CH623021A5 - Process for the preparation of 6,10,14-trimethylpentadecan-2-one - Google Patents
Process for the preparation of 6,10,14-trimethylpentadecan-2-one Download PDFInfo
- Publication number
- CH623021A5 CH623021A5 CH1129376A CH1129376A CH623021A5 CH 623021 A5 CH623021 A5 CH 623021A5 CH 1129376 A CH1129376 A CH 1129376A CH 1129376 A CH1129376 A CH 1129376A CH 623021 A5 CH623021 A5 CH 623021A5
- Authority
- CH
- Switzerland
- Prior art keywords
- catalyst
- group
- formula
- ppm
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- WHWDWIHXSPCOKZ-UHFFFAOYSA-N hexahydrofarnesyl acetone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)=O WHWDWIHXSPCOKZ-UHFFFAOYSA-N 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- -1 rhodium carbonyl compound Chemical class 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 4
- 238000007037 hydroformylation reaction Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 208000005156 Dehydration Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ITBYWGRSPHMAEE-UHFFFAOYSA-N 3,7,11-trimethyldodeca-6,10-dienal Chemical compound O=CCC(C)CCC=C(C)CCC=C(C)C ITBYWGRSPHMAEE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RYOGZVTWMZNTGL-UDRCNDPASA-N (1z,5z)-1,5-dimethylcycloocta-1,5-diene Chemical compound C\C1=C\CC\C(C)=C/CC1 RYOGZVTWMZNTGL-UDRCNDPASA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- LCRQIJVZGYGHHQ-UHFFFAOYSA-N 1,5-dimethylcyclooctene Chemical compound CC1CCCC(C)=CCC1 LCRQIJVZGYGHHQ-UHFFFAOYSA-N 0.000 description 1
- MXCNYKNYSNAEPA-UHFFFAOYSA-N 2,6,10-trimethylundeca-1,5,9-triene Chemical compound CC(C)=CCCC(C)=CCCC(C)=C MXCNYKNYSNAEPA-UHFFFAOYSA-N 0.000 description 1
- ITMDNOFFRHDSDX-UHFFFAOYSA-N 2,6,10-trimethylundeca-1,9-diene Chemical compound CC(=C)CCCC(C)CCC=C(C)C ITMDNOFFRHDSDX-UHFFFAOYSA-N 0.000 description 1
- IMTLEKVUFSPLHR-UHFFFAOYSA-N 3,7,11-trimethyldodec-10-enal Chemical compound CC(C)=CCCC(C)CCCC(C)CC=O IMTLEKVUFSPLHR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- HQQRKFPNUQQYHT-UHFFFAOYSA-N [SiH4].[P] Chemical compound [SiH4].[P] HQQRKFPNUQQYHT-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- HYERJXDYFLQTGF-UHFFFAOYSA-N rhenium Chemical compound [Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re] HYERJXDYFLQTGF-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB3681775A GB1540227A (en) | 1975-09-08 | 1975-09-08 | Preparation of 6,10,14-trimethylpenta-deca-2-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623021A5 true CH623021A5 (en) | 1981-05-15 |
Family
ID=10391417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1129376A CH623021A5 (en) | 1975-09-08 | 1976-09-06 | Process for the preparation of 6,10,14-trimethylpentadecan-2-one |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6045169B2 (enExample) |
| BE (1) | BE845732A (enExample) |
| CH (1) | CH623021A5 (enExample) |
| DE (1) | DE2640026C2 (enExample) |
| ES (1) | ES451280A1 (enExample) |
| FR (1) | FR2322843A1 (enExample) |
| GB (1) | GB1540227A (enExample) |
| IT (1) | IT1124716B (enExample) |
| NL (1) | NL7609873A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3006867C2 (de) * | 1980-02-23 | 1981-11-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von höheren gesättigten Ketonen |
| US6756411B2 (en) | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| DE19619013A1 (de) * | 1996-05-10 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von Hexahydrofarnesylaceton aus 6,7-Dihydro-geraniol sowie neue Zwischenprodukte für dieses Verfahren |
