DE2103548A1 - Verfahren zur Reinigung von rohem p Aminophenol - Google Patents
Verfahren zur Reinigung von rohem p AminophenolInfo
- Publication number
- DE2103548A1 DE2103548A1 DE19712103548 DE2103548A DE2103548A1 DE 2103548 A1 DE2103548 A1 DE 2103548A1 DE 19712103548 DE19712103548 DE 19712103548 DE 2103548 A DE2103548 A DE 2103548A DE 2103548 A1 DE2103548 A1 DE 2103548A1
- Authority
- DE
- Germany
- Prior art keywords
- aminophenol
- extracted
- solvents
- solvent
- crude
- 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
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 23
- 238000000746 purification Methods 0.000 title description 5
- 239000002904 solvent Substances 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 229960003750 ethyl chloride Drugs 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- -1 1,1,2-trichloroethyl Chemical group 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000008364 bulk solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy 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 |
|---|---|---|---|
| GB4021/70A GB1291642A (en) | 1970-01-28 | 1970-01-28 | PURIFICATION OF p-AMINOPHENOL |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2103548A1 true DE2103548A1 (de) | 1971-08-05 |
Family
ID=9769246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712103548 Pending DE2103548A1 (de) | 1970-01-28 | 1971-01-26 | Verfahren zur Reinigung von rohem p Aminophenol |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3845129A (OSRAM) |
| JP (1) | JPS5921860B1 (OSRAM) |
| BE (1) | BE761901A (OSRAM) |
| CA (1) | CA970784A (OSRAM) |
| CH (1) | CH539605A (OSRAM) |
| DE (1) | DE2103548A1 (OSRAM) |
| FR (1) | FR2076983A5 (OSRAM) |
| GB (1) | GB1291642A (OSRAM) |
| NL (1) | NL7101088A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0289298A3 (en) * | 1987-04-29 | 1989-10-11 | Noramco, Inc. | Process for purifying crude 4-aminophenol |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3876703A (en) * | 1973-06-05 | 1975-04-08 | Cpc International Inc | Purification of p-aminophenol |
| US4139562A (en) * | 1978-03-13 | 1979-02-13 | Mitsui Toatsu Chemicals, Inc. | Process for purifying crude p-aminophenol |
| US4440954A (en) * | 1980-06-05 | 1984-04-03 | Mallinckrodt, Inc. | Process for the purification of p-aminophenol |
| US4307249A (en) * | 1981-01-07 | 1981-12-22 | Mallinckrodt, Inc. | Process for the selective preparation of p-aminophenol from nitrobenzene |
| US4670589A (en) * | 1982-11-04 | 1987-06-02 | Monsanto Company | Preparation of N-acetyl-p-aminophenol |
| US4565890A (en) * | 1983-10-27 | 1986-01-21 | Mallinckrodt, Inc. | Process for the preparation of N-acetyl-P-aminophenol |
| US5155269A (en) | 1984-01-30 | 1992-10-13 | Mallinckrodt | Purification of p-aminophenol compositions and direct conversion to N-acetyl-p-aminophenol |
| IN161689B (OSRAM) * | 1984-06-18 | 1988-01-16 | Sumitomo Chemical Co | |
| US4990671A (en) * | 1988-04-18 | 1991-02-05 | Mallinckrodt, Inc. | Method for making aminophenols and their amide derivatives |
| ES2407804B1 (es) * | 2013-04-10 | 2013-12-03 | Pfisterer Upresa, S.A. | Mensula para catenaria |
| CN115521014A (zh) * | 2022-10-28 | 2022-12-27 | 辽宁世星药化有限公司 | 硝基苯催化加氢生产对氨基苯酚产生废水的处理方法 |
-
1970
- 1970-01-28 GB GB4021/70A patent/GB1291642A/en not_active Expired
- 1970-12-29 US US00102512A patent/US3845129A/en not_active Expired - Lifetime
- 1970-12-29 CA CA101,556A patent/CA970784A/en not_active Expired
-
1971
- 1971-01-21 JP JP711955A patent/JPS5921860B1/ja active Granted
- 1971-01-22 BE BE761901A patent/BE761901A/xx unknown
- 1971-01-26 DE DE19712103548 patent/DE2103548A1/de active Pending
- 1971-01-26 FR FR7102465A patent/FR2076983A5/fr not_active Expired
- 1971-01-27 NL NL7101088A patent/NL7101088A/xx unknown
- 1971-01-28 CH CH124871A patent/CH539605A/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0289298A3 (en) * | 1987-04-29 | 1989-10-11 | Noramco, Inc. | Process for purifying crude 4-aminophenol |
| AU611429B2 (en) * | 1987-04-29 | 1991-06-13 | Noramco, Inc. | Process for purifying crude 4-aminophenol |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7101088A (OSRAM) | 1971-07-30 |
| US3845129A (en) | 1974-10-29 |
| GB1291642A (en) | 1972-10-04 |
| FR2076983A5 (OSRAM) | 1971-10-15 |
| CH539605A (de) | 1973-07-31 |
| JPS5921860B1 (OSRAM) | 1984-05-22 |
| BE761901A (fr) | 1971-07-22 |
| CA970784A (en) | 1975-07-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |