KR20050101555A - 파라-크실렌의 제조 방법 - Google Patents
파라-크실렌의 제조 방법 Download PDFInfo
- Publication number
- KR20050101555A KR20050101555A KR1020057015138A KR20057015138A KR20050101555A KR 20050101555 A KR20050101555 A KR 20050101555A KR 1020057015138 A KR1020057015138 A KR 1020057015138A KR 20057015138 A KR20057015138 A KR 20057015138A KR 20050101555 A KR20050101555 A KR 20050101555A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- methanol
- toluene
- xylene
- para
- 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.)
- Ceased
Links
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 168
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 138
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 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 14
- 239000010457 zeolite Substances 0.000 claims abstract description 14
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 239000000571 coke Substances 0.000 claims abstract description 8
- 238000011935 selective methylation Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 239000011777 magnesium Substances 0.000 claims description 13
- 229910052749 magnesium Inorganic materials 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 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
- 239000007788 liquid Substances 0.000 description 8
- 230000011987 methylation Effects 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 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
- 230000000694 effects Effects 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000004939 coking Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 230000008901 benefit Effects 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000004904 shortening Methods 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
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 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
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007809 chemical reaction catalyst 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
- 230000001010 compromised effect Effects 0.000 description 1
- 238000005235 decoking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007873 sieving Methods 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
- 150000003613 toluenes 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0303659.7 | 2003-02-18 | ||
| GBGB0303659.7A GB0303659D0 (en) | 2003-02-18 | 2003-02-18 | Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050101555A true KR20050101555A (ko) | 2005-10-24 |
Family
ID=9953191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057015138A Ceased KR20050101555A (ko) | 2003-02-18 | 2004-02-18 | 파라-크실렌의 제조 방법 |
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=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120025486A (ko) * | 2009-05-28 | 2012-03-15 | 사우디 베이식 인더스트리즈 코포레이션 | 방향족 알킬화 공정 |
Families Citing this family (15)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120025486A (ko) * | 2009-05-28 | 2012-03-15 | 사우디 베이식 인더스트리즈 코포레이션 | 방향족 알킬화 공정 |
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 |
| JP2006517957A (ja) | 2006-08-03 |
| CA2515914A1 (en) | 2004-09-02 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20050817 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20090216 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20101027 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20110621 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20101027 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |