DE2508778A1 - Verfahren zur herstellung von oxoverbindungen - Google Patents
Verfahren zur herstellung von oxoverbindungenInfo
- Publication number
- DE2508778A1 DE2508778A1 DE19752508778 DE2508778A DE2508778A1 DE 2508778 A1 DE2508778 A1 DE 2508778A1 DE 19752508778 DE19752508778 DE 19752508778 DE 2508778 A DE2508778 A DE 2508778A DE 2508778 A1 DE2508778 A1 DE 2508778A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- hydroxy
- yne
- phenyl
- cycloalkyl
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 2,6,6-trimethyl-cyclohex-1-en-1-yl Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 239000007858 starting material Substances 0.000 claims description 25
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 238000006317 isomerization reaction Methods 0.000 claims description 15
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005662 Paraffin oil Substances 0.000 claims description 7
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- CEBKHWWANWSNTI-UHFFFAOYSA-N ethynyldimethylcarbinol Natural products CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229920002545 silicone oil Polymers 0.000 claims description 4
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 claims description 3
- JJRIKWAHJMMDSF-UHFFFAOYSA-N 2,6-dimethyloct-7-yne-2,6-diol Chemical compound CC(C)(O)CCCC(C)(O)C#C JJRIKWAHJMMDSF-UHFFFAOYSA-N 0.000 claims description 3
- LHHVZFCBJPLCCS-UHFFFAOYSA-N 8-ethynyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol Chemical compound C1C(C)(C)C(C#C)(O)C(C)=CC21OCCO2 LHHVZFCBJPLCCS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005333 aroyloxy group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- UIGLAZDLBZDVBL-UHFFFAOYSA-N 1-phenylprop-2-yn-1-ol Chemical compound C#CC(O)C1=CC=CC=C1 UIGLAZDLBZDVBL-UHFFFAOYSA-N 0.000 claims description 2
- AWSIETBOWGIMBS-UHFFFAOYSA-N 2-methylhept-3-yn-2-ol Chemical compound CCCC#CC(C)(C)O AWSIETBOWGIMBS-UHFFFAOYSA-N 0.000 claims description 2
- MRVYXSMGQBQJHH-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloct-1-yn-3-ol Chemical compound COC(C)(C)CCCC(C)(O)C#C MRVYXSMGQBQJHH-UHFFFAOYSA-N 0.000 claims description 2
- YWTIDNZYLFTNQQ-UHFFFAOYSA-N Dehydrolinalool Chemical compound CC(C)=CCCC(C)(O)C#C YWTIDNZYLFTNQQ-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 description 13
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 description 12
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 11
- 229940043350 citral Drugs 0.000 description 11
- 230000007717 exclusion Effects 0.000 description 11
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- OSLJEVNBEBYYSH-UHFFFAOYSA-N [O-2].C[Si](C)(C)O[V+2](O[Si](C)(C)C)O[Si](C)(C)C Chemical compound [O-2].C[Si](C)(C)O[V+2](O[Si](C)(C)C)O[Si](C)(C)C OSLJEVNBEBYYSH-UHFFFAOYSA-N 0.000 description 6
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- YHRUHBBTQZKMEX-UHFFFAOYSA-N (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-al Natural products CC(C)=CCCC(C)=CCCC(C)=CC=O YHRUHBBTQZKMEX-UHFFFAOYSA-N 0.000 description 3
- WVUGWXCPDFBOFK-UHFFFAOYSA-N 2-hydroxy-2,5-dimethylhex-4-en-3-one Chemical compound CC(C)=CC(=O)C(C)(C)O WVUGWXCPDFBOFK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- LNCSOTXUHPCOQD-UHFFFAOYSA-N [O-2].C1=CC(F)=CC=C1[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)O[V+2](O[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)C=1C=CC(F)=CC=1)O[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 Chemical compound [O-2].C1=CC(F)=CC=C1[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)O[V+2](O[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)C=1C=CC(F)=CC=1)O[Si](C=1C=CC(F)=CC=1)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 LNCSOTXUHPCOQD-UHFFFAOYSA-N 0.000 description 3
- AAXILUCBQRGWQB-UHFFFAOYSA-N acetylene;methanol Chemical group OC.C#C AAXILUCBQRGWQB-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- LKANTOFAXAPZMU-UHFFFAOYSA-N bis(4-bromo-3-nitrophenyl)-(4-bromophenyl)-hydroxysilane Chemical compound C=1C=C(Br)C([N+]([O-])=O)=CC=1[Si](C=1C=C(C(Br)=CC=1)[N+]([O-])=O)(O)C1=CC=C(Br)C=C1 LKANTOFAXAPZMU-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- RAFZYSUICBQABU-UHFFFAOYSA-N phytenal Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)=CC=O RAFZYSUICBQABU-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RSOLKEXGKINTAP-UHFFFAOYSA-N tris(4-bromophenyl)-hydroxysilane Chemical compound C=1C=C(Br)C=CC=1[Si](C=1C=CC(Br)=CC=1)(O)C1=CC=C(Br)C=C1 RSOLKEXGKINTAP-UHFFFAOYSA-N 0.000 description 3
