DE2429781C2 - Verfahren zur Herstellung von N,N-Bis-(2-cyanoäthyl)-amino-phenolen - Google Patents
Verfahren zur Herstellung von N,N-Bis-(2-cyanoäthyl)-amino-phenolenInfo
- Publication number
- DE2429781C2 DE2429781C2 DE2429781A DE2429781A DE2429781C2 DE 2429781 C2 DE2429781 C2 DE 2429781C2 DE 2429781 A DE2429781 A DE 2429781A DE 2429781 A DE2429781 A DE 2429781A DE 2429781 C2 DE2429781 C2 DE 2429781C2
- Authority
- DE
- Germany
- Prior art keywords
- aminophenol
- acetic acid
- cyanoethyl
- bis
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- HBZUTHNXOTWAFZ-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-2-hydroxyanilino]propanenitrile Chemical class OC1=CC=CC=C1N(CCC#N)CCC#N HBZUTHNXOTWAFZ-UHFFFAOYSA-N 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 22
- 229960000583 acetic acid Drugs 0.000 description 14
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 12
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940018563 3-aminophenol Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007278 cyanoethylation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US372315A US3890368A (en) | 1973-06-21 | 1973-06-21 | Method for N,N-dicyanoethylating aminophenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2429781A1 DE2429781A1 (de) | 1975-01-23 |
| DE2429781C2 true DE2429781C2 (de) | 1983-10-27 |
Family
ID=23467635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2429781A Expired DE2429781C2 (de) | 1973-06-21 | 1974-06-21 | Verfahren zur Herstellung von N,N-Bis-(2-cyanoäthyl)-amino-phenolen |
Country Status (10)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519002C3 (de) * | 1975-04-29 | 1978-09-21 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von l-(2-Cyanathylamino)-3-acylaminobenzolen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809983A (en) * | 1956-03-12 | 1957-10-15 | Monsanto Chemicals | Hydroxyanilinopropionitriles |
| US3743668A (en) * | 1971-06-01 | 1973-07-03 | Mallinckrodt Chemical Works | Cyanoethylation of aminophenols |
-
1973
- 1973-06-21 US US372315A patent/US3890368A/en not_active Expired - Lifetime
-
1974
- 1974-06-17 NL NL7408084A patent/NL7408084A/xx not_active Application Discontinuation
- 1974-06-18 GB GB2701374A patent/GB1405243A/en not_active Expired
- 1974-06-20 BE BE145700A patent/BE816646A/xx not_active IP Right Cessation
- 1974-06-20 IT IT51640/74A patent/IT1016121B/it active
- 1974-06-20 CH CH844874A patent/CH587232A5/xx not_active IP Right Cessation
- 1974-06-20 SE SE7408179A patent/SE411751B/xx unknown
- 1974-06-20 FR FR7421524A patent/FR2234279B1/fr not_active Expired
- 1974-06-21 JP JP49070342A patent/JPS50157324A/ja active Pending
- 1974-06-21 DE DE2429781A patent/DE2429781C2/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2429781A1 (de) | 1975-01-23 |
| JPS50157324A (enrdf_load_stackoverflow) | 1975-12-19 |
| IT1016121B (it) | 1977-05-30 |
| SE411751B (sv) | 1980-02-04 |
| NL7408084A (enrdf_load_stackoverflow) | 1974-12-24 |
| US3890368A (en) | 1975-06-17 |
| GB1405243A (en) | 1975-09-10 |
| SE7408179L (enrdf_load_stackoverflow) | 1974-12-23 |
| FR2234279B1 (enrdf_load_stackoverflow) | 1978-01-13 |
| CH587232A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| BE816646A (fr) | 1974-12-20 |
| FR2234279A1 (enrdf_load_stackoverflow) | 1975-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C121/43 |
|
| 8181 | Inventor (new situation) |
Free format text: JAMIESON, NORMAN C., ST. LOUIS, MO., US |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |