CN110194965A - A kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration - Google Patents

A kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration Download PDF

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CN110194965A
CN110194965A CN201910429478.9A CN201910429478A CN110194965A CN 110194965 A CN110194965 A CN 110194965A CN 201910429478 A CN201910429478 A CN 201910429478A CN 110194965 A CN110194965 A CN 110194965A
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eutectic solvent
fuel oil
catalysis oxidation
fuel
components
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CN110194965B (en
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蒋伟
贾浩
李宏平
肖进
罗亚平
朱文帅
李华明
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Jiangsu University
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G27/00Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/12Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING 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
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20Characteristics of the feedstock or the products
    • C10G2300/201Impurities
    • C10G2300/202Heteroatoms content, i.e. S, N, O, P

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

The invention belongs to oxidation sweetening of oil product fields, and in particular to a kind of method of three component eutectic solvent catalysis oxidation fuel desulfurations;Using quaternary ammonium salt Huo quaternary alkylphosphonium salt as hydrogen bond receptor, boric acid and Organic Alcohol are hydrogen bond donor, and eutectic solvent is prepared;Using eutectic solvent as catalyst and extractant, hydrogen peroxide is oxidant, carries out oxidation removal to dibenzothiophenes class sulfide in oil product;It is cheap and easy to get that the present invention synthesizes raw material used in eutectic solvent, and can be prepared by by one-step method stirring, and the eutectic solvent of preparation is more environmentally protective, reaches 99.5% to the removal efficiency of sulphur, desulfurization effect is good, and eutectic solvent can be recycled.

Description

A kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration
Technical field
The invention belongs to oxidation sweetening of oil product fields, and in particular to a kind of three component eutectic solvent catalysis oxidation fuel oils are de- The method of sulphur.
Background technique
In recent decades, air pollution has become increasingly serious global problem, and generated in fuel combustion process A large amount of oxysulfides are one of main sources.The principal element that acid rain is formed is SOxIt is had occurred instead with substances such as water in air It answers, very big negative effect is carried out to environment and economy-zone.Furthermore SOxAutomotive exhaust catalysis reforming unit can be destroyed, further Aggravate environmental pollution.Therefore, fuel desulfuration is very urgent.Combustion industrially can be effectively removed using hydrodesulfurization at present Most of sulphur compounds in material.However, it is necessary to apply harsh reaction condition, for example, higher reaction temperature (> 300 DEG C) and Pressure (> 3MPa), could eliminate a small amount of dibenzothiophenes and its derivative.Therefore, one kind is developed in a mild condition from combustion The technology that thiophene-type sulfide is removed in material is particularly important, in total more desulfurization technologies, the single desulfuration efficiency of oxidation sweetening compared with Height selects suitable catalyst and extractant i.e. and can reach the requirement of deep desulfuration.
At present about eutectic solvent in terms of extracting the research of catalytic oxidation desulfurization, the researchers such as Li and L ü to be prepared for For different types of acidity eutectic solvent for extracting catalytic oxidation desulfurization, it is living that part eutectic solvent shows excellent desulfurization Property, also demonstrate prospect of the eutectic solvent for catalytic oxidation desulfurization;But the eutectic solvent of research report is equal at present For two components, and organic acid or strong acid are used, there is volatility and corrosivity.
Summary of the invention
In view of the deficiencies of the prior art, present invention seek to address that one of described problem, it is molten to provide a kind of three component eutectic The method of agent catalytic oxidation desulfurization;Reaction condition of the present invention is mild, easy to operate, can effectively remove the sulfide in oil product.
In order to achieve the goal above, operating procedure of the invention is as follows:
(1) it prepares eutectic solvent: quaternary ammonium salt Huo quaternary alkylphosphonium salt, boric acid, Organic Alcohol being mixed, eutectic solvent is obtained;
(2) sulfide is dissolved in dodecane, is made into the fuel oil of different sulfur contents;Then at normal temperatures and pressures, will The eutectic solvent mixing of fuel oil and step (1) preparation, adds hydrogen peroxide, is extracted at a certain temperature, reaction knot Shu Hou, since two-phase is presented in eutectic solvent and fuel oil, by simply separating the fuel oil after can be obtained desulfurization;Fuel After oil separation, water mixing is added in liquid of the remainder containing eutectic solvent, since eutectic solvent is dissolved in water, and sulfide And its reaction product is not soluble in water, is distilled by separating water phase, goes after moisture removal to recycle and obtains eutectic solvent.
Preferably, step (1) the quaternary ammonium salt Huo quaternary alkylphosphonium salt, boric acid, Organic Alcohol molar ratio be 1:0.1~3:0.1~ 3。
Preferably, the structural formula of step (1) described quaternary ammonium salt is as follows:
The quaternary alkylphosphonium salt structural formula is as follows:
R1-R4For the alkyl chain of hydrogen, saturated alkyl chain or hydroxyl.
Preferably, step (1) the quaternary ammonium salt Huo quaternary alkylphosphonium salt is tetramethyl ammonium chloride, tri-n-octyl methyl ammonium chloride, 12 Alkyl trimethyl ammonium bromide, tributyl-methyl phosphonium ammonium bromide or three hexyl tetradecane Ji phosphonium chlorides.
Preferably, step (1) Organic Alcohol is saturated alcohols, including monohydric alcohol, dihydric alcohol, polyalcohol or molecular weight are less than 1000 polyethylene glycol.
Preferably, step (2) sulfide is dibenzothiophenes, 4-MDBT or 4,6- dimethyl hexichol Bithiophene, the sulfur content of the fuel oil are 5ppm~1000ppm.
Preferably, mass ratio 1~50:1~5 of step (2) fuel oil and eutectic solvent.
Preferably, step (2) hydrogen peroxide concentration is 10wt%~30wt%, hydrogen peroxide and Sulfur content in Fuel Oil compound object The ratio between amount of matter is 2~10:1.
Preferably, the temperature of step (2) described extraction is 0 DEG C~80 DEG C, and the time is 10min~480min.
Preferably, the volume ratio of step (2) the remaining liquid containing eutectic solvent and water is 1:1~5.
Beneficial effects of the present invention:
(1) present invention has synthesized a kind of three component boric acid class eutectic solvents, this still belongs to the first time in field of oxidative desulphurization, benefit The eutectic solvent prepared with boric acid is more environmentally protective;It prepares eutectic solvent and 99.5% is reached to the removal efficiency of sulphur, have Higher catalytic oxidation desulfurization performance;Also, the recycling of eutectic solvent can be realized by simple method after reaction, Realize recycling for eutectic solvent.
(2) eutectic solvent preparation disclosed by the invention is simple, one-step synthesis method;And raw material is cheap and easy to get, reactant Utilization efficiency 100%.
Specific embodiment
The present invention is illustrated with following embodiment, but the present invention is not limited to the following embodiments, is not departing from the front and back ancestor Under the range of purport, change is included in technical scope of the invention.
Embodiment 1:
(1) eutectic solvent 1 is prepared with molar ratio 1:0.1:1 by tetramethyl ammonium chloride, boric acid, ethylene glycol (DES1);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g The DES1 of 0.1g is added in the fuel oil of sulfur content 500ppm, adds 10wt%H2O2, H2O2With Sulfur content in Fuel Oil compound (DBT) the ratio between amount of substance is 2:1, and eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is molten to be dissolved in eutectic In agent;At 0 DEG C after magnetic agitation 30min, fuel oil is isolated, using the content of DBT in GC-FID detection oil, passes through calculating The removal efficiency of sulphur is 31.3%;
(3) after fuel oil separation, 1 times of body the recycling of eutectic solvent: is added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 2:
(1) eutectic solvent is prepared with molar ratio 1:1:0.1 by tri-n-octyl methyl ammonium chloride, boric acid, polyethylene glycol 200 No. 2 (DES2);
(2) 4-MDBT (4-MDBT) is dissolved in dodecane, with the combustion for being 500ppm as sulfur content Material oil;1g DES2,20wt%H are added into the fuel oil (4-MDBT) of 5g sulfur content 500ppm2O2, H2O2With Sulfur content in Fuel Oil The ratio between amount of substance of compound (4-MDBT) is 4:1, and eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in low In congruent melting solvent;At 20 DEG C after magnetic agitation 60min, fuel oil is isolated, is contained using 4-MDBT in GC-FID detection oil Amount, the removal efficiency by calculating sulphur are 52.5%;
(3) after fuel oil separation, 2 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 3:
(1) eutectic solvent 3 are prepared with molar ratio 1:2:2 by dodecyl trimethyl ammonium bromide, boric acid, glycerine (DES3);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g 5g DES3,30wt%H are added in the fuel oil (DBT) of sulfur content 500ppm2O2(H2O2With the substance of Sulfur content in Fuel Oil compound The ratio between amount is 6:1), eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in eutectic solvent;At 50 DEG C After magnetic agitation 8h, fuel oil is isolated, using the content of DBT in GC-FID detection oil, the removal efficiency by calculating sulphur is 99.5%;
(3) after fuel oil separation, 3 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 4:
(1) eutectic solvent 3 are prepared with molar ratio 1:2:2 by dodecyl trimethyl ammonium bromide, boric acid, glycerine (DES3);
(2) 4,6- dimethyl Dibenzothiophene (4,6-DMDBT) is dissolved in dodecane, with being as sulfur content The fuel oil of 500ppm;5g DES3,30wt%H are added into the fuel oil (4,6-DMDBT) of 5g sulfur content 500ppm2O2 (H2O2Be 6:1 with the ratio between the amount of substance of Sulfur content in Fuel Oil compound), eutectic solvent is mutually in lower layer at this time, oil mutually on upper layer, H2O2It is dissolved in eutectic solvent;At 80 DEG C after magnetic agitation 8h, fuel oil is isolated, is detected 4 in oil using GC-FID, The content of 6-DMDBT, the removal efficiency by calculating sulphur are 89.5%;
(3) after fuel oil separation, 4 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 5:
(1) tributyl-methyl phosphonium ammonium bromide, boric acid, cetomacrogol 1000 are prepared into eutectic solvent 4 with molar ratio 1:3:3 Number (DES4);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g 5g DES4,30wt%H are added in the fuel oil (DBT) of sulfur content 500ppm2O2(with the amount of the substance of Sulfur content in Fuel Oil compound it Than for 10:1), eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in eutectic solvent;The magnetic at 50 DEG C After power stirs 3h, fuel oil is isolated, using the content of DBT in GC-FID detection oil, the removal efficiency by calculating sulphur is 99.2%;
(3) after fuel oil separation, 5 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 6:
(1) tributyl-methyl phosphonium ammonium bromide, boric acid, cetomacrogol 1000 are prepared into eutectic solvent 4 with molar ratio 1:3:3 Number (DES4);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g 5g DES4,30wt%H are added in the fuel oil (DBT) of sulfur content 5ppm2O2(H2O2With the amount of the substance of Sulfur content in Fuel Oil compound The ratio between be 6:1), eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in eutectic solvent;The magnetic at 50 DEG C After power stirs 3h, fuel oil is isolated, using the content of DBT in GC-FID detection oil, the removal efficiency by calculating sulphur is 99.9%;
(3) after fuel oil separation, 3 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 7:
(1) tributyl-methyl phosphonium ammonium bromide, boric acid, cetomacrogol 1000 are prepared into eutectic solvent 4 with molar ratio 1:3:3 Number (DES4);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g 5g DES4,30wt%H are added in the fuel oil (DBT) of sulfur content 1000ppm2O2(the amount with the substance of Sulfur content in Fuel Oil compound The ratio between be 6:1), eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in eutectic solvent;The magnetic at 60 DEG C After power stirs 3h, fuel oil is isolated, using the content of DBT in GC-FID detection oil, the removal efficiency by calculating sulphur is 98.7%;
(3) after fuel oil separation, 2 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Embodiment 8:
(1) that three hexyl tetradecane Ji phosphonium chlorides, boric acid, polyethylene glycol 200 are prepared eutectic with molar ratio 1:3:3 is molten Agent 4 (DES5);
(2) dibenzothiophenes (DBT) is dissolved in dodecane, with the fuel oil for being 500ppm as sulfur content;To 5g 5g DES5,30wt%H are added in the fuel oil (DBT) of sulfur content 500ppm2O2(with the amount of the substance of Sulfur content in Fuel Oil compound it Than for 8:1), eutectic solvent is mutually in lower layer at this time, and oil is mutually in upper layer, H2O2It is dissolved in eutectic solvent;The magnetic force at 60 DEG C After stirring 3h, fuel oil is isolated, using the content of DBT in GC-FID detection oil, the removal efficiency by calculating sulphur is 98.9%;
(3) after fuel oil separation, 5 times of bodies the recycling of eutectic solvent: are added in the remaining liquid containing eutectic solvent Long-pending water mixing, since eutectic solvent is dissolved in water, and sulfide and its reaction product are not soluble in water, are carried out by separation water phase Distillation, goes after moisture removal to recycle and obtains eutectic solvent.
Illustrate: above embodiments are only to illustrate the present invention and not limit the technical scheme described by the invention;Therefore, Although this specification is referring to above-mentioned each embodiment, the present invention has been described in detail, the common skill of this field Art personnel should be appreciated that and still can modify to the present invention or equivalent replacement;And all do not depart from spirit of the invention and The technical solution and its improvement of range, should all cover in scope of the presently claimed invention.

Claims (9)

1. a kind of method of three component eutectic solvent catalysis oxidation fuel desulfurations, which is characterized in that carry out as steps described below:
(1) it prepares eutectic solvent: quaternary ammonium salt Huo quaternary alkylphosphonium salt, boric acid, Organic Alcohol being mixed, eutectic solvent is obtained;
(2) sulfide is dissolved in dodecane, is made into the fuel oil of different sulfur contents;Then at normal temperatures and pressures, by fuel The eutectic solvent mixing of oil and step (1) preparation, adds hydrogen peroxide, is extracted at a certain temperature, after reaction, Since two-phase is presented in eutectic solvent and fuel oil, by simply separating the fuel oil after can be obtained desulfurization;Fuel oil From rear, water mixing is added in liquid of the remainder containing eutectic solvent, is distilled, is gone after moisture removal i.e. by separating water phase Recycling obtains eutectic solvent.
2. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In the molar ratio of, step (1) the quaternary ammonium salt Huo quaternary alkylphosphonium salt, boric acid, Organic Alcohol be 1:0.1~3:0.1~3;The quaternary ammonium salt Structural formula it is as follows:
The quaternary alkylphosphonium salt structural formula is as follows:
R1-R4For the alkyl chain of hydrogen, saturated alkyl chain or hydroxyl.
3. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1 or 2, feature It is, the quaternary ammonium salt Huo quaternary alkylphosphonium salt includes tetramethyl ammonium chloride, tri-n-octyl methyl ammonium chloride, trimethyl bromination Ammonium, tributyl-methyl phosphonium ammonium bromide or three hexyl tetradecane Ji phosphonium chlorides.
4. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In the Organic Alcohol is saturated alcohols, the polyethylene glycol including monohydric alcohol, dihydric alcohol, polyalcohol or molecular weight less than 1000.
5. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In step (2) sulfide is dibenzothiophenes, 4-MDBT or 4, and 6- dimethyl Dibenzothiophene is described The sulfur content of fuel oil is 5ppm~1000ppm.
6. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In mass ratio 1~50:1~5 of step (2) fuel oil and eutectic solvent.
7. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In step (2) hydrogen peroxide concentration is 10wt%~30wt%, and the ratio between the amount of hydrogen peroxide and Sulfur content in Fuel Oil compound substance is 2:1~10:1.
8. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In the temperature of step (2) described extraction is 0 DEG C~80 DEG C, and the time is 10min~480min.
9. a kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration according to claim 1, feature exist In the volume ratio of step (2) the remaining liquid containing eutectic solvent and water is 1:1~5.
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CN112755964A (en) * 2020-12-18 2021-05-07 辽宁科技大学 Active carbon desulfurizer loaded with quaternary phosphorus-based eutectic solvent and preparation and use methods thereof
CN113046109A (en) * 2021-03-11 2021-06-29 山西中科化美科技有限责任公司 Preparation method and application of low-sulfur low-nitrogen environment-friendly asphalt
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CN114887659A (en) * 2022-03-21 2022-08-12 江苏大学 Metal-phosphoric acid coordination type eutectic solvent and application thereof in catalytic oxidation fuel oil desulfurization

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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
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CN112755964B (en) * 2020-12-18 2023-08-15 辽宁科技大学 Active carbon desulfurizing agent loaded with Ji Linji eutectic solvent and preparation and use methods thereof
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CN114887659A (en) * 2022-03-21 2022-08-12 江苏大学 Metal-phosphoric acid coordination type eutectic solvent and application thereof in catalytic oxidation fuel oil desulfurization
CN114887659B (en) * 2022-03-21 2023-08-04 江苏大学 Metal-phosphoric acid coordination eutectic solvent and application thereof in catalytic oxidation fuel desulfurization

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