-
1975
- 1975-09-08 GB GB3681775A patent/GB1540227A/en not_active Expired
-
1976
- 1976-09-01 BE BE1007595A patent/BE845732A/xx not_active IP Right Cessation
- 1976-09-06 IT IT2691876A patent/IT1124716B/it active
- 1976-09-06 NL NL7609873A patent/NL7609873A/xx not_active Application Discontinuation
- 1976-09-06 DE DE19762640026 patent/DE2640026C2/de not_active Expired
- 1976-09-06 ES ES451280A patent/ES451280A1/es not_active Expired
- 1976-09-06 FR FR7626773A patent/FR2322843A1/fr active Granted
- 1976-09-06 CH CH1129376A patent/CH623021A5/de not_active IP Right Cessation
- 1976-09-06 JP JP10587276A patent/JPS6045169B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1540227A (en) | 1979-02-07 |
| NL7609873A (nl) | 1977-03-10 |
| BE845732A (nl) | 1977-03-01 |
| ES451280A1 (es) | 1977-10-01 |
| JPS5233611A (en) | 1977-03-14 |
| FR2322843B1 (enExample) | 1980-11-07 |
| FR2322843A1 (fr) | 1977-04-01 |
| JPS6045169B2 (ja) | 1985-10-08 |
| DE2640026A1 (de) | 1977-03-17 |
| IT1124716B (it) | 1986-05-14 |
| DE2640026C2 (de) | 1985-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1230783B (de) | Verfahren zur Herstellung von Polyenketonen | |
| EP0400509B1 (de) | Verfahren zur Herstellung von Muscon, Zwischenprodukte für dieses Verfahren sowie deren Herstellung | |
| EP0761634B1 (de) | Verfahren zur Herstellung von Pentenalen | |
| EP0010656B1 (de) | Verfahren zur Herstellung von 4-Acyloxy-2-methyl-crotonaldehyden | |
| EP0052775B1 (de) | Verfahren zur Herstellung von Aldehyden und Zwischenprodukte | |
| CH623021A5 (en) | Process for the preparation of 6,10,14-trimethylpentadecan-2-one | |
| EP0100019B1 (de) | Verfahren zur Herstellung von alpha-substituierten beta-Dicarbonyl-, beta-Cyancarbonyl- und beta-Dicyanverbindungen | |
| EP0211205B1 (de) | Verfahren zur Herstellung von 2-Methyl-2-alkenalen | |
| US4011277A (en) | Preparation of squalane by hydrogenolysis | |
| DE10149349A1 (de) | Verfahren zur Herstellung von 6-Methylheptan-2-on und dessen Verwendung | |
| DE2235466C3 (de) | 3-Phenylpropanale und 4-Phenylbutanale sowie ein Verfahren zu deren Herstellung | |
| DE2855506B2 (de) | Verfahren zur Herstellung von Methyl-nomyl-acetaldehyd | |
| DE2219168C3 (de) | 2-Phenyl-butanale und Verfahren zu deren Herstellung | |
| DE2848095A1 (de) | Substituierte perhydro-naphtofurane | |
| DE957942C (de) | Verfahren zur Herstellung von Verbindungen der Vitamin A-Reihe | |
| DE2413170C3 (de) | Diacetylendiol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3602253A1 (de) | Verfahren zur herstellung von 4-monoacetalen des 2-methyl-2-buten-1,4-dials | |
| DE10205835B4 (de) | Verfahren zur Herstellung von Terpinolenaldehyd | |
| EP0252389B1 (de) | 1,1-Dialkoxy-2-methyl-4,4- diacyloxy-2-butene | |
| DE2366306C2 (de) | 1-Methoxy-4-(8-oxy-tricyclo (5.2.1.0↑2,6↑)-decyl-8)-buten-1-in-3, Verfahren zu seiner Herstellung und dessen Verwendung als Zwischenprodukt für Synthese von Riechstoffen | |
| DE1493890C3 (de) | Verfahren zur Herstellung von ß- (5-Nitro-2-furyl)acrolein | |
| DE2900975C2 (de) | 2-Ethyl-3-methyl-pent-4-en-l-al | |
| DE950123C (de) | Verfahren zur Herstellung von 1,1,5,5-Tetraalkoxypentanen | |
| AT206883B (de) | Verfahren zur Herstellung von neuen Cyclododecanderivaten | |
| DE1802428C (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |