CN113082769A - Preparation method of amide III type eutectic solvent and application of amide III type eutectic solvent in fuel oil extraction and desulfurization - Google Patents
Preparation method of amide III type eutectic solvent and application of amide III type eutectic solvent in fuel oil extraction and desulfurization Download PDFInfo
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- CN113082769A CN113082769A CN202110466654.3A CN202110466654A CN113082769A CN 113082769 A CN113082769 A CN 113082769A CN 202110466654 A CN202110466654 A CN 202110466654A CN 113082769 A CN113082769 A CN 113082769A
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- 239000002904 solvent Substances 0.000 title claims abstract description 52
- 230000005496 eutectics Effects 0.000 title claims abstract description 51
- 150000001408 amides Chemical class 0.000 title claims abstract description 23
- 238000006477 desulfuration reaction Methods 0.000 title claims abstract description 20
- 230000023556 desulfurization Effects 0.000 title claims abstract description 20
- 239000000295 fuel oil Substances 0.000 title claims abstract description 18
- 238000000605 extraction Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003921 oil Substances 0.000 claims abstract description 39
- 125000003368 amide group Chemical group 0.000 claims abstract description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 16
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- SEBRPHZZSLCDRQ-UHFFFAOYSA-N 3-methyl-1-benzothiophene Chemical compound C1=CC=C2C(C)=CSC2=C1 SEBRPHZZSLCDRQ-UHFFFAOYSA-N 0.000 description 8
- MYAQZIAVOLKEGW-UHFFFAOYSA-N 4,6-dimethyldibenzothiophene Chemical compound S1C2=C(C)C=CC=C2C2=C1C(C)=CC=C2 MYAQZIAVOLKEGW-UHFFFAOYSA-N 0.000 description 6
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 6
- 239000002608 ionic liquid Substances 0.000 description 6
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 5
- NICUQYHIOMMFGV-UHFFFAOYSA-N 4-Methyldibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(C)=CC=C2 NICUQYHIOMMFGV-UHFFFAOYSA-N 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101000952234 Homo sapiens Sphingolipid delta(4)-desaturase DES1 Proteins 0.000 description 3
- 102100037416 Sphingolipid delta(4)-desaturase DES1 Human genes 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- DGUACJDPTAAFMP-UHFFFAOYSA-N 1,9-dimethyldibenzo[2,1-b:1',2'-d]thiophene Natural products S1C2=CC=CC(C)=C2C2=C1C=CC=C2C DGUACJDPTAAFMP-UHFFFAOYSA-N 0.000 description 2
- 101000737578 Arabidopsis thaliana Bifunctional cystathionine gamma-lyase/cysteine synthase Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 101100330363 Physcomitrium patens DES5 gene Proteins 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 102100034544 Acyl-CoA 6-desaturase Human genes 0.000 description 1
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
- 101000848255 Homo sapiens Acyl-CoA 6-desaturase Proteins 0.000 description 1
- 101000918926 Homo sapiens Sphingolipid delta(4)-desaturase/C4-monooxygenase DES2 Proteins 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 101100277598 Sorghum bicolor DES3 gene Proteins 0.000 description 1
- 102100029473 Sphingolipid delta(4)-desaturase/C4-monooxygenase DES2 Human genes 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- -1 aromatic sulfur compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000003009 desulfurizing effect Effects 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
-
- 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
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of extraction, desulfurization and synthesis of an extractant, and relates to an extractant of an eutectic solvent, in particular to a preparation method of an amide III type eutectic solvent, wherein amide is used as a hydrogen bond donor and is stirred and heated with quaternary ammonium salt in an oil bath at 0-100 ℃ for 0.5-8 h, and the mixture is kept stand and cooled to room temperature to obtain uniform transparent liquid, so that the amide III type eutectic solvent is obtained, wherein the molar ratio of the amide to the quaternary ammonium salt is 0.5-3: 1. the invention also aims to apply the prepared amide group III type eutectic solvent to the extraction and desulfurization of fuel oil. The preparation process has mild and green conditions, simple and convenient operation, cheap reaction raw materials and low cost, and the obtained eutectic solvent has higher desulfurization performance, is simple and convenient to separate from the model oil after extraction, and can be recycled. The prepared eutectic solvent has high desulfurization efficiency, is completely immiscible with model oil, and overcomes the limitations of high energy consumption, technical difficulty and the like in the synthesis of the traditional desulfurizer.
Description
Technical Field
The invention belongs to the technical field of extraction, desulfurization and synthesis of an extractant, relates to an extractant of an eutectic solvent, and particularly relates to a preparation method of an amide III type eutectic solvent and application of the amide III type eutectic solvent in fuel oil extraction and desulfurization.
Background
The sulfide in fuel oil is converted into Sulfur Oxide (SO) after combustionx) And seriously affect the environment and human health. In order to protect the environment depending on living, realize green sustainable development and reduce the sulfur content discharged to the air by fuel combustion, the governments of all countries set strict fuel sulfide content standards. In 2009 the european parliament will control the maximum sulfur content in fuel oil to 10ppm, and the chinese government is also trying to catch up with the fuel oil development level in other advanced countries, and it is known that the national desulfurization technology is developed rapidly from the national standard implemented in 2003 to the national standard implemented nowadays. With the continuous development and innovation of desulfurization technology, Hydrodesulfurization (HDS) and non-hydrodesulfurization are two methods for obtaining clean fuel oil at present. But the hydrodesulfurization condition is harsh, and the sulfide can be converted into H by using hydrogen and a catalyst under the conditions of high pressure (3.5-7.0 MPa) and high temperature (300-400 ℃), wherein the hydrogen and the catalyst are used2S, which results in a hydrodesulfurization technology that is costly and uneconomical to produce. Furthermore, aromatic sulfur compounds such as Benzothiophene (BT), Dibenzothiophene (DBT), and 4, 6-dimethyldibenzothiophene (4,6-DMDBT) are difficult to remove by HDS. Thus, non-HDS techniques such as: adsorption, oxidation, extraction and coupling techniques thereof are widely studied. Among them, Extractive Desulfurization (EDS) has milder conditions, fast reaction, lower octane number loss, simple synthesis, economy, environmental protection, etc. become a potential alternative to or coupled with hydrodesulfurization technologies. Despite its numerous advantages, finding a highly efficient extractant is critical to the success of extractive desulfurization.
The most important type of extractant used in the EDS process is the requirement to satisfy the following conditions: the sulfide has larger solubility in the extractant; the oil is insoluble with fuel oil to ensure that the oil is not polluted; the extractant has the characteristics of no toxicity or low toxicity, difficult volatilization, stable thermodynamic property and the like. The selection of the extractant is developed from the traditional organic solvent (such as acetonitrile, dimethyl sulfoxide, N-dimethylformamide and the like) to the Ionic Liquid (IL) which is relatively green and stable at present and the eutectic solvent (DES). The traditional organic solvent is easy to volatilize, most organic matters have high toxicity, and the industrial application of the ionic liquid is limited by the defects of complex synthetic route, long reaction period, expensive raw materials, high synthetic cost and the like of the ionic liquid. DES is a kind of green solvent that has been developed continuously on the basis of ionic liquid, it has many similarities with IL in physicochemical properties, but in addition, DES has the advantages of simple synthesis, low raw material price and low toxicity. In recent years, DES has good catalytic activity as a catalyst and also has the function of an extracting agent, can separate sulfide after reaction from model oil, directly uses DES as the extracting agent for extraction desulfurization, and has good development prospect.
Disclosure of Invention
In view of the defects in the prior art, the invention aims to disclose a preparation method of an amido III type eutectic solvent.
A preparation method of an amide III type eutectic solvent comprises the steps of taking amide as a hydrogen bond donor, stirring and heating the amide and quaternary ammonium salt in an oil bath at 0-100 ℃ for 0.5-8 h, standing and cooling to room temperature to obtain a uniform transparent liquid, and obtaining the amide III type eutectic solvent, wherein the molar ratio of the amide to the quaternary ammonium salt is 0.5-3: 1.
in the preferred embodiments of the present invention, the amide is acetamide, propionamide, butyramide, 2-phenylacetamide, terephthalamide, caprolactam, etc., preferably caprolactam.
In the preferred embodiment of the invention, the cation structural formula of the quaternary ammonium salt is shown as
Wherein R is1、R2、R3、R4Is alkyl or alkyl containing hydroxyl substituent, and the anion of the quaternary ammonium salt is F-、Cl-、Br-Or I-Preferably Br-。
The invention also aims to apply the prepared amide group III type eutectic solvent to the extraction and desulfurization of fuel oil.
The specific steps of extracting and desulfurizing are as follows: adding the prepared amide group III type eutectic solvent and fuel oil into a desulfurization glass reaction device, stirring at a constant temperature of 0-50 ℃ for 1-60 min for full reaction, stopping stirring, standing and separating, wherein the mass ratio of the fuel oil to the caprolactam group III type eutectic solvent is 1: 5-5: 1.
