JP2001509821A - 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 - Google Patents
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Info
- Publication number
- JP2001509821A JP2001509821A JP54779899A JP54779899A JP2001509821A JP 2001509821 A JP2001509821 A JP 2001509821A JP 54779899 A JP54779899 A JP 54779899A JP 54779899 A JP54779899 A JP 54779899A JP 2001509821 A JP2001509821 A JP 2001509821A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- hydrogen peroxide
- epoxidation
- weight
- solvent
- 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.)
- Withdrawn
Links
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- 239000010457 zeolite Substances 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004680 hydrogen peroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
Classifications
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- 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
- 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
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.溶媒(solvents)の存在下、約50°〜140℃の範囲の温度での過酸化 水素によるオレフィン性化合物の炭素−炭素二重結合の液相における液相エポキ シ化方法であって、シリカで支持されたチタン触媒を使用し、その触媒が、比表 面積50〜900m2/gの範囲のシリカを、酸素化された有機溶媒中でチタン アルコキシドおよび/又はチタノセンの溶液で含浸し、次いで過剰の溶液および 溶媒を分離することによってによって製造されることを特徴とする方法。 2.前記酸素化された有機溶媒が、C1〜C8アルコールであることを特徴とす る請求項1に従う方法。 3.含浸によって、約0.01〜0.1重量%(100gの触媒当たりのアル カリまたはアルカリ土類金属の重さ)の範囲の量のアルカリまたはアルカリ土類 金属塩が、前記触媒に加えられることを特徴とする請求項1および2に従う方法 。 4.有機溶媒中の約1〜15重量%の範囲の濃度で過酸化水素溶液を用いるこ とを特徴とする請求項1〜3に従う方法。 5.第二級アルコールを分子状酸素または空気で酸化することによって得られ る過酸化水素溶液を用いることを特徴とする請求項4に従う方法。 6.前記オレフィン性化合物がアルケンまたはシクロアルケンであることを特 徴とする請求項1〜5に従う方法。 7.前記アルケンがプロピレンであることを特徴とする請求項6に従う方法。 8.前記シクロアルケンがシクロヘキセンであることを特徴とする請求項6に 従う方法。 9.前記オレフィン性化合物がアリルアルコールであることを特徴とする請求 項6に従う方法。 10.前記オレフィン性化合物がフマル酸またはマレイン酸、またはそのエス テル、無水物または混合物の一つであることを特徴とする請求項6に従う方法。 11.C6〜C9芳香族アルコールまたはC1〜C6脂肪族アルコールをエポキシ 化反応において溶媒として用いることを特徴とする請求項1〜10に従う方法。 12.前記有機溶媒が、2−メチル−2−プロパノール、または2−メチル− 2プロパノールを含む有機溶媒の混合物であることを特徴とする請求項11に従 う方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/ES1998/000078 WO1999048884A1 (es) | 1998-03-26 | 1998-03-26 | Procedimiento de epoxidacion de compuestos olefinicos con peroxido de hidrogeno |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006285483A Division JP2007031449A (ja) | 2006-10-19 | 2006-10-19 | 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 |
Publications (1)
Publication Number | Publication Date |
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JP2001509821A true JP2001509821A (ja) | 2001-07-24 |
Family
ID=8302428
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP54779899A Withdrawn JP2001509821A (ja) | 1998-03-26 | 1998-03-26 | 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 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6160138A (ja) |
EP (1) | EP0987259B1 (ja) |
JP (1) | JP2001509821A (ja) |
KR (1) | KR100429675B1 (ja) |
DE (1) | DE69806155T2 (ja) |
ES (1) | ES2178825T3 (ja) |
PT (1) | PT987259E (ja) |
WO (1) | WO1999048884A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002273221A (ja) * | 2001-01-15 | 2002-09-24 | Maruzen Petrochem Co Ltd | チタン含有固体触媒及びこれを用いたエポキシ化合物の製造法 |
