CN101475488A - Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene - Google Patents
Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene Download PDFInfo
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- CN101475488A CN101475488A CNA2008101742041A CN200810174204A CN101475488A CN 101475488 A CN101475488 A CN 101475488A CN A2008101742041 A CNA2008101742041 A CN A2008101742041A CN 200810174204 A CN200810174204 A CN 200810174204A CN 101475488 A CN101475488 A CN 101475488A
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Abstract
The invention discloses a method for preparing corresponding diaminotoluene through catalytic hydrogenation of 2,4-dinitrotoluene or 2,6-dinitrotoluene or a mixture of the 2,4-dinitrotoluene and the 2,6-dinitrotoluene. The method for preparing the diaminotoluene through catalytic hydrogenation of the 2,4-dinitrotoluene comprises: respectively adding the 2,4-dinitrotoluene or the 2,6-dinitrotoluene or the mixture of the 2,4-dinitrotoluene and the 2,6-dinitrotoluene, and ethanol and a supported catalyst into a reaction kettle first; performing hydrogenation reaction for 3 to 8 hours at a temperature of between 60 and 90 DEG C, wherein the pressure of the hydrogenation reaction is between 1.5 and 3.0 MPa; and performing solid-liquid separation after the reaction is over, using separated supernatant for product separation, and conveying a separated solid catalyst back to a reaction system for continuous use.
Description
Technical field
The present invention relates to 2,4-dinitrotoluene (DNT) or 2,6-dinitrotoluene (DNT) or 2,4-dinitrotoluene (DNT) and 2, the method for the corresponding diaminotoluene of mixture through catalytic hydrogenation preparing of 6-dinitrotoluene (DNT).
Background technology
Nitro-compound is by being reduced to aminocompound, be method preparation the earliest by iron powder and hydrochloric acid, this method is seriously polluted, expressly provide the operational path that to abolish at no distant date for country, most of in recent years this type of produced and all adopted Raney's nickel catalyst, promptly be that catalyzer realizes having following shortcoming by the conversion of nitro to amino but use Raney's nickel catalyst to carry out shortening by 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 as commodity with nickel-Al alloy powder form, need before the use aluminium to be dissolved away, under the condition of secluding air, add reaction system behind the wash clean with alkali; In addition, the catalytic activity of Raney's nickel often because of treatment condition (as alkali molten with wash conditions) different changing a lot.
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 being higher than the easy by product (the industrial tar that is referred to as) that generates under 100 ℃ of temperature, this makes product yield reduce on the one hand, also may 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 easily catches 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 invention provides a kind of prior art deficiency that overcomes, usefulness 2 with higher-security and higher yields, 4-dinitrotoluene (DNT) or 2,6-dinitrotoluene (DNT) or 2,4-dinitrotoluene (DNT) and 2, the method for the corresponding diaminotoluene of mixture through catalytic hydrogenation preparing of 6-dinitrotoluene (DNT).
Among the present invention, with 2,4-dinitrotoluene (DNT) shortening preparation 2, the method of 4-diaminotoluene is: add 2 respectively earlier in reactor, the 4-dinitrotoluene (DNT), ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 2 of adding, 10～30% of 4-dinitrotoluene (DNT) quality, the nickel catalyst carried amount that adds is 2 of adding, and 3～6% of 4-dinitrotoluene (DNT) quality was carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, carry out solid-liquid separation after reaction is finished, separated liquid supernatant is carried out the product separation, and isolated solid catalyst is failed back reaction system again and continued to use.
Among the present invention, with 2, the method that 4-dinitrotoluene (DNT) shortening prepares 2,4 di amino toluene can also be to change reaction mass over to the insulation jar to be incubated sedimentation after reaction is finished, and isolates supernatant liquor and carries out the product separation, obtains 2,4 di amino toluene; Add in the reactor newly 2 by aforementioned quantities, 4-dinitrotoluene (DNT) and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture (catalyzer and a small amount of post reaction mixture) the insulation jar simultaneously.