The fuel oil is crude oil, fuel oil or semi-finished oil in the crude oil refining process, and the initial sulfur concentration of the fuel oil is 10-50000 ppm.
The prepared amide III type eutectic solvent can be used for crude oil, fuel oil or semi-finished oil in the crude oil refining process, and has good extraction effect.
Advantageous effects
Based on the current technical situation of extraction desulfurization, the amide group III type eutectic solvent is synthesized and applied to the extraction desulfurization of fuel oil, the preparation process has mild and green conditions, the operation is simple and convenient, the reaction raw materials are cheap and low in cost, the obtained eutectic solvent has higher desulfurization performance, and the obtained eutectic solvent is simple and convenient to separate from model oil after extraction and can be recycled. The prepared eutectic solvent has high desulfurization efficiency, is completely immiscible with model oil, and overcomes the limitations of high energy consumption, technical difficulty and the like in the synthesis of the traditional desulfurizer.
Detailed Description
The present invention will be described in detail below with reference to examples to enable those skilled in the art to better understand the present invention, but the present invention is not limited to the following examples.
Preparation of oil products: benzothiophene (BT), 3-methylbenzothiophene (3-MBT), Dibenzothiophene (DBT), 4-methyldibenzothiophene (4-MDBT) or 4, 6-dimethyldibenzothiophene (4,6-DMDBT) were dissolved in n-dodecane solution, respectively, to prepare oils having sulfur contents of 10, 1000, 50000 ppm.
Acetamide is abbreviated as EA, terephthalamide is abbreviated as TPA, caprolactam is abbreviated as CPL, tetrabutylammonium bromide is abbreviated as TBAB, tetraoctylammonium bromide is abbreviated as TOAB, tetramethylammonium chloride is abbreviated as TMAC, tetrabutylammonium fluoride is abbreviated as TBAF, and tetrabutylammonium iodide is abbreviated as TBAI.
Example 1
Adding EA and TOAB into a 100mL round-bottom flask according to the molar ratio of 3:1, magnetically stirring for 0.5h under the condition of 100 ℃ constant-temperature water bath, and naturally cooling to room temperature after the reaction is finished to obtain a uniform and transparent eutectic solvent (DES 1).
0.5g of eutectic solvent DES1[ TOAB/EA ] was added to 2.5g of oil (DBT) containing 10ppm of sulfur, and the mixture was stirred at 0 ℃ for 1min, at which time the eutectic solvent was in the lower layer and the oil in the upper layer.
The content of DBT in the oil is detected by adopting GC-FID, and the removal rate of the oil is 36.3 percent by calculation.
Example 2
Adding TPA and TMAC into a 100mL round-bottom flask according to the molar ratio of 1:1, magnetically stirring for 4h under the condition of 50 ℃ constant-temperature water bath, and naturally cooling to room temperature after the reaction is finished to obtain a transparent eutectic solvent (DES 2).
1g of eutectic solvent DES2[ TMAC/TPA ] was added to 2.5g of (4-MDBT) oil with 1000ppm of sulfur content, and the mixture was stirred at 25 ℃ for 30min and stopped, with the eutectic solvent in the lower layer and the oil in the upper layer.
The content of 4-MDBT in the oil is detected by GC-FID, and the removal rate of the oil is calculated to be 55.2 percent.
Example 3
Adding CPL and TBAF into a 100mL round-bottom flask according to the molar ratio of 0.5:1, magnetically stirring for 4 hours under the condition of a constant-temperature water bath at 0 ℃, and naturally cooling to room temperature after the reaction is finished to obtain a transparent eutectic solvent (DES 3).
5g of eutectic solvent DES3[ TBAF/CPL ] was added to 2.5g of oil (4,6-DMDBT) with a sulfur content of 1000ppm, and stirring was stopped at 80 ℃ for 3h, with the eutectic solvent in the lower layer and the oil in the upper layer.
The GC-FID is adopted to detect the content of 4,6-DMDBT in the oil, and the removal rate of the oil product is calculated to be 81.6 percent.
Example 4
Adding CPL and TBAI into a 100mL round-bottom flask according to the molar ratio of 2:1, magnetically stirring for 4 hours under the condition of 80 ℃ constant-temperature water bath, and naturally cooling to room temperature after the reaction is finished to obtain the transparent eutectic solvent (DES 4).
12.5g of eutectic solvent DES4[ TBAI/CPL ] was added to 2.5g of (BT) oil with a sulphur content of 50000ppm and the stirring was stopped at 25 ℃ for 1h, with the eutectic solvent in the lower layer and the oil in the upper layer.
The content of BT in the oil is detected by GC-FID, and the removal rate of the oil product is 86.2 percent by calculation.
Example 5
CPL and TOAB are added into a 100mL round-bottom flask according to the molar ratio of 2:1, magnetic stirring is carried out for 4 hours under the condition of 80 ℃ constant-temperature water bath, and after the reaction is finished, the mixture is naturally cooled to the room temperature, so that the uniform and transparent eutectic solvent (DES5) is obtained.
5g of eutectic solvent DES5[ TOAB/CPL ] was added to 2.5g of (3-MBT) oil with a sulfur content of 1000ppm, and stirring was stopped at 25 ℃ for 1h, with the eutectic solvent in the lower layer and the oil in the upper layer.
The GC-FID is adopted to detect the content of the 3-MBT in the oil, and the removal rate of the oil product is calculated to be 70.1 percent.
Example 6
CPL and TBAB are added into a 100mL round-bottom flask according to the molar ratio of 2:1, magnetically stirred for 4 hours under the condition of 80 ℃ constant-temperature water bath, and naturally cooled to room temperature after the reaction is finished, so that the uniform and transparent eutectic solvent (DES6) is obtained.
5g of eutectic solvent DES1[ TBAB/CPL ] is added into 2.5g of oil (DBT) with the sulfur content of 200ppm, the stirring is stopped after 20min at 25 ℃, the oil product is taken out by a pouring method, new eutectic solvent is continuously added, the extraction is repeated, and the eutectic solvent is in the lower layer and the oil product is in the upper layer.
The content of DBT in the oil is detected by adopting GC-FID, and the removal rate of the oil product is 95.4 percent by calculation.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes performed by the present invention or directly or indirectly applied to other related technical fields are included in the scope of the present invention.
Claims (7)
1. A preparation method of an amide III type eutectic solvent is characterized in that: taking amide as a hydrogen bond donor, stirring and heating the amide and quaternary ammonium salt in an oil bath at 0-100 ℃ for 0.5-8 h, standing and cooling to room temperature to obtain uniform transparent liquid, wherein the molar ratio of the amide to the quaternary ammonium salt is 0.5-3: 1.
2. the method for preparing the amido group III eutectic solvent according to claim 1, wherein: the amide is acetamide, propionamide, butyramide, 2-phenylacetamide, terephthalamide or caprolactam.
3. The method for preparing the amido group III eutectic solvent according to claim 1, wherein: the amide is caprolactam.
4. The method for preparing the amido group III eutectic solvent according to claim 1, wherein: the cation structural formula of the quaternary ammonium salt is
Wherein R is1、R2、R3、R4Is alkyl or alkyl containing hydroxyl substituent, and the anion of the quaternary ammonium salt is F-、Cl-、Br-Or I-。
5. The method for preparing the amido group III eutectic solvent according to claim 1, wherein: the anion of the quaternary ammonium salt is Br-。
6. An amido group III eutectic solvent prepared according to the method of any one of claims 1 to 5.
7. Use of an amido group III eutectic solvent according to claim 6, wherein: the method is applied to fuel oil extraction desulfurization.
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| CN113617397A (en) * | 2021-07-30 | 2021-11-09 | 江苏大学 | Preparation of porous carbon loaded NHPI catalyst and application of porous carbon loaded NHPI catalyst in oxidative desulfurization of fuel oil |
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| CN108840311A (en) * | 2018-06-22 | 2018-11-20 | 南京大学 | It is a kind of using eutectic solvent as the hydrogen sulfide liquid phase oxidation removal method of medium |
| CN112625730A (en) * | 2020-11-23 | 2021-04-09 | 江苏大学 | Amide IV type eutectic solvent, preparation method thereof and application thereof in fuel oil desulfurization |
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2021
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| CN108840311A (en) * | 2018-06-22 | 2018-11-20 | 南京大学 | It is a kind of using eutectic solvent as the hydrogen sulfide liquid phase oxidation removal method of medium |
| CN112625730A (en) * | 2020-11-23 | 2021-04-09 | 江苏大学 | Amide IV type eutectic solvent, preparation method thereof and application thereof in fuel oil desulfurization |
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| CN113617397A (en) * | 2021-07-30 | 2021-11-09 | 江苏大学 | Preparation of porous carbon loaded NHPI catalyst and application of porous carbon loaded NHPI catalyst in oxidative desulfurization of fuel oil |
| CN113617397B (en) * | 2021-07-30 | 2023-04-25 | 江苏大学 | Preparation of porous carbon-supported NHPI catalyst and application of catalyst in fuel oil oxidative desulfurization |
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