CN103396827A - Separation method for alkali nitrogen compounds in coal liquefaction oil - Google Patents
Separation method for alkali nitrogen compounds in coal liquefaction oil Download PDFInfo
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- CN103396827A CN103396827A CN2013103298268A CN201310329826A CN103396827A CN 103396827 A CN103396827 A CN 103396827A CN 2013103298268 A CN2013103298268 A CN 2013103298268A CN 201310329826 A CN201310329826 A CN 201310329826A CN 103396827 A CN103396827 A CN 103396827A
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- 229910017464 nitrogen compound Inorganic materials 0.000 title claims abstract description 65
- 150000002830 nitrogen compounds Chemical class 0.000 title claims abstract description 65
- 239000003245 coal Substances 0.000 title claims abstract description 52
- 238000000926 separation method Methods 0.000 title claims abstract description 31
- 239000003513 alkali Substances 0.000 title claims abstract description 18
- 239000000243 solution Substances 0.000 claims abstract description 46
- 239000003960 organic solvent Substances 0.000 claims abstract description 43
- 238000005554 pickling Methods 0.000 claims abstract description 30
- 238000000638 solvent extraction Methods 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000012074 organic phase Substances 0.000 claims abstract description 20
- 239000003929 acidic solution Substances 0.000 claims abstract description 19
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 239000008346 aqueous phase Substances 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 230000007935 neutral effect Effects 0.000 claims description 11
- 230000009514 concussion Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 6
- 239000012071 phase Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 238000002347 injection Methods 0.000 abstract description 3
- 239000007924 injection Substances 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- -1 nitrogenous compound Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention discloses a separation method for alkali nitrogen compounds in coal liquefaction oil. The separation method comprises the following steps of: acid pickling: mixing the coal liquefaction oil with an acidic solution, carrying out vibrating, standing and layering, and separating to obtain a water phase solution; and organic solvent extraction: regulating the pH value of the water phase solution to be 8-10, adding organic solvents after cooling, carrying out mixing, vibrating, standing and layering, and separating to obtain an organic phase solution rich in the alkali nitrogen compounds. By utilizing the separation method disclosed by the invention, the alkali nitrogen compounds in the coal liquefaction oil are processed by utilizing an acid pickling method and an organic solvent extraction method, the effects that the alkali nitrogen compounds in the coal liquefaction oil are good in separation selectivity and high in separation degree and are thoroughly extracted are achieved, and the obtained organic phase solution can be directly used for carrying out sample injection analysis on the alkali nitrogen compounds.
Description
Technical field
The present invention relates to coal liquefaction coal chemical technology, especially relate to a kind of separation method of liquefied coal coil neutral and alkali nitrogen compound.
Background technology
Coal direct liquefaction is as a high effect cleaning coal technology that can partial rcsponse China's oil resource supply and demand contradiction, entered at present Commercial Demonstration operation stage.Contain a certain amount of nitrogenous compound in the thick product liquefied coal coil of employing direct coal liquefaction process production, wherein quite a few is basic nitrogen compound for this.And the further hydrofining of liquefied coal coil is while producing diesel oil fuel, and basic nitrogen compound is one of principal element that causes catalyst deactivation., for grasping catalyst deactivation mechanisms, need to do the structure analysis to the basic nitrogen compound component; Purify from liquefied coal coil and transform have a high added value contain nitrogen compound when further promoting the economy of gelatin liquefaction technology, also need the nitrogenous compound in liquefied coal coil is formed and does detailed analysis.
But, the liquefied coal coil component is except a certain amount of nitrogenous compound, also contain a large amount of hydrocarbons and sulfur-bearing, oxygenatedchemicals etc., for analyzing as far as possible accurately the basic nitrogen compound in liquefied coal coil, usually need to carry out pre-treatment to it, extraction concentrates out the basic nitrogen compound in liquefaction oil, and then extract is done detailed proximate analysis.Yet the separation method of liquefied coal coil neutral and alkali nitrogen compound of the prior art, exist basic nitrogen compound and separate not exclusively, and in extract, foreign matter content is many, causes the inaccurate problem of basic nitrogen compound proximate analysis result.
