DE2928347C2 - Aliphatische Ether des Hydroximethylcyclododecans, diese enthaltende Stoffkombinationen sowie ihre Verwendung zur Herstellung von Riechstoffkompositionen - Google Patents
Aliphatische Ether des Hydroximethylcyclododecans, diese enthaltende Stoffkombinationen sowie ihre Verwendung zur Herstellung von RiechstoffkompositionenInfo
- Publication number
- DE2928347C2 DE2928347C2 DE2928347A DE2928347A DE2928347C2 DE 2928347 C2 DE2928347 C2 DE 2928347C2 DE 2928347 A DE2928347 A DE 2928347A DE 2928347 A DE2928347 A DE 2928347A DE 2928347 C2 DE2928347 C2 DE 2928347C2
- Authority
- DE
- Germany
- Prior art keywords
- ether
- hydroxymethylcyclododecane
- production
- fragrance compositions
- combinations
- 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
Links
- -1 Aliphatic ethers Chemical class 0.000 title claims description 8
- 239000003205 fragrance Substances 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title claims description 7
- 239000000126 substance Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JQYWAZNRRQRPNN-UHFFFAOYSA-N cyclododecylmethanol Chemical compound OCC1CCCCCCCCCCC1 JQYWAZNRRQRPNN-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 7
- OGYDYKGQVKCZED-UHFFFAOYSA-N ethoxymethylcyclododecane Chemical compound CCOCC1CCCCCCCCCCC1 OGYDYKGQVKCZED-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 5
- ZZCPUTXODKGFBH-UHFFFAOYSA-N methoxymethylcyclododecane Chemical compound COCC1CCCCCCCCCCC1 ZZCPUTXODKGFBH-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- ZALUVOMBUNTCME-UHFFFAOYSA-N propan-2-yloxymethylcyclododecane Chemical compound CC(C)OCC1CCCCCCCCCCC1 ZALUVOMBUNTCME-UHFFFAOYSA-N 0.000 description 4
- NNQDMQVWOWCVEM-NSCUHMNNSA-N (e)-1-bromoprop-1-ene Chemical compound C\C=C\Br NNQDMQVWOWCVEM-NSCUHMNNSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- RCNFLHIGXJZJTB-UHFFFAOYSA-N cyclodecylmethanol Chemical compound OCC1CCCCCCCCC1 RCNFLHIGXJZJTB-UHFFFAOYSA-N 0.000 description 1
- XRLIZCVYAYNXIF-UHFFFAOYSA-N cyclododeca-1,3,5-triene Chemical class C1CCCC=CC=CC=CCC1 XRLIZCVYAYNXIF-UHFFFAOYSA-N 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- KPWHNLMDUZQXHL-UHFFFAOYSA-N prop-1-enoxymethylcyclododecane Chemical compound CC=COCC1CCCCCCCCCCC1 KPWHNLMDUZQXHL-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/115—Saturated ethers containing carbocyclic rings
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2928347A DE2928347C2 (de) | 1979-07-13 | 1979-07-13 | Aliphatische Ether des Hydroximethylcyclododecans, diese enthaltende Stoffkombinationen sowie ihre Verwendung zur Herstellung von Riechstoffkompositionen |
| EP80102703A EP0022460B1 (de) | 1979-07-13 | 1980-05-16 | Aliphatische Ether des Hydroximethylcyclododecans und ihre Verwendung zur Herstellung von Riechstoffkompositionen |
| US06/167,600 US4359588A (en) | 1979-07-13 | 1980-07-11 | Odoriferous aliphatic ethers of hydroxymethylcyclododecane |
| JP9410280A JPS5615228A (en) | 1979-07-13 | 1980-07-11 | Aliphatic ether of hydroxymethylcyclododecane* mixture and perfume mixture containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2928347A DE2928347C2 (de) | 1979-07-13 | 1979-07-13 | Aliphatische Ether des Hydroximethylcyclododecans, diese enthaltende Stoffkombinationen sowie ihre Verwendung zur Herstellung von Riechstoffkompositionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2928347B1 DE2928347B1 (de) | 1980-12-11 |
| DE2928347C2 true DE2928347C2 (de) | 1981-11-26 |
Family
ID=6075647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2928347A Expired DE2928347C2 (de) | 1979-07-13 | 1979-07-13 | Aliphatische Ether des Hydroximethylcyclododecans, diese enthaltende Stoffkombinationen sowie ihre Verwendung zur Herstellung von Riechstoffkompositionen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4359588A (en, 2012) |
| EP (1) | EP0022460B1 (en, 2012) |
| JP (1) | JPS5615228A (en, 2012) |
| DE (1) | DE2928347C2 (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3216084A1 (de) * | 1982-04-30 | 1983-11-03 | Chemische Werke Hüls AG, 4370 Marl | Makrocyclische dicarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als riechstoffe |
| JPS61126013A (ja) * | 1984-11-20 | 1986-06-13 | Kuraray Co Ltd | 香料組成物 |
| DE3703585A1 (de) * | 1987-02-06 | 1988-08-18 | Consortium Elektrochem Ind | Alkohole und ether mit cyclododecyl- und cyclododecenylgruppen, deren herstellung und verwendung als duftstoffe |
| DE3711157A1 (de) * | 1987-04-02 | 1988-10-20 | Haarmann & Reimer Gmbh | Methylcyclododecatri-2,5,9-en-1-ole, verfahren zu ihrer herstellung und ihre verwendung |
| JPH02125079U (en, 2012) * | 1989-03-20 | 1990-10-15 | ||
| JPH0594363U (ja) * | 1992-05-22 | 1993-12-24 | 龍太郎 澤田 | 装着式トラップ |
| US20030118761A1 (en) * | 2001-12-21 | 2003-06-26 | Kimberly-Clark Worldwide, Inc. | Elastomeric articles having improved chemical resistance |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1196810B (de) * | 1963-10-08 | 1965-07-15 | Haarmann & Reimer Gmbh | Riechstoffe |
| DE1211174B (de) * | 1963-10-17 | 1966-02-24 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Monooxierungsprodukten der cyclischen Di- und Trimeren des Butadiens-(1, 3) |
| CH533072A (de) * | 1970-11-03 | 1973-01-31 | Givaudan & Cie Sa | Verfahren zur Herstellung von neuen Riechstoffen |
-
1979
- 1979-07-13 DE DE2928347A patent/DE2928347C2/de not_active Expired
-
1980
- 1980-05-16 EP EP80102703A patent/EP0022460B1/de not_active Expired
- 1980-07-11 US US06/167,600 patent/US4359588A/en not_active Expired - Lifetime
- 1980-07-11 JP JP9410280A patent/JPS5615228A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| US4359588A (en) | 1982-11-16 |
| EP0022460A1 (de) | 1981-01-21 |
| JPS5615228A (en) | 1981-02-14 |
| DE2928347B1 (de) | 1980-12-11 |
| JPS6314691B2 (en, 2012) | 1988-04-01 |
| EP0022460B1 (de) | 1982-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8339 | Ceased/non-payment of the annual fee |