CA2480116C - Production of dihydronepetalactone by hydrogenation of nepetalactone - Google Patents
Production of dihydronepetalactone by hydrogenation of nepetalactone Download PDFInfo
- Publication number
- CA2480116C CA2480116C CA2480116A CA2480116A CA2480116C CA 2480116 C CA2480116 C CA 2480116C CA 2480116 A CA2480116 A CA 2480116A CA 2480116 A CA2480116 A CA 2480116A CA 2480116 C CA2480116 C CA 2480116C
- Authority
- CA
- Canada
- Prior art keywords
- recited
- carbon
- dihydronepetalactone
- supported
- catalyst
- 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 - Fee Related
Links
- LSRNBGXEEKNZHN-UHFFFAOYSA-N Dihydronepetalactone Chemical compound O=C1OCC(C)C2C1C(C)CC2 LSRNBGXEEKNZHN-UHFFFAOYSA-N 0.000 title claims abstract description 55
- ZDKZHVNKFOXMND-UHFFFAOYSA-N cis-Nepetalactone Natural products O=C1OC=C(C)C2C1C(C)CC2 ZDKZHVNKFOXMND-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 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 claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 claims abstract description 41
- 239000002184 metal Substances 0.000 claims abstract description 41
- 230000008569 process Effects 0.000 claims abstract description 35
- 230000003197 catalytic effect Effects 0.000 claims abstract description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 67
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 50
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 39
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 33
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229910052763 palladium Inorganic materials 0.000 claims description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052681 coesite Inorganic materials 0.000 claims description 23
- 229910052906 cristobalite Inorganic materials 0.000 claims description 23
- 229910052682 stishovite Inorganic materials 0.000 claims description 23
- 229910052905 tridymite Inorganic materials 0.000 claims description 23
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 22
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 22
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 22
- 229910052697 platinum Inorganic materials 0.000 claims description 21
- 239000000377 silicon dioxide Substances 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 19
- 239000010948 rhodium Substances 0.000 claims description 18
- 229910052741 iridium Inorganic materials 0.000 claims description 17
- 229910052703 rhodium Inorganic materials 0.000 claims description 16
- 229910052707 ruthenium Inorganic materials 0.000 claims description 16
- 229910052702 rhenium Inorganic materials 0.000 claims description 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 14
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 14
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 12
- 235000010216 calcium carbonate Nutrition 0.000 claims description 11
- 235000012239 silicon dioxide Nutrition 0.000 claims description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910000018 strontium carbonate Inorganic materials 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- DZQBLSOLVRLASG-UHFFFAOYSA-N iridium;methane Chemical compound C.[Ir] DZQBLSOLVRLASG-UHFFFAOYSA-N 0.000 claims description 2
- YFKIWUQBRSMPMZ-UHFFFAOYSA-N methane;nickel Chemical compound C.[Ni] YFKIWUQBRSMPMZ-UHFFFAOYSA-N 0.000 claims description 2
- LEDMRZGFZIAGGB-UHFFFAOYSA-L strontium carbonate Chemical group [Sr+2].[O-]C([O-])=O LEDMRZGFZIAGGB-UHFFFAOYSA-L 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims 8
- 229910001845 yogo sapphire Inorganic materials 0.000 claims 8
- 150000002739 metals Chemical class 0.000 abstract description 9
- 239000000463 material Substances 0.000 description 18
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241001529733 Nepeta Species 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000341 volatile oil Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- -1 monoterpenoid compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- XCLVQKQEQGLNEN-UHFFFAOYSA-N methyl 2-methyl-5-propan-2-ylcyclopentane-1-carboxylate Chemical compound COC(=O)C1C(C)CCC1C(C)C XCLVQKQEQGLNEN-UHFFFAOYSA-N 0.000 description 3
- 229930003658 monoterpene Natural products 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000207923 Lamiaceae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 235000010679 Nepeta cataria Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000077 insect repellent Substances 0.000 description 2
- BDXDSAWGUGHUQP-UHFFFAOYSA-N iso-neonepetalactone Natural products CC1COC(=O)C2=C(C)CCC12 BDXDSAWGUGHUQP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BDXDSAWGUGHUQP-HTQZYQBOSA-N (4S,4aR)-4,7-dimethyl-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-1-one Chemical compound C[C@@H]1COC(=O)C2=C(C)CC[C@H]12 BDXDSAWGUGHUQP-HTQZYQBOSA-N 0.000 description 1
- LSRNBGXEEKNZHN-RBXMUDONSA-N (4r,4ar,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-RBXMUDONSA-N 0.000 description 1
- LSRNBGXEEKNZHN-MAUMQABQSA-N (4r,4ar,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-MAUMQABQSA-N 0.000 description 1
- LSRNBGXEEKNZHN-XSPKLOCKSA-N (4r,4as,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@H]1([C@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-XSPKLOCKSA-N 0.000 description 1
- LSRNBGXEEKNZHN-JBDRJPRFSA-N (4r,4as,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@H]1([C@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-JBDRJPRFSA-N 0.000 description 1
- LSRNBGXEEKNZHN-JQCXWYLXSA-N (4s,4ar,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-JQCXWYLXSA-N 0.000 description 1
- LSRNBGXEEKNZHN-KDXUFGMBSA-N (4s,4ar,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-KDXUFGMBSA-N 0.000 description 1
- LSRNBGXEEKNZHN-UYXSQOIJSA-N (4s,4as,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@H]1([C@@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-UYXSQOIJSA-N 0.000 description 1
- LSRNBGXEEKNZHN-KZVJFYERSA-N (4s,4as,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@H]1([C@@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-KZVJFYERSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QLRRUWXMMVXORS-UHFFFAOYSA-N Augustine Natural products C12=CC=3OCOC=3C=C2CN2C3CC(OC)C4OC4C31CC2 QLRRUWXMMVXORS-UHFFFAOYSA-N 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- VPXAKEICIWYNGX-UHFFFAOYSA-N Isoactinidialactone Natural products CC1C2CC=C(C)C2(O)CC1=O VPXAKEICIWYNGX-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 229910020169 SiOa Inorganic materials 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YOOGDQUSAKDEKI-UHFFFAOYSA-N dehydroiridomyrmecin Natural products C1OC(=O)C(C)C2CCC(C)=C21 YOOGDQUSAKDEKI-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36947002P | 2002-04-03 | 2002-04-03 | |
| US60/369,470 | 2002-04-03 | ||
| PCT/US2003/010072 WO2003084946A1 (en) | 2002-04-03 | 2003-04-02 | Production of dihydronepetalactone by hydrogenation of nepetalactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2480116A1 CA2480116A1 (en) | 2003-10-16 |
| CA2480116C true CA2480116C (en) | 2011-01-04 |
Family
ID=28791958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2480116A Expired - Fee Related CA2480116C (en) | 2002-04-03 | 2003-04-02 | Production of dihydronepetalactone by hydrogenation of nepetalactone |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7067677B2 (https=) |
| EP (1) | EP1490351B1 (https=) |
| JP (1) | JP2005530721A (https=) |
| CN (1) | CN1331861C (https=) |
| AT (1) | ATE364040T1 (https=) |
| AU (1) | AU2003223414A1 (https=) |
| BR (1) | BRPI0308833B1 (https=) |
| CA (1) | CA2480116C (https=) |
| DE (1) | DE60314240T2 (https=) |
| ES (1) | ES2288604T3 (https=) |
| IL (1) | IL163724A0 (https=) |
| WO (1) | WO2003084946A1 (https=) |
| ZA (1) | ZA200406756B (https=) |
Families Citing this family (25)
| 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 |
| 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 |
| 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 |
| 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 |
