ES2549864T3 - Producción de dihidronepetalactona por hidrogenación de nepetalactona - Google Patents
Producción de dihidronepetalactona por hidrogenación de nepetalactona Download PDFInfo
- Publication number
- ES2549864T3 ES2549864T3 ES07863146.2T ES07863146T ES2549864T3 ES 2549864 T3 ES2549864 T3 ES 2549864T3 ES 07863146 T ES07863146 T ES 07863146T ES 2549864 T3 ES2549864 T3 ES 2549864T3
- Authority
- ES
- Spain
- Prior art keywords
- temperatures
- temperature
- nepetalactone
- dihydronepetalactone
- trans
- 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
- LSRNBGXEEKNZHN-UHFFFAOYSA-N Dihydronepetalactone Chemical compound O=C1OCC(C)C2C1C(C)CC2 LSRNBGXEEKNZHN-UHFFFAOYSA-N 0.000 title abstract 6
- 238000005984 hydrogenation reaction Methods 0.000 title abstract 4
- ZDKZHVNKFOXMND-NBEYISGCSA-N cis-trans-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-NBEYISGCSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- ZDKZHVNKFOXMND-UHFFFAOYSA-N cis-Nepetalactone Natural products O=C1OC=C(C)C2C1C(C)CC2 ZDKZHVNKFOXMND-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- ZDKZHVNKFOXMND-VDAHYXPESA-N trans-cis-Nepetalactone Natural products O=C1OC=C(C)[C@@H]2[C@@H]1[C@H](C)CC2 ZDKZHVNKFOXMND-VDAHYXPESA-N 0.000 abstract 2
- ZDKZHVNKFOXMND-ZQARSLAVSA-N trans-cis-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-ZQARSLAVSA-N 0.000 abstract 2
- ZDKZHVNKFOXMND-FTLITQJKSA-N cis-trans-Nepetalactone Natural products O=C1OC=C(C)[C@@H]2[C@H]1[C@H](C)CC2 ZDKZHVNKFOXMND-FTLITQJKSA-N 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Un procedimiento para preparar dihidronepetalactona que comprende: (a) poner en contacto en una mezcla de reacción una cantidad inicial de trans-cis nepetalactona, descrita por la estructura de la fórmula I, y una cantidad inicial de cis-trans nepetalactona descrita por la estructura de fórmula II, **Fórmula** con hidrógeno y un primer catalizador de hidrogenación sólido a una primera temperatura o temperaturas, hasta que la cantidad en peso de trans-cis nepetalactona en la mezcla de reacción no es mayor que aproximadamente 50% de su cantidad inicial, para formar una primera mezcla de productos; y (b) poner en contacto la primera mezcla de productos con hidrógeno y un segundo catalizador de hidrogenación sólido a una segunda temperatura o temperaturas, para formar una dihidronepetalactona; en donde la etapa (a) se lleva a cabo a una temperatura o temperaturas en el intervalo de 0ºC a 100ºC, y la etapa (b) se lleva a cabo a una temperatura o temperaturas en el intervalo de 50ºC a 150ºC; y en donde la temperatura o temperaturas en la etapa (b) son mayores que la temperatura o temperaturas en la etapa (a), caracterizado porque el primer y segundo catalizadores de hidrogenación sólidos contienen platino.
Description
8
12
14
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87656806P | 2006-12-21 | 2006-12-21 | |
| US876568P | 2006-12-21 | ||
| PCT/US2007/025987 WO2008079252A1 (en) | 2006-12-21 | 2007-12-20 | Production of dihydronepetalactone by hydrogenation of nepetalactone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2549864T3 true ES2549864T3 (es) | 2015-11-02 |
Family
ID=39273109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07863146.2T Active ES2549864T3 (es) | 2006-12-21 | 2007-12-20 | Producción de dihidronepetalactona por hidrogenación de nepetalactona |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8765975B2 (es) |
| EP (1) | EP2114911B1 (es) |
| CN (1) | CN101563334B (es) |
| CA (1) | CA2673047C (es) |
| DK (1) | DK2114911T3 (es) |
| ES (1) | ES2549864T3 (es) |
| SI (1) | SI2114911T1 (es) |
| WO (1) | WO2008079252A1 (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7547793B2 (en) * | 2003-03-19 | 2009-06-16 | E.I. Du Pont De Nemours And Company | Method for making insect repellent composition |
| CA2648270C (en) * | 2006-05-10 | 2014-07-08 | E.I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions comprising dihydronepetalactone |
| BRPI0719453A2 (pt) * | 2006-12-21 | 2014-03-18 | Du Pont | Processo de preparação de óleo de erva dos gatos hidrogenado, processo de preparação de produtos formulados com um óleo de erva dos gatos hidrogenado e óleo de erva dos gatos hidrogenado |
| SI2121885T1 (sl) * | 2006-12-21 | 2017-10-30 | E.I. Du Pont De Nemours And Company | Parna destilacija mačje mete |
| WO2008079253A1 (en) | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Hydrogenation of catmint oil |
| EP2129643A2 (en) * | 2006-12-21 | 2009-12-09 | E. I. Du Pont de Nemours and Company | Hydrogenation of caryophyllene |
| US9521844B2 (en) | 2006-12-21 | 2016-12-20 | E I Du Pont De Nemours And Company | Solvent addition and removal in the hydrogenation of catmint oil |
| SI2114911T1 (sl) | 2006-12-21 | 2015-12-31 | E.I. Du Pont De Nemours And Company | Produkcija dihidronepetalaktona s hidrogeniranjem nepetalaktona |
| CA2705367C (en) * | 2007-11-26 | 2016-05-31 | E.I. Du Pont De Nemours And Company | Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves |
| JP5805099B2 (ja) | 2009-11-11 | 2015-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | イヌハッカ油の回収を向上させる方法 |
| CN104181239B (zh) * | 2013-05-23 | 2015-09-30 | 湖北航天化学技术研究所 | 硝酸酯增塑聚醚推进剂中功能助剂含量的测定方法 |
| CN105738545A (zh) * | 2014-12-12 | 2016-07-06 | 湖北航天化学技术研究所 | 叠氮聚醚推进剂中有机功能助剂含量色谱测定方法 |
| CA3084263A1 (en) | 2017-12-07 | 2019-06-13 | Zymergen Inc. | Engineered biosynthetic pathways for production of (6e)-8-hydroxygeraniol by fermentation |
| BR112020012704A8 (pt) | 2017-12-21 | 2022-03-03 | Zymergen Inc | Nepetalactol oxidorredutases, nepetalactol sintases, e micróbios capazes de produzir nepetalactona |
| WO2024186653A2 (en) * | 2023-03-03 | 2024-09-12 | Entomol Products, Llc | Methods for making dihydronepetalactone and applications therefor |
| US12378213B1 (en) | 2024-08-13 | 2025-08-05 | William Allen Boulanger | Process for the hydrogenation of catnip oil |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416881A (en) * | 1979-05-18 | 1983-11-22 | The United States Of America As Represented By The Secretary Of Agriculture | Insect repellents employing cyclohexane-carbonyl morpholine compounds |
| US4476147A (en) * | 1982-05-20 | 1984-10-09 | International Flavors & Fragrances Inc. | Flavoring of alliaceous-flavored foodstuffs |
| US4496467A (en) * | 1983-02-23 | 1985-01-29 | International Flavors & Fragrances Inc. | Insect repellent, pheremonal, animal repellent diagnostic and/or aroma augmenting or enhancing compositions and articles containing at least a major proportion of poly(epsilon caprolactone)homopolymers, and having imbedded therein one or more functional |
| US4869896A (en) * | 1984-05-30 | 1989-09-26 | Angus Chemical Company | Potentiated insect repellent composition and method |
| US6013255A (en) * | 1994-04-18 | 2000-01-11 | Gist-Brocades B.V. | Stable water-in-oil emulsions |
| US6524605B1 (en) * | 1999-08-06 | 2003-02-25 | Iowa State University Research Foundation, Inc. | Biorational repellents obtained from terpenoids for use against arthropods |
| EP1272144A4 (en) * | 2000-03-27 | 2006-04-26 | Schott Ag | NEW COSMETIC BODY CLEANING AGENT AND FOOD SUPPLEMENTS CONTAINING BIOACTIVE GLASS AND METHODS FOR THE PREPARATION AND USE THEREOF |
| US20030223878A1 (en) * | 2000-05-04 | 2003-12-04 | Keudell Leopold Von | Pump and overflow valve assembly |
| US6623694B1 (en) * | 2000-08-29 | 2003-09-23 | Bath & Body Works, Inc. | Non-foaming water fountain and composition |
| US6673756B2 (en) * | 2000-09-20 | 2004-01-06 | Symrise Gmbh & Co. Kg | Multiphase soaps |
| US6462015B1 (en) * | 2000-11-10 | 2002-10-08 | International Flavors & Fragrances Inc. | Bicyclic lactones, perfumery uses thereof, processes for preparing same and intermediates therefor |
| US6707000B2 (en) * | 2001-08-24 | 2004-03-16 | Illinois Tool Works Inc. | Consumables storage box |
| US20030079786A1 (en) * | 2001-10-30 | 2003-05-01 | Diana Michael J. | Modular fluid pressure regulator with bypass |
| CN100396674C (zh) * | 2002-01-23 | 2008-06-25 | 纳幕尔杜邦公司 | 芳香化合物 |
| US20030235601A1 (en) * | 2002-03-20 | 2003-12-25 | Hallahan David L. | Insect repellent compounds |
| US20040127553A1 (en) * | 2002-03-20 | 2004-07-01 | Hallahan David L. | Insect repellent compositions comprising dihydronepetalactone |
| EP1490351B1 (en) | 2002-04-03 | 2007-06-06 | E.I. Du Pont De Nemours And Company | Production of dihydronepetalactone by hydrogenation of nepetalactone |
| WO2003086069A2 (en) * | 2002-04-08 | 2003-10-23 | Jodi Haenke | Materials and methods for controlling wood-boring insects |
| US7820145B2 (en) * | 2003-08-04 | 2010-10-26 | Foamix Ltd. | Oleaginous pharmaceutical and cosmetic foam |
| JP2007521240A (ja) | 2003-09-18 | 2007-08-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジヒドロネペタラクトンを含んでなる昆虫忌避組成物 |
| CN1953971A (zh) * | 2003-11-26 | 2007-04-25 | 纳幕尔杜邦公司 | 二氢假荆芥内酯衍生物及其制备方法 |
| US20050137252A1 (en) * | 2003-12-22 | 2005-06-23 | Scialdone Mark A. | Production of dihydronepetalactone |
| GB0409542D0 (en) * | 2004-04-29 | 2004-06-02 | Unilever Plc | Cosmetic compositions |
| CA2584354C (en) | 2004-11-03 | 2015-02-24 | E.I. Du Pont De Nemours And Company | Insect repellent compositions comprising dihydronepetalactone, an alcohol and an ester |
| US20060148842A1 (en) * | 2004-12-29 | 2006-07-06 | Scialdone Mark A | Nepetalactams and N-substituted derivatives thereof |
| JP2008526769A (ja) * | 2004-12-29 | 2008-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジヒドロネペタラクタムおよびそのn−置換誘導体 |
| US20060201391A1 (en) * | 2005-03-09 | 2006-09-14 | Scialdone Mark A | Compositions having sustained-release insect repellency |
| CN101316510A (zh) * | 2005-09-30 | 2008-12-03 | 纳幕尔杜邦公司 | 蒲勒酸昆虫驱避剂 |
| BRPI0617592A2 (pt) * | 2005-09-30 | 2011-08-02 | Du Pont | composto, composição, método para repelir um inseto ou artrópode e processo para a preparação de um composto |
| CA2648270C (en) * | 2006-05-10 | 2014-07-08 | E.I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions comprising dihydronepetalactone |
| BRPI0719453A2 (pt) * | 2006-12-21 | 2014-03-18 | Du Pont | Processo de preparação de óleo de erva dos gatos hidrogenado, processo de preparação de produtos formulados com um óleo de erva dos gatos hidrogenado e óleo de erva dos gatos hidrogenado |
| EP2129643A2 (en) * | 2006-12-21 | 2009-12-09 | E. I. Du Pont de Nemours and Company | Hydrogenation of caryophyllene |
| SI2114911T1 (sl) | 2006-12-21 | 2015-12-31 | E.I. Du Pont De Nemours And Company | Produkcija dihidronepetalaktona s hidrogeniranjem nepetalaktona |
| SI2121885T1 (sl) * | 2006-12-21 | 2017-10-30 | E.I. Du Pont De Nemours And Company | Parna destilacija mačje mete |
| WO2008079253A1 (en) * | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Hydrogenation of catmint oil |
| DE102007026049A1 (de) * | 2007-05-31 | 2008-12-04 | Beiersdorf Ag | Repellentien gegen Wespen |
| CA2705367C (en) * | 2007-11-26 | 2016-05-31 | E.I. Du Pont De Nemours And Company | Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves |
-
2007
- 2007-12-20 SI SI200731700T patent/SI2114911T1/sl unknown
- 2007-12-20 EP EP07863146.2A patent/EP2114911B1/en not_active Not-in-force
- 2007-12-20 US US12/519,770 patent/US8765975B2/en active Active
- 2007-12-20 ES ES07863146.2T patent/ES2549864T3/es active Active
- 2007-12-20 WO PCT/US2007/025987 patent/WO2008079252A1/en not_active Ceased
- 2007-12-20 CN CN2007800472373A patent/CN101563334B/zh not_active Expired - Fee Related
- 2007-12-20 CA CA2673047A patent/CA2673047C/en not_active Expired - Fee Related
- 2007-12-20 DK DK07863146.2T patent/DK2114911T3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101563334A (zh) | 2009-10-21 |
| EP2114911A1 (en) | 2009-11-11 |
| EP2114911B1 (en) | 2015-09-02 |
| US8765975B2 (en) | 2014-07-01 |
| US20100168447A1 (en) | 2010-07-01 |
| CA2673047C (en) | 2014-08-19 |
| WO2008079252A1 (en) | 2008-07-03 |
| SI2114911T1 (sl) | 2015-12-31 |
| CA2673047A1 (en) | 2008-07-03 |
| CN101563334B (zh) | 2012-08-22 |
| DK2114911T3 (en) | 2015-12-14 |
| HK1136295A1 (en) | 2010-06-25 |
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