CN110204475B - Method for separating indole from coal tar by using double-site pyrrolidone ionic liquid - Google Patents
Method for separating indole from coal tar by using double-site pyrrolidone ionic liquid Download PDFInfo
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/06—Preparation of indole from coal-tar
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/18—Working-up tar by extraction with selective solvents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
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Abstract
The invention relates to a method for extracting and separating indole from coal tar by using a double-site ionic liquid. The method is characterized in that: the designed pyrrolidone-based double-acting-site ionic liquid is used as an extracting agent, the extracting agent and quantitative and fixed-concentration indole model oil are stirred at room temperature, and two layered phases are obtained after standing, so that effective separation of an indole fraction mixture is realized; separating out a lower-layer ionic liquid phase in a liquid separation mode, continuously adding the same amount of indole model oil for extraction, and performing extraction when the concentration of the indole model oil is 3%, the solvent-oil ratio is 1: 1, the extractant still shows strong extraction separation capacity after 10 times of cyclic extraction; separating the last extraction phase by liquid separation, adding a back-extraction agent, stirring, standing for layering, regenerating the ionic liquid extraction agent at the lower layer, and rectifying the back-extraction agent from the upper layer to obtain the separated indole. The double-site pyrrolidone ionic liquid extractant used in the invention has low viscosity, environmental protection, strong circulating extraction capability, repeated use and high single extraction rate of more than 99%.
Description
Technical Field
The invention belongs to the field of separation in the coal chemical industry, and relates to synthesis of a low-viscosity and high-efficiency ionic liquid extractant and application of the extractant in separation of indole components in coal tar.
Background
Pyrolysis oil produced during coal pyrolysis serves as an important source of high value-added products, such as: light oil, phenol oil, wash oil, anthracene oil, naphthalene oil, asphalt and the like have been widely applied in industries such as chemical industry, medicine, dye, pesticide, plastics, synthetic fiber, synthetic rubber, fire-resistant high-temperature material, national defense industry, carbon and the like, wherein a part of polycyclic aromatic hydrocarbon compounds cannot be replaced by petroleum industry, such as: about 90% of naphthalene, biphenyl, anthracene, acenaphthene, indole, pyridine and other products come from tar refining processing, and almost 100% of carbazole, quinoline and thiophene come from separation of tar products. Wherein, the indole is a compound formed by connecting pyrrole and benzene in parallel, and is also called as benzopyrrole. Indoles and homologues have a relatively high distribution in the coal tar distillate, which has a very high value of use in production in view of the limited source of indole. Therefore, the method is very meaningful for separating high-value-added compounds such as indole in the coal tar.
At present, many documents report methods for separating specific high value-added components from coal tar and fractions thereof, and the methods are usually rectification, crystallization, solvent extraction and the like. However, the high temperature condition of the rectification separation can cause chemical changes of part of high-boiling-point aromatic compounds, thereby reducing the grade and purity of the product. Therefore, the rectification is generally used as a pretreatment process of the coal tar, and is cut into different distillation sections according to the temperature, single-component substances with similar boiling points are enriched into corresponding fractions, and then the corresponding products are obtained through further separation and refining. Compared with the operation of a rectification unit, the crystallization operation has the advantages of low working temperature, low energy consumption, low reflux ratio and the like, but in consideration of the extreme complexity of tar and fractions thereof, the separation of multiple and complex components cannot be realized by one-step crystallization, so that the crystallization method can be used for further purifying products. In the Separation of the coal pyrolysis oil component, Yamamoto et al Separation of high purity indole from coal tar by high pressure crystallization, Fuel 1991, 70(4): 565-.
Compared with the two methods, the solvent extraction separation, especially the liquid-liquid extraction, has the advantages of large productivity, high recoverability, low product cost and the like, and the method is widely applied to the coking industry. Kim et al [ composite of methane with formamide on separation of nitro chemical compounds from model tar reaction by methanol aqueous solution as solvent, separation studies were carried out on indole-containing simulated coal tar fractions, recovery rate of which exceeds 90% by three-stage equilibrium extraction, and extractant can be recycled, which has relatively high industrial application prospect, but the method has insufficient selectivity when the system to be separated is complicated. Therefore, ionic liquids have been widely studied and applied in component separation or removal in view of their high selectivity and designability. In addition, the separation of indole in coal tar has also been reported, Jianao et al [ An ionic liquid extraction process for the separation of indole from water oil, Green chem. 2015, 17 (7): 3783-3790 ] use [ Bmim ] [ BF4] to extract indole in the wash oil fraction with An extraction rate of greater than 90%, and can be recycled, but this ionic liquid can decompose harmful HF gas under certain conditions; zhang et al [ effective extraction of neutral heterocyclic reagent compounds from co-axial tar of ionic liquids and its mechanism analysis. Energy Fuels 2018, 32, (9), 9358-. Therefore, in consideration of the advantages of the ionic liquid, an ionic liquid extracting agent which is stable in thermodynamic property, low in viscosity, green and economical is found to realize efficient and high-selectivity separation of indole in coal tar and fractions thereof, and the method is very significant for deep utilization of the coal tar.
Disclosure of Invention
[ problem to be solved ]
The invention aims to design an ionic liquid extracting agent with double acting sites aiming at the problems existing in the separation of indole in the prior coal tar and fractions thereof, and provides a method for efficiently separating indole. The method takes the ionic liquid of the pyrrolidone-based double-acting site as an extracting agent, and realizes the separation of indole in the coal tar and the fraction thereof by the way that strong polar atoms contained in anions and cations form hydrogen bond interaction with indole.
[ solution ]
The purpose of the invention is realized by the following technical scheme.
The invention provides a method for extracting and separating indole in coal tar by using a double-site pyrrolidone ionic liquid extractant, which comprises the following steps:
(1) adding a certain amount of bi-site pyrrolidone base ionic liquid into indole model oil, stirring at a certain temperature, standing for phase separation to finally obtain an upper oil phase and a lower indole-containing ionic liquid phase from which indole is removed;
(2) continuously adding the same amount of indole model oil into the lower-layer ionic liquid phase obtained in the step (1) for extraction, stirring and standing for phase separation, obtaining an ionic liquid phase after cyclic extraction from the lower layer, and performing cyclic extraction again on the ionic liquid phase obtained after phase separation;
(3) and (2) adding a back extractant into the lower ionic liquid phase obtained in the step (1), stirring, standing and phase splitting, wherein the upper layer is a back extractant phase containing indole, and the lower layer is an ionic liquid extractant. The double-site pyrrolidone ionic liquid extractant is reused;
(4) and (3) distilling the solution containing the indole stripping agent obtained in the steps (1) and (2) to obtain the product indole and the stripping agent, and regenerating the stripping agent for use.
In the above method, the pyrrolidone-based ionic liquid extractant includes: the ionic liquid structure is obtained by randomly combining 1-hydroxyethyl pyrrolidone cations, N-methyl-1- (1, 2-dyhydroxy) propyl pyrrolidone cations, 1-ethyl pyrrolidone cations, acetate anions, p-toluenesulfonic acid anions and other anions and cations.
In the method, the solvent oil in the adopted indole model oil is composed of different aromatic hydrocarbons, straight-chain alkane or a mixture thereof and indole. Wherein, the aromatic hydrocarbon is one or more of benzene, toluene and xylene; the aliphatic hydrocarbon is one or more of n-hexane, n-heptane, n-octane, n-dodecane and n-hexadecane); or a coal tar distillate fraction containing indole.
In the method, the molar ratio of the double-site pyrrolidone ionic liquid extractant to the indole model oil is 0.05-2.0.
In the method, the temperature for separating indole by using the double-site pyrrolidone radical ionic liquid extractant is 0-100 ℃, and the separation time is 1-60 min.
In the method, the circulating extraction times of the two-site pyrrolidone base ionic liquid extractant for separating indole are 1-15 times.
In the method, the back-extraction agent adopted in the step (3) is diethyl ether, butyl acetate and acetone.
In the method, the mass ratio of the back extractant adopted in the step (3) to the liquid phase containing the indole ions is 1-20, and the temperature in the regeneration of the back extractant is 0-50 ℃.
In the method, the temperature for distilling the stripping agent solution containing indole in the step (4) is 40-150 ℃.
The principle of the method is as follows: the indole and the strong polar atom on the double-site ionic liquid extractant can generate intermolecular hydrogen bond action, thereby realizing the high-efficiency and high-selectivity separation of the indole in the coal tar and the fraction thereof. The pyrrolidone-based ionic liquid extractant disclosed by the patent has the structures of partial carbonyl, hydroxyl and the like, has lower viscosity, higher stability, extraction capacity and selectivity compared with a common ionic liquid extractant, and can be regenerated. The extraction efficiency is 80-99.5%, and the single extraction rate of more than 99% can be realized under the optimal condition.
[ advantageous effects ]
Compared with the prior art, the invention mainly has the following beneficial effects:
the double-site pyrrolidone ionic liquid extractant used in the invention has high extraction efficiency, stable property, low viscosity and strong cyclic extraction capability; the extracted ionic liquid can be regenerated by the back-extracting agent such as ether or ester, the reuse of the extracting agent can be realized, and the separation efficiency is hardly reduced.
Detailed Description
The present invention will be further described with reference to specific examples, which are provided for the extractive separation of indole from coal tar and fractions thereof by using a dual-site pyrrolidone-based ionic liquid extractant and the regeneration method thereof, but are not limited to the following examples, and variations within the scope of the present invention are included in the technical scope of the present invention.
The formulation method of the model oil used in the following examples was:
preparing indole model oil: 30.00g of indole is accurately weighed and dissolved in toluene, and diluted to 500ml to prepare 60g/L model oil.
Preparing mixed model oil: coal tar or its different fractions are complex in composition and mainly consist of hydrocarbons (aromatic hydrocarbons, aliphatic hydrocarbons), neutral, acidic or basic substances. In the preparation of the indole model oil, naphthalene (represented by naphthalene substances), phenol (represented by acidic substances) and quinoline (represented by alkali substances) are added, and the model oil with the corresponding mass ratio is prepared by referring to the composition of the above partial substances in real fractions. 29.10g of indole, 19.72g of phenol, 32.30g of quinoline and 96.19g of naphthalene are accurately weighed and dissolved in toluene, and diluted to 500ml to prepare model oil with the contents of 58.20g/L of indole, 39.44g/L of phenol, 64.60g/L of quinoline and 192.38g/L of naphthalene.
Ionic liquid extractant extraction separation experiment: measuring a certain amount of model oil in a sample bottle with magnetons, adding a certain amount of ionic liquid extractant, stirring at room temperature for 5-60min, standing for 30min, absorbing a proper amount of upper raffinate phase polarity for quantitative analysis by a gas chromatograph, measuring the content of indole before and after extraction, and calculating the extraction rate of indole by ionic liquid; and continuously adding the same amount of indole model oil into the obtained lower-layer ionic liquid phase for extraction, stirring, standing for phase separation, obtaining the ionic liquid phase after cyclic extraction from the lower layer, and performing cyclic extraction again on the ionic liquid phase obtained after phase separation.
Ionic liquid extractant regeneration experiment: standing the obtained lower extraction phase, transferring to another container, adding quantitative back-extraction agent into the container, stirring at room temperature for 30min, standing until the mixed solution is thoroughly layered, wherein the upper layer is indole and the back-extraction agent, and distilling the back-extraction agent at a certain temperature to obtain indole; the lower layer is regenerated ionic liquid after back extraction.
Analyzing the composition of raffinate phase by gas chromatography, and separating with Shimadzu GC-2014 gas chromatograph column (DB-WAX (30 m × 0.53 mm × 0.5 μm) capillary column and hydrogen flame ionization detector; n-methylpyrrolidone is used as an internal standard substance, nitrogen is used as carrier gas, the temperature of a vaporization chamber is 250 ℃, the temperature of a detector is 260 ℃, and the temperature programming is as follows: keeping at 100 deg.C for 3min, heating to 210 deg.C at 30 deg.C/min, and keeping for 6 min.
Example 1
Taking 10.12g of model oil, adding 2.01g of double-site pyrrolidone ionic liquid-1-hydroxyethyl pyrrolidone acetate into a sample bottle, stirring at 25 ℃ for 30min, standing for 30min, taking an upper extraction raffinate sample, analyzing and determining the indole content by using a gas chromatograph, and calculating to obtain the single extraction rate of 85.48%; under the condition, the extraction rate is not obviously reduced after model oil with the same concentration is circularly extracted for 8 times. Adding 20mL of diethyl ether into the lower extraction phase, back-extracting for 40min under room temperature magnetic stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid in the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extractant, and the recovery rate is 96.63%.
Example 2
Taking 10.09g of model oil into a sample bottle, adding 2.02g of double-site pyrrolidone ionic liquid-1-hydroxyethyl pyrrolidone p-toluenesulfonate, stirring at 25 ℃ for 10min, standing for 30min, taking an upper extraction raffinate sample, analyzing and determining the indole content by using a gas chromatograph, and calculating to obtain the extraction rate of 97.98%; under the condition, the extraction rate is not obviously reduced after 10 times of circulating extraction of model oil with the same concentration. Adding 20mL of butyl acetate into the lower extraction phase, back-extracting for 30min under room temperature magnetic stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid in the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extractant, and the recovery rate is 95.92%.
Example 3
Adding 9.98g of model oil into a sample bottle, adding 1.99g of double-site pyrrolidone ionic liquid-N-methyl-1- (1, 2-dihydroxy) propyl pyrrolidone acetate, stirring at 25 ℃ for 600min, standing for 30min, taking an upper extraction raffinate sample, analyzing and determining the indole content by using a gas chromatograph, and calculating to obtain the extraction rate of 87.27%; under the condition, the extraction rate is not obviously reduced after model oil with the same concentration is circularly extracted for 8 times. Adding 20mL of diethyl ether into the lower extraction phase, back-extracting for 40min under room temperature magnetic stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid in the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extracting agent, and the recovery rate is 94.64 percent.
Example 4
Taking 10.03g of model oil, adding 2.03g of double-site pyrrolidone ionic liquid-N-methyl-1- (1, 2-dihydroxy) propyl pyrrolidone p-toluenesulfonate into a sample bottle, stirring at 25 ℃ for 10min, standing for 30min, taking an upper extraction raffinate sample, analyzing and determining the indole content by using a gas chromatograph, and calculating to obtain the extraction rate of 94.82%; under the condition, the extraction rate is not obviously reduced after the model oil with the same concentration is circularly extracted for 10 times. Adding 20mL of diethyl ether into the lower extraction phase, back-extracting for 40min under room temperature magnetic stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid in the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extractant, and the recovery rate is 95.33 percent.
Example 5
And (2) putting 9.95g of model oil into a sample bottle, adding 1.97g of pyrrolidone ionic liquid-1-ethyl pyrrolidone acetate, stirring at 25 ℃ for 30min, standing for 30min, taking an upper extraction raffinate sample, analyzing and determining the indole content by using a gas chromatograph, and calculating to obtain the extraction rate of 78.08%. Adding 20mL of butyl ether into the lower-layer extraction phase, back-extracting for 40min under room-temperature magneton stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid in the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extractant, and the recovery rate is 98.14%.
Example 6
10.09g of model oil is taken out to be put into a sample bottle, 2.04g of pyrrolidone ionic liquid-1-ethyl pyrrolidone p-toluenesulfonate is added, the mixture is stirred for 60min at 25 ℃, then is kept stand for 30min, an upper extraction raffinate phase sample is taken to be analyzed and measured by a gas chromatograph, and the extraction rate is calculated to be 79.25%. Adding 20mL of diethyl ether into the lower extraction phase, back-extracting for 40min under room temperature magnetic stirring, standing for 20min, and distilling the upper layer to obtain indole; the ionic liquid at the lower layer is transferred into a vacuum drying oven to be dried for 5 hours at the temperature of 50 ℃ to regenerate the ionic liquid extracting agent, and the recovery rate is 98.85 percent.
Claims (5)
1. A method for extracting and separating indole in coal tar by using a double-site pyrrolidone ionic liquid extractant is characterized by comprising the following steps:
(1) adding a double-site pyrrolidone base ionic liquid into indole model oil, stirring at room temperature, standing for phase separation, and finally obtaining an upper oil phase with indole removed and a lower ionic liquid phase with indole;
wherein: the indole model oil is composed of solvent oil and indole, or is a coal tar distillate section containing indole; wherein the solvent oil is aromatic hydrocarbon, straight-chain alkane or a mixture thereof, the aromatic hydrocarbon is one or more of benzene, toluene and xylene, and the straight-chain alkane is one or more of n-hexane, n-heptane, n-octane, n-dodecane and n-hexadecane; the double-site pyrrolidone ionic liquid is an ionic liquid structure obtained by randomly combining 1-hydroxyethyl pyrrolidone cations, N-methyl-1- (1, 2-dihydroxy) propyl pyrrolidone cations, 1-ethyl pyrrolidone cations, acetate anions and p-toluenesulfonate anions;
(2) continuously adding the same indole model oil into the lower-layer ionic liquid phase obtained in the step (1) for extraction, stirring, standing for phase separation, obtaining an ionic liquid phase subjected to cyclic extraction at the lower layer, and performing cyclic extraction on the obtained ionic liquid phase again after phase separation;
(3) adding a back-extraction agent into the lower-layer ionic liquid phase obtained in the step (1) or (2), wherein the back-extraction agent is one of ethyl ether, butyl ether and butyl acetate, stirring, standing and phase-separating, the upper layer is an indole-containing back-extraction agent phase, the lower layer is an ionic liquid extraction agent, and the double-site pyrrolidone-based ionic liquid extraction agent can be recycled;
(4) and (4) distilling the back extractant phase containing the indole obtained in the step (3) to obtain the product indole and the back extractant, wherein the back extractant is reused.
2. The method of claim 1, wherein the mass ratio of the dual-site pyrrolidone-based ionic liquid extractant to the indole model oil is 0.05 to 2.0.
3. The method as claimed in claim 1, wherein the number of the extraction cycles of the dual-site pyrrolidone-based ionic liquid extractant for indole separation in the step (2) is 1-15.
4. The method according to claim 1, wherein the mass ratio of the stripping agent used in the step (3) to the indole ion-containing liquid phase is 1 to 20.
5. The process according to claim 1, wherein the temperature at which the stripping agent solution containing indole in step (4) is distilled is 40 to 150 ℃.
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| Efficient Extraction of Neutral Heterocyclic Nitrogen Compounds from Coal Tar via Ionic Liquids and Its Mechanism Analysis;Lianzheng Zhang等;《Energy & Fuels》;20180827;第32卷;全文 * |
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