CA2515914A1 - Process for producing para-xylene - Google Patents
Process for producing para-xylene Download PDFInfo
- Publication number
- CA2515914A1 CA2515914A1 CA002515914A CA2515914A CA2515914A1 CA 2515914 A1 CA2515914 A1 CA 2515914A1 CA 002515914 A CA002515914 A CA 002515914A CA 2515914 A CA2515914 A CA 2515914A CA 2515914 A1 CA2515914 A1 CA 2515914A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- process according
- methanol
- toluene
- xylene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 49
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 171
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 135
- 239000003054 catalyst Substances 0.000 claims abstract description 74
- 239000000376 reactant Substances 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 12
- 239000010457 zeolite Substances 0.000 claims abstract description 12
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 11
- 238000011935 selective methylation Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000011777 magnesium Substances 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 239000000571 coke Substances 0.000 abstract description 7
- 239000008096 xylene Substances 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000007069 methylation reaction Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 230000011987 methylation Effects 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052878 cordierite Inorganic materials 0.000 description 5
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000004939 coking Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000012494 Quartz wool Substances 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0303659.7 | 2003-02-18 | ||
| GBGB0303659.7A GB0303659D0 (en) | 2003-02-18 | 2003-02-18 | Process |
| PCT/GB2004/000648 WO2004074219A2 (en) | 2003-02-18 | 2004-02-18 | Process for producing para-xylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2515914A1 true CA2515914A1 (en) | 2004-09-02 |
Family
ID=9953191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002515914A Abandoned CA2515914A1 (en) | 2003-02-18 | 2004-02-18 | Process for producing para-xylene |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7321072B2 (https=) |
| EP (1) | EP1594822A2 (https=) |
| JP (1) | JP2006517957A (https=) |
| KR (1) | KR20050101555A (https=) |
| CN (1) | CN100349835C (https=) |
| BR (1) | BRPI0407589A (https=) |
| CA (1) | CA2515914A1 (https=) |
| GB (1) | GB0303659D0 (https=) |
| MX (1) | MXPA05008768A (https=) |
| PL (1) | PL378077A1 (https=) |
| RU (1) | RU2331621C2 (https=) |
| WO (1) | WO2004074219A2 (https=) |
| ZA (1) | ZA200506468B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7060864B2 (en) | 2003-09-30 | 2006-06-13 | Saudi Basic Industries Corporation | Toluene methylation process |
| CN101723792B (zh) * | 2008-10-16 | 2013-05-08 | 微宏动力系统（湖州）有限公司 | 一种制备二甲苯的方法 |
| US8252967B2 (en) * | 2009-04-14 | 2012-08-28 | Exxonmobil Chemical Patents Inc. | Process for the purification of paraxylene |
| CN101885662B (zh) * | 2009-05-13 | 2013-09-18 | 中国石油化工股份有限公司 | 甲苯甲醇烷基化的方法 |
| US8558046B2 (en) * | 2009-05-28 | 2013-10-15 | Saudi Basic Industries Corporation | Aromatic alkylation process |
| HU231091B1 (hu) | 2009-09-30 | 2020-07-28 | Mol Magyar Olaj- És Gázipari Nyilvánosan Működő Részvénytársaság | Belső égésű motoroknál használható hajtóanyagok és hajtóanyag-adalékok, valamint eljárás ezek előállítására |
| US8399727B2 (en) | 2009-10-21 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Production of para-xylene by the methylation of benzene and/or toluene |
| ITMI20111143A1 (it) * | 2011-06-23 | 2012-12-24 | Polimeri Europa Spa | Procedimento per l'alchilazione di idrocarburi aromatici con alcoli c1-c8 |
| MX2014006759A (es) * | 2011-12-08 | 2015-03-03 | Gtc Technology Us Llc | Produccion de xilenos por metilacion de compuestos aromaticos. |
| AU2013243901A1 (en) * | 2012-04-05 | 2014-11-20 | Gtc Technology Us Llc | Process for production of xylenes through integration of methylation and transalkylation |
| CN103772129A (zh) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | 甲苯甲基化生产混合二甲苯的方法 |
| CN105344373A (zh) * | 2015-10-26 | 2016-02-24 | 常州大学 | 一种用于合成对二甲苯过程择形催化剂的制备方法 |
| US11208365B2 (en) | 2016-12-20 | 2021-12-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| WO2018118592A1 (en) * | 2016-12-20 | 2018-06-28 | Uop Llc | Processes and apparatuses for toluene methylation in an aromatics complex |
| US11130719B2 (en) | 2017-12-05 | 2021-09-28 | Uop Llc | Processes and apparatuses for methylation of aromatics in an aromatics complex |
| US11130720B2 (en) | 2018-03-23 | 2021-09-28 | Uop Llc | Processes for methylation of aromatics in an aromatics complex |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965208A (en) | 1975-01-06 | 1976-06-22 | Mobil Oil Corporation | Methylation of toluene |
| US4029716A (en) | 1975-12-08 | 1977-06-14 | Mobil Oil Corporation | Selective production of para-xylene |
| US4034053A (en) | 1975-12-08 | 1977-07-05 | Mobil Oil Corporation | Selective production of para-xylene |
| US4250345A (en) * | 1978-01-10 | 1981-02-10 | Mobil Oil Corporation | Selective production of para-xylene |
| US4152364A (en) | 1978-01-19 | 1979-05-01 | Mobil Oil Corporation | Selective production of para-xylene |
| JPS54144324A (en) | 1978-04-28 | 1979-11-10 | Teijin Yuka Kk | Manufacture of ppxylene |
| JPS54144323A (en) * | 1978-04-28 | 1979-11-10 | Teijin Yuka Kk | Manufacture of ppxylene |
| JPS5645419A (en) | 1979-09-21 | 1981-04-25 | Teijin Yuka Kk | Preparation of p-xylene |
| US4288647A (en) * | 1980-03-10 | 1981-09-08 | Mobil Oil Corporation | Shape selective reactions with alkaline earth-modified zeolite catalysts |
| JPS5726627A (en) * | 1980-07-25 | 1982-02-12 | Teijin Yuka Kk | Preparation of p-xylene |
| JPS5835130A (ja) | 1981-08-26 | 1983-03-01 | Teijin Yuka Kk | Ｐ−キシレンの製造法 |
| JPS6263528A (ja) * | 1985-09-17 | 1987-03-20 | Teijin Yuka Kk | Ｐ−キシレンの製造法 |
| US5939597A (en) | 1994-11-10 | 1999-08-17 | Mobil Oil Corporation | Fluid bed process for para-xylene production |
| ZA978671B (en) * | 1996-10-02 | 1999-03-26 | Mobil Oil Corp | Selective para-xylene production by toluene methylation |
-
2003
- 2003-02-18 GB GBGB0303659.7A patent/GB0303659D0/en not_active Ceased
-
2004
- 2004-02-18 CN CNB2004800063471A patent/CN100349835C/zh not_active Expired - Fee Related
- 2004-02-18 KR KR1020057015138A patent/KR20050101555A/ko not_active Ceased
- 2004-02-18 PL PL378077A patent/PL378077A1/pl unknown
- 2004-02-18 RU RU2005129112/04A patent/RU2331621C2/ru not_active IP Right Cessation
- 2004-02-18 MX MXPA05008768A patent/MXPA05008768A/es unknown
- 2004-02-18 CA CA002515914A patent/CA2515914A1/en not_active Abandoned
- 2004-02-18 US US10/545,770 patent/US7321072B2/en not_active Expired - Fee Related
- 2004-02-18 JP JP2006502294A patent/JP2006517957A/ja active Pending
- 2004-02-18 WO PCT/GB2004/000648 patent/WO2004074219A2/en not_active Ceased
- 2004-02-18 EP EP04712094A patent/EP1594822A2/en not_active Withdrawn
- 2004-02-18 BR BRPI0407589-7A patent/BRPI0407589A/pt not_active IP Right Cessation
-
2005
- 2005-08-12 ZA ZA200506468A patent/ZA200506468B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004074219B1 (en) | 2004-11-25 |
| WO2004074219A2 (en) | 2004-09-02 |
| RU2005129112A (ru) | 2006-03-20 |
| RU2331621C2 (ru) | 2008-08-20 |
| WO2004074219A3 (en) | 2004-10-14 |
| GB0303659D0 (en) | 2003-03-19 |
| CN1759081A (zh) | 2006-04-12 |
| KR20050101555A (ko) | 2005-10-24 |
| JP2006517957A (ja) | 2006-08-03 |
| CN100349835C (zh) | 2007-11-21 |
| BRPI0407589A (pt) | 2006-02-14 |
| MXPA05008768A (es) | 2006-03-21 |
| ZA200506468B (en) | 2006-05-31 |
| PL378077A1 (pl) | 2006-02-20 |
| US7321072B2 (en) | 2008-01-22 |
| US20060264685A1 (en) | 2006-11-23 |
| EP1594822A2 (en) | 2005-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3805409B2 (ja) | 芳香族化合物のアルキル化またはアルキル交換方法及びそれに用いる触媒組成物 | |
| CA2515914A1 (en) | Process for producing para-xylene | |
| JP3773530B2 (ja) | 重質芳香族化合物の処理 | |
| EP1976813A2 (en) | Production method for propylene, restoration method for catalyst, and solid acid catalyst | |
| CA2327688A1 (en) | Catalyst and process for converting methanol to hydrocarbons | |
| WO2014120422A1 (en) | Production of para-xylene | |
| KR20190105086A (ko) | 프로필렌 생산을 위한 이중 촉매 공정 및 시스템 | |
| KR20210135329A (ko) | 메소다공성 촉매 화합물 및 이의 용도 | |
| JPS6024769B2 (ja) | キシレンの気相異性化法 | |
| Aboul-Gheit et al. | Catalytic para-xylene maximization II–alkylation of toluene with methanol on platinum loaded H-ZSM-5 zeolite catalysts prepared via different routes | |
| Uguina et al. | Magnesium and silicon as ZSM-5 modifier agents for selective toluene disproportionation | |
| Das et al. | Ethylbenzene dealkylation and realkylation over pore size regulated MFI zeolite | |
| EP1196363B1 (en) | Process for the production of propylene from olefinic streams | |
| JP7417920B2 (ja) | 軽質炭化水素の部分酸化触媒ならびに該触媒による一酸化炭素と水素の製造方法 | |
| KR20180119612A (ko) | 파라-크실렌의 제조 방법 및 촉매 | |
| JP7711542B2 (ja) | Ｍｆｉ型ゼオライト及びそれを含む炭化水素製造用触媒 | |
| Aboul‐Gheit et al. | Catalytic Para‐Xylene Maximization. V. Toluene Methylation with Methanol and Disproportionation of Toluene Using Pt/ZSM‐5 and Pt/Mordenite Catalysts | |
| Nibou et al. | Dependence between the activity and selectivity of NaLaY and NaCeY catalysts in the catalytic disproportionation of toluene | |
| EP0580847B1 (en) | Catalyst and process for hydrocarbon dehydrogenation | |
| JP2013166755A (ja) | トルエンの不均化方法 | |
| US4982032A (en) | Process for converting a wet acetylene-containing stream to aromatics using a zinc-promoted, crystalline, borosilicate molecular sieve catalyst composition | |
| US4795853A (en) | Isoparaffin synthesis over cadmium catalysts | |
| Yarlagadda et al. | Conversion of methanol to hydrocarbons over silica-alumina: Selective Formation of Lower Olefins | |
| JP7838284B2 (ja) | 炭化水素化合物の製造方法 | |
| JP7452205B2 (ja) | アルコール転換触媒 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |