DE3530885A1 - 16-oxa-bicyclo(13.1.0)-hexadec-7-en, verfahren zu dessen herstellung und dessen verwendung als riechstoff - Google Patents
16-oxa-bicyclo(13.1.0)-hexadec-7-en, verfahren zu dessen herstellung und dessen verwendung als riechstoffInfo
- Publication number
- DE3530885A1 DE3530885A1 DE19853530885 DE3530885A DE3530885A1 DE 3530885 A1 DE3530885 A1 DE 3530885A1 DE 19853530885 DE19853530885 DE 19853530885 DE 3530885 A DE3530885 A DE 3530885A DE 3530885 A1 DE3530885 A1 DE 3530885A1
- Authority
- DE
- Germany
- Prior art keywords
- hexadec
- oxa
- bicyclo
- production
- fragrant
- 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- Withdrawn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
- NCGQTXHIOQZATM-UHFFFAOYSA-N 16-oxabicyclo[13.1.0]hexadec-8-ene Chemical compound C1CCCCC=CCCCCCCC2OC21 NCGQTXHIOQZATM-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003205 fragrance Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- AQLCQUACLXRPKV-UHFFFAOYSA-N cyclopentadeca-1,8-diene Chemical compound C1CCCC=CCCCCCC=CCC1 AQLCQUACLXRPKV-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000004965 peroxy acids Chemical class 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KUZFTOAYXWRQAA-UPHRSURJSA-N (8z)-cyclopentadec-8-en-1-one Chemical compound O=C1CCCCCC\C=C/CCCCCC1 KUZFTOAYXWRQAA-UPHRSURJSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- ZRCIIOJLEHKCSZ-UHFFFAOYSA-N cyclopentadec-7-en-1-one Chemical compound O=C1CCCCCCCC=CCCCCC1 ZRCIIOJLEHKCSZ-UHFFFAOYSA-N 0.000 description 1
- WYRUMRVEQUDPIO-UHFFFAOYSA-N cyclopentadecadiene dioxide Chemical compound C1CCCCCCCCCCC2OC2C2OC21 WYRUMRVEQUDPIO-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HYERJXDYFLQTGF-UHFFFAOYSA-N rhenium Chemical compound [Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re] HYERJXDYFLQTGF-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853530885 DE3530885A1 (de) | 1985-08-29 | 1985-08-29 | 16-oxa-bicyclo(13.1.0)-hexadec-7-en, verfahren zu dessen herstellung und dessen verwendung als riechstoff |
| US06/855,350 US4766107A (en) | 1985-08-29 | 1986-04-24 | 16-Oxa-bicyclo-[13.1.0]-hexadec-7-ene and its application as a fragrance |
| JP61121366A JPS6251677A (ja) | 1985-08-29 | 1986-05-28 | １６−オキサ−ビシクロ〔１３，１，０〕−ヘキサデセン（７）、１６−オキサ−ビシクロ〔１３，１，０〕−ヘキサデセン（７）の製造方法、および１６−オキサ−ビシクロ〔１３，１，０〕−ヘキサデセン（７）を含有する香料 |
| DE8686111892T DE3661072D1 (en) | 1985-08-29 | 1986-08-28 | 16-oxa-bicycloû13.1.0¨-hexadec-7-ene, process for its production and its use as a perfume |
| EP86111892A EP0216185B1 (de) | 1985-08-29 | 1986-08-28 | 16-Oxa-bicyclo [13.1.0]-hexadec-7-en, Verfahren zu dessen Herstellung und dessen Verwendung als Riechstoff |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853530885 DE3530885A1 (de) | 1985-08-29 | 1985-08-29 | 16-oxa-bicyclo(13.1.0)-hexadec-7-en, verfahren zu dessen herstellung und dessen verwendung als riechstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3530885A1 true DE3530885A1 (de) | 1987-03-05 |
Family
ID=6279676
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853530885 Withdrawn DE3530885A1 (de) | 1985-08-29 | 1985-08-29 | 16-oxa-bicyclo(13.1.0)-hexadec-7-en, verfahren zu dessen herstellung und dessen verwendung als riechstoff |
| DE8686111892T Expired DE3661072D1 (en) | 1985-08-29 | 1986-08-28 | 16-oxa-bicycloû13.1.0¨-hexadec-7-ene, process for its production and its use as a perfume |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8686111892T Expired DE3661072D1 (en) | 1985-08-29 | 1986-08-28 | 16-oxa-bicycloû13.1.0¨-hexadec-7-ene, process for its production and its use as a perfume |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4766107A (enExample) |
| EP (1) | EP0216185B1 (enExample) |
| JP (1) | JPS6251677A (enExample) |
| DE (2) | DE3530885A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387522A (zh) * | 2000-09-04 | 2002-12-25 | 曾田香料株式会社 | 环氧化合物的制造方法和含有该化合物的香料组合物以及添加了该香料组合物的食品饮料、香水、化妆品和香烟 |
| JP2006117585A (ja) * | 2004-10-21 | 2006-05-11 | Toyotama Koryo Kk | 新規香料物質及びその利用 |
| EP3153493A1 (de) | 2015-10-08 | 2017-04-12 | Basf Se | Verfahren zur reinigung von cyclohexadec-8-en-1-on |
| EP3153494A1 (de) | 2015-10-08 | 2017-04-12 | Basf Se | Verwendung neuartiger gemische von (e/z)-cyclopentadecenon-isomeren, deren herstellung und deren verwendung als aromastoff |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1196646B (de) * | 1962-05-18 | 1965-07-15 | Basf Ag | Verfahren zur Herstellung von Cyclododecanol |
| FR1479165A (fr) * | 1965-05-11 | 1967-04-28 | Firmenich & Cie | Dérivés dodécatriéniques |
| US3845078A (en) * | 1966-05-20 | 1974-10-29 | Int Flavors & Fragrances Inc | 1,5,9-trimethylcyclododecatriene derivatives |
| DD111195A1 (enExample) * | 1974-04-23 | 1975-02-05 | ||
| US4380658A (en) * | 1980-10-09 | 1983-04-19 | International Flavors & Fragrances Inc. | Mixture of aliphatic C10 -branched olefin epoxides and use thereof in augmenting or enhancing the aroma of perfumes and/or articles |
| DE3524977A1 (de) * | 1984-11-20 | 1986-05-22 | Consortium für elektrochemische Industrie GmbH, 8000 München | Verfahren zur herstellung von cycloalkadienen |
-
1985
- 1985-08-29 DE DE19853530885 patent/DE3530885A1/de not_active Withdrawn
-
1986
- 1986-04-24 US US06/855,350 patent/US4766107A/en not_active Expired - Fee Related
- 1986-05-28 JP JP61121366A patent/JPS6251677A/ja active Granted
- 1986-08-28 EP EP86111892A patent/EP0216185B1/de not_active Expired
- 1986-08-28 DE DE8686111892T patent/DE3661072D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0211591B2 (enExample) | 1990-03-14 |
| DE3661072D1 (en) | 1988-12-08 |
| EP0216185A1 (de) | 1987-04-01 |
| EP0216185B1 (de) | 1988-11-02 |
| US4766107A (en) | 1988-08-23 |
| JPS6251677A (ja) | 1987-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |