CN101481314B - Method for preparing X substituted aniline from X substituted nitrobenzene - Google Patents
Method for preparing X substituted aniline from X substituted nitrobenzene Download PDFInfo
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- CN101481314B CN101481314B CN2008101742037A CN200810174203A CN101481314B CN 101481314 B CN101481314 B CN 101481314B CN 2008101742037 A CN2008101742037 A CN 2008101742037A CN 200810174203 A CN200810174203 A CN 200810174203A CN 101481314 B CN101481314 B CN 101481314B
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Abstract
The invention discloses a method for preparing X substituted aniline by catalytic hydrogenation of X substituted nitrobenzene; wherein the X can be any one of -F, -Cl, -Br, -OCH3, -OH or-R, R is saturated hydrocarbyl with one or more carbons and the position of X in the nitrobenzene is ortho position, or meta position, or para position of nitryl. The method comprises the following steps: adding Xsubstituted nitrobenzene in a reaction kettle; and then adding ethanol and a supported catalyst; sealing the reaction kettle; completely replacing air in the reaction kettle with hydrogen; maintaining normal pressure in the reaction kettle and heating and stirring the mixture; introducing the hydrogen into the kettle after the temperature reaches 60 DEG C; maintaining the pressure in the kettle between 1.0 and 3.0 MPa; starting hydrogenation reaction and maintaining the temperature in the kettle between 60 and 90 DEG C during the hydrogenation process; and separating reaction mixture and the catalyst when the conversion rate reaches 95-99 percent after hydrogenation for 3 to 8 hours.
Description
Technical field
The present invention relates to the method that the substituted oil of mirbane shortening of X prepares the substituted aniline of X, the X here can be-F ,-Cl ,-Br ,-OCH
3,-OH, perhaps-among the R any, wherein R is the saturated hydrocarbyl of 1 carbon or 1 above carbon, the position of X in oil of mirbane is ortho position or a position or the contraposition of nitro.
Background technology
Nitro-compound is through being reduced to aminocompound; Be method preparation the earliest through iron powder and hydrochloric acid; This method is seriously polluted, and for country expressly provides the operational path that will abolish at no distant date, most of in recent years this type of produced and all adopted Raney's nickel catalyst; Promptly be that catalyzer passes through the shortening realization by the conversion of nitro to amino, have following shortcoming but use Raney's nickel catalyst to carry out shortening with the Raney's nickel:
1) uses extremely inconvenience.Because carrying out the Raney's nickel catalyst of shortening, to have active composition be skeleton nickel; But skeleton nickel is very easily caught fire in air; Can't preserve; Can only be with nickel-Al alloy powder form as commodity, need aluminium be dissolved away with alkali before using, under the condition of secluding air, add reaction system behind the wash clean; In addition, the catalytic activity of Raney's nickel is often because of different the changing a lot of treatment condition (dissolving and wash conditions like alkali).
Its byproduct of reaction amount is bigger when 2) using Raney's nickel catalyst, and product yield is low.The Raney's nickel catalyst hydrogenation makes nitro be converted into the amino higher temperature that often needs; General temperature requiredly to be higher than 100 ℃; And the product amino compound that hydrogenation generates is prone to generate by product and (is referred to as tar in the industry being higher than under 100 ℃ of temperature; This makes product yield reduce on the one hand, also possibly have influence on reaction on the other hand and normally carry out.
3) the catalyst consumption amount is big.Because the raney ni catalysis activity is low, the catalytic amount of required adding is bigger, and is extremely difficult because of catalyst recovery on the other hand, causes the consumption of catalyzer excessive, causes production cost higher.
4) exist huge potential safety hazard in the production.Because Raney's nickel sees that air is prone to catch fire, careless slightly in the operation will presence of fire; There is hydrogen in the hydrogenation workshop simultaneously, very easily blasts.
Summary of the invention
The present invention provides a kind of prior art deficiency that overcomes, and what have higher-security and higher yields prepares the method for the substituted aniline of X with the substituted oil of mirbane shortening of X.
Among the present invention; The method that the substituted oil of mirbane shortening of X prepares the substituted aniline of X is: in reaction kettle, add earlier the substituted oil of mirbane of X, ethanol and loaded catalyst respectively; The amount of alcohol that wherein adds is 10～30% of the substituted oil of mirbane quality of X that adds, and the nickel catalyst carried amount of adding was carried out hydrogenation reaction 3～8 hours for 3～6% of the substituted oil of mirbane quality of X that adds at 60～90 ℃; Hydrogenation reaction pressure is 1.5～3.0MPa; Reaction is carried out solid-liquid separation after accomplishing, and separated liquid supernatant is carried out the product separation, and isolated solid catalyst is failed back reaction system again and continued to use.
