CN1283608C - 从粗甲醇制备二甲醚的方法 - Google Patents
从粗甲醇制备二甲醚的方法 Download PDFInfo
- Publication number
- CN1283608C CN1283608C CNB2003101249009A CN200310124900A CN1283608C CN 1283608 C CN1283608 C CN 1283608C CN B2003101249009 A CNB2003101249009 A CN B2003101249009A CN 200310124900 A CN200310124900 A CN 200310124900A CN 1283608 C CN1283608 C CN 1283608C
- Authority
- CN
- China
- Prior art keywords
- zeolite
- catalyzer
- dimethyl ether
- catalyst
- ion
- 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.)
- Expired - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 200
- 238000000034 method Methods 0.000 title claims description 31
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title abstract description 32
- 239000010457 zeolite Substances 0.000 claims abstract description 62
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 61
- 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 60
- 230000018044 dehydration Effects 0.000 claims abstract description 34
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 20
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 230000000737 periodic effect Effects 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000002500 ions Chemical class 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 20
- 229930195733 hydrocarbon Natural products 0.000 abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 20
- 239000006227 byproduct Substances 0.000 abstract description 16
- 239000002994 raw material Substances 0.000 abstract description 9
- -1 hydrogen cations Chemical class 0.000 abstract description 7
- 230000009849 deactivation Effects 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000446 fuel Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910018404 Al2 O3 Inorganic materials 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 11
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 230000002779 inactivation Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 229910052680 mordenite Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000001354 calcination Methods 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- KMWBBMXGHHLDKL-UHFFFAOYSA-N [AlH3].[Si] Chemical compound [AlH3].[Si] KMWBBMXGHHLDKL-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical group [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940001516 sodium nitrate Drugs 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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)
Abstract
Description
例子 | 催化剂 | 氢阳离子(摩尔%) | 收率(%) | |
二甲醚 | 烃 | |||
实施例1 | NaHZSM-5 | 56 | 80.5 | 0.0 |
实施例2 | NaHZSM-5 | 22 | 80.4 | 0.0 |
实施例3 | NaH-β | 12 | 75.3 | 0.0 |
实施例4 | CuHMor | 28 | 78.1 | 0.0 |
实施例5 | ZnHUSY | 30 | 68.3 | 0.0 |
实施例6 | CuHZSM-5 | 20 | 80.4 | 0.0 |
实施例7 | ZnH-β | 27 | 76.2 | 0.0 |
实施例8 | NH4HZSM-5 | 43 | 78.7 | 0.0 |
实施例9 | NaHZSM-5 | 56 | 72.7 | 0.0 |
实施例10 | NaHZSM-5 | 56 | 75.4 | 0.0 |
实施例11 | NaHZSM-5 | 56 | 70.4 | 0.0 |
对比例1 | γ-氧化铝 | - | 48.0 | 0.0 |
对比例2 | 硅-铝 | 0 | 37.3 | 0.0 |
对比例3 | NaZSM-5 | 0 | 0.0 | 0.0 |
对比例4 | Na-β | 0 | 0.0 | 0.0 |
对比例5 | HZSM-5 | 100 | 78.1 | 2.1 |
对比例6 | H-β | 100 | 74.2 | 1.8 |
实施例 | 甲醇中水含量(摩尔%) | 收率(%) | |
二甲醚 | 烃 | ||
实施例12 | 10 | 68.5 | 0.0 |
实施例13 | 20 | 78.1 | 0.0 |
实施例14 | 40 | 63.3 | 0.0 |
Claims (3)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2002-0078856A KR100454091B1 (ko) | 2002-12-11 | 2002-12-11 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
KR78856/2002 | 2002-12-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1510021A CN1510021A (zh) | 2004-07-07 |
CN1283608C true CN1283608C (zh) | 2006-11-08 |
Family
ID=32310898
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101249009A Expired - Lifetime CN1283608C (zh) | 2002-12-11 | 2003-12-11 | 从粗甲醇制备二甲醚的方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US6740783B1 (zh) |
JP (1) | JP3612323B2 (zh) |
KR (1) | KR100454091B1 (zh) |
CN (1) | CN1283608C (zh) |
HK (1) | HK1066529A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104245651A (zh) * | 2012-02-23 | 2014-12-24 | 英国石油化学品有限公司 | 用于生产乙酸和二甲醚的方法 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100454091B1 (ko) * | 2002-12-11 | 2004-10-26 | 한국화학연구원 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
KR100599251B1 (ko) * | 2003-09-20 | 2006-07-13 | 에스케이 주식회사 | 디메틸에테르 합성용 촉매와 촉매의 제조방법 |
KR100629939B1 (ko) * | 2004-10-15 | 2006-09-28 | 에스케이 주식회사 | 단열반응기에서 미정제 메탄올로부터 디메틸에테르의제조방법 |
KR101133317B1 (ko) * | 2005-12-14 | 2012-04-04 | 에스케이이노베이션 주식회사 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
KR101208818B1 (ko) * | 2006-01-09 | 2012-12-06 | 에스케이이노베이션 주식회사 | 디메틸에테르 제조용 촉매, 이의 제조방법 및 이를 이용한메탄올로부터 디메틸에테르의 제조방법 |
KR101340777B1 (ko) * | 2006-08-31 | 2013-12-31 | 에스케이이노베이션 주식회사 | 디메틸에테르의 제조공정 |
FR2909666B1 (fr) * | 2006-12-08 | 2009-03-06 | Centre Nat Rech Scient | Deshydratation du methanol en dimethyl ether employant des catalyseurs a base d'une zeolithe supportee sur du carbure de silicium |
US20080260631A1 (en) | 2007-04-18 | 2008-10-23 | H2Gen Innovations, Inc. | Hydrogen production process |
US9139503B2 (en) * | 2007-09-10 | 2015-09-22 | Lummus Technology Inc. | Method for the production of dimethyl ether |
DE102008058931B4 (de) | 2008-11-25 | 2010-12-30 | Lurgi Gmbh | Verfahren und Vorrichtung zum Herstellen von Dimethylether aus Methanol |
US8378150B2 (en) * | 2009-08-12 | 2013-02-19 | Catalytic Distillation Technologies | Process for the production of dimethyl ether |
EP2292578A1 (en) * | 2009-09-03 | 2011-03-09 | BP Chemicals Limited | Process for producing acetic acid and dimethyl ether using a zeolite catalyst |
DE102009053357A1 (de) | 2009-11-17 | 2011-05-26 | Lurgi Gmbh | Herstellung von Dimethylether aus Rohmethanol |
WO2011060869A1 (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 |
US9272965B2 (en) * | 2009-12-22 | 2016-03-01 | Catalytic Distillation Technologies | Process for the conversion of alcohols to olefins |
MY185524A (en) | 2010-05-10 | 2021-05-19 | Catalytic Distillation Tech | Production of jet and other heavy fuels from isobutanol |
US9266804B2 (en) | 2010-12-01 | 2016-02-23 | Cpc Corporation | Dual-bed catalytic distillation tower and method for preparing dimethyl ether using the same |
US8575399B2 (en) | 2010-12-01 | 2013-11-05 | Cpc Corporation, Taiwan | Dual-bed catalytic distillation tower and method for preparing dimethyl ether using the same |
WO2014125038A1 (en) | 2013-02-15 | 2014-08-21 | Bp Chemicals Limited | Dehydration-hydrolysis processes and catalysts therefor |
JP6546738B2 (ja) * | 2014-11-12 | 2019-07-17 | 日立造船株式会社 | アルデヒド分解触媒および排ガス処理設備ならびに排ガス処理方法 |
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 |
KR101774435B1 (ko) * | 2016-02-24 | 2017-09-06 | 한국화학연구원 | 메탄올로부터 디메틸에테르를 제조하기 위한 에너지 절약형 공정 |
CN111491732A (zh) * | 2017-12-20 | 2020-08-04 | 巴斯夫欧洲公司 | 用于制备二甲醚的催化剂***和方法 |
CN114605235A (zh) * | 2022-04-15 | 2022-06-10 | 南京工业大学 | 一种co2加氢制二甲醚的方法 |
CN116510771A (zh) * | 2023-04-26 | 2023-08-01 | 哈尔滨师范大学 | 一种用于高含水量甲醇低温脱水制备二甲醚的催化剂的制备方法及在制备二甲醚中的应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US3036134A (en) * | 1962-05-22 | Method for converting alcohols | ||
CA1231724A (en) | 1982-07-01 | 1988-01-19 | E. I. Du Pont De Nemours And Company | Catalytic preparation of dimethyl ether |
JPS5916845A (ja) | 1982-07-16 | 1984-01-28 | Mitsubishi Gas Chem Co Inc | ジメチルエ−テルの製造方法 |
US4845063A (en) * | 1982-10-15 | 1989-07-04 | Mobil Oil Corporation | Zeolite catalyst of improved hydrothermal stability |
GB8829923D0 (en) * | 1988-12-22 | 1989-02-15 | Ici Plc | Zeolites |
US5684213A (en) * | 1996-03-25 | 1997-11-04 | Chemical Research & Licensing Company | Method for the preparation of dialkyl ethers |
KR100228748B1 (ko) * | 1997-10-10 | 1999-11-01 | 김충섭 | 이산화탄소로부터 디메틸에테르와 메탄올의 동시 제조방법 |
KR100362213B1 (ko) * | 1999-12-24 | 2002-11-23 | 에스케이 주식회사 | 다이아릴에탄의 연속 제조방법 |
KR100454091B1 (ko) * | 2002-12-11 | 2004-10-26 | 한국화학연구원 | 미정제 메탄올로부터 디메틸에테르의 제조방법 |
-
2002
- 2002-12-11 KR KR10-2002-0078856A patent/KR100454091B1/ko active IP Right Grant
-
2003
- 2003-04-15 US US10/413,535 patent/US6740783B1/en not_active Expired - Fee Related
- 2003-09-01 JP JP2003308997A patent/JP3612323B2/ja not_active Expired - Lifetime
- 2003-12-11 CN CNB2003101249009A patent/CN1283608C/zh not_active Expired - Lifetime
-
2004
- 2004-12-02 HK HK04109566A patent/HK1066529A1/xx not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104245651A (zh) * | 2012-02-23 | 2014-12-24 | 英国石油化学品有限公司 | 用于生产乙酸和二甲醚的方法 |
CN104245651B (zh) * | 2012-02-23 | 2016-08-17 | 英国石油化学品有限公司 | 用于生产乙酸和二甲醚的方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20040051032A (ko) | 2004-06-18 |
JP2004189719A (ja) | 2004-07-08 |
HK1066529A1 (en) | 2005-03-24 |
KR100454091B1 (ko) | 2004-10-26 |
US6740783B1 (en) | 2004-05-25 |
CN1510021A (zh) | 2004-07-07 |
JP3612323B2 (ja) | 2005-01-19 |
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