CN106753514A - A kind of method of choline eutectic solvent abstraction desulfurization - Google Patents
A kind of method of choline eutectic solvent abstraction desulfurization Download PDFInfo
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- CN106753514A CN106753514A CN201611221879.8A CN201611221879A CN106753514A CN 106753514 A CN106753514 A CN 106753514A CN 201611221879 A CN201611221879 A CN 201611221879A CN 106753514 A CN106753514 A CN 106753514A
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- eutectic solvent
- oil
- choline eutectic
- choline
- abstraction desulfurization
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- 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
-
- 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
Abstract
The invention provides a kind of method of choline eutectic solvent abstraction desulfurization, the choline eutectic solvent for being used is mixed to get by quaternary ammonium salt and metal halide containing ethanol base；The step of abstraction desulfurization, is as follows：The choline eutectic solvent is added in oil product, stirring reaction for a period of time after, stop stirring.In method of the present invention, after reaction terminates, because eutectic solvent and oil product are presented two-phase, by it is simple topple over by separating oil；Prepared eutectic solvent can direct reuse, it is also possible to by being used after regeneration.
Description
Technical field
The present invention relates to abstraction desulfurization, a kind of method of choline eutectic solvent abstraction desulfurization is refered in particular to.
Background technology
In recent years, due in fuel oil sulfur-containing compound be eventually converted to SOx, this is to cause air pollution and is acid rain
Main cause.Therefore fuel desulfuration has become a global theme.The limitation of sulfur content is more and more stricter in fuel oil,
And strictly require to slow down that environment is subject to pollutes.Therefore, in future soon, the specification of " without sulphur " will be proposed.However, passing
The industrially desulfurized mode of system is hydrodesulfurization (HDS), and which needs high temperature (240-300 DEG C) and high pressure (1.6-
3.2MPa).Traditional hydrodesulfurization is not good to the removal effect of cyclic aromatic sulfide, such as dibenzothiophenes (DBT) and its
Derivative.Gasoline burns in car engine, and the sulfide of generation can make in-engine catalyst poisoning.In fuel oil, ring
The imperfect combustion of shape organic sulfur compound can cause to produce carbon distribution in engine, it will infringement engine, gasoline low-sulfurization can prolong
The life-span of engine long.Therefore, it is necessary to go in reduction fuel oil the method that sight focuses on the convenient green of exploitation one
Sulfide.In numerous non-hydrodesulfurizations, abstraction desulfurization (EDS) is most received because its gentle easy operating procedure turns into
One of mode of welcome.
Because ionic liquid is without flammable, the low advantage of vapour pressure, the abstraction desulfurization of oil product is widely used in, but to being at present
Only, what research was more is the ionic liquid of imidazole type or pyridine type, and it has the disadvantage that synthesis is complicated, high cost, and with latent
Toxicity.Eutectic solvent is a kind of solvent similar to ionic liquid, [Chem.Commun. (2003) 70- such as Abbott
71] people proposes the concept of eutectic solvent first, and it is pointed out, eutectic solvent compared to ionic liquid, convieniently synthesized, nothing
It is malicious, cheap.Eutectic solvent is mixed to get by the raw material of 2 kinds and the above, although it is in fields such as catalysis, organic syntheses
There are some to report,
Li etc. [Green Chem.15 (2013) 2793-2799] reports a series of abstraction desulfurization effect of eutectic solvents
Really, show that the eutectic solvent that tetrabutylammonium chloride and ethylene glycol are formed has preferable abstraction desulfurization effect, it can therefore be seen that
Eutectic solvent has certain application prospect for oil product abstraction desulfurization.
Based on above present situation, a kind of choline eutectic solvent is synthesized herein, its preparation process is simple, and reaction raw materials are just
Preferably, and resulting eutectic solvent there is desulfurization performance higher, extraction to be separated after terminating easy, renewable or circulation profit
With.
The content of the invention
The present invention is a kind of method of choline eutectic solvent abstraction desulfurization；Reaction condition of the present invention is gentle, operation letter
Just, the sulfide in oil product can effectively be removed.
The present invention is achieved through the following technical solutions：
A kind of method of choline eutectic solvent abstraction desulfurization, the choline eutectic solvent for being used is by base containing ethanol
Quaternary ammonium salt and metal halide be mixed to get；The step of abstraction desulfurization, is as follows：
The choline eutectic solvent is added in oil product, stirring reaction for a period of time after, stop stirring.
