JPS6157815B2 - - Google Patents
Info
- Publication number
- JPS6157815B2 JPS6157815B2 JP8970379A JP8970379A JPS6157815B2 JP S6157815 B2 JPS6157815 B2 JP S6157815B2 JP 8970379 A JP8970379 A JP 8970379A JP 8970379 A JP8970379 A JP 8970379A JP S6157815 B2 JPS6157815 B2 JP S6157815B2
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- reaction
- citronellal
- enamine
- diethylamine
- 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
- AFMZGMJNKXOLEM-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dien-1-amine Chemical class CC(C)=CCC\C(C)=C\CN AFMZGMJNKXOLEM-JXMROGBWSA-N 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 150000002081 enamines Chemical class 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 19
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 19
- 235000000983 citronellal Nutrition 0.000 description 12
- 229930003633 citronellal Natural products 0.000 description 12
- -1 terpene aldehydes Chemical class 0.000 description 12
- XDEJHXKVKISANH-KAMYIIQDSA-N (2z)-n,n-diethyl-3,7-dimethylocta-2,6-dien-1-amine Chemical compound CCN(CC)C\C=C(\C)CCC=C(C)C XDEJHXKVKISANH-KAMYIIQDSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010632 citronella oil Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8970379A JPS5615232A (en) | 1979-07-14 | 1979-07-14 | Production of terpene aldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8970379A JPS5615232A (en) | 1979-07-14 | 1979-07-14 | Production of terpene aldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5615232A JPS5615232A (en) | 1981-02-14 |
| JPS6157815B2 true JPS6157815B2 (fr) | 1986-12-09 |
Family
ID=13978129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8970379A Granted JPS5615232A (en) | 1979-07-14 | 1979-07-14 | Production of terpene aldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5615232A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY170265A (en) * | 2012-12-18 | 2019-07-15 | Dsm Ip Assets Bv | Polythiols as cis/trans isomerization catalysts for unsaturated compounds |
-
1979
- 1979-07-14 JP JP8970379A patent/JPS5615232A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5615232A (en) | 1981-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Holmquist et al. | A selective method for the direct conversion of aldehydes into. beta.-keto esters with ethyl diazoacetate catalyzed by tin (II) chloride | |
| McMurry et al. | A new method of olefin synthesis. Coupling of lithium dialkylcuprates with enol triflates | |
| US5973200A (en) | Process for the preparation of 2-hydroxy-4-(methylthio) butanoic acid or methionine by mercaptan addition | |
| Pitteloud et al. | On the Claisen Rearrangement of Allyl Ethyl Ketene Acetals Generated in situ via Benzeneselenenic Acid Eliminiation | |
| Ranu et al. | A convenient synthesis of β, γ-unsaturated ketones through zinc-mediated allylation of acid chlorides | |
| US2671810A (en) | Long-chain diketones | |
| JPS6157815B2 (fr) | ||
| US3579550A (en) | Oxygenated derivatives of acyclic olefins | |
| Moyer et al. | An improved synthesis of peroxybenzoic acid | |
| Ramachandran et al. | MICHAEL ADDITION OF DITHIOBENZOIC ACID TO α, β-UNSATURATED KETONES. A NEW SERIES OF DITHIOESTERS | |
| US4139557A (en) | Method of preparing dimethylacetamide in presence of MoO3 catalyst | |
| DE2222213C3 (de) | Verfahren zur Herstellung von α,β-ungesättigten Oxoverbindungen | |
| DE2518031A1 (de) | Verfahren zur herstellung von oxoverbindungen | |
| JACOBS et al. | 1, 3-Diphenyl-1, 3-butadiene Dimers1 | |
| EP0007076B1 (fr) | Dihydrobisabolènes et dihydrobisabolol, leur préparation et utilisation comme agents odoriférants | |
| DE2435981A1 (de) | Verfahren zur herstellung aethylenartiger verbindungen sowie nach diesem verfahren hergestellte verbindungen | |
| JPS585176B2 (ja) | ２− ハロゲン −１− シクロペンタデセン −１− カルボンサンエステルノ セイゾウホウ | |
| US2560921A (en) | Solvent extraction of butanolones from water | |
| DE2415931A1 (de) | Verfahren zur herstellung von ketoestern | |
| US3892814A (en) | Cyclopropane derivatives | |
| JPS6310687B2 (fr) | ||
| JPH0451533B2 (fr) | ||
| US4247718A (en) | Process for the preparation of α-β unsaturated alcohols | |
| JPH11322659A (ja) | 不飽和アルデヒドの製造方法 | |
| EP0005196A1 (fr) | Dérivés d'octylcyclohexane, leur préparation et utilisation comme composés parfumants |