KR102773808B1 - 유사 이동층 단계, 및 2 섹션 칼럼에서 2개의 분획을 분별하는 단계를 사용하여 파라자일렌을 제조하는 방법 - Google Patents
유사 이동층 단계, 및 2 섹션 칼럼에서 2개의 분획을 분별하는 단계를 사용하여 파라자일렌을 제조하는 방법 Download PDFInfo
- Publication number
- KR102773808B1 KR102773808B1 KR1020207036182A KR20207036182A KR102773808B1 KR 102773808 B1 KR102773808 B1 KR 102773808B1 KR 1020207036182 A KR1020207036182 A KR 1020207036182A KR 20207036182 A KR20207036182 A KR 20207036182A KR 102773808 B1 KR102773808 B1 KR 102773808B1
- Authority
- KR
- South Korea
- Prior art keywords
- desorbent
- fraction
- paraxylene
- fractions
- raffinate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 124
- 238000004519 manufacturing process Methods 0.000 title description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 80
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 76
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 38
- 238000000926 separation method Methods 0.000 claims abstract description 37
- 238000004821 distillation Methods 0.000 claims abstract description 31
- 239000008096 xylene Substances 0.000 claims abstract description 29
- 238000002347 injection Methods 0.000 claims abstract description 24
- 239000007924 injection Substances 0.000 claims abstract description 24
- 239000003463 adsorbent Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 239000010457 zeolite Substances 0.000 claims abstract description 16
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 15
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 22
- 238000005194 fractionation Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 description 23
- 239000012071 phase Substances 0.000 description 9
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011734 sodium 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
- 239000002904 solvent Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- QUGUFLJIAFISSW-UHFFFAOYSA-N 1,4-difluorobenzene Chemical compound FC1=CC=C(F)C=C1 QUGUFLJIAFISSW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/1828—Simulated moving beds characterised by process features
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/185—Simulated moving beds characterised by the components to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/08—Xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
-
- 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
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- 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
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1856049 | 2018-06-29 | ||
| FR1856049A FR3083231B1 (fr) | 2018-06-29 | 2018-06-29 | Procede de production de paraxylene utilisant une etape en lit mobile simule, et une etape de fractionnement de deux fractions |
| PCT/EP2019/066445 WO2020002142A1 (fr) | 2018-06-29 | 2019-06-21 | Procede de production de paraxylene utilisant une etape en lit mobile simule, et une etape de fractionnement de deux fractions dans une colonnes de 2 coupes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20210030273A KR20210030273A (ko) | 2021-03-17 |
| KR102773808B1 true KR102773808B1 (ko) | 2025-02-26 |
Family
ID=63312144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207036182A Active KR102773808B1 (ko) | 2018-06-29 | 2019-06-21 | 유사 이동층 단계, 및 2 섹션 칼럼에서 2개의 분획을 분별하는 단계를 사용하여 파라자일렌을 제조하는 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11242302B2 (enExample) |
| EP (1) | EP3814307B1 (enExample) |
| JP (1) | JP7361057B2 (enExample) |
| KR (1) | KR102773808B1 (enExample) |
| CN (1) | CN112585107B (enExample) |
| FR (1) | FR3083231B1 (enExample) |
| PT (1) | PT3814307T (enExample) |
| WO (1) | WO2020002142A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021173238A1 (en) * | 2020-02-27 | 2021-09-02 | Exxonmobil Chemical Patents Inc. | Xylene separation processes using a membrane separator |
| CN112843788B (zh) * | 2021-01-19 | 2022-10-28 | 温州大学新材料与产业技术研究院 | 一种采用流动相独立环外置换的温度梯度模拟移动床装置及其分离方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700744A (en) * | 1970-09-18 | 1972-10-24 | Universal Oil Prod Co | Simultaneous recovery and production of pure xylenes from a c aromatic mixture |
| TW200454B (enExample) * | 1991-09-05 | 1993-02-21 | Inst Of France Petroleum | |
| FR2773149B1 (fr) * | 1997-12-26 | 2000-02-18 | Inst Francais Du Petrole | Procede de coproduction et de separation d'ethylbenzene et de paraxylene |
| US6573418B2 (en) * | 2000-07-10 | 2003-06-03 | Bp Corporation North America Inc. | Process for production of para-xylene incorporating pressure swing adsorption and simulated moving bed adsorption |
| US6627783B2 (en) * | 2000-07-10 | 2003-09-30 | Bp Corporation North America Inc. | Pressure swing adsorption process for separating para-xylene and ethylbenzene from mixed C8 aromatics |
| TWI240716B (en) * | 2000-07-10 | 2005-10-01 | Bp Corp North America Inc | Pressure swing adsorption process for separating paraxylene and ethylbenzene from mixed C8 aromatics |
| US6483002B1 (en) * | 2000-09-26 | 2002-11-19 | Uop Llc | Integrated fractional distillation for adsorptive separation process |
| FR2844790B1 (fr) * | 2002-09-20 | 2004-10-22 | Inst Francais Du Petrole | Procede de coproduction de paraxylene et de styrene |
| FR2862638B1 (fr) | 2003-11-26 | 2005-12-30 | Inst Francais Du Petrole | Procede de production de paraxylene comprenant une etape d'adsorption et deux etapes d'isomerisation |
| US7553998B2 (en) * | 2006-06-21 | 2009-06-30 | Uop Llc | Energy-efficient process for para-xylene production |
| FR2922547B1 (fr) * | 2007-10-18 | 2012-09-21 | Inst Francais Du Petrole | Procede de separation d'aromatiques en c8 avec recyclage limite |
| US8557028B2 (en) * | 2011-03-31 | 2013-10-15 | Uop Llc | Binderless zeolitic adsorbents, methods for producing binderless zeolitic adsorbents, and adsorptive separation processes using the binderless zeolitic adsorbents |
| US8802914B2 (en) * | 2011-12-15 | 2014-08-12 | Uop Llc | Process and apparatus for para-xylene production using multiple adsorptive separation units and a split fractionating column |
| CN103373891B (zh) * | 2012-04-26 | 2015-07-29 | 中国石油化工股份有限公司 | 从c8芳烃中吸附分离生产对二甲苯和乙苯的方法 |
| FR3002461B1 (fr) * | 2013-02-22 | 2016-12-09 | Ifp Energies Now | Procede de separation des xylenes en lit mobile simule au moyen d'un solide adsorbant zeolithique de granulometrie comprise entre 150 et 500 microns |
| FR3010911B1 (fr) * | 2013-09-20 | 2017-06-09 | Ifp Energies Now | Procede de separation des xylenes par contre courant simule traitant une charge contenant des impuretes oxygenees aromatiques de type phenols |
| FR3023841B1 (fr) * | 2014-07-18 | 2016-07-15 | Ifp Energies Now | Procede de production de paraxylene comprenant deux unites de separation en lit mobile simule et deux unites d'isomerisation dont l'une en phase gaz |
| KR101920578B1 (ko) * | 2014-08-15 | 2018-11-20 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 방향족 화합물의 제조 방법 |
| US10093598B2 (en) * | 2015-02-19 | 2018-10-09 | Exxonmobil Chemical Patents Inc. | Xylene separation process |
| JP6527960B2 (ja) * | 2015-04-30 | 2019-06-12 | エクソンモービル・ケミカル・パテンツ・インク | パラキシレンを製造するプロセスおよび装置 |
| FR3083230B1 (fr) * | 2018-06-29 | 2021-04-23 | Axens | Procede de production de paraxylene utilisant une etape en lit mobile simule, et une etape de fractionnement via une colonne de 3 coupes |
-
2018
- 2018-06-29 FR FR1856049A patent/FR3083231B1/fr not_active Expired - Fee Related
-
2019
- 2019-06-21 WO PCT/EP2019/066445 patent/WO2020002142A1/fr not_active Ceased
- 2019-06-21 CN CN201980043987.6A patent/CN112585107B/zh active Active
- 2019-06-21 PT PT197312994T patent/PT3814307T/pt unknown
- 2019-06-21 JP JP2020572983A patent/JP7361057B2/ja active Active
- 2019-06-21 US US17/256,290 patent/US11242302B2/en active Active
- 2019-06-21 KR KR1020207036182A patent/KR102773808B1/ko active Active
- 2019-06-21 EP EP19731299.4A patent/EP3814307B1/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP7361057B2 (ja) | 2023-10-13 |
| EP3814307A1 (fr) | 2021-05-05 |
| JP2021528468A (ja) | 2021-10-21 |
| CN112585107B (zh) | 2024-04-02 |
| US20210261483A1 (en) | 2021-08-26 |
| PT3814307T (pt) | 2022-05-30 |
| CN112585107A (zh) | 2021-03-30 |
| US11242302B2 (en) | 2022-02-08 |
| KR20210030273A (ko) | 2021-03-17 |
| FR3083231A1 (fr) | 2020-01-03 |
| FR3083231B1 (fr) | 2020-07-17 |
| EP3814307B1 (fr) | 2022-04-20 |
| WO2020002142A1 (fr) | 2020-01-02 |
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| Date | Code | Title | Description |
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