Summary of the invention
The invention provides a kind of separation method of liquefied coal coil neutral and alkali nitrogen compound, to solve liquefied coal coil neutral and alkali nitrogen compound, separate not exclusively, in extract, foreign matter content is many, causes the inaccurate problem of basic nitrogen compound proximate analysis result.
To achieve these goals, according to an aspect of the present invention, provide a kind of separation method of liquefied coal coil neutral and alkali nitrogen compound.This separation method comprises the following steps: acid pickling step: liquefied coal coil is mixed with acidic solution and shakes, and standing and demixing, separate and obtain aqueous phase solution; The organic solvent extraction step: the pH value of aqueous phase solution is transferred to 8～10, add organic solvent after cooling, mix and shake, standing and demixing, separate the organic phase solution that obtains being enriched with basic nitrogen compound.
Further, the acidic solution in acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%～36wt%; The mass ratio of liquefied coal coil and acidic solution is 2:1～10:1.
Further, the acidic solution in acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%; The mass ratio of liquefied coal coil and acidic solution is 2:1～6:1.
Further, in acid pickling step, mix and time of shaking is 10～30 minutes, the time of standing and demixing is 10～30 minutes.
Further, in the organic solvent extraction step by adding sodium hydroxide and/or potassium hydroxide that the pH value of aqueous phase solution is transferred to 8～10 in aqueous phase solution.
Further, the organic solvent that adds in the organic solvent extraction step and the volume ratio of aqueous phase solution are 1:2～1:1.
Further, organic solvent is methylene dichloride.
Further, in the organic solvent extraction step, mix and time of shaking is 10～30 minutes, the time of standing and demixing is 10～30 minutes.
Further, acid pickling step repeats 1～4 time, and the aqueous phase solution of collecting is merged, and then carries out the organic solvent extraction step; The organic solvent extraction step repeats 1～4 time, and the organic phase solution of collecting is merged, and obtains the organic phase solution of enriched alkaline nitrogen compound.
Apply the separation method of liquefied coal coil neutral and alkali nitrogen compound of the present invention, adopt pickling to add organic solvent extration, basic nitrogen compound in liquefied coal coil is processed, reached that liquefied coal coil neutral and alkali nitrogen compound separation selectivity is good, resolution is high, extract effect thoroughly, and the organic phase solution that obtains can be directly used in the analysis of basic nitrogen compound sample introduction.
Embodiment
Need to prove, in the situation that do not conflict, embodiment and the feature in embodiment in the application can make up mutually.Describe the present invention in detail below in conjunction with embodiment.
Said in the present invention " liquefied coal coil " refers to coal under high-temperature and high-pressure conditions, the liquid fuel and the hydro-upgrading product thereof that generate by catalytic hydrogenation.
A kind of typical embodiment according to the present invention, provide a kind of separation method of liquefied coal coil neutral and alkali nitrogen compound.This separation method comprises the following steps: acid pickling step: liquefied coal coil is mixed with acidic solution and shakes, and standing and demixing, separate and obtain aqueous phase solution; The organic solvent extraction step: the pH value of aqueous phase solution is transferred to 8～10, add organic solvent after cooling, mix and shake, standing and demixing, separate the organic phase solution that obtains being enriched with basic nitrogen compound.
Because basic nitrogen compound has weakly alkaline, can react with acid and transfer to from liquefied coal coil in acidic solution, and the hydrocarbons in liquefied coal coil can not react so adopt solution with acid, not separate that basic nitrogen compound selectivity in liquefied coal coil is good, resolution is high.
At standing and demixing and after separating and obtaining aqueous phase solution, by add excessive alkali in aqueous phase solution, the pH value is adjusted to 8.0～10.0, neutralize the acid in aqueous phase solution fully, again obtain weakly alkaline nitrogen compound; , because acid-base neutralisation can be emitted certain heat, after water is cooled to room temperature, then add organic solvent to extract; Solubleness due to basic nitrogen compound in organic solvent is larger, so through extraction, the basic nitrogen compound of the overwhelming majority can be transferred in organic phase solution, standing and demixing, isolate organic phase solution, can obtain being enriched with the organic phase solution of basic nitrogen compound.But the basic nitrogen compound direct injection that is dissolved in organic solvent that obtains is like this carried out subsequent analysis, and owing to having eliminated the impurity composition interference, the accuracy of analysis is high.
In acid pickling step, as long as the acidic solution that uses can react with basic nitrogen compound, basic nitrogen compound in the gelatin liquefaction oil phase is transferred to aqueous phase get final product, preferably, the acidic solution in acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%～36wt%; The mass ratio of liquefied coal coil and acidic solution is 2:1～10:1; Further preferably, the acidic solution in acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%; The mass ratio of liquefied coal coil and acidic solution is 2:1～6:1, uses the acidic solution of this concentration range and mass ratio, can isolate fully up hill and dale the basic nitrogen compound in liquefied coal coil.
A kind of typical embodiment according to the present invention, in acid pickling step, mix and time of shaking is 10～30 minutes, and the time of standing and demixing is 10～30 minutes.The design of such operating time both can be so that water have fully contacted and had reacted with the gelatin liquefaction oil phase, thereby effectively isolated basic nitrogen compound, can reach higher working efficiency again.
In the organic solvent extraction step, aqueous phase solution pH value is adjusted to 8.0～10.0, namely neutralize the acid in aqueous phase solution, again obtain weakly alkaline nitrogen compound, preferably, in the organic solvent extraction step, by adding sodium hydroxide and/or potassium hydroxide that the pH value of aqueous phase solution is transferred to 8～10 in aqueous phase solution, sodium hydroxide and/or potassium hydroxide raw material are easy to get, and can not introduce the impurity that affects the following component analysis.
As long as the organic solvent that adds in the organic solvent extraction step and the volume ratio of aqueous phase solution can make the solubleness of basic nitrogen compound in this organic solvent obviously greater than the solubleness at aqueous phase, preferably, the organic solvent that adds in the organic solvent extraction step and the volume ratio of aqueous phase solution are 1:2～1:1.Preferably, this organic solvent is methylene dichloride, methylene dichloride can dissolve well aqueous phase basic nitrogen compound and with water layering well because density is greater than water, so reduced loss in the separatory process.Certainly, toluene also can, but toluene density is in upper strata less than water after layering, so in the separatory process, loss is large.
In the organic solvent extraction step, to mix and time of shaking is 10～30 minutes, the time of standing and demixing is 10～30 minutes, such operating time design both can, so that the organic solvent extraction process is fully carried out, can reach higher working efficiency again.
A kind of typical embodiment according to the present invention, acid pickling step and organic solvent extraction step all can be according to actual needs repeatedly, under the prerequisite that guarantees production efficiency and separating resulting, acid pickling step repeats 1～4 time, preferably, acid pickling step repeats 2 times, and the aqueous phase solution of collecting is merged, and then carries out the organic solvent extraction step; The organic solvent extraction step repeats 1～4 time, and the organic phase solution of collecting is merged, and obtains the organic phase solution of enriched alkaline nitrogen compound.
Separation method of the present invention, be applicable to concentration at basic nitrogen compound and be apply in the liquefied coal coil of 0.01wt%～2wt%, preferably, applies in the concentration of basic nitrogen compound is the liquefied coal coil of 0.1wt%～2wt%.Basic nitrogen lower than 0.01wt% content adopts this separation method,, because concentration is too low, extracts error larger, generally can not contain the basic nitrogen greater than 2wt% content in the liquefied coal coil product, and in principle higher than this content, this separation method is also out of question.
Usually, the subsequent component analysis of the phenolic compound that is dissolved in organic solvent being carried out comprises: gas chromatographic analysis, Infrared spectroscopy, mass spectroscopy etc.
Below in conjunction with the embodiment of the present invention, technical scheme of the present invention is described in detail, but following embodiment to understand the present invention, and can not limit the present invention, the multitude of different ways that the present invention can be defined by the claims and cover is implemented.
Embodiment 1
Make solvent with toluene, be mixed with massfraction and be the model compound (with the simulation liquefied coal coil) of 0.0296% pyridine, 0.0388% aniline, 0.0267% quinoline, 0.0123% acridine.
