CN114605221B - Process for extracting acenaphthylene from coking rectification waste residue by using simulated moving bed - Google Patents
Process for extracting acenaphthylene from coking rectification waste residue by using simulated moving bed Download PDFInfo
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- CN114605221B CN114605221B CN202011426164.2A CN202011426164A CN114605221B CN 114605221 B CN114605221 B CN 114605221B CN 202011426164 A CN202011426164 A CN 202011426164A CN 114605221 B CN114605221 B CN 114605221B
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- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000004939 coking Methods 0.000 title claims abstract description 19
- 239000002699 waste material Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000009835 boiling Methods 0.000 claims abstract description 18
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims description 21
- 238000001914 filtration Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 13
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 239000000523 sample Substances 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 230000005526 G1 to G0 transition Effects 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000010413 mother solution Substances 0.000 claims 1
- 239000012488 sample solution Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 8
- 238000005516 engineering process Methods 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 6
- 238000007670 refining Methods 0.000 abstract description 6
- 238000001953 recrystallisation Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 description 9
- -1 methylene aromatic hydrocarbons Chemical class 0.000 description 8
- 238000006356 dehydrogenation reaction Methods 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 238000003912 environmental pollution Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 238000004237 preparative chromatography Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 1
- APSUAECGGVKVBU-UHFFFAOYSA-N 1-nitroacenaphthylene Chemical group C1=CC(C([N+](=O)[O-])=C2)=C3C2=CC=CC3=C1 APSUAECGGVKVBU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthalene Natural products C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003034 coal gas Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—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
- C07C7/00—Purification; Separation; Use of additives
- C07C7/14—Purification; Separation; Use of additives by crystallisation; Purification or separation of the crystals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/20—Acenaphthenes; Hydrogenated acenaphthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an extraction preparation process of acenaphthylene, which uses coking rectification waste residue as a raw material, uses a low boiling point solvent as a solvent for extraction, uses the low boiling point solvent for recrystallization, and uses a simulated moving bed preparation chromatography technology for refining to obtain acenaphthylene, wherein the purity is more than 97.0%, and the process has the characteristics of short preparation period, low cost, higher yield of each step and easy subsequent treatment, and is suitable for preparing the high-purity acenaphthylene.
Description
Technical Field
The invention relates to an extraction and preparation process of acenaphthylene, in particular to a process for extracting and refining acenaphthylene by taking coking rectification waste residue as a raw material.
Background
Acenaphthylene, english name ACENAPHTHYLENE, CAS number: 208-96-8, acenaphthylene can be used for preparing acenaphthylene resin, which is used for electric insulating materials, ion exchange resins and the like. Acenaphthylene is used as an organic synthesis raw material to produce 1, 8-naphthalene dicarboxylic anhydride, nitroacenaphthylene, acenaphthoquinone and the like which are used for preparing dyes, such as Vaseline scarlet and fluorescent whitening agents. The acenaphthylene can also be used for preparing pesticides such as plant growth hormone, insecticidal bactericide and the like.
Acenaphthylene has the structural formula:
the preparation method of acenaphthylene comprises the following steps:
One is the synthesis of acenaphthylene by the gas-phase oxidation of acenaphthylene. In 1951 paper ACENAPHTHYLENE of J.APPL. CHEM: its Polymers and Copolymers and Polymers and copolymers ofacenaphthylene (United STATES PATENT: 2445181) report methods for preparing acenaphthylene and acenaphthylene polymers and acenaphthylene copolymers; a preparation method of acenaphthylene is described in a paper published in 1972 in 05 of Liaoning chemical industry, namely, success of an acenaphthylene making test by utilizing acenaphthylene, and the method of preparing acenaphthylene by gasifying acenaphthylene through a catalyst under high temperature conditions and respectively carrying out catalytic dehydrogenation under air and steam conditions is described; in addition, patent "a method for preparing acenaphthylene and a reaction apparatus thereof" (application number: CN 200910054846.2) also reports a method for producing acenaphthylene by gasifying acenaphthylene through a catalyst and catalytically dehydrogenating acenaphthylene in a carbon dioxide atmosphere.
The other is a process for preparing acenaphthylene by a rectification extraction method. In 2018, the technology for preparing acenaphthylene by a rectification extraction method is reported in an invention patent device and method for extracting acenaphthylene and acenaphthylene in LCO (liquid Crystal on gas) double-ring aromatic hydrocarbon (patent number: CN201811485681. X) disclosed in Gu Zhenggui, cao Xiaoyan and Ling Hong of Nanjing university.
