DE2604397A1 - Polycycloalkylalkane und -alkene, sowie deren herstellung und deren verwendung als aromastoffe - Google Patents
Polycycloalkylalkane und -alkene, sowie deren herstellung und deren verwendung als aromastoffeInfo
- Publication number
- DE2604397A1 DE2604397A1 DE19762604397 DE2604397A DE2604397A1 DE 2604397 A1 DE2604397 A1 DE 2604397A1 DE 19762604397 DE19762604397 DE 19762604397 DE 2604397 A DE2604397 A DE 2604397A DE 2604397 A1 DE2604397 A1 DE 2604397A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- formula
- reaction
- carbon
- hept
- 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
- 238000004519 manufacturing process Methods 0.000 title description 11
- 239000000126 substance Substances 0.000 title description 11
- 150000001336 alkenes Chemical class 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 219
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 77
- 239000002304 perfume Substances 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 58
- 150000002430 hydrocarbons Chemical class 0.000 claims description 53
- 229930195733 hydrocarbon Natural products 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 32
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 23
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 22
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 14
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 12
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 150000004965 peroxy acids Chemical class 0.000 claims description 10
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 8
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 claims description 6
- 238000004508 fractional distillation Methods 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 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 claims description 2
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- 150000001722 carbon compounds Chemical class 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000004808 allyl alcohols Chemical group 0.000 claims 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 112
- 239000000203 mixture Substances 0.000 description 108
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 33
- 240000000513 Santalum album Species 0.000 description 32
- 235000008632 Santalum album Nutrition 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000003205 fragrance Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 25
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- 238000001704 evaporation Methods 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 19
- 238000001030 gas--liquid chromatography Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000010671 sandalwood oil Substances 0.000 description 15
- 229930013258 santalene Natural products 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- PGBNIHXXFQBCPU-ZNMIVQPWSA-N (-)-beta-santalene Natural products C1C[C@@H]2C(=C)[C@@](CCC=C(C)C)(C)[C@H]1C2 PGBNIHXXFQBCPU-ZNMIVQPWSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000000344 soap Substances 0.000 description 11
- FTAWJNHMGAAZDD-UHFFFAOYSA-N beta-Santalen Natural products CC=C(/C)CCC1(C)C2CC3C(C2)C13C FTAWJNHMGAAZDD-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000002537 cosmetic Substances 0.000 description 9
- 239000012259 ether extract Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- RTJBLRZRSVEQRH-UHFFFAOYSA-N pent-1-en-2-ol Chemical compound CCCC(O)=C RTJBLRZRSVEQRH-UHFFFAOYSA-N 0.000 description 9
- 238000007539 photo-oxidation reaction Methods 0.000 description 9
- 239000000080 wetting agent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 235000009508 confectionery Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 7
- 235000011194 food seasoning agent Nutrition 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 230000008707 rearrangement Effects 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
- 241000218657 Picea Species 0.000 description 5
- XWQLUVQFUZQPDY-UHFFFAOYSA-N Sesquifenchene Natural products CC(=CCCC1(C)C2CCC1C(=C)C2)C XWQLUVQFUZQPDY-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000005297 pyrex Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 235000019568 aromas Nutrition 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000005592 polycycloalkyl group Polymers 0.000 description 4
- 150000000116 santalene derivatives Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GJYMQFMQRRNLCY-ONEGZZNKSA-N (e)-pent-3-en-2-ol Chemical compound C\C=C\C(C)O GJYMQFMQRRNLCY-ONEGZZNKSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000144725 Amygdalus communis Species 0.000 description 3
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 3
- 239000005770 Eugenol Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 3
- 241000220317 Rosa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000020224 almond Nutrition 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 3
- 229960002217 eugenol Drugs 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- KWFJIXPIFLVMPM-UHFFFAOYSA-N α-santalene Chemical compound C1C2C3(C)C2CC1C3(C)CCC=C(C)C KWFJIXPIFLVMPM-UHFFFAOYSA-N 0.000 description 3
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- SQXVFJBNABHFQG-UHFFFAOYSA-N bicyclo[7.2.0]undecane Chemical compound C1CCCCCCC2CCC21 SQXVFJBNABHFQG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- DJYWGTBEZVORGE-CVWWDKSYSA-N cedr-8(15)-en-9-ol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(=C)C(O)C2 DJYWGTBEZVORGE-CVWWDKSYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- WDPIZEKLJKBSOZ-UHFFFAOYSA-M green s Chemical compound [Na+].C1=CC(N(C)C)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1O)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](C)C)C=C1 WDPIZEKLJKBSOZ-UHFFFAOYSA-M 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- YSZJHIGBFXADDH-UHFFFAOYSA-N heptane;propan-1-ol Chemical compound CCCO.CCCCCCC YSZJHIGBFXADDH-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- ORQWTLCYLDRDHK-UHFFFAOYSA-N phenylselanylbenzene Chemical compound C=1C=CC=CC=1[Se]C1=CC=CC=C1 ORQWTLCYLDRDHK-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
-
- 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
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
- Y10S204/903—Inorganic chemical treating agent
- Y10S204/904—Metal treating agent
-
- 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
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
- Y10S204/912—Oxygen treating agent
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)
- Epoxy Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/551,030 US4000050A (en) | 1975-02-19 | 1975-02-19 | Photochemical preparation of polycycloalkyl oxyalkanes and oxyalkenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2604397A1 true DE2604397A1 (de) | 1976-09-09 |
Family
ID=24199550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762604397 Pending DE2604397A1 (de) | 1975-02-19 | 1976-02-05 | Polycycloalkylalkane und -alkene, sowie deren herstellung und deren verwendung als aromastoffe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4000050A (enExample) |
| JP (1) | JPS51108051A (enExample) |
| DE (1) | DE2604397A1 (enExample) |
| FR (1) | FR2301228A1 (enExample) |
| GB (1) | GB1544831A (enExample) |
| NL (1) | NL7601629A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076853A (en) * | 1977-02-04 | 1978-02-28 | International Flavors & Fragrances Inc. | Flavoring with substituted norbornane derivatives |
| US4209649A (en) * | 1977-02-04 | 1980-06-24 | International Flavors & Fragrances Inc. | Novel oxyhydrocarbylnorbornane derivatives and perfumery uses thereof |
| US4229599A (en) * | 1978-09-29 | 1980-10-21 | International Flavors & Fragrances Inc. | Preparation of a caryophyllene alcohol mixture |
| US4280515A (en) * | 1978-09-29 | 1981-07-28 | International Flavors & Fragrances Inc. | Use of a mixture of isomers of caryophyllene alcohol or dihydro caryophyllene alcohol in augmenting or enhancing the aroma or taste of smoking tobacco, smoking tobacco articles and/or smoking tobacco flavors |
| US4247409A (en) * | 1979-12-21 | 1981-01-27 | International Flavors & Fragrances Inc. | Use of mixture containing caryophyllene alcohols in augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent |
| US4737224A (en) * | 1980-06-27 | 1988-04-12 | Minnesota Mining And Manufacturing Company | Process of dry adhesive-free thermal transfer of indicia |
| JPS5939823A (ja) * | 1982-08-31 | 1984-03-05 | Nippon Petrochem Co Ltd | 新規な香料組成物 |
| ES2709926T3 (es) * | 2014-12-02 | 2019-04-22 | Firmenich & Cie | Intermedios y procedimiento para la preparación de bloques de construcción de aceite de sándalo |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235306B (de) * | 1965-11-13 | 1967-03-02 | Gerberding & Co G M B H | Verfahren zur Herstellung von Terpinen-1-ol-(4) |
| US3433839A (en) * | 1966-05-12 | 1969-03-18 | Takasago Perfumery Co Ltd | Process for the production of a mixture of alicyclic hydroxyaldehydes |
| US3616372A (en) * | 1968-03-22 | 1971-10-26 | Procter & Gamble | Photochemical synthesis of cis-and transocimene |
| CH498824A (fr) * | 1968-07-29 | 1970-11-15 | Firmenich & Cie | Procédé pour la préparation d'un composé carbonylé |
-
1975
- 1975-02-19 US US05/551,030 patent/US4000050A/en not_active Expired - Lifetime
-
1976
- 1976-02-05 DE DE19762604397 patent/DE2604397A1/de active Pending
- 1976-02-09 JP JP51013105A patent/JPS51108051A/ja active Pending
- 1976-02-18 NL NL7601629A patent/NL7601629A/xx unknown
- 1976-02-19 FR FR7604578A patent/FR2301228A1/fr not_active Withdrawn
- 1976-02-19 GB GB6524/76A patent/GB1544831A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1544831A (en) | 1979-04-25 |
| NL7601629A (nl) | 1976-08-23 |
| FR2301228A1 (fr) | 1976-09-17 |
| JPS51108051A (enExample) | 1976-09-25 |
| US4000050A (en) | 1976-12-28 |
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