SE406461B - Sett att framstella cyklohexanon eller cyklohexanol genom konversion av cyklohexylhydroperoxid med anvendning av fast heterogen kromoxidkatalysator - Google Patents
Sett att framstella cyklohexanon eller cyklohexanol genom konversion av cyklohexylhydroperoxid med anvendning av fast heterogen kromoxidkatalysatorInfo
- Publication number
- SE406461B SE406461B SE737314332A SE7314332A SE406461B SE 406461 B SE406461 B SE 406461B SE 737314332 A SE737314332 A SE 737314332A SE 7314332 A SE7314332 A SE 7314332A SE 406461 B SE406461 B SE 406461B
- Authority
- SE
- Sweden
- Prior art keywords
- catalyst
- chromium
- cyclohexanol
- cyclohexyl hydroperoxide
- oxide
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 50
- 239000003054 catalyst Substances 0.000 title claims description 45
- 238000006243 chemical reaction Methods 0.000 title claims description 29
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 title claims description 27
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 17
- 239000007787 solid Substances 0.000 title description 4
- 239000011651 chromium Substances 0.000 claims description 15
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 4
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001845 chromium compounds Chemical class 0.000 claims description 2
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims 1
- 239000005750 Copper hydroxide Substances 0.000 claims 1
- 229910001956 copper hydroxide Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 238000007254 oxidation reaction Methods 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 230000003647 oxidation Effects 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000002978 peroxides Chemical class 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229910002014 Aerosil® 130 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- 229910000424 chromium(II) oxide Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- -1 cycloalkyl hydroperoxides Chemical class 0.000 description 1
- FYLJKQFMQFOLSZ-UHFFFAOYSA-N cyclohexylperoxycyclohexane Chemical compound C1CCCCC1OOC1CCCCC1 FYLJKQFMQFOLSZ-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- XVOFZWCCFLVFRR-UHFFFAOYSA-N oxochromium Chemical compound [Cr]=O XVOFZWCCFLVFRR-UHFFFAOYSA-N 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C07C45/51—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
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7214299,A NL174247C (nl) | 1972-10-21 | 1972-10-21 | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen door omzetting van een cycloalkylhydroperoxide. |
| NLAANVRAGE7313829,A NL174343C (nl) | 1973-10-09 | 1973-10-09 | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen door omzetting van een cycloalkylhydroperoxide. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE406461B true SE406461B (sv) | 1979-02-12 |
Family
ID=26644818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE737314332A SE406461B (sv) | 1972-10-21 | 1973-10-22 | Sett att framstella cyklohexanon eller cyklohexanol genom konversion av cyklohexylhydroperoxid med anvendning av fast heterogen kromoxidkatalysator |
Country Status (19)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7506790A (nl) * | 1975-06-07 | 1976-12-09 | Stamicarbon | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen. |
| NL7802125A (nl) * | 1978-02-25 | 1979-08-28 | Stamicarbon | Werkwijze voor het bereiden van cycloalkanolen en cycloalkanonen. |
| DE3222144A1 (de) * | 1982-06-11 | 1983-12-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von cyclohexanol und cyclohexanon |
| EP0144467A1 (en) * | 1983-11-29 | 1985-06-19 | The Procter & Gamble Company | Catalyst system and its use in hydrogenation of N,N-disubstituted amides to amines |
| FR2744719B1 (fr) * | 1996-02-09 | 1998-04-10 | Rhone Poulenc Fibres | Procede de decomposition catalytique des hydroperoxydes organiques |
| RU2154050C1 (ru) * | 1999-01-19 | 2000-08-10 | Ярославский государственный технический университет | Способ получения циклоалканонов c8-c12 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2851496A (en) * | 1954-07-27 | 1958-09-09 | Du Pont | Preparation of oxidation products of cyclohexane |
| FR2070977A5 (enrdf_load_stackoverflow) * | 1969-12-12 | 1971-09-17 | Rhone Poulenc Sa |
-
1973
- 1973-10-16 IL IL43433A patent/IL43433A/en unknown
- 1973-10-16 AT AT879773A patent/AT327166B/de not_active IP Right Cessation
- 1973-10-16 GB GB4814273A patent/GB1439210A/en not_active Expired
- 1973-10-17 AU AU61472/73A patent/AU476087B2/en not_active Expired
- 1973-10-18 CH CH1472473A patent/CH598164A5/xx not_active IP Right Cessation
- 1973-10-18 DE DE2352378A patent/DE2352378C2/de not_active Expired
- 1973-10-19 HU HUSA2546A patent/HU168685B/hu unknown
- 1973-10-19 DD DD174183A patent/DD108264A5/xx unknown
- 1973-10-19 IT IT7353231A patent/IT1000085B/it active
- 1973-10-19 CA CA183,699A patent/CA1012985A/en not_active Expired
- 1973-10-19 JP JP48117691A patent/JPS5851934B2/ja not_active Expired
- 1973-10-19 FR FR7337426A patent/FR2208868B1/fr not_active Expired
- 1973-10-20 BG BG024802A patent/BG27057A3/xx unknown
- 1973-10-20 ES ES419829A patent/ES419829A1/es not_active Expired
- 1973-10-22 SE SE737314332A patent/SE406461B/sv unknown
- 1973-10-22 PL PL1973166006A patent/PL98598B1/pl unknown
- 1973-10-22 AR AR250619A patent/AR196460A1/es active
- 1973-10-22 RO RO7300076395A patent/RO63671A/ro unknown
- 1973-10-22 CS CS7300007258A patent/CS179431B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS179431B2 (en) | 1977-10-31 |
| HU168685B (enrdf_load_stackoverflow) | 1976-06-28 |
| AT327166B (de) | 1976-01-26 |
| AU476087B2 (en) | 1976-09-09 |
| AR196460A1 (es) | 1973-12-27 |
| RO63671A (fr) | 1978-10-15 |
| DE2352378C2 (de) | 1984-05-10 |
| BG27057A3 (bg) | 1979-08-15 |
| FR2208868A1 (enrdf_load_stackoverflow) | 1974-06-28 |
| FR2208868B1 (enrdf_load_stackoverflow) | 1978-02-10 |
| ATA879773A (de) | 1975-04-15 |
| DD108264A5 (enrdf_load_stackoverflow) | 1974-09-12 |
| DE2352378A1 (de) | 1974-05-16 |
| IL43433A0 (en) | 1974-01-14 |
| JPS5851934B2 (ja) | 1983-11-19 |
| CA1012985A (en) | 1977-06-28 |
| GB1439210A (en) | 1976-06-16 |
| CH598164A5 (enrdf_load_stackoverflow) | 1978-04-28 |
| IT1000085B (it) | 1976-03-30 |
| JPS4993338A (enrdf_load_stackoverflow) | 1974-09-05 |
| IL43433A (en) | 1976-09-30 |
| PL98598B1 (pl) | 1978-05-31 |
| AU6147273A (en) | 1975-04-17 |
| ES419829A1 (es) | 1976-05-01 |
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