DE19645922A1 - Verfahren zur Herstellung von Rosenoxid - Google Patents
Verfahren zur Herstellung von RosenoxidInfo
- Publication number
- DE19645922A1 DE19645922A1 DE19645922A DE19645922A DE19645922A1 DE 19645922 A1 DE19645922 A1 DE 19645922A1 DE 19645922 A DE19645922 A DE 19645922A DE 19645922 A DE19645922 A DE 19645922A DE 19645922 A1 DE19645922 A1 DE 19645922A1
- Authority
- DE
- Germany
- Prior art keywords
- diol
- mixture
- solvent
- weight
- individual components
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 42
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 title claims description 39
- 229930007790 rose oxide Natural products 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 53
- 150000002009 diols Chemical class 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- HWNJNAUJFVQJRV-UHFFFAOYSA-N 3,7-dimethyloct-7-ene-1,6-diol Chemical compound OCCC(C)CCC(O)C(C)=C HWNJNAUJFVQJRV-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- CZCBTSFUTPZVKJ-NXEZZACHSA-N (2S,4R)-rose oxide Chemical compound C[C@@H]1CCO[C@H](C=C(C)C)C1 CZCBTSFUTPZVKJ-NXEZZACHSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 230000001953 sensory effect Effects 0.000 claims description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- 239000000010 aprotic solvent Substances 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 150000002430 hydrocarbons Chemical class 0.000 claims 4
- 235000011007 phosphoric acid Nutrition 0.000 claims 4
- 230000035484 reaction time Effects 0.000 claims 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- 238000004061 bleaching Methods 0.000 claims 3
- 239000008096 xylene Substances 0.000 claims 3
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 claims 2
- 150000003016 phosphoric acids Chemical class 0.000 claims 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 2
- XGXZPVHXOMQSIT-UHFFFAOYSA-N [W].O[Si](O)(O)O Chemical compound [W].O[Si](O)(O)O XGXZPVHXOMQSIT-UHFFFAOYSA-N 0.000 claims 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims 1
- 150000002432 hydroperoxides Chemical class 0.000 claims 1
- 210000002741 palatine tonsil Anatomy 0.000 claims 1
- DGUKXCVHOUQPPA-UHFFFAOYSA-N phosphoric acid tungsten Chemical compound [W].OP(O)(O)=O DGUKXCVHOUQPPA-UHFFFAOYSA-N 0.000 claims 1
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 22
- CZCBTSFUTPZVKJ-ZJUUUORDSA-N (2R,4R)-rose oxide Chemical compound C[C@@H]1CCO[C@@H](C=C(C)C)C1 CZCBTSFUTPZVKJ-ZJUUUORDSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- VXRCLLPWPPTREM-UHFFFAOYSA-N 3,7-dimethyloct-5-ene-1,7-diol Chemical compound OCCC(C)CC=CC(C)(C)O VXRCLLPWPPTREM-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 241000220317 Rosa Species 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 240000000581 Triticum monococcum Species 0.000 description 4
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 4
- 235000000484 citronellol Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QMVPMAAFGQKVCJ-JTQLQIEISA-N (-)-Citronellol Chemical compound OCC[C@@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-JTQLQIEISA-N 0.000 description 3
- 229930007775 (2S,4R)-rose oxide Natural products 0.000 description 3
- 229930004024 (S)-(-)-citronellol Natural products 0.000 description 3
- 235000018285 (S)-(-)-citronellol Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229930007781 (2R,4R)-rose oxide Natural products 0.000 description 2
- 229930007778 (2R,4S)-rose oxide Natural products 0.000 description 2
- CZCBTSFUTPZVKJ-UWVGGRQHSA-N (2R,4S)-rose oxide Chemical compound C[C@H]1CCO[C@@H](C=C(C)C)C1 CZCBTSFUTPZVKJ-UWVGGRQHSA-N 0.000 description 2
- 229930007784 (2S,4S)-rose oxide Natural products 0.000 description 2
- CZCBTSFUTPZVKJ-VHSXEESVSA-N (2S,4S)-rose oxide Chemical compound C[C@H]1CCO[C@H](C=C(C)C)C1 CZCBTSFUTPZVKJ-VHSXEESVSA-N 0.000 description 2
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Natural products CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- -1 2-methyl-prop-1-en-1-yl Chemical group 0.000 description 1
- JRIATCFPZFOVNP-UHFFFAOYSA-N 4-methylidene-2-(2-methylprop-1-enyl)oxane Chemical compound CC(C)=CC1CC(=C)CCO1 JRIATCFPZFOVNP-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000005950 photosensitized reaction Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fats And Perfumes (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19645922A DE19645922A1 (de) | 1996-11-08 | 1996-11-08 | Verfahren zur Herstellung von Rosenoxid |
| DE59706373T DE59706373D1 (de) | 1996-11-08 | 1997-10-30 | Verfahren zur Herstellung von Rosenoxid |
| EP97118891A EP0842926B1 (de) | 1996-11-08 | 1997-10-30 | Verfahren zur Herstellung von Rosenoxid |
| ES97118891T ES2170910T3 (es) | 1996-11-08 | 1997-10-30 | Procedimiento para la preparacion de oxido de rosas. |
| IL12210897A IL122108A (en) | 1996-11-08 | 1997-11-04 | Process for producing a rose oxide |
| JP9305790A JPH10168075A (ja) | 1996-11-08 | 1997-11-07 | ローゼンオキシドの製法 |
| US08/966,185 US5892059A (en) | 1996-11-08 | 1997-11-07 | Process for producing a rose oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19645922A DE19645922A1 (de) | 1996-11-08 | 1996-11-08 | Verfahren zur Herstellung von Rosenoxid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19645922A1 true DE19645922A1 (de) | 1998-05-14 |
Family
ID=7810926
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19645922A Withdrawn DE19645922A1 (de) | 1996-11-08 | 1996-11-08 | Verfahren zur Herstellung von Rosenoxid |
| DE59706373T Expired - Fee Related DE59706373D1 (de) | 1996-11-08 | 1997-10-30 | Verfahren zur Herstellung von Rosenoxid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59706373T Expired - Fee Related DE59706373D1 (de) | 1996-11-08 | 1997-10-30 | Verfahren zur Herstellung von Rosenoxid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5892059A (enExample) |
| EP (1) | EP0842926B1 (enExample) |
| JP (1) | JPH10168075A (enExample) |
| DE (2) | DE19645922A1 (enExample) |
| ES (1) | ES2170910T3 (enExample) |
| IL (1) | IL122108A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942997A1 (de) * | 1999-09-09 | 2001-03-15 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Rosenoxid über Halohydrine oder Epoxide |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003087387A1 (en) * | 2002-04-08 | 2003-10-23 | Council Of Scientific And Industrial Research | Chemo-enzymatic synthesis of optically enriched rose-oxides |
| WO2006070383A1 (en) * | 2004-12-27 | 2006-07-06 | Council Of Scientific And Industrial Research | Process for the preparation of nerol oxide |
| US7681577B2 (en) * | 2006-10-23 | 2010-03-23 | Klipsch, Llc | Ear tip |
| CN104230863A (zh) * | 2013-06-18 | 2014-12-24 | 怀化市芬芳香料有限公司 | 光学活性氧化玫瑰的制备方法 |
| CN104230862A (zh) * | 2013-06-18 | 2014-12-24 | 怀化市芬芳香料有限公司 | 高顺式玫瑰醚的制备方法 |
| GB202203697D0 (en) | 2022-03-17 | 2022-05-04 | Givaudan Sa | Process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL276939A (enExample) * | 1961-04-07 | |||
| DE1443338C3 (de) * | 1961-05-18 | 1974-02-28 | Studiengesellschaft Kohle Mbh, 4330 Muelheim | Verfahren zur Herstellung von cyclischen 6-Ring-Äthern |
| CH503723A (de) * | 1966-03-30 | 1971-02-28 | Roure Bertrand Dupont Sa | Verfahren zur Herstellung von 2-(2-Methyl-1-propenyl)-4-methyl-tetrahydropyran |
| DE3150234A1 (de) * | 1981-12-18 | 1983-06-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ueberwiegend das z-isomere enthaltendem rosenoxid |
| JP3374357B2 (ja) * | 1995-08-29 | 2003-02-04 | 高砂香料工業株式会社 | ３，７−ジメチル−５，７−オクタジエン−１−オールの製造方法 |
-
1996
- 1996-11-08 DE DE19645922A patent/DE19645922A1/de not_active Withdrawn
-
1997
- 1997-10-30 EP EP97118891A patent/EP0842926B1/de not_active Expired - Lifetime
- 1997-10-30 ES ES97118891T patent/ES2170910T3/es not_active Expired - Lifetime
- 1997-10-30 DE DE59706373T patent/DE59706373D1/de not_active Expired - Fee Related
- 1997-11-04 IL IL12210897A patent/IL122108A/xx not_active IP Right Cessation
- 1997-11-07 US US08/966,185 patent/US5892059A/en not_active Expired - Fee Related
- 1997-11-07 JP JP9305790A patent/JPH10168075A/ja not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942997A1 (de) * | 1999-09-09 | 2001-03-15 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Rosenoxid über Halohydrine oder Epoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| IL122108A (en) | 2000-08-31 |
| EP0842926A1 (de) | 1998-05-20 |
| IL122108A0 (en) | 1998-04-05 |
| EP0842926B1 (de) | 2002-02-13 |
| JPH10168075A (ja) | 1998-06-23 |
| DE59706373D1 (de) | 2002-03-21 |
| US5892059A (en) | 1999-04-06 |
| ES2170910T3 (es) | 2002-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2808817C2 (enExample) | ||
| DE19645922A1 (de) | Verfahren zur Herstellung von Rosenoxid | |
| DE602005003937T2 (de) | Alicyclische carbonsäureoxycarbonylmethylester und deren verwendung als riechstoffen | |
| DE3150234A1 (de) | Verfahren zur herstellung von ueberwiegend das z-isomere enthaltendem rosenoxid | |
| EP0164763B1 (de) | Neue substituierte Tetraline und Indane (I), Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) | |
| DE2516696C3 (de) | Riechstoffe der 3,6,6-Trimethyll-(but-3-enoyl)-cyclohexenreihe, Verfahren zu deren Herstellung und diese enthaltende Riechstoffkompositionen | |
| DE2748633B2 (de) | Tetramethyl-substituierte Acetophenone, Verfahren zu deren Herstellung und deren Verwendung als Riechstoffe | |
| EP0301375B1 (de) | Bicyclische Aldehyde | |
| EP0021100B1 (de) | Als Einzelverbindungen (I) oder in Form von Gemischen mit (IV) vorliegende Cyclohexenderivate, Verfahren zur Herstellung von (I), Verwendung von (I) bzw. (I+IV) als Riech- und/oder Geschmackstoffe und Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) bzw. (I+IV) | |
| EP0000719B1 (de) | Neue 1,4-Epoxy-trimethyl-butenyliden-cyclohexane (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe, Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an den neuen Cyclohexanen | |
| EP0115274B1 (de) | Epoxide von bicyclischen Verbindungen, Verfahren zu deren Herstellung und Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an solchen Verbindungen | |
| DE2812288A1 (de) | Caranverbindungen | |
| EP0116127B1 (de) | Aliphatische Ether des Cyclododecen-2-ols, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Riechstoffkompositionen | |
| DE19622497A1 (de) | Verfahren zur Herstellung von Tetrahydrofuran aus Dialkoxybutenen | |
| DE69021442T2 (de) | Verfahren zur Herstellung von 2, 3-Di-substituierten Cyclopentanonen. | |
| DE60209664T2 (de) | Duftstoffzusammensetzung enthaltend 3-(3-Hexenyl)-2-Cyclopentenon | |
| DE19822232A1 (de) | 2,4,6-Trimethyl-4-phenyl-1,3-dioxan | |
| JPS628109B2 (enExample) | ||
| DE2242751B2 (de) | Verfahren zur Herstellung von ungesättigten Ketonen | |
| EP0203152B1 (de) | Methylsubstituierte bicyclo ad2.2.1 bdheptan-nitrile, verfahren zur herstellung dieser nitrile und deren verwendung als riechstoffe | |
| EP0340645B1 (de) | Isomere Formyl-trimethylbicyclo(2,2,2)oct-7-ene | |
| EP3297982A1 (de) | Oxidation von limonen | |
| DE3415067A1 (de) | Verwendung von 1-phenylpenten-4-on-1 und dessen methylhomologen zur vergroesserung oder steigerung des aromas von parfumzusammensetzungen, koelnisch waessern und parfuemierten artikeln | |
| EP0115582A2 (de) | Verwendung von Cyclododecen-2-on als Riechstoff und Verfahren zu seiner Herstellung | |
| DE2461593C3 (de) | 1,2,6-Trimethyltricyclo [53,2,O2'7! -dodeca-5-on, Verfahren zu seiner Herstellung und seine Verwendung als Riechstoff |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: SYMRISE GMBH & CO. KG, 37603 HOLZMINDEN, DE |
|
| 8141 | Disposal/no request for examination |