DE69314054T2 - Verfahren zur kontinuierlichen herstellung von gemischen aus einem cycloalkanon, einem cycloalkanol und einem cycloalkylhydroperoxid - Google Patents
Verfahren zur kontinuierlichen herstellung von gemischen aus einem cycloalkanon, einem cycloalkanol und einem cycloalkylhydroperoxidInfo
- Publication number
- DE69314054T2 DE69314054T2 DE69314054T DE69314054T DE69314054T2 DE 69314054 T2 DE69314054 T2 DE 69314054T2 DE 69314054 T DE69314054 T DE 69314054T DE 69314054 T DE69314054 T DE 69314054T DE 69314054 T2 DE69314054 T2 DE 69314054T2
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- mol
- process according
- oxidation
- concentration
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 238000010924 continuous production Methods 0.000 title claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 33
- 230000003647 oxidation Effects 0.000 claims abstract description 27
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 150000002989 phenols Chemical class 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 239000007789 gas Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- -1 cycloalkyl hydroperoxide Chemical compound 0.000 claims description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000654 additive Substances 0.000 description 27
- 230000000996 additive effect Effects 0.000 description 27
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 26
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 18
- GPHZOCJETVZYTP-UHFFFAOYSA-N hydroperoxycyclododecane Chemical compound OOC1CCCCCCCCCCC1 GPHZOCJETVZYTP-UHFFFAOYSA-N 0.000 description 16
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 15
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 14
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 3
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 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
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
-
- 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
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9201101A BE1006451A3 (nl) | 1992-12-16 | 1992-12-16 | Werkwijze voor de continue bereiding van een mengsel van een cycloalkanon, cycloalkanol en een cycloalkylhydroperoxide. |
| PCT/NL1993/000259 WO1994013613A1 (en) | 1992-12-16 | 1993-12-02 | Method for the continuous preparation of a mixture of a cycloalkanone, cycloalkanol and a cycloalkylhydroperoxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69314054D1 DE69314054D1 (de) | 1997-10-23 |
| DE69314054T2 true DE69314054T2 (de) | 1998-04-02 |
Family
ID=3886588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69314054T Expired - Fee Related DE69314054T2 (de) | 1992-12-16 | 1993-12-02 | Verfahren zur kontinuierlichen herstellung von gemischen aus einem cycloalkanon, einem cycloalkanol und einem cycloalkylhydroperoxid |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5406001A (enExample) |
| EP (1) | EP0674613B1 (enExample) |
| JP (1) | JPH08504437A (enExample) |
| KR (1) | KR100299587B1 (enExample) |
| CN (1) | CN1058478C (enExample) |
| AT (1) | ATE158271T1 (enExample) |
| BE (1) | BE1006451A3 (enExample) |
| BR (1) | BR9307663A (enExample) |
| DE (1) | DE69314054T2 (enExample) |
| ES (1) | ES2108968T3 (enExample) |
| MX (1) | MX9308018A (enExample) |
| PL (1) | PL174275B1 (enExample) |
| RU (1) | RU2116290C1 (enExample) |
| TW (1) | TW277055B (enExample) |
| UA (1) | UA35602C2 (enExample) |
| WO (1) | WO1994013613A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2127248C1 (ru) * | 1997-08-05 | 1999-03-10 | Институт химии нефти СО РАН | Способ получения циклогексанола и циклогексанона |
| RU2402520C1 (ru) * | 2009-05-28 | 2010-10-27 | Институт Катализа Им. Г.К. Борескова Сибирского Отделения Российской Академии Наук | Способ получения смеси циклогексанола и циклогексанона |
| EP3050869B1 (de) * | 2015-01-30 | 2019-10-02 | Symrise AG | Verfahren zur Herstellung von substituierten Alkylcycloalkanonen |
| RU2020128668A (ru) * | 2018-01-30 | 2022-02-28 | Басф Се | Способ окисления циклоалканов |
| RU2747484C1 (ru) * | 2020-10-27 | 2021-05-05 | Публичное акционерное общество "КуйбышевАзот" | Способ получения гидропероксида циклогексила |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU197555A1 (ru) * | 1965-06-16 | 1983-09-15 | Государственный Научно-Исследовательский Институт Органических Полупродуктов И Красителей | Способ получени альдегидов или кетонов |
| US3949004A (en) * | 1971-03-16 | 1976-04-06 | Atlantic Richfield Company | Hydroperoxide production |
| SU686329A1 (ru) * | 1977-12-15 | 1982-05-07 | Предприятие П/Я Р-6603 | Способ получени гидроперекиси циклододецила Б.Я.Ладыгина |