The method that the substituted oil of mirbane shortening of X of the present invention prepares the substituted aniline of X can be after reaction is accomplished, to change reaction mass over to the insulation jar to be incubated sedimentation, isolates supernatant and carries out the product separation, obtains the substituted aniline of X; Reaction kettle is interior to add new substituted oil of mirbane of X and ethanol by aforementioned quantities, will from the insulation jar, fail back reaction kettle continuation use again by isolated bottom solidliquid mixture (catalyzer and a small amount of reaction back mixture) simultaneously.
The method that the substituted oil of mirbane shortening of X of the present invention prepares the substituted aniline of X can also be that the supported catalyst dosage that adds is 4% of the substituted oil of mirbane quality of X, and temperature of reaction is 90 ℃, and the still internal pressure during hydrogenation is 1.5MPa.
Method of the present invention has adopted the load-type nickel hydrogenation catalyst; The aerial kindling temperature of this catalyzer is greater than 150 ℃; Because catalyzer of the present invention carried out purification process with the blended inert gas, make its part be in passive state, so it can safe storage; The use that in use can directly feed intake need not to carry out activation treatment again.Through actual measurement, its hydrogenation catalyst starting temperature of catalyzer of the present invention is 60 ℃, and the hydrogenation catalyst temperature of reaction is lower than 100 ℃, and can be used for all kinds of catalytic hydrogenation of nitro compound.Because catalyst temperature of reaction of the present invention less than 100 ℃, therefore can avoid in reactant, generating polymers such as tar fully, and reaction is carried out continuously; Test also shows; Catalyzer of the present invention can be reused, and this catalyzer consumption in use is lower than existing all kinds of catalyzer, also is lower than 6504K catalyzer and 0104G catalyzer; And its catalytic effect is higher than existing all kinds of catalyzer, therefore has tangible cost advantage.Pressure during shortening of the present invention is also lower, from after to chat embodiment visible, hydrogenation pressure is merely 1.5MPa in its optimised process, this pressure obviously will be lower than prior art.In addition, visible from the present invention, this method can also be simplified whole production technique.
Embodiment
The substituted aniline of the substituted oil of mirbane preparation-F of embodiment 1:-F, in this example-the substituted position of F is the ortho position at nitro.
The substituted oil of mirbane 100 of adding-F restrains in reaction kettle earlier, and 20% of the substituted oil of mirbane quality of adding-F concentration is 95% ethanol again, 3～6% of the more substituted oil of mirbane quality of adding-F loaded catalyst; Closed reactor with the air in the complete replacement reaction kettle of hydrogen, keeps being in the still normal pressure (being about 0.1MPa) then; And beginning heated and stirred; Feed hydrogen after temperature reaches 60 ℃ in the still, make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa), the beginning hydrogenation reaction; Temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process; Hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%, isolate reaction mixture and catalyzer then, isolated catalyzer returns reaction kettle and continue to use; The catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain substituted aniline 75～78 grams of F.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-the substituted oil of mirbane quality of F 4%, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
The substituted aniline of the substituted oil of mirbane preparation-Cl of embodiment 2:-Cl, in this example-position between nitro, the substituted position of Cl.
The substituted oil of mirbane 100 of adding-Cl restrains in reaction kettle earlier, and 20% of the substituted oil of mirbane quality of adding-Cl concentration is 95% ethanol again, 3～6% of the more substituted oil of mirbane quality of adding-Cl loaded catalyst; Closed reactor with the air in the complete replacement reaction kettle of hydrogen, keeps being in the still normal pressure (being about 0.1MPa) then; And beginning heated and stirred; Feed hydrogen after temperature reaches 60 ℃ in the still, make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa), the beginning hydrogenation reaction; Temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process; Hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%, isolate reaction mixture and catalyzer then, isolated catalyzer returns reaction kettle and continue to use; The catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-substituted aniline 77～80 grams of Cl.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-the substituted oil of mirbane quality of Cl 4%, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
The substituted aniline of the substituted oil of mirbane preparation-Br of embodiment 3:-Br, in this example-the substituted position of Br is the contraposition at nitro.