The third is acenaphthene bromination and elimination dehydrogenation. In 1999, a paper published by the university of mining Jiang Qun, study of dehydrogenation of methylene aromatic hydrocarbons, reports the dehydrogenation of various methylene aromatic hydrocarbons in the presence of N-bromosuccinimide (NBS). The method can be used for preparing acenaphthylene by dehydrogenating acenaphthylene.
The fourth is the method of bromoaddition and re-elimination of acenaphthylene. In 2005, it was described that, in "a process for producing a polycyclic aromatic vinyl compound" of the new japanese iron chemical company, tai Tian Daogui and the bamboo-inner-brown tree (patent No. CN 200510008106.7), an addition agent such as halogen, hydrogen halide, water or the like is added to a vinyl group of a polycyclic aromatic vinyl compound such as divinylbenzene, divinylbiphenyl or acenaphthylene to form a corresponding polycyclic aromatic vinyl compound derivative, and then the polycyclic aromatic vinyl compound derivative is separated and purified by recrystallization, adsorption or chemical reaction, and then the addition agent added to the polycyclic aromatic vinyl compound derivative is removed to obtain a high-purity polycyclic aromatic vinyl compound. The method for extracting and refining acenaphthylene in coking rectification waste residues has not been reported yet.
The above methods have the advantages of readily available raw materials, few preparation steps, and industrial feasibility, but have some drawbacks. The method 1 prepares acenaphthylene by catalytic dehydrogenation at the high temperature of about 600 ℃, and has the problems of high energy consumption and large environmental pollution; the method 2 has the problems of high energy consumption and complex process; the method 3 uses N-bromosuccinimide (NBS) to bromize and then eliminate the dehydrogenation, the cost of the N-bromosuccinimide (NBS) is high, and the problem of environmental pollution of bromide exists; in method 4, the bromine addition and elimination method such as bromine water is used, and there is a problem of environmental pollution of bromide as in method 3. Therefore, there is a need to try a new process for preparing acenaphthylene that is simple, low cost and environmentally friendly.
Disclosure of Invention
The invention aims to utilize coking rectification waste residues, solve the problem of environmental pollution, and simultaneously provide an acenaphthylene extraction and refining method which has the advantages of simple process, low cost and environmental friendliness.
Coking rectifying waste residue is an environmentally polluting solid waste known in the art and is also known as coking waste residue. Is waste residue generated in the process of producing coke, coal gas and other chemical products through a coking process or a coking rectification process. Which contain various harmful solid, semisolid, oily substances, volatile components, etc. The main sources are industrial enterprises such as coking plants. See, for example: wei Songbo, etc., and the comprehensive utilization of waste residues of the coking production process, the Wu Steel technology, volume 44, page 1, page 6-8 in 2006.
As a result of diligent studies on the above problems, the present inventors have unexpectedly found that acenaphthylene is produced using simulated moving bed preparation chromatography, and completed the present invention. The present invention includes the following aspects.
The invention relates to a refining method of acenaphthylene, which takes coking rectification waste residue as a raw material, adopts solvent extraction, recrystallization and low boiling point solvent as solvent extraction, then uses the low boiling point solvent for recrystallization, and then applies simulated moving bed preparation chromatography technology for refining to obtain acenaphthylene with purity more than 97.0%, and comprises the following steps:
1) Mixing the coking rectification waste residue (100 g) with a low-boiling point solvent (400 ml), heating to the boiling point temperature of the low-boiling point solvent, stirring for 1h, filtering, cooling the filtered mother liquor for 2h, and filtering to obtain extract solid (30 g);
2) Mixing the extract solids (30 g) with a low boiling point solvent (90 ml), heating to the boiling point temperature of the low boiling point solvent, stirring for 1h, cooling for 2h, and filtering to obtain crude product solids (5 g);
3) Dissolving the crude product solid in n-hexane-acetone (volume ratio 100:1) to prepare a 3.0% sample solvent solution, separating by using simulated moving bed preparation chromatography, concentrating and evaporating the fraction from the simulated moving bed preparation chromatography system to obtain acenaphthylene with purity of more than 97.0%;
the low boiling point solvent is one or more of methanol, ethanol, isopropanol, n-hexane, petroleum ether, ethyl acetate and tetrahydrofuran; preferably one or more of n-hexane, petroleum ether or ethyl acetate.