- KATYCWCEYHXSPW-UHFFFAOYSA-N tris(4-fluorophenyl)-hydroxysilane Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(O)C1=CC=C(F)C=C1 KATYCWCEYHXSPW-UHFFFAOYSA-N 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- IHJUECRFYCQBMW-UHFFFAOYSA-N 2,5-dimethylhex-3-yne-2,5-diol Chemical compound CC(C)(O)C#CC(C)(C)O IHJUECRFYCQBMW-UHFFFAOYSA-N 0.000 description 2
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 2
- HFFCMXBSDHGUPP-UHFFFAOYSA-N 7-hydroxy-3,7-dimethyloct-2-enal Chemical compound O=CC=C(C)CCCC(C)(C)O HFFCMXBSDHGUPP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 2
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WZAWFNKJAGZLGG-UHFFFAOYSA-N 2-(7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ylidene)acetaldehyde Chemical compound C1C(C)(C)C(=CC=O)C(C)=CC21OCCO2 WZAWFNKJAGZLGG-UHFFFAOYSA-N 0.000 description 1
- FKMGZMDLSNOJPQ-UHFFFAOYSA-N 2-methylhept-2-en-4-one Chemical compound CCCC(=O)C=C(C)C FKMGZMDLSNOJPQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZNVPGYAGXVEAFP-UHFFFAOYSA-N 3,7,11-trimethyldodeca-6,10-dien-1-yn-3-ol Chemical compound CC(C)=CCCC(C)=CCCC(C)(O)C#C ZNVPGYAGXVEAFP-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- IENXNRSNFXHIOR-UHFFFAOYSA-N 4-ethynyl-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one Chemical compound CC1=CC(=O)CC(C)(C)C1(O)C#C IENXNRSNFXHIOR-UHFFFAOYSA-N 0.000 description 1
- VXEVZBLWVNIBAN-UHFFFAOYSA-N 7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one Chemical compound C1C(C)(C)C(=O)C(C)=CC21OCCO2 VXEVZBLWVNIBAN-UHFFFAOYSA-N 0.000 description 1
- GLXHKKYXDUMQEP-UHFFFAOYSA-N 7-ethynyl-6,6,8-trimethyl-2,3,4a,5-tetrahydro-1,4-benzodioxin-7-ol Chemical compound O1CCOC2CC(C)(C)C(C#C)(O)C(C)=C21 GLXHKKYXDUMQEP-UHFFFAOYSA-N 0.000 description 1
- AMLBMXAXWXKAFL-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloct-2-enal Chemical compound COC(C)(C)CCCC(C)=CC=O AMLBMXAXWXKAFL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YHRUHBBTQZKMEX-FBXUGWQNSA-N E,E-Farnesal Natural products CC(C)=CCC\C(C)=C/CC\C(C)=C/C=O YHRUHBBTQZKMEX-FBXUGWQNSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RAFZYSUICBQABU-QYLFUYDXSA-N Phytal Natural products CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C/C=O RAFZYSUICBQABU-QYLFUYDXSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- NNRRSGVORFXXAA-UHFFFAOYSA-N [O-2].BrC1=CC=C(C=C1)[Si](O[V+2](OC1CCCCC1)O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br Chemical compound [O-2].BrC1=CC=C(C=C1)[Si](O[V+2](OC1CCCCC1)O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br NNRRSGVORFXXAA-UHFFFAOYSA-N 0.000 description 1
- WTWABVGPQHMVAF-UHFFFAOYSA-N [O-2].BrC1=CC=C(C=C1)[Si](O[V+2](O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br Chemical compound [O-2].BrC1=CC=C(C=C1)[Si](O[V+2](O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)O[Si](C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br WTWABVGPQHMVAF-UHFFFAOYSA-N 0.000 description 1
- OTMOEOOGWJWTTR-UHFFFAOYSA-N [O-2].C1=CC(Cl)=CC=C1[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)O[V+2](O[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)C=1C=CC(Cl)=CC=1)O[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 Chemical compound [O-2].C1=CC(Cl)=CC=C1[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)O[V+2](O[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)C=1C=CC(Cl)=CC=1)O[Si](C=1C=CC(Cl)=CC=1)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OTMOEOOGWJWTTR-UHFFFAOYSA-N 0.000 description 1
- FKGHWNDBCMNYSO-UHFFFAOYSA-N [O-2].FC1=CC=C(C=C1)[Si](O[V+2](O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)O[Si](C1=CC=C(C=C1)F)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F Chemical compound [O-2].FC1=CC=C(C=C1)[Si](O[V+2](O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)O[Si](C1=CC=C(C=C1)F)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F FKGHWNDBCMNYSO-UHFFFAOYSA-N 0.000 description 1
