DE2143757A1 - Verfahren zur herstellung von cycloalkanol und cycloalkanon durch oxydation von cycloalkan - Google Patents
Verfahren zur herstellung von cycloalkanol und cycloalkanon durch oxydation von cycloalkanInfo
- Publication number
- DE2143757A1 DE2143757A1 DE2143757A DE2143757A DE2143757A1 DE 2143757 A1 DE2143757 A1 DE 2143757A1 DE 2143757 A DE2143757 A DE 2143757A DE 2143757 A DE2143757 A DE 2143757A DE 2143757 A1 DE2143757 A1 DE 2143757A1
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- oxidation
- oxygen
- reaction
- cycloalkane
- 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.)
- Pending
Links
- 238000007254 oxidation reaction Methods 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000003647 oxidation Effects 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 17
- 150000001924 cycloalkanes Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 4
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 4
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004914 cyclooctane Substances 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 36
- 150000001298 alcohols Chemical class 0.000 description 15
- 150000002576 ketones Chemical class 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 230000008901 benefit Effects 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Natural products O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- -1 halocarbon compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- IWMMGSGYZVJBRI-UHFFFAOYSA-N C1(CCCCCCC1)O.C1(CCCCCCC1)=O Chemical compound C1(CCCCCCC1)O.C1(CCCCCCC1)=O IWMMGSGYZVJBRI-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- 231100000987 absorbed dose Toxicity 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- 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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2143757A DE2143757A1 (de) | 1971-09-01 | 1971-09-01 | Verfahren zur herstellung von cycloalkanol und cycloalkanon durch oxydation von cycloalkan |
| GB3725172A GB1338359A (en) | 1971-09-01 | 1972-08-09 | Method of producing cycloalkanols and cycloalkanones by oxidation of cycloalkanes |
| JP47081758A JPS4935361A (cs) | 1971-09-01 | 1972-08-15 | |
| FR7230821A FR2150997A1 (cs) | 1971-09-01 | 1972-08-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2143757A DE2143757A1 (de) | 1971-09-01 | 1971-09-01 | Verfahren zur herstellung von cycloalkanol und cycloalkanon durch oxydation von cycloalkan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2143757A1 true DE2143757A1 (de) | 1973-03-08 |
Family
ID=5818361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2143757A Pending DE2143757A1 (de) | 1971-09-01 | 1971-09-01 | Verfahren zur herstellung von cycloalkanol und cycloalkanon durch oxydation von cycloalkan |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS4935361A (cs) |
| DE (1) | DE2143757A1 (cs) |
| FR (1) | FR2150997A1 (cs) |
| GB (1) | GB1338359A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5297506A (en) * | 1976-02-10 | 1977-08-16 | Japanese National Railways<Jnr> | Tare type brake system for vehicle |
-
1971
- 1971-09-01 DE DE2143757A patent/DE2143757A1/de active Pending
-
1972
- 1972-08-09 GB GB3725172A patent/GB1338359A/en not_active Expired
- 1972-08-15 JP JP47081758A patent/JPS4935361A/ja active Pending
- 1972-08-30 FR FR7230821A patent/FR2150997A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1338359A (en) | 1973-11-21 |
| FR2150997A1 (cs) | 1973-04-13 |
| JPS4935361A (cs) | 1974-04-01 |
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