CN107586554A - It is a kind of to be used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil - Google Patents
It is a kind of to be used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil Download PDFInfo
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- CN107586554A CN107586554A CN201710853084.7A CN201710853084A CN107586554A CN 107586554 A CN107586554 A CN 107586554A CN 201710853084 A CN201710853084 A CN 201710853084A CN 107586554 A CN107586554 A CN 107586554A
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- Prior art keywords
- refining agent
- thiophene
- fuel oil
- aromatic hydrocarbons
- water
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 75
- 238000007670 refining Methods 0.000 title claims abstract description 57
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000000295 fuel oil Substances 0.000 title claims abstract description 30
- 150000002897 organic nitrogen compounds Chemical class 0.000 title claims abstract description 24
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 43
- UJAUJKDQVXXVLZ-UHFFFAOYSA-M trimethyl(1-phenylheptadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCC([N+](C)(C)C)C1=CC=CC=C1 UJAUJKDQVXXVLZ-UHFFFAOYSA-M 0.000 claims abstract description 21
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002270 dispersing agent Substances 0.000 claims abstract description 12
- 239000003381 stabilizer Substances 0.000 claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006467 substitution reaction Methods 0.000 claims description 42
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000003233 pyrroles Chemical class 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 5
- 150000002475 indoles Chemical class 0.000 claims description 4
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 38
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 20
- 238000000034 method Methods 0.000 abstract description 12
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 abstract description 9
- 238000006477 desulfuration reaction Methods 0.000 abstract description 6
- 230000023556 desulfurization Effects 0.000 abstract description 6
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 59
- 238000002156 mixing Methods 0.000 description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 17
- 150000004767 nitrides Chemical group 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000000306 component Substances 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- HDUHSISAGHHYRW-UHFFFAOYSA-N [N].N1=CC=CC2=CC=CC=C21 Chemical compound [N].N1=CC=CC2=CC=CC=C21 HDUHSISAGHHYRW-UHFFFAOYSA-N 0.000 description 8
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 8
- NPPHEVSPZGYDHP-UHFFFAOYSA-N [S].C1=CC=C2SC=CC2=C1 Chemical compound [S].C1=CC=C2SC=CC2=C1 NPPHEVSPZGYDHP-UHFFFAOYSA-N 0.000 description 8
- 239000005864 Sulphur Substances 0.000 description 7
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 6
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- -1 heterocyclic nitride Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical compound [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MEUKEBNAABNAEX-UHFFFAOYSA-N hydroperoxymethane Chemical compound COO MEUKEBNAABNAEX-UHFFFAOYSA-N 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
It is used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil the invention discloses a kind of, wherein post aromatic hydrocarbons, stabilizer triethanolamine or Propylene Glycol Dimethyl Ether, dispersant neopelex or cetyl trimethyl benzyl ammonium chloride and water that described refining agent is substituted by the full hydroxyl of active component form.The post aromatic hydrocarbons that this refining agent is mainly substituted using full hydroxyl realizes deep removal to the clathration of organic nitrogen compound in fuel oil and thiophene-type sulfide, and with features such as easily recovery, green, easily operated implementations, a kind of new green environment protection, inexpensive method are provided for the advanced nitrogen of fuel oil, desulfurization.
Description
Technical field
The invention belongs to PETROLEUM PROCESSING field, and in particular to one kind is used to remove organic nitrogen compound and thiophene in fuel oil
The refining agent of class sulfide.
Background technology
One of at present, people clean the requirement more and more higher of degree to oil product, and the reason for cause oil quality to be deteriorated
It is nitride and sulfide in oil product be present.Nitride and sulfide in oil product are mainly heterocyclic nitride and thiophene
Class sulfide, it is difficult to remove, and has extreme influence to oil stability, inoxidizability etc.；Nitrogen oxygen is produced when burning simultaneously
Compound (NOX) and oxysulfide (SOX), air pollution can be caused.It can be seen that realize that the advanced nitrogen of oil product, desulfurization are significant.