The simulated moving bed chromatographic conditions are as follows: silica gel is used as a stationary phase, n-hexane-acetone (volume ratio of 100:1) solution is used as a mobile phase, the flow rate of a sample injection is (0.3 ml/min-0.5 ml/min), the flow rate of an eluent is (15.0 ml/min-20.0 ml/min), the flow rate of an outlet of an extract, namely acenaphthylene product, is (1.2 ml/min-1.5 ml/min), and the flow rate of a residual solution is (15.0 ml/min-20.0 ml/min).
The inventor of the present invention has unexpectedly found that, by using simulated moving bed preparative chromatography in step 3) and n-hexane-acetone as the mobile phase, purification of acenaphthylene can be well achieved, and the purity of acenaphthylene product after purification reaches over 97.0%.
For the above work, firstly, it is not obvious to the person skilled in the art that the simulated moving bed preparative chromatography purification technique is adopted in the purification method of acenaphthylene, since the simulated moving bed preparative chromatography purification technique is not taught in the prior art; 2. according to general knowledge, the mobile phase solvent system selected by the simulated moving bed preparation chromatography technology adopts a methanol-water flow phase system, and does not adopt an n-hexane-acetone mobile phase system, so that the n-hexane-acetone mobile phase system is adopted as a purification system under the teaching, and the improvement of the product purity is not obvious to a person skilled in the art; 3. when the purification technology system of the invention is used, the cost of raw materials is low, the separation process is simple, the requirements of industrial production can be met in the aspects of economy and environmental protection, and compared with the prior art, the purification technology system has obvious progress.
Brief description of the drawings
FIG. 1 is a liquid chromatograph of acenaphthylene purity. The spectrum was determined using the product obtained in example 1, confirming that the purity of the product prepared according to the invention is greater than 97.0%.
Best mode for carrying out the invention
The conditions for liquid chromatography of acenaphthylene prepared according to the present invention are as follows.
The invention adopts an Agilent 1100 liquid chromatograph and an ultraviolet spectrum detector.
The operating conditions for liquid chromatography were as follows:
Chromatographic column: XDB-C18
Column temperature: 40 DEG C
Mobile phase: methanol-water (80:20)
Detection wavelength: 254
Sample preparation: 10mg of sample was dissolved in 10ml of methanol
The reagents used in the examples of the present invention were as follows:
TABLE 1 raw materials and reagents
Example 1
1) Mixing the coking rectification waste residue (100 g) with petroleum ether (400 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, filtering, cooling the mother liquor obtained by filtering for 2h, and filtering to obtain extract solid (30 g);
2) Mixing the extract solid (30 g) with petroleum ether (90 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, cooling for 2h, and filtering to obtain crude product solid (5 g);
3) Dissolving the crude product solid in n-hexane-acetone (volume ratio 100:1) to prepare a 3.0% sample solvent solution, and separating by using simulated moving bed preparation chromatography under the following conditions: silica gel is used as a stationary phase, n-hexane-acetone (volume ratio of 100:1) solution is used as a mobile phase, the flow rate of a sample injection is 0.3ml/min, the flow rate of an eluent is 16.0ml/min, the flow rate of an outlet of an extract, namely acenaphthylene product, is 1.2ml/min, and the flow rate of a residual solution is 15.0 ml/min. Concentrating and evaporating the fraction from the simulated moving bed preparation chromatographic system to obtain acenaphthylene with the purity of 98.8%;
Example 2
1) Mixing the coking rectification waste residue (100 g) with petroleum ether (400 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, filtering, cooling the mother liquor obtained by filtering for 2h, and filtering to obtain extract solid (30 g);
2) Mixing the extract solid (30 g) with petroleum ether (90 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, cooling for 2h, and filtering to obtain crude product solid (5 g);
3) Dissolving the crude product solid in n-hexane-acetone (volume ratio 100:1) to prepare a 3.0% sample solvent solution, and separating by using simulated moving bed preparation chromatography under the following conditions: silica gel is used as a stationary phase, n-hexane-acetone (volume ratio of 100:1) solution is used as a mobile phase, the flow rate of a sample injection is 0.5ml/min, the flow rate of an eluent is 18.0ml/min, the flow rate of an outlet of an extract, namely acenaphthylene product, is 1.5ml/min, and the flow rate of a residual solution is 17.0 ml/min. Concentrating and evaporating fractions from the simulated moving bed preparation chromatographic system to obtain acenaphthylene with the purity of 97.2%;
Comparative example 1
1) Mixing the coking rectification waste residue (100 g) with petroleum ether (400 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, filtering, cooling the mother liquor obtained by filtering for 2h, and filtering to obtain extract solid (30 g);
2) Mixing the extract solid (30 g) with petroleum ether (90 ml) at 60-90 ℃, heating to 60 ℃, stirring for 1h, cooling for 2h, and filtering to obtain crude product solid (5 g);
3) Dissolving the crude product solid in n-hexane-isopropanol (volume ratio 100:1) to prepare a 3.0% sample solvent solution, and separating by using simulated moving bed preparation chromatography under the following conditions: silica gel is used as a stationary phase, n-hexane-isopropanol (volume ratio 100:1) solution is used as a mobile phase, the flow rate of a sample injection is 0.3ml/min, the flow rate of an eluent is 16.0ml/min, the flow rate of an outlet of an extract, namely acenaphthylene product, is 1.2ml/min, and the flow rate of a residual solution is 15.0 ml/min. Concentrating and evaporating the fraction from the simulated moving bed preparation chromatographic system to obtain acenaphthylene with the purity of 92.8%.
Firstly, the person skilled in the art never uses coking rectification waste residue as a raw material to prepare acenaphthylene, which is one of the important invention cores of the patent; and there is no report on the adoption of simulated moving bed preparation chromatography as a means for preparing and purifying acenaphthylene. In addition, it can be seen from the above examples and comparative examples that the excellent performance of the n-hexane-acetone system as a mobile phase of simulated moving bed preparative chromatography in terms of product purification is not foreseeable by the person skilled in the art without inventive effort.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention. Furthermore, the present invention includes, in addition to the above-described embodiments, combinations of the technical features in the above-described embodiments, since those skilled in the art can directly and unambiguously determine that the technical features mentioned in the present invention can solve the relevant technical problems after appropriately combining them after reading the present invention.
Claims (3)
1. The preparation process of acenaphthylene is characterized by comprising the following steps of:
1) Mixing the coking rectification waste residue with a low-boiling point solvent, heating to the boiling point temperature of the low-boiling point solvent, stirring, filtering, cooling the mother solution obtained by filtering, and filtering to obtain extract solid;
2) Mixing the extract solid with a low boiling point solvent, heating to the boiling point temperature of the low boiling point solvent, stirring, cooling, and filtering to obtain a crude product solid;
3) Dissolving the crude product solid in n-hexane-acetone to prepare a sample solution, separating by using a simulated moving bed preparation chromatograph, concentrating and evaporating the fraction separated by the simulated moving bed preparation chromatograph system to obtain acenaphthylene with the purity of more than 97.0%;
The low boiling point solvent is one or more of methanol, ethanol, isopropanol, n-hexane, petroleum ether, ethyl acetate and tetrahydrofuran.
2. A process for the preparation of acenaphthylene according to claim 1, wherein in step 3), the simulated moving bed chromatography conditions are: silica gel is used as a stationary phase, n-hexane-acetone solution with the volume ratio of 100:1 is used as a mobile phase, the flow rate of a sample injection is 0.3 ml/min-0.5 ml/min, the flow rate of an eluent is 15.0 ml/min-20.0 ml/min, the flow rate of an outlet of an extract, namely acenaphthylene product, is 1.2 ml/min-1.5 ml/min, and the flow rate of a residual liquid is 15.0 ml/min-20.0 ml/min.
3. Use of coked rectifying waste residue for manufacturing acenaphthylene, characterized in that acenaphthylene is manufactured by the method of any one of claims 1-2.
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| CN101955407A (en) * | 2009-07-15 | 2011-01-26 | 华东理工大学 | Preparation method and reaction device of acenaphthylene |
| CN102898269A (en) * | 2012-10-17 | 2013-01-30 | 张家滔 | Supercritical extraction method for acenaphthene, fluorene and dibenzofuran in coal tar wash oil fraction |
| CN203265235U (en) * | 2012-11-01 | 2013-11-06 | 柳州钢铁股份有限公司 | Coking waste residue resource utilization apparatus |
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| CN101955407A (en) * | 2009-07-15 | 2011-01-26 | 华东理工大学 | Preparation method and reaction device of acenaphthylene |
| CN102898269A (en) * | 2012-10-17 | 2013-01-30 | 张家滔 | Supercritical extraction method for acenaphthene, fluorene and dibenzofuran in coal tar wash oil fraction |
| CN203265235U (en) * | 2012-11-01 | 2013-11-06 | 柳州钢铁股份有限公司 | Coking waste residue resource utilization apparatus |
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| 探析焦化生产工艺废渣的综合利用;郝小娟;《化工管理》;第20卷;第241页 * |
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