CN115141077B - Method for selectively separating anthracene from condensed ring aromatic compound - Google Patents
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- 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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- 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
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Abstract
The invention discloses a method for selectively separating anthracene from a condensed ring aromatic compound, which comprises the following steps: step one: firstly, preparing a naphthyl solvent and a mixture to be separated by a worker, and then, mixing the naphthyl solvent and the mixture to be separated according to a mass ratio of 1:1 to 8:1. Compared with the traditional solvent separation and purification method for anthracene, the naphthalene-based solvent used by the method has lower operation temperature and better solvent recovery performance, avoids the generation of a large amount of waste liquid in actual production, and has the advantages of low price, lower viscosity, improvement of mass transfer separation efficiency and reduction of equipment blockage compared with the conventional ionic liquid.
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 from coal tar anthracene oil fraction, is one of the most representative polycyclic aromatic hydrocarbons, and has three ring centers on a straight line, and has a molecular formula of C 14 H 10 The characteristic of the anthracene is expressed as pale yellow needle-shaped crystals, the anthracene has a fluorescent effect, the melting boiling point is higher, the melting boiling point is 215 ℃ and 340 ℃, anthracene has a larger application market in the chemical industry, and the single anthracene has high luminous efficiency, can be used for preparing luminescent materials, such as scintillators, sensors and the like, and in addition, the addition product of the anthracene can be used as one of the components of a special catalyst; the oxidation product anthraquinone has application in dye, paper making, medicine and other fields, and has great application value in both monomer anthracene and anthracene downstream productTherefore, it is important to obtain anthracene products of high purity by a simple separation method.
The anthracene is used as one of characteristic products of coal tar, the main separation means at present is that firstly, crude anthracene oil is obtained by cutting coal tar distillate, then the crude anthracene oil is further purified and refined, and the solvents such as heavy benzene and the like commonly used in industry at present are firstly removed for 1-2 times, and then the separation and purification are continuously carried out for many times by using a rectification method, a supercritical extraction method, a zone melting method, an emulsion film method, a solvent crystallization method, a solvent extraction method and the like, so that the industrial anthracene is obtained, the purity of the industrial anthracene is about 90% -95%, and the rectification method can be continuously operated, but the energy consumption is too high; the product obtained by the supercritical extraction method has higher purity, but the operation condition is harsh; the operation of the zone melting method is complex; the emulsion membrane method has low stability; the solvent consumption of the solvent crystallization method is large; the solvent extraction is difficult to find the solvent with high selectivity at present, and the used traditional solvent has higher operation temperature, higher toxicity, difficult recovery and easy environmental pollution.
The coal tar is rich in various polycyclic aromatic hydrocarbon, and due to the similar chemical structure, the effect similar to the hydrogen bond of nitrogen/sulfur heteroatom aromatic compound is difficult to form between the coal tar and the extractant, particularly, the isomer phenanthrene of anthracene has similar properties and almost the same boiling point (anthracene (340 ℃), phenanthrene (338 ℃)), so that the subsequent separation process is difficult, and the anthracene product with higher purity is difficult to obtain.
In view of the above problems, the invention provides a method for selectively separating anthracene from condensed ring aromatic compounds, which utilizes a naphthyl solvent to separate and purify anthracene products, 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 prior anthracene separation technical means, and the used naphthyl solvent can be efficiently recovered and utilized under the pollution-free condition by utilizing an environment-friendly stripping agent.
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 recycling.
In order to achieve the above purpose, the present invention provides the following technical solutions: a method for selectively separating anthracene from a fused ring aromatic compound, the method comprising the steps of:
step one: firstly, preparing a naphthyl solvent and a mixture to be separated by a worker, 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, then mixing and stirring the mixture by stirring equipment, reasonably controlling the stirring time to 20-80 min under the condition of 20-70 ℃, and then washing and filtering the mixture by the worker to obtain target products of anthracene and filtrate;
step two: and then the staff prepares the back extractant and the filtrate according to the mass ratio of 3:1-15:1, then the staff adds the back extractant into the filtrate and controls the temperature to be 10-30 ℃, when the mixture is stirred for 10-60 min, washing and suction filtration operation can be carried out, so that the filtrate and the solid product can be obtained and respectively placed.
Step three: and (3) distilling the filtrate obtained in the step two under reduced pressure, so that a recyclable regenerated solvent and stripping agent can be obtained:
preferably, the naphthalene-based solution in the first step comprises one or more of ethyl naphthalene, acetyl naphthalene, bromonaphthalene and chloronaphthalene.
Preferably, the mixture to be separated in the first step is a model compound or crude anthracene oil.
Preferably, the stripping agent 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 300-360 ℃ distillation section of coal tar.
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 method, the naphthalene-based solvent used by the method 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 conventional ionic liquid, can improve mass transfer separation efficiency, reduce the risk of equipment blockage, can finish the cyclic regeneration process by using the green nontoxic stripping agent, and reduces the production cost.
Detailed Description
All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the 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:
step one: firstly, preparing a naphthyl solvent and a mixture to be separated by a worker, 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, then mixing and stirring the mixture by stirring equipment, reasonably controlling the stirring time to 20-80 min under the condition of 20-70 ℃, and then washing and filtering the mixture by the worker to obtain target products of anthracene and filtrate;
step two: and then the staff prepares the back extractant and the filtrate according to the mass ratio of 3:1-15:1, then the staff adds the back extractant into the filtrate and controls the temperature to be 10-30 ℃, when the mixture is stirred for 10-60 min, washing and suction filtration operation can be carried out, so that the filtrate and the solid product can be obtained and respectively placed.
Step three: and (3) distilling the filtrate obtained in the step two under reduced pressure, so that a recyclable regenerated solvent and stripping agent can be obtained:
wherein, the naphthalene-based 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 first step 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 the distillation section of coal tar at 300-360 ℃.
Wherein the mass ratio of the alcohol to the water in the stripping agent is 1:1 to 8:1.
wherein the temperature of reduced pressure distillation in the third step is 40-70deg.C, and the time is 30-90min.
Example 1
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 1:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 3:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 5:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring at 30 ℃ for 60min, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of the acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 60min at 50 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then methylene dichloride is distilled off, and a model compound of anthracene and phenanthrene is obtained, wherein the mass ratio of ethyl naphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate solid, filtering again, continuously collecting the filter cake and the filtrate, and finally obtaining the anthracene product with the purity of 98.1% and the yield of 60%.
Example 8
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of chloronaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of phenanthrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then the methylene dichloride is distilled off, and the model compound of the anthracene and the phenanthrene is obtained, wherein the mass ratio of bromonaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 1g of naphthalene are weighed and mixed in methylene dichloride, stirred and heated at room temperature, and then distilled off
Dichloromethane to obtain model compounds of anthracene and phenanthrene, wherein the mass ratio of the acetylnaphthalene to the model compounds is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 0.5g of pyrene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then methylene dichloride is distilled off, and a model compound of anthracene and phenanthrene is obtained, wherein the mass ratio of acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and a filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene and 0.5g of fluoranthene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then methylene dichloride is distilled off, and a model compound of anthracene and phenanthrene is obtained, wherein the mass ratio of acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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
2g of anthracene, 0.5g of phenanthrene, 0.5g of naphthalene, 0.2g of pyrene and 0.2g of fluoranthene are weighed and mixed in methylene dichloride, stirring and heating are carried out at room temperature, then methylene dichloride is distilled off, and a model compound of anthracene and phenanthrene is obtained, wherein the mass ratio of acetylnaphthalene to the model compound is 2:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and a filtrate, adding a stripping agent into the filtrate to precipitate 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 acetylnaphthalene to the crude anthracene of 4:1, mixing the two materials in a sealed conical flask, stirring for 30min at 30 ℃, filtering, collecting a filter cake and filtrate, adding a stripping agent into the filtrate to precipitate 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 relational terms such as first and second, and the like are 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. Moreover, 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 understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (3)
1. A method for selectively separating anthracene from a condensed ring aromatic compound, the method comprising the steps of:
step one: firstly, preparing a naphthyl solvent and a mixture to be separated by a worker, 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, then mixing and stirring the mixture by stirring equipment, reasonably controlling the stirring time to 20-80 min under the condition of 20-70 ℃, and then washing and filtering the mixture by the worker to obtain target products of anthracene and filtrate;
step two: then the staff prepares the back extractant and the filtrate according to the mass ratio of 3:1-15:1, then the staff adds the back extractant into the filtrate and controls the temperature to be 10-30 ℃, when the mixture is stirred for 10-60 min, washing and suction filtration operation can be carried out, thus filtrate and solid products can be obtained and respectively placed;
step three: distilling the filtrate obtained in the second step under reduced pressure, so as to obtain a recyclable regenerated solvent and a recyclable stripping agent;
the naphthalene-based solution in the first step comprises one or more of ethyl naphthalene, acetyl naphthalene, bromonaphthalene and chloronaphthalene;
the mixture to be separated in the first step is a model compound or crude anthracene oil;
the model compound is one or more of anthracene, naphthalene, phenanthrene, fluorene, pyrene and fluoranthene;
the crude anthracene oil belongs to a 300-360 ℃ distillation section of coal tar;
the back extractant in the second step is ethanol-water mixed solution.
2. A method for selectively separating anthracene from a condensed ring aromatic compound according to claim 1, wherein: the mass ratio of ethanol to water in the stripping agent is 1:1 to 8:1.
3. a method for selectively separating anthracene from a condensed ring aromatic compound according to claim 1, wherein: the temperature of the reduced pressure distillation in the third step is 40-70 ℃ and the time is 30-90min.
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