In the quaternary ammonium salt containing ethanol base, quaternary ammonium salt cationic formula is R1R2R3N+CH2CH2OH, wherein, R1It is alkyl
Substitution base is the saturated alkane of saturated alkane, aromatic hydrocarbons or alcoholic extract hydroxyl group substitution；R2For alkyl substituent is saturated alkane, aromatic hydrocarbons or alcohol
The saturated alkane of hydroxyl substitution；R3It is the saturated alkane that alkyl substituent is the substitution of saturated alkane, aromatic hydrocarbons or alcoholic extract hydroxyl group；Anion
It is chlorine or bromine.
The metal halide is FeCl3、CuCl2、ZnCl2、SnCl2、FeBr3In one kind.
The mass ratio 1 of the oil product and choline eutectic solvent:2~35:1.
The oil product is to be dissolved with benzothiophene (BT), 3- methyl benzothiophenes (3-MBT), dibenzothiophenes (DBT), 4-
The normal octane solution of methyldibenzothiophene (4-MDBT) or 4,6- dimethyl Dibenzothiophene (4,6-DMDBT).
The stirring reaction temperature is 0 DEG C~80 DEG C, and the stirring reaction time is 1min~3h.
A kind of choline eutectic solvent is used for the purposes of fuel desulfuration.
The choline eutectic solvent is used in the purposes of fuel desulfuration, and the fuel oil is crude oil, fuel oil or crude oil
Semi-finished product oil in refining process.
The present invention has advantages below：
(1) eutectic solvent of cholinomimetic has been synthesized first, quaternary ammonium moiety structure is similar with choline.
(2) choline eutectic solvent is convieniently synthesized, reactant utilization ratio 100%.
(3) quaternary ammonium salt used by synthesis eutectic solvent is cholinomimetic compound, and metal chloride heavy metal free can be biological
Degraded, it is non-toxic.
(4) the choline eutectic solvent for being screened has extraction efficiency high.
(5) in method of the present invention, after reaction terminates, because eutectic solvent and oil product are presented two-phase, by letter
It is single topple over by separating oil.
(6) eutectic solvent prepared by can direct reuse, it is also possible to by being used after regeneration.
Specific embodiment
The present invention is illustrated with following examples, but the present invention is not limited to following embodiments, the ancestor before and after not departing from
Under the scope of purport, change is included in technical scope of the invention.The preparation of oil product：By benzothiophene (BT), 3- first
Base benzothiophene (3-MBT), dibenzothiophenes (DBT), 4-MDBT (4-MDBT), 4,6- dimethyl dibenzo thiophenes
Fen (4,6-DMDBT) is dissolved in normal octane respectively, is made into sulfur content for 500ppm simulation oils.
Embodiment 1
By 0.1g eutectic solvents [C12DMEA]Cl/FeCl3([C12DMEA]Cl：Chlorinated dodecane base dimethyl ethanol ammonium)
It is added in the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stops after stirring 1min at 0 DEG C, now eutectic is molten
Agent, on upper strata, is 5.1% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil in lower floor, oil product
Embodiment 2
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 30min is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using in GC-FID detection oil
The content of DBT, is 52.9% by the removal efficiency for calculating oil product
Embodiment 3
By 7g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 3h is stirred at 80 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using DBT in GC-FID detection oil
Content, by calculate oil product removal efficiency be 86.2%.
Embodiment 4
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the simulation oil of 3.5g (5mL, BT) sulfur contents 500ppm
In, stop after 1h is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using DBT in GC-FID detection oil
Content, by calculate oil product removal efficiency be 42.9%.
Embodiment 5
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to 3.5g (5mL, 4,6-DMDBT) sulfur contents 500ppm's
In simulation oil, stop after stirring 1h at 25 DEG C, now in lower floor, oil product is detected eutectic solvent on upper strata using GC-FID
The content of DBT in oil, is 35.7% by the removal efficiency for calculating oil product.
Embodiment 6
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the mould of 3.5g (5mL, 4-MDBT) sulfur contents 500ppm
Intend in oil, stop after stirring 1h at 25 DEG C, now in lower floor, oil product detects oil to eutectic solvent on upper strata using GC-FID
The content of middle 4-MDBT, is 44.7% by the removal efficiency for calculating oil product.
Embodiment 7
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the simulation of 3.5g (5mL, 3-MBT) sulfur contents 500ppm
In oil, stop after stirring 10min at 25 DEG C, now in lower floor, oil product detects oil to eutectic solvent on upper strata using GC-FID
The content of middle 3-MBT, is 47.7% by the removal efficiency for calculating oil product.
Embodiment 8
By 1g eutectic solvents [C4DMEA]Cl/FeCl3([C4DMEA]Cl：Chlorobutanol dimethyl ethanol ammonium) it is added to
In the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stop after stirring 10min at 25 DEG C, now eutectic solvent exists
Lower floor, oil product, on upper strata, is 45.9% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil.
Embodiment 9
By 1g eutectic solvents [C8DMEA]Cl/FeCl3([C8DMEA]Cl：Chloro octyldimethyl ethanol ammonium) it is added to
In the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stop after stirring 10min at 25 DEG C, now eutectic solvent exists
Lower floor, oil product, on upper strata, is 47.5% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil.
Embodiment 10
By 1g eutectic solvents [BzDMEA] Cl/FeCl3([BzDMEA]Cl：Chlorobenzyl dimethyl ethanol ammonium) it is added to
In the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stop after stirring 10min at 25 DEG C, now eutectic solvent exists
Lower floor, oil product, on upper strata, is 39.2% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil.
Embodiment 11
By 1g eutectic solvents [BzMDEA] Cl/FeCl3([BzMDEA]Cl：Chlorobenzyl methyl diethanol ammonium) it is added to
In the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stop after stirring 10min at 25 DEG C, now eutectic solvent exists
Lower floor, oil product, on upper strata, is 39.7% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil.
Embodiment 12
By 1g eutectic solvents [C12DMEA]Cl/CuCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 10min is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using in GC-FID detection oil
The content of DBT, is 29.7% by the removal efficiency for calculating oil product.
Embodiment 13
By 1g eutectic solvents [C12DMEA]Cl/ZnCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 10min is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using in GC-FID detection oil
The content of DBT, is 32.3% by the removal efficiency for calculating oil product.
Embodiment 14
By 1g eutectic solvents [C12DMEA]Cl/SnCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 10min is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using in GC-FID detection oil
The content of DBT, is 32.5% by the removal efficiency for calculating oil product.
Embodiment 15
By 1g eutectic solvents [C12DMEA]Cl/FeBr3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after 10min is stirred at 25 DEG C, now eutectic solvent is in lower floor, oil product on upper strata, using in GC-FID detection oil
The content of DBT, is 55.6% by the removal efficiency for calculating oil product.
Embodiment 16
By 1g eutectic solvents [C12DMEA]Br/FeCl3[C12DMEA]Br：Bromododecane base dimethyl ethanol ammonium) plus
Enter in the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm, stop after stirring 10min at 25 DEG C, now eutectic is molten
Agent, on upper strata, is 54.6% by the removal efficiency for calculating oil product using the content of DBT in GC-FID detection oil in lower floor, oil product.
Embodiment 17
By 1g eutectic solvents [C12DMEA]Br/FeCl3It is added to the half-finished diesel (sulfur content after hydrodesulfurization
In 527ppm), stop after stirring 10min at 25 DEG C, now eutectic solvent in lower floor, on upper strata using fluorescence surveyed by oil product
The content of sulphur, is 43.3% by the removal efficiency for calculating oil product in sulphur instrument detection oil.
Embodiment 18
By 1g eutectic solvents [C12DMEA]Cl/FeCl3It is added to the simulation oil of 3.5g (5mL, DBT) sulfur contents 500ppm
In, stop after stirring 10min at 25 DEG C, oil product is taken out by tipping, new eutectic solvent is continuously added, 4 times repeatedly
Afterwards, it is 99.3% by calculating the removal efficiency of oil product using the content of DBT in GC-FID detection oil, sulfur content is down to 3.5ppm.
Choline eutectic solvent prepared by the present invention can be used in crude oil, fuel oil or crude refinement processes half
Product oil, there is good effect of extracting.
Claims (8)
1. a kind of method of choline eutectic solvent abstraction desulfurization, it is characterised in that the choline eutectic solvent for being used
It is mixed to get by quaternary ammonium salt and metal halide containing ethanol base；The step of abstraction desulfurization, is as follows：
The choline eutectic solvent is added in oil product, stirring reaction for a period of time after, stop stirring.
