CN111517911B - Method for separating m-methyl ethylbenzene from p-methyl ethylbenzene - Google Patents
Method for separating m-methyl ethylbenzene from p-methyl ethylbenzene Download PDFInfo
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- CN111517911B CN111517911B CN202010398303.9A CN202010398303A CN111517911B CN 111517911 B CN111517911 B CN 111517911B CN 202010398303 A CN202010398303 A CN 202010398303A CN 111517911 B CN111517911 B CN 111517911B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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- 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
Abstract
The invention discloses a method for separating m-methyl ethyl benzene and p-methyl ethyl benzene by using a bisdiethoxy column [6]]The aromatic hydrocarbon crystal material is an adsorbent, and a mixture containing m-methyl ethylbenzene and p-methyl ethylbenzene is contacted with the adsorbent for adsorption, so that the separation of the m-methyl ethylbenzene and the p-methyl ethylbenzene is realized; bis (diethoxy) column [6]]The chemical structural formula of the aromatic hydrocarbon crystal material is as follows:
the invention also discloses the bisdiethoxy column [6]]The application of the aromatic hydrocarbon crystal material in selective adsorption of p-methyl-ethyl benzene. The separation process of the invention is simple to operate, and the equipment requirement is low; rectification operation is not needed in the separation process, so that the energy consumption is low, the energy is saved, and the production cost of the p-methyl-ethyl benzene is reduced; the used crystal material has high stability, can be recycled, and the separation effect cannot be reduced.
Description
Technical Field
The invention relates to the technical field of adsorption separation, in particular to a method for separating m-methyl ethyl benzene and p-methyl ethyl benzene.
Background
The catalytic reforming process of petroleum produces a large amount of by-products such as C9, C8 aromatics, and the like. The C9 aromatic hydrocarbon mainly comprises aromatic compounds containing nine carbon atoms such as p-methyl ethyl benzene and m-methyl ethyl benzene. The p-methyl ethyl benzene is an important chemical raw material, can be used for preparing p-methyl styrene through dehydrogenation, and can be polymerized to obtain a novel high polymer material, so that the p-methyl ethyl benzene can be widely applied to engineering plastics, flame-retardant special resins, reinforced polyester fibers and the like. Because many physical properties of the novel material are obviously superior to those of polystyrene, the novel material has great development and application values in industry. Therefore, the method for obtaining high-purity p-methyl-ethyl benzene from the C9 aromatic hydrocarbon compound has important significance for reducing the production cost of the p-methyl-ethyl benzene and improving the utilization rate of petroleum waste.
Higher purity p-methylethylbenzene is obtained from the aromatic C9 compound, the most challenging step being the separation of p-methylethylbenzene and m-methylethylbenzene. Because the boiling points of the m-methyl ethylbenzene (159 ℃) and the p-methyl ethylbenzene (158 ℃) are very close, the separation of the m-methyl ethylbenzene and the p-methyl ethylbenzene by rectification is accompanied with huge energy consumption, the cost is high, and the p-methyl ethylbenzene with higher purity is difficult to obtain. In addition, the molecular sieve can realize the separation of the two by means of adsorption separation. However, this process requires a high purity desorbent, which is likely to cause environmental pollution.
Patent specification CN 105461501 a discloses a method for rectifying and separating intermediate, para-methyl-ethyl benzene of C9 mixture by using a method of adding a salt extracting agent. By adopting salicylate as an extractant in the salified extractant and thiocyanate as salts in the salified extractant, the technical problem that the p-methyl-ethyl benzene in the middle of a C9 aromatic hydrocarbon mixture is difficult to separate is solved. However, the separation process requires a series of rectification and extraction operations, which easily pollute the environment and are accompanied by large energy consumption.
Patent specification CN 101723790A discloses a method for separating m-methyl ethyl benzene and p-methyl ethyl benzene from a C9 aromatic hydrocarbon mixture by using a precision rectification method. Firstly, introducing a C9 aromatic hydrocarbon mixture into a pressurization heavy component removal tower, introducing a light component at the top of the pressurization heavy component removal tower into a decompression light component removal tower, and rectifying for two times to obtain m-methyl ethyl benzene and p-methyl ethyl benzene. However, this method requires a large energy consumption and the final separation effect is not satisfactory.
Disclosure of Invention
Aiming at the defects in the field, and the defects of large energy consumption, complicated process and the like in the separation technology of m-methyl-ethyl benzene and p-methyl-ethyl benzene, the invention provides the separation method of m-methyl-ethyl benzene and p-methyl-ethyl benzene, which utilizes a bis-diethoxy column [6] aromatic hydrocarbon crystal material to adsorb and separate the mixture of m-methyl-ethyl benzene and p-methyl-ethyl benzene, and has low energy consumption and simple process.
A separation method of m-methyl ethyl benzene and p-methyl ethyl benzene is characterized in that a bisdiethoxy column [6] aromatic hydrocarbon crystal material is used as an adsorbent, a mixture containing the m-methyl ethyl benzene and the p-methyl ethyl benzene is contacted with the adsorbent for adsorption, and the separation of the m-methyl ethyl benzene and the p-methyl ethyl benzene is realized;
the chemical structural formula of the bis-diethoxy column [6] arene crystal material is as follows:
the research of the invention finds that due to the difference of molecular structures of m-methyl ethylbenzene and p-methyl ethylbenzene, the bis-diethoxy column [6] arene crystal material can form a host-guest complex with the p-methyl ethylbenzene, and the host-guest complex can be gradually decomplexed when being heated to release the adsorbed p-methyl ethylbenzene. The bis-diethoxy column [6] arene crystal material has stable chemical properties at desorption temperature, can be repeatedly utilized, and has no reduction of selectivity. And the bis-diethoxy column [5] arene crystal material cannot realize the efficient separation of m-methyl ethylbenzene and p-methyl ethylbenzene.
Preferably, the bis-diethoxy column [6] arene crystal material is obtained by activation after recrystallization in a poor solvent. Generally, the poor solvent used is tetrahydrofuran or acetone, but is not limited thereto. The bisdiethoxy column [6] arene crystal material obtained by recrystallization can be heated to remove solvent molecules and then reactivated. The activation temperature is 160 ℃, and the activation time is not less than 2 hours. The activated bis-diethoxy column [6] arene crystal material can be directly used for the adsorption separation of a mixture of m-methyl ethylbenzene and p-methyl ethylbenzene.
Preferably, the temperature of the contact adsorption is not higher than 60 ℃.
Preferably, the separation method specifically comprises the following steps: and (3) placing the bis-diethoxy column [6] arene crystal material in a mixed steam atmosphere of m-methyl ethylbenzene and p-methyl ethylbenzene, wherein the temperature is not higher than 60 ℃. During the adsorption process, the p-methyl ethyl benzene in the mixed vapor and the bis-diethoxy column [6] arene form a host-guest complex, and the stoichiometric ratio of the host-guest complex is 1: 1.
After the contact adsorption is finished, heating the bis-diethoxy column [6] arene crystal material to be not more than 60 ℃ in vacuum, and removing the mixture containing m-methyl ethyl benzene and p-methyl ethyl benzene adsorbed on the surface. The host-guest compound still exists stably under the condition of 60 ℃, and the mixture of m-methyl ethyl benzene and p-methyl ethyl benzene adsorbed on the surface can be volatilized and removed. The purity of the separated p-methyl-ethyl benzene can be improved by removing the m-methyl-ethyl benzene and the p-methyl-ethyl benzene adsorbed on the surface.
The p-methyl ethylbenzene molecules adsorbed and complexed in the bis-diethoxy column [6] arene crystal material can be desorbed in a heating mode, the temperature is 110-120 ℃, and the desorption time is adjusted according to the sample amount. At the temperature, the host-guest complex is unstable, adsorbed p-methyl ethyl benzene molecules are gradually released, and the bis-diethoxy column [6] arene crystal material is stable and only changes the crystal form in the desorption process. And (3) obtaining a regenerated bis-diethoxy column [6] arene crystal material after the desorption is finished, and continuously using the material for adsorbing and separating a mixture containing m-methyl ethyl benzene and p-methyl ethyl benzene for next circulation.
The invention also provides application of the bis-diethoxy column [6] arene crystal material in selective adsorption of p-methyl ethyl benzene. Preferably, the adsorption temperature is not more than 60 ℃.
Compared with the prior art, the invention has the main advantages that: the separation process is simple to operate, and the equipment requirement is low; rectification operation is not needed in the separation process, so that the energy consumption is low, the energy is saved, and the production cost of the p-methyl-ethyl benzene is reduced; the used crystal material has high stability, can be recycled, and the separation effect cannot be reduced.
Drawings
FIG. 1 is a powder X-ray diffraction (PXRD) pattern of the bis-diethoxy-pillared [6] aromatic hydrocarbon crystalline materials of examples 1-5;
FIG. 2 is a graph showing the adsorption separation effect of the cyclic adsorption-regeneration process of m-ethyltoluene and p-ethyltoluene as the crystalline material of bis-diethoxy column [6] aromatic hydrocarbon of example 5, in which PET represents p-ethyltoluene and MET represents m-ethyltoluene.
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
Preparation of bis-diethoxy column [6] arene crystal material: weighing 2g of bis-diethoxy column [6] arene, placing the mixture in 20mL of acetone, heating the mixture to boiling, dropwise adding the acetone until the acetone is completely dissolved, placing the solution at 0 ℃ for storage overnight, filtering the solution to collect precipitated crystals, drying the obtained crystals in vacuum at 50 ℃ and activating the crystals for 2 hours at 160 ℃ to obtain white powder which is recorded as EtP 6.
The product prepared in this example has the following characterization data:
EtP6，1H NMR(400MHz，CDCl3，298K，ppm)δ6.70(s，12H)，3.83(q，36H)，1.28(t，36H)。
PXRD detection results are shown in FIG. 1a, and the obtained bis-diethoxy column [6] arene crystal material has good crystallinity.
Example 2
The adsorption of the bis-diethoxy column [6] aromatic hydrocarbon crystal material to single m-methyl ethyl benzene or p-methyl ethyl benzene: 3 20mL strain bottles are taken, 1mL of m-methylethylbenzene and p-methylethylbenzene are respectively added, which are named as EtP6-MET and EtP6-PET, 50mg of the bis-diethoxy column [6] arene crystal material in the embodiment 1 is respectively placed in two 5mL strain bottles, the two open 5mL strain bottles are placed in two 20mL strain bottles, the 20mL strain bottles are sealed and placed in a 25 ℃ water bath kettle for 30 hours.
The product prepared in this example has the following characterization data:
EtP6-PET,1H NMR(400MHz,CDCl3,298K,ppm)δ7.09(s,4H)6.70(s,12H),3.83(q,36H),2.61(q,2H),2.31(s,3H),1.28(t,36H),1.21(3H)。
EtP6-MET,1H NMR(400MHz,CDCl3,298K,ppm)δ6.70(s,12H),3.83(q,36H),1.28(t,36H)。
1h NMR results showed bis-diethoxy column [6]]The aromatic hydrocarbon crystal material is prepared by mixing 1: the mode 1 adsorbs the p-methyl-ethyl benzene, and the adsorption of the m-methyl-ethyl benzene is extremely trace.
The PXRD detection result is shown in fig. 1c, and the PXRD pattern of the bis-diethoxy column [6] aromatic hydrocarbon crystal material after being placed in the para-methylethylbenzene vapor atmosphere for a period of time is changed relative to the PXRD pattern of the initially activated bis-diethoxy column [6] aromatic hydrocarbon crystal material, which indicates that the unit cell parameters of the bis-diethoxy column [6] aromatic hydrocarbon crystal material have changed, meaning that the para-methylethylbenzene has been adsorbed into the bis-diethoxy column [6] aromatic hydrocarbon crystal material; as shown in FIG. 1b, the PXRD spectrum of the bis-diethoxy column [6] aromatic hydrocarbon crystalline material after being left for a period of time in the atmosphere of m-methylethylbenzene vapor is unchanged from that of the original bis-diethoxy column [6] aromatic hydrocarbon crystalline material, indicating that the unit cell parameters thereof are unchanged, meaning that the bis-diethoxy column [6] aromatic hydrocarbon crystalline material has almost no adsorption capacity for m-methylethylbenzene.
Example 3
Adsorption of a 1:1 mixture of methyl ethyl benzene and m-methyl ethyl benzene by a bis-diethoxy column [6] aromatic hydrocarbon crystal material: a20 mL strain bottle is taken, 0.50mL of p-methylethylbenzene and 0.50mL of m-methylethylbenzene are added and named as EtP6-MPET, 20mg of the bis-diethoxy column [6] aromatic hydrocarbon crystal material in the example 1 is placed in the 5mL strain bottle, the 5mL strain bottle with an opening is placed in the 20mL strain bottle, the 20mL strain bottle is sealed and placed in a 25 ℃ water bath kettle for 40 hours, and the obtained powder is placed in a 50 ℃ vacuum oven for 30 minutes.
The product prepared in this example has the following characterization data:
EtP6-MPET,1H NMR(400MHz,CDCl3,298K,ppm)δ7.09(s,4H)6.70(s,12H),3.83(q,36H),2.61(q,2H),2.33(s,0.14H),2.31(s,3H),1.28(t,36H),1.21(3H)。
in that1The H NMR spectrum showed only a signal of a hydrogen atom corresponding to p-methylethylbenzene, which indicates that the column was a bisdiethoxy column [6]]The aromatic hydrocarbon crystal material can selectively adsorb the p-methyl ethyl benzene. In addition, a weak signal value appears at chemical shift 2.33, which is attributed to methyl group on m-methylethylbenzene, so we can use the signal of the methyl group to calculate the purity of p-methylethylbenzene adsorbed in EtP6 to be 95.5%.
The PXRD detection result is shown in fig. 1d, and the PXRD pattern of the bis-diethoxy column [6] aromatic hydrocarbon crystal material after being placed in the mixed vapor of p-methylethylbenzene and m-methylethylbenzene for a period of time is changed relative to the PXRD pattern of the initially activated bis-diethoxy column [6] aromatic hydrocarbon crystal material, and the pattern change is the same as that of EtP6-PET, which indicates that the bis-diethoxy column [6] aromatic hydrocarbon crystal material can selectively adsorb p-methylethylbenzene.
Example 4
Regeneration of a bis-diethoxy column [6] arene crystal material: 200mg of a crystalline material of bis-diethoxy column [6] arene saturated and adsorbing p-methyl ethyl benzene was heated in a vacuum oven at 110 ℃ for 2 hours and recorded as EtP 6-D.
The product prepared in this example has the following characterization data:
EtP6-D,1H NMR(400MHz,CDCl3,298K,ppm)δ6.70(s,12H),3.83(q,36H),1.28(t,36H)。
in that1The signal of the hydrogen atom corresponding to p-methyl-ethyl benzene was found to have disappeared in the H NMR spectrum, indicating that the column was a bisdiethoxy column [6]]The aromatic hydrocarbon crystal material has completed desorption regeneration, and the methyl ethyl benzene molecule has been completely released.
The PXRD detection result is shown in fig. 1e, and the PXRD spectrum of the desorbed bis-diethoxy column [6] aromatic hydrocarbon crystal material is unchanged relative to the PXRD spectrum of the initially activated bis-diethoxy column [6] aromatic hydrocarbon crystal material, which indicates that the bis-diethoxy column [6] aromatic hydrocarbon crystal material has completed the desorption process.
Example 5
The bis-diethoxy column [6] arene crystal material is recycled: examples 3 and 4 were repeated using 50mg of the regenerated bis-diethoxy column [6] arene crystalline material of example 4.
1The results of H NMR showed that, as shown in FIG. 2, bis-diethoxy column [6]]The aromatic hydrocarbon crystal material can selectively adsorb p-methyl ethyl benzene, the selectivity of the aromatic hydrocarbon crystal material can reach 95.5%, and the selectivity of the aromatic hydrocarbon crystal material is not reduced after the aromatic hydrocarbon crystal material is repeatedly used for 10 times. Repeatedly used and regenerated bis-diethoxy column [6]PXRD test result of the aromatic hydrocarbon crystal material is shown as 1f, and the aromatic hydrocarbon crystal material is combined with a newly prepared bis-diethoxy column [6]]The crystal materials are consistent, and the bis-diethoxy column [6] is fully proved]The crystal material has excellent structural 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 (5)
1. A separation method of m-methyl ethyl benzene and p-methyl ethyl benzene is characterized in that a bis-diethoxy column [6] aromatic hydrocarbon crystal material is used as an adsorbent, and a mixture of the m-methyl ethyl benzene and the p-methyl ethyl benzene in a volume ratio of 1:1 is contacted with the adsorbent for adsorption, so that the separation of the m-methyl ethyl benzene and the p-methyl ethyl benzene is realized;
the chemical structural formula of the bis-diethoxy column [6] arene crystal material is as follows:
the temperature of the contact adsorption is not higher than 60 ℃;
after the contact adsorption is finished, heating the bis-diethoxy column [6] arene crystal material in vacuum to be not more than 60 ℃, removing the mixture containing m-methylethylbenzene and p-methylethylbenzene adsorbed on the surface, then heating to 110-120 ℃ for desorption to obtain p-methylethylbenzene, and realizing the regeneration of the bis-diethoxy column [6] arene crystal material.
2. The separation method according to claim 1, wherein the bis-diethoxy column [6] arene crystalline material is obtained by activation after recrystallization in a poor solvent.
3. The separation method according to claim 2, wherein the poor solvent is tetrahydrofuran or acetone.
4. The separation process according to claim 2, wherein the temperature of the activation is 160 ℃ for not less than 2 hours.
5. The application of the bis-diethoxy column [6] arene crystal material in selective adsorption of p-methyl ethyl benzene in a mixture of m-methyl ethyl benzene and p-methyl ethyl benzene in a volume ratio of 1:1 is characterized in that the chemical structural formula of the bis-diethoxy column [6] arene crystal material is as follows:
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| CN109054042A (en) * | 2018-09-14 | 2018-12-21 | 西北师范大学 | The supermolecule polymer of Subjective and Objective assembling based on twin columns [5] aromatic hydrocarbons and its preparation and application |
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| WO2017025951A1 (en) * | 2015-08-10 | 2017-02-16 | Ramot At Tel-Aviv University Ltd. | Pillararenes and uses thereof |
| WO2019182517A1 (en) * | 2018-03-21 | 2019-09-26 | Nanyang Technological University | Peptide-attached pillar[5]arene for highly permeable and selective artificial water channel, and its synthesis and characterization |
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