Among the present invention, with 2, the method that 4-dinitrotoluene (DNT) shortening prepares 2,4 di amino toluene can also be that the supported catalyst dosage that adds is 2,4% of 4-dinitrotoluene (DNT) quality, and temperature of reaction is 90 ℃, the still internal pressure during hydrogenation is 1.5MPa.
Among the present invention, with 2,6-dinitrotoluene (DNT) shortening preparation 2, the method of 6-diaminotoluene is: add 2 respectively earlier in reactor, the 6-dinitrotoluene (DNT), ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 2 of adding, 10～30% of 4-nitrotoluene quality, the nickel catalyst carried amount that adds is 2 of adding, and 3～6% of 6-nitrotoluene quality was carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, carry out solid-liquid separation after reaction is finished, separated liquid supernatant is carried out the product separation, and isolated solid catalyst is failed back reaction system again and continued to use.
Among the present invention, with 2,6-dinitrotoluene (DNT) shortening preparation 2, the method of 6-diaminotoluene can also be to change reaction mass over to the insulation jar in the reactor to be incubated sedimentation after reaction is finished, isolate supernatant liquor and carry out the product separation, obtain 2, the 6-diaminotoluene; Add in the reactor newly 2 by aforementioned quantities, 6-dinitrotoluene (DNT) and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture (catalyzer and a small amount of post reaction mixture) the insulation jar simultaneously.
Among the present invention, with 2,6-dinitrotoluene (DNT) shortening preparation 2, the method for 6-diaminotoluene can also be that the supported catalyst dosage that adds is 2,4% of 6-dinitrotoluene (DNT) quality, temperature of reaction is 90 ℃, the still internal pressure during hydrogenation is 1.5MPa.
Among the present invention, with 2,4-dinitrotoluene (DNT) and 2, the method of the mixture through catalytic hydrogenation preparing diaminotoluene of 6-dinitrotoluene (DNT), it is characterized in that in reactor, adding 2 of the ratio that requires, 4-dinitrotoluene (DNT) and 2,6-dinitrotoluene (DNT) mixture, ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 10～30% of the nitrotoluene mixture total mass that adds, the nickel catalyst carried amount that adds is 3～6% of the nitrotoluene mixture total mass that adds, carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, carry out solid-liquid separation after reaction is finished, separated liquid supernatant is carried out the product separation, and isolated solid catalyst is failed back reaction system again and continued to use.
Among the present invention, with 2,4-dinitrotoluene (DNT) and 2, the method of the mixture through catalytic hydrogenation preparing diaminotoluene of 6-dinitrotoluene (DNT) can be to change reaction mass over to the insulation jar to be incubated sedimentation after reaction is finished, isolate supernatant liquor and carry out the product separation, obtain 2,4 di amino toluene and 2, the mixture of 6-diaminotoluene; Add by aforementioned quantities in the reactor new 2,4-dinitrotoluene (DNT) and 2,6-dinitrotoluene (DNT) mixture and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture (catalyzer and a small amount of post reaction mixture) the insulation jar simultaneously.
Among the present invention, with 2,4-dinitrotoluene (DNT) and 2, the method for the mixture through catalytic hydrogenation preparing diaminotoluene of 6-dinitrotoluene (DNT) can be that the supported catalyst dosage that adds is 4% of nitrotoluene mixture total mass, 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 has carried out purification process with the blended inert gas, make its part be in passive state, therefore 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 nitro-compound hydrogenation catalysts.Because catalyst temperature of reaction of the present invention is less than 100 ℃, therefore can avoid in reactant, generating polymers such as tar fully, 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 chat embodiment as seen, hydrogenation pressure only is 1.5MPa in its optimised process, this pressure obviously will be lower than prior art.In addition, from the present invention as seen, this method can also be simplified whole production technique.
Embodiment
Embodiment 1:2,4-dinitrotoluene (DNT) shortening prepares 2,4 di amino toluene
In reactor, add 2 of 100 grams earlier, the 4-dinitrotoluene (DNT), add 2 again, 20% concentration of 4-dinitrotoluene (DNT) quality is 95% ethanol, add 2 again, the loaded catalyst of 4-dinitrotoluene (DNT) quality 3～6%, closed reactor, with the air in the complete replacement reaction kettle of hydrogen, keep 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 reactor 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 40 milligrams; To reaction mixture, promptly clear liquid carries out the reaction product separation, obtains 2, about 64～67 grams of 4-phenylmethylamine.In the present invention, the concrete grammar that is adopted is earlier reaction system to be changed in the insulation slurry tank, carries out separating of catalyzer and reaction mixture by settled way.
Test shows that in above-mentioned reaction process, the supported catalyst dosage of adding is 2 of adding, and 4% of 4-dinitrotoluene (DNT) quality, the still internal pressure during hydrogenation are 1.5Mpa, and when temperature of reaction was 90 ℃, transformation efficiency promptly reached more than 99.0% in 4 hours.
Embodiment 2:2,6-dinitrotoluene (DNT) shortening preparation 2,6-diaminotoluene
In reactor, add 2 of 100 grams earlier, the 6-dinitrotoluene (DNT), add 2 again, 20% concentration of 6-dinitrotoluene (DNT) quality is 95% ethanol, add 2 again, the loaded catalyst of 6-dinitrotoluene (DNT) quality 3～6%, closed reactor, with the air in the complete replacement reaction kettle of hydrogen, keep 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 reactor 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 40 milligrams; To reaction mixture, promptly clear liquid carries out the reaction product separation, obtains 2,6-diaminotoluene 64～67 grams.In the present invention, the concrete grammar that is adopted is earlier reaction system to be changed over to sedimentation in the insulation slurry tank to carry out separating of catalyzer and reaction mixture.
Test shows that in above-mentioned reaction process, the supported catalyst dosage of adding is 2 of adding, and 4% of 6-dinitrotoluene (DNT) quality, the still internal pressure during hydrogenation are 1.5MPa, and when temperature of reaction was 90 ℃, transformation efficiency promptly reached more than 99.0% in 4 hours.
Embodiment 3:2,4-dinitrotoluene (DNT) and 2, the corresponding diaminotoluene of mixture through catalytic hydrogenation preparing of 6-dinitrotoluene (DNT)
Ratio as requested adds 2 of 100 grams in reactor, 4-dinitrotoluene (DNT) and 2, the mixture of 6-dinitrotoluene (DNT), wherein 2,4-dinitrotoluene (DNT) and 2, the ratio of 6-dinitrotoluene (DNT) is 4: 1 (mass ratio), 20% the concentration that adds the nitrotoluene mixture quality again is 95% ethanol, the loaded catalyst that adds dinitrotoluene (DNT) mixture quality 3～6% again, closed reactor, with the air in the complete replacement reaction kettle of hydrogen, keep being in the still normal pressure (being about 0.1MPa) then, and 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 reactor to be continued to use, the catalyzer of replenish loss amount, test show that the catalytic amount that at every turn only need add is about 40 milligrams; To reaction mixture, promptly clear liquid carries out the reaction product separation, obtains 2,4 di amino toluene and 2, about 64～67 grams of the mixture of 6-diaminotoluene.In the present invention, the concrete grammar that is adopted is earlier reaction system to be changed over to sedimentation in the insulation slurry tank to carry out separating of catalyzer and reaction mixture.
Test shows, in above-mentioned reaction process, the supported catalyst dosage of adding is 4% of the nitrotoluene mixture quality that adds, and the still internal pressure during hydrogenation is 1.5MPa, and when temperature of reaction was 90 ℃, transformation efficiency promptly reached more than 99.0% in 4 hours.
The used supported catalyst preparation method of the present invention following (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 " about loaded catalyst of the present invention) referring to name:
The diatomaceous processing of A
Find according to experiment, very big as the impurity in the diatomite of carrier to the influence of catalyzer, and wherein with the influence of iron for, for effectively removing the iron in the diatomite, generally all adopt acid cleaning process, but find according to relevant test, diatomite is handled and has been adopted following technology that best effect can be arranged, it not only can effectively remove wherein impurity, particularly iron, but also can make catalyst product that best catalytic effect is arranged:
Earlier diatomite is added volume ratio and be its 3 times, concentration is to stir in 3～20% the aqueous hydrochloric acid, continues stirring 1 hour after being warmed up to 90 ℃ again, leach diatomite and wash with water after carry out drying treatment, obtain diatomite as support of the catalyst.
Show after testing, handle resulting diatomite 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 diatomite is handled used best aqueous hydrochloric acid concentration.
The B Preparation of catalysts
Nickel is made nitrate 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, system is heated to 50～80 ℃, 35～55% of adding catalyzer final product quality diatomite 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, carrying out granulating and drying after resulting solid washes with water handles, 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 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 as follows:
(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 40～200
(optimum value is 60
);
(6) catch fire in the air 170 ℃ of warm spots
(7) reduction ratio (NiO/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 | The Germany Louis product 6504K of that company | The product 0104G of U.S. An Geer company | |
| 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 °) | ≥150 | ≥150 | ≥150 |
| The hydrogenation catalyst starting temperature | ≥60 | ≥90 | ≥90 |
Claims (9)
1,2,4-dinitrotoluene (DNT) shortening prepares the method for corresponding phenylmethylamine, it is characterized in that in reactor, adding 2 respectively, the 4-dinitrotoluene (DNT), ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 2 of adding, 10～30% of 4-dinitrotoluene (DNT) quality, the nickel catalyst carried amount that adds is 2 of adding, 3～6% of 4-dinitrotoluene (DNT) quality, carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, carries out solid-liquid separation after reaction is finished, separated liquid supernatant is carried out the product separation, and isolated solid is failed back reaction system again and continued to use.
2, according to claim 12,4-dinitrotoluene (DNT) shortening prepares the method for corresponding phenylmethylamine, it is characterized in that changing reaction mass over to the insulation jar after reaction is finished is incubated sedimentation, isolates supernatant liquor and carries out the product separation, obtain 2,4 di amino toluene; Add in the reactor newly 2 by aforementioned quantities, 4-dinitrotoluene (DNT) and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture the insulation jar simultaneously.
3, according to claim 1 and 22,4-dinitrotoluene (DNT) shortening prepares the method for corresponding phenylmethylamine, it is characterized in that the supported catalyst dosage that adds is 2,4% of 4-dinitrotoluene (DNT) quality, temperature of reaction is 90 ℃, and the still internal pressure during hydrogenation is 1.5MPa.
4,2, the method of 6-dinitrotoluene (DNT) preparing aminotoluene by catalytic hydrogenation, it is characterized in that in reactor, adding 2 respectively, the 6-dinitrotoluene (DNT), ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 2 of adding, 10～30% of 4-nitrotoluene quality, the nickel catalyst carried amount that adds is 2 of adding, 3～6% of 6-nitrotoluene quality, carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, carries out solid-liquid separation after reaction is finished, separated liquid supernatant is carried out the product separation, and isolated solid is failed back reaction system again and continued to use.
5, according to claim 32, the method of 6-dinitrotoluene (DNT) preparing aminotoluene by catalytic hydrogenation is characterized in that changing reaction mass over to insulation in the reactor after reaction is finished jar is incubated sedimentation, isolates supernatant liquor and carries out product and separate, obtain 2, the 6-diaminotoluene; Add in the reactor newly 2 by aforementioned quantities, 6-dinitrotoluene (DNT) and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture the insulation jar simultaneously.
6, according to claim 4 or 5 described 2, the method of 6-dinitrotoluene (DNT) preparing aminotoluene by catalytic hydrogenation is characterized in that the supported catalyst dosage that adds is 2,4% of 4-dinitrotoluene (DNT) quality, still internal pressure during hydrogenation is 1.5MPa, and temperature of reaction is 90 ℃.
7,2,4-dinitrotoluene (DNT) and 2, the method of 6-dinitrotoluene (DNT) preparing aminotoluene by catalytic hydrogenation, it is characterized in that in reactor, adding 2 of the ratio that requires, 4-dinitrotoluene (DNT) and 2,6-dinitrotoluene (DNT) mixture and ethanol and loaded catalyst, wherein the amount of alcohol of Jia Ruing is 10～30% of the nitrotoluene mixture total mass that adds, the nickel catalyst carried amount that adds is 3～6% of the nitrotoluene mixture total mass that adds, carried out hydrogenation reaction 3～8 hours at 60～90 ℃, hydrogenation reaction pressure is 1.5～3.0MPa, after finishing, reaction carries out solid-liquid separation, separated liquid supernatant is carried out the product separation, and isolated solid is failed back reaction system again and continued to use.
8, according to claim 72,4-dinitrotoluene (DNT) and 2, the method of 6-dinitrotoluene (DNT) mixture through catalytic hydrogenation preparing phenylmethylamine, it is characterized in that changing reaction mass over to the insulation jar after reaction is finished is incubated sedimentation, isolate supernatant liquor and carry out the product separation, obtain 2,4 di amino toluene and 2, the mixture of 6-diaminotoluene; Add by aforementioned quantities in the reactor new 2,4-dinitrotoluene (DNT) and 2,6-dinitrotoluene (DNT) and ethanol will fail back reactor continuation use again from isolated bottom solidliquid mixture the insulation jar simultaneously.
9, according to claim 7 or 8 described 2,4-dinitrotoluene (DNT) and 2, the method of 6-dinitrotoluene (DNT) mixture through catalytic hydrogenation preparing phenylmethylamine, it is characterized in that the supported catalyst dosage that adds is 4% of nitrotoluene mixture total mass, still internal pressure during hydrogenation is 1.5MPa, and temperature of reaction is 90 ℃.
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| CN200810174204.1A CN101475488B (en) | 2008-11-07 | 2008-11-07 | Method for preparing aminotoluene by catalytic hydrogenation of 2,4-dinitrotoluene or/and 2,6-dinitrotoluene |
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| CN201410060118.3A Division CN104193624A (en) | 2008-11-07 | 2008-11-07 | Method of preparing aminotoluene by subjecting 2,4-dinitrotoluene and 2,6-dinitrotoluene to catalytic hydrogenation |
| CN201410043464.0A Division CN103804202A (en) | 2008-11-07 | 2008-11-07 | Method for preparing diaminotoluene through catalytic hydrogenation |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102580748A (en) * | 2011-12-20 | 2012-07-18 | 太原理工大学 | Amorphous alloy catalyst for hydrogenating dinitrotoluene and application of amorphous alloy catalyst |
| CN103772208A (en) * | 2014-01-22 | 2014-05-07 | 淮安嘉诚高新化工股份有限公司 | Treatment method of residues from nitrotoluene rectification kettle |
| CN104140371A (en) * | 2014-07-10 | 2014-11-12 | 四川北方红光特种化工有限公司 | Preparation method of high-purity 2,6-diaminotoluene |
| CN113563213A (en) * | 2021-08-30 | 2021-10-29 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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2008
- 2008-11-07 CN CN200810174204.1A patent/CN101475488B/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102580748A (en) * | 2011-12-20 | 2012-07-18 | 太原理工大学 | Amorphous alloy catalyst for hydrogenating dinitrotoluene and application of amorphous alloy catalyst |
| CN102580748B (en) * | 2011-12-20 | 2014-05-28 | 太原理工大学 | Amorphous alloy catalyst for hydrogenating dinitrotoluene and application of amorphous alloy catalyst |
| CN103772208A (en) * | 2014-01-22 | 2014-05-07 | 淮安嘉诚高新化工股份有限公司 | Treatment method of residues from nitrotoluene rectification kettle |
| CN104140371A (en) * | 2014-07-10 | 2014-11-12 | 四川北方红光特种化工有限公司 | Preparation method of high-purity 2,6-diaminotoluene |
| CN104140371B (en) * | 2014-07-10 | 2015-12-09 | 四川北方红光特种化工有限公司 | The preparation method of high purity 2,6-diaminotoluene |
| CN113563213A (en) * | 2021-08-30 | 2021-10-29 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
| CN113563213B (en) * | 2021-08-30 | 2024-03-22 | 淄博晟亿弘新材料科技有限公司 | Preparation method of 3, 5-diaminobenzoic acid |
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| CN101475488B (en) | 2014-06-18 |
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