JP2013523633A (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を使用してプロピレンオキシドを製造する方法 |
KR20180086232A (ko) * | 2015-11-26 | 2018-07-30 | 에보닉 데구사 게엠베하 | 올레핀의 에폭시화 방법 |
Families Citing this family (19)
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US6369245B1 (en) * | 1999-08-13 | 2002-04-09 | Colorado State University Research Foundation | Epoxidation of olefins |
US6686483B2 (en) | 1996-10-08 | 2004-02-03 | Colorado State University Research Foundation | Catalytic asymmetric epoxidation |
WO1999052886A1 (en) | 1998-04-16 | 1999-10-21 | Colorado State University Research Foundation | Kinetic resolution of olefins |
DE19926725A1 (de) * | 1999-06-11 | 2000-12-14 | Basf Ag | Verfahren zur Umsetzung organischer Verbindungen mit Wasserstoffperoxid |
IT1313572B1 (it) * | 1999-07-27 | 2002-09-09 | Enichem Spa | Procedimento per la preparazione di epossidi. |
EP1074548B1 (en) * | 1999-08-06 | 2006-01-11 | Repsol Quimica S.A. | A method for continuous production of propylene oxide and other alkene oxides |
JP3920020B2 (ja) * | 1999-12-24 | 2007-05-30 | 株式会社日本触媒 | 含酸素有機化合物製造用触媒および含酸素有機化合物の製造方法 |
EP1195368A3 (en) | 2000-09-25 | 2002-05-15 | Haldor Topsoe A/S | Process for the catalytic selective oxidation of a hydrocarbon compound in presence of mesoporous zeolite |
JP2002145872A (ja) * | 2000-11-01 | 2002-05-22 | Maruzen Petrochem Co Ltd | エポキシ化合物の製造方法 |
US6485949B1 (en) | 2001-01-29 | 2002-11-26 | The United States Of America As Represented By The Secretary Of Agriculture | Epoxidation of carbon-carbon double bond with membrane bound peroxygenase |
EP1344747B1 (en) | 2002-03-14 | 2012-02-08 | Repsol Quimica S.A. | Process to obtain hydrogen peroxide |
DE10247495A1 (de) | 2002-10-11 | 2004-04-22 | Degussa Ag | Verfahren zur Epoxidierung cyclischer Alkene |
DE10247496A1 (de) | 2002-10-11 | 2004-04-22 | Degussa Ag | Verwendung eines Absatzbeschleunigers bei der Epoxidierung |
PT1443020E (pt) | 2003-02-03 | 2010-04-08 | Repsol Quimica Sa | Processo integrado para oxidação selectiva de compostos orgânicos |
US20050277542A1 (en) * | 2004-06-14 | 2005-12-15 | Kaminsky Mark P | Catalyst regeneration process |
KR100905678B1 (ko) | 2005-02-18 | 2009-07-03 | 도쿠리쓰교세이호징 가가쿠 기주쓰 신코 기코 | 광학 활성 에폭시 화합물의 제조 방법, 및 상기 방법에사용하기 위한 착체 및 그의 제조 방법 |
CN103288991B (zh) * | 2013-05-29 | 2015-10-28 | 西北师范大学 | 以环氧基为功能基团的共价连接载体及其制备方法 |
US10858456B1 (en) * | 2019-06-12 | 2020-12-08 | Chevron Phillips Chemical Company Lp | Aqueous titanation of Cr/silica catalysts by the use of acetylacetonate and another ligand |
US11242416B2 (en) | 2019-06-12 | 2022-02-08 | Chevron Phillips Chemical Company Lp | Amino acid chelates of titanium and use thereof in aqueous titanation of polymerization catalysts |
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IT1187661B (it) * | 1985-04-23 | 1987-12-23 | Enichem Sintesi | Catalizzatore a base di silicio e titanio ad elevata resistenza meccanica |
ES2033693T3 (es) * | 1986-01-28 | 1993-04-01 | Eniricerche S.P.A. | Un procedimiento para la exposidacion de compuestos olefinicos. |
US5262550A (en) * | 1992-04-30 | 1993-11-16 | Arco Chemical Technology, L.P. | Epoxidation process using titanium-rich silicalite catalysts |
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FR2704159B1 (fr) * | 1993-04-22 | 1995-06-09 | Atochem Elf Sa | Catalyseur solide à base de silice particulaire, comportant du titane, Procédé d'obtention, et utilisation dans l'époxydation d'oléfines. |
US5374747A (en) * | 1993-12-23 | 1994-12-20 | Arco Chemical Technology, L.P. | Epoxidation process and catalyst therefore |
US5453511A (en) * | 1993-12-23 | 1995-09-26 | Arco Chemical Technology, L.P. | Bis-piperidinium compounds |
US5463090A (en) * | 1994-10-27 | 1995-10-31 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
US5646314A (en) * | 1994-11-16 | 1997-07-08 | Arco Chemical Technology, L.P. | Process for titanium silicalite-catalyzed epoxidation |
US5693834A (en) * | 1995-03-15 | 1997-12-02 | Arco Chemical Technology, L.P. | Integrated process for epoxidation |
JP3658790B2 (ja) * | 1995-03-30 | 2005-06-08 | 住友化学株式会社 | 触媒及びオキシラン化合物の製造方法 |
US5753576A (en) * | 1995-05-18 | 1998-05-19 | Arco Chemical Technology, L.P. | Regeneration of a titanium-containing molecular sieve |
FR2743061A1 (fr) * | 1995-12-27 | 1997-07-04 | Atochem Elf Sa | Procede d'obtention d'un solide a base de silice et de titane et utilisation de ce solide notamment dans l'epoxydation des olefines. |
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1998
- 1998-03-26 PT PT98910745T patent/PT987259E/pt unknown
- 1998-03-26 JP JP54779899A patent/JP2001509821A/ja not_active Withdrawn
- 1998-03-26 DE DE69806155T patent/DE69806155T2/de not_active Expired - Fee Related
- 1998-03-26 KR KR10-1999-7010900A patent/KR100429675B1/ko not_active IP Right Cessation
- 1998-03-26 US US09/424,572 patent/US6160138A/en not_active Expired - Fee Related
- 1998-03-26 EP EP98910745A patent/EP0987259B1/en not_active Expired - Lifetime
- 1998-03-26 ES ES98910745T patent/ES2178825T3/es not_active Expired - Lifetime
- 1998-03-26 WO PCT/ES1998/000078 patent/WO1999048884A1/es active IP Right Grant
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2002273221A (ja) * | 2001-01-15 | 2002-09-24 | Maruzen Petrochem Co Ltd | チタン含有固体触媒及びこれを用いたエポキシ化合物の製造法 |
JP4694712B2 (ja) * | 2001-01-15 | 2011-06-08 | 丸善石油化学株式会社 | チタン含有固体触媒及びこれを用いたエポキシ化合物の製造法 |
JP2013523633A (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を使用してプロピレンオキシドを製造する方法 |
KR20180086232A (ko) * | 2015-11-26 | 2018-07-30 | 에보닉 데구사 게엠베하 | 올레핀의 에폭시화 방법 |
KR102642647B1 (ko) | 2015-11-26 | 2024-02-29 | 에보닉 오퍼레이션스 게엠베하 | 올레핀의 에폭시화 방법 |
Also Published As
Publication number | Publication date |
---|---|
ES2178825T3 (es) | 2003-01-01 |
KR100429675B1 (ko) | 2004-05-03 |
KR20010012932A (ko) | 2001-02-26 |
WO1999048884A1 (es) | 1999-09-30 |
EP0987259B1 (en) | 2002-06-19 |
EP0987259A1 (en) | 2000-03-22 |
PT987259E (pt) | 2002-11-29 |
US6160138A (en) | 2000-12-12 |
DE69806155D1 (de) | 2002-07-25 |
DE69806155T2 (de) | 2003-02-06 |
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