CN111116296B - Method for separating benzene and cyclohexane - Google Patents
Method for separating benzene and cyclohexane Download PDFInfo
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- CN111116296B CN111116296B CN201911288846.9A CN201911288846A CN111116296B CN 111116296 B CN111116296 B CN 111116296B CN 201911288846 A CN201911288846 A CN 201911288846A CN 111116296 B CN111116296 B CN 111116296B
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 207
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 56
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 55
- 239000013078 crystal Substances 0.000 claims abstract description 54
- 238000000926 separation method Methods 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000008929 regeneration Effects 0.000 claims description 4
- 238000011069 regeneration method Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002178 crystalline material Substances 0.000 description 11
- 238000001179 sorption measurement Methods 0.000 description 11
- 238000003795 desorption Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000634 powder X-ray diffraction Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000001144 powder X-ray diffraction data Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000012621 metal-organic framework Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000003988 headspace gas chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a separation method of benzene and cyclohexane, which utilizes hetero [3]]The aromatic hydrocarbon crystal material adsorbs and separates the mixture of benzene and cyclohexane, and the hetero [3]]The chemical structural formula of the aromatic hydrocarbon crystal material is as follows:
the separation process of the invention is simple to operate, and the equipment requirement is low; the separation process does not need rectification operation, so that the energy consumption is low, the energy is saved, and the production cost 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 separation method of benzene and cyclohexane.
Background
The separation of benzene and cyclohexane is one of the most challenging tasks in the chemical and petrochemical industries. Benzene is an important petrochemical product and is a volatile organic compound with important industrial and environmental significance. Cyclohexane is an important raw material for varnish, resin and nylon fiber, and is also a raw material for producing cyclohexanol, caprolactam, cyclohexanone and the like. In the chemical industry, cyclohexane is mainly derived from the catalytic hydrogenation of benzene. In order to obtain high purity cyclohexane, it is critical that unreacted benzene be removed from the reactor waste water stream. However, benzene and cyclohexane have similar physical properties and are difficult to separate in petrochemical industry. Since the boiling points of benzene (353.25K) and cyclohexane (353.85K) are very close, differing by only 0.6K, and the formation of an azeotrope makes them nearly impossible to separate by conventional distillation processes. Currently, the main industrial processes for separating mixtures of benzene and cyclohexane are extractive distillation and azeotropic distillation. However, these methods require high energy, with process complexity and high operating costs. Therefore, it is necessary and desirable to develop an easy to operate and more energy efficient process for separating benzene and cyclohexane.
Patent specification with publication number CN 108467333 a discloses a method for producing chlorotoluene by continuous chlorination of toluene, which comprises using an active molecular sieve as a catalyst, continuously chlorinating toluene in a fixed bed, wherein the ratio of benzene to cyclohexane in the chlorinated product is 1.2-6.0, separating to obtain high-purity benzene by aeration and rectification, and the catalyst can be reused, thereby reducing production cost, but the rectification process is accompanied with huge energy consumption.
Patent specification CN 109134189 a discloses a method for obtaining benzene with purity higher than 98% and cyclohexane with purity higher than 92% by continuous rectification in a first tower, an adjacent tower and a counter tower by using mechanical vapor recompression technology, so that the separation efficiency of rectification is greatly improved, but the method still consumes a large amount of energy.
Patent specification EP 0099161 a1 discloses a technique of adsorbing and separating cyclohexane and benzene by using a molecular sieve based on the difference in molecular structure between them, and finally obtaining benzene with a purity of more than 99%.
The adsorption separation by the ordered porous material is an effective separation method by utilizing the difference of the molecular size and the geometric shape of the benzene and the cyclohexane. For example, metal organic framework materials have been experimentally investigated for adsorptive separation of benzene and cyclohexane. However, due to their close molecular size, designing and synthesizing suitable metal organic framework materials for the separation of benzene and cyclohexane is a challenge. Furthermore, metal-organic framework materials composed of reversible metal-coordinate bonds are not sufficiently stable for practical recycling applications. Therefore, there is an urgent need to develop a novel stable and recyclable adsorbent material for efficiently separating benzene and cyclohexane.
Disclosure of Invention
Aiming at the defects in the field, as well as the defects of large energy consumption, complicated process, high-purity desorbent requirement and the like in the benzene and cyclohexane separation technology, the invention provides the benzene and cyclohexane separation method, which utilizes the hetero [3] arene crystal material to adsorb and separate the mixture of benzene and cyclohexane, and has low energy consumption and simple process.
