DE2064279C3 - Verfahren zur Herstellung von durch Sauerstoff enthaltende Gruppen substituierte Acenaphtene - Google Patents
Verfahren zur Herstellung von durch Sauerstoff enthaltende Gruppen substituierte AcenaphteneInfo
- Publication number
- DE2064279C3 DE2064279C3 DE19702064279 DE2064279A DE2064279C3 DE 2064279 C3 DE2064279 C3 DE 2064279C3 DE 19702064279 DE19702064279 DE 19702064279 DE 2064279 A DE2064279 A DE 2064279A DE 2064279 C3 DE2064279 C3 DE 2064279C3
- Authority
- DE
- Germany
- Prior art keywords
- oxygen
- rhodium
- acenaphtenes
- substituted
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 4
- 239000001301 oxygen Substances 0.000 title description 4
- 229910052760 oxygen Inorganic materials 0.000 title description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 8
- CXOYJCOONOHMJI-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-4-carbaldehyde Chemical compound C1=CC2=CC(C=O)=CC(CC3)=C2C3=C1 CXOYJCOONOHMJI-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QRWQMHFTUWLXRB-UHFFFAOYSA-N OCC=1C=C2C=CC=C3CCC(C=1)=C32 Chemical compound OCC=1C=C2C=CC=C3CCC(C=1)=C32 QRWQMHFTUWLXRB-UHFFFAOYSA-N 0.000 description 5
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VJMHQCJVHWWMHZ-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-1-carbaldehyde Chemical compound C1=CC(C(C=O)C2)=C3C2=CC=CC3=C1 VJMHQCJVHWWMHZ-UHFFFAOYSA-N 0.000 description 1
- AJIHSYXGFHJHGS-UHFFFAOYSA-N 1-methyl-2H-acenaphthylen-1-amine Chemical compound CC1(N)Cc2cccc3cccc1c23 AJIHSYXGFHJHGS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000001239 acenaphthenes Chemical class 0.000 description 1
- AKZTWYIBFDPJLE-UHFFFAOYSA-N acenaphthylene-4-carbaldehyde Chemical group C1=CC2=CC(C=O)=CC(C=C3)=C2C3=C1 AKZTWYIBFDPJLE-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- GCPXMJHSNVMWNM-UHFFFAOYSA-N arsenous acid Chemical class O[As](O)O GCPXMJHSNVMWNM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- ADGFUTSPEKVFKD-UHFFFAOYSA-N carbonyl dichloride;rhodium Chemical compound [Rh].ClC(Cl)=O ADGFUTSPEKVFKD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- -1 fatty acid salts Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702064279 DE2064279C3 (de) | 1970-12-29 | 1970-12-29 | Verfahren zur Herstellung von durch Sauerstoff enthaltende Gruppen substituierte Acenaphtene |
| CH1782071A CH562184A5 (enrdf_load_stackoverflow) | 1970-12-29 | 1971-12-07 | |
| FR7145899A FR2120816A5 (enrdf_load_stackoverflow) | 1970-12-29 | 1971-12-21 | |
| GB5991071A GB1363929A (en) | 1970-12-29 | 1971-12-23 | Acenaphtenes bearing groups containing oxygen as substitu ents |
| NL7117828A NL7117828A (enrdf_load_stackoverflow) | 1970-12-29 | 1971-12-24 | |
| AT1116971A AT307395B (de) | 1970-12-29 | 1971-12-28 | Verfahren zur Herstellung des neuen 7-Formylacenaphthens |
| CA131,336A CA978993A (en) | 1970-12-29 | 1971-12-29 | Acenaphthenes bearing groups containing oxygen as substituents |
| BE777461A BE777461A (fr) | 1970-12-29 | 1971-12-29 | Acenaphtenes substitues par des groupes oxygenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702064279 DE2064279C3 (de) | 1970-12-29 | 1970-12-29 | Verfahren zur Herstellung von durch Sauerstoff enthaltende Gruppen substituierte Acenaphtene |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2064279A1 DE2064279A1 (de) | 1972-07-06 |
| DE2064279B2 DE2064279B2 (de) | 1974-05-02 |
| DE2064279C3 true DE2064279C3 (de) | 1975-01-16 |
Family
ID=5792468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702064279 Expired DE2064279C3 (de) | 1970-12-29 | 1970-12-29 | Verfahren zur Herstellung von durch Sauerstoff enthaltende Gruppen substituierte Acenaphtene |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT307395B (enrdf_load_stackoverflow) |
| BE (1) | BE777461A (enrdf_load_stackoverflow) |
| CA (1) | CA978993A (enrdf_load_stackoverflow) |
| CH (1) | CH562184A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2064279C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2120816A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1363929A (enrdf_load_stackoverflow) |
| NL (1) | NL7117828A (enrdf_load_stackoverflow) |
-
1970
- 1970-12-29 DE DE19702064279 patent/DE2064279C3/de not_active Expired
-
1971
- 1971-12-07 CH CH1782071A patent/CH562184A5/xx not_active IP Right Cessation
- 1971-12-21 FR FR7145899A patent/FR2120816A5/fr not_active Expired
- 1971-12-23 GB GB5991071A patent/GB1363929A/en not_active Expired
- 1971-12-24 NL NL7117828A patent/NL7117828A/xx unknown
- 1971-12-28 AT AT1116971A patent/AT307395B/de not_active IP Right Cessation
- 1971-12-29 CA CA131,336A patent/CA978993A/en not_active Expired
- 1971-12-29 BE BE777461A patent/BE777461A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2064279A1 (de) | 1972-07-06 |
| CH562184A5 (enrdf_load_stackoverflow) | 1975-05-30 |
| NL7117828A (enrdf_load_stackoverflow) | 1972-07-03 |
| FR2120816A5 (enrdf_load_stackoverflow) | 1972-08-18 |
| DE2064279B2 (de) | 1974-05-02 |
| BE777461A (fr) | 1972-06-29 |
| AT307395B (de) | 1973-05-25 |
| CA978993A (en) | 1975-12-02 |
| GB1363929A (en) | 1974-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |