CN109694723A - The eutectic solvent and method of non basic nitrogen are extracted from analog gasoline - Google Patents
The eutectic solvent and method of non basic nitrogen are extracted from analog gasoline Download PDFInfo
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- CN109694723A CN109694723A CN201811608805.9A CN201811608805A CN109694723A CN 109694723 A CN109694723 A CN 109694723A CN 201811608805 A CN201811608805 A CN 201811608805A CN 109694723 A CN109694723 A CN 109694723A
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- eutectic solvent
- basic nitrogen
- analog gasoline
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- non basic
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 116
- 230000005496 eutectics Effects 0.000 title claims abstract description 82
- 239000002904 solvent Substances 0.000 title claims abstract description 76
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000000605 extraction Methods 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000284 extract Substances 0.000 claims abstract description 17
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims abstract description 14
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 6
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 description 43
- GTUVXOOHBUUGBH-UHFFFAOYSA-N furan;methanol Chemical compound OC.C=1C=COC=1 GTUVXOOHBUUGBH-UHFFFAOYSA-N 0.000 description 29
- 238000004088 simulation Methods 0.000 description 18
- 238000013019 agitation Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000295 fuel oil Substances 0.000 description 7
- 150000002475 indoles Chemical class 0.000 description 7
- 238000010907 mechanical stirring Methods 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000005554 pickling Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 150000004042 3-pyrrolidinones Chemical class 0.000 description 1
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- -1 nitrogenous compound Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C10G21/27—Organic compounds not provided for in a single one of groups C10G21/14 - C10G21/26
Landscapes
- 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)
- Extraction Or Liquid Replacement (AREA)
Abstract
The present invention relates to the technical field for extracting non basic nitrogen from analog gasoline, the eutectic solvent and method that non basic nitrogen is extracted from analog gasoline are disclosed.The eutectic solvent is to react hydrogen bond receptor quaternary ammonium salt and hydrogen bond donor 2- furancarbinol heating stirring that molar ratio is 1:2, and the eutectic solvent of non basic nitrogen in extraction analog gasoline is made；The quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, 4-propyl ammonium chloride or 4-propyl bromide.The extraction efficiency that the eutectic solvent extracts non basic nitrogen in analog gasoline is high, extractant usage amount is low, makes it possible that eutectic solvent extracts non basic nitrogen in gasoline and realizes industrialization.
Description
Technical field
The present invention relates to eutectic solvents and method that non basic nitrogen is extracted from analog gasoline.
Background technique
Fuel resource is China's important one of engine fuel at present, but wherein the presence of nitrogenous compound to production and
Environment causes to seriously endanger, and not only reduces the anti-oxidative stability of oil product, but also influence the storage and service performance of oil product.It is nitrogenous
The fuel burning of compound generates NOX, acid rain is formed, is to cause one of primary pollution source of environmental pollution.To solve to work as front ring
Border pollution weight, administers difficult problem, there is an urgent need to a kind of efficient fuel oil clean methods.Fuel oil denitrogenation skill traditional at present
Art has: hydrodenitrogeneration, absorption denitrogenation, pickling denitrogenation and extraction denitrogenation.Wherein hydrodenitrogeneration technology, although high-efficient, institute
The severe reaction conditions needed, equipment investment is big, and operating cost is high；Adsorbent amount needed for adsorbing denitrogenation technology is more, operation is numerous
Weight, reuse difficulty etc.；Pickling denitrogenation technology is undesirable to the removing of non basic nitrogen compound in fuel oil；Extract denitrogenation technology behaviour
Work is simple, energy consumption is low, separative efficiency is good, therefore innovates novel fuel extraction denitrogenation technology and be of great significance.
The extractant being commonly used is organic solvent, but organic solvent is readily volatilized, high with oil product mutual solubility, dirty
Therefore contaminating oil product is a kind of not environment friendly type extractant.Eutectic solvent (Deep eutectic solvent, DES) is made
For a kind of ionic liquid analog, have many advantages, such as that cheap and easy to get, designability is strong, range of viscosities is wide, environmental pollution is small,
Has application in terms of fuel oil extracts denitrogenation, for example in 2015, MC Ali etc. was supplied using ethanedioic acid, phenylacetic acid etc. as hydrogen bond
Body is synthesized eight kinds of DES using choline chloride etc. as hydrogen bond receptor, reports the fuel oil denitrogenation method based on DES for the first time, can pass through
Above-mentioned eutectic solvent removal alkalinity and non basic nitrogen compound.
But many prior arts, during using eutectic solvent extraction fuel oil, extractant and fuel oil ratio exist mostly
Within the scope of 2:1-1:2, extractant usage amount is big, and economic benefit is low, and extraction yield is not high, is unfavorable for broad scale research and industry is raw
It produces；The raw material of simultaneously synthesizing eutectic solvent is numerous, and the type of eutectic solvent is also very more, therefore the orientation of eutectic solvent point
There are limitations for class research.Inventor, which originates, has attempted the raw materials of many eutectic solvents, and obtained extractant is from simulation vapour
When extracting non basic nitrogen in oil, some solvent extraction efficiency is extremely low, the extraction basic nitrogen that some extractants can only be selective, right
The effect of extracting of non basic nitrogen is bad；In addition, almost all of extractant is in extraction, oil ratio is very big, and extractant uses
Amount is big, and economic benefit is low, is unfavorable for broad scale research and industrial production, and inventor almost abandons and extracts to from analog gasoline
The searching of the eutectic solvent of non basic nitrogen.With the progress of test, the pleasantly surprised discovery of inventor, using particular types and ratio
Hydrogen bond receptor and hydrogen bond donor, strict control response parameter can obtain the extraction that extractant usage amount is few, effect of extracting is splendid
The eutectic solvent of negated basic nitrogen.
Summary of the invention
Extraction efficiency in order to solve non basic nitrogen in eutectic solvent in the prior art extraction analog gasoline is low, extraction
The problem of agent usage amount height causes extraction to can not achieve broad scale research and industrial production, the present invention provides extract in analog gasoline
The eutectic solvent and method of negated basic nitrogen.
In order to solve the above-mentioned technical problem, the invention adopts the following technical scheme:
The eutectic solvent and method of non basic nitrogen are extracted in analog gasoline, molar ratio is the hydrogen bond receptor quaternary ammonium salt of 1:2
It is reacted with hydrogen bond donor 2- furancarbinol heating stirring, the eutectic solvent of non basic nitrogen in extraction analog gasoline is made；It is described
Quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, 4-propyl ammonium chloride or 4-propyl bromide.
The reaction temperature that the eutectic solvent of non basic nitrogen is extracted in analog gasoline provided by the invention is 90 DEG C, when reaction
Between be 1h, reaction equation is as follows, and tetrabutylammonium chloride [TBAC] is linked together with 2- furancarbinol [FAL] by hydrogen bond
's.
The present invention also provides the method using non basic nitrogen in eutectic solvent extraction analog gasoline, the eutectic is molten
Agent and analog gasoline mass ratio are 1:10, to extract non basic nitrogen in analog gasoline after the two is stirred；Preferably, described to stir
Mixing rate is 400-800r/min, and the temperature of the extraction is 20-35 DEG C, extraction time 15-20min.
The eutectic solvent of the invention can be regenerated by simple extracting process, obtain regenerated eutectic solvent.
Preferably, the preparation method of the regenerated eutectic solvent is the eutectic of non basic nitrogen into multiple extraction analog gasoline
Isometric water/alcohol mixture is added in solvent, adds acetonitrile Hui Cui, after extracted several times, 50 DEG C of vacuum revolvings obtain weight
Raw eutectic solvent.