A separation method of benzene and cyclohexane utilizes hetero [3] arene crystal material to adsorb and separate a benzene and cyclohexane mixture, wherein the chemical structural formula of the hetero [3] arene crystal material is as follows:
due to the difference of the molecular structures of benzene and cyclohexane, the hetero [3] arene crystal material can form a host-guest complex with benzene in a stoichiometric ratio of 1: 1. The host-guest complex is unstable and gradually decomplexes upon heating, releasing adsorbed benzene. The hetero [3] arene crystal material is stable at the desorption temperature, can be repeatedly used after the desorption process is finished, and the selectivity cannot be reduced.
The hetero [3] arene crystal material is a prior art material, such as that disclosed by Jiong Zhou et al in Chemical Communications 2016, volume 52, pages 1622-1624.
Preferably, the hetero [3] arene crystalline material is activated after recrystallization in a poor solvent prior to use.
The poor solvent may be acetone, but is not limited thereto.
The hetero [3] arene crystal material obtained by recrystallization can be activated by removing solvent molecules by means of heating. Preferably, the activation temperature is not lower than 150 ℃ and the activation time is not less than 2 hours. The activated hetero [3] arene crystal material may be used directly in the adsorption separation of cyclohexane and benzene mixture.
The specific steps of adsorbing and separating the mixture of benzene and cyclohexane by using the hetero [3] arene crystal material are as follows: and (3) placing the hetero [3] arene crystal material in a mixed steam atmosphere of cyclohexane and benzene, wherein the temperature is less than 80 ℃. The adsorption time may vary depending on factors such as the amount of sample and the ratio of benzene in the mixture. During the adsorption process, the hetero [3] arene crystal material has changed crystal form. Due to multiple non-covalent interactions between CH-pi, CH-O, benzene in the mixed vapor will form a host-guest complex with hetero [3] arene, the stoichiometric ratio of the host-guest complex being 1: 1.
And after the miscellaneous [3] arene crystal material is completely adsorbed in the mixed steam atmosphere of cyclohexane and benzene, taking out the miscellaneous [3] arene crystal material, and then removing the benzene and cyclohexane mixture adsorbed on the surface of the miscellaneous [3] arene crystal material by adopting vacuum heating or reduced pressure heating. Preferably, the temperature of the vacuum heating or reduced pressure heating is less than 80 ℃. The heating time can be adjusted according to the sample amount. The host-guest complex still exists stably under the condition of lower than 80 ℃, and the cyclohexane and benzene mixture adsorbed on the surface can be removed gradually. The purity of the benzene separated by adsorption can be further improved by removing the mixed vapor adsorbed on the surface.
The complex benzene can be absorbed by the impurity [3] arene crystal material by adopting a heating desorption mode, and the regeneration of the impurity [3] arene crystal material is realized at the same time. The desorption time can be adjusted with the sample amount. Preferably, the heating temperature is 80-100 ℃. At the temperature, the host-guest complex is unstable, adsorbed benzene molecules are gradually released, and the hetero [3] arene crystal material is stable and only changes the crystal form in the desorption process. And (3) obtaining the regenerated hetero [3] arene crystal material after the desorption is finished, and continuously adsorbing and separating cyclohexane and benzene for the next circulation.
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; the separation process does not need rectification operation, so that the energy consumption is low, the energy is saved, and the production cost of 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 hetero [3] aromatic crystalline materials of examples 1-4;
FIG. 2 is a gas chromatograph of the separation of benzene and cyclohexane from the crystalline hetero [3] arene material of example 3, with the abscissa representing time in min;
FIG. 3 is a graph showing the effect of the hetero [3] arene crystal material of example 5 on the adsorption separation of cyclohexane and benzene when recycled.
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 hetero [3] arene crystalline material: weighing 2g of hetero [3] arene and placing the hetero [3] arene in 20mL of acetone, heating the mixture to boiling, dropwise adding the acetone until the hetero [3] arene is completely dissolved, placing the solution at 0 ℃ for storage overnight, filtering and collecting precipitated crystals, drying the obtained crystals at 50 ℃ in vacuum, and activating the obtained crystals at 150 ℃ for 2 hours to obtain white powder which is marked as 1.
The product prepared in this example has the following characterization data:
1，1H NMR(400MHz，DMSO-d6，293K，ppm)δ7.17(d,J＝8Hz,2H),6.83(d,J＝8Hz,2H),6.44(s,2H),6.09(s,2H),4.08–3.97(m,8H),3.87(s,6H),3.64(s,6H),3.59(s,6H),3.28(d,J＝16Hz,2H),1.38(t,J＝8Hz,6H)。
PXRD detection results are shown in figure 1, and the obtained hetero [3] arene crystal material has good crystallinity.
Example 2
Adsorption of hetero [3] aromatic crystalline materials on benzene or cyclohexane alone: two 20mL strain bottles were taken, 1mL benzene and 1mL cyclohexane, named 1-Bz and 1-Cy, were added, 200mg of the hetero [3] aromatic crystalline material prepared in example 1 was placed in two 5mL open strain bottles, the two 5mL open strain bottles were placed in two 20mL strain bottles, the 20mL strain bottles were sealed, and the two bottles were placed in a 25 ℃ water bath for 30 hours.
The product prepared in this example has the following characterization data:
1-Bz,1H NMR(400MHz,DMSO-d6,293K,ppm)δ7.37(s,6H),7.16(d,J＝8Hz,2H),6.83(d,J＝8Hz,2H),6.44(s,2H),6.09(s,2H),4.08–3.97(m,8H),3.87(s,6H),3.64(s,6H),3.59(s,6H),3.28(d,J＝16Hz,2H),1.38(t,J＝8Hz,6H)。
1-Cy,1H NMR(400MHz,DMSO-d6,293K,ppm)δ7.17(d,J＝8Hz,2H),6.83(d,J＝8Hz,2H),6.44(s,2H),6.09(s,2H),4.08–3.97(m,8H),3.87(s,6H),3.64(s,6H),3.59(s,6H),3.28(d,J＝16Hz,2H),1.38(t,J＝8Hz,6H)。
1h NMR results showed hetero [3]]The aromatic hydrocarbon crystal material adsorbed benzene at a stoichiometric ratio of 1:1, and did not adsorb cyclohexane.
The PXRD detection results are shown in fig. 1, where the PXRD pattern of the hetero [3] aromatic crystalline material after a period of standing in benzene vapor changes relative to the PXRD pattern of the initially activated hetero [3] aromatic crystalline material, indicating that its unit cell parameters have changed, meaning that benzene has been adsorbed into the hetero [3] aromatic crystalline material; the spectrum of the hetero [3] arene crystal material after being placed in cyclohexane vapor for a period of time has little change, which shows that the unit cell parameters of the hetero [3] arene crystal material have almost no change, and the hetero [3] arene crystal material has no adsorption capacity to cyclohexane.
Example 3
Adsorption of a 1:1 mixture of benzene and cyclohexane as hetero [3] aromatic crystalline materials: a20 mL strain bottle was taken, 0.5mL of benzene and 0.5mL of cyclohexane were added, which was named 1-Bz-Cy, 200mg of the hetero [3] aromatic hydrocarbon crystal material obtained in example 1 was placed in a 5mL open strain bottle, the open 5mL strain bottle was placed in the 20mL strain bottle, the 20mL strain bottle was sealed, the sealed strain bottle was placed in a 25 ℃ water bath for 40 hours, and the obtained powder was placed in a 50 ℃ vacuum oven for 30 minutes.
The product prepared in this example has the following characterization data:
1-Bz-Cy,1H NMR(400MHz,DMSO-d6,293K,ppm)δ7.37(s,6H),7.16(d,J＝8Hz,2H),6.83(d,J＝8Hz,2H),6.44(s,2H),6.09(s,2H),4.08–3.97(m,8H),3.87(s,6H),3.64(s,6H),3.59(s,6H),3.28(d,J＝16Hz,2H),1.38(t,J＝8Hz,6H)。
in that1The H NMR spectrum showed only signals from the hydrogen atoms corresponding to benzene, indicating hetero [3]]The aromatic hydrocarbon crystal material can selectively adsorb benzene.
The PXRD detection result is shown in fig. 1, and the PXRD pattern of the hetero [3] aromatic hydrocarbon crystal material after being left for a certain period of time in the mixed vapor of benzene and cyclohexane is changed relative to the PXRD pattern of the initially activated hetero [3] aromatic hydrocarbon crystal material, and the pattern change is the same as that of 1-Bz, which indicates that the hetero [3] aromatic hydrocarbon crystal material can selectively adsorb benzene.
The results of the headspace gas chromatography are shown in FIG. 2, and indicate that the hetero [3] arene crystalline material can selectively adsorb benzene with a selectivity of 97.54%.
Example 4
Regeneration of hetero [3] arene crystal material: 200mg of hetero [3] arene crystal material saturated and adsorbing benzene is heated in a vacuum oven at 100 ℃ for 2 hours, and a sample is marked as 1-D.
The product prepared in this example has the following characterization data:
1-D,1H NMR(400MHz,DMSO-d6,293K,ppm)δ7.17(d,J＝8Hz,2H),6.83(d,J＝8Hz,2H),6.43(s,2H),6.08(s,2H),4.08–3.97(m,8H),3.87(s,6H),3.64(s,6H),3.59(s,6H),3.28(d,J＝16Hz,2H),1.38(t,J＝8Hz,6H)。
in that1The signal of the hydrogen atom corresponding to benzene was found to have disappeared in the H NMR spectrum, indicating hetero [3]]The aromatic hydrocarbon crystal material has completed desorption regeneration, and benzene molecules have been completely released.
