DE2411530C2 - (3-Methyl-2-butenyl)-(3-methyl-1,3-butadienyl)-äther, Verfahren zu seiner Herstellung und seine Verwendung - Google Patents
(3-Methyl-2-butenyl)-(3-methyl-1,3-butadienyl)-äther, Verfahren zu seiner Herstellung und seine VerwendungInfo
- Publication number
- DE2411530C2 DE2411530C2 DE2411530A DE2411530A DE2411530C2 DE 2411530 C2 DE2411530 C2 DE 2411530C2 DE 2411530 A DE2411530 A DE 2411530A DE 2411530 A DE2411530 A DE 2411530A DE 2411530 C2 DE2411530 C2 DE 2411530C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- ether
- butadienyl
- formula
- compound
- 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
- 238000000034 method Methods 0.000 title claims description 8
- FMTWOCDQSALHMT-UHFFFAOYSA-N 3-methyl-1-(3-methylbuta-1,3-dienoxy)but-2-ene Chemical compound CC(C)=CCOC=CC(C)=C FMTWOCDQSALHMT-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- CKVZUYJYEQLLRP-UHFFFAOYSA-N 1-buta-1,3-dienoxybuta-1,3-diene Chemical compound C=CC=COC=CC=C CKVZUYJYEQLLRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 17
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 13
- 229940043350 citral Drugs 0.000 description 13
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical group CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 7
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- -1 acetic Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CEQACJSYZXQWRM-UHFFFAOYSA-N 1-methoxy-3-methylbuta-1,3-diene Chemical compound COC=CC(C)=C CEQACJSYZXQWRM-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- UUOKRLFKMZDLGY-UHFFFAOYSA-N 1-methoxy-3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CC(OC)OCC=C(C)C UUOKRLFKMZDLGY-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- NEJDKFPXHQRVMV-UHFFFAOYSA-N 2-methylbut-2-en-1-ol Chemical compound CC=C(C)CO NEJDKFPXHQRVMV-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- PJDVDOYSDZKWPD-UHFFFAOYSA-N 3,3-dimethyl-2-prop-1-en-2-ylpent-4-enal Chemical compound CC(=C)C(C=O)C(C)(C)C=C PJDVDOYSDZKWPD-UHFFFAOYSA-N 0.000 description 1
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- JWJJUDYXYADIGI-UHFFFAOYSA-N CC(C)C=CC(C(C)=C)=COC=C(C=CC(C)C)C(C)=C Chemical compound CC(C)C=CC(C(C)=C)=COC=C(C=CC(C)C)C(C)=C JWJJUDYXYADIGI-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940097789 heavy mineral oil Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 230000000737 periodic effect Effects 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
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- UJRAXLUXHBUNDO-UHFFFAOYSA-M sodium;hydron;oxalate Chemical compound [Na+].OC(=O)C([O-])=O UJRAXLUXHBUNDO-UHFFFAOYSA-M 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34049673A | 1973-03-12 | 1973-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2411530A1 DE2411530A1 (de) | 1974-09-26 |
| DE2411530C2 true DE2411530C2 (de) | 1982-02-18 |
Family
ID=23333605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2411530A Expired DE2411530C2 (de) | 1973-03-12 | 1974-03-11 | (3-Methyl-2-butenyl)-(3-methyl-1,3-butadienyl)-äther, Verfahren zu seiner Herstellung und seine Verwendung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS549164B2 (enrdf_load_stackoverflow) |
| AT (1) | AT342016B (enrdf_load_stackoverflow) |
| BE (1) | BE812104A (enrdf_load_stackoverflow) |
| CH (6) | CH597123A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2411530C2 (enrdf_load_stackoverflow) |
| FR (4) | FR2235904B1 (enrdf_load_stackoverflow) |
| GB (4) | GB1407945A (enrdf_load_stackoverflow) |
| IT (1) | IT1007421B (enrdf_load_stackoverflow) |
| NL (1) | NL7403290A (enrdf_load_stackoverflow) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5843374B2 (ja) * | 1973-09-07 | 1983-09-27 | 株式会社クラレ | フホウワアルデヒドカゴウブツノ セイゾウホウ |
| JPS5175014A (en) * | 1974-12-21 | 1976-06-29 | Teijin Ltd | Fuhowaarudehidono seizoho |
| NL190579C (nl) * | 1976-06-04 | 1994-05-02 | Basf Ag | Werkwijze ter bereiding van acetalen. |
| FR2390111B1 (fr) * | 1977-01-21 | 1988-02-19 | Polak Frutal Works | Procede pour la fixation d'aldehydes aromatisants en vue de leur application dans le domaine alimentaire |
| FR2453609B1 (fr) * | 1978-08-02 | 1988-04-01 | Polak Frutal Works | Procede pour la fixation d'aldehydes aromatisants en vue de leur application dans le domaine alimentaire |
| DE2926562A1 (de) * | 1979-06-30 | 1981-01-22 | Basf Ag | Verfahren zur herstellung von citral |
| JPS62178539A (ja) * | 1986-01-31 | 1987-08-05 | Kuraray Co Ltd | α，β−不飽和ケトン誘導体及びそれを含有する香料組成物 |
| FR2631337B1 (fr) * | 1988-05-16 | 1990-07-27 | Rhone Poulenc Sante | Procede de preparation du citral |
| FR2661408B1 (fr) * | 1990-04-27 | 1993-09-17 | Rhone Poulenc Nutrition Animal | Procede de preparation de citral. |
| DE19846056A1 (de) * | 1998-10-07 | 2000-04-13 | Basf Ag | Verfahren zur Herstellung von Citral |
| US6278016B1 (en) | 1999-12-09 | 2001-08-21 | Loyola University Of Chicago | Methods for conversion of isoprene to prenyl alcohol and related compounds |
| CN102149664B (zh) * | 2008-09-12 | 2014-04-23 | 弗门尼舍有限公司 | 能释放活性醛和活性酮的二乙烯基醚衍生物及用于给表面加香的方法 |
| CN111018682A (zh) * | 2019-12-17 | 2020-04-17 | 南通天泽化工有限公司 | 一种柠檬醛的制备方法 |
| US20240199519A1 (en) * | 2021-04-01 | 2024-06-20 | Basf Se | Aryl/alkenyl-pentenal derivatives as aroma chemicals |
| CN114890876B (zh) * | 2022-05-11 | 2023-09-19 | 万华化学集团股份有限公司 | 一种异戊二烯基异戊烯基醚及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905722A (en) * | 1959-09-22 | Preparation of i | ||
| CH479515A (fr) * | 1967-05-26 | 1969-10-15 | Firmenich & Cie | Procédé pour la préparation d'aldéhydes non saturés |
| CH510602A (fr) * | 1967-05-26 | 1971-07-31 | Firmenich & Cie | Procédé pour la préparation de composés carbonylés |
| CH509957A (de) * | 1968-01-23 | 1971-07-15 | Hoffmann La Roche | Verfahren zur Umlagerung von ungesättigten Äthern in ungesättigte Ketoverbindungen |
| DE2157035C3 (de) * | 1971-11-17 | 1974-07-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung höhermolekularer alpha-beta-ungesättigter Aldehyde |
-
1974
- 1974-02-26 CH CH879777A patent/CH597123A5/xx not_active IP Right Cessation
- 1974-02-26 CH CH879677A patent/CH597128A5/xx not_active IP Right Cessation
- 1974-02-26 CH CH879877A patent/CH605515A5/xx not_active IP Right Cessation
- 1974-02-26 CH CH879577A patent/CH598172A5/xx not_active IP Right Cessation
- 1974-02-26 CH CH268874A patent/CH597126A5/xx not_active IP Right Cessation
- 1974-02-26 CH CH879977A patent/CH605510A5/xx not_active IP Right Cessation
- 1974-03-11 FR FR7408182A patent/FR2235904B1/fr not_active Expired
- 1974-03-11 DE DE2411530A patent/DE2411530C2/de not_active Expired
- 1974-03-11 GB GB4462074*A patent/GB1407945A/en not_active Expired
- 1974-03-11 GB GB4461974*A patent/GB1407944A/en not_active Expired
- 1974-03-11 BE BE141841A patent/BE812104A/xx unknown
- 1974-03-11 AT AT199074A patent/AT342016B/de not_active IP Right Cessation
- 1974-03-11 GB GB4461074*A patent/GB1407943A/en not_active Expired
- 1974-03-11 JP JP2727874A patent/JPS549164B2/ja not_active Expired
- 1974-03-11 GB GB1073674A patent/GB1407942A/en not_active Expired
- 1974-03-12 NL NL7403290A patent/NL7403290A/xx not_active Application Discontinuation
- 1974-04-08 IT IT20597/74A patent/IT1007421B/it active
- 1974-12-12 FR FR7440959A patent/FR2246529B1/fr not_active Expired
- 1974-12-12 FR FR7440957A patent/FR2242358B1/fr not_active Expired
- 1974-12-12 FR FR7440958A patent/FR2242357B1/fr not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
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