CN111440045A - Separation method of carbon-pentaene mixture - Google Patents
Separation method of carbon-pentaene mixture Download PDFInfo
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- CN111440045A CN111440045A CN202010310841.8A CN202010310841A CN111440045A CN 111440045 A CN111440045 A CN 111440045A CN 202010310841 A CN202010310841 A CN 202010310841A CN 111440045 A CN111440045 A CN 111440045A
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- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
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Abstract
The invention discloses a separation method of a carbon-pentaene mixture, wherein the carbon-pentaene mixture contains isoprene; the separation method takes a fluorine-containing anion hybrid porous material with a flexible function as a separation adsorbent, and the carbon-pentaolefin mixture is contacted with the separation adsorbent for adsorption, so that the separation of isoprene from other carbon-pentaolefins is realized; the fluorine-containing anion hybrid porous material has a double-interpenetration structure with a general structural formula of A- (C)12H8N2) -M, wherein: m is a metal ion selected from Cu2+、Zn2+、Co2+Or Ni2+(ii) a A is an inorganic fluorine-containing anion selected from SiF6 2‑、TiF6 2‑、GeF6 2‑Or NbOF5 2‑；C12H8N2Is organic ligand 1, 2-dipyridyl acetylene.
Description
Technical Field
The invention relates to the technical field of chemical engineering, in particular to a separation method of a carbon-pentaene mixture.
Background
The deep separation and purification of the carbon five (C5) olefin has important industrial value, wherein the components with higher utilization value and higher content comprise isoprene, cyclopentadiene and piperylene, and the three components account for about 40-60% of the total components of C5. The diolefins have special molecular structures and active chemical properties and are valuable basic chemical raw materials. Isoprene (polymer grade and chemical grade) has wide application in the production of synthetic rubber, medical and pesticide intermediates, synthetic lubricating oil additives and rubber vulcanizing agents, and has very wide development and utilization prospects.
The difficulty in separating and purifying isoprene is that the C five fraction contains dozens of components such as alkane, monoolefin, dialkene, cyclane and cycloolefine, the boiling points of the components are similar, the relative volatility is small, some components can form azeotrope (such as isoprene and n-pentane), and the chemical property of diolefin is easy to generate self polymerization or copolymerization (such as cyclopentadiene), so that a high-purity product is difficult to obtain by adopting a common rectification method. At present, the method generally adopted in the industry is to polymerize cyclopentadiene into solid dicyclopentadiene by a thermal dimerization method to separate the solid dicyclopentadiene from carbon five fraction, then to separate polymerization grade cyclopentadiene from dicyclopentadiene by a heating depolymerization method, and to separate other components by a multi-step extraction rectification method to finally obtain polymerization grade isoprene, such as US4570029A, US4438289A, US4147848A and US 3510405A. The method adopting the extractive distillation generally has the problems of high separation energy consumption, high equipment investment, complex flow, solvent recovery, pollution and the like.
With the development and research of adsorptive separation materials, adsorption technology is considered to be one of the most potential separation technologies. Traditional materials such as activated carbon, molecular sieves, porous polymers, etc. have been extensively studied and made significant progress as adsorbent materials. However, the conventional materials have low molecular discrimination with a slight difference in size and low efficiency. For example, patent nos. CN102329179A and CN102351630A, the modified 5A molecular sieve can selectively adsorb normal olefins with smaller molecular size, but the 5A molecular sieve has the problems of small adsorption capacity for normal olefins, low separation selectivity, and the like.
In recent years, more researchers have investigated the separation performance of metal organic frame materials in normal and isomeric hydrocarbons, and the research is generally focused on C2-C4 olefin separation and C5-C8 paraffin separation, although the normal and isomeric separation materials of paraffin are many, the materials for separating C5 and above liquid olefin are few, while olefin contains double bond structure, has slightly smaller molecular size than paraffin and is active in chemical property, and has more strict requirements on the chemical property stability and regeneration performance of materials compared with paraffin separation, and in 2010, Michael MaMI et al have investigated L-96, [ Cu ] Cu3(BTC)2]Chabazite and 5A molecular sieves separation performance on C5 mixtures. Wherein [ Cu3(BTC)2]The adsorption capacities for 1-pentene and isoprene are almost the same, the Separation of n-isoolefins is not provided and the regeneration of these four Materials is not mentioned too much (Separation of C5-Hydrocarbons on Microporous Materials: comparative Performance of MOFs and zeolites [ J]J.AM.CHEM.SOC.2010,132, 2284-2292. 2018 yellow flying crane et al studied the separation of C5 monoolefin isomers by column EtP5 α material which recognizes α and β olefin isomers, is chemically stable and renewable, but has not high adsorption capacity (L olefin Positional Isomer mixing in Nonporous adaptive crystals of a Pillar [5 ] (L olefin Positional Isomer mixing in Nonporous adaptive crystals of A Pillar)]arene[J].J.AM.CHEM.SOC.2018,140-9,3190-3193)。
It can be seen that the existing MOFs materials have the phenomenon that the selectivity and the adsorption capacity cannot be simultaneously obtained for separating C5 olefin, and development of new separation materials and separation methods is urgently needed.
Disclosure of Invention
Aiming at the defects in the field, the invention provides a separation method of a carbon pentaolefin mixture, which adopts a fluorine-containing anion hybrid porous material with a flexible structure to realize the high-efficiency separation and purification of isoprene in carbon pentaolefin.
A method for separating a mixture of carbon pentaenes, the mixture of carbon pentaenes containing isoprene;
the separation method takes a fluorine-containing anion hybrid porous material with a flexible function as a separation adsorbent, and the carbon-pentaolefin mixture is contacted with the separation adsorbent for adsorption, so that the separation of isoprene from other carbon-pentaolefins is realized;
the fluorine-containing anion hybrid porous material has a double-interpenetration structure with a general structural formula of A- (C)12H8N2) -M, wherein:
m is a metal ion selected from Cu2+、Zn2+、Co2+Or Ni2+；
A is an inorganic fluorine-containing anion selected from SiF6 2-、TiF6 2-、GeF6 2-Or NbOF5 2-The three-dimensional structural formula is:
wherein the black sphere represents F or O;
C12H8N2is organic ligand 1, 2-dipyridine acetylene, and the three-dimensional structural formula is as follows:
the fluorine-containing anion hybrid porous material used by the invention is prepared from metal ions, inorganic anions and organic ligands, and the three-dimensional structure is shown in figure 1. After the material is contacted with a C5 olefin mixture containing isoprene, the adsorption capacity to the isoprene is weak, and the adsorption to other components in the mixture is strong, so that high-purity isoprene is separated from a C5 mixture. The C5 olefin mixture contains isoprene, and at least one of 1-pentene, trans-2-pentene, cis-2-pentene, piperylene and cyclopentadiene.
The average pore diameter of the fluorine-containing anion hybrid porous material is within
The pyridine ring in the frame has certain flexibility and can deflect to different degrees along with the adsorption process.
The invention realizes the adjustment of the aperture size of the fluoride anion hybrid porous material with the flexible function by selecting different inorganic fluoride anions and metal ions, and modifies the chemical environment in the pore channel. The proper pore size enables the material to realize different degrees of molecular exclusion for carbon five components with different sizes, and olefins with larger sizes are not easy to enter pore channels. The electrostatic interaction strength of anions and gas molecules in the material is different, and different separation selectivity is shown, so that the efficient separation of C5 olefin is realized. Therefore, the material shows high separation selectivity and adsorption capacity, and has a very good application prospect when being used as an adsorbent for C5 olefin separation and isoprene purification.
The fluorine-containing anion hybrid porous material consists of fluorine-containing anions A, metal ions M and organic ligand 1, 2-dipyridyl acetylene (C)12H8N2) The structural unit is shown in figure 2.
The synthesis of the fluorine-containing anion hybrid porous material can adopt the prior art, such as a room temperature coprecipitation method, a hydrothermal synthesis method, a wet mechanical grinding method and a slow diffusion interface synthesis method, has mild synthesis conditions and is easy to synthesize in batches.
Preferably, the hydrocarbon mixture of carbon pentaene further contains at least one of 1-pentene, trans-2-pentene, cis-2-pentene, piperylene and cyclopentadiene.
Preferably, the mole percentage content of isoprene in the carbon-pentaene hydrocarbon mixture is 10% -98%.
According to the separation method disclosed by the invention, the purity of the isoprene obtained by separation is more than 99.9% (mole percentage).
In order to obtain a better separation effect, the adsorption temperature of the separation method is preferably-20-70 ℃, further preferably-5-50 ℃, and the adsorption pressure is preferably 0-10 bar, further preferably 0.5-2 bar.
According to the separation method, after the contact adsorption of the carbon-pentaene mixture and the separation adsorbent is finished, the separation adsorbent is desorbed, and the regeneration of the separation adsorbent is realized.
The desorption can adopt inert gas purging, desorbent desorption or vacuum desorption. The inert gas is a noble gas and/or nitrogen.
The desorption temperature is preferably 0-150 ℃, further preferably 20-50 ℃, and the pressure is preferably 0-1 bar, further preferably 0-0.2 bar.
The separation method of the invention can adopt fixed bed adsorption or simulated moving bed adsorption. The mixture of the carbon pentaolefins may be in a liquid phase or a gas phase.
In a preferred embodiment, the inorganic fluorine-containing anion A is TiF6 2-The organic ligand is 1, 2-dipyridyl acetylene, and the metal ion is Cu2+The formed flexible fluorine-containing anion hybrid porous material is TIFSIX-2-Cu-i. The adsorption capacity of the TIFSIX-2-Cu-i to trans-2-pentene and 1-pentene is respectively as high as 3.1mmol/g and 2.7mmol/g under the conditions of 45kPa and 298K, and the adsorption capacity to isoprene is only 1.7 mmol/g; the adsorption capacities of trans-2-pentene and 1-pentene under the conditions of 8.5kPa and 298K were 2.5mmol/g and 2.0mmol/g, respectively, and the adsorption capacity of isoprene was only 0.6 mmol/g.
In another preferred embodiment, the inorganic fluorine-containing anion A is NbOF5 2-The organic ligand is 1, 2-dipyridyl acetylene, and the metal ion is Cu2+The flexible fluorine-containing anion hybrid porous material is NbOFFIVE-2-Cu-i. NbOFFIVE-2-Cu-i has adsorption capacities of 2.2mmol/g and 1.6mmol/g for trans-2-pentene and 1-pentene respectively under the conditions of 8.5kPa and 298K, and hardly adsorbs isoprene. Polymer grade isoprene can be separated from the C5 olefin mixture.
The invention also provides application of the fluorine-containing anion hybrid porous material with the flexible function in selective adsorption of carbon pentaolefin.
Preferably, the hydrocarbon is at least one selected from isoprene, 1-pentene, trans-2-pentene, cis-2-pentene, piperylene and cyclopentadiene.
Compared with the prior art, the invention has the main advantages that:
(1) the invention provides a method for adsorbing and separating C5 olefin by using a flexible anion hybrid porous material, which separates olefin by accurately regulating and controlling the aperture of the anion hybrid porous material, thereby obtaining high-purity isoprene;
(2) compared with the traditional adsorbent, the flexible anion hybrid porous material adopted by the invention has the advantages of adjustable pore structure, large pore volume, adjustable acting force with adsorbate molecules and the like, can realize shape-selective separation of C5 olefin, and simultaneously has high capacity and high selectivity;
(3) the process adopted by the invention is a fixed bed sheet column process or a simulated moving bed process, and compared with the traditional extractive distillation method, the provided separation method has the advantages of small equipment investment, low energy consumption and the like.
(4) The method provided by the invention can finally obtain the polymer grade isoprene according to the industrial requirements, and the purity can reach 99.9% (mol percentage).
(5) Compared with the conventional adsorbent, the flexible anion hybrid porous material adopted by the invention has the advantages of mild regeneration conditions, long service life, simple preparation, mild synthesis conditions, easiness in batch synthesis, wide industrial application prospect and the like;
(6) compared with a 5A molecular sieve material, the flexible anion hybrid porous material adopted by the invention has more excellent regeneration performance, does not need to be heated, and can be regenerated by inert gas purging at normal temperature.
Drawings
FIG. 1 shows a reaction mixture of an inorganic fluorine-containing anion A, a metal ion M and an organic ligand 1, 2-dipyridyl acetylene (C)12H8N2) A three-dimensional structure schematic diagram of the fluorine-containing anion hybrid porous material with the flexible function, which is constructed through coordination bonds;
FIG. 2 shows a reaction mixture of an inorganic fluorine-containing anion A, a metal ion M and an organic ligand 1, 2-dipyridyl acetylene (C)12H8N2) A schematic structural unit diagram of the fluorine-containing anion hybrid porous material with the flexible function constructed by coordinate bonds;
FIG. 3 is the adsorption isotherms of the anion hybrid porous material TIFSIX-2-Ni-i material obtained in example 1 for 1-pentene, trans-2-pentene and isoprene at 298K;
FIG. 4 is an adsorption isotherm of the anion hybrid porous material GeFSIX-2-Cu-i material obtained in example 2 for 1-pentene, trans-2-pentene and isoprene at 298K;
FIG. 5 is adsorption isotherms of the anion hybrid porous material SIFIX-2-Cu-i material obtained in example 3 for 1-pentene, trans-2-pentene and isoprene at 298K;
FIG. 6 is the adsorption isotherms of the anion hybrid porous material TIFSIX-2-Cu-i material obtained in example 4 for 1-pentene, trans-2-pentene and isoprene at 298K;
FIG. 7 is the adsorption isotherms of the anion hybrid porous material NbOFFIVE-2-Cu-i material obtained in example 5 for 1-pentene, trans-2-pentene and isoprene at 298K;
FIG. 8 is the adsorption isotherm of the anion hybrid porous material NbOFFIVE-2-Zn-i material obtained in example 6 for 1-pentene and isoprene at 298K;
FIG. 9 is a graph of the penetration of the anion hybrid porous material TIFSIX-2-Cu-i material of example 7 at 298K for a mixture of 1-pentene and isoprene;
FIG. 10 is a graph of the penetration curve of the anion hybrid porous material TIFSIX-2-Cu-i material of example 7 at 298K for a mixture of 1-pentene, trans-2-pentene and isoprene;
FIG. 11 is a graph of the penetration curve of the anion hybrid porous material NbOFFIVE-2-Cu-i material of example 8 at 298K for a mixture of 1-pentene and isoprene;
FIG. 12 is a graph of the penetration curve of the anion hybrid porous material NbOFFIVE-2-Cu-i material of example 8 at 298K for a mixture of 1-pentene, trans-2-pentene and isoprene;
FIG. 13 is a graph of the adsorption performance of TIFSIX-2-Cu-i and NbOFFIVE-2-Cu-i on 1-pentene in example 9 over cycles.
Detailed Description
The invention is further described with reference to the following drawings and specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The following examples are conducted under conditions not specified, usually according to conventional conditions, or according to conditions recommended by the manufacturer.
Example 1
1.0mmol of Ni (BF)4)2、1.0mmol(NH4)2TiF6Dissolving in 10m L anhydrous methanol, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, mixing and stirring the two solutions at 20-85 ℃, performing suction filtration after the reaction is finished to obtain a product, washing the product with methanol for 3-4 times, soaking in methanol for activation for 1 day, and performing vacuum pumping activation for 24 hours at 85 ℃ to obtain the fluoride-containing anion hybrid porous material TIFSIX-2-Ni-i with a flexible function.
The single-component adsorption isotherm of TIFSIX-2-Ni-i at 298K for 1-pentene, trans-2-pentene and isoprene was measured, and the results are shown in FIG. 3, which shows that the material can achieve the above separation of the C5 olefin component.
Example 2
1.0mmol of Cu (BF)4)2·H2O、1.0mmol(NH4)2GeF6Dissolving in 10m L water, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, mixing and stirring the two at 65 ℃ for 24h, carrying out suction filtration and methanol washing on the obtained material for 3-4 times, and carrying out vacuum activation at room temperature for 24h to obtain the fluoride-containing anion hybrid porous material GeFSIX-2-Cu-i with a flexible function.
The single-component adsorption isotherms of GeFSIX-2-Cu-i at 298K for 1-pentene, trans-2-pentene and isoprene were measured, and the results are shown in FIG. 4, which shows that the material can achieve the separation of the C5 olefin component.
Example 3
1.0mmol of Cu (BF)4)2·H2O、1.0mmol(NH4)2SiF6Dissolving in 10m L water, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, mixing and stirring the two at 85 ℃ for 12h, carrying out suction filtration and methanol washing on the obtained material for 3-4 times, and carrying out vacuum activation at 65 ℃ for 24h to obtain the fluoride-containing anion hybrid porous material SIFIX-2-Cu-i with a flexible function.
The single-component adsorption isotherm of SIFSIX-2-Cu-i at 298K for 1-pentene, trans-2-pentene and isoprene was measured, and the results are shown in FIG. 5, which shows that the material can realize the separation of the C5 olefin component.
Example 4
1.0mmol of Cu (BF)4)2·H2O、1.0mmol(NH4)2TiF6Dissolving in 10m L water, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, mixing and stirring the two at 85 ℃ for 12h, carrying out suction filtration on the obtained slurry, and activating at 80 ℃ under a vacuum condition for 24h to obtain the fluoride-containing anion hybrid porous material TIFSIX-2-Cu-i with a flexible function.
The single-component adsorption isotherm of TIFSIX-2-Cu-i at 298K for 1-pentene, trans-2-pentene and isoprene was measured, and the results are shown in FIG. 6, which shows that the material can achieve the above separation of the C5 olefin component.
Example 5
1.0mmol of CuNbOF5Dissolving in 10m L water, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, dropwise adding a ligand solution into a magnetically stirred inorganic salt solution, heating at 80 ℃ for reaction for 24h, carrying out suction filtration on a product, washing with methanol for 3-4 times, and activating at room temperature for 24h to obtain the fluorine-containing anion hybrid porous material NbOFFIVE-2-Cu-i with a flexible function.
The single-component adsorption isotherm of NbOFFIVE-2-Cu-i at 298K for 1-pentene, trans-2-pentene and isoprene was measured, and the results are shown in FIG. 7, which shows that the material can achieve the separation of the C5 olefin component.
Example 6
1.0mmol of ZnNbOF5Dissolving in 10m L water, dissolving 1.5mmol of 1, 2-dipyridyl acetylene in 10m L methanol, dropwise adding a ligand solution into a magnetically stirred inorganic salt solution, heating at 80 ℃ for reaction for 24h, carrying out suction filtration on a product, washing with methanol for 3-4 times, and activating at room temperature for 24h to obtain the fluorine-containing anion hybrid porous material NbOFFIVE-2-Zn-i with a flexible function.
The single-component adsorption isotherm of NbOFFIVE-2-Zn-i at 298K for 1-pentene and isoprene was measured, and the results are shown in FIG. 8, which shows that the material can realize the separation of the C5 olefin component.
Example 7
The TIFSIX-2-Cu-i of example 4 was packed in a 5cm adsorption column, 0.1MPa mixed vapor of 1-pentene and isoprene (molar ratio 1:1) was introduced into the column at 25 ℃ at 1m L/min, the breakthrough curve is shown in FIG. 9, high purity isoprene was obtained from the effluent gas, adsorption was stopped when 1-pentene had penetrated, the adsorption column was purged at room temperature with nitrogen and recycled.
The TIFSIX-2-Cu-i of example 4 was packed in a 5cm adsorption column, mixed vapor of 0.1MPa 1-pentene, trans-2-pentene and isoprene (molar ratio 1:1:1) was introduced into the adsorption column at 25 ℃ at 1m L/min, the breakthrough curve is shown in FIG. 10, high purity isoprene was obtained from the effluent gas, adsorption was stopped when trans-2-pentene had penetrated, then nitrogen was switched to purge the adsorption column at room temperature, and the adsorption column was recycled.
Example 8
The NbOFFIVE-2-Cu-i of example 5 is filled in a 5cm adsorption column, 0.1MPa of mixed steam of 1-pentene and isoprene (molar ratio 1:1) is introduced into the adsorption column at 25 ℃ at 1m L/min, the penetration curve is shown in FIG. 11, high-purity isoprene (hollow circle in FIG. 11) can be obtained from the effluent gas, adsorption is stopped when the 1-pentene (solid circle in FIG. 11) penetrates, then the nitrogen is switched to purge the adsorption column at room temperature, and the adsorption column can be recycled.
The NbOFFIVE-2-Cu-i of example 5 was packed in a 5cm adsorption column, mixed vapor of 0.1MPa of 1-pentene, trans-2-pentene and isoprene (molar ratio 1:1:1) was introduced into the adsorption column at 25 ℃ at 1m L/min, the breakthrough curve was as shown in FIG. 12, high purity isoprene was obtained from the effluent gas, adsorption was stopped when trans-2-pentene had penetrated, and then the adsorption column was purged with nitrogen at room temperature and recycled.
Example 9
The materials prepared in examples 4 and 5 were subjected to a 1-pentene adsorption cycle regeneration performance test at normal temperature, and the obtained results are shown in fig. 13, which demonstrates that the materials are excellent in cycle regeneration stability.
Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the above description of the present invention, and equivalents also fall within the scope of the invention as defined by the appended claims.
Claims (10)
1. A method for separating a mixture of carbon and pentaene, wherein the mixture of carbon and pentaene contains isoprene;
the separation method takes a fluorine-containing anion hybrid porous material with a flexible function as a separation adsorbent, and the carbon-pentaolefin mixture is contacted with the separation adsorbent for adsorption, so that the separation of isoprene from other carbon-pentaolefins is realized;
the fluorine-containing anion hybrid porous material has a double-interpenetration structure with a general structural formula of A- (C)12H8N2) -M, wherein:
m is a metal ion selected from Cu2+、Zn2+、Co2+Or Ni2+；
A is an inorganic fluorine-containing anion selected from SiF6 2-、TiF6 2-、GeF6 2-Or NbOF5 2-；
C12H8N2Is organic ligand 1, 2-dipyridyl acetylene.
2. The separation process of claim 1, wherein the mixture of the pentaolefins further comprises at least one of 1-pentene, trans-2-pentene, cis-2-pentene, piperylene, cyclopentadiene.
3. The separation method according to claim 1 or 2, wherein the mole percentage content of isoprene in the carbon-pentaene hydrocarbon mixture is 10% to 98%.
4. The separation method of claim 1, wherein the purity of the isoprene obtained by the separation is more than 99.9%.
5. The separation method according to claim 1, wherein the adsorption temperature is-20 to 70 ℃ and the adsorption pressure is 0 to 10 bar.
6. The separation method according to claim 1, wherein after the contact adsorption of the pentacene mixture with the separation adsorbent is completed, the separation adsorbent is desorbed to regenerate the separation adsorbent.
7. The separation process of claim 6, wherein the desorption is performed using an inert gas purge, desorbent desorption or vacuum desorption.
8. The separation process according to claim 6, wherein the desorption temperature is 0 to 150 ℃ and the pressure is 0 to 1 bar.
9. The separation method according to any one of claims 5 to 8, wherein fixed bed adsorption or simulated moving bed adsorption is used.
10. An application of a fluorine-containing anion hybrid porous material with a flexible function in selectively adsorbing carbon pentaolefin.
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| CN101472842A (en) * | 2006-06-20 | 2009-07-01 | 西巴控股有限公司 | Process for removing ethene from biological sources using metal exchanged titanium zeolites |
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