CH494733A - Verfahren zur Herstellung von p-Aminophenol - Google Patents
Verfahren zur Herstellung von p-AminophenolInfo
- Publication number
- CH494733A CH494733A CH1537567A CH1537567A CH494733A CH 494733 A CH494733 A CH 494733A CH 1537567 A CH1537567 A CH 1537567A CH 1537567 A CH1537567 A CH 1537567A CH 494733 A CH494733 A CH 494733A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrobenzene
- catalyst
- aminophenol
- organic layer
- reduction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000008569 process Effects 0.000 title claims description 17
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 145
- 239000003054 catalyst Substances 0.000 claims abstract description 69
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims abstract description 66
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000725 suspension Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 11
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 230000009467 reduction Effects 0.000 claims description 36
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 239000010410 layer Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000004064 recycling Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000013049 sediment Substances 0.000 abstract description 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 239000012071 phase Substances 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 24
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PVBLJPCMWKGTOH-UHFFFAOYSA-N 1-aminocyclohexan-1-ol Chemical compound NC1(O)CCCCC1 PVBLJPCMWKGTOH-UHFFFAOYSA-N 0.000 description 1
- 206010016803 Fluid overload Diseases 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RXHDXDIEHWVFOC-UHFFFAOYSA-M ethyl-dimethyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC RXHDXDIEHWVFOC-UHFFFAOYSA-M 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 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 |
|---|---|
| CH494733A true CH494733A (de) | 1970-08-15 |
Family
ID=25968384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1537567A CH494733A (de) | 1965-07-08 | 1967-11-02 | Verfahren zur Herstellung von p-Aminophenol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3383416A (cg-RX-API-DMAC7.html) |
| BE (1) | BE706591A (cg-RX-API-DMAC7.html) |
| CH (1) | CH494733A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1643255A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1112678A (cg-RX-API-DMAC7.html) |
| NL (1) | NL150428B (cg-RX-API-DMAC7.html) |
Families Citing this family (28)
| 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 |
| US4224247A (en) * | 1978-11-08 | 1980-09-23 | Mallinckrodt, Inc. | Recovery of para-aminophenol |
| US4256669A (en) * | 1978-11-08 | 1981-03-17 | Mallinckrodt, Inc. | Para-aminophenol derivatives |
| 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 |
| EP0085511B1 (en) * | 1982-01-29 | 1986-03-12 | MALLINCKRODT, INC.(a Missouri corporation) | Process for preparing p-aminophenol and alkyl substituted p-aminophenol |
| US4415753A (en) * | 1982-01-29 | 1983-11-15 | Mallinckrodt, Inc. | 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 |
| EP0160562B1 (en) * | 1984-04-30 | 1990-03-28 | Montvale Process Company Incorporated | Process for the continuous preparation of p-phenylenediamine from a nitrobenzene feedstock |
| JP2591786B2 (ja) * | 1987-04-29 | 1997-03-19 | ノランコ・インコーポレーテツド | ４‐アミノフエノール製造用の改良水素化方法 |
| 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 |
| EP0622354B1 (en) * | 1993-04-30 | 1999-06-02 | Hoechst Celanese Corporation | Improved process for preparing acyl aminophenols |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| US3383416A (en) | 1968-05-14 |
| BE706591A (fr) | 1968-04-01 |
| NL6710755A (cg-RX-API-DMAC7.html) | 1969-02-06 |
| GB1112678A (en) | 1968-05-08 |
| DE1643255A1 (de) | 1971-08-26 |
| NL150428B (nl) | 1976-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |