CN114736092B - Process for separating olefins from mixtures of alkanes and olefins - Google Patents

Process for separating olefins from mixtures of alkanes and olefins Download PDF

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CN114736092B
CN114736092B CN202110028156.0A CN202110028156A CN114736092B CN 114736092 B CN114736092 B CN 114736092B CN 202110028156 A CN202110028156 A CN 202110028156A CN 114736092 B CN114736092 B CN 114736092B
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alkene
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CN114736092A (en
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赵效洪
朱豫飞
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China Energy Investment Corp Ltd
National Institute of Clean and Low Carbon Energy
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China Energy Investment Corp Ltd
National Institute of Clean and Low Carbon Energy
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/005—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/40—Ethylene production

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Abstract

The invention relates to the field of separation of alkane and alkene, and discloses a method for separating alkene from a mixture of alkane and alkene, which comprises the following steps of (1) carrying out first mixing on the mixture containing alkane and alkene and an extracting agent, and then extracting, separating to obtain an extraction phase A containing the extracting agent, alkene and a small part of alkane, and a raffinate phase a containing most of alkane; (2) Layering after carrying out second mixing on the extraction phase A and the alkane separating agent, and separating to obtain a lower mixed solution B containing alkene, the extracting agent and the alkane separating agent and an upper mixed solution B containing alkane; (3) Rectifying the extract phase B, and separating to obtain an olefin product. The method for separating the olefin from the mixture of the alkane and the olefin provided by the invention has the advantages of no need of heating, low energy consumption and simple flow, and the mixture containing the alkane and the olefin can be separated by using the extractant and the alkane separating agent, so that the olefin product with the purity of more than 99% can be obtained.

Description

Process for separating olefins from mixtures of alkanes and olefins
Technical Field
The invention relates to the technical field of separation of alkane and alkene, in particular to a method for separating alkene from a mixture of alkane and alkene.
Background
The product of coal-based Fischer-Tropsch oil generally has an alpha olefin content of between 50 and 70wt%, and in addition, contains a plurality of alkanes having the same carbon number as the olefins. The alpha-olefin in the coal-based synthetic oil is more specific, and contains odd-carbon olefin which cannot be produced in petrochemical industry, and the olefin can be used as a high-quality comonomer, so that the alpha-olefin is more likely to provide infinite possibility for polymerizing new performance products downstream. If the alpha-olefin can be separated, the economic benefit of the coal-based synthetic oil can be improved, the performance of downstream products can be greatly improved, and the continuous healthy development of the coal chemical industry in China can be promoted.
However, since the difference in boiling points between the olefin and the alkane is small, it is difficult to achieve thorough separation of the alkane and the olefin by rectification or extraction, especially separation of the alkane and the alkene having similar or identical carbon numbers.
At present, traditional extraction, rectification or extractive rectification processes are mainly adopted for separating olefin and alkane. However, because the difference of boiling points of the alkene and the alkane with similar or same carbon number is very small, the traditional extraction is adopted, the separation of the alkene and the alkane is not thorough, the cost of the separation by adopting a rectification process and an extraction rectification process is very high, the solvent consumption is large, the recovery is difficult, and the requirement of the current social development is not met. Although current technology is also capable of separating olefins and paraffins, there remains a need to explore more efficient, energy-efficient separation methods.
A simple extraction process that allows separation of alkane olefins is described in CN103232313 a. The method adopts a single-component polar extractant such as N-methyl pyrrolidone (NMP), N-formyl morpholine (NFM) and 1-methylimidazole (1-MI), and the mixture of the alkane with the same carbon number and the alkene to be separated is fully contacted and mixed, then the mixture is stood for layering and separation is carried out. However, complete separation of the same carbon number alkane and alkene is not achieved in this process.
Accordingly, there is a need to provide a process for separating olefins from a mixture of alkanes and olefins that is simple to operate, low in energy consumption and high in separation efficiency.
Disclosure of Invention
The invention aims to solve the problems of high energy consumption or incomplete separation of alkane and alkene in the prior art, and provides a method for separating alkene from a mixture of alkane and alkene.
In order to achieve the above object, the present invention provides a process for separating an olefin from a mixture of an alkane and an olefin, the process comprising the steps of:
(1) Carrying out first mixing on a mixture containing alkane and alkene and an extracting agent, and then extracting, and separating to obtain an extraction phase A containing the extracting agent, alkene and a small part of alkane and a raffinate phase a containing a large part of alkane;
(2) Layering after carrying out second mixing on the extraction phase A and the alkane separating agent, and separating to obtain a lower mixed solution B containing alkene, the extracting agent and the alkane separating agent and an upper mixed solution B containing alkane;
(3) Rectifying the extract phase B, and separating to obtain an olefin product.
Through the technical scheme, the beneficial technical effects obtained by the invention are as follows:
1) The method for separating the olefin from the mixture of the alkane and the olefin, provided by the invention, has the advantages of no need of heating, low energy consumption and simple flow, and can obtain the olefin with the purity of more than 99% by separating the mixture containing the alkane and the olefin by using the extractant and the alkane separating agent;
2) According to the method for separating the olefin from the mixture of the alkane and the olefin, the used extracting agent and the used alkane separating agent can be recycled, so that the production cost is saved, and the method is suitable for industrial popularization;
3) The method for separating the olefin from the mixture of the alkane and the olefin provided by the invention can separate the alkane and the olefin in the mixture containing a plurality of alkanes and the olefin with the same carbon number in a wide-distillation section at one time to obtain a high-purity mixed olefin product, and can separate the mixture containing the alkane and the olefin with the same carbon number to obtain the high-purity olefin, thereby having wide application range.
Detailed Description
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
The present invention provides a process for separating olefins from a mixture of alkanes and olefins, the process comprising the steps of:
(1) Carrying out first mixing on a mixture containing alkane and alkene and an extracting agent, and then extracting, and separating to obtain an extraction phase A containing the extracting agent, alkene and a small part of alkane and a raffinate phase a containing a large part of alkane;
(2) Layering after carrying out second mixing on the extraction phase A and the alkane separating agent, and separating to obtain a lower mixed solution B containing alkene, the extracting agent and the alkane separating agent and an upper mixed solution B containing alkane;
(3) And rectifying the lower mixed solution B, and separating to obtain an olefin product.
In step (1):
in a preferred embodiment, the mixture comprising alkanes and alkenes is a mixture comprising a plurality of alkanes and alkenes of the same carbon number or a mixture comprising one alkane and alkene of the same carbon number.
The carbon number of the alkane and the alkene is not particularly limited, and may be C5-C12, preferably C5-C10. The structure of the alkane is not particularly limited in the present invention, and may be a linear alkane, or may be a branched or cyclic alkane, preferably a linear alkane. The structure of the olefin is not particularly limited in the present invention, and may be an alpha-olefin, or an internal olefin, preferably an alpha-olefin.
The invention can separate a plurality of alkanes and alkenes with the same carbon number in the wide-distillation section at one time to obtain a high-purity mixed alkene product. For example, the naphtha of the complex alkane-alkene mixture is separated to obtain high-purity mixed alkene, and then the obtained high-purity mixed alkene is further separated to obtain alkene products with various carbon numbers, such as products of pentene, hexene, heptene, octene, nonene, decene and the like, and also can obtain alkene combinations, such as pentene+hexene and the like according to actual production requirements. But also can separate the mixture containing alkane and alkene with the same carbon number to obtain alkene with high purity, for example, 1-hexene/n-hexane can be separated to obtain 1-hexene with high purity; 1-heptene/n-heptane can be isolated to give 1-heptene of high purity.
In a preferred embodiment, the mixture comprising alkanes and alkenes is a mixture comprising one alkane and alkene of the same carbon number, preferably a mixture comprising one alkane and a-alkene of the same carbon number, further preferably a mixture of one alkane and a-alkene of the same carbon number between 5 and 12, e.g. 5 and 10, more preferably a mixture of 1-hexene and n-hexane.
In a preferred embodiment, the invention is not particularly limited in terms of the source of the mixture of alkane and alkene, and is preferably Fischer-Tropsch light oil from which oxygenates have been removed with or without deoxygenation in the coal chemical industry.
