DE1643255A1 - Verfahren zur Herstellung von p-Aminophenol - Google Patents
Verfahren zur Herstellung von p-AminophenolInfo
- Publication number
- DE1643255A1 DE1643255A1 DE19671643255 DE1643255A DE1643255A1 DE 1643255 A1 DE1643255 A1 DE 1643255A1 DE 19671643255 DE19671643255 DE 19671643255 DE 1643255 A DE1643255 A DE 1643255A DE 1643255 A1 DE1643255 A1 DE 1643255A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- reduction
- aminophenol
- nitrobenzene
- reaction
- 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 43
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 63
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 54
- 230000009467 reduction Effects 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 9
- 239000010970 precious metal Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010016803 Fluid overload Diseases 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 101150108228 CYLD gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000751119 Mila <angiosperm> Species 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- -1 heterogeneous Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
- 239000012855 volatile organic compound 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US470589A US3383416A (en) | 1965-07-08 | 1965-07-08 | Process for preparing aminophenol |
| DEB0095116 | 1967-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643255A1 true DE1643255A1 (de) | 1971-08-26 |
Family
ID=25968384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643255 Pending DE1643255A1 (de) | 1965-07-08 | 1967-10-24 | Verfahren zur Herstellung von p-Aminophenol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3383416A (enExample) |
| BE (1) | BE706591A (enExample) |
| CH (1) | CH494733A (enExample) |
| DE (1) | DE1643255A1 (enExample) |
| GB (1) | GB1112678A (enExample) |
| NL (1) | NL150428B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR880100281A (en) * | 1987-04-29 | 1989-01-31 | Noramco Inc | Improved hydrogenation method for preparating 4- aminophenole |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535382A (en) * | 1967-11-02 | 1970-10-20 | Cpc International Inc | Amino phenol production |
| BE757390A (fr) * | 1969-10-16 | 1971-04-13 | Howard Hall & Cy | Purification de p-aminophénol |
| BE757391A (fr) * | 1969-10-16 | 1971-04-13 | Howard Hall & Cy | Purification de p-aminophenol |
| US3715397A (en) * | 1970-04-16 | 1973-02-06 | Engelhard Min & Chem | Process for preparing para-aminophenol |
| US3935283A (en) * | 1972-06-29 | 1976-01-27 | Koppers Company, Inc. | Production of hydroquinone |
| US3937741A (en) * | 1972-06-29 | 1976-02-10 | Koppers Company, Inc. | Production of hydroquinone |
| US3917695A (en) * | 1973-02-20 | 1975-11-04 | Mallinckrodt Inc | Preparation of N-acetyl-p-aminophenol |
| US4051187A (en) * | 1975-03-05 | 1977-09-27 | Oxamine, Inc. | Method of producing aminophenol using a rhodium/carbon catalyst with synergistic quantities of rhodium, trichloride or rhodium tribromide |
| US4176138A (en) * | 1978-10-27 | 1979-11-27 | Mallinckrodt, Inc. | Process for preparing p-aminophenol in the presence of dimethyldodecylamine sulfate |
| US4256669A (en) * | 1978-11-08 | 1981-03-17 | Mallinckrodt, Inc. | Para-aminophenol derivatives |
| US4224247A (en) * | 1978-11-08 | 1980-09-23 | Mallinckrodt, Inc. | Recovery of para-aminophenol |
| US4264529A (en) * | 1980-03-24 | 1981-04-28 | Mallinckrodt, Inc. | Method for preparing p-aminophenol |
| US4440954A (en) * | 1980-06-05 | 1984-04-03 | Mallinckrodt, Inc. | Process for the purification of p-aminophenol |
| US4415753A (en) * | 1982-01-29 | 1983-11-15 | Mallinckrodt, Inc. | Process for preparing p-aminophenol and alkyl substituted p-aminophenol |
| EP0085511B1 (en) * | 1982-01-29 | 1986-03-12 | MALLINCKRODT, INC.(a Missouri corporation) | Process for preparing p-aminophenol and alkyl substituted p-aminophenol |
| US4571437A (en) * | 1982-01-29 | 1986-02-18 | Mallinckrodt, Inc. | Process for preparing p-aminophenol and alkyl substituted p-aminophenol |
| AU569344B2 (en) * | 1983-02-15 | 1988-01-28 | Mitsui Toatsu Chemicals Inc. | Production of 4-alkoxyanilines |
| JPS60115556A (ja) * | 1983-11-28 | 1985-06-22 | Mitsui Toatsu Chem Inc | ４−アルコキシアニリン類の製造方法 |
| DE3576818D1 (de) * | 1984-04-30 | 1990-05-03 | Montvale Process Co Inc | Verfahren zur kontinuierlichen herstellung von p-phenylendiamin aus nitrobenzol. |
| US4885389A (en) * | 1987-06-08 | 1989-12-05 | Industrial Technology Research Institute | Process for manufacturing p-aminophenol |
| US5312991A (en) * | 1992-06-09 | 1994-05-17 | Mallinckrodt Specialty Chemicals Company | Surfactant improvement for para-aminophenol process |
| DE69418768T2 (de) * | 1993-04-30 | 1999-10-21 | Hoechst Celanese Corp., Somerville | Verfahren zur Herstellung von N-acylierten Aminophenolen |
| US6028227A (en) * | 1999-02-12 | 2000-02-22 | Council Of Scientific & Industrial Research | Single step process for the preparation of p-aminophenol |
| EP2058050A1 (en) | 2007-11-07 | 2009-05-13 | Centre National De La Recherche Scientifique (Cnrs) | Single-step catalytic preparation of para-aminophenol |
| CN103193660B (zh) * | 2013-03-30 | 2015-03-04 | 浙江工业大学 | 一种4-烷氧基苯胺类化合物的合成方法 |
| CN109761824B (zh) * | 2019-02-13 | 2022-08-02 | 江苏扬农化工集团有限公司 | 一种催化加氢合成对氨基苯酚联产对氨基苯醚的方法 |
| CN112010765B (zh) * | 2020-09-24 | 2022-11-15 | 河北工业大学 | 一种硝基苯转移加氢制备对氨基苯酚的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB856366A (en) * | 1958-05-12 | 1960-12-14 | Ici Ltd | Process for the production of p-aminophenol from nitrobenzene |
-
1965
- 1965-07-08 US US470589A patent/US3383416A/en not_active Expired - Lifetime
-
1966
- 1966-06-28 GB GB29028/66A patent/GB1112678A/en not_active Expired
-
1967
- 1967-08-04 NL NL676710755A patent/NL150428B/xx not_active IP Right Cessation
- 1967-10-24 DE DE19671643255 patent/DE1643255A1/de active Pending
- 1967-11-02 CH CH1537567A patent/CH494733A/de not_active IP Right Cessation
- 1967-11-16 BE BE706591D patent/BE706591A/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR880100281A (en) * | 1987-04-29 | 1989-01-31 | Noramco Inc | Improved hydrogenation method for preparating 4- aminophenole |
| EP0289297B1 (en) * | 1987-04-29 | 1993-03-17 | Noramco, Inc. | Improved hydrogenation process for preparing 4-aminophenol |
Also Published As
| Publication number | Publication date |
|---|---|
| CH494733A (de) | 1970-08-15 |
| GB1112678A (en) | 1968-05-08 |
| NL6710755A (enExample) | 1969-02-06 |
| NL150428B (nl) | 1976-08-16 |
| BE706591A (fr) | 1968-04-01 |
| US3383416A (en) | 1968-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EGA | New person/name/address of the applicant |