DE1958643C - - Google Patents
Info
- Publication number
- DE1958643C DE1958643C DE19691958643 DE1958643A DE1958643C DE 1958643 C DE1958643 C DE 1958643C DE 19691958643 DE19691958643 DE 19691958643 DE 1958643 A DE1958643 A DE 1958643A DE 1958643 C DE1958643 C DE 1958643C
- Authority
- DE
- Germany
- Prior art keywords
- palladium
- reaction vessel
- catalyst
- bed
- active metal
- 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
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 54
- 229910052763 palladium Inorganic materials 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 description 6
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 3
- IRPFOXRBPHCCTG-UHFFFAOYSA-N 8-hydroxy-6,8-dimethyl-3-methylidenespiro[4,5,6,8a-tetrahydro-3ah-cyclohepta[b]furan-7,5'-oxolane]-2,2'-dione Chemical compound CC1CCC(C(C(=O)O2)=C)C2C(C)(O)C11CCC(=O)O1 IRPFOXRBPHCCTG-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- SRSGVKWWVXWSJT-ATVHPVEESA-N 5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C(C)C=1C(=O)NCCN1CCCC1 SRSGVKWWVXWSJT-ATVHPVEESA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 229910004489 SiLi Inorganic materials 0.000 description 1
- 239000003819 Toceranib Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- WDNQRCVBPNOTNV-UHFFFAOYSA-N dinonylnaphthylsulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 WDNQRCVBPNOTNV-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940090244 palladia Drugs 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR174736 | 1968-11-21 | ||
| FR174736 | 1968-11-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1958643A1 DE1958643A1 (de) | 1970-05-27 |
| DE1958643C true DE1958643C (cs) | 1973-04-26 |
Family
ID=8657208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691958643 Granted DE1958643A1 (de) | 1968-11-21 | 1969-11-21 | Verfahren zur Hydrierung von Cycloalkanhydroperoxyden |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3694511A (cs) |
| AT (1) | AT296250B (cs) |
| BE (1) | BE741994A (cs) |
| BR (1) | BR6914405D0 (cs) |
| DE (1) | DE1958643A1 (cs) |
| FR (1) | FR1592716A (cs) |
| GB (1) | GB1221629A (cs) |
| LU (1) | LU59847A1 (cs) |
| NL (1) | NL161125C (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1049041A (en) * | 1972-11-23 | 1979-02-20 | Stamicarbon B.V. | Process for the preparation of cycloalkanones and/or cycloalkanols |
| NL7215853A (cs) * | 1972-11-23 | 1974-05-27 | ||
| US4422954A (en) * | 1982-03-31 | 1983-12-27 | Allied Corporation | Method to restore the metal content of a noble metal hydrogenation catalyst |
| US4720592A (en) * | 1986-09-05 | 1988-01-19 | E. I. Du Pont De Nemours And Company | Preparation of cyclohexanone and cyclohexanol |
| US5780683A (en) * | 1996-09-11 | 1998-07-14 | Abb Lummus Global Inc. | Cyclohexane oxidation |
| WO2014014464A1 (en) | 2012-07-19 | 2014-01-23 | Invista Technologies S.A R.L. | Process for the oxidation of cyclohexane |
| JP2015528741A (ja) | 2012-07-19 | 2015-10-01 | インヴィスタ テクノロジーズ エスアエルエル | 水素化触媒の再生 |
| EP2874983A1 (en) * | 2012-07-19 | 2015-05-27 | Invista Technologies S.à.r.l. | Process for the purification of a cyclohexane air oxidation product stream |
| US20160176813A1 (en) | 2012-07-19 | 2016-06-23 | Invista North America S.A R.L. | Process for the oxidation of cyclohexane |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2497349A (en) * | 1947-08-01 | 1950-02-14 | Union Oil Co | Production of alicyclic alcohols |
| US2851496A (en) * | 1954-07-27 | 1958-09-09 | Du Pont | Preparation of oxidation products of cyclohexane |
| FR1505363A (fr) * | 1966-04-20 | 1967-12-15 | Rhone Poulenc Sa | Perfectionnement à la préparation des cycloalcanols et des mélanges cycloalcanols/cycloalcanones |
-
1968
- 1968-11-21 FR FR174736A patent/FR1592716A/fr not_active Expired
-
1969
- 1969-11-13 NL NL6917093.A patent/NL161125C/xx active
- 1969-11-20 BE BE741994D patent/BE741994A/xx unknown
- 1969-11-20 LU LU59847D patent/LU59847A1/xx unknown
- 1969-11-20 US US878543A patent/US3694511A/en not_active Expired - Lifetime
- 1969-11-20 GB GB56964/69A patent/GB1221629A/en not_active Expired
- 1969-11-21 DE DE19691958643 patent/DE1958643A1/de active Granted
- 1969-11-21 AT AT10918/69A patent/AT296250B/de not_active IP Right Cessation
- 1969-11-21 BR BR214405/69A patent/BR6914405D0/pt unknown
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