CN111089890A - Method for testing solubility parameters of mixed hydrocarbons and method for processing heavy diesel oil fractions - Google Patents

Method for testing solubility parameters of mixed hydrocarbons and method for processing heavy diesel oil fractions Download PDF

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CN111089890A
CN111089890A CN201811242551.3A CN201811242551A CN111089890A CN 111089890 A CN111089890 A CN 111089890A CN 201811242551 A CN201811242551 A CN 201811242551A CN 111089890 A CN111089890 A CN 111089890A
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component
solvent
raffinate
solubility parameter
extraction
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CN111089890B (en
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彭东岳
管翠诗
丁洛
王玉章
蔡晨
陈国成
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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China Petroleum and Chemical Corp
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
    • C10G53/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step
    • C10G53/06—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step including only extraction steps, e.g. deasphalting by solvent treatment followed by extraction of aromatics
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1055—Diesel having a boiling range of about 230 - 330 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1059—Gasoil having a boiling range of about 330 - 427 °C
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/04—Diesel oil

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Abstract

The invention relates to the field of petrochemical industry, and discloses a method for testing solubility parameters of mixed hydrocarbons and a method for processing heavy diesel oil fractions, wherein the method for processing the heavy diesel oil fractions comprises the following steps: (1) introducing the heavy diesel oil fraction and a first polar solvent into a first extraction tower for first solvent extraction separation to respectively obtain a first extract and a first raffinate; (2) introducing the first raffinate and the second polar solvent into a second extraction tower for second solvent extraction separation; the first polar solvent has a polarity higher than that of the second polar solvent, and the conditions for the extraction and separation of the first solvent are controlled so that the solubility parameter of the first raffinate is less than 20 (J-cm)‑3)0.5. The raffinate oil obtained by the method for processing the heavy diesel oil fraction has high alkane content and high cetane number, and can be used as a blending component of diesel oil; the extract oil has high aromatic hydrocarbon content and low alkane content, and can be developed to have high adsorptionValue-added aromatic-rich product.

Description

Method for testing solubility parameters of mixed hydrocarbons and method for processing heavy diesel oil fractions
Technical Field
The invention relates to the field of petrochemical industry, in particular to a method for testing solubility parameters of mixed hydrocarbons and a method for processing heavy diesel oil fractions by using the method.
Background
With the continuous increase of oil refining scale and the adjustment of energy structure in China, diesel consumption in China begins to rapidly slide down, so that the diesel capacity is seriously excessive. In addition, the proportion of catalytic cracking (FCC) diesel oil in the diesel pool in China is higher, and accounts for about 30 percent. However, as crude oil is increasingly heavy and the processing depth is increased, the quality of catalytic cracking diesel oil is poor, and the specific gravity of heavy diesel oil is increased continuously. In the heavy diesel oil, the aromatic hydrocarbon, especially polycyclic aromatic hydrocarbon, is high in content, the cetane number is low, and the increasingly strict diesel oil standard is difficult to meet.
How to digest the excessive heavy diesel oil and improve the quality of the diesel oil at the same time becomes a difficult problem which troubles refineries.
The traditional treatment method adopts hydro-upgrading to saturate aromatic hydrocarbon in the catalytic cracking diesel oil, and the aromatic hydrocarbon is used as a blending component of the diesel oil after the cetane number is improved by a certain value. However, the hydro-upgrading process has severe operating conditions and higher operating cost, which leads to a great increase in the production cost of diesel oil. Therefore, there is a need to develop a low-cost and high-efficiency upgrading technology to convert a part of FCC diesel oil into other high value-added petrochemicals, digest the surplus diesel oil, improve the quality of the diesel oil, and increase the refinery profit.
The liquid-liquid extraction technology can effectively separate saturated hydrocarbon and aromatic hydrocarbon, and BTX and high-quality gasoline can be produced by liquid-liquid extraction and extractive distillation in the aspect of gasoline separation. In the context of lubricant oil production, vacuum distillate oils can be refined to base oils by liquid-liquid extraction. The liquid-liquid extraction technology can not only improve the quality of oil products, but also obtain obvious economic benefit, but also has less research on the separation and application of heavy diesel components.
CN103695033A discloses a method for improving the cetane number of catalytic cracking diesel oil. The method is characterized in that catalytic cracking diesel oil is subjected to hydrofining and hydro-upgrading treatment, and then fraction with a boiling point higher than 180 ℃ is subjected to aromatic extraction. The obtained raffinate oil is diesel oil with high cetane number, and the extract oil is returned to the hydrogenation treatment for aromatic saturation reaction. The method can improve the cetane number of the catalytic cracking diesel oil by more than 20 units. However, the hydrofining and hydro-upgrading process of the method in the prior art has harsh operating conditions and higher operating cost.
CN104073285A discloses a method for extracting and separating aromatic hydrocarbons in diesel oil. Aromatic hydrocarbons in the catalytic cracking diesel oil are separated by adopting a method of feeding two-stage extraction solvents, wherein the used extraction solvents are organic amine compounds or ether compounds, and the cosolvent is water. The method has the advantages of low solvent ratio, no need of raffinate oil reflux, low energy consumption of the device, and high raffinate oil yield. However, for heavy diesel oil fractions, the extraction solvent is close to the diesel oil fraction in density and does not allow an efficient separation.
CN104945327A discloses a solvent and a method for extracting and separating aromatic hydrocarbon and alkane in diesel oil fraction. In the prior art, ionic liquid is used as a solvent, and the ionic liquid is imidazole or pyridine cations. By varying the number of carbon atoms in the substituents, the solubility to aromatics in diesel fractions can be increased. In addition, the aromatic hydrocarbon in the ionic liquid is recovered by adopting a back extraction method, so that the aromatic hydrocarbon is separated from the ionic liquid, and the utilization efficiency of an extraction solvent is improved. The raffinate oil obtained by the prior art has higher cetane number and can meet the quality standard of diesel oil. However, the large-scale industrial application still faces the problems of high manufacturing cost, easy water absorption, high energy consumption for recovery and the like of the ionic liquid.
CN102021025A discloses a system for preparing high-quality diesel oil and a method thereof. The system removes a part of aromatic hydrocarbon in the diesel oil through solvent extraction. And (3) carrying out hydrogenation treatment on the raffinate oil to obtain high-quality diesel oil, separating the extract oil containing aromatic hydrocarbon, returning the lightest components serving as a backwashing agent to the bottom of the extract oil backwashing tower and the bottom of the extraction tower, and discharging the rest components out of the system. The method has strong adaptability of raw materials, improves cetane number of diesel oil, and reduces condensation point of diesel oil. However, for heavy diesel oil with high aromatic content, the solvent is mutually soluble with the diesel oil in the extraction process, and the separation operation cannot be carried out.
The solvent extraction technology is an effective method for separating polycyclic aromatic hydrocarbon components in heavy diesel oil and improving the quality of the diesel oil. However, the existing extraction technology mainly aims at catalytic cracking diesel oil with the aromatic hydrocarbon content of 30-70%. As feedstock heaviness and catalytic cracking severity increase, the heavy diesel fraction increases with its high aromatics content (aromatics content greater than 70%). It has been discovered in the prior art (CN104073285A, CN101861374A) that heavy diesel oil fractions with high aromatic content (aromatic content greater than 70%) are miscible with low polar solvents such as furfural, N-methylpyrrolidone, etc., and are difficult to separate. However, no relevant research is currently involved with diesel fractions. For high-polarity solvents such as dimethyl sulfoxide and the like, the solvents can extract and separate heavy diesel oil fractions, but the raffinate oil has high aromatic hydrocarbon content and poor quality, and the extraction effect is unsatisfactory.
In addition, the density of the heavy diesel oil is usually 0.85-1 g/cm3The extraction treatment needs to be carried out by selecting a solvent with a higher density. In addition, in the solvent extraction process, the screening principle of the solvent and the control and optimization of the refining depth are lack of effective standards and methods.
Therefore, in order to realize the modification of the heavy diesel oil fraction, a separation process with proper polar solvent, low ratio of a starter, proper extraction temperature, high separation efficiency and good quality needs to be screened.
Disclosure of Invention
The invention aims to overcome the problem of difficult separation caused by mutual solubility with a solvent in the process of processing heavy diesel oil fractions by using the method in the prior art, and provides a method for testing solubility parameters of mixed hydrocarbons and a method for processing the heavy diesel oil fractions by using the method.
The inventor of the invention finishes the technical scheme of the invention based on the following thought: the solubility parameter of the pure substance can be obtained by literature reference, a drop weight test method, a radical contribution method and other estimation methods. For mixed hydrocarbons such as diesel oil and the like, the solubility parameter is difficult to refer; the drop weight test method needs to measure the solubility parameters of a solution formed by various solvents and mixed hydrocarbons, and has complex operation and poor economical efficiency. The group contribution method requires a large amount of data calculation and processing procedures for the mixed hydrocarbon calculation, and the mixture calculation accuracy is poor. Therefore, it is of great practical interest to provide a method for testing the solubility parameter of mixed hydrocarbons.
In order to achieve the above object, a first aspect of the present invention provides a method of testing solubility parameters of mixed hydrocarbons, the method comprising:
(1) the hydrocarbon composition A is set in the mixed hydrocarbon, and the mixed hydrocarbon contains paraffin, single naphthenic hydrocarbon, dicycloalkane, tricycloalkane, alkylbenzene, indane, tetralin, indene, octahydrophenanthrene and CnH2n-10Naphthalene, acenaphthene, CnH2n-14Acenaphthylene, fluorene, CnH2n-16Phenanthrenes, CnH2n18 and at least three of the benzothiophenes as component A1Component A2.mM is a positive integer not less than 3, n is a positive integer not less than 10;
(2) testing the mixed hydrocarbon to be tested as the component A1Component A2.mThe composition of the hydrocarbons and the mass percentage of the corresponding components;
(3) according to the average relative molecular mass M of the mixed hydrocarbon to be detectedMixing ofAnd the types of the components respectively construct the molecular formula of each component, and the constructed molecular formula of each component enables the relative molecular mass of each component and the MMixing ofThe difference between the two is less than or equal to 7, and the relative molecular mass of each component is M1、M2.m；
(4) Respectively constructing a molecular structural formula of each component according to the type and the molecular formula of each component to obtain a model compound of each component, so that the obtained model compound of each component respectively corresponds to each component in the mixed hydrocarbon to be detected, and the model compound optionally further contains saturated alkyl so that the relative molecular mass of the model compound of each component is equal to the relative molecular mass of a substance represented by the molecular formula of each corresponding component;
(5) calculating the solubility parameter of the model compound of each component, which is r1、r2.m；
(6) Calculating the solubility parameter r of the mixed hydrocarbon to be measured according to the formula L1Mixing of，
L1: solubility parameter r of the hydrocarbon mixture to be measuredMixing ofThe solubility parameter of the model compound for each component x the mass percent content of each component.
