CN1062259C - 分解环烷基氢过氧化物的方法 - Google Patents
分解环烷基氢过氧化物的方法 Download PDFInfo
- Publication number
- CN1062259C CN1062259C CN96121086A CN96121086A CN1062259C CN 1062259 C CN1062259 C CN 1062259C CN 96121086 A CN96121086 A CN 96121086A CN 96121086 A CN96121086 A CN 96121086A CN 1062259 C CN1062259 C CN 1062259C
- Authority
- CN
- China
- Prior art keywords
- alkali metal
- decomposition
- chhp
- aqueous phase
- weight
- 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
- -1 cycloalkyl hydroperoxide Chemical compound 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000008346 aqueous phase Substances 0.000 claims abstract description 31
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 5
- 150000007513 acids Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 47
- 238000007254 oxidation reaction Methods 0.000 claims description 26
- 230000003647 oxidation Effects 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 150000001924 cycloalkanes Chemical class 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 57
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000004448 titration Methods 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 12
- 239000011651 chromium Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- MFICMDKKOZOGQZ-UHFFFAOYSA-N cyclohexane;cyclohexanone Chemical compound C1CCCCC1.O=C1CCCCC1 MFICMDKKOZOGQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000005882 aldol condensation reaction Methods 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 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
- 238000007865 diluting Methods 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
- C07C27/12—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons with oxygen
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- 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
- 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
- C07C45/53—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 of hydroperoxides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Fire-Extinguishing Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9500853A BE1009662A3 (nl) | 1995-10-13 | 1995-10-13 | Werkwijze voor het ontleden van cycloalkylhydroperoxide. |
| BE9500853 | 1995-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1156714A CN1156714A (zh) | 1997-08-13 |
| CN1062259C true CN1062259C (zh) | 2001-02-21 |
Family
ID=3889235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96121086A Expired - Fee Related CN1062259C (zh) | 1995-10-13 | 1996-10-12 | 分解环烷基氢过氧化物的方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5905173A (enExample) |
| EP (1) | EP0768292B1 (enExample) |
| JP (1) | JP3897384B2 (enExample) |
| KR (1) | KR100446374B1 (enExample) |
| CN (1) | CN1062259C (enExample) |
| AR (1) | AR003877A1 (enExample) |
| AU (1) | AU700696B2 (enExample) |
| BE (1) | BE1009662A3 (enExample) |
| BR (1) | BR9605132A (enExample) |
| CA (1) | CA2187709C (enExample) |
| CO (1) | CO4560461A1 (enExample) |
| CZ (1) | CZ296696A3 (enExample) |
| DE (1) | DE69606128T2 (enExample) |
| ES (1) | ES2143714T3 (enExample) |
| HU (1) | HU216540B (enExample) |
| IL (1) | IL119410A (enExample) |
| MX (1) | MX9604783A (enExample) |
| PL (1) | PL188039B1 (enExample) |
| RU (1) | RU2185366C2 (enExample) |
| SK (1) | SK282415B6 (enExample) |
| TW (1) | TW338762B (enExample) |
| ZA (1) | ZA968565B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1011041A3 (nl) * | 1997-03-12 | 1999-04-06 | Dsm Nv | Werkwijze voor het ontleden van cycloalkylhydroperoxide. |
| US8046256B2 (en) * | 2000-04-14 | 2011-10-25 | American Express Travel Related Services Company, Inc. | System and method for using loyalty rewards as currency |
| US6700022B2 (en) * | 2002-06-05 | 2004-03-02 | E. I. Du Pont De Nemours And Company | High yield cyclohexyl hydroperoxide decompostition process |
| CN101010273B (zh) * | 2004-08-24 | 2010-06-30 | 因维斯塔技术有限公司 | 减少含有环己烯酮的有机混合物中的环己烯酮含量的方法 |
| EA011023B1 (ru) * | 2005-01-25 | 2008-12-30 | ДСМ АйПи АССЕТС Б.В. | Способ получения циклогексанона и циклогексанола |
| US8376224B2 (en) | 2006-05-25 | 2013-02-19 | Sean I. Mcghie | Self-service stations for utilizing non-negotiable credits earned from a game of chance |
| EP2096097B1 (en) * | 2006-12-05 | 2012-08-22 | Daicel Chemical Industries, Ltd. | Method for producing oxidation product of cycloalkane |
| CN103372462B (zh) * | 2012-04-26 | 2016-03-23 | 中国科学院大连化学物理研究所 | 一种分解环烷基过氧化氢水溶性催化剂体系及应用 |
| CN105339332B (zh) * | 2013-04-18 | 2018-04-10 | 罗地亚经营管理公司 | 环烷烃氧化催化剂以及生产醇和酮的方法 |
| CN107108424A (zh) | 2014-10-31 | 2017-08-29 | 宇部兴产株式会社 | 一种酮和/或醇的制造方法及其系统 |
| CN108602736A (zh) | 2015-12-07 | 2018-09-28 | 宇部兴产株式会社 | 制造酮和/或醇的方法及其系统 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2140088A1 (enExample) * | 1971-06-03 | 1973-01-12 | Basf Ag | |
| EP0004105A1 (en) * | 1978-02-25 | 1979-09-19 | Stamicarbon B.V. | Process for preparing cycloalkanols and cycloalkanones |
| EP0092867A1 (en) * | 1982-04-23 | 1983-11-02 | Stamicarbon B.V. | Process for preparing cyclohexanol and cyclohexanone |
| EP0659726A1 (en) * | 1993-12-23 | 1995-06-28 | Dsm N.V. | Process for preparing an alkanone and/or an alkanol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163027A (en) * | 1976-11-06 | 1979-07-31 | Basf Aktiengesellschaft | Working-up of reaction mixtures containing cyclohexanol and cyclohexanone |
| JPS5738735A (en) * | 1980-08-19 | 1982-03-03 | Mitsui Petrochem Ind Ltd | Method for treating hydroperoxide mixture |
| US5206441A (en) * | 1992-04-06 | 1993-04-27 | E. I. Du Pont De Nemours And Company | High rate process for preparation of cyclohexanol and cyclohexanone |
-
1995
- 1995-10-13 BE BE9500853A patent/BE1009662A3/nl not_active IP Right Cessation
-
1996
- 1996-10-03 DE DE69606128T patent/DE69606128T2/de not_active Expired - Lifetime
- 1996-10-03 ES ES96202754T patent/ES2143714T3/es not_active Expired - Lifetime
- 1996-10-03 EP EP96202754A patent/EP0768292B1/en not_active Expired - Lifetime
- 1996-10-09 CO CO96053676A patent/CO4560461A1/es unknown
- 1996-10-09 SK SK1290-96A patent/SK282415B6/sk not_active IP Right Cessation
- 1996-10-10 ZA ZA968565A patent/ZA968565B/xx unknown
- 1996-10-10 CZ CZ962966A patent/CZ296696A3/cs unknown
- 1996-10-11 US US08/729,511 patent/US5905173A/en not_active Expired - Lifetime
- 1996-10-11 RU RU96120364/04A patent/RU2185366C2/ru not_active IP Right Cessation
- 1996-10-11 PL PL31649096A patent/PL188039B1/pl not_active IP Right Cessation
- 1996-10-11 IL IL11941096A patent/IL119410A/xx not_active IP Right Cessation
- 1996-10-11 HU HU9602820A patent/HU216540B/hu not_active IP Right Cessation
- 1996-10-11 CA CA002187709A patent/CA2187709C/en not_active Expired - Fee Related
- 1996-10-11 MX MX9604783A patent/MX9604783A/es unknown
- 1996-10-12 CN CN96121086A patent/CN1062259C/zh not_active Expired - Fee Related
- 1996-10-12 KR KR1019960046012A patent/KR100446374B1/ko not_active Expired - Fee Related
- 1996-10-12 TW TW085112474A patent/TW338762B/zh not_active IP Right Cessation
- 1996-10-14 AU AU68184/96A patent/AU700696B2/en not_active Ceased
- 1996-10-14 AR ARP960104732A patent/AR003877A1/es not_active Application Discontinuation
- 1996-10-14 BR BR9605132A patent/BR9605132A/pt not_active IP Right Cessation
- 1996-10-14 JP JP30541496A patent/JP3897384B2/ja not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2140088A1 (enExample) * | 1971-06-03 | 1973-01-12 | Basf Ag | |
| EP0004105A1 (en) * | 1978-02-25 | 1979-09-19 | Stamicarbon B.V. | Process for preparing cycloalkanols and cycloalkanones |
| EP0092867A1 (en) * | 1982-04-23 | 1983-11-02 | Stamicarbon B.V. | Process for preparing cyclohexanol and cyclohexanone |
| EP0659726A1 (en) * | 1993-12-23 | 1995-06-28 | Dsm N.V. | Process for preparing an alkanone and/or an alkanol |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2143714T3 (es) | 2000-05-16 |
| HUP9602820A2 (en) | 1997-05-28 |
| DE69606128D1 (de) | 2000-02-17 |
| AU6818496A (en) | 1997-04-17 |
| HUP9602820A3 (en) | 1998-04-28 |
| AR003877A1 (es) | 1998-09-09 |
| EP0768292B1 (en) | 2000-01-12 |
| KR970021046A (ko) | 1997-05-28 |
| KR100446374B1 (ko) | 2004-11-03 |
| JP3897384B2 (ja) | 2007-03-22 |
| DE69606128T2 (de) | 2000-08-31 |
| BE1009662A3 (nl) | 1997-06-03 |
| TW338762B (en) | 1998-08-21 |
| BR9605132A (pt) | 1998-07-07 |
| CO4560461A1 (es) | 1998-02-10 |
| SK129096A3 (en) | 1997-05-07 |
| CA2187709A1 (en) | 1997-04-14 |
| HU9602820D0 (en) | 1996-11-28 |
| MX9604783A (es) | 1997-08-30 |
| IL119410A (en) | 2000-11-21 |
| CA2187709C (en) | 2005-03-29 |
| EP0768292A1 (en) | 1997-04-16 |
| SK282415B6 (sk) | 2002-01-07 |
| JPH09194408A (ja) | 1997-07-29 |
| CN1156714A (zh) | 1997-08-13 |
| IL119410A0 (en) | 1997-01-10 |
| CZ296696A3 (en) | 1997-06-11 |
| AU700696B2 (en) | 1999-01-14 |
| US5905173A (en) | 1999-05-18 |
| RU2185366C2 (ru) | 2002-07-20 |
| ZA968565B (en) | 1997-05-13 |
| PL188039B1 (pl) | 2004-11-30 |
| HU216540B (hu) | 1999-07-28 |
| PL316490A1 (en) | 1997-04-14 |
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