CN108997077A - The double solvents and method of separation of extractive distillation aromatic hydrocarbons from hydrocarbon mixture - Google Patents
The double solvents and method of separation of extractive distillation aromatic hydrocarbons from hydrocarbon mixture Download PDFInfo
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- CN108997077A CN108997077A CN201710420938.2A CN201710420938A CN108997077A CN 108997077 A CN108997077 A CN 108997077A CN 201710420938 A CN201710420938 A CN 201710420938A CN 108997077 A CN108997077 A CN 108997077A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
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Abstract
A kind of double solvents of the separation of extractive distillation aromatic hydrocarbons from hydrocarbon mixture, the cosolvent of sulfolane and 20-60 mass % including 40-80 mass %, the cosolvent are the sulfone derivatives with formula (I) structure,In formula (I), R1And R2It is respectively selected from C1~C4Alkyl, naphthenic base or aryl.The double solvents property is stablized, non-corrosive, to aromatic hydrocarbons selectivity with higher, and is easy to regulate and control in use, can reduce the material consumption and energy consumption of extracting rectifying operation.
Description
Technical field
The present invention is a kind of double solvents of aromatics separation from petroleum fluids, specifically, being a kind of smart using extraction
Evaporate double solvents used in separating high-purity aromatic hydrocarbons and its application method from petroleum hydrocarbon raw material.
Background technique
Aromatics separation there are two main classes the technique from the hydrocarbon mixtures such as catalytic reforming gasoline and hydrocracking gasoline.It is a kind of
It is the extracting of liquid liquid, is in the nature liquid-liquid extraction-extracting rectifying combined process, is suitble to aromatics separation in leniently feedstock, institute
The solvent used is glycols solvent, sulfolane etc..Liquid liquid extraction process can obtain high-purity benzene, toluene, two with higher yields
Toluene (BTX) product, but arene content cannot be too high in raw material, and otherwise extraction tower is not easy to operate.Another kind of is extractive distillation
(ED) technique is different and then the aromatics separation from raw material the sides influenced using solvent on hydro carbons each component relative volatility
Method.In contrast, extractive distillation process energy consumption is low, process is simple, is well suited to handle the raw material of high arene content, narrow fraction, institute
Solvent is generally glycols, sulfolane, N-Methyl pyrrolidone, N- formyl-morpholine etc., and obtained product is benzene, or
Benzene and toluene.
Fail to be using the reason of ED technique separating-purifying benzene,toluene,xylene presently used solvent selectivity and
Dissolubility is difficult to take into account.Hydrogenated pyrolysis gasoline C6-C8In fraction, the minimum aromatic hydrocarbons of boiling point is benzene (80.1 DEG C), the highest ring of boiling point
Alkane is ethyl cyclohexane (131.8 DEG C).To realize that benzene is present in tower reactor rich solvent in ED tower, and ethyl cyclohexane is steamed
To tower top, need the interaction of solvent and benzene very strong, and to the non-aromatic of ethyl cyclohexane etc, more repel.And there is height
The solvent of selectivity is often poor to the dissolubility of non-aromatics, on the top of tower, especially solvent feed position and feedstock
Split-phase is easy between position, so as to cause ED tower operating difficulties.
At least one cosolvent is added in high selective solvent to be possible to improve the selectivity of solvent and improve main solvent
Whole efficiency.
CN1430660A discloses a kind of method that aromatic hydrocarbons is purified from petroleum liquid, using sulfolane as main solvent, hydrotropy
Agent is selected from one of 3- methyl sulfolane, -2 pyrrolidones of N- methyl (NMP), acetophenone, isophorone and morpholine, this is answered
Bonding solvent is used for Separation of Benzene/normal heptane system, has obtained the effect better than pure sulfolane.
CN104058916A discloses the morpholine class mixed solvent and its application method of a kind of separation of extractive distillation aromatic hydrocarbons, institute
Stating mixed solvent is N- N-formyl morpholine N and N- acetyl morphine, and separation object is petrobenzene C6-C8Fraction obtains in aromatic hydrocarbon product still
It is more than the solvent of 1mg/L containing concentration, it is subsequent in practical application to still need to denitrogenation processing.
CN1272408C discloses a kind of double solvents of separation of extractive distillation aromatic hydrocarbons, and main solvent is sulfone compound, sweet
Alcohol compound, N- formyl-morpholine or N-Methyl pyrrolidone；Cosolvent is that there are two the hydrocarbon compounds of phenyl ring for tool.It uses
De-pentane oil C is reformed in double solvents separation6-C7Fraction can be produced with the benzene/methylbenzene BTX aromatics for obtaining high-purity in high yield
Product.
Summary of the invention
The double solvents and method of the object of the present invention is to provide a kind of from hydrocarbon mixture separation of extractive distillation aromatic hydrocarbons,
The double solvents property is stablized, non-corrosive, to aromatic hydrocarbons selectivity with higher, and is easy to adjust in use
Control can reduce the material consumption and energy consumption of extracting rectifying operation.
The double solvents of the extracting rectifying aromatic hydrocarbons provided by the invention from hydrocarbon mixture, the ring including 40-80 mass %
The cosolvent of fourth sulfone and 20-60 mass %, the cosolvent are the sulfone derivatives with formula (I) structure,
In formula (I), R1And R2It is respectively selected from C1~C4Alkyl, naphthenic base or aryl.
The method of the present invention is added shown in appropriate formula (I) there are two the conduct of substituent group sulfone derivatives in sulfolane solvent
Cosolvent when aromatic hydrocarbons in the raw material that separation of extractive distillation contains cycloalkane, can effectively reduce solvent ratio, save energy consumption, and
And isolated product is not nitrogenous, sulfur content < 1mg/L, is not necessarily to subsequent refinement treatment.
Detailed description of the invention
Fig. 1 is the flow diagram that the present invention carries out extracting rectifying using double solvents.
Specific embodiment
Double solvents provided by the invention includes that there are two the sulfone classes of substituent group to spread out for main solvent-sulfolane and cosolvent-
Biology, main solvent determine the main character of double solvents, and cosolvent and main solvent act synergistically, and improve selection of the solvent to aromatic hydrocarbons
Property, and increase the dissolubility to non-aromatics, improve gas-liquid mass transfer performance.Double solvents boiling point of the present invention is high, property is steady
Fixed and preferable to dissolution of raw material, on the basis of guaranteeing highly selective, the whole efficiency of extracting rectifying is better than single solvent,
The quality of separating obtained aromatic hydrocarbons can be improved, improve aromatics yield.
Double solvents of the present invention preferably includes the sulfolane of 45-78 mass % and the cosolvent of 22-55 mass %.
The cosolvent is that there are two the sulfone derivatives of substituent group, substituent Rs therein for tool described in formula (I)1And R2
Can be identical, can also be different, it is respectively selected from C1~C4Alkyl, naphthenic base or aryl.The preferred C of the naphthenic base4~C6Cycloalkanes
Base, the preferred phenyl of the aryl.
Preferably, the R in the cosolvent1And R2Difference, R1And R2It is respectively selected from C1~C4Alkyl, the C1~
C4Alkyl can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl group.
R in the cosolvent1And R2Different situations can also be R1Selected from C1~C4Alkyl, R2Selected from hexamethylene
Base or phenyl.
Cosolvent of the present invention can are as follows: Methylethyl sulfone, isopropyl methyl sulfone, ethylisopropyl base sulfone, methyl ring
Amyl sulfone, methyl phenyl sulfone, ethylphenyl sulfone, diphenyl sulfone.
The method of the separation of extractive distillation aromatic hydrocarbons provided by the invention from hydrocarbon mixture, including hydrocarbon mixture is introduced
The middle part of extractive distillation column, double solvents of the present invention introduces the top of extractive distillation column, by extracting rectifying, non-aromatics
It is discharged from tower top, a part returns to extractive distillation column, another part discharge system, the rich solvent rich in aromatic hydrocarbons as overhead reflux
It is discharged into the middle part of solvent recovery tower from extractive distillation column tower bottom, aromatic hydrocarbons is discharged from tower top, and lean solvent returns after tower bottom discharge
Extractive distillation column is recycled.
In the above method, into the double solvents of extractive distillation column and the mass ratio of hydrocarbon mixture raw material, i.e. solvent ratio
It is preferred that 1-20, more preferable 3-10, the number of theoretical plate of extractive distillation column is 30-80, reflux ratio 0.2-5, and double solvents enters tower temperature
Spend preferred 70-90 DEG C, preferred 120-150 DEG C of column bottom temperature, the preferred 0.1-0.3MPa of tower top pressure.
The preferred 5-30 of the theoretical cam curve of the solvent recovery tower, the preferred 0.5-2.0 of reflux ratio, tower top pressure are preferred
0.01-0.05MPa, preferred 155-190 DEG C of column bottom temperature.
Hydrocarbon mixture of the present invention is hydrogenated pyrolysis gasoline C6-C8Fraction, condensate, reformed oil C6-C8It evaporates
Point or coal tar C6Fraction, arene content therein are preferably 20-88 mass %.
Double solvents and extraction rectifying method provided by the invention are especially suitable for from hydrogenated pyrolysis gasoline C6-C8Divide in fraction
From recycling benzene, toluene and dimethylbenzene.
In the present invention, solvent characterizes the selectivity of two components separated with relative volatility (α), is defined as:
α=(Y2/X2)/(Y1/X1) (1)
In formula (1), X1And X2Respectively indicate the mass fraction of component 1 and component 2 in the liquid phase, Y1And Y2Respectively indicate group
Point 1 and the mass fraction in the gas phase of component 2.α value is bigger, shows that Distex process is easier, can be walked with less distillation
Suddenly, less regurgitant volume obtains the higher product of purity.
The present invention is further illustrated with reference to the accompanying drawing.
In Fig. 1, hydrocarbon mixture enters heat exchanger 101 by pipeline 1, enters extractive distillation column 102 after exchanging heat with lean solvent
Middle part, double solvents enters extractive distillation column 102 from top by pipeline 2.The two counter current contacting carries out extracting rectifying, non-aromatics
It being discharged from extracting rectifying column overhead, is condensed into condenser 103, a part is back to extractive distillation column 102 by pipeline 4, remaining
As non-aromatic product by 3 discharger of pipeline.Rich solvent rich in aromatic hydrocarbons by extractive distillation column tower bottom be discharged, through pipeline 5 into
Enter solvent recovery tower 104, after being evaporated under reduced pressure, aromatic hydrocarbons is discharged by tower top, is condensed into condenser 105, and a part is returned by pipeline 6
It is back to solvent recovery tower 104, remaining is produced through pipeline 7 as aromatic hydrocarbon product.Lean solvent is discharged by solvent recovery tower tower bottom, wherein
Sub-fraction regenerating unit is sent to by pipeline 8, remaining is back to extractive distillation column 102 by pipeline 9 and recycles.The extraction
The heating source of rectifying column and solvent recovery tower bottom is reboiler, i.e., rises to one in tower bottom effluent through reboiler heating
After required temperature, it is sent into tower bottom.
The present invention is further illustrated below by example, but the present invention is not limited thereto.
Example 1
This case expedition is the double solvents of cosolvent to aromatic hydrocarbons/non-aromatics separating property using the first and second sulfones.
By the ethyl cyclohexane of the benzene of 90 mass % and 10 mass % mix be used as raw material, add to prepare have different content
The first and second sulfones double solvents in, the mass ratio of double solvents and raw material, i.e. solvent ratio be 3.3.
Entire mixture concussion is shaken up, is warming up to 100 DEG C, stands 30min, is formed with its gas phase of gas chromatographic analysis,
Ethyl cyclohexane is calculated to the relative volatility α of benzene by formula (1), wherein ethyl cyclohexane is component 2, and benzene is component 1, is as a result seen
Table 1.
Table 1
As known from Table 1, not solubilizer when ethyl cyclohexane be only 0.14 to the relative volatility of benzene, be much smaller than 1, this be by
It is 131.8 DEG C in the boiling point of ethyl cyclohexane, is much higher than benzene.Pure sulfolane opposite can will be waved under conditions of solvent ratio is 3.3
Hair degree is improved to 1.426, i.e., available extractive distillation separates the two.The opposite of the double solvents of the first and second sulfones containing 10 mass % is waved
Hair degree is slightly reduced compared with sulfolane, but as the increase of the first and second sulfone contents in double solvents, relative volatility improve, highest can
To 1.565, purer sulfolane improves about 10%.
Example 2
This case expedition is the double solvents of cosolvent to aromatic hydrocarbons/non-aromatics separating property using the first and second sulfones.
By the relative volatility of the method measurement double solvents of example 1, the difference is that the cosolvent in double solvents is first
Base isopropyl sulfone.The ethyl cyclohexane of each solvent calculated by formula (1) is shown in Table 2 to the relative volatility α of benzene.
Table 2
As known from Table 2, isopropyl methyl sulfone is added in sulfolane is cosolvent, can also be effectively improved ethyl cyclohexane pair
The relative volatility α of benzene.
Example 3
This case expedition is the double solvents of cosolvent to aromatic hydrocarbons/non-aromatics separating property using methyl phenyl sulfone.