In a preferred embodiment, the extractant is a weak polar solvent or a complex extractant, wherein the complex extractant comprises the weak polar solvent and a strong polar solvent;
in a preferred embodiment, the weak polar solvent is selected from at least one of gamma-butyrolactone, N-methylpyrrolidone, N-dimethylformamide, N-formylmorpholine, morpholine, dimethylsulfoxide, acetonitrile; preferably at least one selected from the group consisting of gamma-butyrolactone, N-methylpyrrolidone, N-dimethylformamide, N-formylmorpholine and dimethylsulfoxide; the strongly polar solvent is selected from alcohols and/or water, preferably water.
In a preferred embodiment, the alcohol may be selected from monohydric or polyhydric alcohols, preferably monohydric alcohols, further preferably monohydric alcohols of C1-C4, preferably monohydric alcohols of C2-C3, such as ethanol.
In order to further improve the extraction separation efficiency of alkanes and alkenes, in a preferred embodiment, the extractant is preferably a complex extractant of the weak polar solvent and the strong polar solvent; wherein the mass ratio of the weak polar solvent to the strong polar solvent is 10-1000:1, preferably 5-100:1, and more preferably 8-30:1.
In a further preferred embodiment, the built extractant is selected from at least one of gamma-butyrolactone+water, N-methylpyrrolidone+water, N-dimethylformamide+water, N-formylmorpholine+water, dimethylsulfoxide+water.
In a preferred embodiment, the separation coefficient of the olefin in the extractant is β > 1.3, preferably β > 1.5, more preferably β > 1.9, at 25 ℃.
Wherein the separation coefficient β= (olefin content in the extract phase/alkane content in the extract phase)/(olefin content in the raffinate phase/alkane content in the raffinate phase).
In a preferred embodiment, the mass ratio of extractant to the mixture comprising alkane and alkene is in the range of 0.1 to 15:1, preferably in the range of 0.5 to 5:1, and more preferably in the range of 1 to 2.5:1.
In a preferred embodiment, the first mixing mode of the extractant and the mixture comprising alkane and alkene is not particularly limited, and the first mixing mode can be performed by means of gravity buoyancy difference at room temperature, and can also be performed by means of mechanical assistance such as vibration, stirring, shaking and the like. The invention does not limit the mixing time of extraction, and the specific mixing time can be adjusted according to the mixing mode and the treatment capacity.
In a preferred embodiment, in step (1), the extraction is carried out at room temperature, the extraction temperature may be from 5 to 40 ℃, preferably from 10 to 30 ℃. The extraction time is not particularly limited, and the specific extraction time can be adjusted according to the treatment capacity.
In a preferred embodiment, after the extraction is completed, an extract phase a is obtained containing the extractant, the alkene and a small portion of the alkane, and a raffinate phase a containing a large portion of the alkane. Wherein, the content of the extractant in the extract phase A is 81 to 93wt percent, preferably 83 to 89wt percent based on 100 percent of the total amount of the extract phase A; the olefin content is 6-14wt%, preferably 9-12.5wt%; the alkane content is 1-5wt%, preferably 2-4.5wt%.
In the step (2):
in a preferred embodiment, the alkane separating agent is an alkene or a mixture of alkenes, preferably the same alkene as the alkene to be separated.
In the present invention, the olefin to be separated refers to an olefin in a mixture comprising an alkane and an olefin. The inventor has found through research and creativity that: the extraction phase A is a homogeneous mixed solution of extractant-alkene-alkane, because the polarity of the extractant and the alkene is large and the polarity of the alkane is small, after the alkane separating agent with large polarity is added into the extraction phase A, the original polarity balance in the extraction phase A can be broken, so that the newly added alkane separating agent gradually replaces alkane to enter the extraction phase A to form a homogeneous solution of the extractant-alkene-alkane separating agent, and the alkane with smaller polarity is separated from the homogeneous mixed solution of the extractant-alkene-alkane and enters the upper layer of the homogeneous solution of the extractant-alkene-alkane separating agent, so that the mixed solution is split in phase, and the alkane can be separated from the extraction phase A.
