CN106635144B - A kind of method of phenolic compound concentration and separation in shale oil - Google Patents
A kind of method of phenolic compound concentration and separation in shale oil Download PDFInfo
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- CN106635144B CN106635144B CN201611035607.9A CN201611035607A CN106635144B CN 106635144 B CN106635144 B CN 106635144B CN 201611035607 A CN201611035607 A CN 201611035607A CN 106635144 B CN106635144 B CN 106635144B
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- phenolic compound
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- shale oil
- compound concentration
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1033—Oil well production fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of method of phenolic compound in concentration and separation shale oil, the core of this method is the separation method being combined using solvent refining and column chromatography.Extractant used is mixed into carry out solvent refining in proportion with the full cut of shale oil, the tapped oil of preliminary concentration phenolic compound is obtained after refined, the raw material that the cut of tapped oil≤280 DEG C is enriched with as phenolic compound depth is cut, then phenolic compound is obtained through the further concentrating and separating of column chromatography, desolventizing, vacuum drying.
Description
Technical field
The application belongs to shale oil processing technique field, and in particular to phenolic compound concentration and separation in a kind of shale oil
Method.
Background technology
Shale oil is the potential energy source of storage capacity very abundant in the world, its total storage capacity is considerably beyond oil.With day
Right oil is compared, and the non-hydrocarbon compounds such as substantial amounts of unsaturated hydrocarbons and N, S, O are contained in shale oil.In China, shale oil is largely made
Extensive style burning is carried out for fuel, produces substantial amounts of NO in combustionxAnd SO2, using energy source while causing environmental pollution
It is worth low.Itself it is highly useful change although non-hydrocarbon compound is the noxious material that remove or convert in shale oil
Work raw material.Wherein, phenolic compound is widely used in synthetic fibers, medicine, pesticide, plasticizer, preservative, engineering plastics, dye
Expect the fields such as intermediate.In recent years, the research that phenolic compound is extracted from coal tar, shale oil and oil product has caused
The extensive concern of domestic and international researcher.
At present, the extracting method of phenolic compound mainly has solvent refining, Separation by Complexation, soda acid elution, column in shale oil
Combination of chromatography, thin-layer chromatography and the above method etc..
Solvent refining is a kind of new isolation technics developed rapidly in 20th century, i.e. solvent extraction, the method for use
For the similar principle that mixes, according to solubility of the phenolic compound to be separated in oil product between the solvent of use difference
Selectively it is isolated, separating effect is preferable.
What Separation by Complexation method was applied is Lewis acid-base theories, complexing agent and phenolic compound in Lewis acid and Lewis alkali
Complexing power under, form complex compound and oil phase and be layered, so that phenolic compound be separated from oil product.CN
103937522A discloses the separation method of phenolic compound and nitrogenous compound in coal tar, and the Separation by Complexation agent of use contains gold
Belong to chloride, phosphate and halogeno salt, wherein metal chloride and halogeno salt mass ratio are 0.05~0.2, phosphate and halo
The mass ratio of salt is 0.04~0.15, and the mass ratio of Separation by Complexation agent and coal tar is 0.05~0.7.It the method achieve coal tar
Optionally quick separating, separating effect are preferable for phenolic compound and nitrogenous compound in oil.But complexing used by this method
Release agent cost is higher, prepares more complicated.
Soda acid elution is that have faintly acid using phenolic compound, is reacted using the principle and highly basic of acid-base neutralization
Afterwards, the sodium phenolate solution of formation is transferred to water phase insoluble in oil phase, reuses carbon dioxide or sulfuric acid solution acidifying, restores
Phenols.This method high selectivity, it is easy to operate, but soda acid need to be largely used, height, while quantity of wastewater effluent are required equipment anticorrosion
Greatly, environmental pollution is larger.
Column chromatography belongs to liquid-solid adsorption chromatography, it is a kind of technology of the principle based on absorption-dissolving.Using two-phase it
Between the various molecular separating force such as Van der Waals force and hydrogen bond effect, when mixture solution is added in stationary phase, each group in mixture
Divide and the surface of solids is attracted to different action intensities.Since adsorbent is different to the adsorption capacity of each material, adsorb strong
Component distributed in mobile phase it is few, and adsorb weak component distributed in mobile phase it is more so that each component in mixture obtains
Efficiently separate.
Thin-layer chromatography belongs to solid-liquid adsorption chromatography, is a kind of micro method for separating and analyzing, has that equipment is simple, speed
It hurry up, good separating effect, high sensitivity and the advantages that corrosivity color developing agent can be used, but be only applicable to the separation of low-volume samples.
The content of the invention
The present invention is directed to above-mentioned problems of the prior art, there is provided phenolic compound enrichment point in a kind of shale oil
From method.The separation method that this method is combined using solvent refining and column chromatography, it is easy to operate feasible, can be by phenols chemical combination
Thing is separated with hydro carbons, nitrogenous compound, the phenolic compound in shale oil is obtained effective concentration and separation.
Technical scheme comprises the following steps：
Extractant is mixed in proportion with the full cut of shale oil and is stirred reaction, rear oil product divides standing sedimentation for a period of time
For two layers, the extractant of the upper and lower can be recycled by being evaporated under reduced pressure, and be recycled；Lower floor obtains preliminary richness after taking off extractant
Collect the tapped oil of phenolic compound；The cut for cutting tapped oil≤280 DEG C removes alkaline chemical combination through column chromatography concentrating and separating, acid elution
Thing, alkali density phenolic compound, acid neutralize phenates, solvent back suction carries phenolic compound, desolventizing, is dried in vacuo to obtain phenols chemical combination
Thing.
The extractant for n,N-Dimethylformamide, furfural, dimethyl sulfoxide (DMSO), 1-methyl-2-pyrrolidinone one kind or
It is several.
The stirring reaction temperature is 50-80 DEG C.
The sedimentation time is 10-50min.
The column chromatography solid absorbent is silica gel.
The column chromatography mobile phase is petroleum ether, benzene/methanol mixed solution.
The volume ratio of benzene/methanol mixed solution is 1-2 in the column chromatography mobile phase：1.
The acid is hydrochloric acid, concentration 3mol/L-6mol/L.
The alkali is sodium hydroxide or potassium hydroxide.
The solvent is ether.
Advantages of the present invention effect is as follows：
The separation method that the present invention is combined using solvent refining and column chromatography, it is easy to operate feasible, can be by phenols chemical combination
Thing is separated with hydro carbons, nitrogenous compound, is conducive to the concentration and separation of phenolic compound.Meanwhile it is molten both to avoid a large amount of acid, buck
The use of liquid, extractant recoverable, greatly reduces production cost, and the phenolic compound in shale oil is obtained effectively
Concentration and separation.
Brief description of the drawings
Fig. 1 is the result that the final product that gas chromatograph-mass spectrometer (GC-MS) (GC-MS) is enriched with embodiment 3 is characterized
Curve map.
Embodiment
Embodiment 1
99ml furfurals are taken to mix (molar ratio 0.3 with the full cut of 330ml shale oil:1), heating water bath stirs, and setting adds
Hot temperature is 50 DEG C, after stirring, pours into separatory funnel and treats that sample is layered, after standing 10min, the oil product of lower floor is carried out
Distillation, obtains tapped oil and furfural, furfural recycles.Tapped oil is subjected to distillation cutting by every 20 DEG C of fraction sections, will
It is divided into≤260 DEG C, 260 DEG C~280 DEG C, 280 DEG C~300 DEG C, 300 DEG C~320 DEG C, 320 DEG C~340 DEG C, 340 DEG C~360
℃、>360 DEG C of seven fraction sections, carry out phenol content analysis.Take≤280 DEG C of cut to carry out pillar layer separation, weigh silica gel 50g,
Successively with petroleum ether, benzene/methanol mixed solution (volume ratio 1：1) chromatographic elution is carried out to chromatographic column.Obtained benzene/methanol punching
Go out liquid and benzene layer solution is isolated after water extracts 3 times, then organic layer is obtained with the HCl extracting benzene layer solution of 3mol/L, use quality
The NaOH solution that fraction is 10%, which extracts, obtains NaOH inorganic layers after organic layer 3 times, then with the HCl of 6mol/L to NaOH inorganic layers
It is acidified, adds ether afterwards, phenolic compound is extracted from water phase, solvent is steamed, obtains flaxen phenols
Compound.
Embodiment 2
By extractant dimethyl sulfoxide (DMSO) and the full cut of shale oil in molar ratio 0.5:The mixing of 1 ratio is stirred reaction, stirs
It is 50 DEG C to mix reaction temperature, and oil product is divided into two layers after standing sedimentation 20min, and the extractant of the upper and lower can pass through vacuum distillation
Recycling, recycles；Lower floor obtains the tapped oil of preliminary concentration phenolic compound after taking off extractant；Cut tapped oil≤280 DEG C
Cut through column chromatography concentrating and separating, acid elution remove alkali compounds, alkali density phenolic compound, that acid neutralizes phenates, solvent is anti-
Extracting phenolic compound, desolventizing, be dried in vacuo to obtain phenolic compound.The column chromatography solid absorbent is silica gel；It is described
Column chromatography mobile phase for petroleum ether, benzene/methanol mixed solution；The volume ratio of benzene/methanol mixed solution is 1：1；Other steps
With embodiment 1.
Embodiment 3
By extractant furfural and the full cut of shale oil in molar ratio 1:The mixing of 1 ratio is stirred reaction, stirring reaction temperature
Spend for 60 DEG C, oil product is divided into two layers after standing sedimentation 30min, and the extractant of the upper and lower can be recycled by being evaporated under reduced pressure, and be followed
Ring utilizes；Lower floor obtains the tapped oil of preliminary concentration phenolic compound after taking off extractant；Cut the cut warp of tapped oil≤280 DEG C
Column chromatography concentrating and separating, acid elution go alkali compounds, alkali density phenolic compound, acid neutralization phenates, solvent back suction to carry phenols
Compound, desolventizing, be dried in vacuo to obtain phenolic compound.The column chromatography solid absorbent is silica gel；The column chromatography
Mobile phase is petroleum ether, benzene/methanol mixed solution；The volume ratio of benzene/methanol mixed solution is 1：1；Other same embodiments of step
1。
Embodiment 4
By extractant 1-methyl-2-pyrrolidinone and the full cut of shale oil in molar ratio 1:The mixing of 1 ratio is stirred reaction,
It is 70 DEG C to stir reaction temperature, and oil product is divided into two layers after standing sedimentation 50min, and the extractant of the upper and lower can be steamed by depressurizing
Recycling is evaporated, is recycled；Lower floor obtains the tapped oil of preliminary concentration phenolic compound after taking off extractant；Cut tapped oil≤280
DEG C cut through column chromatography concentrating and separating, acid elution go alkali compounds, alkali density phenolic compound, acid neutralize phenates, solvent
Back suction carries phenolic compound, desolventizing, is dried in vacuo to obtain phenolic compound.The column chromatography solid absorbent is silica gel；Institute
The column chromatography mobile phase stated is petroleum ether, benzene/methanol mixed solution；The volume ratio of benzene/methanol mixed solution is 1.2：1；It is other
Step is the same as embodiment 1.
Embodiment 5
By extractant n,N-Dimethylformamide and the full cut of shale oil in molar ratio 2:The mixing of 1 ratio is stirred anti-
Should, stirring reaction temperature is 80 DEG C, and oil product is divided into two layers after standing sedimentation 50min, and the extractant of the upper and lower can be by subtracting
Pressure is distilled to recover, and is recycled；Lower floor obtains the tapped oil of preliminary concentration phenolic compound after taking off extractant；Cut tapped oil≤
280 DEG C of cut goes alkali compounds, alkali density phenolic compound, acid to neutralize phenates, molten through column chromatography concentrating and separating, acid elution
Agent back suction carries phenolic compound, desolventizing, is dried in vacuo to obtain phenolic compound.The column chromatography solid absorbent is silica gel；
The column chromatography mobile phase is petroleum ether, benzene/methanol mixed solution；The volume ratio of benzene/methanol mixed solution is 2：1；It is other
Step is the same as embodiment 1.
Result of implementation
The final product being enriched with by gas chromatograph-mass spectrometer (GC-MS) (GC-MS) to embodiment 3 characterizes, the result is shown in
Fig. 1 and table 1.The gradient enrichment of phenolic compound the results are shown in Table 2 in embodiment 3.
The GC-MS results of 1 final product of table
The gradient enrichment result of phenolic compound in 2 shale oil of table
The method that phenolic compound in shale oil can be combined by solvent refining and column chromatography is effectively enriched with
With separating, phenol content is concentrated to the 9.40% of tapped oil by the 4.31% of raw material shale oil, then is enriched to tapped oil≤280 DEG C and evaporates
35% divided, finally by its further separating and concentrating to 79.5%.The compound identified in the product of concentration and separation is main
For C1~C3 phenol compounds.
Claims (10)
1. a kind of method of phenolic compound concentration and separation in shale oil, its feature：This method comprises the following steps：By extractant
Be mixed in a certain ratio with the full cut of shale oil, be stirred reaction at a certain temperature, standing sedimentation for a period of time after oil product
It is divided into two layers, the extractant of the upper and lower can be recycled by being evaporated under reduced pressure, and be recycled, and lower floor obtains just after taking off extractant
The tapped oil of step enrichment phenolic compound, the cut for cutting tapped oil≤280 DEG C go alkalescence through column chromatography concentrating and separating, acid elution
Compound, alkali density phenolic compound, acid neutralize phenates, solvent back suction carries phenolic compound, desolventizing, is dried in vacuo to obtain phenols
Compound.
2. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：Extraction
The mass ratio of agent and shale oil is 0.3-2：1.
3. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1 or 2, it is characterised in that：
The extractant is n,N-Dimethylformamide, furfural, dimethyl sulfoxide (DMSO), the one or more of 1-methyl-2-pyrrolidinone.
4. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：It is described
Stirring reaction temperature be 50-80 DEG C.
5. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：Sedimentation
Time is 10-50min.
6. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：Column color
Spectrum solid absorbent is silica gel, and mobile phase is both petroleum ether and benzene/methanol mixed solution.
7. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 6, it is characterised in that：Column color
The volume ratio for composing benzene/methanol mixed solution in mobile phase is 1-2：1.
8. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：It is described
Acid be hydrochloric acid, concentration 3mol/L-6mol/L.
9. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：It is described
Alkali use sodium hydroxide or potassium hydroxide.
10. the method for phenolic compound concentration and separation in a kind of shale oil according to claim 1, it is characterised in that：Institute
The solvent stated is ether.
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| CN112755586A (en) * | 2020-12-29 | 2021-05-07 | 西安元创化工科技股份有限公司 | Method for extracting phenolic compounds from low-temperature coal tar |
| CN112919720A (en) * | 2021-04-14 | 2021-06-08 | 陕西煤业化工集团神木天元化工有限公司 | Method for extracting dihydric phenol from wastewater |
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