DE60112837T2 - Verfahren zur Herstellung von 1-Menthol - Google Patents
Verfahren zur Herstellung von 1-Menthol Download PDFInfo
- Publication number
- DE60112837T2 DE60112837T2 DE60112837T DE60112837T DE60112837T2 DE 60112837 T2 DE60112837 T2 DE 60112837T2 DE 60112837 T DE60112837 T DE 60112837T DE 60112837 T DE60112837 T DE 60112837T DE 60112837 T2 DE60112837 T2 DE 60112837T2
- Authority
- DE
- Germany
- Prior art keywords
- menthol
- hydrogenation
- pulegol
- pulegone
- transition metal
- 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.)
- Expired - Lifetime
Links
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 abstract 2
- JGVWYJDASSSGEK-UHFFFAOYSA-N 5-methyl-2-propan-2-ylidenecyclohexan-1-ol Chemical compound CC1CCC(=C(C)C)C(O)C1 JGVWYJDASSSGEK-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- NZGWDASTMWDZIW-UHFFFAOYSA-N Pulegone Natural products CC1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-UHFFFAOYSA-N 0.000 abstract 2
- USMNOWBWPHYOEA-UHFFFAOYSA-N alpha-thujone Natural products CC1C(=O)CC2(C(C)C)C1C2 USMNOWBWPHYOEA-UHFFFAOYSA-N 0.000 abstract 2
- 229930007459 p-menth-8-en-3-one Natural products 0.000 abstract 2
- HKZQJZIFODOLFR-UHFFFAOYSA-N piperitenone Chemical compound CC(C)=C1CCC(C)=CC1=O HKZQJZIFODOLFR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052723 transition metal Inorganic materials 0.000 abstract 2
- 150000003624 transition metals Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- SEZLYIWMVRUIKT-UHFFFAOYSA-N isopiperitenone Natural products CC(=C)C1CCC(C)=CC1=O SEZLYIWMVRUIKT-UHFFFAOYSA-N 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000137388 | 2000-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60112837D1 DE60112837D1 (de) | 2005-09-29 |
| DE60112837T2 true DE60112837T2 (de) | 2006-06-14 |
Family
ID=18645173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60112837T Expired - Lifetime DE60112837T2 (de) | 2000-05-10 | 2001-05-09 | Verfahren zur Herstellung von 1-Menthol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6342644B1 (enExample) |
| EP (1) | EP1153908B1 (enExample) |
| AT (1) | ATE302744T1 (enExample) |
| DE (1) | DE60112837T2 (enExample) |
| ES (1) | ES2247033T3 (enExample) |
| IN (1) | IN191940B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1546349A1 (en) * | 2002-08-02 | 2005-06-29 | Aromagen Corporation | Methods for making (-) -menthol and oxygenated menthane compounds |
| US7094725B2 (en) | 2003-07-11 | 2006-08-22 | The Hong Kong Polytechnic University | Biphenyldiphosphine compounds |
| DE102004057277A1 (de) * | 2004-11-26 | 2006-06-01 | Basf Ag | Verfahren zur Herstellung von Menthol |
| US8575086B2 (en) * | 2005-01-18 | 2013-11-05 | Takasago International Corporation | Flavor and fragrance compositions |
| JP4644881B2 (ja) * | 2008-09-19 | 2011-03-09 | 高砂香料工業株式会社 | ルテニウム錯体の製造方法 |
| US8785698B2 (en) | 2009-02-17 | 2014-07-22 | Nagaoka & Co., Ltd. | Methods and apparatus for production of natural L-menthol |
| CN102010297B (zh) * | 2010-11-23 | 2013-06-12 | 广东省食品工业研究所 | 一种手性合成左旋薄荷醇的方法 |
| 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 |
| CN102702205B (zh) * | 2012-05-16 | 2014-01-15 | 苏州新凯生物医药技术有限公司 | 西他列汀的制备方法 |
| US20150329452A1 (en) | 2012-11-15 | 2015-11-19 | Takasago International Corporation | Method for producing optically active isopulegol and optically active menthol |
| CN104909992A (zh) * | 2015-06-03 | 2015-09-16 | 黄山天香科技股份有限公司 | 一种用2s-反-5-甲基-2-(1-甲基乙基)环己酮制备(1r,2s,5r)-2-异丙基-5-甲基环己醇的方法 |
| CN106148431A (zh) * | 2016-09-04 | 2016-11-23 | 安徽爱有澄生物科技有限公司 | 长叶薄荷酮衍生物的制备方法 |
| US10492522B2 (en) | 2017-05-03 | 2019-12-03 | R.J. Reynolds Tobacco Company | Flavored menthol-containing objects for application to smoking article components |
| JP7337797B2 (ja) | 2017-11-16 | 2023-09-04 | シンジェンタ パーティシペーションズ アーゲー | 鏡像異性的に及びジアステレオマー的に富化したシクロブタンアミン及びアミドの調製方法 |
| CN108083980B (zh) * | 2017-11-27 | 2021-02-02 | 万华化学集团股份有限公司 | 一种制备光学纯l-薄荷醇的方法 |
| EP4168420B1 (en) * | 2020-06-19 | 2024-11-13 | DSM IP Assets B.V. | Improved process to produce specific alfa, beta-unsaturated carboxylates |
| WO2023137133A2 (en) * | 2022-01-13 | 2023-07-20 | Basf Se | Process for the selective catalytic hydrogenation of dienones |
| TW202513532A (zh) | 2023-09-15 | 2025-04-01 | 瑞士商先正達農作物保護股份公司 | 用於製備鏡像異構物富集的脂肪族胺之方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870761A (en) * | 1971-07-23 | 1975-03-11 | Basf Ag | Manufacture of piperitenone |
-
2001
- 2001-05-07 US US09/849,306 patent/US6342644B1/en not_active Expired - Fee Related
- 2001-05-09 ES ES01401180T patent/ES2247033T3/es not_active Expired - Lifetime
- 2001-05-09 IN IN378MA2001 patent/IN191940B/en unknown
- 2001-05-09 AT AT01401180T patent/ATE302744T1/de not_active IP Right Cessation
- 2001-05-09 DE DE60112837T patent/DE60112837T2/de not_active Expired - Lifetime
- 2001-05-09 EP EP01401180A patent/EP1153908B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1153908B1 (en) | 2005-08-24 |
| ATE302744T1 (de) | 2005-09-15 |
| IN191940B (enExample) | 2004-01-17 |
| DE60112837D1 (de) | 2005-09-29 |
| US20020007094A1 (en) | 2002-01-17 |
| EP1153908A2 (en) | 2001-11-14 |
| EP1153908A3 (en) | 2003-10-01 |
| ES2247033T3 (es) | 2006-03-01 |
| US6342644B1 (en) | 2002-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |