CN115521014A - Method for treating wastewater generated in production of p-aminophenol by catalytic hydrogenation of nitrobenzene - Google Patents
Method for treating wastewater generated in production of p-aminophenol by catalytic hydrogenation of nitrobenzene Download PDFInfo
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- CN115521014A CN115521014A CN202211330708.4A CN202211330708A CN115521014A CN 115521014 A CN115521014 A CN 115521014A CN 202211330708 A CN202211330708 A CN 202211330708A CN 115521014 A CN115521014 A CN 115521014A
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- wastewater
- aminophenol
- nitrobenzene
- catalytic hydrogenation
- production
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- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000002351 wastewater Substances 0.000 title claims abstract description 52
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000001704 evaporation Methods 0.000 claims abstract description 25
- 230000008020 evaporation Effects 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 13
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 8
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012528 membrane Substances 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims abstract description 4
- 239000013078 crystal Substances 0.000 claims abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 239000010842 industrial wastewater Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000004065 wastewater treatment Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 1
- 238000003860 storage Methods 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005086 pumping Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 238000001228 spectrum Methods 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 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 238000006665 Bamberger reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F9/00—Multistage treatment of water, waste water or sewage
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
-
- 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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/048—Purification of waste water by evaporation
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/26—Treatment of water, waste water, or sewage by extraction
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/283—Treatment of water, waste water, or sewage by sorption using coal, charred products, or inorganic mixtures containing them
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/66—Treatment of water, waste water, or sewage by neutralisation; pH adjustment
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/72—Treatment of water, waste water, or sewage by oxidation
- C02F1/722—Oxidation by peroxides
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
- C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
Abstract
The invention relates to the field of industrial wastewater treatment, in particular to a method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene; adding toluene into the wastewater, sending the extract to a rectification system, carrying out membrane treatment on the extracted wastewater, adding sulfuric acid, adjusting the pH value to 4-5, then entering an evaporator, carrying out negative pressure evaporation, condensing steam, carrying out oxidation treatment, adding activated carbon, filtering, enabling the filtered water to enter a nitrobenzene catalytic hydrogenation reactor for reuse, cooling and crystallizing the residual solution after negative pressure evaporation, drying the filtered crystals to obtain a product ammonium sulfate, adding ammonia gas into filtrate for neutralization, carrying out filtration and separation, drying the filtered p-aminophenol, and returning the filtrate to the evaporator in the third step; according to the method, the p-aminophenol and the ammonium sulfate are respectively recovered after the p-aminophenol production wastewater is treated, and the treated water can be recycled and applied to the preparation process of the p-aminophenol, so that zero discharge of the wastewater is realized.
Description
Technical Field
The invention relates to the field of industrial wastewater treatment, in particular to a method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene.
Background
P-aminophenol is an organic intermediate with a wide range of applications. The method is mainly used for producing paracetamol, dye, rubber antioxidant, photographic developer, petroleum additive and the like, and has wide application; in the production methods of a plurality of para-aminophenols, the nitrobenzene catalytic hydrogenation method has the advantages of cheap and easily obtained raw materials, low production cost, less working procedures, high product yield and good quality; the existing industrial production mainly adopts a p-nitrophenol hydrogenation method; the nitrobenzene hydrogenation process comprises the following steps: the method comprises the steps of firstly, carrying out hydrogenation reduction on nitrobenzene serving as a raw material in a Pt/c catalyst to produce intermediate phenylhydroxylamine, then carrying out Bamberger rearrangement reaction on the phenylhydroxylamine in an acid solution to generate PAP (p-aminophenol), adjusting the pH value of the solution to 6.8-7.0 through neutralization, crystallizing the p-aminophenol to separate out most of the p-aminophenol, and further containing substances such as p-aminophenol, aniline, ammonium sulfate and an emulsifier in wastewater, wherein the substances cannot be directly discharged and need to be treated.
Disclosure of Invention
The invention aims to solve the problems, and provides a method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene.
The invention solves the problems and adopts the technical scheme that:
a method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene comprises the following steps:
step one, adding toluene into the wastewater, extracting aniline in the wastewater, standing for 60min, and sending an extract to a rectification system to recover the toluene and aniline in the extract;
step two, the wastewater obtained after extraction in the step one is subjected to membrane treatment to remove an emulsifier in the wastewater;
adding sulfuric acid into the wastewater subjected to membrane treatment, adjusting the pH value to 4-5, then feeding the wastewater into an evaporator, performing negative pressure evaporation under 0.09MPa, condensing steam, adding hydrogen peroxide, performing oxidation treatment, adding activated carbon, filtering, and feeding the filtered water into a nitrobenzene catalytic hydrogenation reactor for reuse;
step four, when the wastewater in the step three is evaporated to 60-70% of the total volume under negative pressure, stopping evaporation, cooling the concentrated solution for crystallization, cooling to below 15 ℃, filtering and separating, and drying the filtered crystals to obtain a product ammonium sulfate;
and fifthly, adding ammonia gas into the filtrate obtained in the fourth step for neutralization, adjusting the pH value to 6.8-7.0, filtering and separating, drying the filtered p-aminophenol, and returning the filtrate to the evaporator in the third step.
Compared with the prior art, the invention adopting the technical scheme has the outstanding characteristics that:
(1) by the method, the p-aminophenol and the ammonium sulfate are respectively recovered after the p-aminophenol production wastewater is treated, and the treated water can be recycled and applied to the preparation process of the p-aminophenol, so that zero discharge of the wastewater is realized;
(2) the method has simple process and can realize industrial production.
Preferably, the invention further comprises:
in the third step, 30wt% of hydrogen peroxide is used for oxidation treatment.
The vacuum degree of the negative pressure evaporation in the third step is 0.09Mpa.
Drawings
FIG. 1 is a liquid phase spectrum of raw wastewater according to an embodiment of the present invention;
FIG. 2 is a liquid phase spectrum of wastewater after treatment according to the first embodiment of the present invention;
FIG. 3 is a liquid phase spectrum of a reaction solution after hydrogenation of wastewater treated according to the first embodiment of the present invention;
FIG. 4 is a liquid phase spectrum of the hydrogenated wastewater after the second treatment in the example of the present invention
The specific implementation mode is as follows:
the invention will be further illustrated by the following examples, which are intended only for a better understanding of the present invention and therefore do not limit the scope of the invention.
With reference to figures 1 to 4 of the drawings,
the first embodiment is as follows:
1. and (2) injecting 5000L of wastewater into the layering kettle at room temperature, then adding 1000L of methylbenzene, starting stirring, uniformly stirring, standing for 60min, then opening a valve below the layering kettle to separate the methylbenzene and the wastewater, injecting the wastewater into a storage tank A, injecting the methylbenzene into a recovery storage tank B, and then sending the methylbenzene to a rectification system to recover the methylbenzene and the aniline.
2. And (3) passing the extracted wastewater in the storage tank A through membrane filtration equipment, completely treating the emulsifier, and pumping the filtered water into an evaporation kettle.
3. Adding sulfuric acid into water in the evaporation kettle, adjusting the pH value to 4-5, then opening a steam valve of the evaporation kettle, opening a vacuum system, controlling the vacuum degree to be about 0.09MPa, condensing steam through a condenser, then feeding the steam into the receiving kettle, observing the liquid level of the receiving kettle, closing the steam valve of the evaporation kettle when the liquid level reaches 3000L, closing the vacuum system, and stopping evaporation.
4. Adding water in a receiving kettle into a decoloring kettle, adding 6kg of 30wt% hydrogen peroxide, heating to 60-65 ℃, adding 15kg of active carbon, stirring for 30min, filtering, and sending the filtrate to a water storage tank for producing p-aminophenol by catalytic hydrogenation of nitrobenzene for repeated hydrogenation.
5. The evaporator solution evaporated until 3000L of water was received by the receiving kettle. Stopping evaporation, cooling the concentrated solution for crystallization, cooling to below 15 deg.C, filtering, separating, drying solid ammonium sulfate, and feeding the filtrate into a neutralization kettle.
6. Neutralizing the solution in the neutralizing kettle to pH 6.8-7.0 with ammonia gas, filtering to obtain p-aminophenol, stoving, returning the filtrate to the evaporating kettle, and evaporating together with the waste water.
Example two:
1. and (2) pumping 6000L of wastewater into the layering kettle at room temperature, then adding 1200L of methylbenzene, starting stirring, uniformly stirring, standing for 60min, then opening a valve below the layering kettle to separate the methylbenzene and the wastewater, pumping the wastewater into a storage tank A, pumping the methylbenzene into a methylbenzene recovery storage tank B, and then delivering the methylbenzene and the methylbenzene to a rectification system to recover the methylbenzene and the aniline.
2. And (3) passing the extracted wastewater in the storage tank A through membrane filtration equipment, completely treating the emulsifier, and pumping the water into an evaporation kettle.
3. Adding sulfuric acid into water in the evaporation kettle, adjusting the pH value to 4-5, then opening a steam valve of the evaporation kettle, opening a vacuum system, controlling the vacuum degree to be about 0.09MPa, condensing steam through a condenser, then feeding the steam into the receiving kettle, observing the liquid level of the receiving kettle, closing the steam valve of the evaporation kettle, closing the vacuum system and stopping evaporation when the liquid level reaches 4000L.
4. Adding water in a receiving kettle into a decoloring kettle, adding 8kg of 30wt% hydrogen peroxide, heating to 60-65 ℃, adding 20kg of activated carbon, stirring for 30min, filtering, and sending the filtrate to a water storage tank for producing p-aminophenol by catalytic hydrogenation of nitrobenzene for repeated hydrogenation.
5. When the solution in the evaporation kettle is evaporated to a receiving kettle and 3000L of water is received, the evaporation is stopped, the concentrated solution is cooled and crystallized, the temperature is reduced to below 15 ℃, the solution is filtered and separated, the solid ammonium sulfate is dried, and the filtrate is pumped into a neutralization kettle.
6. Neutralizing the solution in the neutralizing kettle to pH 6.8-7.0 with ammonia gas, filtering to obtain p-aminophenol, stoving, returning the filtrate to the evaporating kettle, and evaporating together with the waste water.
TABLE 1 content (g/L) of organic matters in the original wastewater and the treated wastewater
| Serial number | P-aminophenol | Ortho-aminophenols | Aniline | 4-4 ， Diaminodiphenyl ether |
| Raw waste water | 3.78 | 1.42 | 1.78 | 0.034 |
| Treated wastewater | Not detected out | Not detected out | 0.029 | Not detected out |
Content (g/L) of organic matters in the wastewater of TABLE II and the treated wastewater
| Serial number | P-aminophenol | Ortho-aminophenols | Aniline | 4-4 ， Diaminodiphenyl ether |
| Raw waste water | 2.88 | 0.71 | 1.34 | 0.027 |
| Treated wastewater | Not detected out | Not detected out | 0.012 | Not detected out |
The embodiment of the invention is used in factory production all the time to achieve the beneficial effect.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the scope of the present invention, which is defined in the appended claims.
Claims (3)
1. A treatment method of wastewater generated in p-aminophenol production by nitrobenzene catalytic hydrogenation is characterized by comprising the following steps:
step one, adding toluene into the wastewater, extracting aniline in the wastewater, standing for 60min, and sending an extract to a rectification system to recover the toluene and aniline in the extract;
step two, the wastewater obtained after extraction in the step one is subjected to membrane treatment to remove an emulsifier in the wastewater;
adding sulfuric acid into the wastewater subjected to membrane treatment, adjusting the pH value to 4-5, then feeding the wastewater into an evaporator for negative pressure evaporation, condensing steam, performing oxidation treatment, adding activated carbon for filtration, and feeding the filtered water into a nitrobenzene catalytic hydrogenation reactor for reuse;
step four, when the wastewater in the step three is evaporated to 60-70% of the total volume under negative pressure, stopping evaporation, cooling the concentrated solution for crystallization, cooling to below 15 ℃, filtering and separating, and drying the filtered crystals to obtain a product ammonium sulfate;
and fifthly, adding ammonia gas into the filtrate obtained in the fourth step for neutralization, adjusting the pH value to 6.8-7.0, filtering and separating, drying the filtered p-aminophenol, and returning the filtrate to the evaporator obtained in the third step.
2. The method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene according to claim 1, wherein: 30wt% of hydrogen peroxide is used for the oxidation treatment in the third step.
3. The method for treating wastewater generated in the production of p-aminophenol by catalytic hydrogenation of nitrobenzene according to claim 1, wherein: the vacuum degree of the negative pressure evaporation in the third step is 0.09Mpa.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211330708.4A CN115521014A (en) | 2022-10-28 | 2022-10-28 | Method for treating wastewater generated in production of p-aminophenol by catalytic hydrogenation of nitrobenzene |
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| CN202211330708.4A CN115521014A (en) | 2022-10-28 | 2022-10-28 | Method for treating wastewater generated in production of p-aminophenol by catalytic hydrogenation of nitrobenzene |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845129A (en) * | 1970-01-28 | 1974-10-29 | Macfarlan Smith Ltd | Purification of p-aminophenol |
| JP2527652B2 (en) * | 1989-02-23 | 1996-08-28 | 株式会社大塚製薬工場 | P-aminophenol derivative, its production method and use |
| CN1168865A (en) * | 1997-06-19 | 1997-12-31 | 中国科学院成都有机化学研究所 | Method for treating the waste water from the prodn. of para-aminophenol by catalytic-hydrogenization of nitrobenzene |
| US6403833B1 (en) * | 2001-01-30 | 2002-06-11 | Council Of Scientific And Industrial Research | Single step hydrogenation of nitrobenzene to p-aminophenol |
| CN1636892A (en) * | 2004-11-17 | 2005-07-13 | 杨云军 | Combined process of treating high concentration and high colority effluent from acetaminophen production |
| CN1803641A (en) * | 2006-01-23 | 2006-07-19 | 南京大学 | Integrated process for treating waste water of p-aminophenol production and resource recovery method |
| CN108623092A (en) * | 2018-05-07 | 2018-10-09 | 常州大学 | A kind of method that processing prepares the waste water that para-aminophenol generates |
| CN111514941A (en) * | 2019-02-03 | 2020-08-11 | 南京大学 | Catalyst and method for one-step synthesis of p-aminophenol by catalyzing nitrobenzene hydrogenation |
-
2022
- 2022-10-28 CN CN202211330708.4A patent/CN115521014A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845129A (en) * | 1970-01-28 | 1974-10-29 | Macfarlan Smith Ltd | Purification of p-aminophenol |
| JP2527652B2 (en) * | 1989-02-23 | 1996-08-28 | 株式会社大塚製薬工場 | P-aminophenol derivative, its production method and use |
| CN1168865A (en) * | 1997-06-19 | 1997-12-31 | 中国科学院成都有机化学研究所 | Method for treating the waste water from the prodn. of para-aminophenol by catalytic-hydrogenization of nitrobenzene |
| US6403833B1 (en) * | 2001-01-30 | 2002-06-11 | Council Of Scientific And Industrial Research | Single step hydrogenation of nitrobenzene to p-aminophenol |
| CN1636892A (en) * | 2004-11-17 | 2005-07-13 | 杨云军 | Combined process of treating high concentration and high colority effluent from acetaminophen production |
| CN1803641A (en) * | 2006-01-23 | 2006-07-19 | 南京大学 | Integrated process for treating waste water of p-aminophenol production and resource recovery method |
| CN108623092A (en) * | 2018-05-07 | 2018-10-09 | 常州大学 | A kind of method that processing prepares the waste water that para-aminophenol generates |
| CN111514941A (en) * | 2019-02-03 | 2020-08-11 | 南京大学 | Catalyst and method for one-step synthesis of p-aminophenol by catalyzing nitrobenzene hydrogenation |
Non-Patent Citations (1)
| Title |
|---|
| 李志强: "硝基苯催化加氢制对氨基苯酚工艺研究", 山西化工, no. 3, 15 August 1997 (1997-08-15), pages 10 - 12 * |
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