Get the 30g model compound and be placed in separating funnel, add the aqueous hydrochloric acid 5g concussion of 10% mass concentration to mix 10 minutes, separate lower floor's water after static 10 minutes, upper organic phase continues to separate lower floor's water with the aqueous hydrochloric acid concussion mixing of same amount after 10 minutes and static 10 minutes; The water of collecting adds the sodium hydroxide 12g of 10% mass concentration, the pH value of aqueous phase solution is transferred to 8～10, add methylene dichloride to extract (volume ratio of methylene dichloride and water is 1:2) after cooling, each extraction time is 20 minutes, collect the lower floor's organic phase that obtains, air inlet analysis of hplc after quadruplication.The rate of recovery of the basic nitrogen compound (pyridine, aniline, quinoline, acridine) that adds is respectively 90.70%, 96.79%, 94.32%, 95.09%.
, with air inlet analysis of hplc such as the remaining liquid after pickling and waters, the basic nitrogen compound component of interpolation do not detected.
Embodiment 2
Identical with embodiment 1, make solvent with toluene, be mixed with massfraction and be the model compound (with the simulation liquefied coal coil) of 0.0296% pyridine, 0.0388% aniline, 0.0267% quinoline, 0.0123% acridine.
Get the 30g model compound and be placed in separating funnel, add the aqueous hydrochloric acid 3g concussion of 36% mass concentration to mix 30 minutes, separate lower floor's water after static 30 minutes, upper organic phase continues to separate lower floor's water with the aqueous hydrochloric acid concussion mixing of same amount after 30 minutes and static 30 minutes; The water of collecting adds the sodium hydroxide 8g of 36% mass concentration, the pH value of aqueous phase solution is transferred to 8～10, add methylene dichloride to extract (volume ratio of methylene dichloride and water is 1:1) after cooling, each extraction time is 20 minutes, collect the lower floor's organic phase that obtains, air inlet analysis of hplc after quadruplication.The rate of recovery of the basic nitrogen compound (pyridine, aniline, quinoline, acridine) that adds is respectively 91.35%, 94.27%, 95.38%, 94.19%.
, with air inlet analysis of hplc such as the remaining liquid after pickling and waters, the basic nitrogen compound component of interpolation do not detected.
Embodiment 3
, with embodiment 1,, take unazotized gelatin liquefaction petroleum naphtha after hydro-upgrading as solvent, be mixed with massfraction and be the model compound of 0.0443% pyridine, 0.0482% aniline, 0.0502% quinoline, 0.0168% acridine.
Getting 30g adds target upgrading petroleum naphtha and is placed in separating funnel, add the aqueous sulfuric acid 5g concussion of 10% mass concentration to mix 10 minutes, separate lower floor's water after static 10 minutes, the water of collecting adds the potassium hydroxide 12g of 10% mass concentration, the pH value of aqueous phase solution is transferred to 8～10, add the methylene dichloride of 10 milliliters to extract after cooling, extraction time is 20 minutes, lower floor's organic phase that collection obtains, the air inlet analysis of hplc.
Be respectively 85.41%, 96.71%, 97.98%, 99.08% by the rate of recovery that obtains basic nitrogen compound (pyridine, aniline, quinoline, acridine) after pickling+extraction.
, with air inlet analysis of hplc such as the remaining liquid after pickling and waters, the basic nitrogen compound component of interpolation do not detected.
Embodiment 4
Separating step is with embodiment 1, after certain gelatin liquefaction full distillate oil that will contain a certain amount of basic nitrogen compound carries out pickling+extraction and extracts wherein basic nitrogen compound, does chromatogram/GC-MS analysis, 63 kinds of basic nitrogen compounds detected altogether; Remaining liquid after pickling and water etc. are carried out gas chromatographic analysis, basic nitrogen compound substantially do not detected.
by embodiment 1-4 as seen, the present invention has these characteristics of weakly alkaline according to basic nitrogen compound, adopt pickling to add organic solvent extration, liquefied coal coil is processed, the overall yield of basic nitrogen compound separation and Extraction reaches more than 94%, by mark-on reclaim to calculate (quality that the quality of the basic nitrogen that obtains after extraction mark-on liquefied coal coil deducts in liquefied coal coil the basic nitrogen that itself extracts be namely extract add target basic nitrogen quality, with itself add target basic nitrogen quality and do than the recovery of standard addition that is namely this basic nitrogen) and residue aqueous phase after the residue model compound organic solution phase after pickling or gelatin liquefaction oil phase and extraction the not separated basic nitrogen compound that extracts all do not detected.This shows, the present invention adopts pickling+organic solvent extraction to carry out the separation of liquefied coal coil neutral and alkali nitrogen compound, can effectively extract with separate liquefied coal coil in basic nitrogen compound, thorough to basic nitrogen compound, selectivity good, and separation efficiency is high, cost is low, but the sample direct injection analysis after processing.
The foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, for a person skilled in the art, the present invention can have various modifications and variations.Within the spirit and principles in the present invention all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (9)
1. the separation method of a liquefied coal coil neutral and alkali nitrogen compound, is characterized in that, comprises the following steps:
Acid pickling step: described liquefied coal coil is mixed with acidic solution and shakes, and standing and demixing, separate and obtain aqueous phase solution;
The organic solvent extraction step: the pH value of described aqueous phase solution is transferred to 8～10, add organic solvent after cooling, mix and shake, standing and demixing, separate the organic phase solution that obtains being enriched with described basic nitrogen compound.
2. separation method according to claim 1, is characterized in that, the described acidic solution in described acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%～36wt%; The mass ratio of described liquefied coal coil and described acidic solution is 2:1～10:1.
3. separation method according to claim 2, is characterized in that, the described acidic solution in described acid pickling step is that mass concentration is sulfuric acid or the hydrochloric acid of 10wt%; The mass ratio of described liquefied coal coil and described acidic solution is 2:1～6:1.
4. separation method according to claim 1, is characterized in that, in described acid pickling step, the time of described mixing and concussion is 10～30 minutes, and the time of described standing and demixing is 10～30 minutes.
5. separation method according to claim 1, is characterized in that, in described organic solvent extraction step by adding sodium hydroxide and/or potassium hydroxide that the pH value of described aqueous phase solution is transferred to 8～10 in described aqueous phase solution.
6. separation method according to claim 1, is characterized in that, the described organic solvent that adds in described organic solvent extraction step and the volume ratio of described aqueous phase solution are 1:2～1:1.
7. separation method according to claim 6, is characterized in that, described organic solvent is methylene dichloride.
8. separation method according to claim 1, is characterized in that, in described organic solvent extraction step, the time of described mixing and concussion is 10～30 minutes, and the time of described standing and demixing is 10～30 minutes.
9. the described separation method of any one according to claim 1 to 8, is characterized in that,
Described acid pickling step repeats 1～4 time, and the described aqueous phase solution of collecting is merged, and then carries out described organic solvent extraction step;
Described organic solvent extraction step repeats 1～4 time, and the described organic phase solution of collecting is merged, and obtains the organic phase solution of the described basic nitrogen compound of enrichment.
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| CN103923696A (en) * | 2014-04-29 | 2014-07-16 | 神华集团有限责任公司 | Separation method for aromatic hydrocarbon products and aromatic hydrocarbon substances in coal liquefaction oil |
| CN103923696B (en) * | 2014-04-29 | 2016-07-13 | 神华集团有限责任公司 | The separation method of aromatic hydrocarbon substance in aromatic hydrocarbon product and liquefied coal coil |
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| CN106324158B (en) * | 2015-06-17 | 2018-11-16 | 中国石油天然气股份有限公司 | Method for solid phase extraction of nitrogen-containing compounds in diesel oil |
| CN104927907A (en) * | 2015-07-01 | 2015-09-23 | 华东理工大学 | Alkylation product desulphurization and deacidifying method and device |
| CN106590734A (en) * | 2016-12-09 | 2017-04-26 | 辽宁石油化工大学 | Enrichment and separation method for basic nitrides in shale diesel oil |
| CN106590734B (en) * | 2016-12-09 | 2018-05-04 | 辽宁石油化工大学 | A kind of method of shale diesel oil neutral and alkali nitride concentration and separation |
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