CN104387224A - Process for separating ethylbenzene from carbon octa-aromatic hydrocarbon - Google Patents
Process for separating ethylbenzene from carbon octa-aromatic hydrocarbon Download PDFInfo
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- CN104387224A CN104387224A CN201410603099.4A CN201410603099A CN104387224A CN 104387224 A CN104387224 A CN 104387224A CN 201410603099 A CN201410603099 A CN 201410603099A CN 104387224 A CN104387224 A CN 104387224A
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- tower
- ethylbenzene
- xylol
- extractive distillation
- xylene
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 title abstract 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000000895 extractive distillation Methods 0.000 claims abstract description 31
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 238000000605 extraction Methods 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000011084 recovery Methods 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 4
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 4
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- -1 phenyl aldehyde Chemical class 0.000 claims description 4
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
- 229940093471 ethyl oleate Drugs 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 6
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract 2
- 229940078552 o-xylene Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 238000004821 distillation Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- 230000035800 maturation Effects 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
- 229920000728 polyester Polymers 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process for separating ethylbenzene from carbon octa-arene. The C-octa aromatic hydrocarbon mixture is firstly separated by a rectifying tower (B1), o-xylene is distilled from the bottom of the tower, and the distillate at the top of the tower enters an extractive rectifying tower (B2) for separation; ethylbenzene flows out of the top of the extractive distillation tower (B2), distillate at the bottom of the extractive distillation tower enters an extractant recovery tower (B3) for separation, and a mixture of p-xylene and m-xylene is distilled out of the top of the extractive distillation tower; the extractant distilled from the bottom enters an extraction rectifying tower (B2) for recycling. Compared with a precise rectification method, the method has the advantages of obviously reduced number of tower plates, reduced energy consumption, obvious separation effect, over 99 percent of ethylbenzene purity, easy recovery of an extracting agent and recycling.
Description
Technical field
The present invention relates to a kind of chemical separating technique, particularly relate to a kind of technique being separated ethylbenzene from C8 aronmatic.
Background technology
Industrial xylol is mainly derived from catalytic reforming, steam cracking, toluene disproportionation and coal tar.Xylol is mainly used as the blending compound of solvent and gasoline, and resource utilization is not high, and added value is low.And high-purity C8 aronmatic is only the main body of synthetic rubber and the market requirement such as resin, fine chemistry industry.
As important industrial chemicals, p-Xylol (PX), o-Xylol (OX) are mainly used as synthesizing polyester and phthalic anhydride, m-xylene (MX) is through ammonia oxidation, m-dicyanobenzene processed, it is the important intermediate of synthesis Special Resin, higher effective and lower toxic pesticide, fuel and softening agent, ethylbenzene (EB) also has purposes quite widely, mainly for the production of vinylbenzene, and then produces styrene homopolymers and take vinylbenzene as the multipolymer of main component.
EB all containing some amount in xylol material, by the analysis to aromatic hydrocarbons material properties, finds that the relative volatility between them, close to 1, is difficult to be separated by general conventional distillation technology because EB and MX and PX structure, character are similar.The method separated from C8 aronmatic by ethylbenzene studied both at home and abroad is at present a lot, mainly contains: precise distillation method and adsorption method of separation.Its basic technology of precise distillation method is two-tower process, and xylol enters the first tower, and tower reactor sloughs o-Xylol, and purity is 98%, and overhead product is ethylbenzene, to, m-xylene.This tower is 110-120 block column plate altogether, reflux ratio R=14-18.First tower overhead enters the second tower, and overhead product is the ethylbenzene of 99.5-99.7%.This tower needs 360 blocks of column plates, reflux ratio R=90-100.The advantage of precise distillation method is technology maturation, and shortcoming is that energy consumption is high.Adsorption method of separation is divided into Preferential adsorption xylene isomerization body technique and Preferential adsorption ethylbenzene technology, and its advantage is that product purity is high, but shortcoming needs in producing to use expensive particular molecule to sieve as sorbent material, and production operation is complicated.EB is converted into dimethylbenzene by industrial usual employing isomerization method, but the transformation efficiency of the method EB is lower, generate a large amount of by product, and operational condition is harsher.
Summary of the invention
The object of the invention is to provide a kind of technique being separated ethylbenzene from C8 aronmatic to solve problems of the prior art; This technique improves separation efficiency, reduces energy consumption.
Technical scheme of the present invention is: a kind of technique being separated ethylbenzene from C8 aronmatic, and have rectifying tower (B1), extractive distillation column (B2), extraction agent recovery tower (B3) in whole technical process, its concrete steps are as follows:
(1), be first separated C8 aronmatic mixed solution through rectifying tower (B1), distillate at the bottom of tower is o-Xylol, and overhead distillate is ethylbenzene, p-Xylol and m-xylene mixed solution;
(2), rectifying tower (B1) overhead distillate enter extractive distillation column (B2) be separated, overhead distillate is ethylbenzene, and distillate at the bottom of tower is p-Xylol, m-xylene and extraction agent mixed solution;
(3), distillate at the bottom of extractive distillation column (B2) tower enters extraction agent recovery tower (B3) and is separated, and overhead distillate is m-xylene and p-Xylol mixture; Distillate at the bottom of tower is extraction agent, returns extractive distillation column (B2) and recycles.
The extraction agent used in preferred extractive distillation column B2 is phenyl aldehyde, one in diisobutyl ketone, valerone, aniline, Cyclohexamide, ethyl benzoate, methyl phenylacetate, Phenylacetic acid ethylester, Witconol 2301 or ethyl oleate.
The mixed solution mass ratio of the consumption of preferred extraction agent and rectifying tower (B1) overhead distillate ethylbenzene, p-Xylol/m-xylene is 0.5-2:1.
The stage number 80-200 of preferred rectifying tower (B1); Trim the top of column compares 8-38.The stage number of preferred extractive distillation column (B2) is 240-350; Trim the top of column is than being 35-65.The stage number of preferred extraction agent recovery tower (B3) is 12-25; The reflux ratio of tower top is 0.6-3.5; Working pressure 5-50kPa.
Beneficial effect:
(1) this invention is compared with precise distillation method, and stage number obviously reduces, and energy consumption reduces.
(2) this invention separating effect is remarkable, and ethylbenzene purity can reach more than 99%.
(3) extracting rectifying that adopts of this invention, extraction agent is easy to reclaim, recycle.
Accompanying drawing explanation
Fig. 1 is the schematic flow sheet being separated ethylbenzene process from C8 aronmatic of the present invention; Wherein B1 rectifying tower, B2 extractive distillation column, B3 extraction agent recovery tower, B4 mixing tank; FEED-C8 aronmatic mixture; W1-o-Xylol product; D1-ethylbenzene, m-xylene and p-Xylol mixture; D2-ethylbenzene product; W2-p-Xylol, m-xylene and extraction agent mixed solution; D3-m-xylene/p-Xylol miscellany; The agent of W3-cycling extraction; MAKEUP-compensates extraction agent; SOLVENT-extraction agent.
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
As shown in Figure 1: C8 aronmatic mixture 40000kg/h is (containing ethylbenzene 6000kg/h, o-Xylol 8000kg/h, m-xylene 18000kg/h, p-Xylol 8000kg/h) enter rectifying tower (B1), this tower stage number 200, reflux ratio 8, obtains the o-Xylol that 7920kg/h quality purity is 99.00% at the bottom of tower, tower top is ethylbenzene and m-xylene, the p-Xylol mixture of 32080kg/h.Rectifying tower (B1) overhead product enters extractive distillation column (B2) and is separated, introduce extraction agent Phenylacetic acid ethylester (32080kg/h) at extractive distillation column (B2) through mixing tank (B4) simultaneously, this tower stage number 255, reflux ratio 61, tower top obtains the ethylbenzene that 5940kg/h quality purity is 99.23%, is Phenylacetic acid ethylester and m-xylene, the p-Xylol mixture of 58220kg/h at the bottom of tower.Extractive distillation column (B2) the bottomsstream enters extraction agent recovery tower (B3), this tower stage number 15, reflux ratio 0.9, tower pressure 25kPa, tower top obtains m-xylene/p-Xylol mixture that 26167kg/h quality purity is 99.46%, and bottom product enters extractive distillation column (B2) and recycles.
Embodiment 2
C8 aronmatic mixture 50000kg/h is (containing ethylbenzene 7500kg/h, o-Xylol 10000kg/h, m-xylene 22500kg/h, p-Xylol 10000kg/h) enter rectifying tower (B1), this stage number 120, reflux ratio 11, obtains the o-Xylol that 9920kg/h quality purity is 99.20% at the bottom of tower, tower top is ethylbenzene and m-xylene, the p-Xylol mixture of 40080kg/h.Rectifying tower (B1) overhead product enters extractive distillation column (B2) and is separated, introduce extraction agent Witconol 2301 (23358kg/h) at extractive distillation column (B2) simultaneously, this tower stage number 255, reflux ratio 59, tower top obtains the ethylbenzene that 7437kg/h quality purity is 99.12%, is Propiophenone and m-xylene, the p-Xylol mixture of 56001kg/h at the bottom of tower.Extractive distillation column (B2) the bottomsstream enters extraction agent recovery tower (B3), this tower stage number 16, reflux ratio 0.7, tower pressure 5kPa, tower top obtains m-xylene/p-Xylol mixture that 32356kg/h quality purity is 99.54%, and bottom product enters extractive distillation column (B2) and recycles.
Embodiment 3
C8 aronmatic mixture 45000kg/h is (containing ethylbenzene 6750kg/h, o-Xylol 9000kg/h, m-xylene 20250kg/h, p-Xylol 9000kg/h) enter rectifying tower (B1), this tower stage number 120, reflux ratio 13, obtains the o-Xylol that 9000kg/h quality purity is 99.49% at the bottom of tower, tower top is ethylbenzene and m-xylene, the p-Xylol mixture of 36000kg/h.Rectifying tower (B1) overhead product enters extractive distillation column (B2) and is separated, introduce extraction agent phenyl aldehyde (72000kg/h) at extractive distillation column (B2) simultaneously, this tower stage number 240, reflux ratio 65, tower top obtains the ethylbenzene that 6691kg/h quality purity is 99.91%, is phenyl aldehyde and m-xylene, the p-Xylol mixture of 101309kg/h at the bottom of tower.Extractive distillation column (B2) the bottomsstream enters extraction agent recovery tower (B3), this tower stage number 25, reflux ratio 0.6, tower pressure 20kPa, the quality purity that tower top obtains 29343kg/h is the m-xylene/p-Xylol mixture of 99.36%, and bottom product enters extractive distillation column (B2) and recycles.
Embodiment 4
C8 aronmatic mixture 40000kg/h is (containing ethylbenzene 8000kg/h, o-Xylol 8000kg/h, m-xylene 18000kg/h, p-Xylol 6000kg/h) enter rectifying tower (B1), this tower stage number 80, reflux ratio 38, obtains the o-Xylol that 7924kg/h quality purity is 98.98% at the bottom of tower, tower top is ethylbenzene and m-xylene, the p-Xylol mixture of 32076kg/h.Rectifying tower (B1) overhead product enters extractive distillation column (B2) and is separated, introduce extraction agent aniline (16038kg/h) at extractive distillation column (B2) simultaneously, this tower stage number 350, reflux ratio 35, tower top obtains the ethylbenzene that 7979kg/h quality purity is 99.67%, is aniline and m-xylene, the p-Xylol mixture of 40136kg/h at the bottom of tower.Extractive distillation column (B2) the bottomsstream enters extraction agent recovery tower (B3), this tower stage number 12, reflux ratio 3.5, tower pressure 50kPa, the quality purity that tower top obtains 23921kg/h is the m-xylene/p-Xylol mixture of 99.43%, and bottom product and the extraction agent supplemented enter extractive distillation column (B2) and recycle.
Claims (6)
1. from C8 aronmatic, be separated a technique for ethylbenzene, its concrete steps are as follows:
(1), be first separated C8 aronmatic mixed solution through rectifying tower B1, distillate at the bottom of tower is o-Xylol, and overhead distillate is ethylbenzene, p-Xylol and m-xylene mixed solution;
(2), rectifying tower B1 overhead distillate enters extractive distillation column B2 and is separated, and overhead distillate is ethylbenzene, and distillate at the bottom of tower is p-Xylol, m-xylene and extraction agent mixed solution;
(3), distillate at the bottom of extractive distillation column B2 tower enters extraction agent recovery tower B3 and is separated, and overhead distillate is m-xylene and p-Xylol mixture; Distillate at the bottom of tower is extraction agent, returns extractive distillation column B2 and recycles.
2. technique according to claim 1, the extraction agent that it is characterized in that using in extractive distillation column B2 is phenyl aldehyde, one in diisobutyl ketone, valerone, aniline, Cyclohexamide, ethyl benzoate, methyl phenylacetate, Phenylacetic acid ethylester, Witconol 2301 or ethyl oleate.
3. technique according to claim 1, is characterized in that: the mass ratio of described extracting rectifying extraction agent quality and rectifying tower B1 overhead distillate is 0.5-2:1.
4. technique according to claim 1, is characterized in that: the stage number 80-200 of described rectifying tower B1; Trim the top of column compares 8-38.
5. technique according to claim 1, is characterized in that: the stage number of described extractive distillation column B2 is 240-350; Trim the top of column is than being 35-65.
6. technique according to claim 1, is characterized in that: the stage number of described extraction agent recovery tower B3 is 12-25; The reflux ratio of tower top is 0.6-3.5; Working pressure 5-50kPa.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020018875A1 (en) * | 2018-07-20 | 2020-01-23 | Scg Chemicals Co., Ltd. | Integrated processes for para-xylene production |
CN113457193A (en) * | 2021-06-25 | 2021-10-01 | 济南大学 | Device and method for separating methanol-methylal-methyl formate mixture |
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US3105017A (en) * | 1960-06-22 | 1963-09-24 | Exxon Research Engineering Co | Extractive distillation of ethylbenzene |
KR20130060532A (en) * | 2011-11-30 | 2013-06-10 | 롯데케미칼 주식회사 | Method for high purity selective seperation ethylbenzene from mixed xylene with extracting distillation |
-
2014
- 2014-10-30 CN CN201410603099.4A patent/CN104387224A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US3105017A (en) * | 1960-06-22 | 1963-09-24 | Exxon Research Engineering Co | Extractive distillation of ethylbenzene |
KR20130060532A (en) * | 2011-11-30 | 2013-06-10 | 롯데케미칼 주식회사 | Method for high purity selective seperation ethylbenzene from mixed xylene with extracting distillation |
Non-Patent Citations (2)
Title |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020018875A1 (en) * | 2018-07-20 | 2020-01-23 | Scg Chemicals Co., Ltd. | Integrated processes for para-xylene production |
US10975006B2 (en) | 2018-07-20 | 2021-04-13 | Scg Chemicals Co., Ltd. | Integrated processes for para-xylene production |
CN112771013A (en) * | 2018-07-20 | 2021-05-07 | Scg化学有限公司 | Integrated process for para-xylene production |
CN112771013B (en) * | 2018-07-20 | 2024-05-28 | Scg化学有限公司 | Integrated process for para-xylene production |
CN113457193A (en) * | 2021-06-25 | 2021-10-01 | 济南大学 | Device and method for separating methanol-methylal-methyl formate mixture |
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