2. the method for a kind of choline eutectic solvent abstraction desulfurization according to claim 1, it is characterised in that described to contain
In the quaternary ammonium salt of ethanol base, quaternary ammonium salt cationic formula is R1R2R3N+CH2CH2OH, wherein, R1For alkyl substituent is saturation alkane
The saturated alkane of hydrocarbon, aromatic hydrocarbons or alcoholic extract hydroxyl group substitution；R2It is the saturation that alkyl substituent is the substitution of saturated alkane, aromatic hydrocarbons or alcoholic extract hydroxyl group
Alkane；R3It is the saturated alkane that alkyl substituent is the substitution of saturated alkane, aromatic hydrocarbons or alcoholic extract hydroxyl group；Anion is chlorine or bromine.
3. a kind of method of choline eutectic solvent abstraction desulfurization according to claim 1, it is characterised in that the gold
Category halide is FeCl3、CuCl2、ZnCl2、SnCl2、FeBr3In one kind.
4. a kind of method of choline eutectic solvent abstraction desulfurization according to claim 1, it is characterised in that the oil
The mass ratio 1 of product and choline eutectic solvent:2~35:1.
5. a kind of method of choline eutectic solvent abstraction desulfurization according to claim 1, it is characterised in that the oil
Product are to be dissolved with benzothiophene, 3- methyl benzothiophenes, dibenzothiophenes, 4-MDBT or 4,6- dimethyl hexichol
The normal octane solution of bithiophene.
6. the method for a kind of choline eutectic solvent abstraction desulfurization according to claim 1, it is characterised in that described to stir
It is 0 DEG C~80 DEG C to mix reaction temperature, and the stirring reaction time is 1min~3h.
7. the choline eutectic solvent described in a kind of claim 1~6 any one is used for the purposes of fuel desulfuration.
8. a kind of choline eutectic solvent according to claim 7 is used for the purposes of fuel desulfuration, it is characterised in that institute
It is the semi-finished product oil in crude oil, fuel oil or crude refinement processes to state fuel oil.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107163977A (en) * | 2017-07-12 | 2017-09-15 | 青岛科技大学 | A kind of method of adjacent halogen aromatic alcohol low-temperature eutectic solvent extraction desulfurization |
| CN107312565A (en) * | 2017-08-31 | 2017-11-03 | 青岛科技大学 | A kind of method of three components eutectic agent abstraction desulfurization |
| CN109888181A (en) * | 2019-03-04 | 2019-06-14 | 浙江众泰汽车制造有限公司 | A kind of carbon nitrogen lithium multiphase doped lithium ion battery negative electrode material and preparation method thereof and anode plate for lithium ionic cell and lithium ion battery |
| CN111808631A (en) * | 2020-06-22 | 2020-10-23 | 江苏中江材料技术研究院有限公司 | Catalytic oxidation desulfurization method for choline ternary eutectic solvent |
| 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 |
| CN112625744A (en) * | 2019-10-08 | 2021-04-09 | 中国石油化工股份有限公司 | System and method for comprehensively utilizing oil products |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107163977A (en) * | 2017-07-12 | 2017-09-15 | 青岛科技大学 | A kind of method of adjacent halogen aromatic alcohol low-temperature eutectic solvent extraction desulfurization |
| CN107163977B (en) * | 2017-07-12 | 2019-03-29 | 青岛科技大学 | A kind of method of neighbour's halogen aromatic alcohol low-temperature eutectic solvent extraction desulfurization |
| CN107312565A (en) * | 2017-08-31 | 2017-11-03 | 青岛科技大学 | A kind of method of three components eutectic agent abstraction desulfurization |
| CN107312565B (en) * | 2017-08-31 | 2019-05-03 | 青岛科技大学 | A kind of method of three components eutectic agent abstraction desulfurization |
| CN109888181A (en) * | 2019-03-04 | 2019-06-14 | 浙江众泰汽车制造有限公司 | A kind of carbon nitrogen lithium multiphase doped lithium ion battery negative electrode material and preparation method thereof and anode plate for lithium ionic cell and lithium ion battery |
| CN112625744A (en) * | 2019-10-08 | 2021-04-09 | 中国石油化工股份有限公司 | System and method for comprehensively utilizing oil products |
| CN112625744B (en) * | 2019-10-08 | 2022-08-12 | 中国石油化工股份有限公司 | System and method for comprehensively utilizing oil products |
| CN111808631A (en) * | 2020-06-22 | 2020-10-23 | 江苏中江材料技术研究院有限公司 | Catalytic oxidation desulfurization method for choline ternary eutectic solvent |
| 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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