CH681721A5 - - Google Patents

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Info

Publication number: CH681721A5
Authority: CH; Switzerland
Prior art keywords: pinene; benzene; terpenes; chr4r5; iii
Prior art date: 1990-02-01

Application number

CH165/91A

Other languages

German (de)

English (en)

Inventor

Thomas Dr Dipl-Chem Berthold

Stephan Dipl-Chem Doerfelt

Guenter Dr Dipl-Chem Haufe

Horst Prof Dr Dipl-Chem Hennig

Peter Dr Dipl-Chem Kemter

Werner Prof Dr Dipl-C Kochmann

Manfred Prof Dr Di Muehlstaedt

Detlef Dr Dipl-Chem Rehorek

Lutz Dr Dipl-Chem Weber

Original Assignee

Bitterfeld Wolfen Chemie

Priority date (The priority date 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 date listed.)

1990-02-01

Filing date

1991-01-21

Publication date

1993-05-14

1991-01-21 Application filed by Bitterfeld Wolfen Chemie filed Critical Bitterfeld Wolfen Chemie

1993-05-14 Publication of CH681721A5 publication Critical patent/CH681721A5/de

Links

UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 26
230000008569 process Effects 0.000 claims description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
229930003658 monoterpene Natural products 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 10
150000003505 terpenes Chemical class 0.000 claims description 9
235000007586 terpenes Nutrition 0.000 claims description 9
-1 monoterpenoid hydrocarbons Chemical class 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
239000003446 ligand Substances 0.000 claims description 4
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
MNSFATSRSQVCJF-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C2C=CC(C(=C3C=CC(=C(C=4C=CC(=C(C5=CC=C1N5)C5=CC=CC=C5)N4)C4=CC=CC=C4)N3)C3=CC=CC=C3)=N2.[Mo] Chemical class C1(=CC=CC=C1)C1=C2C=CC(C(=C3C=CC(=C(C=4C=CC(=C(C5=CC=C1N5)C5=CC=CC=C5)N4)C4=CC=CC=C4)N3)C3=CC=CC=C3)=N2.[Mo] MNSFATSRSQVCJF-UHFFFAOYSA-N 0.000 claims description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
230000009471 action Effects 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003849 aromatic solvent Substances 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
230000005670 electromagnetic radiation Effects 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
239000011572 manganese Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 17
GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 14
230000003647 oxidation Effects 0.000 description 13
238000007254 oxidation reaction Methods 0.000 description 13
239000000047 product Substances 0.000 description 13
UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000007800 oxidant agent Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
150000002773 monoterpene derivatives Chemical class 0.000 description 7
235000002577 monoterpenes Nutrition 0.000 description 7
239000002904 solvent Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WONIGEXYPVIKFS-UHFFFAOYSA-N Verbenol Chemical compound CC1=CC(O)C2C(C)(C)C1C2 WONIGEXYPVIKFS-UHFFFAOYSA-N 0.000 description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
WONIGEXYPVIKFS-VGMNWLOBSA-N (1r,2s,5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol Chemical compound CC1=C[C@H](O)[C@H]2C(C)(C)[C@@H]1C2 WONIGEXYPVIKFS-VGMNWLOBSA-N 0.000 description 4
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical group [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
150000002118 epoxides Chemical class 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000002432 hydroperoxides Chemical class 0.000 description 3
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 3
229910052750 molybdenum Inorganic materials 0.000 description 3
239000011733 molybdenum Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 2
NHMKYUHMPXBMFI-SNVBAGLBSA-N (4s)-2-methyl-6-methylideneocta-2,7-dien-4-ol Chemical compound CC(C)=C[C@@H](O)CC(=C)C=C NHMKYUHMPXBMFI-SNVBAGLBSA-N 0.000 description 2
DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 description 2
DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 description 2
RYOGZVTWMZNTGL-UHFFFAOYSA-N 1,5-dimethylcycloocta-1,5-diene Chemical compound CC1=CCCC(C)=CCC1 RYOGZVTWMZNTGL-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NHMKYUHMPXBMFI-UHFFFAOYSA-N Ipsdienol-d Natural products CC(C)=CC(O)CC(=C)C=C NHMKYUHMPXBMFI-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
238000006701 autoxidation reaction Methods 0.000 description 2
229930006737 car-3-ene Natural products 0.000 description 2
229930007796 carene Natural products 0.000 description 2
BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000006735 epoxidation reaction Methods 0.000 description 2
239000002360 explosive Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
LCYXQUJDODZYIJ-UHFFFAOYSA-N pinocarveol Chemical compound C1C2C(C)(C)C1CC(O)C2=C LCYXQUJDODZYIJ-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
NQFUSWIGRKFAHK-KEMUHUQJSA-N α-pinene-oxide Chemical compound CC12OC1C[C@H]1C(C)(C)[C@@H]2C1 NQFUSWIGRKFAHK-KEMUHUQJSA-N 0.000 description 2
WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Chemical compound CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
239000001169 1-methyl-4-propan-2-ylcyclohexa-1,4-diene Substances 0.000 description 1
RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
IRZWAJHUWGZMMT-UHFFFAOYSA-N Chrysanthenol Natural products CC1=CCC2C(C)(C)C1C2O IRZWAJHUWGZMMT-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005189 alkyl hydroxy group Chemical group 0.000 description 1
XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000005667 attractant Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
229930006722 beta-pinene Natural products 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000031902 chemoattractant activity Effects 0.000 description 1
SSWSYWBRGQINON-UHFFFAOYSA-L cobalt(2+);hexadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O SSWSYWBRGQINON-UHFFFAOYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
BAVONGHXFVOKBV-UHFFFAOYSA-N exo-carveol Natural products CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
YVJRCWCFDJYONJ-UHFFFAOYSA-N hydroperoxymethylbenzene Chemical compound OOCC1=CC=CC=C1 YVJRCWCFDJYONJ-UHFFFAOYSA-N 0.000 description 1
239000002418 insect attractant Substances 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000001699 photocatalysis Effects 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
LCYXQUJDODZYIJ-VGMNWLOBSA-N trans-Pinocarveol Natural products C1[C@@H]2C(C)(C)[C@H]1C[C@H](O)C2=C LCYXQUJDODZYIJ-VGMNWLOBSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- 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
- C07D303/06—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH165/91A 1990-02-01 1991-01-21 CH681721A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD90337460A DD291748A5 (de)	1990-02-01	1990-02-01	Verfahren zur herstellung von allylhydroxylierten terpenoiden kohlenwasserstoffen

Publications (1)

Publication Number	Publication Date
CH681721A5 true CH681721A5 (fr)	1993-05-14

Family

ID=5616192

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH165/91A CH681721A5 (fr)	1990-02-01	1991-01-21

Country Status (4)

Country	Link
CH (1)	CH681721A5 (fr)
DD (1)	DD291748A5 (fr)
DE (1)	DE4101334A1 (fr)
FR (1)	FR2657606A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6815543B1 (en)	1999-08-10	2004-11-09	Warner-Lambert Company	Process for catalyzing the oxidation of organic compounds
CN1367769A (zh) *	1999-08-10	2002-09-04	沃尼尔·朗伯公司	催化有机化合物氧化的方法
GB201720211D0 (en)	2017-12-05	2018-01-17	Givaudan Sa	Improvements in or relating to organic compounds

1990
- 1990-02-01 DD DD90337460A patent/DD291748A5/de not_active IP Right Cessation
1991
- 1991-01-17 DE DE4101334A patent/DE4101334A1/de not_active Withdrawn
- 1991-01-21 CH CH165/91A patent/CH681721A5/de not_active IP Right Cessation
- 1991-02-01 FR FR9101159A patent/FR2657606A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
DD291748A5 (de)	1991-07-11
FR2657606A1 (en)	1991-08-02
DE4101334A1 (de)	1991-08-08

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Date	Code	Title	Description
1994-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0380085B1 (fr)	1992-01-02	Utilisation de composés de rhénium organiques pour l'oxydation de liaisons C-C multiples, des procédés d'oxydation à base de ces composés et de nouveaux composés de rhénium
DE3731690C1 (de)	1989-01-19	Verfahren zur katalytischen Epoxidation von Olefinen mit Wasserstoffperoxid
DE2624104C2 (de)	1986-11-06	Melonalverbindungen, Verfahren zu ihrer Herstellung und Parfümzubereitungen, die diese Verbindungen enthalten
EP0283753A1 (fr)	1988-09-28	Procédé d'époxydation catalytique des oléfines par le peroxyde d'hydrogène
Loubidi et al.	2014	Solvent-free epoxidation of himachalenes and their derivatives by TBHP using [MoO 2 (SAP)] 2 as a catalyst
DE69401820T2 (de)	1997-09-11	Oxidative spaltung von alkenen
Turro et al.	1970	Stereospecific photoreactions of cyclobutanones
DE3539268A1 (de)	1987-05-07	Verfahren zur katalytischen epoxidation von olefinen mit wasserstoffperoxid
DE2239681B2 (de)	1981-02-26	Verfahren zur Epoxidierung von olefinisch ungesättigten Verbindungen mit Wasserstoffperoxid
DE3705785A1 (de)	1988-09-01	Verfahren zur herstellung von polyenaldehyden
DE4101334A1 (de)	1991-08-08	Verfahren zur herstellung von oxygenierten monoterpenoiden kohlenwasserstoffen
DE1593622A1 (de)	1972-04-20	Verfahren zur Herstellung von Riechstoffingredienzien und deren Verwendung
DE1543432B1 (de)	1970-04-09	Verfahren zur Herstellung von vicinalen Diolen
DE1908529A1 (de)	1970-02-19	Verfahren zur Herstellung von Isopren
Schaefer et al.	1963	Chlorination of ketones with selenium oxychloride
DE2111753A1 (de)	1971-10-28	Makrocyclische Verbindungen und Verfahren zu ihrer Herstellung
EP0282708B1 (fr)	1990-09-05	Procédé pour l'époxydation catalytique des oléfines avec le peroxyde d'hydrogène
DE1543001C3 (de)	1979-03-08	Verfahren zur Herstellung von Epoxyden
EP0302993A1 (fr)	1989-02-15	Méthylcyclododécatrièn-1-ols, procédé pour leur fabrication et leur utilisation
Coxon et al.	1977	Photolysis of some β, γ-epoxycarbonyl compounds
Traynham et al.	1962	Addition Reactions with Methylenecyclodecane1a, b
DE2225450C3 (de)	1980-03-20	Verfahren zur gleichzeitigen Herstellung von Propylenoxid und Essigsäure
Thomas et al.	1986	4-(1-hydroperoxy-1-methylethyl)-1, 3-cyclopentadienyl methyl ketone: its formation from α-terpineol and behaviour as a dimethylfulvene epoxide.
DE69309980T2 (de)	1997-11-20	Verfahren zur Herstellung eines Cycloalkanon und/oder einem Cycloalkanol
DE1568763C3 (de)	1976-11-11	Verfahren zur gleichzeitigen Herstellung von Isopren und eines Epoxyds oder eines Acrylate oder eines Oxims