By the relative volatility of the method measurement double solvents of example 1, the difference is that the cosolvent in double solvents is first
Base phenylsulfone.The ethyl cyclohexane of each solvent calculated by formula (1) is shown in Table 3 to the relative volatility α of benzene.
Table 3
From table 3 it is observed that adding methyl phenyl sulfone in sulfolane is cosolvent, cyclohexyl can also be effectively improved
Relative volatility α of the alkane to benzene.
Comparative example 1
This comparative example investigates published cosolvent to the influence of benzene/ethyl cyclohexane system relative volatility.
By the method for example 1, using the ethyl cyclohexane mixture of the benzene of 90 mass % and 10 mass % as raw material, evaluation is not
When with solvent ratio, different cosolvents and hydrotropy agent content are added in sulfolane to ethyl cyclohexane/benzene relative volatility shadow
It rings, the results are shown in Table 4, wherein NMP is N-Methyl pyrrolidone.
Table 4
As known from Table 4, in Separation of Benzene/ethyl cyclohexane plant process, in sulfolane be added 3- methyl sulfolane or
NMP is cosolvent, solvent ratio under the same conditions, do not make double solvents selectivity be higher than pure sulfolane；And with helping
The increase of solvent adding amount, double solvents selectively decline.
Example 4
With hydrogenated pyrolysis gasoline C6-C8Fraction is raw material, composition be shown in Table 5, by Fig. 1 process separation of extractive distillation wherein
Alkane and aromatic hydrocarbons, contain the first and second sulfones of 50 mass % in the double solvents used, the sulfolane of 50 mass %, extractive distillation column,
The operating condition of solvent recovery tower is shown in Table 6, and separating resulting is shown in Table 7.
Table 5
Table 6
Table 7
| Project | Example 4 | Comparative example 2 |
| BTX aromatics product | ||
| Purity, quality % | 99.90 | 99.65 |
| Yield, quality % | 99.9 | 99.5 |
| Non-aromatics | ||
| Hydrotropy agent content, ppm | 25 | 30 |
| Arene content, quality % | 0.7 | 2.5 |
Comparative example 2
Use the double solvents of the sulfolane of 90 mass % and the 3- methyl sulfolane composition of 10 mass % for extracting rectifying
Solvent, by 4 method abstraction distillation separation cracking hydrogasoline C of example6-C8Aromatic hydrocarbons and non-aromatics in fraction, extractive distillation column,
The operating condition of solvent recovery tower is shown in Table 6, the results are shown in Table 7.
The result shows that double solvents of the double solvents of the present invention compared with comparative example 2, small and other in sweetening agent
In the case that operating condition is essentially identical, separating obtained BTX aromatics product purity, yield are higher.
Claims (11)
1. a kind of double solvents of the separation of extractive distillation aromatic hydrocarbons from hydrocarbon mixture, sulfolane including 40-80 mass % and
The cosolvent of 20-60 mass %, the cosolvent are the sulfone derivatives with formula (I) structure,
In formula (I), R1And R2It is respectively selected from C1~C4Alkyl, naphthenic base or aryl.
2. double solvents described in accordance with the claim 1, it is characterised in that the double solvents includes the ring of 45-78 mass %
The cosolvent of fourth sulfone and 22-55 mass %.
3. double solvents according to claim 1 or 2, it is characterised in that the naphthenic base is C4~C6Naphthenic base, institute
The aryl stated is phenyl.
4. double solvents according to claim 1 or 2, it is characterised in that the R in the cosolvent1And R2Difference, R1With
R2It is respectively selected from C1~C4Alkyl.
5. double solvents according to claim 1 or 2, it is characterised in that the R in the cosolvent1And R2Difference, R1Choosing
From C1~C4Alkyl, R2Selected from cyclohexyl or phenyl.
6. double solvents according to claim 1 or 2, it is characterised in that the hydrocarbon mixture is hydrogenated pyrolysis gasoline
C6-C8Fraction, condensate, reformed oil C6-C8Fraction or coal tar C6Fraction.
7. a kind of method of the separation of extractive distillation aromatic hydrocarbons from hydrocarbon mixture, including hydrocarbon mixture is introduced into extractive distillation column
Middle part, double solvents described in claim 1 introduces the top of extractive distillation column, and by extracting rectifying, non-aromatics is from tower top
Discharge, a part return to extractive distillation column as overhead reflux, and another part discharge system, the rich solvent rich in aromatic hydrocarbons is from extraction
Rectifying tower bottom is discharged into the middle part of solvent recovery tower, and aromatic hydrocarbons is discharged from tower top, and lean solvent returns to extraction essence after tower bottom discharge
Evaporate tower recycling.
8. according to the method for claim 7, it is characterised in that into the double solvents and hydrocarbon mixture of extractive distillation column
The mass ratio of raw material is 1-20, and the number of theoretical plate of extractive distillation column is 30-80, reflux ratio 0.2-5, and double solvents enters tower temperature degree
It is 70-90 DEG C, column bottom temperature is 120-150 DEG C, tower top pressure 0.1-0.3MPa.
9. according to the method for claim 7, it is characterised in that the theoretical cam curve of solvent recovery tower is 20-50, reflux ratio
For 0.5-2.0, tower top pressure 0.01-0.05MPa, column bottom temperature is 155-190 DEG C.
10. according to the method for claim 7, it is characterised in that the hydrocarbon mixture is hydrogenated pyrolysis gasoline C6-C8It evaporates
Divide, condensate, reformed oil C6-C8Fraction or coal tar C6Fraction.
11. according to the method for claim 7, it is characterised in that arene content is 20-88 mass % in hydrocarbon mixture.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2033942A (en) * | 1933-06-28 | 1936-03-17 | Atlantic Refining Co | Hydrocarbon oil treatment |
| US2831039A (en) * | 1955-04-04 | 1958-04-15 | Standard Oil Co | Solvent extraction |
| US3146190A (en) * | 1961-05-08 | 1964-08-25 | Shell Oil Co | Recovery of aromatics |
| US3466346A (en) * | 1967-05-29 | 1969-09-09 | Universal Oil Prod Co | Method for aromatic hydrocarbon recovery |
| US4053369A (en) * | 1974-05-30 | 1977-10-11 | Phillips Petroleum Company | Extractive distillation |
| US4401517A (en) * | 1981-11-20 | 1983-08-30 | Phillips Petroleum Company | Vapor-liquid extractive distillation with dialkyl sulfone/water combination |
| WO2002064530A1 (en) * | 2001-02-14 | 2002-08-22 | Gaylord Chemical Corporation | Sulfone-sulfoxide compositions for enhance aromatic extraction |
| CN101649221A (en) * | 2008-08-13 | 2010-02-17 | 中国石油天然气股份有限公司 | Method for producing reforming raw material from gasoline light and medium fractions |
| CN105542834A (en) * | 2014-10-30 | 2016-05-04 | 中国石化扬子石油化工有限公司 | Composite solvent for extraction distillation separation of aromatic hydrocarbons, and applications thereof |
-
2017
- 2017-06-07 CN CN201710420938.2A patent/CN108997077B/en active Active
Patent Citations (9)
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|---|---|---|---|---|
| US2033942A (en) * | 1933-06-28 | 1936-03-17 | Atlantic Refining Co | Hydrocarbon oil treatment |
| US2831039A (en) * | 1955-04-04 | 1958-04-15 | Standard Oil Co | Solvent extraction |
| US3146190A (en) * | 1961-05-08 | 1964-08-25 | Shell Oil Co | Recovery of aromatics |
| US3466346A (en) * | 1967-05-29 | 1969-09-09 | Universal Oil Prod Co | Method for aromatic hydrocarbon recovery |
| US4053369A (en) * | 1974-05-30 | 1977-10-11 | Phillips Petroleum Company | Extractive distillation |
| US4401517A (en) * | 1981-11-20 | 1983-08-30 | Phillips Petroleum Company | Vapor-liquid extractive distillation with dialkyl sulfone/water combination |
| WO2002064530A1 (en) * | 2001-02-14 | 2002-08-22 | Gaylord Chemical Corporation | Sulfone-sulfoxide compositions for enhance aromatic extraction |
| CN101649221A (en) * | 2008-08-13 | 2010-02-17 | 中国石油天然气股份有限公司 | Method for producing reforming raw material from gasoline light and medium fractions |
| CN105542834A (en) * | 2014-10-30 | 2016-05-04 | 中国石化扬子石油化工有限公司 | Composite solvent for extraction distillation separation of aromatic hydrocarbons, and applications thereof |
Non-Patent Citations (1)
| Title |
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| LEE, FU MING: "《Use of organic sulfones as the extractive distillation solvent for aromatics recovery》", 《INDUSTRIAL & ENGINEERING CHEMISTRY PROCESS DESIGN AND DEVELOPMENT》 * |
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