CN103896739B - Method for extracting phenol compounds from direct coal liquefied oil through extractive distillation - Google Patents
Method for extracting phenol compounds from direct coal liquefied oil through extractive distillation Download PDFInfo
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- CN103896739B CN103896739B CN201410162519.XA CN201410162519A CN103896739B CN 103896739 B CN103896739 B CN 103896739B CN 201410162519 A CN201410162519 A CN 201410162519A CN 103896739 B CN103896739 B CN 103896739B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C37/80—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
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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
- C10G7/00—Distillation of hydrocarbon oils
- C10G7/08—Azeotropic or extractive distillation
Abstract
The invention relates to a method for extracting phenol compounds from direct coal liquefied oil through extractive distillation. An extractive distillation solvent (hereinafter referred to as solvent) adopted in the method is glyceryl triacetate and/or sulfolane, or a mixed solvent formed by mixing glyceryl triacetate and/or sulfolane and one or more selected from glycerol, triethanolamine, triethylene glycol, tetraethylene glycol, dimethyl sulfoxide and diethanol amine according to any proportion. The method is used for extracting phenol compounds from direct coal liquefied oil in an extraction distillation tower by using the solvent, then, a solvent flow rich in the phenol compounds enters a recovery tower and is separated, the phenol compounds discharged from the top of the recovery tower are recovered after being cooled to obtain phenol products, and the solvent is recycled after being discharged from the bottom of the recovery tower. The method has the characteristics of high product purity, low system energy consumption, no wastewater generation, no acid and alkaline waste and no corrosion to equipment.
Description
Technical field
The present invention relates to coal chemical technology, be specifically related to a kind of method being extracted phenolic compound by extracting rectifying means from coal direct liquefaction oil.Belong to the working method of DCL/Direct coal liquefaction industry in Coal Chemical Industry.
Background technology
Phenolic compound is a series of general names with the arene derivatives of one or more hydroxyl.People find in the course of processing of liquefied coal coil product, phenolic compound has special constructional feature due to it, the circulating solvent performance in the stability of oil product, coal liquefaction craft can be affected, therefore the aldehydes matter isolated in liquefied coal coil will contribute to storage, the transport of oil product and Optimization Technology structure.Phenolic compound has slightly acidic, is the chief component of oxygenatedchemicals in liquefied coal coil.In following process process, high phenol content will significantly increase hydrogen consumption, and hydrogen is a kind of valuable raw material in compound probability, and this can promote production cost undoubtedly.Phenolic compound is a class high value added product, and range of application is very wide, relates to medicine, agricultural chemicals, organic synthesis etc., with the life of people and industrial production closely related.From oil product, separating phenols compounds will increase the added value of coal converted products greatly, has very high economic benefit.Along with industrial expansion, the consumption of fossil energy brings huge phenolic wastewater discharge, is one of main in the world pollutent, serious threat to the life of people, health and safety.Limit by existing processing condition, a large amount of phenolic wastewater produced in the oil product course of processing need process, add production cost, also pollute the environment, differ greatly with the requirement of friendly process, be badly in need of being improved it.If the phenolic compound of the overwhelming majority can be gone out from source separation, both can not have a negative impact to following process, again can simplification of flowsheet, a large amount of discharge reducing sewage, significant.As from the foregoing, no matter be control from production cost, process simplification, the angle that benefit is optimized, or from environmental angle, from coal direct liquefaction oil, extract phenolic compound significant.
In liquefied coal coil, phenols composition is very complicated, and kind is up to nearly hundred kinds.In the product liquid of different coal liquefaction craft or same liquefaction process Coal rank, the content of phenolic compound is larger with composition difference, but lower boiling phenol, alkylphenol, naphthols and alkyl naphthol are its main components, this just provides possibility for the extracting of phenolic compound in liquefaction oil.
People had done a lot of research to the separation of phenols, and concrete method mainly contains chemical transformation, supercritical extraction, pressure crystallizing method and solvent extraction process.Chemical method utilizes the phenolic compound in chemical reagent and oil to react, the method that they separate from coal tar.Conventional chemical reagent has sodium hydroxide solution, sodium carbonate solution and sodium hydrosulfide.Supercritical extraction utilizes the special property of some supercutical fluids to carry out the method be separated, generally conventional supercritical CO
2.But supercritical fluid extraction not yet carries out systematic study, also lack and be applied to the validation verification that concrete oil product puies forward phenol effect.
Pressure crystallization uses mechanical energy to carry out lock out operation, squeezing and solid-liquid separation carried out, so single job just can obtain the product of higher degree when partial crystallization simultaneously.All there are some problems in the above-mentioned method mentioned, chemical method is because its phenols purity is high, neutral oil is carried secretly less and is widely used, but the use of a large amount of bronsted lowry acids and bases bronsted lowry not only has stronger corrodibility to equipment, also cause environmental pollution, also there is considerable influence to dephenolize oil following process catalyst activity, creating a large amount of reluctant CaCO when reclaiming NaOH simultaneously
3.
Solvent extraction process adopts some solvent to have higher dissolving power to phenols, and the performance then very low to oils solubleness, separates phenols from oil.Common solvent has superheated water, salts solution and alcohol solution.A kind of method extracting phenolic compound from liquefied coal coil or coal tar is disclosed in Chinese patent application 201110102049.4, described method comprises: all or part of carbolic oil fraction section 1) liquefied coal coil or coal tar distillation process being cut < 260 DEG C, 2) adopt alcohol solution or aqueous alkanolamine as extraction agent, mix with 1: 1 ~ 10: 1 mass ratio with above-mentioned carbolic oil fraction section, fully stir at 20 ~ 130 DEG C, layering after mixing; 3) be separated and collect the extraction oxidant layer containing phenolic compound; 4) multistage back extraction extraction is carried out to the phenolic compound in extraction oxidant layer, obtain reverse-extraction agent-phenol solution and extraction agent, extraction agent recycle; 5) by the above-mentioned reverse-extraction agent-phenol solution of rectifying separation, reclaim reverse-extraction agent, recycle, and separation obtains phenolic compound; 6) water vapor carries the neutral oil carried secretly in removing phenolic compound, finally obtains crude phenols product.The maximum drawback of the method is that the phenol products extracted contains more neutral oil, and neutral oil is carried secretly and seriously caused effect poor, can produce a large amount of phenolic wastewater further with water vapor extracting neutral oil.Therefore, need to find a kind of suitable dephenolize solvent and dephenolizing process both could avoid the use of acid, alkali and water, improve again extraction yield and the purity of phenols as much as possible.
Summary of the invention
The object of the present invention is to provide one not use soda acid, do not produce waste water, energy consumption is low, purity and the rate of recovery high, the coal direct liquefaction oil not affecting following process carries phenol method, both the environmental requirement of increasingly stringent had been met, efficiently can carry phenol again, the solvent that described method adopts can significantly improve phenolic compound and oil product relative volatility, be easy to reclaim, chemical heat stablizes.
The invention provides a kind of method being extracted phenolic compound in coal direct liquefaction oil by extracting rectifying means, said method comprising the steps of:
A. cut the rich phenol fraction section of coal direct liquefaction oil, and by rich phenol fraction section by rectifying tower again cutting be the first narrower rich phenol distillate and the second rich phenol distillate;
B. in extractive distillation column, adopt solvent to carry out extracting rectifying to described first rich phenol distillate, obtain rich phenol solvent streams and dephenolize oil; Described solvent comprises vanay and/or tetramethylene sulfone;
C. respectively separated from solvent is carried out to the rich phenol solvent streams that step B obtains by recovery tower, obtain phenolic compound and circulating solvent;
D. by water cooler, the phenolic compound that step C obtains is cooled, obtain phenol products;
E. repeating step B-D is to described second rich phenol distillate dephenolize, obtains the second dephenolize oil and the second phenol products.
Further, described solvent also comprises one or more solvents in glycerol, trolamine, triglycol, in Tetraglycol 99, dimethyl sulfoxide (DMSO) and diethanolamine, and one or more described solvents mix with arbitrary proportion with vanay and/or tetramethylene sulfone.
Wherein different with the solvent of the second rich phenol distillate for extracting rectifying first rich phenol distillate.And described solvent load is 0.1-10 times of described first rich phenol distillate or the second rich phenol distillate inlet amount, preferred 0.5-8 doubly.
Described coal direct liquefaction oil cuts rich phenol fraction section by distillation or rectifying, and described rich phenol fraction section is 120-260 DEG C, and be preferably the fraction section of 170-230 DEG C, cutting is the cutting temperature point of the first rich phenol distillate and the second rich phenol distillate is 200 DEG C.
Wherein the treating processes of step B and C is: the first rich phenol distillate or the second rich phenol distillate are introduced at the bottom of the tower of extractive distillation column, described solvent is introduced from tower top, after extracting rectifying, the dephenolize oil obtained is discharged from the tower top of extractive distillation column, rich phenol solvent streams escapes and enter recovery tower at the bottom of the tower of extractive distillation column, the phenolic compound obtained after separated from solvent is discharged from the tower top of recovery tower, and recycling design is discharged Posterior circle and utilized at the bottom of the tower of recovery tower.
Wherein, the second dephenolize oil that the dephenolize oil obtained by step B and step e obtain obtains product dephenolize oil respectively by merging after water cooler cooling; The second phenol products merging that the phenol products obtained by step D and step e obtain obtains phenol products.
The operational condition of extractive distillation column and solvent recovery tower can adopt the condition usually adopted in prior art, in the present invention, and can preferred following operational condition:
The number of theoretical plate of described extractive distillation column is 5-20, and trim the top of column is than being 1-5, and tower top temperature is 180-220 DEG C, and tower top pressure is 0.08-0.15MPa, and column bottom temperature is 200-280 DEG C, and tower bottom pressure is 0.09-0.16MPa.
The theoretical plate number of described recovery tower is 5-20, and trim the top of column is than being 2-6, and tower top temperature is 200-230 DEG C, and tower top pressure is 0.08-0.15MPa, and column bottom temperature is 230-360 DEG C, and tower bottom pressure is 0.09-0.14MPa.
The invention has the advantages that:
1, what the present invention adopted is that the method for extracting rectifying extracts phenolic compound from coal direct liquefaction oil, solvent for use formula significantly can improve the relative volatility of phenolic compound and oil product, add and carbolic oil fraction section is cut to narrower two sections, effectively can reduce carrying secretly of neutral oil in extracting rectifying process, the phenolic compound of higher degree (massfraction >97%) and higher recovery (rate of recovery >98%) can be obtained with less stage number (stage number <20), reach the object of phenolic compound and oily high efficiency separation, do not need the neutral oil again processed with water vapor in removing phenolic compound.
2, the present invention does not use water vapor and acid, alkaline solution, without the need to the recovery of water, greatly can reduce consuming of system, can not produce reluctant waste water yet.
3, no waste discharge in the whole process of the present invention, adopt method separation of extractive distillation phenolic compound of the present invention and oil, the product purity obtained is high, system energy consumption is low, do not produce waste water, do not waste soda acid, not etching apparatus, and facility investment can reduce greatly, has a extensive future.
Accompanying drawing explanation
Fig. 1: the schematic flow sheet by extracting rectifying means extracting phenolic compound from coal direct liquefaction oil of the present invention.
T1 extractive distillation column, T2 recovery tower, C1 first condenser, C2 second condenser,
E1 first reboiler, E2 second reboiler,
The rich phenol distillate of 1-the first or the second; 2-product dephenolize oil; 3-enters the rich phenol solvent streams of recovery tower;
4-phenol products; 5-circulating solvent.
Embodiment
According to method of the present invention, further illustrate the present invention below in conjunction with embodiment, but the present invention is not limited to this.
Raw material used in the embodiment of the present invention is the coal direct liquefaction oil of the 120-260 DEG C of fraction section provided by Beijing Coal-Chemical Branch of Coal-Science General Academy, cut the rich phenol fraction section of wherein 170-230 DEG C by distillation, then cut 170-200 DEG C (the first rich phenol distillate) and 200-230 DEG C (the second rich phenol distillate) wherein by rectifying tower.
As shown in Figure 1, first or second rich phenol distillate 1 enters the bottom of extractive distillation column T1, circulating solvent 5 enters extractive distillation column T1 by top, through separation of extractive distillation, tower top goes out dephenolize oil after the first water cooler C1 cools, a part passes back into the top of extractive distillation column, and another part is discharged as product dephenolize oil 2; The rich phenol solvent streams gone out from extractive distillation column T1 tower bottom flow is introduced into the middle part of recovery tower T2, through being separated, reclaiming tower top and distillating phenolic compound, after the second water cooler C2 cools, a part is back to the top of tower T2 as phenolic compound, another part is then discharged as product phenols 4; The circulating solvent 5 gone out from recovery tower T2 tower bottom flow flows into the top of extractive distillation column T1, recycles.
Embodiment 1:
In embodiment 1, the 170-200 DEG C first rich phenol distillate tetramethylene sulfone and triglycol mixed solvent (mass ratio 1:1) are as No. 1 solvent, and the second rich phenol distillate vanay of 200-230 DEG C and trolamine mixed solvent (mass ratio 2:1) are as No. 2 solvents.
The dephenolizing process condition of 170-200 DEG C of the first rich phenol distillate in table 1 embodiment 1
| Processing condition | Extractive distillation column T1 | Recovery tower T2 |
| Stage number | 15 | 10 |
| No. 1 rich phenol distillate (mass ratio) of solvent/the first | 1.2 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 183.5 | 213.2 |
| Column bottom temperature DEG C | 246.2 | 301.4 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.111 | 0.111 |
Each logistics property in 170-200 DEG C of the first rich phenol distillate dephenolize process in table 2 embodiment 1
The dephenolizing process condition of 200-230 DEG C of the second rich phenol distillate in table 3 embodiment 1
| Processing condition | Extractive distillation column T1 | Solvent recovery tower T2 |
| Stage number | 13 | 15 |
| No. 2 rich phenol distillates (mass ratio) of solvent/the second | 1.2 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 205.9 | 213.2 |
| Column bottom temperature DEG C | 268.1 | 349.8 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.110 | 0.111 |
Each logistics property in 200-230 DEG C of the second rich phenol distillate dephenolize process in table 4 embodiment 1
Embodiment 2:
In embodiment 2,170-200 DEG C of the first rich phenol distillate tetramethylene sulfone is as No. 1 solvent, and 200-230 DEG C of the second rich phenol distillate vanay is as No. 2 solvents.
The dephenolizing process condition of 170-200 DEG C of the first rich phenol distillate in table 5 embodiment 2
| Processing condition | Extractive distillation column T1 | Solvent recovery tower T2 |
| Stage number | 16 | 11 |
| No. 1 rich phenol distillate (mass ratio) of solvent/the first | 1.3 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 180.6 | 210.3 |
| Column bottom temperature DEG C | 245.1 | 302.3 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.111 | 0.111 |
Each logistics property in 170-200 DEG C of the first rich phenol distillate dephenolize process in table 6 embodiment 2
The dephenolizing process condition of 200-230 DEG C of the second rich phenol distillate in table 7 embodiment 2
| Processing condition | Extractive distillation column T1 | Solvent recovery tower T2 |
| Stage number | 15 | 16 |
| No. 2 rich phenol distillates (mass ratio) of solvent/the second | 1.2 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 203.8 | 211.1 |
| Column bottom temperature DEG C | 260.2 | 270.6 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.110 | 0.111 |
Each logistics property in 200-230 DEG C of the second rich phenol distillate dephenolize process in table 8 embodiment 2
Comparative example 3:
In comparative example 3,170-200 DEG C of the first rich phenol distillate glycerol is as No. 1 solvent, and 200-230 DEG C of the second rich phenol distillate diethanolamine is as No. 2 solvents.
The dephenolizing process condition of 170-200 DEG C of the first rich phenol distillate in table 9 comparative example 3
| Processing condition | Extractive distillation column T1 | Solvent recovery tower T2 |
| Stage number | 15 | 10 |
| No. 1 rich phenol distillate (mass ratio) of solvent/the first | 1.2 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 183.5 | 213.2 |
| Column bottom temperature DEG C | 246.2 | 301.4 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.111 | 0.111 |
Each logistics property in 170-200 DEG C of the first rich phenol distillate dephenolize process in table 10 comparative example 3
The dephenolizing process condition of 200-230 DEG C of the second rich phenol distillate in table 11 comparative example 3
| Processing condition | Extractive distillation column T1 | Recovery tower T2 |
| Stage number | 13 | 15 |
| No. 2 rich phenol distillates (mass ratio) of solvent/the second | 1.2 | - |
| Reflux ratio | 2 | 3 |
| Tower top temperature DEG C | 205.9 | 213.2 |
| Column bottom temperature DEG C | 268.1 | 349.8 |
| Tower top pressure MPa | 0.101 | 0.101 |
| Tower bottom pressure MPa | 0.110 | 0.111 |
Each logistics property in 200-230 DEG C of the second rich phenol distillate dephenolize process in table 12 comparative example 3
As can be seen from the data of table 1-table 12, after the rich phenol fraction section cut by coal direct liquefaction oil is cut into two sections again, 170-200 DEG C of the first rich phenol distillate is containing phenol 53%, containing phenol 40% in 200-230 DEG C of the second rich phenol distillate, two groups of solvents in test, are selected to carry out extracting rectifying to the first rich phenol distillate and the second rich phenol distillate respectively.Product recovery rate and purity are all more than 97%, and solvent recovering rate and purity are also all more than 99%, and in product, contained neutral oil content is lower than 1%.
And in comparative example 3, select glycerol and diethanolamine to carry out extracting rectifying to the first rich phenol distillate and the second rich phenol distillate respectively.Because the k value of glycerol is up to 1142mPas, the k value of diethanolamine is slightly low also up to 380 mPas, far above the k value of vanay (18.7 mPas) and tetramethylene sulfone (10.3 mPas), cause the dissolving power of glycerol and diethanolamine more weak, poor fluidity, reclaims difficulty, so product recovery rate and purity can only reach about 90%, solvent recovering rate and purity also only have about 94%, and in product, contained neutral oil content reaches 7-8%.Therefore, compared with comparative example 3, in visible the application, adopt the extracting rectifying effect comprising the solvent of vanay and/or tetramethylene sulfone better than the extracting rectifying effect being extraction agent with glycerol or diethanolamine.
Claims (9)
1. extracted a method for phenolic compound in coal direct liquefaction oil by extracting rectifying means, said method comprising the steps of:
A. cut the rich phenol fraction section of coal direct liquefaction oil, and by rich phenol fraction section by rectifying tower again cutting be the first narrower rich phenol distillate and the second rich phenol distillate; The rich phenol fraction section of wherein said coal direct liquefaction oil is the fraction section of 170-230 DEG C, and cutting is the cutting temperature point of the first rich phenol distillate and the second rich phenol distillate is 200 DEG C;
B. in extractive distillation column, adopt solvent to carry out extracting rectifying to described first rich phenol distillate, obtain rich phenol solvent streams and dephenolize oil; Described solvent comprises vanay and/or tetramethylene sulfone;
C. respectively separated from solvent is carried out to the rich phenol solvent streams that step B obtains by recovery tower, obtain phenolic compound and circulating solvent;
D. by water cooler, the phenolic compound that step C obtains is cooled, obtain phenol products;
E. repeating step B-D is to described second rich phenol distillate dephenolize, obtains the second dephenolize oil and the second phenol products.
2. the method for claim 1, described solvent also comprises one or more solvents in glycerol, trolamine, triglycol, Tetraglycol 99, dimethyl sulfoxide (DMSO) and diethanolamine, and one or more described solvents mix with arbitrary proportion with vanay and/or tetramethylene sulfone.
3. method as claimed in claim 1 or 2, wherein the treating processes of step B and C is: the first rich phenol distillate or the second rich phenol distillate are introduced at the bottom of the tower of extractive distillation column, described solvent is introduced from tower top, after extracting rectifying, the dephenolize oil obtained is discharged from the tower top of extractive distillation column, rich phenol solvent streams escapes and enter recovery tower at the bottom of the tower of extractive distillation column, the phenolic compound obtained after separated from solvent is discharged from the tower top of recovery tower, and recycling design is discharged Posterior circle and utilized at the bottom of the tower of recovery tower.
4. method as claimed in claim 1 or 2, wherein different with the solvent of the second rich phenol distillate for extracting rectifying first rich phenol distillate.
5. method as claimed in claim 1 or 2, the second dephenolize oil that the dephenolize obtained by step B oil and step e obtain obtains product dephenolize oil respectively by merging after water cooler cooling; The second phenol products merging that the phenol products obtained by step D and step e obtain obtains phenol products.
6. method as claimed in claim 1 or 2, is characterized in that: described solvent load is 0.1-10 times of described first rich phenol distillate or the second rich phenol distillate inlet amount.
7. method as claimed in claim 6, is characterized in that: described solvent load is 0.5-8 times of described first rich phenol distillate or the second rich phenol distillate inlet amount.
8. method as claimed in claim 1 or 2, is characterized in that: the number of theoretical plate of described extractive distillation column is 5-20, and trim the top of column is than being 1-5, tower top temperature is 180-220 DEG C, tower top pressure is 0.08-0.15MPa, and column bottom temperature is 200-280 DEG C, and tower bottom pressure is 0.09-0.16MPa.
9. method as claimed in claim 1 or 2, is characterized in that: the theoretical plate number of described recovery tower is 5-20, and trim the top of column is than being 2-6, tower top temperature is 200-230 DEG C, tower top pressure is 0.08-0.15MPa, and column bottom temperature is 230-360 DEG C, and tower bottom pressure is 0.09-0.14MPa.
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| CN105602613B (en) * | 2016-01-24 | 2017-10-31 | 太原理工大学 | The method of phenol, aromatic hydrocarbons and alkane in one-step method separation coal direct liquefaction oil |
| CN106588579B (en) * | 2016-12-07 | 2019-03-08 | 河北工业大学 | A method of extracting phenolic compound from carbolic oil |
| CN107089750B (en) * | 2017-04-28 | 2020-10-16 | 广东工业大学 | Treatment method of high-concentration phenol-containing wastewater |
| CN106986751B (en) * | 2017-05-25 | 2020-05-22 | 北京石油化工学院 | Method for extracting crude phenol from phenol oil |
| CN108034453B (en) * | 2017-11-14 | 2020-05-26 | 神华集团有限责任公司 | Method for extracting phenolic compounds from direct coal liquefaction oil |
| CN110015949B (en) * | 2019-05-16 | 2022-07-05 | 湘潭大学 | Method for extracting phenolic substances from raw oil containing phenol |
| CN112569633A (en) * | 2019-09-30 | 2021-03-30 | 青岛海德利纳米科技有限公司 | Method for separating, enriching or producing phenolic compounds, and method and equipment for processing oil products |
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| CN102219649B (en) * | 2011-04-22 | 2014-05-07 | 煤炭科学研究总院 | Method of extracting phenolic compound from coal liquefied oil or coal tar |
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