DE2064269A1 - 2 (4 Methylcyclohex 3 en 1 yl)allylh thmm und Verfahren zu seiner Herstellung - Google Patents
2 (4 Methylcyclohex 3 en 1 yl)allylh thmm und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2064269A1 DE2064269A1 DE19702064269 DE2064269A DE2064269A1 DE 2064269 A1 DE2064269 A1 DE 2064269A1 DE 19702064269 DE19702064269 DE 19702064269 DE 2064269 A DE2064269 A DE 2064269A DE 2064269 A1 DE2064269 A1 DE 2064269A1
- Authority
- DE
- Germany
- Prior art keywords
- limonene
- solution
- metalated
- ether
- reaction
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 5
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 158
- 229940087305 limonene Drugs 0.000 claims description 78
- 235000001510 limonene Nutrition 0.000 claims description 73
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- 150000002900 organolithium compounds Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000001412 amines Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000047 product Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 239000004571 lime Substances 0.000 description 17
- 244000089742 Citrus aurantifolia Species 0.000 description 16
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 16
- 235000011941 Tilia x europaea Nutrition 0.000 description 16
- 238000006263 metalation reaction Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000341 volatile oil Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- 239000002304 perfume Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000001979 organolithium group Chemical group 0.000 description 9
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- HBVOEGGRCJCMLG-DTHCKZEYSA-N (2e)-2-methyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]hepta-2,6-dien-1-ol Chemical compound OCC(/C)=C/CCC(=C)[C@H]1CCC(C)=CC1 HBVOEGGRCJCMLG-DTHCKZEYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UIMAEYMKYMNCGW-UHFFFAOYSA-N (R)-p-Mentha-1,8-dien-10-ol Chemical compound CC1=CCC(C(=C)CO)CC1 UIMAEYMKYMNCGW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000003763 carbonization Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XZRVRYFILCSYSP-OAHLLOKOSA-N (-)-beta-bisabolene Chemical compound CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1 XZRVRYFILCSYSP-OAHLLOKOSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930008564 C01BA04 - Sparteine Natural products 0.000 description 3
- 235000019499 Citrus oil Nutrition 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000218657 Picea Species 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- SLRCCWJSBJZJBV-UHFFFAOYSA-N alpha-isosparteine Natural products C1N2CCCCC2C2CN3CCCCC3C1C2 SLRCCWJSBJZJBV-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- -1 carbomethoxy-p-mentha-1,8 (10) -diene Chemical compound 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000010500 citrus oil Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 description 3
- 229960001945 sparteine Drugs 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 240000000513 Santalum album Species 0.000 description 2
- 235000008632 Santalum album Nutrition 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- XZRVRYFILCSYSP-UHFFFAOYSA-N beta-Bisabolene Natural products CC(C)=CCCC(=C)C1CCC(C)=CC1 XZRVRYFILCSYSP-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
- 239000010649 ginger oil Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 1
- SWDGKAOKYFIAHW-UHFFFAOYSA-N 1-iodo-3-methylbut-2-ene Chemical compound CC(C)=CCI SWDGKAOKYFIAHW-UHFFFAOYSA-N 0.000 description 1
- QCTTUMDTBDJCMQ-UHFFFAOYSA-N 3-(4-methylcyclohex-3-en-1-yl)but-3-enoic acid Chemical compound CC1=CCC(C(=C)CC(O)=O)CC1 QCTTUMDTBDJCMQ-UHFFFAOYSA-N 0.000 description 1
- 241000191291 Abies alba Species 0.000 description 1
- 235000004507 Abies alba Nutrition 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 240000005209 Canarium indicum Species 0.000 description 1
- 240000000467 Carum carvi Species 0.000 description 1
- 235000005747 Carum carvi Nutrition 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 244000183685 Citrus aurantium Species 0.000 description 1
- 235000007716 Citrus aurantium Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- 101000666234 Homo sapiens Thyroid adenoma-associated protein Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 240000007232 Illicium verum Species 0.000 description 1
- 235000008227 Illicium verum Nutrition 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000014435 Mentha Nutrition 0.000 description 1
- 241001072983 Mentha Species 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 241001236652 Orthodon Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 102100038148 Thyroid adenoma-associated protein Human genes 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- YHBUQBJHSRGZNF-HNNXBMFYSA-N alpha-bisabolene Natural products CC(C)=CCC=C(C)[C@@H]1CCC(C)=CC1 YHBUQBJHSRGZNF-HNNXBMFYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 229930003493 bisabolene Natural products 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004862 elemi Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 150000002627 limonene derivatives Chemical class 0.000 description 1
- 125000000396 limonene group Chemical group 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/929—Special chemical considerations
- Y10S585/947—Terpene manufacture or recovery
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88889369A | 1969-12-29 | 1969-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2064269A1 true DE2064269A1 (de) | 1971-09-02 |
Family
ID=25394119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702064269 Pending DE2064269A1 (de) | 1969-12-29 | 1970-12-29 | 2 (4 Methylcyclohex 3 en 1 yl)allylh thmm und Verfahren zu seiner Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3658925A (enrdf_load_stackoverflow) |
| CH (1) | CH557383A (enrdf_load_stackoverflow) |
| DE (1) | DE2064269A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2072098B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1297569A (enrdf_load_stackoverflow) |
| NL (1) | NL7018856A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971827A (en) * | 1974-09-09 | 1976-07-27 | G. D. Searle & Co. | Manufacture of poly-(cis)-isoprenols |
| ATE155164T1 (de) * | 1991-08-21 | 1997-07-15 | Procter & Gamble | Lipase und terpen enthaltende waschmittelzusammensetzungen |
| US20060270863A1 (en) * | 2005-05-27 | 2006-11-30 | Amyris Biotechnologies | Conversion of amorpha-4,11-diene to artemisinin and artemisinin precursors |
-
1969
- 1969-12-29 US US888893A patent/US3658925A/en not_active Expired - Lifetime
-
1970
- 1970-12-23 GB GB1297569D patent/GB1297569A/en not_active Expired
- 1970-12-28 NL NL7018856A patent/NL7018856A/xx unknown
- 1970-12-28 FR FR707046916A patent/FR2072098B1/fr not_active Expired
- 1970-12-29 CH CH1929770A patent/CH557383A/xx not_active IP Right Cessation
- 1970-12-29 DE DE19702064269 patent/DE2064269A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2072098B1 (enrdf_load_stackoverflow) | 1973-02-02 |
| GB1297569A (enrdf_load_stackoverflow) | 1972-11-22 |
| CH557383A (de) | 1974-12-31 |
| NL7018856A (enrdf_load_stackoverflow) | 1971-07-01 |
| US3658925A (en) | 1972-04-25 |
| FR2072098A1 (enrdf_load_stackoverflow) | 1971-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2455061A1 (de) | Verfahren zur herstellung von phosphoranen | |
| DE2155671C3 (de) | Neue Riechstoffe | |
| DE2163868A1 (de) | Verfahren zur Herstellung gamma, deltaungesättigter Carbonylderivate | |
| EP0045453B1 (de) | Neue Alkenole (I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) | |
| DE2064269A1 (de) | 2 (4 Methylcyclohex 3 en 1 yl)allylh thmm und Verfahren zu seiner Herstellung | |
| DE2748633B2 (de) | Tetramethyl-substituierte Acetophenone, Verfahren zu deren Herstellung und deren Verwendung als Riechstoffe | |
| DE2141309C3 (enrdf_load_stackoverflow) | ||
| DE2508060A1 (de) | Cycloaliphatische ungesaettigte ketone als geschmack- und riechstoffe | |
| DE2154215C3 (de) | In 3-Stellung substituierte 2-Alkylcyclopentanone, Verfahren zu ihrer Herstellung und ihre Verwendung als Riechstoffe | |
| DE1948536A1 (de) | Parfuemkomposition mit einem Gehalt an einem Isolongifolenester sowie Verfahren zur Herstellung von Isolongifolenestern | |
| DE2330648A1 (de) | Bizyklische verbindungen und verfahren zu deren herstellung und verwendung | |
| DE2604397A1 (de) | Polycycloalkylalkane und -alkene, sowie deren herstellung und deren verwendung als aromastoffe | |
| DE2537417C3 (de) | Verfahren zur Herstellung von tricyclischen Sesquiterpenen und diese enthaltende Parfümkompositionen | |
| DE2635545B2 (de) | 3,7-Dimethyl-3-hydroxy-octannitril, seine Herstellung und Verwendung als Duftstoff | |
| DE2242751A1 (de) | Verfahren zur herstellung von ungesaettigten ketonen und alkoholen | |
| DE2622611C2 (de) | Riechstoffgemische, Verfahren zu deren Herstellung und ihre Verwendung als Riechstoffe | |
| DE2917450A1 (de) | Neue alicyclische ketone, ihre verwendung und verfahren zu ihrer herstellung | |
| DE2461605A1 (de) | 5-acetyl-1,2,6-trimethyltricyclo eckige klammer auf 5,3,2,0 hoch 2,7 eckige klammer zu dodeca-5-en, verfahren zu seiner herstellung und seine verwendung als riechstoff | |
| DE905189C (de) | Verfahren zur Herstellung von Produkten mit Irongeruch | |
| DE69604752T2 (de) | Alkyl-substituierte C1-C3-Alkoxycyclohexan- oder -benzolverbindungen, ihre organoleptische Verwendung, und ein Verfahren zu ihrer Herstellung | |
| DE2749511C2 (de) | 2,6,9,10- und 2,6,7,10-Tetramethyl-1-oxa-spiro-[4,5]-deca-3,6-dien, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1941493C (enrdf_load_stackoverflow) | ||
| DE2821011A1 (de) | Diol -bis (allylaether), und deren verwendung als riechstoff oder riechstoffkomponente | |
| DE1037622B (de) | Neue Indanderivate als Geruch- und Aromastoffe | |
| DE3046068A1 (de) | Terpenderivate, deren herstellung, verwendung als riechstoffe sowie diese enthaltende riechstoffkompositionen |