JP2013523633A - 前処理されたエポキシ化触媒を使用してプロピレンオキシドを製造する方法 - Google Patents
前処理されたエポキシ化触媒を使用してプロピレンオキシドを製造する方法 Download PDFInfo
- Publication number
- JP2013523633A JP2013523633A JP2013501249A JP2013501249A JP2013523633A JP 2013523633 A JP2013523633 A JP 2013523633A JP 2013501249 A JP2013501249 A JP 2013501249A JP 2013501249 A JP2013501249 A JP 2013501249A JP 2013523633 A JP2013523633 A JP 2013523633A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- pretreated
- methanol
- propylene
- titanium
- 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.)
- Pending
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 105
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims description 60
- 238000006735 epoxidation reaction Methods 0.000 title claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 253
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 33
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 150000003608 titanium Chemical class 0.000 claims abstract description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
- 239000010936 titanium Substances 0.000 claims description 25
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 21
- 229910052719 titanium Inorganic materials 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- -1 peroxide compound Chemical class 0.000 claims description 7
- 229910021536 Zeolite Inorganic materials 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000010457 zeolite Substances 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 238000007605 air drying Methods 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 9
- 230000008901 benefit Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229910003077 Ti−O Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/80—Mixtures of different zeolites
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31739010P | 2010-03-25 | 2010-03-25 | |
| US61/317,390 | 2010-03-25 | ||
| PCT/US2011/000523 WO2011119217A1 (en) | 2010-03-25 | 2011-03-22 | Process for producing propylene oxide using a pretreated epoxidation catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013523633A true JP2013523633A (ja) | 2013-06-17 |
| JP2013523633A5 JP2013523633A5 (https=) | 2014-05-08 |
Family
ID=44065153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501249A Pending JP2013523633A (ja) | 2010-03-25 | 2011-03-22 | 前処理されたエポキシ化触媒を使用してプロピレンオキシドを製造する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8703983B2 (https=) |
| EP (1) | EP2550259A1 (https=) |
| JP (1) | JP2013523633A (https=) |
| KR (1) | KR20130040190A (https=) |
| CN (1) | CN102822158A (https=) |
| BR (1) | BR112012024298A8 (https=) |
| TW (1) | TWI523689B (https=) |
| WO (1) | WO2011119217A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017524706A (ja) * | 2014-07-29 | 2017-08-31 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | オレフィンをエポキシ化するための方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5223980B2 (ja) | 2011-04-21 | 2013-06-26 | 大日本印刷株式会社 | 色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置及び有機発光表示装置 |
| WO2016164595A1 (en) | 2015-04-09 | 2016-10-13 | Lyondell Chemical Technology, L.P. | Process for forming propylene oxide from oxidation of methyl benzyl alcohol |
| HUE045453T2 (hu) * | 2015-11-26 | 2019-12-30 | Evonik Degussa Gmbh | Eljárás propén epoxidálására |
| CN108191794B (zh) * | 2017-12-29 | 2020-02-11 | 中触媒新材料股份有限公司 | 一种丙烯环氧化反应方法 |
| CN108689966A (zh) * | 2018-05-21 | 2018-10-23 | 华东师范大学 | 一种环氧丙烷的制备方法 |
| CN111085264B (zh) * | 2018-10-23 | 2022-12-06 | 华东理工大学 | 基于碳多孔陶瓷的整构式改性ts-1催化剂及制备方法与应用 |
| CN112742472B (zh) * | 2021-01-19 | 2022-03-15 | 中国科学院大连化学物理研究所 | 一种高活性低副产的环氧化催化剂的制备方法 |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5951273A (ja) * | 1982-07-28 | 1984-03-24 | エニーケム・シンテシース・エセ・ピ・ア | オレフイン化合物のエポキシ化法 |
| JPS62185081A (ja) * | 1986-01-28 | 1987-08-13 | エニリチェルケ・エセ・ピ・ア | オレフイン化合物のエポキシ化法 |
| JPH1025285A (ja) * | 1996-07-08 | 1998-01-27 | Mitsubishi Gas Chem Co Inc | オレフィン化合物のエポキシ化法 |
| JPH1180144A (ja) * | 1997-09-04 | 1999-03-26 | Daiso Co Ltd | オレフィンの選択的エポキシ化法 |
| JP2001509821A (ja) * | 1998-03-26 | 2001-07-24 | レプソル キミカ，ソシエダ アノニマ | 溶媒の存在下での過酸化水素によるオレフィン性化合物のエポキシ化方法 |
| JP2005511524A (ja) * | 2001-10-09 | 2005-04-28 | アルコ ケミカル テクノロジィ， エル．ピー． | 前処理したチタンゼオライトを使用する直接エポキシ化方法 |
| WO2007013739A1 (en) * | 2005-07-27 | 2007-02-01 | Sk Energy Co., Ltd. | Method of regeneration of titanium-containing molecular sieve catalyst |
| JP2008502476A (ja) * | 2004-06-14 | 2008-01-31 | ライオンデル ケミカル テクノロジー、 エル．ピー． | 触媒の再生方法 |
| JP2008524214A (ja) * | 2004-12-17 | 2008-07-10 | ライオンデル ケミカル テクノロジー、 エル．ピー． | チタンまたはバナジウムゼオライト触媒をアミノ多塩基酸で前処理するエポキシ化方法 |
| JP2013523422A (ja) * | 2010-03-25 | 2013-06-17 | ダウ グローバル テクノロジーズ エルエルシー | 前処理されたエポキシ化触媒及びそれによりオレフィンを製造する方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1127311B (it) | 1979-12-21 | 1986-05-21 | Anic Spa | Materiale sintetico,cristallino,poroso costituito da ossidi di silicio e titanio,metodo per la sua preparazione e suoi usi |
| DE19835907A1 (de) | 1998-08-07 | 2000-02-17 | Basf Ag | Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid |
| DE10032885A1 (de) | 2000-07-06 | 2002-01-17 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| CN1159218C (zh) * | 2001-05-30 | 2004-07-28 | 中国石油化工股份有限公司 | Mfi晶体结构铬硅分子筛的合成方法 |
| DE10135296A1 (de) | 2001-07-19 | 2003-01-30 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| CN1589267A (zh) | 2001-09-21 | 2005-03-02 | 住友化学工业株式会社 | 环氧丙烷的制造方法 |
| DE10233382A1 (de) | 2002-07-23 | 2004-01-29 | Basf Ag | Verfahren zur kontinuierlich betriebenen Reindestillation des bei der koppel-produktfreien Synthese von Propylenoxid anfallenden 1.2-Propylenglykols |
| DE10240129B4 (de) | 2002-08-30 | 2004-11-11 | Basf Ag | Integriertes Verfahren zur Synthese von Propylenoxid |
| US6960671B2 (en) | 2002-09-20 | 2005-11-01 | Arco Chemical Technology, L.P. | Process for direct oxidation of propylene to propylene oxide and large particle size titanium silicalite catalysts for use therein |
| EP1424331A1 (en) * | 2002-11-26 | 2004-06-02 | Degussa AG | Process for the epoxidation of olefins |
| DE10317519A1 (de) | 2003-04-16 | 2004-11-04 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| US6884898B1 (en) | 2003-12-08 | 2005-04-26 | Arco Chemical Technology, L.P. | Propylene oxide process |
| US6867312B1 (en) | 2004-03-17 | 2005-03-15 | Arco Chemical Technology, L.P. | Propylene oxide process |
-
2011
- 2011-03-16 TW TW100108896A patent/TWI523689B/zh not_active IP Right Cessation
- 2011-03-22 US US13/637,072 patent/US8703983B2/en not_active Expired - Fee Related
- 2011-03-22 JP JP2013501249A patent/JP2013523633A/ja active Pending
- 2011-03-22 BR BR112012024298A patent/BR112012024298A8/pt not_active IP Right Cessation
- 2011-03-22 CN CN2011800160999A patent/CN102822158A/zh active Pending
- 2011-03-22 WO PCT/US2011/000523 patent/WO2011119217A1/en not_active Ceased
- 2011-03-22 KR KR1020127027601A patent/KR20130040190A/ko not_active Ceased
- 2011-03-22 EP EP11713535A patent/EP2550259A1/en not_active Withdrawn
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5951273A (ja) * | 1982-07-28 | 1984-03-24 | エニーケム・シンテシース・エセ・ピ・ア | オレフイン化合物のエポキシ化法 |
| JPS62185081A (ja) * | 1986-01-28 | 1987-08-13 | エニリチェルケ・エセ・ピ・ア | オレフイン化合物のエポキシ化法 |
| JPH1025285A (ja) * | 1996-07-08 | 1998-01-27 | Mitsubishi Gas Chem Co Inc | オレフィン化合物のエポキシ化法 |
| JPH1180144A (ja) * | 1997-09-04 | 1999-03-26 | Daiso Co Ltd | オレフィンの選択的エポキシ化法 |
| JP2001509821A (ja) * | 1998-03-26 | 2001-07-24 | レプソル キミカ，ソシエダ アノニマ | 溶媒の存在下での過酸化水素によるオレフィン性化合物のエポキシ化方法 |
| JP2005511524A (ja) * | 2001-10-09 | 2005-04-28 | アルコ ケミカル テクノロジィ， エル．ピー． | 前処理したチタンゼオライトを使用する直接エポキシ化方法 |
| JP2008502476A (ja) * | 2004-06-14 | 2008-01-31 | ライオンデル ケミカル テクノロジー、 エル．ピー． | 触媒の再生方法 |
| JP2008524214A (ja) * | 2004-12-17 | 2008-07-10 | ライオンデル ケミカル テクノロジー、 エル．ピー． | チタンまたはバナジウムゼオライト触媒をアミノ多塩基酸で前処理するエポキシ化方法 |
| WO2007013739A1 (en) * | 2005-07-27 | 2007-02-01 | Sk Energy Co., Ltd. | Method of regeneration of titanium-containing molecular sieve catalyst |
| JP2013523422A (ja) * | 2010-03-25 | 2013-06-17 | ダウ グローバル テクノロジーズ エルエルシー | 前処理されたエポキシ化触媒及びそれによりオレフィンを製造する方法 |
Non-Patent Citations (1)
| Title |
|---|
| JPN6015012033; Ｊｏｕｒｎａｌ ｏｆ Ｃａｔａｌｙｓｉｓ Ｖｏｌ．２０４, 2001, ｐ．４０２-４０８ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017524706A (ja) * | 2014-07-29 | 2017-08-31 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | オレフィンをエポキシ化するための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20130040190A (ko) | 2013-04-23 |
| EP2550259A1 (en) | 2013-01-30 |
| TWI523689B (zh) | 2016-03-01 |
| BR112012024298A2 (pt) | 2015-09-15 |
| WO2011119217A1 (en) | 2011-09-29 |
| TW201138968A (en) | 2011-11-16 |
| US20130018196A1 (en) | 2013-01-17 |
| CN102822158A (zh) | 2012-12-12 |
| BR112012024298A8 (pt) | 2017-03-21 |
| US8703983B2 (en) | 2014-04-22 |
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