AU2005294990A1 - Process for preparing dimethyl ether from crude methanol in an adiabatic reactor - Google Patents
Process for preparing dimethyl ether from crude methanol in an adiabatic reactor Download PDFInfo
- Publication number
- AU2005294990A1 AU2005294990A1 AU2005294990A AU2005294990A AU2005294990A1 AU 2005294990 A1 AU2005294990 A1 AU 2005294990A1 AU 2005294990 A AU2005294990 A AU 2005294990A AU 2005294990 A AU2005294990 A AU 2005294990A AU 2005294990 A1 AU2005294990 A1 AU 2005294990A1
- Authority
- AU
- Australia
- Prior art keywords
- catalyst
- group
- dimethyl ether
- methanol
- zeolite
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 234
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims description 164
- 238000004519 manufacturing process Methods 0.000 title claims description 27
- 239000003054 catalyst Substances 0.000 claims description 152
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 119
- 239000010457 zeolite Substances 0.000 claims description 116
- 229910021536 Zeolite Inorganic materials 0.000 claims description 113
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 69
- 230000002209 hydrophobic effect Effects 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 150000001768 cations Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 230000003197 catalytic effect Effects 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 18
- 230000018044 dehydration Effects 0.000 claims description 14
- 238000006297 dehydration reaction Methods 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 description 41
- 150000002430 hydrocarbons Chemical class 0.000 description 41
- 238000000034 method Methods 0.000 description 32
- 239000006227 byproduct Substances 0.000 description 31
- 239000002253 acid Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
- 229910017604 nitric acid Inorganic materials 0.000 description 14
- 239000000376 reactant Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 10
- 229910001593 boehmite Inorganic materials 0.000 description 8
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 230000009849 deactivation Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229910052680 mordenite Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910001415 sodium ion Inorganic materials 0.000 description 5
- 239000004317 sodium nitrate Substances 0.000 description 5
- 235000010344 sodium nitrate Nutrition 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 229910052593 corundum Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- -1 USY Chemical compound 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 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
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020040082721A KR100629939B1 (ko) | 2004-10-15 | 2004-10-15 | 단열반응기에서 미정제 메탄올로부터 디메틸에테르의제조방법 |
| KR10-2004-0082721 | 2004-10-15 | ||
| PCT/KR2005/002751 WO2006041253A1 (en) | 2004-10-15 | 2005-08-19 | Process for preparing dimethyl ether from crude methanol in an adiabatic reactor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005294990A1 true AU2005294990A1 (en) | 2006-04-20 |
Family
ID=36148529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005294990A Abandoned AU2005294990A1 (en) | 2004-10-15 | 2005-08-19 | Process for preparing dimethyl ether from crude methanol in an adiabatic reactor |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20090023958A1 (enExample) |
| EP (1) | EP1799630A4 (enExample) |
| JP (1) | JP4778517B2 (enExample) |
| KR (1) | KR100629939B1 (enExample) |
| CN (1) | CN101119952A (enExample) |
| AU (1) | AU2005294990A1 (enExample) |
| TW (1) | TW200621697A (enExample) |
| WO (1) | WO2006041253A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5632438B2 (ja) * | 2006-08-30 | 2014-11-26 | 日揮株式会社 | ジメチルエーテルまたはメタノールを原料とする低級炭化水素合成用カルシウム化合物含有ゼオライト触媒の調製方法 |
| JP2008080301A (ja) * | 2006-08-30 | 2008-04-10 | Jgc Corp | アルカリ土類金属化合物含有ゼオライト触媒およびその調製方法、並びに、低級炭化水素の製造方法 |
| TWI406707B (zh) | 2006-08-30 | 2013-09-01 | Jgc Corp | 含鹼土類金屬化合物之沸石催化劑及其調製方法與再生方法、以及低級烴之製造方法 |
| EP2167452A1 (en) * | 2007-06-25 | 2010-03-31 | Mcneff Research Consultants, Inc. | Catalysts, systems and methods for ether synthesis |
| US8697893B2 (en) | 2008-12-22 | 2014-04-15 | Sartec Corporation | Systems and methods for producing fuels and fuel precursors from carbohydrates |
| CN101550067B (zh) * | 2009-05-15 | 2013-03-20 | 新奥新能(北京)科技有限公司 | 两段式二甲醚生产方法 |
| EP2292578A1 (en) | 2009-09-03 | 2011-03-09 | BP Chemicals Limited | Process for producing acetic acid and dimethyl ether using a zeolite catalyst |
| US20120220804A1 (en) | 2009-11-17 | 2012-08-30 | Lurgi Gmbh | Manufacture of dimethyl ether from crude methanol |
| DE102009053357A1 (de) * | 2009-11-17 | 2011-05-26 | Lurgi Gmbh | Herstellung von Dimethylether aus Rohmethanol |
| EP2322494B1 (de) | 2009-11-17 | 2013-01-09 | Lurgi GmbH | Herstellung von Dimethylether aus Rohmethanol |
| US9595186B2 (en) * | 2010-01-04 | 2017-03-14 | Samsung Electronics Co., Ltd. | Electronic device combining functions of touch screen and remote control and operation control method thereof |
| EP2531482B1 (en) * | 2010-02-04 | 2017-10-11 | Haldor Topsøe A/S | Process for the preparation of dimethyl ether |
| CN102463134B (zh) * | 2010-11-04 | 2013-08-28 | 中国石油化工股份有限公司 | 一种甲醇脱水制二甲醚催化剂及其制备方法和应用 |
| JP2012120977A (ja) * | 2010-12-08 | 2012-06-28 | Mitsubishi Chemicals Corp | 珪質固体触媒の製造方法及び低級炭化水素の製造方法 |
| DE102011114228A1 (de) | 2011-09-23 | 2013-03-28 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Gekühlter Reaktor zur Herstellung von Dimethylether aus Methanol |
| UA112887C2 (uk) * | 2012-02-23 | 2016-11-10 | Бп Кемікалз Лімітед | Спосіб одержання оцтової кислоти і диметилового ефіру |
| DE102012018341A1 (de) * | 2012-09-15 | 2014-05-15 | Thyssenkrupp Uhde Gmbh | Verfahren zur Herstellung von Dimethylether und dafür geeignete Vorrichtung |
| US9247281B2 (en) | 2013-01-11 | 2016-01-26 | Htc Corporation | Handheld electronic device having universal remote control mechanism and operation method of the same |
| US20150088282A1 (en) * | 2013-09-24 | 2015-03-26 | Fibar Group sp. z o. o. | Touch-less swipe control |
| DE102014118966A1 (de) | 2014-12-18 | 2015-12-31 | L’AIR LIQUIDE Société Anonyme pour l’Etude et l’Exploitation des Procédés Georges Claude | Anlage, Verfahren und Katalysator zur Herstellung von Dimethylether |
| KR102467394B1 (ko) * | 2016-05-24 | 2022-11-15 | 에스케이이노베이션 주식회사 | 단열 반응기를 이용하여 2,3-부탄디올로부터 1,3-부타디엔 및 메틸에틸케톤을 제조하는 방법 |
| US10239812B2 (en) | 2017-04-27 | 2019-03-26 | Sartec Corporation | Systems and methods for synthesis of phenolics and ketones |
| CN109092349A (zh) * | 2017-06-20 | 2018-12-28 | 高化学技术株式会社 | 用于制备乙二醇二甲醚的催化剂及其制备方法和应用 |
| CA3086707A1 (en) * | 2017-12-20 | 2019-06-27 | Basf Se | Catalyst system and process for preparing dimethyl ether |
| US10696923B2 (en) | 2018-02-07 | 2020-06-30 | Sartec Corporation | Methods and apparatus for producing alkyl esters from lipid feed stocks, alcohol feedstocks, and acids |
| US10544381B2 (en) | 2018-02-07 | 2020-01-28 | Sartec Corporation | Methods and apparatus for producing alkyl esters from a reaction mixture containing acidified soap stock, alcohol feedstock, and acid |
| CN115368375B (zh) * | 2021-05-19 | 2024-01-26 | 中国石油化工股份有限公司 | 一种制备氧杂-降冰片烯的方法 |
| KR102834277B1 (ko) | 2023-06-22 | 2025-07-17 | (주)송천이앤씨 | 모듈러 보강대용 체결판 지그 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123448A (en) * | 1977-06-01 | 1978-10-31 | Continental Oil Company | Adiabatic reactor |
| BR8303437A (pt) * | 1982-07-01 | 1984-02-07 | Du Pont | Processo para a preparacao de eter dimetilico pela desidratacao catalitica de metanol |
| AU603070B2 (en) * | 1986-11-18 | 1990-11-08 | Rwe-Dea Aktiengesellschaft Fur Mineraloel Und Chemie | Process for the purification of dimethylether |
| US4885405A (en) * | 1987-12-10 | 1989-12-05 | Horst Dornhagen | Process for the production of pure dimethylether and a catalyst used in the process |
| US5684213A (en) * | 1996-03-25 | 1997-11-04 | Chemical Research & Licensing Company | Method for the preparation of dialkyl ethers |
| US6608114B1 (en) * | 2002-03-13 | 2003-08-19 | Air Products And Chemicals, Inc. | Process to produce DME |
| KR100454091B1 (ko) * | 2002-12-11 | 2004-10-26 | 한국화학연구원 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
| KR100501922B1 (ko) * | 2003-02-19 | 2005-07-18 | 에스케이 주식회사 | 메탄올로부터 디메틸에테르의 제조방법 |
-
2004
- 2004-10-15 KR KR1020040082721A patent/KR100629939B1/ko not_active Expired - Fee Related
-
2005
- 2005-08-19 CN CNA2005800347590A patent/CN101119952A/zh active Pending
- 2005-08-19 EP EP05825764A patent/EP1799630A4/en not_active Withdrawn
- 2005-08-19 JP JP2007536604A patent/JP4778517B2/ja not_active Expired - Fee Related
- 2005-08-19 AU AU2005294990A patent/AU2005294990A1/en not_active Abandoned
- 2005-08-19 WO PCT/KR2005/002751 patent/WO2006041253A1/en not_active Ceased
- 2005-08-19 US US11/665,112 patent/US20090023958A1/en not_active Abandoned
- 2005-10-14 TW TW094135885A patent/TW200621697A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100629939B1 (ko) | 2006-09-28 |
| KR20060033551A (ko) | 2006-04-19 |
| EP1799630A1 (en) | 2007-06-27 |
| EP1799630A4 (en) | 2009-12-02 |
| JP4778517B2 (ja) | 2011-09-21 |
| WO2006041253A1 (en) | 2006-04-20 |
| TW200621697A (en) | 2006-07-01 |
| JP2008516943A (ja) | 2008-05-22 |
| US20090023958A1 (en) | 2009-01-22 |
| CN101119952A (zh) | 2008-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2005294990A1 (en) | Process for preparing dimethyl ether from crude methanol in an adiabatic reactor | |
| KR100454091B1 (ko) | 미정제 메탄올로부터 디메틸에테르의 제조방법 | |
| US8653314B2 (en) | Method for providing a co-feed in the coupling of toluene with a carbon source | |
| EP2238094B1 (en) | Dehydration of alcohols on crystalline silicates | |
| CN100503041C (zh) | 用于二甲醚合成的催化剂及其制备方法 | |
| US11136276B2 (en) | Single-stage method of butadiene production | |
| JP2008516943A5 (enExample) | ||
| KR100966706B1 (ko) | 메탄올로부터 디메틸에테르를 제조하는 방법 | |
| JPS6210488B2 (enExample) | ||
| US5120893A (en) | Process for catalytically converting C10 and higher olefins to C9 and lower olefins | |
| KR100926800B1 (ko) | 메탄올의 탈수반응에 의한 디메틸에테르 합성용 촉매, 이의제조방법 및 디메틸에테르의 제조방법 | |
| CN100494129C (zh) | 制备丙烯的方法 | |
| KR101133317B1 (ko) | 미정제 메탄올로부터 디메틸에테르의 제조방법 | |
| JPS6221337B2 (enExample) | ||
| US20140128247A1 (en) | Nitrogen Containing Catalyst for Coupling Reactions | |
| WO2022102600A1 (ja) | シクロヘキシルベンゼンの製造方法及びこれを用いたシクロヘキシルベンゼン組成物 | |
| JPS6158451B2 (enExample) | ||
| WO2025166123A2 (en) | Systems and processes for catalytic conversion of bio-based materials | |
| WO2020260237A1 (en) | A method of preparing ethylbenzene | |
| HK1066529B (en) | Process for preparing dimethyl ether from crude methanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: SK ENERGY CO., LTD. Free format text: FORMER APPLICANT(S): SK CORPORATION |
|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |