CN106892829A - The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol - Google Patents
The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol Download PDFInfo
- Publication number
- CN106892829A CN106892829A CN201510952424.2A CN201510952424A CN106892829A CN 106892829 A CN106892829 A CN 106892829A CN 201510952424 A CN201510952424 A CN 201510952424A CN 106892829 A CN106892829 A CN 106892829A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- nitrophenol
- aminophenol
- reaction
- nickel
- 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 abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 28
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 62
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000002815 nickel Chemical class 0.000 claims description 2
- 238000005554 pickling Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 7
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 239000013589 supplement Substances 0.000 abstract description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001994 activation Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance 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)
Abstract
The present invention discloses a kind of method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol.The method of the present invention is first to add p-nitrophenol in a kettle., adds ethanol and loaded catalyst, and closed reactor, with the air in the complete replacement reaction kettle of hydrogen, then keeps in kettle being normal pressure（0.1MPa）And begin to warm up stirring, temperature is passed through hydrogen in kettle after reaching 60 DEG C, kettle internal pressure power is set to remain to 1.0~3.0MPa, start hydrogenation reaction, conversion ratio is to reach 98~99% after being hydrogenated with about 0.5 to 1.5 hour, is then demultiplex out reactant mixture and catalyst, the catalyst isolated returns to reactor and is continuing with, and supplements the catalyst of loss amount；Product separation is carried out to reactant mixture, i.e. clear liquid, para-aminophenol is obtained.
Description
Technical field
The present invention relates to the method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol.
Background technology
Nitro compound is by being reduced to amino-compound, it is earliest to be prepared by the method for iron powder and hydrochloric acid, the method is seriously polluted, for country expressly provides the process route to be abolished at no distant date, such production most of in recent years uses Raney's nickel catalyst, realized by the conversion of nitro to amino by catalytic hydrogenation by catalyst of Raney's nickel, but carry out catalytic hydrogenation using Raney's nickel catalyst and have the disadvantages that：
1) using extremely inconvenient.Because the active composition of the Raney's nickel catalyst for carrying out catalytic hydrogenation is skeleton nickel, but skeleton nickel is easily caught fire in atmosphere, cannot preserve, can only be in nickel-Al alloy powder form as commodity, using preceding needing aluminium to be dissolved away with alkali, reaction system is added after wash clean under conditions of air is completely cut off；In addition, the catalysis activity of Raney's nickel often because treatment conditions (such as alkali soluble and wash conditions) it is different change a lot.
2) its byproduct of reaction amount is larger when using Raney's nickel catalyst, and product yield is low.Raney's nickel catalyst hydrogenation makes nitro be converted into amino to generally require temperature higher, commonly required temperature is higher than 100 DEG C, and the product amino compound being hydrogenated to easily generation accessory substance at a temperature of higher than 100 DEG C (is industrially referred to as tar, this aspect reduces product yield, on the other hand can also affect on reaction and is normally carried out.
3) catalyst consumption amount is big.Because raney ni catalysis activity is low, the catalytic amount of required addition is larger, on the other hand because catalyst reclaims extremely difficult, causes the consumption of catalyst excessive, causes production cost higher.
4) huge potential safety hazard is there is in producing.It is careless slightly in operation that fire will occur because Raney's nickel is shown in that air easily catches fire；Workshop is hydrogenated with simultaneously and there is hydrogen, easily explode.
The content of the invention
The present invention provides one kind can overcome prior art not enough, the method that the p-nitrophenol catalytic hydrogenation with higher-security and higher yields prepares para-aminophenol.
In the present invention, the method that p-nitrophenol prepares para-aminophenol is：P-nitrophenol, ethanol and loaded catalyst are first separately added into reactor, the amount of alcohol for wherein adding is 3~4 times of the p-nitrophenol for adding, the nickel catalyst carried amount for adding is the 10~15% of the p-nitrophenol quality for adding, hydrogenation reaction is carried out at 60~95 DEG C 0.5~1.5 hour, hydrogenation reaction pressure is 1.5~3.0MPa, separation of solid and liquid is carried out after the completion of reaction, the supernatant isolated carries out product separation, and defeated time reaction system is continuing with the solid catalyst isolated again.
The method that p-nitrophenol of the present invention prepares para-aminophenol can be that reaction mass is transferred into heat insulation tank after completion of the reaction to carry out heat preservation settlement, and isolating supernatant carries out product separation, obtains para-aminophenol；New p-nitrophenol and ethanol is added by aforementioned quantities in reactor, while the bottom solidliquid mixture (catalyst and a small amount of reactant mixture) that will be isolated from heat insulation tank
Again defeated time reactor is continuing with.
The method for preparing para-aminophenol of the present invention can also be that the supported catalyst dosage of addition is the 13% of para-aminophenol quality, and reaction temperature is 90 DEG C, and pressure is 1.5MPa in kettle during hydrogenation.
The method of the present invention employs load-type nickel hydrogenation catalyst, this aerial ignition temperature of catalyst is more than 150 DEG C, because catalyst of the invention has carried out purification process with the inert gas of mixing, make it locally in passive state, therefore it can be deposited safely, can directly feed intake in use and use, without carrying out activation process again.Through actual measurement, its hydrogenation catalyst initial temperature of catalyst of the invention is 60 DEG C, and hydrogenation catalyst reaction temperature is less than 100 DEG C, and can be used for all kinds of nitro compound hydrogenation catalysts.Because catalyst reaction temperature of the invention is less than 100 DEG C, therefore can avoid generating the polymers such as tar in reactant completely, it is carried out continuously reaction, experiment also shows, catalyst of the invention can be reused, and this catalyst consumption in use is less than existing all kinds of catalyst, also below 6504K catalyst and 0104G catalyst, and its catalytic effect is higher than existing all kinds of catalyst, therefore with obvious cost advantage.Pressure during catalytic hydrogenation of the present invention is relatively low, and embodiment is chatted after, and hydrogenation pressure is only 1.5MPa in its optimised process, and this pressure will substantially be less than prior art.In addition, from the present invention, this method can also simplify whole production technology.
Specific embodiment
Embodiment：The method that p-nitrophenol prepares para-aminophenol
100 grams of p-nitrophenols are first added in a kettle., the concentration for adding 4 times of p-nitrophenol quality is 95% ethanol, add the 10~15% of p-nitrophenol quality loaded catalyst, closed reactor, with the air in the complete replacement reaction kettle of hydrogen, then keep in kettle being normal pressure (about 0.1MPa), and begin to warm up stirring, temperature is passed through hydrogen in kettle after reaching 60 DEG C, kettle internal pressure power is remained to 1.0~3.0MPa (experiment shows that its optimum pressure should be 1.5MPa or so), start hydrogenation reaction, temperature in the kettle is maintained in the range of 70~95 DEG C in hydrogenation process, conversion ratio is to reach 88 after being hydrogenated with about 0.5 to 1.5 hour
~90%, reactant mixture and catalyst are then demultiplex out, the catalyst isolated returns to reactor and is continuing with, and supplements the catalyst of loss amount, and experiment shows only to need the catalytic amount added to be about 100 milligrams every time；Product separation is carried out to reactant mixture, i.e. clear liquid, para-aminophenol is obtained more than 76.8 grams.In the present invention, the specific method for being used is that first reaction system is transferred in heat preservation settlement tank to carry out catalyst and separated with reactant mixture.
Experiment shows, in above-mentioned course of reaction, the supported catalyst dosage of addition is the 13% of the p-nitrophenol quality for adding, and pressure is 1.5Mpa in kettle during hydrogenation, and when reaction temperature is 90 DEG C, conversion ratio is to reach more than 98.0% in 1 hour.
Of the invention used loaded catalyst preparation method it is following (on loaded catalyst of the invention referring also to entitled " a kind of method for preparing catalyst and catalyst for catalytic hydrogenation of nitro compound " Chinese invention patent application)：
Of the invention used loaded catalyst preparation method it is following (on loaded catalyst of the invention referring also to entitled " a kind of method for preparing catalyst and catalyst for catalytic hydrogenation of nitro compound " Chinese invention patent application)：
The diatomaceous treatment of A
Found according to experiment, influence as the impurity in the diatomite of carrier to catalyst is very big, and wherein with the influence of iron as most, effectively to remove the iron in diatomite, generally using acid cleaning process, but found according to related experiment, diatomite treatment employs following technique can optimal effect, it not only can effectively remove impurity therein, particularly iron, but also the catalyst product is had optimal catalytic effect：
It is its 3 times that diatomite first is added into volume ratio, concentration be 3~20% aqueous hydrochloric acid solution in be stirred, then continue after being warmed up to 90 DEG C to stir 1 hour, leach diatomite and carry out dried process after washing with water, obtain as the diatomite of catalyst carrier.
Detection indicate that, resulting diatomite processed by the invention is in total hole volume 0.15~0.4ml/g scopes；Its specific surface area is 120~200m2/g.Shown according to experiment, diatomite treatment optimal aqueous hydrochloric acid solution concentration used is best for 10%.
The preparation of B catalyst
Nickel is first made nitrate, the aqueous solution of 1M is configured to again, take the nickel salt aqueous solution that the amount of nickel is for the 45~58% of finished catalyst quality, add the silica aqueous solution containing silica 20%, the amount of the silica aqueous solution for being added should ensure that make silica volume therein account for finished catalyst quality 1~4%, system is heated to 50~80 DEG C, the 35~55% of finished catalyst quality diatomite is added under agitation, then by the pH of system
Value is adjusted to 7.5~8.5, stirred 12~16 hours under the conditions of 50~80 DEG C, separation of solid and liquid is carried out after cooling, resulting solid carries out granulating and drying treatment after washing with water, finished catalyst is obtained at 500~700 DEG C with hydrogen reduction, then after being passivated treatment in the cooling condition with the mixing inert gas of the air containing volume ratio 5%.
During made above, when nickel in the nitrate of nickel used and finished catalyst mass ratio are 55%, system temperature is 60 DEG C in reaction, and pH values are adjusted to 7.8, and the catalyst of optimal catalytic effect can be obtained when hydrogen reduction temperature is 550 DEG C.
The catalyst actual measurement parameter obtained through above-mentioned technique is as follows：
(1) nickel content is 45~58% (most preferably 55%)；
(2) heap density is 0.6~0.9g/ml (optimum value is 0.75)；
(3) 0.15~0.4ml/g of total hole volume (optimum value is 0.35)；
(4) 120~200m2/g of specific surface area (optimum value is 160 m2/g)；
(5) nickel crystal size 40~200 (optimum value is 60)；
(6) catch fire 170 DEG C of warm spot in air
(7) reduction ratio (Ni0/NiO) 60~80% (optimum value is 70%).
Catalyst of the invention see the table below with foreign similar catalyst contrast test data：
。
Claims (3)
1. the method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol, p-nitrophenol is added in reactor, ethanol and nickel catalyst carried, the amount of alcohol for wherein adding is 3~4 times of the p-nitrophenol quality for adding, catalyst amount is the 10~15% of the p-nitrophenol quality for adding, 60~95 DEG C carry out hydrogenation reaction 0.5~1.5 hour, hydrogenation reaction pressure is 1.0~3.0MPa, separation of solid and liquid is carried out after the completion of reaction, the supernatant isolated carries out product separation, again defeated time reaction system is continuing with the solid isolated, it is characterized in that what is used is nickel catalyst carried with the preparation of following methods：Nickel is first made nitrate,The aqueous solution of 1M is configured to again,Take the nickel salt aqueous solution that the amount of nickel is for the 45~58% of finished catalyst quality,Add the silica aqueous solution containing silica 20%,The amount of the silica aqueous solution for being added should ensure that make silica volume therein account for finished catalyst quality 1~4%,System is heated to 50~80 DEG C,The prior through pickling processes diatomite of finished catalyst quality 35~55% is added under agitation,The pH values of system are adjusted to 7.5~8.5 again,Stirred 12~16 hours under the conditions of 50~80 DEG C,Separation of solid and liquid is carried out after cooling,Resulting solid carries out granulating and drying treatment after washing with water,At 500~700 DEG C with hydrogen reduction,Finished catalyst is obtained after being passivated treatment in the cooling condition with the mixing inert gas of the air containing volume ratio 5% again.
2. the method that the p-nitrophenol catalytic hydrogenation according to claim 1 prepares para-aminophenol, it is characterised in that reaction mass is transferred into heat insulation tank after the completion of reaction carries out heat preservation settlement, isolating supernatant carries out product separation, obtains para-aminophenol；Add new p-nitrophenol and ethanol by aforementioned quantities in reactor, at the same the bottom solidliquid mixture that will be isolated from heat insulation tank defeated time reactor is continuing with again.
