ES2506440T3 - Procedimiento para la preparación de polioles de carbonato de poliéter - Google Patents
Procedimiento para la preparación de polioles de carbonato de poliéter Download PDFInfo
- Publication number
- ES2506440T3 ES2506440T3 ES11757815.3T ES11757815T ES2506440T3 ES 2506440 T3 ES2506440 T3 ES 2506440T3 ES 11757815 T ES11757815 T ES 11757815T ES 2506440 T3 ES2506440 T3 ES 2506440T3
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- polyether carbonate
- carbonate polyols
- procedure
- methyl
- 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.)
- Active
Links
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract description 4
- 229920000570 polyether Polymers 0.000 title abstract description 4
- -1 carbonate polyols Chemical class 0.000 title abstract description 3
- 229920005862 polyol Polymers 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 230000000536 complexating effect Effects 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/18—Block or graft polymers
- C08G64/183—Block or graft polymers containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010040517A DE102010040517A1 (de) | 2010-09-09 | 2010-09-09 | Verfahren zur Herstellung von Polyetherpolyolen |
| DE102010040517 | 2010-09-09 | ||
| PCT/EP2011/065364 WO2012032028A1 (de) | 2010-09-09 | 2011-09-06 | Verfahren zur herstellung von polyethercarbonatpolyolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2506440T3 true ES2506440T3 (es) | 2014-10-13 |
Family
ID=44653291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11757815.3T Active ES2506440T3 (es) | 2010-09-09 | 2011-09-06 | Procedimiento para la preparación de polioles de carbonato de poliéter |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9045592B2 (enExample) |
| EP (1) | EP2614102B1 (enExample) |
| JP (1) | JP5792310B2 (enExample) |
| KR (1) | KR20130102588A (enExample) |
| CN (1) | CN103189417B (enExample) |
| BR (1) | BR112013005783A2 (enExample) |
| CA (1) | CA2810559A1 (enExample) |
| DE (1) | DE102010040517A1 (enExample) |
| ES (1) | ES2506440T3 (enExample) |
| MX (1) | MX2013002484A (enExample) |
| RU (1) | RU2013115633A (enExample) |
| SG (1) | SG188278A1 (enExample) |
| WO (1) | WO2012032028A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2548908A1 (de) * | 2011-07-18 | 2013-01-23 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyetherpolyolen |
| WO2014198689A1 (de) * | 2013-06-13 | 2014-12-18 | Bayer Materialscience Ag | Polyethercarbonat-polyoxymethylen-block-copolymere |
| EP2837648A1 (en) | 2013-08-12 | 2015-02-18 | Repsol, S.A. | Process for preparing polyether carbonate polyols |
| EP2845871A1 (de) * | 2013-09-05 | 2015-03-11 | Bayer MaterialScience AG | Vernetzung von Doppelbindungen enthaltenden Polyethercarbonatpolyolen durch Addition von Mercaptanen |
| EP2865700A1 (de) * | 2013-10-23 | 2015-04-29 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen |
| US9527958B2 (en) | 2014-05-02 | 2016-12-27 | Covestro Llc | Process for purification of polyether carbonate polyols |
| CN106471040B (zh) * | 2014-07-03 | 2019-05-14 | 科思创德国股份有限公司 | 制备聚醚碳酸酯多元醇的方法 |
| US10119223B2 (en) | 2016-07-15 | 2018-11-06 | Covestro Llc | Carpet and synthetic turf backings prepared from a polyether carbonate polyol |
| US10040903B2 (en) | 2016-09-13 | 2018-08-07 | Covestro Llc | Polymer polyol quality |
| PL3538588T3 (pl) | 2016-11-11 | 2023-04-11 | Dow Global Technologies Llc | Poliole na bazie poliwęglanu |
| GB201703323D0 (en) * | 2017-03-01 | 2017-04-12 | Econic Tech Ltd | Method for preparing polyols |
| CN110964191B (zh) * | 2018-09-29 | 2021-02-02 | 杭州普力材料科技有限公司 | 一种混合酸改性的锌钴双金属氰化物催化剂及其制备方法 |
| US20220315698A1 (en) * | 2019-07-31 | 2022-10-06 | Covestro Deutschland Ag | Method for producing polyether carbonate polyols |
| EP4093539B1 (de) * | 2020-01-21 | 2023-10-04 | Covestro Deutschland AG | Verfahren zur herstellung von doppelmetallcyanid-katalysatoren |
| KR102717144B1 (ko) * | 2021-07-15 | 2024-10-11 | 아주대학교산학협력단 | 하이드로젠 헥사시아노코발테이트와 아연 카복실레이트의 조합으로 제조된 더블메탈시아나이드 촉매 및 이를 이용한 프로필렌 옥사이드 중합 |
| WO2023038406A1 (ko) | 2021-09-08 | 2023-03-16 | 주식회사 엘지화학 | 이중 금속 시아나이드 촉매, 이의 제조방법 및 상기 촉매를 이용한 폴리알킬렌 카보네이트의 제조방법 |
| CN114524929B (zh) * | 2021-09-24 | 2023-07-25 | 山东联欣环保科技有限公司 | 一种二氧化碳基四元共聚物的制备方法 |
| WO2023054999A1 (ko) * | 2021-09-29 | 2023-04-06 | 주식회사 엘지화학 | 폴리알킬렌 카보네이트 수지의 제조방법 |
| CN114381252B (zh) * | 2022-01-19 | 2023-02-10 | 成都理工大学 | 一种超高温下耐多价金属阳离子无固相修井液的制备方法 |
| EP4768514A1 (en) | 2024-12-30 | 2026-07-01 | Covestro LLC | POLYOLS, POLYMERS AND PROCESSES FOR THEIR PREPARATION |
| EP4768515A1 (en) | 2024-12-30 | 2026-07-01 | Covestro LLC | POLYOLS, POLYMERS AND PREPARATION PROCESSES |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
| JP2653236B2 (ja) | 1990-10-05 | 1997-09-17 | 旭硝子株式会社 | ポリエーテル化合物の製造方法 |
| US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| US5482908A (en) | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| ID24172A (id) * | 1997-10-13 | 2000-07-13 | Bayer Ag | Katalis logam ganda yang sangat aktif untuk memproduksi poliol-poliol poliester |
| US6376645B1 (en) | 1999-07-09 | 2002-04-23 | The Dow Chemical Company | Complexing agent-modified hexacyanometallate hexanitrometallate catalysts |
| DE19958355A1 (de) | 1999-12-03 | 2001-06-07 | Bayer Ag | Verfahren zur Herstellung von DMC-Katalysatoren |
| WO2001080994A1 (de) | 2000-04-20 | 2001-11-01 | Bayer Aktiengesellschaft | Verfahren zur herstellung von dmc-katalysatoren |
| DE10122019A1 (de) | 2001-05-07 | 2002-11-14 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE10147712A1 (de) | 2001-09-27 | 2003-04-17 | Basf Ag | Verfahren zur Herstellung aliphatischer Polycarbonate |
| US6762278B2 (en) | 2002-02-04 | 2004-07-13 | Basf Corporation | Process for the copolymerization of alkylene oxides and carbon dioxide using suspensions of multi-metal cyanide compounds |
| DE10219028A1 (de) | 2002-04-29 | 2003-11-06 | Bayer Ag | Herstellung und Verwendung von hochmolekularen aliphatischen Polycarbonaten |
| ES2400709T3 (es) * | 2002-11-07 | 2013-04-11 | Dow Global Technologies Inc. | Método para preparar catalizadores de cianuro metálico usando agentes complejantes polimerizables |
| MXPA05009512A (es) | 2003-03-07 | 2006-02-22 | Dow Global Technologies Inc | Proceso continuo y sistema para producir polioles de polieter. |
| US20050101477A1 (en) | 2003-11-07 | 2005-05-12 | George Combs | Unsaturated tertiary alcohols as ligands for active dmc catalysts |
| US20060223973A1 (en) | 2005-03-29 | 2006-10-05 | Basf Corporation | Method of forming a polyethercarbonate polyol |
| US7977501B2 (en) | 2006-07-24 | 2011-07-12 | Bayer Materialscience Llc | Polyether carbonate polyols made via double metal cyanide (DMC) catalysis |
-
2010
- 2010-09-09 DE DE102010040517A patent/DE102010040517A1/de not_active Withdrawn
-
2011
- 2011-09-06 RU RU2013115633/04A patent/RU2013115633A/ru not_active Application Discontinuation
- 2011-09-06 BR BR112013005783A patent/BR112013005783A2/pt unknown
- 2011-09-06 CA CA2810559A patent/CA2810559A1/en not_active Abandoned
- 2011-09-06 JP JP2013527572A patent/JP5792310B2/ja not_active Expired - Fee Related
- 2011-09-06 KR KR1020137008882A patent/KR20130102588A/ko not_active Ceased
- 2011-09-06 MX MX2013002484A patent/MX2013002484A/es active IP Right Grant
- 2011-09-06 CN CN201180043627.XA patent/CN103189417B/zh not_active Expired - Fee Related
- 2011-09-06 SG SG2013013461A patent/SG188278A1/en unknown
- 2011-09-06 WO PCT/EP2011/065364 patent/WO2012032028A1/de not_active Ceased
- 2011-09-06 US US13/821,254 patent/US9045592B2/en active Active
- 2011-09-06 ES ES11757815.3T patent/ES2506440T3/es active Active