Compared with the extractant of non basic nitrogen in extraction gasoline in the prior art, extract in analog gasoline provided by the invention
The biggest advantage of the eutectic solvent of negated basic nitrogen is to use a small amount of extractant (oil ratio 1:10) that can extract mould
Non basic nitrogen in quasi- gasoline, and the extraction yield of non basic nitrogen, close to 100%, extractant usage amount is few, high financial profit, extraction
It takes rate high, is conducive to broad scale research and industrial production, it should be noted that extracting non-alkali in analog gasoline provided by the invention
Property nitrogen eutectic solvent it is bad to the effect of extracting of basic nitrogen, can only selectivity extraction analog gasoline in non basic nitrogen；
The eutectic solvent extracting power of extraction non basic nitrogen provided by the invention is strong, the extraction efficiency of extractant after continuous extraction 10 times
Still it is able to maintain 82% or more；The eutectic solvent extracting power of extraction non basic nitrogen provided by the invention is strong, and passes through
After several secondary extractions, nitrogen content can be lower than 0.1ppm；The eutectic solvent of extraction non basic nitrogen provided by the invention can recycle
Using multiple, the extractant after living again is subjected to extraction denitrogenation, same steps again, the eutectic solvent can be recycled 6
Secondary, denitrification percent does not change substantially.
Detailed description of the invention
Fig. 1 is [TBAC] [FAL] in embodiment 12Infrared spectrogram；
Fig. 2 is [TBAC] [FAL] of embodiment 12's1H NMR(CDCl3) spectrogram；
Fig. 3 is [TBAC] [FAL] of embodiment 12TG-DTG spectrogram.
Specific embodiment
The invention discloses eutectic solvents and method that non basic nitrogen is extracted in analog gasoline, and those skilled in the art can
To use for reference present disclosure, it is suitably modified realization of process parameters.In particular, it should be pointed out that all similar substitutions and modifications are to this
It is it will be apparent that they are considered as including in the present invention for the technical staff of field.Method and application of the invention
Be described by preferred embodiment, related personnel obviously can not depart from the content of present invention, in spirit and scope it is right
Method described herein and application are modified or appropriate changes and combinations, carry out implementation and application the technology of the present invention.
The preparation of the eutectic solvent of non basic nitrogen is extracted in 1 analog gasoline of embodiment
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, by the mass ratio of the material n (hydrogen bond receptor): n (hydrogen
Key donor)=1:2 ratio, the tetrabutylammonium chloride of 0.1mol, the 2- furancarbinol of 0.2mol is added, this system is installed on
In oil bath pan, 90 DEG C are heated to, reacts 1h under conditions of 800r/min, obtaining light yellow uniform liquid is extractant
[TBAC][FAL]2, the extractant is subjected to infrared spectroscopy, nuclear magnetic resonance, thermogravimetric analysis detection, testing result is shown in figure respectively
1, Fig. 2 and Fig. 3.
Fig. 1 shows, the stretching vibration peak of O-H by raw material [FAL] (b) curve 3354cm-1It is moved to product [TBAC]
[FAL]2(a) 3251cm of curve-1Place, hence it is evident that it is mobile to lower wave number section, and peak type obviously broadens, and illustrates product [TBAC]
[FAL]2(a) there is hydrogen bond generation in；Meanwhile [TBAC] [FAL]2(a) all characteristic peaks of its hydrogen bond donor [FAL] (b) are kept；
Fig. 2 shows, [TBAC] [FAL]2(c) with [TBAC] (a) in N+Connected-CH2Chemical shift becomes 3.30 from 3.37, this is
Due to the Cl in [TBAC] (a)-O-the H-shaped of [FAL] (b) is at hydrogen bond, N+Interaction between Cl- weakens；Meanwhile
The resonance signal of the O-H of [FAL] (b) becomes 2.59 from 2.64, and chemical shift is mobile to High-Field, and chemical shift becomes smaller.It shows
[TBAC][FAL]2(c) hydrogen bond is formed between [FAL] (b) and [TBAC] (a) in.Thermogravimetric analysis is carried out to above-mentioned extractant, point
Analysis result is shown in Fig. 3.Fig. 3 shows, [TBAC] [FAL]2Weightless in 110 DEG C of beginnings, 239 DEG C are decomposed completely, illustrate [TBAC] [FAL]2
Be not suitable for extracting non basic nitrogen from analog gasoline at 110 DEG C or more.
The preparation of the eutectic solvent of non basic nitrogen is extracted in 2 analog gasoline of embodiment
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, by the mass ratio of the material n (hydrogen bond receptor): n (hydrogen
Key donor)=1:2 ratio, the tetrabutylammonium bromide of 0.2mol, the 2- furancarbinol of 0.4mol is added, this system is installed on
In oil bath pan, 90 DEG C are heated to, reacts 1h under conditions of 800r/min, obtaining light yellow uniform liquid is extractant
[TBAB][FAL]2。
The preparation of the eutectic solvent of non basic nitrogen is extracted in 3 analog gasoline of embodiment
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, by the mass ratio of the material n (hydrogen bond receptor): n (hydrogen
Key donor)=1:2 ratio, the 4-propyl ammonium chloride of 0.1mol, the 2- furancarbinol of 0.2mol is added, this system is installed on
In oil bath pan, 90 DEG C are heated to, reacts 1h under conditions of 800r/min, obtaining light yellow uniform liquid is extractant
[TPAC][FAL]2。
The preparation of the eutectic solvent of non basic nitrogen is extracted in 4 analog gasoline of embodiment
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, by the mass ratio of the material n (hydrogen bond receptor): n (hydrogen
Key donor)=1:2 ratio, the 4-propyl bromide of 0.1mol, the 2- furancarbinol of 0.2mol is added, this system is installed on
In oil bath pan, 90 DEG C are heated to, reacts 1h under conditions of 800r/min, obtaining light yellow uniform liquid is extractant
[TPAB][FAL]2。
The method that embodiment 5 extracts non basic nitrogen in analog gasoline using eutectic solvent
It is accurately weighed in 50mL single-necked flask mass ratio m (extractant): the preparation of m (simulation oil)=1:10 embodiment 1
Eutectic solvent extractant [TBAC] [FAL]2With 150ppm indoles simulation oil, magneton is added, this system is installed on water-bath
In pot, under conditions of 30 DEG C, with the revolving speed magnetic agitation 15min of 800r/min, static 60min, is taken out suitable after reaction
Upper layer oil product is measured, with remaining nitrogen content in nitrogen instrument measurement oil product is surveyed, calculating denitrification percent is 99.90%.
It should be noted that the nitride concentration of analog gasoline has 500ppm, 300ppm or 150ppm, the concentration of nitride
Lower, the extraction difficulty of non basic nitrogen is bigger.
The method that embodiment 6 extracts non basic nitrogen in analog gasoline using eutectic solvent
It is accurately weighed in 50mL single-necked flask mass ratio m (extractant): the preparation of m (simulation oil)=1:10 embodiment 2
Eutectic solvent extractant [TBAB] [FAL]2With 150ppm indoles simulation oil, magneton is added, this system is installed on water-bath
In pot, under conditions of 20 DEG C, with the revolving speed magnetic agitation 15min of 400r/min, static 60min, is taken out suitable after reaction
Upper layer oil product is measured, with remaining nitrogen content in nitrogen instrument measurement oil product is surveyed, calculating denitrification percent is 99.36%.
The method that embodiment 7 extracts non basic nitrogen in analog gasoline using eutectic solvent
It is accurately weighed in 50mL single-necked flask mass ratio m (extractant): the preparation of m (simulation oil)=1:10 embodiment 3
Eutectic solvent extractant [TPAC] [FAL]2With 150ppm indoles simulation oil, magneton is added, this system is installed on water-bath
In pot, under conditions of 35 DEG C, with the revolving speed magnetic agitation 20min of 800r/min, static 60min, is taken out suitable after reaction
Upper layer oil product is measured, with remaining nitrogen content in nitrogen instrument measurement oil product is surveyed, calculating denitrification percent is 99.02%.
The method that embodiment 8 extracts non basic nitrogen in analog gasoline using eutectic solvent
It is accurately weighed in 50mL single-necked flask mass ratio m (extractant): the preparation of m (simulation oil)=1:10 embodiment 4
Eutectic solvent extractant [TPAB] [FAL]2With 150ppm indoles simulation oil, magneton is added, this system is installed on water-bath
In pot, under conditions of 28 DEG C, with the revolving speed magnetic agitation 18min of 600r/min, static 60min, is taken out suitable after reaction
Upper layer oil product is measured, with remaining nitrogen content in nitrogen instrument measurement oil product is surveyed, calculating denitrification percent is 98.46%.
The method that embodiment 9 extracts non basic nitrogen in analog gasoline using eutectic solvent
It is accurately weighed in 50mL single-necked flask mass ratio m (extractant): the preparation of m (simulation oil)=1:10 embodiment 1
Eutectic solvent extractant [TBAC] [FAL]2With 500ppm indoles simulation oil, magneton is added, this system is installed on water-bath
In pot, under conditions of 20 DEG C, with the revolving speed magnetic agitation 15min of 800r/min, static 60min, is taken out suitable after reaction
Amount upper layer oil product is detected, and calculating denitrification percent is 99.61%.
The saturation extracting power of 10 eutectic solvent extractant of embodiment is tested
By embodiment 5 extract denitrogenation it is primary after, after isolating upper layer oil product, continuously add matter same as Example 5
The analog gasoline of amount, is extracted next time under the conditions of same as Example 5, same steps, is extracted after continuous extraction 10 times
Agent [TBAC] [FAL]2Extraction efficiency is still able to maintain 82% or more.
The test of the multitple extraction ability of 11 eutectic solvent extractant of embodiment
By embodiment 5 extract denitrogenation it is primary after, take out the denitrogenation gasoline on upper layer, rejoin and 5 phase of embodiment
The fresh eutectic solvent extractant [TBAC] [FAL] of homogenous quantities2In, extracted again under the conditions of same as Example 5
It takes, same steps, after 2 grades of extractions, nitrogen content can be lower than 0.1ppm.
The test of 12 eutectic solvent of embodiment recycling performance
In embodiment 5, extraction terminates, after isolating upper layer oil product, to the eutectic solvent solvent [TBAC] of lower layer
[FAL]2It is middle that isometric water/alcohol mixture is added, it adds 10mL acetonitrile and carries out Hui Cui, after Hui Cui 5 times, vacuum at 50 DEG C
It is outstanding to steam, finally obtain fresh eutectic solvent, under the conditions of same as Example 5, with the eutectic solvent lived again again into
Row extraction denitrogenation, same steps, eutectic solvent are recycled 6 times, and denitrification percent does not change substantially.
13 hydrogen bond receptor of embodiment and hydrogen bond donor proportion selection
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, the tetrabutylammonium chloride of 0.1mol is first added,
It is then respectively adding the 2- furancarbinol of 0.1mol and the 2- furancarbinol of 0.3mol, above-mentioned two system is installed on oil bath pan
In, other reaction conditions such as embodiment 1, obtaining one liquid of both of which is extractant, now makees performance detection to two kinds of extractants.
When n (hydrogen bond receptor): when n (hydrogen bond donor)=1:1, synthesized low-temperature eutectic agent, when low temperature (10 DEG C), in solidifying
Solid fraction state is used for manufactured extractant to extract denitrogenation, other reaction conditions are constant, after reusing twice, extractant quality
It reduces, and extraction efficiency is substantially reduced.Possible cause is that hydrogen bond donor ratio is very little in synthesized low-temperature eutectic agent, formation
Hydrogen bond is unstable, and during the regeneration of extractant and recycling, the fracture of part hydrogen bond, dissolving in again cannot in ethanol solution
Revert to original low-temperature eutectic agent.
When n (hydrogen bond receptor): when n (hydrogen bond donor)=1:3, measures this extractant and oil product mutual solubility is 6.21%,
In extraction process, meeting contaminated product influences oil quality.
Comparative example 1-3
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, supplied by hydrogen bond receptor listed by table 1 and hydrogen bond
Body prepares eutectic solvent, and ratio and method are same as Example 1, by the corresponding eutectic solvent being prepared and simulation
Gasoline is according to mass ratio m (extractant): m (simulation oil)=1:10 is extracted, and simulation oil is 150ppm indoles simulation oil, is added
This system is installed in water-bath by magneton, under conditions of 20 DEG C, with the revolving speed magnetic agitation 15min of 800r/min, reaction
After static 60min, take out appropriate upper layer oil product and detected, calculate corresponding denitrification percent.
The denitrification percent of the different eutectic solvent of table 1 compares
| Comparative example | Extractant (hydrogen bond receptor/hydrogen bond donor) | Denitrification percent/% |
| Comparative example 1 | Choline chloride/urea | 30.41% |
| Comparative example 2 | Tetrabutylammonium chloride/imidazoles | 90.18% |
| Comparative example 3 | Pyrrolidones/2- hydroxymethylfurans methanol | 49.63% |
1 data of table show that the denitrification effect of most common eutectic solvent is not ideal in the prior art, only four fourths
The denitrification effect for the eutectic solvent that ammonium chloride and imidazoles are prepared has reached 90%, but with it is provided by the invention low total
Molten solvent is compared, and effect of extracting is still undesirable.
Comparative example 4-8
In the 100mL three-necked flask equipped with mechanical stirring stick, thermometer, supplied by hydrogen bond receptor listed by table 2 and hydrogen bond
Body prepares aromatic alcohol eutectic solvent according to preparation method described in embodiment 1, the corresponding aromatic alcohol that will be prepared
Eutectic solvent and analog gasoline are according to mass ratio m (extractant): m (simulation oil)=1:10 is extracted, and simulation oil is
150ppm indoles simulation oil is added magneton, this system is installed in water-bath, under conditions of 20 DEG C, with 800r/min's
Revolving speed magnetic agitation 15min, static 60min, takes out appropriate upper layer oil product and is detected, calculate corresponding denitrogenation after reaction
Rate, and the state of eutectic solvent is detected, testing result is as shown in table 2.
2 aromatic alcohol eutectic extractant of table extracts analog gasoline denitrogenation result
2 data of table show that the denitrification percent of individual aromatic alcohol eutectic extractants has been more than 90%, but the extraction synthesized
Compared to furancarbinol kind of extractants, viscosity is big for agent, and the resistance being subject in mass transport process is larger, is not suitable as a kind of excellent
Extractant.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (6)
1. extracting the eutectic solvent of non basic nitrogen from analog gasoline, it is characterised in that: molar ratio is the hydrogen bond receptor season of 1:2
Ammonium salt and the reaction of hydrogen bond donor 2- furancarbinol heating stirring, are made the eutectic solvent of non basic nitrogen in extraction analog gasoline；
The quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, 4-propyl ammonium chloride or 4-propyl bromide.
2. eutectic solvent as described in claim 1, it is characterised in that: the reaction temperature of the reaction is 90 DEG C, when reaction
Between be 1h.
3. using the method for non basic nitrogen in eutectic solvent of any of claims 1 or 2 extraction analog gasoline, feature exists
In: the eutectic solvent is 1:10 with analog gasoline mass ratio, to extract non-alkaline in analog gasoline after the two is stirred
Nitrogen.
4. method as claimed in claim 3, it is characterised in that: the stirring rate is 400-800r/min, the extraction
Temperature is 20-35 DEG C, extraction time 15-20min.
5. method as claimed in claim 3, it is characterised in that: the eutectic solvent is regenerated by extracting process, is obtained again
Raw eutectic solvent.
6. method as claimed in claim 3, it is characterised in that: the preparation method of the regenerated eutectic solvent is Xiang Duo
Isometric water/alcohol mixture is added in secondary extraction analog gasoline in the eutectic solvent of non basic nitrogen, adds acetonitrile and returns
Extract, after extracted several times, 50 DEG C of vacuum revolvings, the eutectic solvent lived again.
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