Method for separating benzene, cyclohexene and cyclohexane
By selectively adsorbing and separating benzene, cyclohexene and cyclohexane using Q[7] powder material, the problems of high energy consumption and complex operation in traditional methods are solved, and a low-cost and efficient separation effect is achieved.
Patent Information
- Application Number
- CN202511020069.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-07-23
- Publication Date
- 2025-11-28
AI Technical Summary
Existing technologies are insufficient for efficiently separating mixtures of benzene, cyclohexene, and cyclohexane. Traditional methods are energy-intensive and complex to operate, resulting in high production costs.
The mixture of benzene, cyclohexene and cyclohexane was selectively adsorbed using Q[7] powder material, and separation was achieved by the order of preferential adsorption. The material can be recycled.
It achieves a separation process with low energy consumption and simple operation, reduces production costs, and Q[7] powder material has high stability and can be reused multiple times.
Smart Images
Figure CN121021250A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to a method for separating benzene, cyclohexene, and cyclohexane, belonging to the field of chemical engineering technology. Background Technology
[0002] Benzene (C6H6) has a wide range of applications, primarily in the chemical and pharmaceutical fields. In the chemical industry, benzene is an important raw material for the production of various chemical products such as styrene, phenol, cyclohexane, and adipic acid. In the pharmaceutical industry, benzene and its derivatives are used to synthesize various drugs, such as aspirin and antibiotics. It is also an important chemical intermediate. The demand for high-purity benzene in the chemical industry is increasing.
[0003] Cyclohexene (C6H) 10 Adipic acid is an important chemical raw material, industrially used to produce adipic acid, adipaldehyde, maleic acid, cyclohexanoic acid, cyclohexanal, maleic acid, cyclohexylformic acid, and cyclohexylformaldehyde. It can also be used as an extractant and stabilizer.
[0004] Cyclohexane (C6H) 12 It is also an important chemical raw material, which can be used as a solvent, fuel additive and organic synthesis.
[0005] In industrial production, the hydrogenation reaction of C6H6 is an important process. C6H6 can undergo a complete hydrogenation reaction to yield C6H2O. 12 C6H can also be obtained through partial hydrogenation. 10 However, in both processes, C6H6 cannot be completely converted. It is necessary to separate C6H6 and C6H... 10 C6H 12 Binary or ternary mixtures are used to obtain high-purity chemicals. These three compounds have similar boiling points (C6H6 80.1℃, C6H...). 10 82.8℃, C6H 12 The temperature reaches 80.7℃, making separation by traditional distillation impossible. Although extraction and azeotropic distillation are used in industry, these processes are complex and energy-intensive, resulting in high operating costs.
[0006] There are currently no literature reports on the use of Q[7] to separate benzene-cyclohexene-cyclohexane. The present invention uses Q[7] powder material to effectively separate a mixture of benzene, cyclohexene and cyclohexane. Q[7] powder material is a macrocyclic host material with good thermal stability, can be reused multiple times, and has low energy consumption. No desorbent is required during the desorption process. Applying macrocyclic host materials to the separation of benzene, cyclohexene and cyclohexane will greatly reduce the production cost of benzene, cyclohexene and cyclohexane. Summary of the Invention
[0007] The technical problem to be solved by the present invention is to provide a method for separating benzene, cyclohexene and cyclohexane, which uses Q[7] powder material to adsorb and separate binary / ternary mixtures of benzene, cyclohexene and cyclohexane, with low energy consumption and simple process.
[0008] To solve the above technical problems, the present invention adopts the following technical solution: A method for separating benzene, cyclohexene and cyclohexane, wherein the separation method uses Q[7] powder material to selectively adsorb a binary / ternary mixture of benzene-cyclohexene-cyclohexane. The selective adsorption is carried out in the order of preferential adsorption of benzene, cyclohexene and cyclohexane, so that the binary / ternary mixture is adsorbed on the surface of the Q[7] powder material, thereby achieving the separation of benzene, cyclohexene and cyclohexane, and the Q[7] powder material with the binary / ternary mixture adsorbed on its surface can be recycled; The structural formula of the Q[7] material is as follows: .
[0009] The aforementioned binary / ternary mixture of benzene-cyclohexene-cyclohexane is a mixture of benzene and cyclohexene, a mixture of benzene and cyclohexane, a mixture of cyclohexene and cyclohexane, or a mixture of benzene, cyclohexene, and cyclohexane.
[0010] The aforementioned binary / ternary mixture of benzene, cyclohexene, and cyclohexane is a mixed vapor or a mixed solution.
[0011] The temperature range for selective adsorption of benzene, cyclohexene, and cyclohexane is 20–90 °C.
[0012] Specifically, the temperature for selective adsorption of benzene, cyclohexene, and cyclohexane is 20~70℃.
[0013] The aforementioned Q[7] powder material with a binary / ternary mixture adsorbed on its surface can be desorbed by air drying at room temperature to remove the benzene, cyclohexene and cyclohexane adsorbed on the surface, and finally benzene, cyclohexene and cyclohexane are desorbed and recycled in turn.
[0014] Specifically, the aforementioned room temperature air-drying time is 20-30 hours.
[0015] More specifically, the aforementioned room temperature air-drying time is 24 hours.
[0016] Specifically, the desorption temperature is 90~110℃ and the time is 1~3h.
[0017] More specifically, the aforementioned desorption temperature was 100℃ and the time was 2 hours.
[0018] Compared with the prior art, the present invention has the following beneficial effects: The separation process is simple to operate and requires low equipment; the separation process does not require distillation, has low energy consumption, saves energy, and reduces the production cost of benzene, cyclohexene and cyclohexane; the Q[7] powder material used has high stability, can be recycled, and the separation effect will not be reduced. Attached Figure Description
[0019] Figure 1 The following are PXRD characterization results of the Q[7] powder material of Example 1 and the Q[7] powder material of Example 2 after vapor adsorption separation of benzene, cyclohexene and cyclohexane; Figure 2 The following are PXRD characterization results of the Q[7] powder material of Example 1 and the Q[7] powder material of Examples 3-6 after solution adsorption separation of benzene, cyclohexane and cyclohexene; Figure 3 The figure shows the gas chromatographic characterization results of the adsorption separation of benzene and cyclohexane by Q[7] powder material in Example 3; Figure 4 The figure shows the gas chromatographic characterization results of the adsorption separation of benzene and cyclohexene by Q[7] powder material in Example 4; Figure 5 The figure shows the gas chromatographic characterization results of the adsorption separation of cyclohexene and cyclohexane by Q[7] powder material in Example 5; Figure 6 The figure shows the gas chromatographic characterization results of the adsorption separation of benzene, cyclohexene and cyclohexane by Q[7] powder material in Example 6; Figure 7 The figure shows the gas chromatographic characterization results of the adsorption separation of benzene and cyclohexane by Q[7] powder material in Example 7; Figure 8 The figure shows the gas chromatographic characterization results of the adsorption and separation of benzene and cyclohexene by Q[7] powder material in Example 8; Figure 9 The figure shows the gas chromatographic characterization results of the adsorption separation of cyclohexene and cyclohexane by Q[7] powder material in Example 9; Figure 10 The figure shows the gas chromatographic characterization results of the adsorption separation of benzene, cyclohexene and cyclohexane by Q[7] powder material in Example 10; Figure 11 When the Q[7] powder material of Example 13 is recycled, the Q[7]-C6H 10 Graph showing the effect of gas-solid cycle adsorption separation; Figure 12 The diagram shows the effect of Q[7]-C6H6 gas-solid cycle adsorption and separation on the Q[7]-C6H6 gas-solid cycle when the Q[7] powder material of Example 14 is recycled. Detailed Implementation
[0020] The present invention will be further described below with reference to the accompanying drawings and specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Operating methods not specifically specified in the following embodiments are generally performed under conventional conditions or as recommended by the manufacturer.
[0021] Example 1 Q[7] Preparation of powder materials: Dissolve a mixture of 400-500g of glycourea and 100-200g of paraformaldehyde in 12mol / L hydrochloric acid and heat under reflux for 4-6 hours to obtain a mixture of various cucurbitacins. Dry the mixture in rotary evaporation at 40-60℃ to obtain a viscous solid. Dissolve 20-30g of the viscous solid in the developing solvent (the developing solvent is water:acetic acid:formic acid = 10mL:10mL:1mL) to obtain a liquid. Pack a 300-1000mm wide-mouth glass frit chromatography column with 500g-1000g of silica gel, pour the liquid in, and then add the developing solvent for column chromatography. Collect the liquid that flows down and evaporate it at 40-60℃ to obtain a white Q[7] powder material.
[0022] The characterization data of the Q[7] powder material product prepared in this embodiment are as follows: Q[7], 1 H NMR (400 MHz, D2O, 298K, ppm) δ 5.72 (d, 14 H), 5.48 (s, 14H), 4.17 (d, 14 H). PXRD test results are as follows Figure 1 As shown, the obtained Q[7] powder material has a very low crystallinity and is amorphous.
[0023] The following Examples 2-10 all use the Q[7] powder material prepared in Example 1.
[0024] Example 2 Q[7] Adsorption of benzene, cyclohexene and cyclohexane vapors separately by powder materials: (1) Take a 20mL culture bottle, add 1mL of benzene, and name it Q[7]-C6H6. Take another 5mL open culture bottle and put 10mg of Q[7] powder material into it. Place it in the 20mL culture bottle containing Q[7]-C6H6. Seal the 20mL culture bottle and place it at 25℃ for 24 hours. After the adsorbed Q[7] powder material is air-dried, it is tested. (2) Take a 20mL culture bottle, add 1mL of cyclohexene, and name it Q[7]-C6H 10 Take another 5 mL open-mouthed culture bottle and put 10 mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[7]-C6H 10The 20mL culture bottle was sealed and placed at 25℃ for 24 hours. The adsorbed Q[7] powder material was then air-dried and tested. (3) Take a 20mL culture bottle, add 1mL of cyclohexane, and name it Q[7]-C6H 12 Take another 5 mL open-mouthed culture bottle and put 10 mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[7]-C6H 12 The 20mL culture bottle was sealed and placed at 25℃ for 24 hours. The adsorbed Q[7] powder material was then air-dried and tested. The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: Q[7]-C6H6, 1 H NMR (400 MHz, D2O:DMSO-d6=4:1, 298K, ppm) δ 6.82 (s, 6 H), 5.72 (d, 14 H), 5.61 (s, 14 H), 4.17 (d, 14 H). Q[7]-C6H 10 , 1 H NMR (400 MHz, D2O:DMSO-d6=4:1, 298K, ppm) δ 5.45 (s 2H), 1.11 (s, 4H), 0.75 (s, 4H), 5.72 (d, 14 H), 5.61 (s, 14 H), 4.17 (d, 14 H). Q[7]-C6H 12 , 1 H NMR (400 MHz, D2O:DMSO-d6=4:1, 298K, ppm) δ 0.54 (s, 12H), 5.72 (d, 14 H), 5.61 (s, 14 H), 4.17 (d, 14 H). 1 H NMR results showed that the Q[7] powder material adsorbed benzene, cyclohexene and cyclohexane in a stoichiometric ratio of 1:1.
[0025] PXRD test results are as follows Figure 2 As shown, compared with the PXRD spectrum of Q[7] powder material, the PXRD spectrum of Q[7] powder material after being placed in benzene, cyclohexene and cyclohexane vapor for a period of time did not change, which indicates that Q[7] after adsorbing the guest remains in an amorphous state.
[0026] Example 3 Q[7] Adsorption of vapors from a 1:1 (volume ratio) mixture of benzene and cyclohexane by powder materials: Take a 20mL culture bottle, add 0.5mL benzene and 0.5mL cyclohexane, and name it Q[6]-C6H6 / C6H 12 (1:1), take another 5mL open-mouthed culture bottle and put 10mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[6]-C6H6 / C6H 12 In a 20mL culture bottle containing (1:1) bacteria, seal the 20mL culture bottle and place it at 25℃ for 24 hours. Then, air dry the adsorbed Q[7] powder material.
[0027] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD test results are as follows Figure 2 As shown, compared with the initial PXRD spectrum of the Q[7] powder material, the PXRD spectrum of the Q[7] powder material after being placed in a mixed vapor of benzene and cyclohexane for a period of time did not change, indicating that the Q[7] after adsorbing the guest remains in an amorphous state. The results of headspace gas chromatography are as follows. Figure 3 The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 100%.
[0028] Example 4 Q[7] Adsorption of vapors from a 1:1 (volume ratio) mixture of benzene and cyclohexene by powder materials: Take a 20mL culture bottle, add 0.5mL benzene and 0.5mL cyclohexane, and name it Q[7]-C6H6 / C6H 10 (1:1), take another 5mL open-mouthed culture bottle and put 10mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[7]-C6H6 / C6H 10 In a 20mL culture bottle containing (1:1) bacteria, seal the 20mL culture bottle and place it at 25℃ for 24 hours. Then, air dry the adsorbed Q[7] powder material.
[0029] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD test results are as follows Figure 2 As shown, compared to the initial PXRD spectrum of the Q[7] powder material, the PXRD spectrum of the Q[7] powder material placed in a mixed vapor of benzene and cyclohexene for a period of time did not change, indicating that the Q[7] after adsorbing the guest remains in an amorphous state. The results of headspace gas chromatography are as follows: Figure 4 The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 100%.
[0030] Example 5 Q[7] Adsorption of vapor from a 1:1 (volume ratio) mixture of cyclohexene and cyclohexane by powder materials: Take a 20mL culture bottle, add 0.5mL benzene and 0.5mL cyclohexane, and name it Q[6]-C6H. 10 / C6H 12 (1:1), take another 5mL open-mouthed culture bottle and put 10mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[6]-C6H6 / C6H 12 In a 20mL culture bottle containing (1:1) bacteria, seal the 20mL culture bottle and place it at 25℃ for 24 hours. Then, air dry the adsorbed Q[7] powder material.
[0031] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD test results are as follows Figure 2 As shown, compared with the initial PXRD spectrum of the Q[7] powder material, the PXRD spectrum of the Q[7] powder material placed in a mixed vapor of cyclohexene and cyclohexane for a period of time did not change, indicating that the Q[7] after adsorbing the guest remains in an amorphous state. The headspace gas chromatography results are as follows: Figure 5 The characteristic peaks at the elution positions of cyclohexene were shown, indicating that Q[7] powder material can selectively adsorb cyclohexene with a selectivity of 95.6%.
[0032] Example 6 Q[7] Adsorption of vapors from a 1:1:1 (volume ratio) mixture of benzene, cyclohexene and cyclohexane by powder materials: Take a 20mL culture bottle, add 0.5mL benzene, 0.5mL cyclohexene and 0.5mL cyclohexane, and name it Q[6]-C6H6 / C6H 10 / C6H 12 (1:1:1), take another 5mL open-mouthed culture bottle and put 10mg of Q[7] powder material into it, and place it in the above-mentioned container containing Q[6]-C6H6 / C6H 10 / C6H 12 In a 20 mL culture bottle containing (1:1:1), seal the 20 mL culture bottle and place it at 25°C for 24 hours. Then, air dry the adsorbed Q[7] powder material.
[0033] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD test results are as follows Figure 2As shown, compared with the initial PXRD spectrum of the Q[7] powder material, the PXRD spectrum of the Q[7] powder material after being placed in a mixed vapor of benzene, cyclohexene, and cyclohexane for a period of time did not change, indicating that the Q[7] after adsorbing the guest remains in an amorphous state. The results of headspace gas chromatography are as follows. Figure 6 The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 96.02%.
[0034] Example 7 Q[7] Adsorption of powder material on a 1:1 (volume ratio) mixed solution of benzene and cyclohexane: Take a 20mL culture bottle, add 1mL of a mixed solution of benzene and cyclohexane in a volume ratio of 1:1, and name it Q[6]-C6H6 / C6H 12 (1:1), take 20mg of Q[7] powder material and place it in the culture bottle and seal it. Place it at 25℃ for 24 hours and air dry the adsorbed Q[7] powder material.
[0035] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD results: The PXRD spectrum of Q[7] powder material did not change after being placed in a mixed solution of benzene and cyclohexane for a period of time, indicating that Q[7] remained amorphous after adsorption of the guest. The headspace gas chromatography results are as follows: Figure 7 The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 99.08%.
[0036] Example 8 Q[7] Adsorption of powder material on a 1:1 (volume ratio) mixed solution of benzene and cyclohexene: Take a 20mL culture bottle, add 1mL of a mixed solution of benzene and cyclohexane in a volume ratio of 1:1, and name it Q[6]-C6H6 / C6H 10 (1:1), take 20mg of Q[7] powder material and place it in the culture bottle and seal it. Place it at 25℃ for 24 hours and air dry the adsorbed Q[7] powder material.
[0037] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD results: The PXRD spectrum of Q[7] powder material did not change after being placed in a mixed solution of benzene and cyclohexene for a period of time, indicating that Q[7] remained amorphous after adsorption of the guest. The headspace gas chromatography results are as follows: Figure 8The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 100%.
[0038] Example 9 Q[7] Adsorption of powder material on a 1:1 (volume ratio) mixed solution of cyclohexane and cyclohexene: Take a 20mL culture bottle, add 1mL of a mixed solution of benzene and cyclohexane in a volume ratio of 1:1, and name it Q[6]-C6H 12 / C6H 10 (1:1), take 20mg of Q[7] powder material and place it in the culture bottle and seal it. Place it at 25℃ for 24 hours and air dry the adsorbed Q[7] powder material.
[0039] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD results: The PXRD spectrum of Q[7] powder material did not change after being placed in a mixed solution of cyclohexene and cyclohexane for a period of time, indicating that Q[7] remained amorphous after adsorption of the guest. The headspace gas chromatography results are as follows: Figure 9 The characteristic peaks at the cyclohexene elution position are shown, indicating that Q[7] powder material can selectively adsorb cyclohexene with a selectivity of 100%.
[0040] Example 10 Q[7] Adsorption of powder material on a 1:1:1 (volume ratio) mixed solution of benzene, cyclohexene and cyclohexane: Take a 20 mL culture bottle and add 1 mL of a mixed solution of benzene, cyclohexene and cyclohexane in a volume ratio of 1:1:1, and name it Q[6]-C6H 10 C6H 10 / C6H 12 (1:1:1), take 20mg of Q[7] powder material and place it in the culture bottle and seal it. Place it at 25℃ for 24 hours and then air dry the powder.
[0041] The characterization data of the Q[7] powder material after adsorption in this embodiment are as follows: PXRD results: The PXRD spectrum of Q[7] powder material after being placed in a mixed solution of benzene, cyclohexene and cyclohexane for a period of time did not change, indicating that Q[7] remained amorphous after adsorption of the guest. The headspace gas chromatography results are as follows: Figure 10 The characteristic peaks at the elution positions of benzene are shown, indicating that Q[7] powder material can selectively adsorb benzene with a selectivity of 100%.
[0042] Example 11 Q[7] Powder material regeneration: Take 20 mg of Q[7] powder material that has been air-dried at room temperature and saturated with benzene adsorption, heat it in a vacuum oven at 100℃ for 2 hours, and record the sample as Q[7]-D1.
[0043] The characterization data of the product prepared in this embodiment are as follows: Q[7]-D1, 1 H NMR (400 MHz, D2O, 298K, ppm) δ5.72 (d, 14 H), 5.61 (s, 14H), 4.17 (d, 14 H). exist 1 The H NMR spectrum showed that the signal of the hydrogen atom corresponding to benzene had disappeared, which indicates that the Q[7] powder material has completed desorption and regeneration and all benzene molecules have been released.
[0044] Example 12 Q[7] Powder material regeneration: Take 20 mg of Q[7] powder material that has been air-dried at room temperature and saturated with cyclohexene adsorption, heat it in a vacuum oven at 100°C for 2 hours, and record the sample as Q[7]-D2.
[0045] The characterization data of the product prepared in this embodiment are as follows: Q[7]-D2, 1 H NMR (400 MHz, D2O, 298K, ppm) δ5.72 (d, 14 H), 5.61 (s, 14H), 4.17 (d, 14 H). exist 1 The H NMR spectrum showed that the signal of the hydrogen atom corresponding to cyclohexene had disappeared, which indicates that the Q[7] crystal material has completed desorption and regeneration and all cyclohexene molecules have been released.
[0046] Example 13 Q[7] Reuse of powder materials: The operation process of Example 6 (benzene) was repeated, except that the Q[7] powder material was replaced with the recycled Q[7] powder material.
[0047] The results of headspace gas chromatography indicate that, Figure 11 As shown, Q[7] powder material can selectively adsorb benzene vapor with a selectivity greater than 95.29%, and its selectivity does not decrease after being reused 5 times.
[0048] Example 14 Q[7] Reuse of powder materials: The operation process of Example 5 (cyclohexene) was repeated, except that Q[7] powder material was replaced with 20mg of regenerated Q[7] powder material in Example 5 (cyclohexene).
[0049] The results of headspace gas chromatography indicate that, Figure 12 It can be seen that Q[7] powder material can selectively adsorb cyclohexene vapor with a selectivity greater than 94.2%, and its selectivity does not decrease after being reused 5 times.
[0050] Furthermore, it should be understood that after reading the above description of the present invention, those skilled in the art can make various alterations or modifications to the present invention, and these equivalent forms also fall within the scope defined by the appended claims.
Claims
1. A process for the separation of benzene, cyclohexene and cyclohexane, characterized in that: The separation method is selective adsorption of a binary / trinary mixture of benzene, cyclohexene and cyclohexane by Q[7] powder material, and the selective adsorption is carried out in the order of preferential adsorption of benzene, cyclohexene and cyclohexane, so that the Q[7] powder material surface is adsorbed with the binary / trinary mixture to realize separation of benzene, cyclohexene and cyclohexane, and the Q[7] powder material surface adsorbed with the binary / trinary mixture can be recycled; The structural formula of the Q[7] material is as follows: 。 2. The separation process of benzene, cyclohexene and cyclohexane according to claim 1, characterized in that: The binary / trinary mixture of benzene, cyclohexene and cyclohexane is a mixture of benzene and cyclohexene, a mixture of benzene and cyclohexane, a mixture of cyclohexene and cyclohexane, or a mixture of benzene, cyclohexene and cyclohexane.
3. The process for separating benzene, cyclohexene and cyclohexane according to claim 1, characterized in that: The binary / trinary mixture of benzene, cyclohexene and cyclohexane is a mixed vapor or a mixed solution.
4. The process for separating benzene, cyclohexene and cyclohexane according to claim 1, characterized in that: The temperature for selective adsorption of benzene, cyclohexene and cyclohexane is 20-90℃.
5. The separation process of benzene, cyclohexene and cyclohexane according to claim 4, characterized in that: The temperature for selective adsorption of benzene, cyclohexene and cyclohexane is 20-70℃.
6. The process of claim 1 for separating benzene, cyclohexene and cyclohexane, characterized in that: The Q[7] powder material surface adsorbed with the binary / trinary mixture can remove the surface-adsorbed benzene, cyclohexene and cyclohexane by room temperature air drying method, and then desorption is carried out to obtain benzene, cyclohexene and cyclohexane, which are recycled in turn.
7. The separation process of benzene, cyclohexene and cyclohexane according to claim 6, characterized in that: The room temperature air drying time is 20-30h.
8. The separation process of benzene, cyclohexene and cyclohexane according to claim 7, characterized in that: The room temperature air drying time is 24h.
9. The method of separating benzene, cyclohexene and cyclohexane of claim 6, wherein: The desorption temperature is 90-110℃, and the time is 1-3h.
10. The method of separating benzene, cyclohexene and cyclohexane according to claim 9, characterized in that: The desorption temperature is 100℃, and the time is 2h.