- 2011-09-06 EP EP11757815.3A patent/EP2614102B1/de not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| JP5792310B2 (ja) | 2015-10-07 |
| EP2614102B1 (de) | 2014-07-23 |
| SG188278A1 (en) | 2013-04-30 |
| CN103189417A (zh) | 2013-07-03 |
| JP2013537245A (ja) | 2013-09-30 |
| BR112013005783A2 (pt) | 2017-03-21 |
| EP2614102A1 (de) | 2013-07-17 |
| CA2810559A1 (en) | 2012-03-15 |
| US20130184432A1 (en) | 2013-07-18 |
| MX2013002484A (es) | 2013-04-03 |
| US9045592B2 (en) | 2015-06-02 |
| KR20130102588A (ko) | 2013-09-17 |
| WO2012032028A1 (de) | 2012-03-15 |
| RU2013115633A (ru) | 2014-10-20 |
| DE102010040517A1 (de) | 2012-03-15 |
| CN103189417B (zh) | 2016-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2013002484A (es) | Procedimiento para la preparacion de polioles de carbonato de polieter. | |
| ES2536206T3 (es) | Parche medicinal | |
| ES2647148T3 (es) | Procedimiento para la producción de ésteres insaturados partiendo de aldehídos mediante esterificación oxidativa directa | |
| AR094543A1 (es) | Método para producir metacrilato de metilo a partir de propionaldehído y formaldehído mediante esterificación oxidativa | |
| ES2555989T3 (es) | Procedimiento para la síntesis del ácido 2,5-furanodicarboxílico | |
| AR084770A1 (es) | Absorcion de oxigeno y dioxido de carbono en un recipiente de un solo uso con un soporte absorbente debajo del filtro | |
| MX2013003724A (es) | Procedimiento para la produccion de polioletercarbonatos. | |
| ES2542780T3 (es) | Agente acelerante para curar resinas | |
| ES2578704B1 (es) | Procedimiento para la reducción de dióxido de carbono a metano mediante catalizador activado por plasma DBD | |
| CL2012000014A1 (es) | Metodo para fabricar acido acetico que comprende hacer reaccionar metanol con monoxido de carbono (co) y catalizador homogeneo de metal del grupo viii y un promotor de yoduro, retirar la mezcla y alimentarla junto con adicionar a un recipiente prevaporizador, evacuar fracciones livianas y consumir acetato de metilo. | |
| EP4234068A3 (en) | Self-concentrating absorbent for acid gas separation | |
| BR112019008268A2 (pt) | processo em semibatelada para produção de polióis policarbonato por meio de copolimerização de dióxido de carbono e de um oxirano | |
| AR071254A1 (es) | Proceso de preparacion de glicol alquileno | |
| WO2013087582A3 (de) | Verfahren zur herstellung von polyetherestercarbonatpolyolen | |
| CL2011003115A1 (es) | Producto farmaceutico solido para el diagnostico del cancer, afecciones precancerosas y afecciones no cancerosas en el tracto gastrointestinal inferior que comprende a) acido 5-aminolevulinico (5-ala), un precursor de 5-ala o un derivado de 5-ala, b) uno o mas trigliceridos y c) uno o mas emulsionadores. | |
| AR073185A1 (es) | Proceso para la produccion de hidroxido de magnesio de alta pureza | |
| MX2014000637A (es) | Procedimiento para la preparacion de polioleteres. | |
| AR069725A1 (es) | Proceso para preparar una composicion de alcoxilato y una composicion alcoxilada | |
| WO2008064076A3 (en) | A process for treating a carrier, a process for preparing a catalyst, the catalyst, and use of the catalyst | |
| MY161602A (en) | PRODUCING a,B-UNSATURATED ALDEHYDES BY MEANS OF A REACTION MIXING PUMP | |
| MX2015007902A (es) | Recuperacion y uso de acidos carboxilicos procedentes de un caldo de fermentacion. | |
| BR112015022467A2 (pt) | poliéteres ativos, de cadeia longa, catalisador por base a partir de iniciadores catalisados por dmc de cadeia curta | |
| CL2011003337A1 (es) | Proceso para la obtencion del 2-metiltiopropionato de s-[2-[1-(2-etilbutil)-ciclohexilcarbonilamino)-fenilo] por reduccion de un disulfuro en presencia de anhidrido isobutirico. | |
| AR067614A1 (es) | Destilacion azeotropica con regeneracion del agente de arrastre | |
| MY173010A (en) | Process for preparing a carboxylic acid from a diol or from an epoxide by oxidaive cleavage |