JP2007516976A5 - - Google Patents
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- JP2007516976A5 JP2007516976A5 JP2006544436A JP2006544436A JP2007516976A5 JP 2007516976 A5 JP2007516976 A5 JP 2007516976A5 JP 2006544436 A JP2006544436 A JP 2006544436A JP 2006544436 A JP2006544436 A JP 2006544436A JP 2007516976 A5 JP2007516976 A5 JP 2007516976A5
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- JP
- Japan
- Prior art keywords
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- carbon atoms
- monovalent
- substituted
- general formula
- 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.)
- Granted
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000012074 organic phase Substances 0.000 claims 3
- 125000004437 phosphorous atom Chemical group 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- -1 2 -phospha-tricyclo [3.3.1.1 {3,7}] decyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229910052703 rhodium Inorganic materials 0.000 claims 2
- 239000010948 rhodium Substances 0.000 claims 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000008098 formaldehyde solution Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- HDIJZFORGDBEKL-UHFFFAOYSA-N 2,3,4-trimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(C)=C1C HDIJZFORGDBEKL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 2
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 description 2
- QFCSTMJALGVENX-UHFFFAOYSA-N 1,3,5,7-tetramethyl-8-octyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane Chemical compound CC12OC3(CC(OC(C1)(P3CCCCCCCC)C)(O2)C)C QFCSTMJALGVENX-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03257883 | 2003-12-16 | ||
| PCT/EP2004/053492 WO2005058788A1 (en) | 2003-12-16 | 2004-12-15 | Process of preparing glycolaldehyde |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007516976A JP2007516976A (ja) | 2007-06-28 |
| JP2007516976A5 true JP2007516976A5 (enExample) | 2009-04-09 |
| JP4474419B2 JP4474419B2 (ja) | 2010-06-02 |
Family
ID=34684623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006544436A Expired - Lifetime JP4474419B2 (ja) | 2003-12-16 | 2004-12-15 | グリコールアルデヒドの調製方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7449607B2 (enExample) |
| EP (1) | EP1697291A1 (enExample) |
| JP (1) | JP4474419B2 (enExample) |
| KR (1) | KR20060117345A (enExample) |
| CN (1) | CN100434412C (enExample) |
| AU (1) | AU2004298446B2 (enExample) |
| BR (1) | BRPI0417643A (enExample) |
| CA (1) | CA2549456A1 (enExample) |
| MX (1) | MXPA06006705A (enExample) |
| RU (1) | RU2371429C2 (enExample) |
| WO (1) | WO2005058788A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7858787B2 (en) * | 2006-09-22 | 2010-12-28 | Shell Oil Company | Process for producing olefins |
| US7301054B1 (en) | 2006-09-29 | 2007-11-27 | Eastman Chemical Company | Process for the preparation of glycolaldehyde |
| US7420093B2 (en) | 2006-09-29 | 2008-09-02 | Eastman Chemical Company | Process for the preparation of glycolaldehyde |
| US7674937B2 (en) | 2008-05-28 | 2010-03-09 | Eastman Chemical Company | Hydroformylation catalysts |
| FR2943061B1 (fr) * | 2009-03-13 | 2011-02-25 | Rhodia Operations | Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation ou d'hydroformylation utilisant ces systemes catalytiques |
| CN102939278B (zh) | 2009-12-17 | 2014-11-26 | 巴斯夫欧洲公司 | 制备高级乙醇胺类的方法 |
| RU2573570C2 (ru) | 2009-12-17 | 2016-01-20 | Басф Се | Превращение гликолевого альдегида со средством аминирования |
| CN101811933B (zh) * | 2010-04-26 | 2013-05-08 | 常州大学 | 一种催化合成乙二醇的方法 |
| TWI508937B (zh) * | 2014-04-30 | 2015-11-21 | Chien An Chen | 使用甲醇為原料經由甲醛、乙醇醛的中間產物而合成乙二醇的製造方法 |
| CN105085211B (zh) * | 2014-05-16 | 2017-09-05 | 陈建安 | 一种甲醛、乙醇醛及乙二醇的制造方法 |
| MY184090A (en) * | 2014-05-19 | 2021-03-17 | Iowa Corn Promotion Board | Process for the continuous production of ethylene glycol from carbohydrates |
| EP3160927B1 (en) | 2014-06-30 | 2022-04-13 | Haldor Topsøe A/S | Process for the preparation of ethylene glycol from sugars |
| EP3400207B1 (en) | 2016-01-07 | 2023-06-07 | Topsoe A/S | Process for the preparation of ethylene glycol from sugars |
| CN108473401B (zh) * | 2016-01-07 | 2021-08-27 | 托普索公司 | 从糖类制备乙二醇的方法 |
| CN105618035B (zh) * | 2016-02-02 | 2018-05-11 | 中国科学院福建物质结构研究所 | 合成气制备乙醇醛所用的负载型铑催化剂及其制备方法 |
| CN109790098A (zh) | 2016-12-08 | 2019-05-21 | 托普索公司 | 通过热解碎裂生产乙醇醛 |
| GB201904612D0 (en) | 2019-04-02 | 2019-05-15 | Univ Leuven Kath | Reaction of glycoladehyde |
| WO2020095147A1 (en) * | 2018-11-07 | 2020-05-14 | Sabic Global Technologies B.V. | Catalyst systems and methods for their use in selective hydroformylation of formaldehyde to glycolaldehyde |
| WO2020249428A1 (en) | 2019-06-11 | 2020-12-17 | Basf Se | Products obtained by the conversion of glycolaldehyde derivatives and aminating agents and their conversion to ethyleneamines and ethanolamines |
| WO2020249426A1 (en) | 2019-06-11 | 2020-12-17 | Basf Se | Conversion of glycolaldehyde with an aminating agent |
| WO2020249427A1 (en) | 2019-06-11 | 2020-12-17 | Basf Se | Gas-phase process for the conversion of glycolaldehyde with an aminating agent |
| CN112337508A (zh) * | 2020-11-03 | 2021-02-09 | 中国科学院福建物质结构研究所 | 一种乙醇醛合成用铑基催化剂及其制备方法 |
| DE202021103519U1 (de) | 2021-07-01 | 2021-07-16 | Schill + Seilacher Gmbh | Gerbmittel, Verwendung des Gerbmittels zum Gerben von Tierhäuten und Fellen und daraus erhaltenes Leder |
| ES2975566T3 (es) | 2021-07-01 | 2024-07-09 | Schill Seilacher Gmbh | Agente curtiente, uso de un curtiente y procedimiento de curtido de pieles de animales y del cuero obtenido a partir de las mismas |
| CN114751813B (zh) * | 2022-05-05 | 2023-12-15 | 天津大学 | 一种甲醛氢甲酰化制备乙醇醛的方法 |
| CN115108887A (zh) * | 2022-08-18 | 2022-09-27 | 山东能源集团有限公司 | 一种乙二醇的制备方法 |
| CN115340440B (zh) * | 2022-08-18 | 2024-09-06 | 山东能源集团有限公司 | 一种制备乙二醇的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026327A (en) | 1960-07-06 | 1962-03-20 | American Cyanamid Co | Substituted 1, 3, 5, 7-tetraalkyl-2, 6, 9-trioxa-10-phosphatricyclo [3.3.1.1.3,7] decanes |
| US4414421A (en) * | 1981-08-03 | 1983-11-08 | Shell Oil Company | Process for the preparation of glycol aldehyde |
| US4608444A (en) * | 1984-04-05 | 1986-08-26 | The Halcon Sd Group, Inc. | Process and accompanying catalysts for the hydroformylation of formaldehyde to glycol-aldehyde |
| US4847423A (en) * | 1988-03-03 | 1989-07-11 | Hoechst Celanese Corporation | Hydroformylation of aqueous formaldehyde using a rhodium-tricyclohexylphosphine catalyst system |
| SU1608182A1 (ru) * | 1988-09-15 | 1990-11-23 | Предприятие П/Я В-2287 | Способ получени гликолевого альдегида |
| US5567856A (en) * | 1995-05-30 | 1996-10-22 | Hoechst Celanese Corporation | Synthesis of and hydroformylation with fluoro-substituted bidentate phosphine ligands |
| US6156934A (en) * | 1997-03-26 | 2000-12-05 | Shell Oil Company | Diphosphines |
| DE10023468A1 (de) * | 2000-05-12 | 2001-11-15 | Basf Ag | Verfahren zur Hydroformylierung ethylenisch ungesättigter Verbindungen und Ligand-Metall-Komplex als Katalysator hierfür |
-
2004
- 2004-12-15 JP JP2006544436A patent/JP4474419B2/ja not_active Expired - Lifetime
- 2004-12-15 WO PCT/EP2004/053492 patent/WO2005058788A1/en not_active Ceased
- 2004-12-15 RU RU2006125408/04A patent/RU2371429C2/ru not_active IP Right Cessation
- 2004-12-15 EP EP04804845A patent/EP1697291A1/en not_active Withdrawn
- 2004-12-15 AU AU2004298446A patent/AU2004298446B2/en not_active Ceased
- 2004-12-15 US US10/583,109 patent/US7449607B2/en not_active Expired - Fee Related
- 2004-12-15 KR KR1020067012776A patent/KR20060117345A/ko not_active Ceased
- 2004-12-15 CA CA002549456A patent/CA2549456A1/en not_active Abandoned
- 2004-12-15 CN CNB2004800376940A patent/CN100434412C/zh not_active Expired - Lifetime
- 2004-12-15 BR BRPI0417643-0A patent/BRPI0417643A/pt not_active IP Right Cessation
- 2004-12-15 MX MXPA06006705A patent/MXPA06006705A/es active IP Right Grant
-
2008
- 2008-09-10 US US12/208,149 patent/US7511178B2/en not_active Expired - Fee Related
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