The substituted oil of mirbane 100 of adding-Br restrains in reaction kettle earlier, and 20% of the substituted oil of mirbane quality of adding-Br concentration is 95% ethanol again, 3～6% of the more substituted oil of mirbane quality of adding-Br loaded catalyst; Closed reactor with the air in the complete replacement reaction kettle of hydrogen, keeps being in the still normal pressure (being about 0.1MPa) then; And beginning heated and stirred; Feed hydrogen after temperature reaches 60 ℃ in the still, make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa), the beginning hydrogenation reaction; Temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process; Hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%, isolate reaction mixture and catalyzer then, isolated catalyzer returns reaction kettle and continue to use; The catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-substituted aniline 81～84 grams of Br.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-the substituted oil of mirbane quality of Br 4%, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
Embodiment 4:-OCH
3Substituted oil of mirbane preparation-OCH
3Substituted aniline, in this example-OCH
3Substituted position is the position between nitro.
Adding-the OCH in reaction kettle of elder generation
3Substituted oil of mirbane 100 gram, adding-OCH again
320% concentration of substituted oil of mirbane quality is 95% ethanol, adding-OCH again
33～6% loaded catalyst of substituted oil of mirbane quality, closed reactor is with the air in the complete replacement reaction kettle of hydrogen; Keep then being normal pressure (being about 0.1MPa) in the still, and the beginning heated and stirred, after reaching 60 ℃, temperature feeds hydrogen in the still; Make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa); The beginning hydrogenation reaction, temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process, hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%; Isolate reaction mixture and catalyzer then; Isolated catalyzer returns reaction kettle to be continued to use, the catalyzer of replenish loss amount, and test shows that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-OCH
3Substituted aniline 76～79 grams.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-OCH
34% of substituted oil of mirbane quality, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
The substituted aniline of the substituted oil of mirbane preparation-OH of embodiment 5:-OH, in this example-the substituted position of OH is the ortho position at nitro.
The substituted oil of mirbane 100 of adding-OH restrains in reaction kettle earlier, and 20% of the substituted oil of mirbane quality of adding-OH concentration is 95% ethanol again, 3～6% of the more substituted oil of mirbane quality of adding-OH loaded catalyst; Closed reactor with the air in the complete replacement reaction kettle of hydrogen, keeps being in the still normal pressure (being about 0.1MPa) then; And beginning heated and stirred; Feed hydrogen after temperature reaches 60 ℃ in the still, make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa), the beginning hydrogenation reaction; Temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process; Hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%, isolate reaction mixture and catalyzer then, isolated catalyzer returns reaction kettle and continue to use; The catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-substituted aniline 73～76 grams of OH.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-the substituted oil of mirbane quality of OH 4%, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
The substituted aniline of the substituted oil of mirbane preparation-OH of embodiment 6:-OH, in this example-the substituted position of OH is the contraposition at nitro.
The substituted oil of mirbane 100 of adding-OH restrains in reaction kettle earlier, and 20% of the substituted oil of mirbane quality of adding-OH concentration is 95% ethanol again, 3～6% of the more substituted oil of mirbane quality of adding-OH loaded catalyst; Closed reactor with the air in the complete replacement reaction kettle of hydrogen, keeps being in the still normal pressure (being about 0.1MPa) then; And beginning heated and stirred; Feed hydrogen after temperature reaches 60 ℃ in the still, make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa), the beginning hydrogenation reaction; Temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process; Hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%, isolate reaction mixture and catalyzer then, isolated catalyzer returns reaction kettle and continue to use; The catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-substituted aniline 73～76 grams of OH.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding for add-the substituted oil of mirbane quality of OH 4%, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
Embodiment 7:-C
2H
5Substituted oil of mirbane preparation-C
2H
5Substituted aniline, in this example-C
2H
5Substituted position is the ortho position at nitro.
Adding-the C in reaction kettle of elder generation
2H
5Substituted oil of mirbane 100 gram, adding-C again
2H
520% concentration of substituted oil of mirbane quality is 95% ethanol, adding-C again
2H
53～6% loaded catalyst of substituted oil of mirbane quality, closed reactor is with the air in the complete replacement reaction kettle of hydrogen; Keep then being normal pressure (being about 0.1MPa) in the still, and the beginning heated and stirred, after reaching 60 ℃, temperature feeds hydrogen in the still; Make the still internal pressure remain to 1.0～3.0MPa (test shows that its optimum pressure should be about 1.5MPa); The beginning hydrogenation reaction, temperature in the kettle remains in 60～90 ℃ of scopes in hydrogenation process, hydrogenation after about 3 to 8 hours transformation efficiency promptly reach 95%～99%; Isolate reaction mixture and catalyzer then; Isolated catalyzer returns reaction kettle to be continued to use, the catalyzer of replenish loss amount, and test shows that the catalytic amount that at every turn only need add is about 90 milligrams; To reaction mixture (be clear liquid } carry out reaction product and separate, obtain-C
2H
5Substituted aniline 76～79 grams.In the present invention, the concrete grammar that is adopted is reaction system to be changed over to carry out in the insulation slurry tank separating of catalyzer and reaction mixture earlier.
Test shows that in above-mentioned reaction process, the supported catalyst dosage of adding is what add :-C
2H
54% of substituted oil of mirbane quality, the still internal pressure during hydrogenation is 1.5Mpa, when temperature of reaction was 90 ℃, transformation efficiency can reach more than 99.0% in 4 hours.
Relevant experiment also shows, adopts method of the present invention to be used for 1 carbon or to carrying out shortening more than the substituted oil of mirbane of the stable hydrocarbon of 1 carbon, and be used for-F ,-Cl ,-Br ,-OCH
3Or-the substituted and oil of mirbane of its position in other position of nitro of OH carries out shortening all has the result similar with aforementioned result.
The used supported catalyst preparation method of the present invention (also can be called the Chinese invention patent application of " a kind of method for preparing catalyst and catalyzer that is used for catalytic hydrogenation of nitro compound " referring to name) as follows about loaded catalyst of the present invention:
The used supported catalyst preparation method of the present invention (also can be called the Chinese invention patent application of " a kind of method for preparing catalyst and catalyzer that is used for catalytic hydrogenation of nitro compound " referring to name) as follows about loaded catalyst of the present invention:
The diatomaceous processing of A
Find according to experiment, very big as the impurity in the zeyssatite of carrier to the influence of catalyzer, and wherein with the influence of iron for; For effectively removing the iron in the zeyssatite, generally all adopt acid cleaning process, but find according to relevant test; Zeyssatite is handled and has been adopted following technology that best effect can be arranged; It not only can effectively remove impurity wherein, particularly iron, but also can make catalyst product that best catalytic effect is arranged:
Earlier zeyssatite is added volume ratio and be its 3 times, concentration is to stir in 3～20% the aqueous hydrochloric acid, is warmed up to 90 ℃ of continued again and stirs 1 hour, leaches zeyssatite also with the laggard capable drying treatment of water washing, obtains the zeyssatite as support of the catalyst.
Show through detecting, handle resulting zeyssatite in total hole volume 0.15～0.4ml/g scope through the present invention; Its specific surface area is 120～200m
2/ g.Show that according to test it is 10% best that zeyssatite is handled used best aqueous hydrochloric acid concentration.
The B Preparation of catalysts
Nickel is processed nitrate salt earlier, be mixed with the aqueous solution of 1M again, the amount of getting nickel is 45～58% a nickel salt aqueous solution of catalyzer final product quality; Add the silica aqueous solution that contains silicon-dioxide 20% again; The amount of the silica aqueous solution that is added should guarantee to make silica volume wherein to account for 1～4% of catalyzer final product quality, and system is heated to 50～80 ℃, 35～55% of adding catalyzer final product quality zeyssatite under agitation condition; PH value with system transfers to 7.5～8.5 again; Under 50～80 ℃ of conditions, stirred 12～16 hours, carry out solid-liquid separation after the cooling, resulting solid is handled with the laggard capable granulating and drying of water washing; Use hydrogen reduction at 500～700 ℃, under cooling conditions, carry out obtaining the catalyzer finished product after the Passivation Treatment with the Air mixing inert gas that contains volume ratio 5% again.
In the above preparation process, nickel is 55% with catalyzer final product quality ratio in the nitrate salt of used nickel, and system temperature is 60 ℃ in the reaction, and the pH value transfers to 7.8, can obtain the catalyzer of best catalytic effect when the hydrogen reduction temperature is 550 ℃.
The catalyzer actual measurement parameter that obtains through above-mentioned technology is following:
(1) nickel content is 45～58% (the best is 55%);
(2) bulk density is 0.6～0.9g/ml (optimum value is 0.75);
(3) total hole volume 0.15～0.4ml/g (optimum value is 0.35);
(4) specific surface area 120～200m
2(optimum value is 160m to/g
2/ g);
(5) nickel crystal size
; (optimum value is
);
(6) catch fire in the air 170 ℃ of warm spots
(7) reduction ratio (Ni0/NiO) 60～80% (optimum value is 70%).
Catalyzer of the present invention and foreign similar catalyst contrast test data see the following form:
| ? | Catalyzer of the present invention | Germany Louis that Company products 6504K | U.S. An Geer Company products 0104G |
| Nickel content (%) | 55 | 58 | 58 |
| Specific surface area (m 2/g) | 158 | 129 | 109 |
| Total pore volume (ml/g) | 0.36 | 0.36 | 0.35 |
| Bulk density (g/cm 3) | 11.7 | 11.7 | 11.6 |
| Brilliant size (the A of nickel 0) | 55～65 | 55～65 | 55～65 |
| Spontaneous ignition temperature (C 0) | ≥150 | ≥150 | ≥150 |
| The hydrogenation catalyst starting temperature | ≥60 | ≥90 | ≥90 |
Claims (3)
1.X substituted oil of mirbane shortening prepares the method for the substituted aniline of X, and X is-F ,-Cl ,-Br ,-OCH
3,-OH, perhaps-among the R any; Wherein R is the saturated hydrocarbyl of 2 above carbon; The position of X in oil of mirbane is ortho position or a position or the contraposition of nitro, it is characterized in that in reaction kettle adding the substituted oil of mirbane of X, ethanol and nickel catalyst carried, and the amount of alcohol that wherein adds is 10～30% of the substituted oil of mirbane quality of X that adds; The nickel catalyst carried amount that adds is 3～6% of the substituted oil of mirbane quality of X that adds; Carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, and reaction is carried out solid-liquid separation after accomplishing; Separated liquid supernatant is carried out the product separation, and isolated solid is failed back reaction system again and continued to use; Described nickel catalyst carried preparation method is: nickel is processed nitrate salt earlier; Be mixed with the aqueous solution of 1M again; The amount of getting nickel is 45～58% a nickel salt aqueous solution of catalyzer final product quality, adds the silica aqueous solution that contains silicon-dioxide 20% again, and the amount of the silica aqueous solution that is added should guarantee to make silica volume wherein to account for 1～4% of catalyzer final product quality; System is heated to 50～80 ℃; Under agitation condition, add 35～55% the zeyssatite of handling through acid cleaning process of catalyzer final product quality, the pH value with system transfers to 7.5～8.5 again, under 50～80 ℃ of conditions, stirs 12～16 hours; Carry out solid-liquid separation after the cooling; Resulting solid is handled with the laggard capable granulating and drying of water washing, uses hydrogen reduction at 500～700 ℃, under cooling conditions, carries out obtaining the catalyzer finished product after the Passivation Treatment with the Air mixing inert gas that contains volume ratio 5% again.
2. the substituted oil of mirbane shortening of X according to claim 1 prepares the method for the substituted aniline of X, it is characterized in that changing reaction mass over to the insulation jar after reaction is accomplished is incubated sedimentation, isolates supernatant and carries out the product separation, obtains the substituted aniline of X; The interior aforementioned quantities of pressing of reaction kettle adds new substituted oil of mirbane of X and ethanol, will from the insulation jar, fail back reaction kettle continuation use again by isolated bottom solidliquid mixture simultaneously.
3. the substituted oil of mirbane shortening of X according to claim 1 and 2 prepares the method for the substituted aniline of X; It is characterized in that the supported catalyst dosage that adds is 4% of the substituted oil of mirbane quality of X; Temperature of reaction is 90 ℃, and the still internal pressure during hydrogenation is 1.5MPa.
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| CN103333072B (en) * | 2013-07-16 | 2015-02-04 | 如皋市众昌化工有限公司 | Preparation method of 2-ethylaniline |
| CN103351303B (en) * | 2013-07-17 | 2015-05-20 | 临邑县鲁晶化工有限公司 | Continuation method of manufacturing o-Aminoethylbenzene through hydrogenation by o-Nitroethylbenzene |
| CN107118109A (en) * | 2017-06-14 | 2017-09-01 | 浙江解氏新材料股份有限公司 | The preparation method of adjacent fluoroaniline |
| CN116023271B (en) * | 2023-01-13 | 2023-06-20 | 山东国邦药业有限公司 | Synthesis method of p-fluoroaniline |
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| CN101081818A (en) * | 2007-06-18 | 2007-12-05 | 大连理工大学 | Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101081818A (en) * | 2007-06-18 | 2007-12-05 | 大连理工大学 | Preparation method for methoxyaniline by highly-selective catalytic hydrogenation of methoxyl nitro compound |
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