DE2148961A1 - Verfahren zur Herstellung von zwei- oder mehrkernigen heterocyclischen Verbindungen - Google Patents
Verfahren zur Herstellung von zwei- oder mehrkernigen heterocyclischen VerbindungenInfo
- Publication number
- DE2148961A1 DE2148961A1 DE19712148961 DE2148961A DE2148961A1 DE 2148961 A1 DE2148961 A1 DE 2148961A1 DE 19712148961 DE19712148961 DE 19712148961 DE 2148961 A DE2148961 A DE 2148961A DE 2148961 A1 DE2148961 A1 DE 2148961A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- ethylaniline
- mixture
- aromatic compound
- eeaktion
- 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
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 7
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000001491 aromatic compounds Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 alkyl radical Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 238000005201 scrubbing Methods 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 34
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 17
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 9
- KURPPWHPIYBYBS-UHFFFAOYSA-N 2-ethenylaniline Chemical compound NC1=CC=CC=C1C=C KURPPWHPIYBYBS-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
- 240000000736 Amomum maximum Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Natural products C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3035770 | 1970-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2148961A1 true DE2148961A1 (de) | 1972-04-06 |
Family
ID=11229593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712148961 Pending DE2148961A1 (de) | 1970-09-30 | 1971-09-30 | Verfahren zur Herstellung von zwei- oder mehrkernigen heterocyclischen Verbindungen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3843680A (enExample) |
| AT (1) | AT311331B (enExample) |
| BE (1) | BE773163A (enExample) |
| CA (1) | CA935819A (enExample) |
| CH (1) | CH551443A (enExample) |
| CS (1) | CS189574B2 (enExample) |
| DE (1) | DE2148961A1 (enExample) |
| ES (1) | ES395872A1 (enExample) |
| FR (1) | FR2112991A5 (enExample) |
| GB (1) | GB1332264A (enExample) |
| HU (1) | HU163930B (enExample) |
| LU (1) | LU63979A1 (enExample) |
| NL (1) | NL7113400A (enExample) |
| NO (1) | NO139171C (enExample) |
| SE (1) | SE390732B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2441439A1 (de) * | 1973-09-12 | 1975-03-13 | Lonza Ag | Verfahren zur herstellung von indol |
| US4703126A (en) * | 1983-03-23 | 1987-10-27 | Lonza Ltd. | Process for the production of 7-ethyl indole |
| WO1996032391A1 (de) * | 1995-04-11 | 1996-10-17 | Lonza Ag | Verfahren zur herstellung von azaindolen mit aktiviertem kupferchromit katalysator durch katalytische dehydrocyclisierung von alkyl-pyridylaminen (pyridopyridinen) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7342796B2 (en) * | 2005-06-03 | 2008-03-11 | Southco, Inc. | Captive shoulder nut assembly |
-
1971
- 1971-09-28 BE BE773163A patent/BE773163A/xx unknown
- 1971-09-28 ES ES395872A patent/ES395872A1/es not_active Expired
- 1971-09-28 CA CA123931A patent/CA935819A/en not_active Expired
- 1971-09-28 NO NO3573/71A patent/NO139171C/no unknown
- 1971-09-29 HU HUSA2252A patent/HU163930B/hu unknown
- 1971-09-29 FR FR7135027A patent/FR2112991A5/fr not_active Expired
- 1971-09-29 LU LU63979D patent/LU63979A1/xx unknown
- 1971-09-30 DE DE19712148961 patent/DE2148961A1/de active Pending
- 1971-09-30 GB GB4567571A patent/GB1332264A/en not_active Expired
- 1971-09-30 CH CH1419971A patent/CH551443A/fr not_active IP Right Cessation
- 1971-09-30 SE SE7112423A patent/SE390732B/xx unknown
- 1971-09-30 AT AT846371A patent/AT311331B/de not_active IP Right Cessation
- 1971-09-30 CS CS716931A patent/CS189574B2/cs unknown
- 1971-09-30 US US00185075A patent/US3843680A/en not_active Expired - Lifetime
- 1971-09-30 NL NL7113400A patent/NL7113400A/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2441439A1 (de) * | 1973-09-12 | 1975-03-13 | Lonza Ag | Verfahren zur herstellung von indol |
| US4703126A (en) * | 1983-03-23 | 1987-10-27 | Lonza Ltd. | Process for the production of 7-ethyl indole |
| WO1996032391A1 (de) * | 1995-04-11 | 1996-10-17 | Lonza Ag | Verfahren zur herstellung von azaindolen mit aktiviertem kupferchromit katalysator durch katalytische dehydrocyclisierung von alkyl-pyridylaminen (pyridopyridinen) |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7113400A (enExample) | 1972-04-05 |
| CS189574B2 (en) | 1979-04-30 |
| ES395872A1 (es) | 1974-10-16 |
| HU163930B (enExample) | 1973-11-28 |
| AT311331B (de) | 1973-11-12 |
| SE390732B (sv) | 1977-01-17 |
| LU63979A1 (enExample) | 1972-03-01 |
| US3843680A (en) | 1974-10-22 |
| NO139171C (no) | 1979-01-17 |
| NO139171B (no) | 1978-10-09 |
| GB1332264A (en) | 1973-10-03 |
| FR2112991A5 (enExample) | 1972-06-23 |
| CH551443A (fr) | 1974-07-15 |
| BE773163A (fr) | 1972-01-17 |
| CA935819A (en) | 1973-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OHW | Rejection |