JP2008515843A5 - - Google Patents
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- JP2008515843A5 JP2008515843A5 JP2007535110A JP2007535110A JP2008515843A5 JP 2008515843 A5 JP2008515843 A5 JP 2008515843A5 JP 2007535110 A JP2007535110 A JP 2007535110A JP 2007535110 A JP2007535110 A JP 2007535110A JP 2008515843 A5 JP2008515843 A5 JP 2008515843A5
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- aryl
- group
- formula
- optionally
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims 8
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 6
- 150000001299 aldehydes Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 150000001728 carbonyl compounds Chemical class 0.000 claims 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 4
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- 229930003633 citronellal Natural products 0.000 claims 3
- 235000000983 citronellal Nutrition 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 229940095045 isopulegol Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940041616 menthol Drugs 0.000 claims 2
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 claims 2
- 125000004437 phosphorous atom Chemical group 0.000 claims 2
- 150000003623 transition metal compounds Chemical class 0.000 claims 2
- 241000134874 Geraniales Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims 1
- 150000002504 iridium compounds Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004049631.5 | 2004-10-11 | ||
| DE102004049631A DE102004049631A1 (de) | 2004-10-11 | 2004-10-11 | Verfahren zur Herstellung optisch aktiver Carbonylverbindungen |
| PCT/EP2005/010847 WO2006040096A1 (de) | 2004-10-11 | 2005-10-08 | Verfahren zur herstellung optisch aktiver carbonylverbindungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008515843A JP2008515843A (ja) | 2008-05-15 |
| JP2008515843A5 true JP2008515843A5 (enExample) | 2012-03-22 |
| JP5128282B2 JP5128282B2 (ja) | 2013-01-23 |
Family
ID=35613864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007535110A Expired - Lifetime JP5128282B2 (ja) | 2004-10-11 | 2005-10-08 | 光学活性カルボニル化合物の製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7534921B2 (enExample) |
| EP (1) | EP1802561B1 (enExample) |
| JP (1) | JP5128282B2 (enExample) |
| CN (1) | CN101039894B (enExample) |
| AT (1) | ATE495143T1 (enExample) |
| DE (2) | DE102004049631A1 (enExample) |
| ES (1) | ES2359837T3 (enExample) |
| WO (1) | WO2006040096A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5090926B2 (ja) * | 2004-12-22 | 2012-12-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | キラルイリジウム錯体を使用するアルケンの不斉水素化 |
| CN101675020B (zh) * | 2007-04-25 | 2013-11-06 | 巴斯夫欧洲公司 | 合成光学活性羰基化合物的方法 |
| AU2008271625A1 (en) * | 2007-07-03 | 2009-01-08 | Sanofi-Aventis | A process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates |
| ES2545271T3 (es) * | 2007-07-23 | 2015-09-09 | Basf Se | Procedimiento para la preparación de mentol mediante hidrogenación de isopulegol |
| EP2225192B1 (de) * | 2007-11-30 | 2017-05-03 | Basf Se | Verfahren zur herstellung von optisch aktivem und racemischem menthol |
| EP2353714A4 (en) | 2008-11-27 | 2012-05-16 | Takasago Perfumery Co Ltd | ASYMMETRIC HYDROGENATION CATALYST |
| CN102458659B (zh) * | 2009-06-03 | 2014-07-09 | 高砂香料工业株式会社 | 不对称氢化催化剂 |
| JP5711209B2 (ja) | 2010-03-04 | 2015-04-30 | 高砂香料工業株式会社 | 均一系不斉水素化触媒 |
| US9000192B2 (en) | 2010-11-29 | 2015-04-07 | Takasago International Corporation | Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same |
| JP5560464B2 (ja) | 2010-11-29 | 2014-07-30 | 高砂香料工業株式会社 | 不斉水素化触媒 |
| JP5780933B2 (ja) | 2010-12-01 | 2015-09-16 | 高砂香料工業株式会社 | 光学活性メントールの製造方法 |
| CN103086858B (zh) * | 2012-12-30 | 2015-03-04 | 浙江工业大学 | 一种3-甲基环戊酮的合成方法 |
| ES2883557T3 (es) | 2014-12-19 | 2021-12-09 | Basf Se | Composición para su uso en un procedimiento para la preparación de compuestos carbonílicos ópticamente activos |
| CN105218335B (zh) * | 2015-10-20 | 2017-06-16 | 万华化学集团股份有限公司 | 一种由柠檬醛不对称催化氢化制备手性香茅醛的方法 |
| CN105330515B (zh) * | 2015-10-20 | 2017-07-21 | 万华化学集团股份有限公司 | 一种光学纯香茅醇的制备方法 |
| US10919921B2 (en) | 2016-05-06 | 2021-02-16 | Basf Se | P-chiral phosphine ligands and use thereof for asymmetric synthesis |
| MY205693A (en) | 2018-09-05 | 2024-11-07 | Basf Se | Reactor for carrying out a gas-liquid two-phase high-pressure reaction with a foaming medium |
| US11529607B2 (en) | 2018-09-05 | 2022-12-20 | Basf Se | Reactor for carrying out a reaction between two non-miscible fluids of different densities |
| WO2020048998A1 (de) | 2018-09-05 | 2020-03-12 | Basf Se | Verfahren zur durchführung einer gas/flüssig-zweiphasigen hochdruckreaktion |
| EP3847151B1 (de) | 2018-09-05 | 2022-11-09 | Basf Se | Kontinuierliche herstellung einer optisch aktiven carbonylverbindung durch asymmetrische hydrierung |
| CN111056932A (zh) * | 2019-12-09 | 2020-04-24 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法 |
| MY208900A (en) | 2019-12-09 | 2025-06-09 | Wanhua Chemical Group Co Ltd | Preparation method for optically active citronellal |
| CN110872217A (zh) * | 2019-12-09 | 2020-03-10 | 万华化学集团股份有限公司 | 一种光学活性的香茅醛的制备方法 |
| CN111004102B (zh) * | 2019-12-23 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂 |
| CN111056933B (zh) * | 2019-12-24 | 2022-11-08 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂体系 |
| CN111269103A (zh) * | 2020-02-24 | 2020-06-12 | 万华化学集团股份有限公司 | 一种高效制备r-香茅醛的方法 |
| CN111792986B (zh) * | 2020-07-22 | 2022-09-20 | 万华化学集团股份有限公司 | 一种制备r-香茅醛的方法 |
| CN112110805B (zh) * | 2020-10-26 | 2022-07-12 | 万华化学集团股份有限公司 | 一种制备r-香茅醛的方法 |
| CN114014745B (zh) * | 2021-12-07 | 2024-06-25 | 万华化学集团营养科技有限公司 | 一种低色号l-薄荷醇的及其制备方法 |
| WO2023137133A2 (en) | 2022-01-13 | 2023-07-20 | Basf Se | Process for the selective catalytic hydrogenation of dienones |
| CN116041391A (zh) * | 2022-12-02 | 2023-05-02 | 江苏宏邦化工科技有限公司 | 一种手性双膦配体铑配合物及其制备方法和应用 |
| WO2025011972A1 (en) | 2023-07-07 | 2025-01-16 | Basf Se | Photoisomerization of geranial and neral |
| WO2025191084A1 (en) | 2024-03-15 | 2025-09-18 | Basf Se | Rhodium-carbonyl compounds for use as selective hydrogenation catalysts |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5278812A (en) | 1975-12-26 | 1977-07-02 | Nikki Chem Co Ltd | Selective production method of saturated aldehyde |
| FR2396735A1 (fr) | 1977-07-04 | 1979-02-02 | Rhone Poulenc Ind | Procede de preparation de citronellal optiquement actif |
| JPS5791743A (en) * | 1980-11-26 | 1982-06-08 | Agency Of Ind Science & Technol | Catalyst for reducing alpha, beta-unsaturated aldehyde |
| JPS5995234A (ja) * | 1982-11-24 | 1984-06-01 | Mitsubishi Chem Ind Ltd | ヒドロホルミル化方法 |
| JP3032110B2 (ja) * | 1994-03-17 | 2000-04-10 | 高砂香料工業株式会社 | 光学活性なジアミノヘキサノン誘導体の製造方法 |
| JP3528244B2 (ja) * | 1994-06-30 | 2004-05-17 | 三菱化学株式会社 | ロジウム系錯体触媒の製造方法及びその触媒を用いたヒドロホルミル化方法 |
| EP1053974A1 (en) * | 1999-05-17 | 2000-11-22 | Quest International B.V. | Reactions using lewis acids |
| DE19962907A1 (de) * | 1999-12-23 | 2001-07-05 | Basf Ag | Verfahren zur Herstellung von C¶10¶-C¶30¶-Alkenen durch partielle Hydrierung von Alkinen an Festbett-Palladium-Trägerkatalysatoren |
| JP4676617B2 (ja) | 2001-01-18 | 2011-04-27 | 高砂香料工業株式会社 | イソプレゴールの製造方法 |
-
2004
- 2004-10-11 DE DE102004049631A patent/DE102004049631A1/de not_active Withdrawn
-
2005
- 2005-10-08 AT AT05805158T patent/ATE495143T1/de active
- 2005-10-08 ES ES05805158T patent/ES2359837T3/es not_active Expired - Lifetime
- 2005-10-08 CN CN2005800346545A patent/CN101039894B/zh not_active Expired - Lifetime
- 2005-10-08 WO PCT/EP2005/010847 patent/WO2006040096A1/de not_active Ceased
- 2005-10-08 US US11/577,068 patent/US7534921B2/en active Active
- 2005-10-08 EP EP05805158A patent/EP1802561B1/de not_active Expired - Lifetime
- 2005-10-08 JP JP2007535110A patent/JP5128282B2/ja not_active Expired - Lifetime
- 2005-10-08 DE DE502005010853T patent/DE502005010853D1/de not_active Expired - Lifetime
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