A second aspect of the invention provides a process for processing a heavy diesel fraction, the process comprising:
(1) introducing the heavy diesel oil fraction and a first polar solvent into a first extraction tower for first solvent extraction separation to respectively obtain a first extract and a first raffinate; introducing the first extract into a first solvent recovery tower for first solvent recovery, and obtaining a first aromatic-rich component;
(2) introducing the first raffinate and the second polar solvent into a second extraction tower for second solvent extraction separation to respectively obtain a second extract and a second raffinate; introducing the second extract into a second solvent recovery tower for second solvent recovery, and obtaining a second aromatic-rich component;
the first polar solvent has a stronger polarity than the second polar solvent, and the heavy diesel fraction has a carbon number distribution of 12-25 and a solubility parameter of not less than 20 (J-cm)-3)0.5(ii) a And
controlling the conditions of the first solvent extraction separation so that the solubility parameter of the first raffinate is less than 20 (J-cm)-3)0.5；
Wherein the solubility parameter of the heavy diesel fraction and the solubility parameter of the first raffinate are obtained from the process tests described in the first aspect of the invention.
The method of the present invention can obtain solubility parameter of mixed hydrocarbon with low cost and simple operation, and can process carbon number distribution in the range of 12-25 and solubility parameter of 20 (J-cm) or more by using the measured solubility parameter-3)0.5The heavy diesel fraction of (2). The present invention provides a processed carbon number distribution in the range of 12 to 25 and a solubility parameter of 20(J · cm or more)-3)0.5The method for separating the heavy diesel oil fraction has the advantages of simple and convenient separation and good separation effect.
In addition, the raffinate oil obtained by the method for processing the heavy diesel oil fraction has high alkane content and high cetane number, and can be used as a blending component of diesel oil; the extracted oil has high aromatic hydrocarbon content and low alkane content, and aromatic hydrocarbon-rich products with high added value can be developed.
Drawings
Figure 1 is a process flow diagram for processing a heavy diesel fraction according to a preferred embodiment of the present invention.
Description of the reference numerals
1. First extraction tower 2 and second extraction tower
3. First solvent recovery tower 4 and second solvent recovery tower
5. Third solvent recovery column 6, heavy diesel oil fraction
7. First polar solvent 8, first extract
9. First raffinate 10, second polar solvent
11. Second extract 12, second raffinate
13. First aromatic-rich component 14, recovered first polar solvent
15. Second aromatic-rich component 16, mixed oil
17. Recovered second polar solvent 18, recovered mixed solvent
19. Third raffinate oil
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As previously mentioned, a first aspect of the invention provides a method of testing a solubility parameter of a mixed hydrocarbon, the method comprising:
(1) the hydrocarbon composition A is set in the mixed hydrocarbon, and the mixed hydrocarbon contains paraffin, single naphthenic hydrocarbon, dicycloalkane, tricycloalkane, alkylbenzene, indane, tetralin, indene, octahydrophenanthrene and CnH2n-10Naphthalene, acenaphthene, CnH2n-14Acenaphthylene, fluorene, CnH2n-16Phenanthrenes, CnH2n-18And at least three of the benzothiophenes as component A1Component A2.mM is a positive integer not less than 3, n is a positive integer not less than 10;
(2) testing the mixed hydrocarbon to be tested as the component A1Component A2.mThe composition of the hydrocarbons and the mass percentage of the corresponding components;
(3) according to the average relative molecular mass M of the mixed hydrocarbon to be detectedMixing ofAnd the types of the components respectively construct the molecular formula of each component, and the constructed molecular formula of each component enables the relative molecular mass of each component and the MMixing ofThe difference between the two is less than or equal to 7, and the relative molecular mass of each component is M1、M2.m；
(4) Respectively constructing a molecular structural formula of each component according to the type and the molecular formula of each component to obtain a model compound of each component, so that the obtained model compound of each component respectively corresponds to each component in the mixed hydrocarbon to be detected, and the model compound optionally further contains saturated alkyl so that the relative molecular mass of the model compound of each component is equal to the relative molecular mass of a substance represented by the molecular formula of each corresponding component;
(5) calculating the solubility parameter of the model compound of each component, which is r1、r2.m；
(6) Calculating the solubility parameter r of the mixed hydrocarbon to be measured according to the formula L1Mixing of，
L1: solubility parameter r of the hydrocarbon mixture to be measuredMixing ofThe solubility parameter of the model compound for each component x the mass percent content of each component.
In step (2) of the present invention, for the mixed hydrocarbon to be measured, for example, when the mixed hydrocarbon to be measured is a petroleum raw material, the composition of a specific substance therein cannot be obtained by the existing instrument method, and it can only be known by the existing technology which types of components are contained in the mixed hydrocarbon to be measured, for example, the components such as paraffin, monocycloparaffin, dicycloalkane, tricycloalkane, alkylbenzene, indane, tetralin, indene, octahydrophenanthrene, C, contained in the mixed hydrocarbon selected by the method of the present inventionnH2n-10Naphthalene, acenaphthene, CnH2n-14Acenaphthylene, fluorene, CnH2n-16Phenanthrenes, CnH2n-18And at least three of the benzothiophenes as component A1Component A2.mM is a positive integer not less than 3, and n is a positive integer not less than 10. In fact, if the hydrocarbon mixture to be tested contains more than 3 components, the method of the present invention can analyze the components according to the above-mentioned sequence names.
Preferably, n is a positive integer of 12 or more; more preferably, n is a positive integer ≧ 14. In particular, n is a positive integer from 14 to 24. And preferably n is a positive integer from 14 to 20.
"according to the average relative molecular mass M of the mixed hydrocarbon to be measuredMixing ofAnd the types of the components respectively construct the molecular formula of each component, and the constructed molecular formula of each component enables the relative molecular mass of each component and the MMixing ofThe difference therebetween being 7 "or less means that since it is known through the step (2) that the mixed hydrocarbon to be measured contains the component A1Component A2.mThat is to say that the type of the individual components in the hydrocarbon mixture to be tested, for example component A, is known by step (2)1Being a monocycloparaffin, component A2Is a bicycloalkane, component A3Is a tricycloalkane, component A4Of the class of alkylbenzenes or the like, then, for example, when the average relative molecular mass M of the mixed hydrocarbons to be tested is knownMixing ofWhen the specific value of (2) is 220, the molecular formula of each component is constructed so that the relative molecular mass of each component and the MMixing ofThe difference therebetween being less than or equal to 7 ″, and according to component A1Being a monocycloparaffin, component A can be identified1Has a molecular formula of C16H32Similar methods can be used to determine the molecular formulas of the remaining components.
An explanation of "the molecular structural formula of each component is respectively constructed according to the kind of each component and the molecular formula of each component to obtain the model compound of each component, so that the obtained model compound of each component corresponds to each component belonging to the mixed hydrocarbon to be measured, and the model compound optionally further contains a saturated alkyl group so that the relative molecular mass of the model compound of each component is equal to the relative molecular mass of a substance represented by the molecular formula of the corresponding component" is given as component a1Being a monocycloparaffin, component A1Has a molecular formula of C16H32For example, component A is known1Is a monocycloparaffin and component A1Has a molecular formula of C16H32Then, component A can be presumed1The model compound of (A) is
Figure BDA0001839719830000081
And the modelC on cycloalkyl in compounds10Substituted alkyl is saturated alkyl. Model compounds for the remaining components can be determined using similar methods. Furthermore, as those skilled in the art know, the model compound is not uniquely defined for a wide variety of components and may have a variety of isomeric structures, and the inventors of the present invention have found that the difference between the solubility parameters of the model compound having a variety of isomeric structures in the method of the present invention is negligible while following the variety of components and the molecular formula of each component.
The average relative molecular mass M of the mixed hydrocarbon to be detectedMixing ofCan be obtained by experimental methods (for example, GB/T17282-2012 method for determining the average relative molecular mass M of petroleum according to viscosity measurements), and preferably the average relative molecular mass M of the mixed hydrocarbon to be tested according to the inventionMixing ofCalculated by the API-87 method and/or the shodhin-forward method.
Preferably, the saturated alkyl group optionally contained in the model compound is a normal saturated alkyl group.
Preferably, the solubility parameters of the model compounds of each component are calculated from molecular dynamics simulations.
Preferably, the software for calculating the solubility parameter of the model compound of each component is Materials Studios, e.g. Materials Studios 6.0, Materials Studios 7.0, Materials Studios 8.0. Firstly, constructing a molecular structure and optimizing; secondly, constructing a periodic system and carrying out pre-balance simulation; then, performing constant temperature dynamics simulation in the system; and finally, calculating cohesive energy density according to the molecular trajectory, and further calculating the solubility parameter of the component. The detailed calculation method can be found in Materials studio user manual.
As previously mentioned, a second aspect of the invention provides a process for processing a heavy diesel fraction, the process comprising:
(1) introducing the heavy diesel oil fraction and a first polar solvent into a first extraction tower for first solvent extraction separation to respectively obtain a first extract and a first raffinate; introducing the first extract into a first solvent recovery tower for first solvent recovery, and obtaining a first aromatic-rich component;
(2) introducing the first raffinate and the second polar solvent into a second extraction tower for second solvent extraction separation to respectively obtain a second extract and a second raffinate; introducing the second extract into a second solvent recovery tower for second solvent recovery, and obtaining a second aromatic-rich component;
the first polar solvent has a stronger polarity than the second polar solvent, and the heavy diesel fraction has a carbon number distribution of 12-25 and a solubility parameter of not less than 20 (J-cm)-3)0.5(ii) a And
controlling the conditions of the first solvent extraction separation so that the solubility parameter of the first raffinate is less than 20 (J-cm)-3)0.5；
Wherein the solubility parameter of the heavy diesel fraction and the solubility parameter of the first raffinate are obtained from the process tests described in the first aspect of the invention.
Preferably, said heavy diesel fraction and said first polar solvent are introduced from the lower and upper parts of said first extraction column, respectively. And the first extract is led out from the bottom of the first extraction tower; the first raffinate is withdrawn from the top of the first extraction column to be introduced thereinto from the lower portion of the second extraction column, the second polar solvent is introduced thereinto from the upper portion of the second extraction column, and a second extract and a second raffinate are withdrawn from the bottom and the top of the second extraction column, respectively.
The method can obtain extract oil rich in aromatic hydrocarbon and raffinate oil with high cetane number.
Preferably, the first polar solvent has a solubility parameter > 25 (J-cm)-3)0.5And the density is more than or equal to 1g/cm3A solvent of (a); more preferably, the first polar solvent is dimethyl sulfoxide and/or sulfolane.
Preferably, the second polar solvent has a solubility parameter of (20-25) (J · cm)-3)0.5And the density is more than or equal to 1g/cm3A solvent of (a); preferably, the second polar solvent is selected from at least one of furfural, N-methylpyrrolidone, and phenol.
Preferably, the weight ratio of the first polar solvent to the heavy diesel fraction used in the first extraction column is (0.3-5): 1, more preferably (0.5-2): 1.
Preferably, the weight ratio of the amount of said second polar solvent and said heavy diesel fraction in said second extraction column is (0.3-5): 1, more preferably (0.5-2): 1.
Preferably, the bottoms temperature of the first extraction column and the second extraction column are each independently in the range of from 30 to 100 ℃, more preferably from 40 to 70 ℃.
Preferably, the overhead temperature of the first extraction column and the second extraction column is each independently in the range of from 40 to 110 ℃, more preferably from 50 to 80 ℃.
According to a preferred embodiment, the process for processing a heavy diesel fraction according to the invention further comprises: mixing the first and second aromatic-rich components to obtain a plant-derived mixed oil.
Preferably, the conditions of the second solvent extraction separation are controlled so that the aromatic hydrocarbon content in the mixed oil obtained by mixing the first aromatic-rich component and the second aromatic-rich component is more than 90 wt%.
According to another preferred embodiment, the process for processing a heavy diesel fraction according to the invention further comprises: and introducing the second raffinate into a third solvent recovery tower for third solvent recovery to obtain third raffinate oil.
Preferably, the conditions of the third solvent recovery are controlled such that the third raffinate is obtained with an alkane content of more than 70 wt.%.
Preferably, the heavy diesel fraction is selected from at least one of straight-run diesel, catalytic cracking diesel and coker diesel.
Preferably, the aromatics content of the heavy diesel fraction is greater than 70 wt.%.
According to a particularly preferred embodiment, the process according to the invention for processing a heavy diesel fraction is carried out using the process scheme shown in FIG. 1, in particular:
(1) introducing the heavy diesel oil fraction 6 and the first polar solvent 7 into a first extraction tower 1 for first solvent extraction separation to respectively obtain a first extract liquid 8 and a first raffinate liquid 9; and introducing the first extract 8 into a first solvent recovery column 3 for first solvent recovery and obtaining a first aromatic-rich component 13 and a recovered first polar solvent 14;
(2) introducing the first raffinate 9 and the second polar solvent 10 into a second extraction tower 2 for second solvent extraction separation to obtain a second extract 11 and a second raffinate 12 respectively; and introducing said second extract 11 into a second solvent recovery column 4 for second solvent recovery and obtaining a second aromatic-rich component 15 and a recovered second polar solvent 17;
(3) mixing the first and second aromatic- rich components 13, 15 to obtain a plant-wide mixed oil 16; and introducing the second raffinate 12 into a third solvent recovery column 5 for third solvent recovery to obtain a third raffinate 19 and a mixed solvent 18;
the first polar solvent 7 has a stronger polarity than the second polar solvent 10, and the heavy diesel fraction 6 has a carbon number distribution of 12-25 and a solubility parameter of not less than 20 (J-cm)-3)0.5(ii) a And
controlling the conditions of the first solvent extraction separation so that the solubility parameter of the first raffinate 9 is less than 20 (J-cm)-3)0.5；
Wherein the solubility parameter of the heavy diesel fraction 6 and the solubility parameter of the first raffinate 9 are obtained from the process tests described in the first aspect of the invention.
In the present invention, the solvent recovery method is well known in the art, and for example, the streams are separately sent to a solvent recovery column to remove the solvent. The settings of the top temperature and the bottom temperature of the solvent recovery column are well known to those skilled in the art and will not be described herein.
The present invention will be described in detail below by way of examples. In the following examples, various raw materials used are commercially available ones unless otherwise specified.
Example 1
The materials shown in table 1 were mixed to form a mixed hydrocarbon.
Calculating the average relative molecular mass M of the mixed hydrocarbon by the API-87 methodMixing ofIs 144.
The hydrocarbon composition and the mass percent of each component in the mixed hydrocarbon are tested by SH/T0606-2005 middle distillate hydrocarbon composition determination method (mass spectrometry) shown in Table 2.
According to the average relative molecular mass M of the mixed hydrocarbonMixing ofAnd the types of the respective components, the molecular formulae of the respective components were constructed as shown in table 2.
The molecular structural formula of each component was constructed according to the kind of each component and the molecular formula of each component, respectively, to obtain model compounds of each component as shown in table 2.
Solubility parameters for the model compounds of each component were calculated from molecular dynamics simulations using Materials Studios 7.0 software, and the results are shown in table 2.
Calculating the solubility parameter r of the mixed hydrocarbon according to the formula L1Mixing of＝18.23。
Meanwhile, the solubility parameter r of the mixed hydrocarbons obtained by calculation in Table 1Mixing and compacting＝18.40。
By comparison, the method provided by the invention has higher accuracy in the method for testing the solubility parameter of the mixed hydrocarbon.
TABLE 1
Figure BDA0001839719830000121
Figure BDA0001839719830000131
TABLE 2
Figure BDA0001839719830000132
Example 2
1. Testing solubility parameter of catalytic cracking diesel A
The properties of the catalytically cracked diesel A are shown in Table 3, and the average relative molecular mass M of the catalytically cracked diesel A is calculated by the API-87 methodMixing ofIs 221.
The hydrocarbon composition and the mass percent of each component in the catalytic cracking diesel oil A are tested by adopting an SH/T0606-2005 middle distillate hydrocarbon composition determination method (mass spectrometry) as shown in the table 3-1.
According to the average relative molecular mass M of the catalytic cracking diesel oil AMixing ofAnd the kinds of the respective components were constructed respectively the molecular formulae of the respective components are shown in Table 3-1.
The molecular structural formula of each component was constructed respectively according to the kind of each component and the molecular formula of each component to obtain model compounds of each component as shown in table 3-1.
Solubility parameters for the model compounds of each component were calculated from molecular dynamics simulations using Materials Studios 7.0 software, and the results are shown in table 3-1.
Calculating the solubility parameter r of the mixed hydrocarbon according to the formula L1Mixing of＝20.32。
2. Processing heavy diesel oil fractions
According to the flow shown in figure 1, catalytic cracking diesel oil A is used as raw material. The raw oil feed rate to the first extraction column was 500 g/hr. The first polar solvent is dimethyl sulfoxide, and the mass ratio of the first polar solvent to the raw oil is 1: 1, the second polar solvent is furfural, and the mass ratio of the second polar solvent to the raw oil is 0.5: 1. the temperature of the top of the two extraction towers is 60 ℃, the temperature of the bottom of the two extraction towers is 40 ℃, and the operating pressure is 0.1 MPa. The solubility parameter of the raffinate from the first extraction column, which was measured in the same manner as in example 1, was 18.91 (J. cm)-3)0.5The first stripper extract and raffinate properties are shown in table 4 and the second stripper extract and raffinate properties are shown in table 5.
Example 3
1. Testing solubility parameter of catalytic cracking diesel B
The properties of the catalytically cracked Diesel B are shown in Table 3, calculated by the API-87 methodAverage relative molecular mass M of catalytically cracked diesel BMixing ofIs 214.
The hydrocarbon composition and the mass percent of each component in the catalytic cracking diesel oil B are tested by adopting an SH/T0606-2005 middle distillate hydrocarbon composition determination method (mass spectrometry) as shown in a table 3-2.
According to the average relative molecular mass M of the catalytic cracking diesel oil BMixing ofAnd the kinds of the respective components were constructed respectively the molecular formulae of the respective components are shown in Table 3-2.
The molecular structural formula of each component was constructed respectively according to the kind of each component and the molecular formula of each component to obtain model compounds of each component as shown in table 3-2.
Solubility parameters for the model compounds of each component were calculated from molecular dynamics simulations using Materials Studios 7.0 software, and the results are shown in table 3-2.
Calculating the solubility parameter r of the mixed hydrocarbon according to the formula L1Mixing of＝20.13。
2. Processing heavy diesel oil fractions
Solvent extraction was carried out in the same extraction apparatus as in example 2, following the scheme of FIG. 1. The catalytic cracking diesel oil B is used as a raw material. The raw oil feed rate to the first extraction column was 500 g/hr. The first polar solvent is dimethyl sulfoxide, and the mass ratio of the first polar solvent to the raw oil is 1.2: 1, the second low-polarity solvent is NMP, and the mass ratio of the second low-polarity solvent to the raw oil is 0.5: 1. the temperature of the top of the two extraction towers is 70 ℃, the temperature of the bottom of the two extraction towers is 50 ℃, and the operating pressure is 0.1 MPa. The solubility parameter of the raffinate from the first extraction column, which was measured in the same manner as in example 1, was 19.12 (J. cm)-3)0.5The first stripper extract and raffinate properties are shown in table 4 and the second stripper extract and raffinate properties are shown in table 5.
Example 4
Solvent extraction was carried out in the same extraction apparatus as in example 2, following the scheme of FIG. 1. The catalytic cracking diesel oil A is used as a raw material. The raw oil feed rate to the first extraction column was 500 g/hr. The first polar solvent is dimethyl sulfoxide, and the mass ratio of the first polar solvent to the raw oil is 0.5: 1, the firstThe polar solvent is furfural, and the mass ratio of the second polar solvent to the raw oil is 1: 1. the temperature of the top of the two extraction towers is 60 ℃, the temperature of the bottom of the two extraction towers is 40 ℃, and the operating pressure is 0.1 MPa. The solubility parameter of the raffinate from the first extraction column, which was measured in the same manner as in example 1, was 19.54 (J. cm)-3)0.5The first stripper extract and raffinate properties are shown in table 4 and the second stripper extract and raffinate properties are shown in table 5.
Comparative example 1
Solvent extraction was carried out in the same extraction apparatus as in example 2, following the scheme of FIG. 1. The catalytic cracking diesel oil A is used as a raw material. The raw oil feed rate to the first extraction column was 500 g/hr. The first polar solvent is furfural, and the mass ratio of the first polar solvent to the raw oil is 0.5: 1, the second polar solvent is furfural, and the mass ratio of the second polar solvent to the raw oil is 1: 1. the temperature of the top of the two extraction towers is 60 ℃, the temperature of the bottom of the two extraction towers is 40 ℃, and the operating pressure is 0.1 MPa.
As a result: the solvent and the raw oil are mutually soluble in each other in the extraction process, and the separation operation cannot be carried out.
Comparative example 2
Solvent extraction was carried out in the same extraction apparatus as in example 2, following the scheme of FIG. 1. The catalytic cracking diesel oil A is used as a raw material. The raw oil feed rate to the first extraction column was 500 g/hr. The first polar solvent is dimethyl sulfoxide, and the mass ratio of the first polar solvent to the raw oil is 0.2: 1, the second polar solvent is furfural, and the mass ratio of the second polar solvent to the raw oil is 0.5: 1. the temperature of the top of the two extraction towers is 60 ℃, the temperature of the bottom of the two extraction towers is 40 ℃, and the operating pressure is 0.1 MPa. The properties of the extract and raffinate after the first extraction are shown in Table 4. The solubility parameter of the raffinate from the first extraction column, which was measured in the same manner as in example 1, was 20.02 (J. cm)-3)0.5When the first-stage raffinate oil is subjected to second-stage extraction, the first-stage raffinate oil and a second-stage solvent furfural are mutually soluble, and separation operation cannot be carried out.
The results show that only the process conditions are controlled so that the raffinate oil solubility parameter of the first extraction column is less than 20(J cm)-3)0.5The raffinate oil can be used in the second extractionThe tower is contacted with a low-polarity solvent to realize separation operation.
Comparative example 3
Solvent extraction was carried out in the same extraction apparatus as in example 2, following the scheme of FIG. 1. The catalytic cracking diesel oil A is used as a raw material. The raw oil feed rate to the first extraction column was 500 g/hr. Referring to the solvent and the process conditions in CN104073285A, the solvent in the first extraction tower is a mixed solvent containing N, N-dimethylformamide and 6 wt% of water, the mass ratio of the mixed solvent to the raw material oil is 0.6:1, and the solvent in the second extraction tower is N, N-dimethylformamide, and the mass ratio of the solvent to the raw material oil is 0.4: 1. The temperature of the top of the two extraction towers is 30 ℃, the temperature of the bottom of the two extraction towers is 30 ℃, and the operating pressure is 0.1 MPa.
As a result: the two phases in the first extraction column cannot be separated into layers, i.e. effective separation operations cannot be carried out in the extraction column.
TABLE 3
Of the diesel type A B
Density (g/cm)3) 0.964 0.956
Paraffin, wt.% 6.5 3.5
Cycloalkane,% by weight 6.3 9.2
Monocyclic aromatic hydrocarbon,% by weight 3.7 6.8
Bicyclic aromatic hydrocarbon, wt.% 48.9 50.1
Aromatic hydrocarbons of more than three rings, wt.% 30.1 27.2
Thiophene (b)% by weight 4.5 3.2
Total aromatic hydrocarbons, wt.% 87.2 87.3
Cetane number 12.8 13.6
Solubility parameter (J. cm)-3)0.5 20.32 20.13
TABLE 3-1
Figure BDA0001839719830000171
Figure BDA0001839719830000181
TABLE 3-2
Figure BDA0001839719830000182
TABLE 4
Figure BDA0001839719830000183
Figure BDA0001839719830000191
TABLE 5
Figure BDA0001839719830000192
Figure BDA0001839719830000201
The results show that the method for processing the heavy diesel oil fraction provided by the invention aims at the heavy diesel oil fraction, has low solvent-oil ratio and high cetane number of raffinate oil, and can be used as a diesel oil blending component; the extracted oil has high aromatic hydrocarbon content and low alkane content, and aromatic hydrocarbon-rich products with high added value can be developed.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.

Claims (13)

1. A method of testing a solubility parameter of a mixed hydrocarbon, the method comprising:
(1) the hydrocarbon composition A is set in the mixed hydrocarbon, and the mixed hydrocarbon contains paraffin, mono-naphthenic hydrocarbon, bi-naphthenic hydrocarbon, tri-naphthenic hydrocarbon,Alkylbenzenes, indanes, tetralins, indenes, octahydrophenanthrenes, CnH2n-10Naphthalene, acenaphthene, CnH2n-14Acenaphthylene, fluorene, CnH2n-16Phenanthrenes, CnH2n-18And at least three of the benzothiophenes as component A1Component A2.mM is a positive integer not less than 3, n is a positive integer not less than 10;
(2) testing the mixed hydrocarbon to be tested as the component A1Component A2.mThe composition of the hydrocarbons and the mass percentage of the corresponding components;
(3) according to the average relative molecular mass M of the mixed hydrocarbon to be detectedMixing ofAnd the types of the components respectively construct the molecular formula of each component, and the constructed molecular formula of each component enables the relative molecular mass of each component and the MMixing ofThe difference between the two is less than or equal to 7, and the relative molecular mass of each component is M1、M2.m；
(4) Respectively constructing a molecular structural formula of each component according to the type and the molecular formula of each component to obtain a model compound of each component, so that the obtained model compound of each component respectively corresponds to each component in the mixed hydrocarbon to be detected, and the model compound optionally further contains saturated alkyl so that the relative molecular mass of the model compound of each component is equal to the relative molecular mass of a substance represented by the molecular formula of each corresponding component;
(5) calculating the solubility parameter of the model compound of each component, which is r1、r2.m；
(6) Calculating the solubility parameter r of the mixed hydrocarbon to be measured according to the formula L1Mixing of，
L1: solubility parameter r of the hydrocarbon mixture to be measuredMixing ofThe solubility parameter of the model compound for each component x the mass percent content of each component.
2. The method of claim 1, wherein the mixture to be tested isAverage relative molecular mass M of hydrocarbonsMixing ofCalculated by the API-87 method and/or the shodhin-forward method.
3. The method according to claim 1 or 2, wherein the saturated alkyl group optionally contained in the model compound is a normal saturated alkyl group.
4. The method of any one of claims 1-3, wherein the solubility parameter of the model compound for each component is calculated from molecular dynamics simulations.
5. The method of claim 4, wherein the software that calculates the solubility parameter of the model compound for each component is Materials Studios.
6. A process for processing a heavy diesel fraction, the process comprising:
(1) introducing the heavy diesel oil fraction and a first polar solvent into a first extraction tower for first solvent extraction separation to respectively obtain a first extract and a first raffinate; introducing the first extract into a first solvent recovery tower for first solvent recovery, and obtaining a first aromatic-rich component;
(2) introducing the first raffinate and the second polar solvent into a second extraction tower for second solvent extraction separation to respectively obtain a second extract and a second raffinate; introducing the second extract into a second solvent recovery tower for second solvent recovery, and obtaining a second aromatic-rich component;
the first polar solvent has a stronger polarity than the second polar solvent, and the heavy diesel fraction has a carbon number distribution of 12-25 and a solubility parameter of not less than 20 (J-cm)-3)0.5(ii) a And
controlling the conditions of the first solvent extraction separation so that the solubility parameter of the first raffinate is less than 20 (J-cm)-3)0.5；
Wherein the solubility parameter of the heavy diesel fraction and the solubility parameter of the first raffinate are obtained from the process test according to any one of claims 1 to 5.
7. The method of claim 6, wherein the first polar solvent is a solubility parameter > 25 (J-cm)-3)0.5And the density is more than or equal to 1g/cm3A solvent of (a);
preferably, the first polar solvent is dimethyl sulfoxide and/or sulfolane.
8. The method of claim 6, wherein the second polar solvent is a solvent with a solubility parameter of (20-25) (J-cm)-3)0.5And the density is more than or equal to 1g/cm3A solvent of (a);
preferably, the second polar solvent is selected from at least one of furfural, N-methylpyrrolidone, and phenol.
9. The process according to any one of claims 6 to 8, wherein the first polar solvent and the heavy diesel fraction are used in a weight ratio in the first extraction column of (0.3-5): 1;
preferably, the weight ratio of the amount of said second polar solvent and said heavy diesel fraction in said second extraction column is (0.3-5): 1.
10. the process of any one of claims 6-8, wherein the bottoms temperatures of the first and second extraction columns are each independently 30-100 ℃;
preferably, the overhead temperature of the first extraction column and the second extraction column is each independently 40 to 110 ℃.
11. The method of any of claims 6-8, wherein the method further comprises: mixing the first and second aromatic-rich components to obtain a plant-derived mixed oil;
preferably, the conditions of the second solvent extractive separation are controlled so that the aromatic content in the mixed oil obtained by mixing the first aromatic-rich component and the second aromatic-rich component is greater than 90 wt%.
12. The method of any of claims 6-8, wherein the method further comprises: introducing the second raffinate into a third solvent recovery tower for third solvent recovery to obtain third raffinate oil;
preferably, the conditions of the third solvent recovery are controlled such that the third raffinate is obtained with an alkane content of more than 70 wt.%.
13. The process of any of claims 6-8, wherein the heavy diesel fraction is selected from at least one of straight-run diesel, catalytic cracked diesel, and coker diesel.
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