In order to reduce the difficulty of the subsequent separation operation of the extractant-alkene-alkane separating agent, which is preferably the same as the alkene to be separated, the separation process is simplified. When the olefin to be separated in the mixture containing the alkane and the olefin includes a plurality of olefins, the alkane separating agent is at least one of the plurality of olefins to be separated, and may be a single olefin or may be a mixture of the plurality of olefins. When the alkane separating agent is a mixture of a plurality of olefins, the specific mixing proportion of the plurality of olefins in the mixture is not particularly required. For example, when separating a mixture of 1-heptene, 1-hexene/n-heptane, n-hexane, the alkane separating agent may be 1-hexene, 1-heptene or a mixture of 1-hexene and 1-heptene in any ratio.
In a preferred embodiment, the mass ratio of the alkane separating agent to the extraction phase a is 0.01-15:1, preferably 0.02-5:1, further preferably 0.05-0.5:1, more preferably 0.06-0.15:1.
In a preferred embodiment, the second mixing mode of the alkane separating agent and the extraction phase A is not particularly limited, and the alkane separating agent and the extraction phase A can be mixed by means of gravity buoyancy difference or by means of mechanical assistance such as vibration, stirring, shaking and the like. The invention does not limit the mixing time of the alkane separating agent and the extraction phase A, and the specific mixing time can be adjusted according to the mixing mode and the treatment capacity.
In a preferred embodiment, the layering is performed at room temperature, wherein the room temperature is not particularly limited in the present invention, and may be 5 to 40 ℃, preferably 10 to 30 ℃.
In a preferred embodiment, the layering includes standing and pipetting. The invention does not limit the standing time, and the specific standing time can be adjusted according to the treatment capacity.
In a preferred embodiment, after the standing is finished, a liquid separation operation is performed to obtain a lower mixed liquid B containing olefin, an extractant and an alkane separating agent and an upper mixed liquid B containing alkane;
in a preferred embodiment, step (2) further comprises repeating the layering operation for the resulting lower mixed liquor B until the mass content of alkane in the resulting lower mixed liquor B is 0.15% or less, preferably 0.07% or less.
Wherein, the alkane in the extraction phase A can be basically completely removed after repeated operation for a plurality of times, and the lower mixed solution B which almost contains no alkane is obtained.
In the step (3):
the rectification operation conditions in the step (3) are not particularly limited, and the rectification operation is performed according to the prior art, and normal pressure rectification can be preferred. Wherein, the normal pressure in the invention refers to 0.1MPa.
Since the alkane separating agent is also an alkene, in the present invention, the alkene product separated in step (3) includes not only the alkene to be separated, which is separated from the mixture comprising alkane and alkene, but also the added alkane separating agent. When the alkane separating agent is preferably the same as the alkene to be separated in the mixture comprising alkane and alkene, the lower mixed liquid B is subjected to a rectification operation, and high-purity alkene and extracting agent can be obtained. Wherein, the high-purity olefin product obtained by rectification at this time comprises not only the olefin to be separated, but also the added alkane separating agent. The obtained extractant can be recycled, so that the production cost can be saved, and the method is suitable for industrialized popularization. When the alkane separating agent is olefin different from the olefin to be separated, the lower mixed liquid B is subjected to rectification operation, and the obtained olefin product can be the olefin product to be separated and the independent alkane separating agent. Wherein, the obtained extractant and alkane separating agent can be recycled.
In a preferred embodiment, the purity of the separated olefin is above 99wt%, preferably above 99.7 wt%.
In a preferred embodiment, the purity of the separated extractant is 99wt%, preferably above 99.5 wt%.
In a preferred embodiment, the operations of step (1) and step (2) may be repeated a plurality of times in order to further increase the amount of olefin separated from the mixture comprising alkane and olefin.
The present invention will be described in detail by examples.
Example 1
(1) 30g of a mixture with a 1-hexene content of 70wt% and a n-hexane content of 30wt% are fully mixed and contacted with 40g of a compound extractant C1 of gamma-butyrolactone and water (the gamma-butyrolactone content is 90 wt%) for extraction: vibrating for 1min at 20 ℃, then standing for 15min, and then separating liquid to obtain an extraction phase; wherein the obtained extract phase has a 1-hexene content of 11.5wt%, a n-hexane content of 2.5wt%, a gamma-butyrolactone content of 77.5wt% and a water content of 8.5wt%.
(2) Thoroughly mixing 45g of the extract phase separated from the step (1) with 5g of alkane separating agent 1-hexene for contact, and layering: vibrating for 2min at 20 ℃, then standing for 10min, and then separating to obtain a lower mixed solution; the layering operation was repeated three times on the obtained lower mixed solution, wherein the composition and content of the lower mixed solution obtained after each layering are shown in table 1:
table 1:
(3) Rectifying the lower mixed solution obtained by separating the third liquid separating operation in the step (2), wherein the purity of the obtained 1-hexene is 99.8wt% and the purity of the obtained extractant is 99.8wt% at the distillation temperature of 62-65 ℃.
Example 2
(1) 30g of a mixture with the 1-hexene content of 70wt% and the n-hexane content of 30wt% are fully mixed and contacted with 45g of a compound extractant C2 of dimethyl sulfoxide and water (the dimethyl sulfoxide content is 95 wt%) for extraction: vibrating at 20deg.C for 2min, standing for 10min, and separating to obtain extract phase; the obtained extract phase has a 1-hexene content of 12.1wt%, a n-hexane content of 2.3wt%, a dimethyl sulfoxide content of 81.3wt%, and a water content of 4.3wt%; .
(2) 50g of the extract phase obtained by separation in the step (1) is fully mixed and contacted with 6g of alkane separating agent 1-hexene, and layering is carried out: vibrating for 2min at 20 ℃, then standing for 10min, and then separating to obtain a lower mixed solution; repeating layering operation for three times on the obtained lower mixed solution, wherein the composition and the content of the lower mixed solution obtained after each layering are shown in table 2;
table 2:
(3) Rectifying the lower mixed solution obtained by separating the third liquid separating operation in the step (2), wherein the purity of the obtained 1-hexene is 99.8wt% and the purity of the obtained extractant is 99.6wt% at the distillation temperature of 62-65 ℃.
Example 3
(1) 20g of a mixture with the 1-hexene content of 70wt% and the N-hexane content of 30wt% is fully mixed and contacted with 40g of a compound extractant C3 of N-methylpyrrolidone and water (the N-methylpyrrolidone content is 93 wt%) for extraction: vibrating for 1min at 20 ℃, then standing for 10min, and then separating liquid to obtain an extraction phase; wherein the obtained extract phase had a 1-hexene content of 9.0wt%, an N-hexane content of 4.2wt%, an N-methylpyrrolidone content of 83.3wt% and a water content of 3.5%.
(2) Thoroughly mixing and contacting 44g of the extract phase obtained in the step (1) with 5g of alkane separating agent 1-hexene, and layering: vibrating for 2min at 20 ℃, then standing for 10min, and then separating to obtain a lower mixed solution; repeating layering operation for three times on the obtained lower mixed solution, wherein the composition and the content of the lower mixed solution obtained after each layering are shown in table 3;
table 3:
(3) Rectifying the lower mixed solution obtained by separating the third liquid separating operation in the step (2), wherein the purity of the obtained 1-hexene is 99.7wt% and the purity of the obtained extractant is 99.6wt% at the distillation temperature of 62-65 ℃.
Example 4
(1) 100g of the mixture with the composition shown in Table 4 is fully mixed and contacted with 120g N-formylmorpholine and water compound extractant C4 (the content of N-formylmorpholine is 95 wt%) for extraction: vibrating for 1min at 20 ℃, then standing for 15min, and then separating liquid to obtain an extraction phase; the composition and content of the obtained extract phase are shown in Table 5.
TABLE 4 Table 4
Component/wt% C5 C6 C7 C8 C9 C10
N-alkanes 4.86 5.45 4.65 4.85 4.99 0.96
N-olefins 12.28 13.80 13.56 14.64 15.04 4.92.
TABLE 5
(2) 136g of the extract phase obtained by separation in the step (1) is fully mixed and contacted with 10g of alkane separating agent 1-hexene, and layering is carried out: vibrating at 20deg.C for 2min, standing for 10min, and separating to obtain lower layer mixed solution; repeating layering operation for three times on the obtained lower mixed solution, wherein the composition and the content of the lower mixed solution obtained after each layering are shown in table 6;
table 6:
(3) And (3) rectifying the lower mixed solution obtained by separating the third liquid separating operation in the step (2), wherein the purity of the obtained normal olefin reaches more than 99wt% at the distillation temperature of 62-172 ℃.
Example 5
(1) 60g of a mixture with a 1-hexene content of 70wt% and a n-hexane content of 30wt% are fully mixed and contacted with a 35g N-formylmorpholine extractant C5 for extraction: vibrating for 1min at 20 ℃, then standing for 15min, and then separating liquid to obtain an extraction phase; wherein the obtained extract phase has a 1-hexene content of 10.5 wt.%, an N-hexane content of 3.5 wt.% and an N-formylmorpholine content of 86 wt.%.
(2) Thoroughly mixing 40g of the extract phase separated from the step (1) with 4g of alkane separating agent 1-hexene for contact, and layering: vibrating for 2min at 20 ℃, then standing for 10min, and then separating to obtain a lower mixed solution; the layering operation was repeated three times on the obtained lower mixed solution, wherein the composition and content of the lower mixed solution obtained after each layering are shown in table 1:
table 7:
(3) Rectifying the lower mixed solution obtained by separating the third liquid separating operation in the step (2), wherein the purity of the obtained 1-hexene is 99.8wt% and the purity of the obtained extractant is 99.6wt% at the distillation temperature of 62-65 ℃.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.

Claims (15)

1. A process for separating an olefin from a mixture of an alkane and an olefin, the process comprising the steps of:
(1) Carrying out first mixing on a mixture containing alkane and alkene and an extracting agent, and then extracting, and separating to obtain an extraction phase A containing the extracting agent, alkene and a small part of alkane and a raffinate phase a containing a large part of alkane;
(2) Layering after carrying out second mixing contact on the extraction phase A and an alkane separating agent, and separating to obtain a lower mixed solution B containing alkene, the extracting agent and the alkane separating agent and an upper mixed solution B containing alkane;
(3) Rectifying the lower mixed liquid B, and separating to obtain an olefin product;
wherein the mixture containing alkane and alkene is a mixture containing alkane and alkene with the same carbon number and the carbon number is C5-C10;
the extractant is a weak polar solvent or a compound extractant, the compound extractant comprises the weak polar solvent and a strong polar solvent, and the weak polar solvent is at least one selected from gamma-butyrolactone, N-methylpyrrolidone, N-dimethylformamide, N-formylmorpholine, morpholine and dimethyl sulfoxide; the strong polar solvent is water;
wherein the alkane separating agent is the same as the alkene to be separated.
2. The separation process according to claim 1, wherein in step (1), the mixture comprising alkane and alkene is a mixture of 1-hexene and n-hexane.
3. The separation method according to claim 1 or 2, wherein the weak polar solvent is selected from at least one of γ -butyrolactone, N-methylpyrrolidone, N-dimethylformamide, N-formylmorpholine and dimethylsulfoxide.
4. The separation method according to claim 1, wherein in the complex extractant of the weak polar solvent and the strong polar solvent, the mass ratio of the weak polar solvent to the strong polar solvent is 10-1000:1.
5. The separation method according to claim 4, wherein the mass ratio of the weakly polar solvent to the strongly polar solvent is 50-100:1.
6. The separation method according to claim 5, wherein the mass ratio of the weakly polar solvent to the strongly polar solvent is 8-30:1.
7. The separation process according to claim 1, wherein the mass ratio of the extractant to the mixture comprising alkanes and alkenes is 0.1-15:1;
and/or, the extraction is performed at room temperature.
8. The separation process of claim 7, wherein the mass ratio of extractant to the mixture comprising alkanes and alkenes is 0.5-5:1.
9. The separation method according to claim 7, wherein the extraction phase A has an extractant content of 81 to 93wt%, an olefin content of 6 to 14wt% and an alkane content of 1 to 5wt%.
10. The separation process according to claim 9, wherein the extraction phase a has an extractant content of 83-89wt%, an olefin content of 9-12.5wt% and an alkane content of 2-4.5wt%.
11. The separation process according to claim 1, wherein the mass ratio of the alkane separating agent to the extraction phase a is 0.01-15:1;
and/or, the delamination is performed at room temperature.
12. The separation process according to claim 11, wherein the mass ratio of the alkane separating agent to the extraction phase a is 0.06-0.15:1.
13. The separation method according to claim 11, wherein step (2) further comprises repeating the layering operation on the obtained lower mixed liquid B until the mass content of alkane in the obtained lower mixed liquid B is 0.15% or less.
14. The separation method according to claim 13, wherein step (2) further comprises repeating the layering operation on the obtained lower mixed liquid B until the mass content of alkane in the obtained lower mixed liquid B is 0.07% or less.
15. The separation method according to claim 1, wherein in step (3), the rectification is atmospheric rectification.
CN202110028156.0A 2021-01-07 2021-01-07 Process for separating olefins from mixtures of alkanes and olefins Active CN114736092B (en)

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US4132744A (en) * 1977-12-12 1979-01-02 Texaco Inc. Process for separating liquid olefin-paraffin mixtures
US4267034A (en) * 1979-11-14 1981-05-12 Phillips Petroleum Company Separating olefins from paraffins with dimethyl sulfoxide extractant
US5068011A (en) * 1990-10-26 1991-11-26 Phillips Petroleum Company Separation of monoolefins from paraffins
RU2379277C1 (en) * 2008-06-30 2010-01-20 Олег Станиславович Павлов Method of separating alkane and alkene fractions
CN103232313A (en) * 2013-05-06 2013-08-07 北京化工大学 Extraction and separation method of alkane/olefin
CN103864554A (en) * 2014-04-09 2014-06-18 天津市昊永化工科技有限公司 Method for extracting, rectifying and separating alkane, olefin and arene from hydrocarbon mixture
CN106966852A (en) * 2016-01-14 2017-07-21 天津大学 The method that continuous extraction rectifying separates high-carbon n-alkane and normal olefine
CN108929188A (en) * 2017-05-23 2018-12-04 中国石油化工股份有限公司 From mixing C4The method of separation of extractive distillation butane and butylene in hydrocarbon raw material
EP3428142A1 (en) * 2017-07-14 2019-01-16 Basf Se Process for separating paraffins and olefins

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB881597A (en) * 1959-10-30 1961-11-08 Universal Oil Prod Co A process for separating butylenes from butane
GB939470A (en) * 1961-01-26 1963-10-16 Metallgesellschaft Ag The separation of olefinic hydrocarbons from mixtures containing the same
US4132744A (en) * 1977-12-12 1979-01-02 Texaco Inc. Process for separating liquid olefin-paraffin mixtures
US4267034A (en) * 1979-11-14 1981-05-12 Phillips Petroleum Company Separating olefins from paraffins with dimethyl sulfoxide extractant
US5068011A (en) * 1990-10-26 1991-11-26 Phillips Petroleum Company Separation of monoolefins from paraffins
RU2379277C1 (en) * 2008-06-30 2010-01-20 Олег Станиславович Павлов Method of separating alkane and alkene fractions
CN103232313A (en) * 2013-05-06 2013-08-07 北京化工大学 Extraction and separation method of alkane/olefin
CN103864554A (en) * 2014-04-09 2014-06-18 天津市昊永化工科技有限公司 Method for extracting, rectifying and separating alkane, olefin and arene from hydrocarbon mixture
CN106966852A (en) * 2016-01-14 2017-07-21 天津大学 The method that continuous extraction rectifying separates high-carbon n-alkane and normal olefine
CN108929188A (en) * 2017-05-23 2018-12-04 中国石油化工股份有限公司 From mixing C4The method of separation of extractive distillation butane and butylene in hydrocarbon raw material
EP3428142A1 (en) * 2017-07-14 2019-01-16 Basf Se Process for separating paraffins and olefins

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