GB620114A - Manufacture of ª‡,ª‡-di-(amino-phenyl)-ª‰,ª‰,ª‰-trichlorethanes - Google Patents
Manufacture of ª‡,ª‡-di-(amino-phenyl)-ª‰,ª‰,ª‰-trichlorethanesInfo
- Publication number
- GB620114A GB620114A GB1487747A GB1487747A GB620114A GB 620114 A GB620114 A GB 620114A GB 1487747 A GB1487747 A GB 1487747A GB 1487747 A GB1487747 A GB 1487747A GB 620114 A GB620114 A GB 620114A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrophenyl
- trichloroethane
- aminophenyl
- mixed
- trichlorethane
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- -1 m - nitrophenyl Chemical group 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
a ,a -Di-(aminophenyl)-b ,b ,b -trichloroethanes are produced by the neutral or slightly acid reduction of the corresponding nitro compounds. In examples, a ,a -di-(p-nitrophenyl)-b ,b ,b -trichloroethane reduced by (1) stannous chloride in glacial acetic acid saturated with hydrogen chloride (2) iron and acetic acid and (3) and (4) catalytic hydrogenation with mixed Raney nickel and 5 per cent platinised charcoal in mixed ethyl acetate and alcohol, or with platinic oxide in mixed glacial acetic and concentrated hydrochloric acid, yields a ,a -di-(p-aminophenyl)-b ,b ,b - trichloroethane; and likewise (5) a - (p - nitrophenyl) - a - (m - nitrophenyl) - b ,b ,b - trichloroethane reduced according to method (1) yields a - (p - aminophenyl) - a - (m-aminophenyl)-b ,b ,b -trichloroethane. Sulphates, oxalates and dihydrochlorides of the two bases are described and a further method of reduction, viz. electrochemical instanced. The nitro-compounds used as starting materials are obtained by the nitration of a ,a -diphenyl-b ,b ,b -trichlorethane with e.g. fuming nitric, mixed sulphuric and nitric or glacial acetic and nitric acids, or acetyl nitrate, a ,a -di-(p-nitrophenyl) - b ,b ,b - trichlorethane being separated from a - (p - nitrophenyl) - a - (m - nitrophenyl) - b ,b ,b -trichlorethane by fractional crystallization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1487747A GB620114A (en) | 1946-07-03 | 1946-07-03 | Manufacture of ª‡,ª‡-di-(amino-phenyl)-ª‰,ª‰,ª‰-trichlorethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1487747A GB620114A (en) | 1946-07-03 | 1946-07-03 | Manufacture of ª‡,ª‡-di-(amino-phenyl)-ª‰,ª‰,ª‰-trichlorethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB620114A true GB620114A (en) | 1949-03-18 |
Family
ID=10049090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1487747A Expired GB620114A (en) | 1946-07-03 | 1946-07-03 | Manufacture of ª‡,ª‡-di-(amino-phenyl)-ª‰,ª‰,ª‰-trichlorethanes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB620114A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4758380A (en) * | 1986-10-29 | 1988-07-19 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Substituted 1,1,1-triaryl-2,2,2-trifluoroethanes and processes for their synthesis |
| US4863640A (en) * | 1986-05-27 | 1989-09-05 | United Technologies Corporation | Monomers for high temperature fluorinated polyimides |
-
1946
- 1946-07-03 GB GB1487747A patent/GB620114A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863640A (en) * | 1986-05-27 | 1989-09-05 | United Technologies Corporation | Monomers for high temperature fluorinated polyimides |
| US4758380A (en) * | 1986-10-29 | 1988-07-19 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Substituted 1,1,1-triaryl-2,2,2-trifluoroethanes and processes for their synthesis |
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