CN115141077A - Method for selectively separating anthracene from condensed ring aromatic compound - Google Patents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
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- C07—ORGANIC CHEMISTRY
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- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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Abstract
The invention discloses a method for selectively separating anthracene from condensed ring aromatic compounds, which comprises the following steps: the method comprises the following steps: firstly, preparing a naphthyl solvent and a mixture to be separated by workers, and then mixing the naphthyl solvent and the mixture to be separated according to a mass ratio of 1:1 to 8: the ratio of 1 is configured. Compared with the traditional method for separating and purifying anthracene by using a solvent, the naphthyl solvent used in the method has the advantages of lower operation temperature, better solvent recovery performance and capability of avoiding the generation of a large amount of waste liquid in actual production.
Description
Technical Field
The invention belongs to the technical field of coal chemical industry, and particularly relates to a method for selectively separating anthracene from a condensed ring aromatic compound.
Background
Anthracene is an important product in the field of coal chemical industry, mainly comes from a coal tar anthracene oil distillation segment, is one of the most representative polycyclic aromatic hydrocarbons, has three ring centers on a straight line, and has a molecular formula of C 14 H 10 The character is light yellowThe acicular crystal has a fluorescence effect, the melting points are respectively 215 ℃ and 340 ℃, anthracene has a larger application market in the chemical industry, monomer anthracene has high luminous efficiency, and can be used for preparing luminescent materials, such as scintillators, sensors and the like, and in addition, an addition product of anthracene can be used as one of components of a special catalyst; the oxidation product anthraquinone is applied to the aspects of dye, paper making, medicine and the like, and downstream products of both monomer anthracene and anthracene have larger application value, so that the method for obtaining the high-purity anthracene product by the simple separation method has important significance.
Anthracene is used as one of characteristic products of coal tar, the main separation means at present is to cut coal tar fractions to obtain crude anthracene oil, and then further purify and refine the crude anthracene oil, heavy benzene and other solvents commonly used in the industry at present are firstly removed for 1-2 times, and then separation and purification are continuously carried out for multiple times by utilizing a rectification method, a supercritical extraction method, a zone melting method, an emulsion membrane method, a solvent crystallization method, a solvent extraction method and the like to obtain industrial anthracene, the purity of the industrial anthracene is about 90-95%, the rectification method can be continuously operated, but the energy consumption is too high; the product obtained by the supercritical extraction method has high purity, but the operation condition is harsh; the operation of the zone melting method is complicated; the stability of the emulsion membrane method is not high; the solvent crystallization method has large solvent consumption; at present, the solvent extraction is difficult to find a high-selectivity solvent, and the traditional solvent used has the defects of higher operation temperature, higher toxicity, difficult recovery and easy environmental pollution.
Coal tar is rich in various types of polycyclic aromatic hydrocarbons, and due to the similarity of chemical structures, the coal tar is difficult to form the effect similar to a nitrogen/sulfur heteroatom aromatic compound hydrogen bond with an extracting agent, particularly, the anthracene isomer phenanthrene has similar properties and almost the same boiling points (anthracene (340 ℃), phenanthrene (338 ℃)), so that the subsequent separation process is difficult, and an anthracene product with higher purity is difficult to obtain.
In view of the above problems, the present invention provides a method for selectively separating anthracene from a condensed ring aromatic compound, wherein a naphthyl solvent is used for separating and purifying an anthracene product, so as to solve the problems of complicated steps, high energy consumption, complex operation, harsh conditions, low solvent selectivity, difficult recovery, easy environmental pollution and the like in the existing anthracene separation technical means, and the used naphthyl solvent can be efficiently recycled by using an environmentally friendly back-extraction agent under the pollution-free condition.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for selectively separating anthracene from condensed ring aromatic compounds, which has the advantages of simple steps, high anthracene product purity and recyclability.
In order to achieve the purpose, the invention provides the following technical scheme: a method for selectively separating anthracene from a fused ring aromatic compound, the method comprising the steps of:
the method comprises the following steps: firstly, preparing a naphthyl solvent and a mixture to be separated by workers, and then mixing the naphthyl solvent and the mixture to be separated according to a mass ratio of 1:1 to 8:1, then adding a naphthyl solvent into a mixture to be separated by a worker, mixing and stirring the mixture by using stirring equipment, reasonably controlling the temperature to be 20-70 ℃ and the stirring time to be 20-80 min, and then washing and filtering the mixture by the worker to finally obtain a target product anthracene and a filtrate;
step two: and then, preparing a stripping agent and filtrate according to the mass ratio of 3:1-15 by a worker, adding the stripping agent into the filtrate by the worker, controlling the temperature to be 10-30 ℃, performing washing and suction filtration when stirring for 10-60 min, and respectively placing the filtrate and the solid product.
Step three: and (3) distilling the filtrate obtained in the second step under reduced pressure, so as to obtain a recyclable regeneration solvent and a stripping agent:
preferably, the naphthalene base solution in the first step includes one or more of ethyl naphthalene, acetyl naphthalene, bromonaphthalene and chloronaphthalene.
Preferably, the mixture to be separated in step one is a model compound or crude anthracene oil.
Preferably, the back extractant in the second step is a mixed solution of ethanol-water, methanol-water, n-propanol-water and n-butanol-water.
Preferably, the model compound is two or more of naphthalene, anthracene, phenanthrene, fluorene, pyrene and fluoranthene.
Preferably, the crude anthracene oil belongs to a coal tar distillation section at 300-360 ℃.
Preferably, the mass ratio of the alcohol to the water in the stripping agent is 1:1 to 8:1.
preferably, the temperature of the reduced pressure distillation in the third step is 40-70 ℃, and the time is 30-90min.
Compared with the prior art, the invention has the following beneficial effects:
compared with the traditional solvent separation and purification of anthracene, the naphthyl solvent used in the invention has lower operation temperature and better solvent recovery performance, avoids the generation of a large amount of waste liquid in actual production, has low price and lower viscosity compared with the currently commonly used ionic liquid, can improve mass transfer separation efficiency and reduce the risk of equipment blockage, can complete a cyclic regeneration process by using a green and nontoxic back-extraction agent, and reduces the production cost on the premise of ensuring environmental friendliness.
Detailed Description
All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a technical scheme that: a method for selectively separating anthracene from a fused ring aromatic compound, the method comprising the steps of:
the method comprises the following steps: firstly, preparing a naphthyl solvent and a mixture to be separated by workers, and then mixing the naphthyl solvent and the mixture to be separated according to a mass ratio of 1:1 to 8:1, then adding a naphthyl solvent into a mixture to be separated by a worker, mixing and stirring the mixture by using a stirring device, reasonably controlling the temperature to be 20-70 ℃, controlling the stirring time to be 20-80 min, then washing and filtering the mixture by the worker, and finally obtaining a target product anthracene and a filtrate;
step two: and then, preparing a stripping agent and filtrate according to the mass ratio of 3:1-15 by a worker, adding the stripping agent into the filtrate by the worker, controlling the temperature to be 10-30 ℃, performing washing and suction filtration when stirring for 10-60 min, and respectively placing the filtrate and the solid product.
Step three: and (3) distilling the filtrate obtained in the second step under reduced pressure, so as to obtain a recyclable regeneration solvent and a stripping agent:
wherein, the naphthyl solution in the first step comprises one or more of ethyl naphthalene, acetyl naphthalene, bromonaphthalene and chloronaphthalene.
Wherein, the mixture to be separated in the step one is a model compound or crude anthracene oil.
Wherein, the back extractant in the second step is a mixed solution of ethanol-water, methanol-water, n-propanol-water and n-butanol-water.
Wherein the model compound is two or more of naphthalene, anthracene, phenanthrene, fluorene, pyrene and fluoranthene.
Wherein, the crude anthracene oil belongs to a distillation section of coal tar at 300-360 ℃.
Wherein the mass ratio of alcohol to water in the stripping agent is 1:1 to 8:1.
wherein the temperature of reduced pressure distillation in the third step is 40-70 ℃ and the time is 30-90min.
Example 1
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 1:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 95.1% and the yield of 65%.
Example 2
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.5% and the yield of 75%.
Example 3
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 3:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.1% and the yield of 63%.
Example 4
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene into dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 5:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 98.8% and the yield of 67%.
Example 5
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 60min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.1% and the yield of 71%.
Example 6
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 60min at 50 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 98.9% and the yield of 63%.
Example 7
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of ethyl naphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, then adding a back-extraction agent into the filtrate to separate out a solid, filtering again, and continuously collecting the filter cake and the filtrate, wherein the purity of the obtained anthracene product is 98.1%, and the yield is 60%.
Example 8
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the chloronaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 96.5% and the yield of 70%.
Example 9
Weighing 2g of anthracene and 1g of phenanthrene, mixing the anthracene and the phenanthrene into dichloromethane, stirring and heating the mixture at room temperature, and then distilling the mixture to remove the dichloromethane to obtain a model compound of the anthracene and the phenanthrene, wherein the mass ratio of the bromonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 96.7% and the yield of 70%.
Example 10
Weighing 2g of anthracene and 1g of naphthalene, mixing the anthracene and the naphthalene in dichloromethane, stirring and heating the mixture at room temperature, and then distilling the mixture to remove
And (3) dichloromethane is adopted to obtain a model compound of anthracene and phenanthrene, and the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, then adding a back-extraction agent into the filtrate, separating out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.3% and the yield of 75%.
Example 11
Weighing 2g of anthracene and 0.5g of pyrene, mixing the anthracene and the pyrene in dichloromethane, stirring and heating at room temperature, and then distilling to remove the dichloromethane to obtain a model compound of anthracene and phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.3% and the yield of 72%.
Example 12
Weighing 2g of anthracene and 0.5g of fluoranthene, mixing the anthracene and the fluoranthene into dichloromethane, stirring and heating the mixture at room temperature, and then distilling the mixture to remove the dichloromethane to obtain a model compound of anthracene and phenanthrene, wherein the mass ratio of the acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.1% and the yield of 73%.
Example 13
Weighing 2g of anthracene, 0.5g of phenanthrene, 0.5g of naphthalene, 0.2g of pyrene and 0.2g of fluoranthene, mixing the materials in dichloromethane, stirring and heating at room temperature, and then distilling to remove dichloromethane to obtain a model compound of anthracene and phenanthrene, wherein the mass ratio of acetonaphthalene to the model compound is 2:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.0% and the yield of 71%.
Example 14
According to the mass ratio of the acetyl naphthalene to the crude anthracene of 4:1, mixing the two in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a back-extraction agent into the filtrate to separate out a solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 99.0% and the yield of 70%.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. A method for selectively separating anthracene from a fused ring aromatic compound, comprising the steps of:
the method comprises the following steps: firstly, preparing a naphthyl solvent and a mixture to be separated by workers, and then mixing the naphthyl solvent and the mixture to be separated according to a mass ratio of 1:1 to 8:1, then adding a naphthyl solvent into a mixture to be separated by a worker, mixing and stirring the mixture by using a stirring device, reasonably controlling the temperature to be 20-70 ℃, controlling the stirring time to be 20-80 min, then washing and filtering the mixture by the worker, and finally obtaining a target product anthracene and a filtrate;
step two: and then, preparing a stripping agent and filtrate according to the mass ratio of 3:1-15 by a worker, adding the stripping agent into the filtrate by the worker, controlling the temperature to be 10-30 ℃, performing washing and suction filtration when stirring for 10-60 min, and respectively placing the filtrate and the solid product.
Step three: and (3) distilling the filtrate obtained in the second step under reduced pressure, so as to obtain a recyclable regeneration solvent and a stripping agent:
2. the method of claim 1 for the selective separation of anthracene from fused ring aromatic compounds, wherein: the naphthyl solution in the first step comprises one or more of ethyl naphthalene, acetyl naphthalene, bromonaphthalene and chloronaphthalene.
3. The method of claim 1 for the selective separation of anthracene from fused ring aromatic compounds, wherein: and the mixture to be separated in the step one is a model compound or crude anthracene oil.
4. The method according to claim 1, wherein the fused-ring aromatic compound is one of the following aromatic compounds: the back extractant in the second step is a mixed solution of ethanol-water, methanol-water, n-propanol-water and n-butanol-water.
5. The method of claim 3, wherein the fused ring aromatic compound comprises at least one of: the model compound is two or more of naphthalene, anthracene, phenanthrene, fluorene, pyrene and fluoranthene.
6. The method of claim 3, wherein the fused ring aromatic compound comprises at least one of: the crude anthracene oil belongs to a distillation section of coal tar at 300-360 ℃.
7. The method according to claim 4, wherein the fused-ring aromatic compound is one of the following aromatic hydrocarbon compounds: the mass ratio of alcohol to water in the stripping agent is 1:1 to 8:1.
8. the method according to claim 1, wherein the fused-ring aromatic compound is one of the following aromatic compounds: the temperature of the reduced pressure distillation in the third step is 40-70 ℃, and the time is 30-90min.
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