At present, oil denitrification, the technique of desulfurization have hydrogenation technique and Non-adding hydrogen.Wherein, hydrogenation technique is ripe, application
It is relatively broad, but the octane number to oil product, greasy property and stability etc. can cause damage.And existing Non-adding hydrogen (extraction
Follow the example of, absorption method and oxidizing process etc.) although hardly being caused damage to the octane number of oil product, greasy property and stability etc.,
Removal efficiency is not high, needs exploitation New-type fuel oil product Non-hydrogenation technology, desulfurization technology badly.Post aromatic hydrocarbons is as supermolecule main block, tool
There are high degree of symmetry, rigid structure and excellent molecule distinguishability, be usually used in water process (CN201610079351.5；
CN201610176308.0；CN201410631270.2；CN201610266521.0), fluorescence identifying
(CN201610199037.0；CN201510558495.4；CN201610199027.7；CN201610909838.1) etc., but it is right
The removing of organic nitrogen compound and thiophene-type sulfide has no report in fuel oil.Organic nitrogen compound in fuel oil is mainly
Pyridine, aniline, pyrroles, indoles, quinoline, thiophene-type sulfide is mainly thiophene, benzothiophene, dibenzothiophenes, with post aromatic hydrocarbons
Matching it is good.Post [5] aromatic hydrocarbons of full hydroxyl substitution and post [6] aromatic hydrocarbons of full hydroxyl substitution are solvable in water, and do not dissolve in
Fuel oil, while the stabilizer such as triethanolamine, Propylene Glycol Dimethyl Ether can effectively improve stability of the post aromatic hydrocarbons in water, pass through
The dispersants such as neopelex, cetyl trimethyl benzyl ammonium chloride can promote aqueous phase and oil product liquid-liquid diphase to contact
More fully, phase transfer efficiency and separative efficiency are improved.Contemplate based on more than, post [5] aromatic hydrocarbons that the full hydroxyl of active component is substituted
Or post [6] aromatic hydrocarbons, stabilizer triethanolamine or the Propylene Glycol Dimethyl Ether of full hydroxyl substitution, dispersant neopelex or
Cetyl trimethyl benzyl ammonium chloride and water composition refining agent, for organic nitrogen compound in fuel oil and thiophene-type sulfide
Removing, have easily recovery, it is green, it is easily operated implement etc. feature, for the advanced nitrogen of fuel oil, denitrogenation provides one kind newly
Green, the inexpensive method of type.
The content of the invention
It is used to remove the essence of organic nitrogen compound and thiophene-type sulfide in fuel oil it is an object of the invention to provide a kind of
Preparation.The refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil is removed, post [5] aromatic hydrocarbons based on the substitution of full hydroxyl
With main organic nitrogen compound (pyridine, aniline, pyrroles, indoles, quinoline) in post [6] aromatic hydrocarbons and the fuel oil of the substitution of full hydroxyl and
The matching of thiophene-type sulfide (thiophene, benzothiophene, dibenzothiophenes) is good, and supermolecule clathration easily occurs in the two,
Post [5] aromatic hydrocarbons of full hydroxyl substitution and post [6] aromatic hydrocarbons of full hydroxyl substitution are solvable in water simultaneously, and do not dissolve in fuel oil,
Subtractive process can be realized by the water-oil phase way of contact, the nitride in oil product, sulfide are transferred to post aromatic hydrocarbons (water
Phase) in inner chamber body, while stability of the post aromatic hydrocarbons in water is improved using stabilizers such as triethanolamine, Propylene Glycol Dimethyl Ethers, lead to
Crossing the dispersants such as neopelex, cetyl trimethyl benzyl ammonium chloride can promote aqueous phase and oil product liquid-liquid diphase to connect
Touch more fully, improve phase transfer efficiency and separative efficiency.
The present invention adopts the following technical scheme that：
It is provided by the invention a kind of for removing the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil, by
Post [5] aromatic hydrocarbons of the full hydroxyl substitution of active component or post [6] aromatic hydrocarbons, stabilizer triethanolamine or the propane diols two of the substitution of full hydroxyl
Methyl ether, dispersant neopelex or cetyl trimethyl benzyl ammonium chloride and water composition.
It is of the present invention to be used to remove in fuel oil activity in the refining agent of organic nitrogen compound and thiophene-type sulfide
Mass concentration of the component in water is 0.1~5%, and the mass fraction that stabilizer accounts for water is 0.01~0.5%, and dispersant accounts for water
Mass fraction is 0.1~0.5%.
It is of the present invention to be used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil, removing combustion
Organic nitrogen compound in material oil product has pyridine, aniline, pyrroles, indoles, quinoline, and the thiophene-type sulfide removed in fuel oil has
Thiophene, benzothiophene, dibenzothiophenes.
The preparation of the present invention for being used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil：
Using water as solvent, post [5] aromatic hydrocarbons of full hydroxyl substitution or post [6] aromatic hydrocarbons (active component) of full hydroxyl substitution are dissolved, is added
Appropriate stabilizer and dispersant, shakes up so that mass concentration of the active component in water is 0.1~5%, and stabilizer accounts for water
Mass fraction is 0.01~0.5%, and the mass fraction that dispersant accounts for water is 0.1~0.5%.
Refining agent of the present invention is used to remove the evaluation side of organic nitrogen compound and thiophene-type sulfide in fuel oil
Method is：Oil product containing finite concentration organic nitrogen compound and/or sulfide is mixed with refining agent by certain agent oil volume ratio,
(mixing speed 500rpm) certain time is stirred under normal pressure, certain removal temperature, then after standing certain time, is analyzed in oil reservoir
Nitrogen/and sulfur content.Denitrogenation or sulphur rate are calculated by formula (1)：
E%=(C0-C1)×100/C0Formula (1)
In formula (1),
The removal efficiency of E%-organic nitrogen compound or thiophene-type sulfide；
C0Nitrogen or sulphur concentration before-removing, μ gg-1；
C1Nitrogen or sulphur concentration after-removing, μ gg-1。
Refining agent of the present invention is used to remove the evaluation side of organic nitrogen compound and thiophene-type sulfide in fuel oil
In method, organic nitrogen or sulphur concentration are 50~200 μ gg-1, agent oil volume ratio is 1:5~5:1, removal temperature is 20~50 DEG C, is stirred
It is 10~120min to mix the time, and time of repose is 2~10min.
It is of the present invention to be used to remove in fuel oil the refining agent advantage of organic nitrogen compound and thiophene-type sulfide such as
Under：
Post [5] aromatic hydrocarbons of the full hydroxyl substitution of active component or the post [6] of full hydroxyl substitution in refining agent of the present invention
Aromatic hydrocarbons is green and cost is cheap, and preparation method is simple, easily operated, and refining agent is easily recycled, and is the depth of fuel oil
Spend denitrogenation, desulfurization provides a kind of new green environment protection, the method for low cost.
Brief description of the drawings
Fig. 1 be refining agent of the present invention and water to aniline nitrogen, benzothiophene sulphur removal efficiency contrast (1, refining agent E of the present invention；
2nd, water)
Embodiment
Embodiment 1
Using 50mL water as solvent, add post [5] aromatic hydrocarbons of 0.05g full hydroxyls substitution, add 0.005g triethanolamines and
0.05g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [5] aromatic hydrocarbons, three ethanol of full hydroxyl substitution
The mass concentration of amine, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 0.1%, 0.01%, 0.1%, and composition is refined
Agent A.50 μ gg will be contained-1The oil product of pyrroles's nitrogen is 1 by agent oil volume ratio with refining agent A:5 mixing, are stirred at normal pressure, 20 DEG C
30min (mixing speed 500rpm) is mixed, then after standing 2min, the removal efficiency of pyrroles's nitrogen is 20.4%.
Embodiment 2
Using 50mL water as solvent, add post [5] aromatic hydrocarbons of 0.25g full hydroxyls substitution, add 0.015g triethanolamines and
0.15g neopelexes, shake up to being completely dissolved so that post [5] aromatic hydrocarbons of full hydroxyl substitution, triethanolamine, 12
Mass concentration of the sodium alkyl benzene sulfonate in water is followed successively by 0.5%, 0.03%, 0.3%, composition refining agent B.100 μ will be contained
g·g-1The oil product of pyrroles's nitrogen is 1 by agent oil volume ratio with refining agent B:3 mixing, 120min (stirrings are stirred at normal pressure, 30 DEG C
Speed is 500rpm), then after standing 10min, the removal efficiency of pyrroles's nitrogen is 41.5%.
Embodiment 3
Using 50mL water as solvent, post [5] aromatic hydrocarbons of the full hydroxyl substitutions of 0.5g is added, adds 0.25g Propylene Glycol Dimethyl Ethers
With 0.075g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [5] aromatic hydrocarbons of full hydroxyl substitution, third
The mass concentration of glycol dimethyl ether, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 1%, 0.5%, 0.15%, group
Into refining agent C.75 μ gg will be contained-1The oil product of pyridine nitrogen is 1 by agent oil volume ratio with refining agent C:2 mixing, in normal pressure, 25
10min (mixing speed 500rpm) is stirred at DEG C, then after standing 2min, the removal efficiency of pyridine nitrogen is 32.6%.
Embodiment 4
Using 50mL water as solvent, add post [5] aromatic hydrocarbons of 1.25g full hydroxyls substitution, add 0.05g triethanolamines and
0.1g neopelexes, shake up to being completely dissolved so that post [5] aromatic hydrocarbons, triethanolamine, the dodecane of full hydroxyl substitution
Mass concentration of the base benzene sulfonic acid sodium salt in water is followed successively by 2.5%, 0.1%, 0.2%, composition refining agent D.200 μ gg will be contained-1
Pyridine nitrogen and containing 100 μ gg-1The oil product of thiophenic sulfur is 5 by agent oil volume ratio with refining agent D:1 mixing, is stirred at normal pressure, 40 DEG C
50min (mixing speed 500rpm) is mixed, then after standing 3min, pyridine nitrogen, the removal efficiency of thiophenic sulfur be followed successively by 62.6%,
41.8%.
Embodiment 5
Using 50mL water as solvent, post [5] aromatic hydrocarbons of the full hydroxyl substitutions of 1.5g is added, adds 0.035g Propylene Glycol Dimethyl Ethers
With 0.25g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [5] aromatic hydrocarbons of full hydroxyl substitution, the third two
The mass concentration of diethylene glycol dimethyl ether, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 3%, 0.07%, 0.5%, composition
Refining agent E.100 μ gg will be contained-1The oil product of aniline nitrogen is 1 by agent oil volume ratio with refining agent E:1 mixing, normal pressure, 50 DEG C
Lower stirring 40min (mixing speed 500rpm), then after standing 4min, the removal efficiency of aniline nitrogen is 47.4%.
Embodiment 6
Using 50mL water as solvent, post [5] aromatic hydrocarbons of the full hydroxyl substitutions of 2g is added, adds 0.1g triethanolamines and 0.15g
Cetyl trimethyl benzyl ammonium chloride, shake up to being completely dissolved so that post [5] aromatic hydrocarbons of full hydroxyl substitution, triethanolamine, nonyl
Mass concentration of the cetyl trimethyl benzyl ammonium chloride in water is followed successively by 4%, 0.2%, 0.3%, composition refining agent F.Will
Contain 150 μ gg-1Aniline nitrogen and contain 50 μ gg-1The oil product of benzothiophene sulphur is 3 by agent oil volume ratio with refining agent F:1
Mixing, 60min (mixing speed 500rpm) is stirred at normal pressure, 40 DEG C, then after standing 5min, aniline nitrogen, benzothiophene sulphur
Removal efficiency be followed successively by 57.4%, 52.9%.
Embodiment 7
Using 50mL water as solvent, add post [6] aromatic hydrocarbons of 2.5g full hydroxyls substitution, add 0.2g Propylene Glycol Dimethyl Ethers and
0.2g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [6] aromatic hydrocarbons, the propane diols of full hydroxyl substitution
The mass concentration of dimethyl ether, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 5%, 0.4%, 0.4%, and composition is refined
Agent G.150 μ gg will be contained-1The oil product of indole nitrogen is 2 by agent oil volume ratio with refining agent G:1 mixing, is stirred at normal pressure, 50 DEG C
90min (mixing speed 500rpm) is mixed, then after standing 5min, the removal efficiency of indole nitrogen is 41.5%.
Embodiment 8
Using 50mL water as solvent, add post [6] aromatic hydrocarbons of 1g full hydroxyls substitution, add 0.15g triethanolamines and
0.125g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [6] aromatic hydrocarbons of full hydroxyl substitution, three second
The mass concentration of hydramine, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 2%, 0.3%, 0.25%, and composition is refined
Agent H.200 μ gg will be contained-1The oil product of indole nitrogen and contain 100 μ gg-1Indole nitrogen, 100 μ gg-1The oil of benzothiophene sulphur
Product are 1 by agent oil volume ratio with refining agent H:2 mixing, 100min (mixing speed 500rpm) is stirred at normal pressure, 20 DEG C, then
After standing 6min, removal efficiency is followed successively by 40.7%, 36.7%.