The PXRD detection result is shown in fig. 1, and compared with the PXRD spectrum of the initially activated hetero [3] arene crystal material, the PXRD spectrum of the hetero [3] arene crystal material after complete desorption has little change, which indicates that the hetero [3] arene crystal material has completed the desorption process and can be used for the next adsorption separation of benzene and cyclohexane.
Example 5
The hetero [3] arene crystal material is recycled: examples 3, 4 were repeated using 200mg of the regenerated hetero [3] arene crystalline material.
The results of the headspace gas chromatography are shown in FIG. 3, which shows that the hetero [3] arene crystal material can selectively adsorb benzene, the selectivity is as high as 97.54%, and the selectivity is not reduced after 10 times of repeated use.
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 (2)
1. A separation method of benzene and cyclohexane is characterized in that a benzene and cyclohexane mixture is adsorbed and separated by using a hetero [3] arene crystal material, wherein the chemical structural formula of the hetero [3] arene crystal material is as follows:
the hetero [3] arene crystal material is obtained by activation after recrystallization in a poor solvent, wherein the activation temperature is not lower than 150 ℃, and the activation time is not less than 2 hours;
the specific steps of adsorbing and separating the mixture of benzene and cyclohexane by using the hetero [3] arene crystal material are as follows: placing the hetero [3] arene crystal material in a mixed steam atmosphere of cyclohexane and benzene, wherein the temperature is lower than 80 ℃;
removing benzene and cyclohexane adsorbed on the surface of the impurity [3] aromatic hydrocarbon crystal material by adopting vacuum heating or reduced pressure heating, wherein the temperature of the vacuum heating or reduced pressure heating is less than 80 ℃;
and heating and desorbing the miscellaneous [3] arene crystal material to adsorb the complexed benzene, thereby realizing the regeneration of the miscellaneous [3] arene crystal material, wherein the heating temperature is 80-100 ℃.
2. The method for separating benzene and cyclohexane according to claim 1, wherein the poor solvent is acetone.
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| CN114181056B (en) * | 2021-11-10 | 2023-08-01 | 浙江大学杭州国际科创中心 | Cage arene, and preparation method and application thereof |
| CN115536486A (en) * | 2022-09-05 | 2022-12-30 | 北京理工大学 | High-selectivity separation method of benzene and cyclohexane |
| CN115651203B (en) * | 2022-10-27 | 2023-09-08 | 浙江大学杭州国际科创中心 | Supramolecular crystal framework material based on BN coordination bond and preparation method and application thereof |
| CN116354808B (en) * | 2023-03-13 | 2023-10-17 | 天津师范大学 | Separation method of cyclohexanone and cyclohexanol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5598122A (en) * | 1979-01-18 | 1980-07-25 | Toray Ind Inc | Separation of benzene by adsorption |
| CN1421271A (en) * | 2002-12-16 | 2003-06-04 | 中国科学院山西煤炭化学研究所 | Molecular sieve catalyst for synthesizing methanol into durene and its prepn and application |
| US8354019B2 (en) * | 2006-12-19 | 2013-01-15 | Instituto Mexicano Del Petroleo | Process for reducing benzene content of hydrocarbon stream using microporous carbon adsorbent |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5598122A (en) * | 1979-01-18 | 1980-07-25 | Toray Ind Inc | Separation of benzene by adsorption |
| CN1421271A (en) * | 2002-12-16 | 2003-06-04 | 中国科学院山西煤炭化学研究所 | Molecular sieve catalyst for synthesizing methanol into durene and its prepn and application |
| US8354019B2 (en) * | 2006-12-19 | 2013-01-15 | Instituto Mexicano Del Petroleo | Process for reducing benzene content of hydrocarbon stream using microporous carbon adsorbent |
Non-Patent Citations (3)
| Title |
|---|
| Harnessing Lewis acidic open metal sites of metal–organic frameworks: the foremost route to achieve highly selective benzene sorption over cyclohexane;Soumya Mukherjee et al.;《Chemical Communications》;20161231;第52卷(第53期);第8215-8218页 * |
| Selective Adsorption and Separation of Xylene Isomers and Benzene/Cyclohexane with Microporous Organic Polymers POP-1;Huiling Tan et al.;《Acs Applied Materials & Interfaces》;20180926;第10卷(第38期);第32717-32725页 * |
| The synthesis, structure, and molecular recognition properties of a [2]calix[1]biphenyl-type hybrid[3]arene;Jiong Zhou et al.;《Chemical Communications》;20161231;第52卷;第1622-1624页 * |
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