CA2906032A1 - Process for recovering paraxylene from at least two feedstreams containing xylene isomers - Google Patents
Process for recovering paraxylene from at least two feedstreams containing xylene isomers Download PDFInfo
- Publication number
- CA2906032A1 CA2906032A1 CA2906032A CA2906032A CA2906032A1 CA 2906032 A1 CA2906032 A1 CA 2906032A1 CA 2906032 A CA2906032 A CA 2906032A CA 2906032 A CA2906032 A CA 2906032A CA 2906032 A1 CA2906032 A1 CA 2906032A1
- Authority
- CA
- Canada
- Prior art keywords
- paraxylene
- feedstream
- zone
- rich
- reslurry
- 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.)
- Abandoned
Links
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 807
- 238000000034 method Methods 0.000 title claims abstract description 106
- 150000003738 xylenes Chemical class 0.000 title claims abstract description 104
- 238000011084 recovery Methods 0.000 claims abstract description 107
- 238000002425 crystallisation Methods 0.000 claims abstract description 87
- 230000008025 crystallization Effects 0.000 claims abstract description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 108
- 239000008096 xylene Substances 0.000 claims description 39
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 239000003507 refrigerant Substances 0.000 claims description 26
- 238000006317 isomerization reaction Methods 0.000 claims description 25
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000010555 transalkylation reaction Methods 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 238000007323 disproportionation reaction Methods 0.000 claims description 11
- 238000005194 fractionation Methods 0.000 claims description 11
- 239000001294 propane Substances 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 238000001179 sorption measurement Methods 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 239000002826 coolant Substances 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000011935 selective methylation Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 81
- 239000000047 product Substances 0.000 description 62
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 48
- 238000000926 separation method Methods 0.000 description 40
- 239000007787 solid Substances 0.000 description 34
- 239000000706 filtrate Substances 0.000 description 31
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 24
- 239000002002 slurry Substances 0.000 description 21
- 239000003085 diluting agent Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- 239000012065 filter cake Substances 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 10
- 238000005057 refrigeration Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000005496 eutectics Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011144 upstream manufacturing Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 239000006194 liquid suspension Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- SWYQVERVQJDMFB-UHFFFAOYSA-N (2-hydroperoxy-2-methylpropyl)benzene Chemical compound OOC(C)(C)CC1=CC=CC=C1 SWYQVERVQJDMFB-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- 239000003463 adsorbent Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- -1 aliphatic aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- 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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361794401P | 2013-03-15 | 2013-03-15 | |
| US61/794,401 | 2013-03-15 | ||
| PCT/US2014/027705 WO2014152762A1 (en) | 2013-03-15 | 2014-03-14 | Process for recovering paraxylene from at least two feedstreams containing xylene isomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2906032A1 true CA2906032A1 (en) | 2014-09-25 |
Family
ID=50483586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2906032A Abandoned CA2906032A1 (en) | 2013-03-15 | 2014-03-14 | Process for recovering paraxylene from at least two feedstreams containing xylene isomers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10351491B2 (enExample) |
| EP (1) | EP2970048B1 (enExample) |
| JP (1) | JP6378747B2 (enExample) |
| KR (1) | KR102168050B1 (enExample) |
| CN (1) | CN105228975A (enExample) |
| BR (1) | BR112015023508A8 (enExample) |
| CA (1) | CA2906032A1 (enExample) |
| MX (1) | MX2015012077A (enExample) |
| RU (1) | RU2687492C2 (enExample) |
| SG (1) | SG11201507348SA (enExample) |
| WO (1) | WO2014152762A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10793493B2 (en) * | 2017-08-31 | 2020-10-06 | Uop Llc | Process for recovering benzene and fuel gas in an aromatics complex |
| CN111655654B (zh) * | 2017-12-05 | 2023-05-05 | 英力士美国化学公司 | 使用减少的结晶载量回收对二甲苯的方法 |
| US11040930B2 (en) * | 2017-12-05 | 2021-06-22 | Ineos Us Chemicals Company | Method of recovering paraxylene in a crystallization zone |
| FR3080857B1 (fr) * | 2018-05-04 | 2020-05-08 | Axens | Procede et dispositif de separation d'aromatiques sous vide |
| WO2021173798A1 (en) * | 2020-02-29 | 2021-09-02 | Ineos Us Chemicals Company | Separation process and apparatus |
| CN111185026B (zh) * | 2020-03-03 | 2025-07-04 | 中海石油宁波大榭石化有限公司 | C9芳烃和c8芳烃分离装置及分离方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2827503A (en) * | 1953-05-01 | 1958-03-18 | Standard Oil Co | Recovery of para-xylene from solutions containing the xylene isomers |
| US2810772A (en) * | 1953-12-07 | 1957-10-22 | Exxon Research Engineering Co | Process for production and recovery of paraxylene |
| FR2177644B1 (enExample) * | 1972-03-31 | 1975-06-13 | Inst Francais Du Petrole | |
| US4393266A (en) * | 1980-05-23 | 1983-07-12 | Texaco Inc. | Separation of para-xylene |
| US5329060A (en) * | 1993-04-01 | 1994-07-12 | Uop | Integrated selective adsorption and crystallization process for para-xylene recovery |
| US5329061A (en) * | 1993-06-01 | 1994-07-12 | Uop | Crystallization process for para-xylene recovery using two-stage recovery section |
| US5448005A (en) | 1994-04-04 | 1995-09-05 | Mobil Oil Corporation | Crystallization of paraxlene from high purity paraxylene feeds |
| FR2728894A1 (fr) * | 1994-12-29 | 1996-07-05 | Inst Francais Du Petrole | Procede de separation de paraxylene comportant au moins deux etages de cristallisation a haute temperature |
| FR2729660A1 (fr) | 1995-01-20 | 1996-07-26 | Inst Francais Du Petrole | Procede de production de paraxylene comportant une cristallisation a haute temperature a au moins un etage et une fusion partielle des cristaux |
| US6878855B2 (en) * | 2000-02-22 | 2005-04-12 | Exxonmobil Chemical Patents Inc. | Process for producing para-xylene |
| US6565653B2 (en) | 2001-05-08 | 2003-05-20 | Bp Corporation North America Inc. | Energy efficient process for producing high purity paraxylene |
| US8211319B2 (en) | 2003-09-16 | 2012-07-03 | Bp Corporation North America Inc. | Solid-liquid separation process |
| US7405340B2 (en) * | 2004-04-01 | 2008-07-29 | Bp Corporation North America Inc. | Process for recovering paraxylene utilizing ammonia absorption refrigeration |
| US7812206B2 (en) | 2006-03-21 | 2010-10-12 | Bp Corporation North America Inc. | Apparatus and process for the separation of solids and liquids |
| BRPI0809848A2 (pt) * | 2007-04-04 | 2014-09-23 | Exxonmobil Chem Patents Inc | Processo e aparelho para a produção de para-xileno |
| US8530716B2 (en) * | 2008-08-14 | 2013-09-10 | Bp Corporation North America Inc. | Melt-crystallization separation and purification process |
| US8252967B2 (en) | 2009-04-14 | 2012-08-28 | Exxonmobil Chemical Patents Inc. | Process for the purification of paraxylene |
| KR20140038946A (ko) | 2011-01-12 | 2014-03-31 | 비피 코포레이션 노쓰 아메리카 인코포레이티드 | 탄화수소 전환 촉매 제조 및 사용 방법 |
| US9422208B2 (en) * | 2013-05-07 | 2016-08-23 | Exxonmobil Chemical Patents Inc. | Treatment of aromatic hydrocarbon stream |
-
2014
- 2014-03-14 CA CA2906032A patent/CA2906032A1/en not_active Abandoned
- 2014-03-14 MX MX2015012077A patent/MX2015012077A/es unknown
- 2014-03-14 RU RU2015142879A patent/RU2687492C2/ru not_active IP Right Cessation
- 2014-03-14 BR BR112015023508A patent/BR112015023508A8/pt not_active Application Discontinuation
- 2014-03-14 US US14/777,077 patent/US10351491B2/en not_active Expired - Fee Related
- 2014-03-14 WO PCT/US2014/027705 patent/WO2014152762A1/en not_active Ceased
- 2014-03-14 SG SG11201507348SA patent/SG11201507348SA/en unknown
- 2014-03-14 JP JP2016502525A patent/JP6378747B2/ja not_active Expired - Fee Related
- 2014-03-14 CN CN201480021443.7A patent/CN105228975A/zh active Pending
- 2014-03-14 KR KR1020157029377A patent/KR102168050B1/ko not_active Expired - Fee Related
- 2014-03-14 EP EP14717357.9A patent/EP2970048B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014152762A1 (en) | 2014-09-25 |
| SG11201507348SA (en) | 2015-10-29 |
| EP2970048B1 (en) | 2020-06-10 |
| BR112015023508A2 (pt) | 2017-07-18 |
| US20160031772A1 (en) | 2016-02-04 |
| JP2016512267A (ja) | 2016-04-25 |
| BR112015023508A8 (pt) | 2019-09-10 |
| EP2970048A1 (en) | 2016-01-20 |
| RU2687492C2 (ru) | 2019-05-14 |
| JP6378747B2 (ja) | 2018-08-22 |
| US10351491B2 (en) | 2019-07-16 |
| KR20150132439A (ko) | 2015-11-25 |
| MX2015012077A (es) | 2015-11-18 |
| KR102168050B1 (ko) | 2020-10-20 |
| RU2015142879A (ru) | 2017-04-26 |
| CN105228975A (zh) | 2016-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20200831 |