Embodiment 9
Using 50mL water as solvent, post [6] aromatic hydrocarbons of the full hydroxyl substitutions of 0.35g is added, adds 0.25g Propylene Glycol Dimethyl Ethers
With 0.175g neopelexes, shake up to being completely dissolved so that post [6] aromatic hydrocarbons, the propane diols diformazan of full hydroxyl substitution
The mass concentration of ether, neopelex in water is followed successively by 0.7%, 0.5%, 0.35%, composition refining agent I.It will contain
There are 50 μ gg-1The oil product of quinoline nitrogen is 1 by agent oil volume ratio with refining agent I:4 mixing, 120min is stirred at normal pressure, 30 DEG C
(mixing speed 500rpm), then after standing 7min, the removal efficiency of quinoline nitrogen is 30.4%.
Embodiment 10
Using 50mL water as solvent, post [6] aromatic hydrocarbons of the full hydroxyl substitutions of 0.15g is added, adds 0.1g Propylene Glycol Dimethyl Ethers
With 0.225g cetyl trimethyl benzyl ammonium chlorides, shake up to being completely dissolved so that post [6] aromatic hydrocarbons of full hydroxyl substitution, third
The mass concentration of glycol dimethyl ether, cetyl trimethyl benzyl ammonium chloride in water is followed successively by 0.3%, 0.2%, 0.45%,
Form refining agent J.150 μ gg will be contained-1The oil product of quinoline nitrogen is 4 by agent oil volume ratio with refining agent J:1 mixing, normal pressure,
45min (mixing speed 500rpm) is stirred at 40 DEG C, then after standing 5min, the removal efficiency of quinoline nitrogen is 42.9%.
Embodiment 11
Using 50mL water as solvent, post [6] aromatic hydrocarbons of the full hydroxyl substitutions of 2g is added, adds 0.1g triethanolamines and 0.15g
Cetyl trimethyl benzyl ammonium chloride, shake up to being completely dissolved so that post [6] aromatic hydrocarbons of full hydroxyl substitution, triethanolamine, ten
Mass concentration of the six alkyl trimethyl benzyl ammonium chlorides in water is followed successively by 4%, 0.2%, 0.3%, composition refining agent K.It will contain
There are 125 μ gg-1Quinoline nitrogen or 100 μ gg-1The oil product of dibenzothiophenes sulphur is 1 by agent oil volume ratio with refining agent K:1 is mixed
Close, 120min (mixing speed 500rpm) is stirred at normal pressure, 25 DEG C, then after standing 10min, quinoline nitrogen, dibenzothiophenes
The removal efficiency of sulphur is followed successively by 50.7%, 47.8%.
Implement comparative example 1
100 μ gg will be contained-1Aniline nitrogen or 100 μ gg-1The oil product of benzothiophene sulphur is with refining agent E or water by agent oil
Volume ratio is 5:1 mixing, stirs 90min (mixing speed 500rpm) at normal pressure, 20 DEG C, then after standing 10min, analyzes benzene
The removal efficiency of amine nitrogen, benzothiophene sulphur, as a result as shown in Figure 1.
It will be seen from figure 1 that refining agent of the present invention has excellent removal effect, main denitrogenation, desulfurization are played in refining agent
Post [5] aromatic hydrocarbons of the full hydroxyl substitution of effect, water also have certain removal effect (aniline is slightly dissolved in water, except benzothiophene),
Stabilizer and dispersant enhance post [5] aromatic hydrocarbons inclusion removing aniline of full hydroxyl substitution and the performance of benzothiophene；Thus may be used
See, refining agent of the present invention is not the simple combination of several materials, but passes through the removing component for thinking over and filtering out, collaboration
Play denitrogenation, desulfidation.
Implement comparative example 2
By the oil product containing aniline nitrogen, pyridine nitrogen, pyrroles's nitrogen, (total nitrogen content is 60 μ gg-1, three kinds of nitrogen content ratios are
1:1:1) or the oil product containing indole nitrogen, quinoline nitrogen (total nitrogen content is 60 μ gg-1, two kinds of nitrogen content ratios are 1:1) or contain
Thiophenic sulfur, benzothiophene sulphur, (total sulfur content is 60 μ gg to the oil product of dibenzothiophenes sulphur-1, three kinds of sulfur content ratios are 1:1：
1) it is 3 with refining agent F or refining agent K agent oil volume ratio:1 mixing, at normal pressure, 20 DEG C stirring 120min, (mixing speed is
500rpm), then after standing 10min, refining agent of the present invention is contrasted to mixed nitride thing, the removal effect of sulfide oil product, as a result
It is shown in Table 1.
The refining agent mixed nitride thing of the present invention of table 1, the removal effect of sulfide oil product
As can be seen from Table 1, refining agent of the present invention can effectively remove mixed nitride thing, the sulfide in oil product, send out simultaneously
The post aromatic hydrocarbons of the existing full hydroxyl substitution of active component has removing selectivity, and post [5] aromatic hydrocarbons of full hydroxyl substitution is to containing monocyclic knot
Nitride, the sulfide removal effect of structure are good, and post [6] aromatic hydrocarbons of full hydroxyl substitution is to containing polycyclic (bicyclic or three rings) structure
Nitride, sulfide removal effect it is good.
Implement comparative example 3
By the oil product containing aniline nitrogen, pyridine nitrogen, pyrroles's nitrogen, thiophenic sulfur, (total nitrogen, sulfur content are 80 μ gg-1, Mei Zhonghan
Amount ratio is 1:1:1:1) or containing indole nitrogen, quinoline nitrogen, benzothiophene sulphur, dibenzothiophenes sulphur oil product (total nitrogen, sulfur content
For 80 μ gg-1, every kind of content ratio is 1:1:1:1) it is 5 with refining agent F or refining agent K agent oil volume ratio:1 mixing, normal
Pressure, stir 90min at 20 DEG C, then after standing 10min, contrast refining agent of the present invention to mixed nitride thing, sulfide oil product it is total
Removal effect, it the results are shown in Table shown in 2.
2 refining agent of the present invention of table is to mixing nitrogen, the removal effect of sulfide oil product
From table 2 it can be seen that oil product of the refining agent pair of the present invention simultaneously containing sulfide and nitride still has preferably
Removal effect.In actual applications, should be according to the type and content of sulfide in oil product and nitride, in reasonably optimizing refining agent
The ratio of active component, stabilizer and dispersant, sulfide and nitride in oil product are effectively removed, reach the mesh of oil refinery
's.
Obviously, above-described embodiment is only intended to clearly illustrate example, and not real to the refining agent of the present invention
Apply the restriction of mode.For those of ordinary skill in the field, can also make on the basis of the above description other
Various forms of changes or variation.Here need not, all embodiments can not also be enumerated.And thus extend out
Among obvious changes or variations is still in the protection domain of the invention.
Claims (3)
1. a kind of be used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil, it is characterised in that by living
Property post [5] aromatic hydrocarbons of component full hydroxyl substitution or post [6] aromatic hydrocarbons, stabilizer triethanolamine or the propane diols diformazan of the substitution of full hydroxyl
Ether, dispersant neopelex or cetyl trimethyl benzyl ammonium chloride and water composition.
2. according to claim 1 be used to remove the refining agent of organic nitrogen compound and thiophene-type sulfide in fuel oil,
Characterized in that, mass concentration of the active component in water is 0.1~5% in refining agent, the mass fraction that stabilizer accounts for water is
0.01~0.5%, the mass fraction that dispersant accounts for water is 0.1~0.5%.
3. it is used to remove the refined of organic nitrogen compound and thiophene-type sulfide in fuel oil according to claim 1-2
Agent, it is characterised in that the organic nitrogen compound in removing fuel oil has pyridine, aniline, pyrroles, indoles, quinoline, removes fuel oil
Thiophene-type sulfide in product has thiophene, benzothiophene, dibenzothiophenes.
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| CN111362774A (en) * | 2020-03-03 | 2020-07-03 | 浙江大学 | Application of ethoxy column [6] arene crystal material in selective adsorption of heterocyclic compound |
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| CN101544907A (en) * | 2008-03-26 | 2009-09-30 | 通用电气公司 | Oxidative desulfurization of fuel oil |
| CN105087050A (en) * | 2015-09-11 | 2015-11-25 | 中国石油大学(华东) | Fuel oil product denitrifier using supramolecular inclusion effect and application method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101544907A (en) * | 2008-03-26 | 2009-09-30 | 通用电气公司 | Oxidative desulfurization of fuel oil |
| CN105087050A (en) * | 2015-09-11 | 2015-11-25 | 中国石油大学(华东) | Fuel oil product denitrifier using supramolecular inclusion effect and application method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111362774A (en) * | 2020-03-03 | 2020-07-03 | 浙江大学 | Application of ethoxy column [6] arene crystal material in selective adsorption of heterocyclic compound |
| CN111362774B (en) * | 2020-03-03 | 2021-01-12 | 浙江大学 | Application of ethoxy column [6] arene crystal material in selective adsorption of heterocyclic compound |
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