- JWSGVTZYXYLKTO-UHFFFAOYSA-N [O-2].[N+](=O)([O-])C=1C=C(C=CC1Br)[Si](O[V+2](O[Si](C1=CC(=C(C=C1)Br)[N+](=O)[O-])(C1=CC(=C(C=C1)Br)[N+](=O)[O-])C1=CC=C(C=C1)Br)O[Si](C1=CC(=C(C=C1)Br)[N+](=O)[O-])(C1=CC(=C(C=C1)Br)[N+](=O)[O-])C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC(=C(C=C1)Br)[N+](=O)[O-] Chemical compound [O-2].[N+](=O)([O-])C=1C=C(C=CC1Br)[Si](O[V+2](O[Si](C1=CC(=C(C=C1)Br)[N+](=O)[O-])(C1=CC(=C(C=C1)Br)[N+](=O)[O-])C1=CC=C(C=C1)Br)O[Si](C1=CC(=C(C=C1)Br)[N+](=O)[O-])(C1=CC(=C(C=C1)Br)[N+](=O)[O-])C1=CC=C(C=C1)Br)(C1=CC=C(C=C1)Br)C1=CC(=C(C=C1)Br)[N+](=O)[O-] JWSGVTZYXYLKTO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- ZPUOOELCBXBZSG-UHFFFAOYSA-N hydroxy-tris(4-phenylphenyl)silane Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1[Si](C=1C=CC(=CC=1)C=1C=CC=CC=1)(O)C(C=C1)=CC=C1C1=CC=CC=C1 ZPUOOELCBXBZSG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 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
- IDNFOHGUHGBMOE-UHFFFAOYSA-N nitrobenzene;toluene Chemical compound CC1=CC=CC=C1.[O-][N+](=O)C1=CC=CC=C1 IDNFOHGUHGBMOE-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 235000020945 retinal Nutrition 0.000 description 1
- 239000011604 retinal Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- VVDGQDUYQCOQET-UHFFFAOYSA-N triphenylsilyl acetate Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC(=O)C)C1=CC=CC=C1 VVDGQDUYQCOQET-UHFFFAOYSA-N 0.000 description 1
- BOOSXZFEJKXIHK-UHFFFAOYSA-N tris(4-chlorophenyl)-hydroxysilane Chemical compound C=1C=C(Cl)C=CC=1[Si](C=1C=CC(Cl)=CC=1)(O)C1=CC=C(Cl)C=C1 BOOSXZFEJKXIHK-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- 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
- C07C45/512—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 a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/56—Vanadium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (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 |
|---|---|---|---|
| CH293274A CH601156A5 (enrdf_load_stackoverflow) | 1974-03-01 | 1974-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2508778A1 true DE2508778A1 (de) | 1975-09-04 |
Family
ID=4244866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752508778 Withdrawn DE2508778A1 (de) | 1974-03-01 | 1975-02-28 | Verfahren zur herstellung von oxoverbindungen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS548649B2 (enrdf_load_stackoverflow) |
| AT (1) | AT338226B (enrdf_load_stackoverflow) |
| BE (1) | BE826112A (enrdf_load_stackoverflow) |
| CH (1) | CH601156A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2508778A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2272971B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1481577A (enrdf_load_stackoverflow) |
| NL (1) | NL163496C (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4153615A (en) * | 1978-03-27 | 1979-05-08 | Hoffmann-La Roche Inc. | Method of producing coloring agents |
-
1974
- 1974-03-01 CH CH293274A patent/CH601156A5/xx not_active IP Right Cessation
-
1975
- 1975-01-27 NL NL7500922.A patent/NL163496C/xx active
- 1975-02-27 JP JP2349075A patent/JPS548649B2/ja not_active Expired
- 1975-02-28 GB GB8445/75A patent/GB1481577A/en not_active Expired
- 1975-02-28 FR FR7506312A patent/FR2272971B1/fr not_active Expired
- 1975-02-28 DE DE19752508778 patent/DE2508778A1/de not_active Withdrawn
- 1975-02-28 BE BE153849A patent/BE826112A/xx unknown
- 1975-02-28 AT AT158975A patent/AT338226B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1481577A (en) | 1977-08-03 |
| JPS548649B2 (enrdf_load_stackoverflow) | 1979-04-17 |
| CH601156A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| NL163496B (nl) | 1980-04-15 |
| NL7500922A (nl) | 1975-09-03 |
| FR2272971A1 (enrdf_load_stackoverflow) | 1975-12-26 |
| JPS50117709A (enrdf_load_stackoverflow) | 1975-09-16 |
| NL163496C (nl) | 1980-09-15 |
| AT338226B (de) | 1977-08-10 |
| FR2272971B1 (enrdf_load_stackoverflow) | 1978-02-24 |
| BE826112A (fr) | 1975-08-28 |
| ATA158975A (de) | 1976-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |