SU626688A3 - Способ получени дифениламинов - Google Patents
Способ получени дифениламиновInfo
- Publication number
- SU626688A3 SU626688A3 SU762403404A SU2403404A SU626688A3 SU 626688 A3 SU626688 A3 SU 626688A3 SU 762403404 A SU762403404 A SU 762403404A SU 2403404 A SU2403404 A SU 2403404A SU 626688 A3 SU626688 A3 SU 626688A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitro
- methyl
- hydrogen
- radicals
- bromine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000002431 hydrogen Chemical group 0.000 claims 14
- 150000003254 radicals Chemical class 0.000 claims 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 13
- 239000000047 product Substances 0.000 claims 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 6
- 239000012312 sodium hydride Substances 0.000 claims 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- 238000004587 chromatography analysis Methods 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- DQXUPWGUKXGTBG-UHFFFAOYSA-N n-phenyl-n-(trifluoromethyl)aniline Chemical compound C=1C=CC=CC=1N(C(F)(F)F)C1=CC=CC=C1 DQXUPWGUKXGTBG-UHFFFAOYSA-N 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- -1 xpor Substances 0.000 claims 4
- HQROXDLWVGFPDE-UHFFFAOYSA-N 1-chloro-4-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HQROXDLWVGFPDE-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000000741 silica gel Substances 0.000 claims 3
- 229910002027 silica gel Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 239000010410 layer Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 238000005303 weighing Methods 0.000 claims 2
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 claims 1
- WHNAMGUAXHGCHH-UHFFFAOYSA-N 1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1 WHNAMGUAXHGCHH-UHFFFAOYSA-N 0.000 claims 1
- XIIWZUPVDADJHT-UHFFFAOYSA-N 2,4,6-trichloro-n-ethylaniline Chemical compound CCNC1=C(Cl)C=C(Cl)C=C1Cl XIIWZUPVDADJHT-UHFFFAOYSA-N 0.000 claims 1
- QHXFGOIOVYTMHQ-UHFFFAOYSA-N 2,4,6-trichloro-n-methylaniline Chemical compound CNC1=C(Cl)C=C(Cl)C=C1Cl QHXFGOIOVYTMHQ-UHFFFAOYSA-N 0.000 claims 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- 240000007313 Tilia cordata Species 0.000 claims 1
- 244000250129 Trigonella foenum graecum Species 0.000 claims 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ZUGPRXZCSHTXTE-UHFFFAOYSA-N diphenyl sulfate Chemical compound C=1C=CC=CC=1OS(=O)(=O)OC1=CC=CC=C1 ZUGPRXZCSHTXTE-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000004533 oil dispersion Substances 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70602476A | 1976-07-21 | 1976-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU626688A3 true SU626688A3 (ru) | 1978-09-30 |
Family
ID=24835902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762403404A SU626688A3 (ru) | 1976-07-21 | 1976-09-24 | Способ получени дифениламинов |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS601299B2 (OSRAM) |
| AT (1) | AT343623B (OSRAM) |
| BE (1) | BE846206A (OSRAM) |
| BG (1) | BG28844A3 (OSRAM) |
| CA (1) | CA1090821A (OSRAM) |
| CH (1) | CH599923A5 (OSRAM) |
| CS (1) | CS186249B2 (OSRAM) |
| DD (1) | DD127400A5 (OSRAM) |
| DE (1) | DE2640461A1 (OSRAM) |
| DK (1) | DK430976A (OSRAM) |
| ES (1) | ES451904A1 (OSRAM) |
| FI (1) | FI762498A7 (OSRAM) |
| FR (1) | FR2359117A1 (OSRAM) |
| GB (1) | GB1549411A (OSRAM) |
| GR (1) | GR61291B (OSRAM) |
| HU (1) | HU175077B (OSRAM) |
| IE (1) | IE43932B1 (OSRAM) |
| IL (1) | IL50256A (OSRAM) |
| IN (1) | IN142337B (OSRAM) |
| IT (1) | IT1065257B (OSRAM) |
| MX (1) | MX4393E (OSRAM) |
| NL (1) | NL7610496A (OSRAM) |
| NO (1) | NO143024C (OSRAM) |
| PL (1) | PL106778B1 (OSRAM) |
| PT (1) | PT65678B (OSRAM) |
| RO (1) | RO70077A (OSRAM) |
| SE (1) | SE435056B (OSRAM) |
| SU (1) | SU626688A3 (OSRAM) |
| YU (1) | YU214776A (OSRAM) |
| ZA (1) | ZA764841B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5774611A (en) * | 1980-10-28 | 1982-05-10 | Mitsubishi Precision Co Ltd | Attitude reference apparatus employing single axis platform |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212825A (en) * | 1937-12-31 | 1940-08-27 | Du Pont | Nitro-trifluoromethyl-aryl amines and process for making them |
| BE577941A (OSRAM) * | 1958-04-22 |
-
1976
- 1976-08-09 IE IE1760/76A patent/IE43932B1/en unknown
- 1976-08-10 GB GB33174/76A patent/GB1549411A/en not_active Expired
- 1976-08-10 CA CA258,795A patent/CA1090821A/en not_active Expired
- 1976-08-11 ZA ZA00764841A patent/ZA764841B/xx unknown
- 1976-08-11 GR GR51459A patent/GR61291B/el unknown
- 1976-08-12 IN IN1467/CAL/1976A patent/IN142337B/en unknown
- 1976-08-12 IL IL7650256A patent/IL50256A/xx unknown
- 1976-08-12 HU HU76EI691A patent/HU175077B/hu unknown
- 1976-08-25 IT IT26533/76A patent/IT1065257B/it active
- 1976-08-30 MX MX764868U patent/MX4393E/es unknown
- 1976-08-30 SE SE7609587A patent/SE435056B/xx unknown
- 1976-08-31 FI FI762498A patent/FI762498A7/fi not_active Application Discontinuation
- 1976-09-01 YU YU02147/76A patent/YU214776A/xx unknown
- 1976-09-07 AT AT664076A patent/AT343623B/de not_active IP Right Cessation
- 1976-09-08 DE DE19762640461 patent/DE2640461A1/de not_active Withdrawn
- 1976-09-09 CH CH1148176A patent/CH599923A5/xx not_active IP Right Cessation
- 1976-09-10 DD DD194749A patent/DD127400A5/xx unknown
- 1976-09-15 BE BE1007627A patent/BE846206A/xx not_active IP Right Cessation
- 1976-09-15 FR FR7627686A patent/FR2359117A1/fr active Granted
- 1976-09-16 CS CS7600006026A patent/CS186249B2/cs unknown
- 1976-09-17 RO RO7687563A patent/RO70077A/ro unknown
- 1976-09-20 NO NO763217A patent/NO143024C/no unknown
- 1976-09-21 NL NL7610496A patent/NL7610496A/xx active Search and Examination
- 1976-09-24 DK DK430976A patent/DK430976A/da not_active Application Discontinuation
- 1976-09-24 SU SU762403404A patent/SU626688A3/ru active
- 1976-09-27 ES ES451904A patent/ES451904A1/es not_active Expired
- 1976-10-04 PT PT65678A patent/PT65678B/pt unknown
- 1976-10-26 PL PL1976193263A patent/PL106778B1/pl unknown
- 1976-10-28 BG BG034547A patent/BG28844A3/xx unknown
- 1976-11-18 JP JP51139414A patent/JPS601299B2/ja not_active Expired
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