| SU799325A1 (ru) * | 1978-01-30 | 1982-05-07 | Предприятие П/Я Р-6603 | Способ получени гидроперекисей циклоалкилов Б.Я.Ладыгина |
| US5220075A (en) * | 1992-07-17 | 1993-06-15 | Abb Lummus Crest Inc. | Initiated peroxidation of secondary carbon in alkanes and cycloalkanes |
-
1992
- 1992-12-16 BE BE9201101A patent/BE1006451A3/nl not_active IP Right Cessation
-
1993
- 1993-11-29 TW TW082110062A patent/TW277055B/zh active
- 1993-12-02 JP JP6514007A patent/JPH08504437A/ja active Pending
- 1993-12-02 KR KR1019950702515A patent/KR100299587B1/ko not_active Expired - Fee Related
- 1993-12-02 EP EP94903137A patent/EP0674613B1/en not_active Expired - Lifetime
- 1993-12-02 WO PCT/NL1993/000259 patent/WO1994013613A1/en not_active Ceased
- 1993-12-02 DE DE69314054T patent/DE69314054T2/de not_active Expired - Fee Related
- 1993-12-02 UA UA95062797A patent/UA35602C2/uk unknown
- 1993-12-02 BR BR9307663A patent/BR9307663A/pt not_active IP Right Cessation
- 1993-12-02 PL PL93309345A patent/PL174275B1/pl unknown
- 1993-12-02 ES ES94903137T patent/ES2108968T3/es not_active Expired - Lifetime
- 1993-12-02 RU RU95114380A patent/RU2116290C1/ru active
- 1993-12-02 AT AT94903137T patent/ATE158271T1/de not_active IP Right Cessation
- 1993-12-15 CN CN93112701A patent/CN1058478C/zh not_active Expired - Fee Related
- 1993-12-15 US US08/166,344 patent/US5406001A/en not_active Expired - Fee Related
- 1993-12-15 MX MX9308018A patent/MX9308018A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5406001A (en) | 1995-04-11 |
| RU2116290C1 (ru) | 1998-07-27 |
| MX9308018A (es) | 1994-08-31 |
| BE1006451A3 (nl) | 1994-08-30 |
| WO1994013613A1 (en) | 1994-06-23 |
| DE69314054D1 (de) | 1997-10-23 |
| JPH08504437A (ja) | 1996-05-14 |
| RU95114380A (ru) | 1997-06-10 |
| BR9307663A (pt) | 1999-06-29 |
| TW277055B (enExample) | 1996-06-01 |
| ATE158271T1 (de) | 1997-10-15 |
| UA35602C2 (uk) | 2001-04-16 |
| EP0674613A1 (en) | 1995-10-04 |
| CN1058478C (zh) | 2000-11-15 |
| EP0674613B1 (en) | 1997-09-17 |
| CN1096026A (zh) | 1994-12-07 |
| PL174275B1 (pl) | 1998-07-31 |
| KR950704223A (ko) | 1995-11-17 |
| PL309345A1 (en) | 1995-10-02 |
| ES2108968T3 (es) | 1998-01-01 |
| KR100299587B1 (ko) | 2001-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69309942T2 (de) | Verfahren zur herstellung von adipic säure und anderen aliphatischen dibasischen säuren | |
| DE1251763B (de) | Verfahren zur Herstellung von gesattigten aliphatischen Carbonsauren, Alkoholen und/oder Ketonen | |
| DE69815580T2 (de) | Verfahren zur Oxidation von Kohlenwasserstoffen, Alkoholen und/oder Ketonen | |
| DE69606128T2 (de) | Verfahren zur Zersetzung von Cycloalkylhydroperoxid | |
| EP0020952A1 (de) | Verfahren zur Herstellung von Epsilon-Caprolacton aus Cyclohexanon und Perpropionsäure | |
| DE60005317T2 (de) | Verfahren zur oxidation von cycloalkanen, cycloalkoholen und/oder cycloketonen | |
| DE1030831B (de) | Verfahren zur Herstellung tertiaerer aromatischer Hydroperoxyde | |
| DE69201756T2 (de) | Verfahren zur gleichzeitigen Herstellung von Arylformiat und von aromatischer Carbonsäure. | |
| EP0499054B1 (de) | Kreislaufverfahren zur Herstellung von Cyclohexenoxid sowie Cyclohexanol und Cyclohexanon | |
| US4658056A (en) | Catalytic oxidation of liquid cycloparaffins | |
| EP0674613B1 (en) | Method for the continuous preparation of a mixture of a cycloalkanone, cycloalkanol and a cycloalkylhydroperoxide | |
| DE920127C (de) | Verfahren zur Herstellung von Cyclohexanonoxim durch Oxydation von Cyclohexylhydroxylamin | |
| DE69215037T2 (de) | Verfahren zur gleichzeitigen Herstellung eines Lactons und einer aromatischen Carbonsäure | |
| DE19946886A1 (de) | Verfahren zur Herstellung von Phenol | |
| DE69309980T2 (de) | Verfahren zur Herstellung eines Cycloalkanon und/oder einem Cycloalkanol | |
| DE1299624B (de) | Verfahren zur Herstellung von Adipinsaeure | |
| DE962527C (de) | Verfahren zur Herstellung von Oxyhydroperoxyden | |
| DE2253963C3 (de) | Verfahren zur Herstellung von Lactonen | |
| DE1040551B (de) | Verfahren zur Herstellung von tertiaeren Arylhydroperoxyden | |
| DE1111177B (de) | Verfahren zur Herstellung von Cyclododecanon und Cyclododecanol | |
| DE1518970C3 (de) | Verfahren zur Herstellung von gesättigten aliphatischen Dicarbonsäuren | |
| DE1468572A1 (de) | Verfahren zur Herstellung von Adipinsaeure | |
| DE1246723B (de) | Verfahren zur Herstellung alicyclischer Alkohole | |
| DE1418711A1 (de) | Verfahren zur Herstellung von epsilon-Hydroxycapronsaeure | |
| DE1190926B (de) | Verfahren zur Herstellung von Olefinoxyden und Carbonsaeuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |