toluene is used as an organic solvent to be combined into a temperature control reaction system to carry out crude oil extraction and recovery on oily sludge:
1. firstly, weighing 20g of dehydrated oil sludge into a three-neck flask, adding 200mL of organic solvent toluene solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 1000 r/min;
2. adding 75mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 80 ℃ at the rate of 5 ℃ per minute and reacting for 6 hours, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugal rate is 3000r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after being centrifuged for 20 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of toluene and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate reaches 94.7%, and the structure of the crude oil product is almost the same as that of the crude oil product. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
Example 3
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1, 3-propane sultone into a three-neck flask, then adding 2mL of toluene for dissolving, then adding 0.04mol of 2-methylpyridine, reacting for 3h at the temperature of 80 ℃, cleaning a reacted solid product with ethyl acetate, and then sending the washed solid product into a drying oven for drying to obtain a compound 1;
2. dissolving the compound 1 in deionized water, stirring, gradually dropwise adding an aqueous solution containing phosphomolybdic acid in an equal molar amount to the compound 1 during stirring, raising the temperature to 80 ℃ at a rate of 5 ℃ per minute after dropwise adding, and reacting for 5 hours. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 80 ℃ and subsequently reacted with the metal chloride AlCl3Mixing and adding the components according to a molar ratio of 6:1, and then reacting for 5 hours at 70 ℃ to obtain the ionic liquid Al [ SO ] with temperature control performance3MPy]0.5PMo12O40。
Selecting Al [ SO ]3MPy]0.5PMo12O40As a temperature control type ionic liquid, toluene as an organic solvent is combined into a temperature control reaction system to extract and recover crude oil from oily sludgeThe process:
1. firstly, weighing 30g of dehydrated oil sludge into a three-neck flask, adding 300mL of organic solvent toluene solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 1000 r/min;
2. stirring for a period of time, adding 60mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 100 ℃ at a rate of 10 ℃ per minute and reacting for 2 hours, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugal rate is 3000r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after being centrifuged for 20 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of toluene and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate reaches 93.2%, and the structure of the crude oil product is almost the same as that of the original structure. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
Example 4
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1, 3-propane sultone into a three-neck flask, then adding 1.43mL of toluene for dissolving, then adding 0.0525mol of 2-methylpyridine, reacting for 4h at the temperature of 110 ℃, washing a reacted solid product with ethyl acetate, and then sending the washed solid product into a drying oven for drying to obtain a compound 1;
2. dissolving the compound 1 in deionized water, stirring, gradually dropwise adding a silicotungstic acid aqueous solution containing the same molar weight as the compound 1 in the stirring process, raising the temperature to 100 ℃ at the rate of 8 ℃ per minute after the dropwise adding is finished, and reacting for 5 hours. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 100 ℃ and then is reacted with a metal chloride CrCl3Mixing and adding the components according to a molar ratio of 4:1, and then reacting for 6 hours at 120 ℃ to obtain the ionic liquid Cr [ SO ] with temperature control performance3MPy]0.5SiW12O40。
Selecting Cr [ SO3MPy]0.5SiW12O40As a temperature control ionic liquid, ethyl acetate is used as an organic solvent to be combined into a temperature control reaction system to carry out crude oil extraction and recovery on oily sludge:
1. firstly, weighing 30g of dehydrated oil sludge into a three-neck flask, adding 120mL of organic solvent ethyl acetate solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 2000 r/min;
2. stirring for a period of time, adding 60mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 90 ℃ at a rate of 8 ℃ per minute and reacting for 3 hours, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugal rate is 3000r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after being centrifuged for 20 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of ethyl acetate and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate is 95.6%, and the structure of the crude oil product is almost the same as that of the crude oil product. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
Example 5
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1, 3-propane sultone into a three-neck flask, then adding 1.21mL of toluene for dissolving, then adding 0.0588mol of alkyl trimethyl quaternary ammonium salt, reacting at the temperature of 110 ℃ for 10 hours, washing a solid product after reaction by using ethyl acetate, and then sending the solid product into a drying oven for drying to obtain a compound 1;
2. dissolving the compound 1 in deionized water, stirring, gradually dropwise adding a silicotungstic acid aqueous solution containing the same molar amount as the compound 1 in the stirring process, raising the temperature to 100 ℃ at the rate of 8 ℃ per minute after the dropwise adding is finished, and reacting for 8 hours. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 110 ℃ and then is reacted with a metal chloride CrCl3Mixing and adding the components according to a molar ratio of 4:1, and then reacting for 4 hours at the temperature of 110 ℃ to obtain the ionic liquid Cr [ SO ] with the temperature control performance3NEt]0.5SiW12O40。
Selecting Cr [ SO3NEt]0.5SiW12O40As a temperature control ionic liquid, butyl acetate is used as an organic solvent to be combined into a temperature control reaction system to carry out crude oil extraction and recovery on oily sludge:
1. firstly, weighing 20g of dehydrated oil sludge into a three-neck flask, adding 80mL of organic solvent butyl acetate solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 2500 r/min;
2. adding 40mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 110 ℃ at the rate of 10 ℃ per minute and reacting for 9 hours, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugation speed is 4500r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after centrifugation for 25 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of butyl acetate and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate reaches 91.5%, and the structure of the crude oil product is almost the same as that of the crude oil product. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
Example 6
1. Firstly, weighing 1mL of 1, 3-propane sultone, adding the 1mL of toluene into a three-neck flask, dissolving the 1mL of toluene, adding 0.065mol of alkyl trimethyl quaternary ammonium salt, reacting at the temperature of 120 ℃ for 12 hours, cleaning a reacted solid product with ethyl acetate, and then sending the washed solid product into a drying oven for drying to obtain a compound 1;
2. dissolving the compound in deionized water, stirring, gradually dropwise adding an aqueous solution containing phosphomolybdic acid in an equimolar amount with the compound 1 during stirring, heating to 100 ℃ at a rate of 10 ℃ per minute after dropwise adding, and reacting for 10 hours. Finally, filtering and taking out the solid precipitate, and then sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3. compound 2 is dissolved in deionized water at a temperature of 120 ℃ and then is reacted with a metal chloride CrCl3Mixing and adding the components according to a molar ratio of 10:1, and then reacting for 6 hours at 120 ℃ to obtain the ionic liquid Cr [ SO ] with temperature control performance3NEt]0.5PMoV11O40。
Selecting Cr [ SO3NEt]0.5PMoV11O40As a temperature control ionic liquid, butyl acetate is used as an organic solvent to be combined into a temperature control reaction system to carry out crude oil extraction and recovery on oily sludge:
1. firstly, weighing 15g of dehydrated oil sludge into a three-neck flask, adding 275mL of organic solvent butyl acetate solution, fully mixing the two, putting the flask into an oil bath kettle, and stirring at the stirring speed of 3000 r/min;
2. adding 27.5mL of ionic liquid, observing a liquid-liquid two-phase system in the flask after the system is stable, then heating to 120 ℃ at a rate of 10 ℃ per minute and reacting for 12 hours, wherein the reaction system is a homogeneous phase system;
3. after the reaction is finished, the mixture is quickly transferred to a centrifugal tube for solid-liquid separation, the centrifugal rate is 5000r/min, and the mixture is observed to be divided into a solid phase and a liquid phase after being centrifuged for 30 min. When the temperature is gradually cooled to the room temperature, the mixture is divided into three phases of solid, liquid and liquid, wherein the upper layer is the mixture of butyl acetate and oil products.
And (3) conveying the mixture into a rotary evaporator to remove the solvent, wherein the power of a motor is 40W, the vacuum degree is 0.09MPa, the set temperature is 90 ℃, the obtained crude oil product is subjected to qualitative and quantitative analysis, the calculated crude oil recovery rate reaches 92.8%, and the structure of the crude oil product is almost the same as that of the crude oil product. The ionic liquid in the middle layer can be recovered by a simple pouring mode, the recovered ionic liquid and the pure ionic liquid are subjected to infrared spectrum analysis, the position of a characteristic peak of the recovered ionic liquid and the pure ionic liquid are not changed, and the ionic liquid is considered to be successfully recovered and can be recycled. After 5 times of recycling, the extraction rate is not obviously reduced. The sludge and other residues at the lowest layer can be discharged after reaching the standard or used as fuel by adding combustion improver and other modes.
The ionic liquid with temperature control performance and the specific organic solvent can be combined into a temperature control extraction system, so that the extraction effect of the organic solvent can be effectively enhanced, the ionic liquid can be separated in situ by reducing the temperature after the reaction is finished, the cost is greatly saved, the extraction effect of crude oil is greatly improved, the equipment investment is reduced, the sustainable development concept is met, and the development requirement for building an environment-friendly society is met.
While the methods and techniques of the present invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and/or modifications of the methods and techniques described herein may be made without departing from the spirit and scope of the invention. It is expressly intended that all such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and content of the invention. The invention belongs to the known technology.
Claims (10)
1. The ionic liquid with temperature response performance is characterized in that the molecular formula is as follows: z [ XSO ]3A]m Yn；
Wherein Z is a metal ion, particularly preferably Al3+、Cr3+(ii) a X is an alkyl side chain containing carbon atoms; a is N-methylimidazole, N-methylpyridine or alkyl quaternary ammonium salt; y is a heteropolyacid anion; m and n are the cation-anion ratio for keeping the charge balance of the ionic liquid.
2. An ionic liquid as claimed in claim 1, wherein the heteropolyacid anion is a phosphomolybdate anion, phosphotungstate anion, silicotungstic acid anion or phosphomolybdovanadate anion.
3. The preparation method of the ionic liquid with the temperature response performance is characterized by comprising the following steps of:
1) weighing 1, 3-propane sultone, adding the 1, 3-propane sultone into a container, adding toluene for dissolving, adding N-methylimidazole or pyridine derivative or quaternary ammonium salt derivative, reacting at the temperature of 50-120 ℃ for 1-12h, washing a solid product obtained after the reaction by using ethyl acetate, and then conveying the solid product into a vacuum drying oven for drying to obtain a compound 1;
2) dissolving the compound 1 in water, dropwise adding a heteropoly acid aqueous solution with the same molar weight as the compound 1 in the stirring process, after dropwise adding, raising the temperature to 60-100 ℃ at the temperature rise rate of 1-10 ℃ per minute, reacting for 1-10h, finally filtering and taking out the solid precipitate, and sending the solid precipitate into a vacuum drying oven for drying to obtain a compound 2;
3) dissolving the compound 2 in deionized water at the temperature of 50-120 ℃, then mixing and adding the compound with metal chloride, and reacting for 1-6h at the temperature of 90-120 ℃ to obtain the ionic liquid with the temperature control function.
4. The process as claimed in claim 3, wherein in step 1), the volume ratio of 1, 3-propane sultone to toluene is from 0.1 to 1: 1; the addition amount of the N-methylimidazole or pyridine derivative or quaternary ammonium salt derivative is 0.013mol-0.065 mol.
5. A process according to claim 3, characterized in that in step 3) the metal chloride is in particular AlCl3Or CrCl3(ii) a The molar ratio of the metal chloride to the compound 2 is 1: 0.1-1.
6. The application method of the temperature-controlled ionic liquid in the treatment of the oily sludge; the method comprises the following steps:
1) weighing a sample of dehydrated oil sludge, putting the sample into a container, adding an organic solvent, fully mixing the sample and the organic solvent, and putting the mixture into an oil bath kettle for stirring;
2) adding temperature-controlled ionic liquid, starting to heat to 60-120 ℃, and reacting for 1-12 h;
3) after the reaction, the reaction system was centrifuged and the content was measured.
7. The method according to claim 6, wherein the organic solvent in step 1) is n-heptane, carbon tetrachloride, toluene, petroleum ether, ethyl acetate or butyl acetate; the mass ratio of the addition amount of the organic solvent to the oil sludge sample is 1: 0.01-10; the stirring speed is 500r/min-3000 r/min.
8. The application method as claimed in claim 6, wherein the volume ratio of the organic solvent to the temperature-controlled ionic liquid added in the step 2) is 0.1-10: 1.
9. The use of claim 6, wherein in step 3) the centrifugation rate is 1000r/min to 5000 r/min; the centrifugation time is 5-30 min.
10. The ionic liquid of claim 6 can be recycled.
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