| US20130165506A1 (en) * | 2005-09-30 | 2013-06-27 | E I Du Pont De Nemours And Company | Puleganic acid insect repellent |
| CN101316510A (zh) * | 2005-09-30 | 2008-12-03 | 纳幕尔杜邦公司 | 蒲勒酸昆虫驱避剂 |
| CA2648270C (en) * | 2006-05-10 | 2014-07-08 | E.I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions comprising dihydronepetalactone |
| 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 |
| 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 |
| 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 |
| 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 |
| US8420736B2 (en) * | 2009-06-25 | 2013-04-16 | Kaneka Corporation | Thermoplastic resin composition and molded body thereof |
| 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 |
| CN102942545B (zh) * | 2012-12-07 | 2014-07-23 | 南京中医药大学 | 一种荆芥内酯邻溴苯甲酸酯及其制备工艺和用途 |
| CN102942544B (zh) * | 2012-12-07 | 2014-08-27 | 南京中医药大学 | 一种荆芥内酯三氟甲基苯甲酸酯及其制备工艺和用途 |
| JP6310326B2 (ja) * | 2014-05-27 | 2018-04-11 | 富士フレーバー株式会社 | δ−バレロラクトンの製造方法 |
| 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 |
| US20230192637A1 (en) * | 2020-04-15 | 2023-06-22 | Zymergen Inc. | Hydrogenation of nepetalactone |
| US12378213B1 (en) | 2024-08-13 | 2025-08-05 | William Allen Boulanger | Process for the hydrogenation of catnip oil |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978000A (en) | 1975-03-19 | 1976-08-31 | American Cyanamid Company | Catalysts based on carbon supports |
| NL7604669A (nl) | 1976-05-01 | 1977-11-03 | Stamicarbon | Werkwijze voor het bereiden van dragerkatalysa- toren. |
| JP2770357B2 (ja) * | 1988-12-19 | 1998-07-02 | 味の素株式会社 | ヌクレオシド誘導体の製造方法 |
| FR2653118B1 (fr) * | 1989-10-13 | 1993-05-14 | Inst Francais Du Petrole | Hydrogenation du citral. |
| JPH04108809A (ja) * | 1990-08-29 | 1992-04-09 | Japan Synthetic Rubber Co Ltd | 重合体の水素化方法 |
| JP3337235B2 (ja) * | 1992-03-26 | 2002-10-21 | 出光興産株式会社 | 水素吸蔵体 |
| DE19602710A1 (de) * | 1996-01-26 | 1997-07-31 | Basf Ag | Verfahren zur selektiven Hydrierung von Vinyloxiran zu 1,2-Butylenoxid an Heterogenkatalysatoren |
| JP2002069064A (ja) * | 2000-08-24 | 2002-03-08 | New Japan Chem Co Ltd | γ−ブチロラクトンの製造方法 |
| CN1174973C (zh) * | 2001-04-09 | 2004-11-10 | 南京中医药大学 | 荆芥内酯及其提取工艺和用途 |
-
2003
- 2003-04-02 EP EP03719543A patent/EP1490351B1/en not_active Expired - Lifetime
- 2003-04-02 DE DE60314240T patent/DE60314240T2/de not_active Expired - Lifetime
- 2003-04-02 WO PCT/US2003/010072 patent/WO2003084946A1/en not_active Ceased
- 2003-04-02 ES ES03719543T patent/ES2288604T3/es not_active Expired - Lifetime
- 2003-04-02 US US10/405,444 patent/US7067677B2/en not_active Expired - Lifetime
- 2003-04-02 IL IL16372403A patent/IL163724A0/xx unknown
- 2003-04-02 CN CNB038074125A patent/CN1331861C/zh not_active Expired - Fee Related
- 2003-04-02 BR BRPI0308833-2A patent/BRPI0308833B1/pt not_active IP Right Cessation
- 2003-04-02 CA CA2480116A patent/CA2480116C/en not_active Expired - Fee Related
- 2003-04-02 AU AU2003223414A patent/AU2003223414A1/en not_active Abandoned
- 2003-04-02 JP JP2003582143A patent/JP2005530721A/ja active Pending
- 2003-04-02 AT AT03719543T patent/ATE364040T1/de not_active IP Right Cessation
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2004
- 2004-08-25 ZA ZA200406756A patent/ZA200406756B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1078312A1 (en) | 2006-03-10 |
| CN1642935A (zh) | 2005-07-20 |
| ZA200406756B (en) | 2006-06-28 |
| DE60314240T2 (de) | 2008-01-31 |
| ES2288604T3 (es) | 2008-01-16 |
| EP1490351A1 (en) | 2004-12-29 |
| EP1490351B1 (en) | 2007-06-06 |
| WO2003084946A1 (en) | 2003-10-16 |
| BRPI0308833B1 (pt) | 2015-07-07 |
| US7067677B2 (en) | 2006-06-27 |
| CN1331861C (zh) | 2007-08-15 |
| IL163724A0 (en) | 2005-12-18 |
| CA2480116A1 (en) | 2003-10-16 |
| AU2003223414A1 (en) | 2003-10-20 |
| BR0308833A (pt) | 2005-01-25 |
| US20030225290A1 (en) | 2003-12-04 |
| ATE364040T1 (de) | 2007-06-15 |
| JP2005530721A (ja) | 2005-10-13 |
| DE60314240D1 (de) | 2007-07-19 |
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