3. the method that the p-nitrophenol catalytic hydrogenation according to claim 1 or 2 prepares para-aminophenol, it is characterised in that the nickel catalyst carried amount of addition is the 13% of p-nitrophenol quality, and reaction temperature is 90 DEG C, pressure is 1.5MPa in kettle during hydrogenation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510952424.2A CN106892829A (en) | 2015-12-19 | 2015-12-19 | The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510952424.2A CN106892829A (en) | 2015-12-19 | 2015-12-19 | The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106892829A true CN106892829A (en) | 2017-06-27 |
Family
ID=59189228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510952424.2A Pending CN106892829A (en) | 2015-12-19 | 2015-12-19 | The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106892829A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107986977A (en) * | 2017-10-26 | 2018-05-04 | 苏州盖德精细材料有限公司 | A kind of method that loaded catalyst catalysis using aluminium oxide as carrier prepares para-aminophenol |
| CN111302955A (en) * | 2020-04-08 | 2020-06-19 | 江苏扬农化工集团有限公司 | Synthesis method of aminophenol |
| CN116178181A (en) * | 2023-02-27 | 2023-05-30 | 安徽东至广信农化有限公司 | A kind of p-aminophenol production process |
-
2015
- 2015-12-19 CN CN201510952424.2A patent/CN106892829A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107986977A (en) * | 2017-10-26 | 2018-05-04 | 苏州盖德精细材料有限公司 | A kind of method that loaded catalyst catalysis using aluminium oxide as carrier prepares para-aminophenol |
| CN111302955A (en) * | 2020-04-08 | 2020-06-19 | 江苏扬农化工集团有限公司 | Synthesis method of aminophenol |
| CN116178181A (en) * | 2023-02-27 | 2023-05-30 | 安徽东至广信农化有限公司 | A kind of p-aminophenol production process |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102285891B (en) | Method for preparing arylamine by catalytic hydrogenation of aromatic nitro compound | |
| CN106892828A (en) | A kind of paranitroanisole Hydrogenation for paraphenetidine method | |
| CN106892829A (en) | The method that p-nitrophenol catalytic hydrogenation prepares para-aminophenol | |
| CN103894188B (en) | A kind of preparation method and applications of palladium-resin C catalyst | |
| CN101434550B (en) | Method for preparing 1-naphthylamine from 1-nitronaphthalene | |
| CN101475488B (en) | Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene | |
| CN103214437B (en) | Continuous production method of 2-methyl tetrahydrofuran | |
| CN100465145C (en) | The preparation method of 1,4-cyclohexanedimethanol | |
| CN101434547B (en) | Method for preparing aniline from nitrobenzene | |
| CN103450017B (en) | Preparation method of methyl acetoacetate | |
| CN101481314B (en) | Method for preparing X substituted aniline from X substituted nitrobenzene | |
| CN106543017A (en) | A kind of preparation method of 4 aminocyclohexyl acetic acid | |
| CN103992230B (en) | Oil of mirbane mixture containing dinitrobenzene prepares the method for diaminobenzene and aniline | |
| CN101434548B (en) | Method for preparing diaminobenzene from dinitro benzene | |
| CN101323579A (en) | Method for preparing m-phenylenediamine | |
| CN101434549B (en) | Method for preparing 1, 4-diaminonaphthalene from 1, 4-dinitronaphthalene | |
| CN101439285B (en) | Method for preparing catalyst for catalytic hydrogenation of nitro compound and catalyst | |
| CN106892831A (en) | The method that paranitrobenzaldehyde catalytic hydrogenation prepares para aminotenzaldehyde | |
| CN106892827A (en) | With the nickel catalyst carried method for being catalyzed ortho-nitraniline Hydrogenation for o-phenylenediamine | |
| CN106892853A (en) | The method that 4- nitroindolines or 5- nitroindoline catalytic hydrogenations prepare amino indole | |
| CN101514162B (en) | Method for preparing X-substituted diaminobenzene from X-substituted dinitrobenzene | |
| CN106732714B (en) | Indoxacarb intermediate catalyst for synthesizing and preparation method thereof | |
| CN106083622B (en) | A kind of preparation method of mebendazole intermediate 3,4- diaminobenzophenones | |
| CN108658787A (en) | The preparation method of ethamine | |
| CN101475489B (en) | Method for preparing X substituted 1-naphthylamine from X substituted 1-nitronaphthalene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170627 |
|
| WD01 | Invention patent application deemed withdrawn after publication |