CN112479900A - Method for synthesizing 2,5-dichloroaniline through kettle type continuous hydrogenation - Google Patents
Method for synthesizing 2,5-dichloroaniline through kettle type continuous hydrogenation Download PDFInfo
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- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 239000007788 liquid Substances 0.000 claims abstract description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000009826 distribution Methods 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 230000010757 Reduction Activity Effects 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract 2
- 239000007789 gas Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a kettle type continuous hydrogenation method for synthesizing 2,5-dichloroaniline, which comprises a feeding pump, a preheater, a reactor, a gas-liquid separator and a recovery pump, wherein the feeding pump, the preheater, the reactor, the gas-liquid separator and the recovery pump are sequentially connected in series, a plurality of hydrogen distribution pipes are arranged in the reactor, a plurality of through holes are formed in the side surfaces of the hydrogen distribution pipes, and catalysts are arranged in the hydrogen distribution pipes; the method for synthesizing 2,5-dichloroaniline by kettle type continuous hydrogenation comprises the following steps: inputting the 2, 5-dichloronitrobenzene solution into a reactor through a feed pump, inputting hydrogen into the reactor, and reacting the hydrogen with the 2, 5-dichloronitrobenzene solution to generate 2,5-dichloroaniline after the hydrogen is adsorbed by a catalyst; the method adopts the catalyst with high nitro reduction activity, has few byproducts, and can realize the high-efficiency conversion of the raw materials only at the reaction temperature of 50-80 ℃. The method is adopted for continuous reaction for 720 hours, the conversion rate of raw materials is more than 95 percent, and the product selectivity is more than 95 percent.
Description
Technical Field
The invention relates to the field of compound synthesis, in particular to a kettle-type continuous hydrogenation method for synthesizing 2, 5-dichloroaniline.
Background
2,5-dichloroaniline of formula C6H5Cl2N, English name is 2,5-DichloroAniline, can be used as synthetic intermediate raw material of herbicide dicamba, can also be used for manufacturing nitrogen fertilizer synergist, can be directly used as scarlet base GG dye and printing and dyeing developer, and can be used as improved dye intermediate raw material on the basis. Is a relatively important chemical raw material.
The reduction of nitro group is commonly carried out by iron powder reduction method, sodium dithionite method, noble metal catalytic hydrogenation method, hydrazine hydrate method, etc., wherein the iron powder reduction method is most widely used, but the operation is complex, the occupied space of the equipment is large, the pollution of waste water and waste residue generated by reaction is large, and the post-treatment is troublesome. At present, noble metal catalytic hydrogenation methods are concerned with low energy consumption, cleaner three-waste treatment methods and higher utilization rate, wherein the more commonly used metal catalysts comprise Raney Ni, Pd/C, Pt/C, Ru/C and the like. However, the noble metal catalytic hydrogenation method is currently commonly used as an intermittent reaction kettle, the operation is still complicated, and the potential safety hazard is large.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, provides a method for synthesizing 2,5-dichloroaniline by kettle-type continuous hydrogenation, aims to solve the problems of complex operation, difficult three-waste treatment and the like in the prior art, and can realize continuous and efficient synthesis of 2,5-dichloroaniline by adopting a continuous hydrogenation reaction process compared with a batch reaction process.
In order to solve the technical problems, the invention adopts the technical scheme that: the method for synthesizing 2,5-dichloroaniline through kettle type continuous hydrogenation is characterized by comprising a feeding pump, a preheater, a reactor, a gas-liquid separator and an extraction pump, wherein the feeding pump, the preheater, the reactor, the gas-liquid separator and the extraction pump are sequentially connected in series, a plurality of hydrogen distribution pipes are arranged in the reactor, a plurality of through holes are formed in the side surfaces of the hydrogen distribution pipes, and catalysts are arranged in the hydrogen distribution pipes; the method for synthesizing 2,5-dichloroaniline by kettle type continuous hydrogenation comprises the following steps: inputting the 2, 5-dichloronitrobenzene solution into a reactor through a feed pump, inputting hydrogen into the reactor, and reacting the hydrogen with the 2, 5-dichloronitrobenzene solution to generate 2,5-dichloroaniline after the hydrogen is adsorbed by a catalyst;
the concentration of the 2, 5-dichloronitrobenzene solution is 0.5-2.0 mol/L, and the catalyst is one or more of Raney Ni and Pd/C, Pt/C, Ru/C.
Furthermore, in the catalyst, the total mass of the noble metals accounts for 5.0-20.0% of the mass of the catalyst.
Further, the metal carrier of the catalyst is activated carbon; the specific surface area of the catalyst is 50-250 m2The pore volume of the catalyst is 1.5-2.8 mL/g.
Further, the solvent in the 2, 5-dichloronitrobenzene solution is one or more of tetrahydrofuran, methanol and ethanol.
Further, the reaction temperature of the hydrogen and the 2, 5-dichloronitrobenzene solution is 40-10 ℃, and the hydrogen pressure in the reactor is 0.1-3.0 MPa in the reaction process.
Further, the feeding volume airspeed of the 2, 5-dichloronitrobenzene solution is 1.0-2.5 h-1The volume ratio of the hydrogen gas inflow to the feed liquid of the raw material liquid is 100-1200: 1.
compared with the prior art, the invention has the beneficial effects that: by adopting the catalyst with high nitro reduction activity, the by-products are few, and the high-efficiency conversion of the raw materials can be realized only at the reaction temperature of 50-80 ℃. The method has the advantages of continuous reaction for 720 hours, conversion rate of raw materials of more than 95 percent, product selectivity of more than 95 percent, continuous preparation of 2, 5-diaminoaniline, effective saving of reaction time and reduction of space occupied by equipment.
Drawings
The disclosure of the present invention is illustrated with reference to the accompanying drawings. It is to be understood that the drawings are designed solely for the purposes of illustration and not as a definition of the limits of the invention. In the drawings, like reference numerals are used to refer to like parts. Wherein:
FIG. 1 is a schematic view of the structure of a reaction apparatus of the present invention.
FIG. 2 is a reaction scheme of example 1 of the present invention.
FIG. 3 is a reaction scheme of example 2 of the present invention.
FIG. 4 is a reaction scheme of example 3 of the present invention.
FIG. 5 is a reaction scheme of example 4 of the present invention.
FIG. 6 is a reaction scheme of example 5 of the present invention.
Reference numbers in the figures: 1-feeding pump, 2-preheater, 3-reactor, 4-gas-liquid separator and 5-extraction pump.
Detailed Description
It is easily understood that according to the technical solution of the present invention, a person skilled in the art can propose various alternative structures and implementation ways without changing the spirit of the present invention. Therefore, the following detailed description and the accompanying drawings are merely illustrative of the technical aspects of the present invention, and should not be construed as all of the present invention or as limitations or limitations on the technical aspects of the present invention.
A method for synthesizing 2,5-dichloroaniline through kettle-type continuous hydrogenation relates to equipment for synthesizing 2,5-dichloroaniline through kettle-type continuous hydrogenation, and comprises a feeding pump, a preheater, a reactor, a gas-liquid separator and an extraction pump, wherein the feeding pump, the preheater, the reactor, the gas-liquid separator and the extraction pump are sequentially connected in series, a plurality of hydrogen distribution pipes are arranged in the reactor, a plurality of holes are formed in the side faces of the hydrogen distribution pipes, a catalyst is arranged in the hydrogen distribution pipes, hydrogen and the top of the reactor are introduced into the reactor, and the hydrogen is adsorbed onto the catalyst due to the existence of the catalyst. The raw material liquid, namely the 2, 5-dichloronitrobenzene solution with the concentration of 0.5-2.0 mol/L, is output from a feed pump, heated by a preheater and then input into a reactor to react with hydrogen adsorbed on a catalyst to generate 2,5-dichloroaniline, and the incompletely reacted hydrogen can be recovered from a gas-liquid separator.
The technical solution of the present invention is further described in detail with reference to the accompanying drawings and examples.
Example 1
Dissolving 10kg of 2, 5-dichloronitrobenzene in 26L of anhydrous methanol solution to prepare feed liquid with the concentration of 2.0mol/L, introducing the feed liquid into a heat exchanger, heating to 70 ℃, feeding the feed liquid into a reaction kettle, placing 10% Pd/C in a hydrogen distribution pipe in the reaction kettle, introducing high-purity hydrogen until the hydrogen pressure in the reaction kettle reaches 1.0MPa, injecting the feed liquid from the side surface of the reaction kettle through a pipeline, and ensuring that the feeding volume airspeed is 1.0h-1Hydrogen enters from the upper end of the reaction kettle through a pipeline, and the volume ratio of the hydrogen entering volume to the feed liquid entering volume is 1200: 1. the mixed liquid obtained by the reaction enters a separator for gas-liquid separation, unreacted gas is purified and then is reused, and the obtained product is analyzed by HPLC, so that the conversion rate of the obtained 2, 5-dichloronitrobenzene is 96.3 percent, and the selectivity of the 2,5-dichloroaniline is 97.2 percent.
Example 2
Dissolving 10kg of 2, 5-dichloronitrobenzene in 35L of ethanol solution to prepare feed liquid with the concentration of 1.5mol/L, introducing the feed liquid into a heat exchanger, heating the feed liquid to 60 ℃, feeding the feed liquid into a reaction kettle, placing 15% Raney Ni in a hydrogen distribution pipe in the reaction kettle, introducing high-purity hydrogen until the hydrogen pressure in the reaction kettle reaches 2.0MPa, injecting the feed liquid from the side surface of the reaction kettle through a pipeline, wherein the feeding volume airspeed is 1.2h-1Hydrogen enters from the upper end of the reaction kettle through a pipeline, and the volume ratio of the hydrogen entering volume to the feed liquid entering volume is 150: 1. the mixed liquid obtained by the reaction enters a separator for gas-liquid separation, unreacted gas is purified and then is reused, and the obtained product is analyzed by HPLC, so that the conversion rate of the obtained 2, 5-dichloronitrobenzene is 92.2 percent, and the selectivity of the 2,5-dichloroaniline is 95.9 percent.
Example 3
Dissolving 10kg of 2, 5-dichloronitrobenzene in 35L of anhydrous tetrahydrofuran solution to prepare feed liquid with the concentration of 1.5mol/L, introducing the feed liquid into a heat exchanger, heating to 65 ℃, feeding the feed liquid into a reaction kettle, placing 10% Ru/C in a hydrogen distribution pipe in the reaction kettle, introducing high-purity hydrogen until the hydrogen pressure in the reaction kettle reaches 1.5MPa, injecting the feed liquid from the side surface of the reaction kettle through a pipeline, wherein the feeding volume airspeed is 1.0h-1Hydrogen enters from the upper end of the reaction kettle through a pipeline, and the volume ratio of the hydrogen entering volume to the feed liquid entering volume is 1200: 1. the mixed liquid obtained by the reaction enters a separator for gas-liquid separation, and the unreacted gas is purifiedAnd then the obtained product is reused, and the conversion rate of the obtained 2, 5-dichloronitrobenzene is 94.3 percent and the selectivity of the 2,5-dichloroaniline is 95.2 percent by HPLC analysis.
Example 4
10kg of 2, 5-dichloronitrobenzene is dissolved in 26L of anhydrous methanol solution to prepare feed liquid with the concentration of 2.0mol/L, the feed liquid is introduced into a heat exchanger to be heated to 70 ℃ and fed into a reaction kettle, 20 percent Pd/C is placed in a hydrogen distribution pipe in the reaction kettle, high-purity hydrogen is introduced until the hydrogen pressure in the reaction kettle reaches 2.0MPa, the feed liquid is injected from the side surface of the reaction kettle through a pipeline, and the feeding volume airspeed is 1.2h-1Hydrogen enters from the upper end of the reaction kettle through a pipeline, and the volume ratio of the entering volume of the hydrogen to the entering volume of the feed liquid is 250: 1. the mixed liquid obtained by the reaction enters a separator for gas-liquid separation, unreacted gas is purified and then is reused, and the obtained product is analyzed by HPLC, so that the conversion rate of the obtained 2, 5-dichloronitrobenzene is 99.6 percent, and the selectivity of the 2,5-dichloroaniline is 97.2 percent.
Example 5
Dissolving 10kg of 2, 5-dichloronitrobenzene in 52L of anhydrous methanol solution to prepare feed liquid with the concentration of 1.0mol/L, introducing the feed liquid into a heat exchanger, heating the feed liquid to 75 ℃, feeding the feed liquid into a reaction kettle, placing 15% Raney Ni in a hydrogen distribution pipe in the reaction kettle, introducing high-purity hydrogen until the hydrogen pressure in the reaction kettle reaches 2.0MPa, injecting the feed liquid from the side surface of the reaction kettle through a pipeline, wherein the feeding volume airspeed is 2.0h-1Hydrogen enters from the upper end of the reaction kettle through a pipeline, and the volume ratio of the hydrogen entering volume to the feed liquid entering volume is 150: 1. the mixed liquid obtained by the reaction enters a separator for gas-liquid separation, unreacted gas is purified and then is reused, and the obtained product is analyzed by HPLC, so that the conversion rate of the obtained 2, 5-dichloronitrobenzene is 93.7 percent, and the selectivity of the 2,5-dichloroaniline is 98.4 percent.
In the above embodiment, the hydrogen distribution pipe may be replaced with a hollow interlayer disposed in the reactor, the inner wall of the hollow interlayer is provided with through holes, and the interlayer is provided with a catalyst for adsorbing hydrogen. In the embodiment, the percentage content before the catalyst is the proportion of the total mass of the noble metals in the catalyst to the mass of the catalyst, namely the content of nickel in Raney Ni, the content of Pd in Pd/C, the content of Pt in Pt/C and the content of Ru in Ru/C, in the embodiment, any one of Raney Ni and Pd/C, Pt/C, Ru/C is adopted as the catalyst for use, and a plurality of catalysts can be compounded, and because the actions of the catalysts are all to adsorb hydrogen and accelerate the reaction progress, the synthesis result of the application is not influenced by adopting one or more catalysts.
The technical scope of the present invention is not limited to the above description, and those skilled in the art can make various changes and modifications to the above-described embodiments without departing from the technical spirit of the present invention, and such changes and modifications should fall within the protective scope of the present invention.
Claims (6)
1. The method for synthesizing 2,5-dichloroaniline through kettle type continuous hydrogenation is characterized by comprising a feeding pump, a preheater, a reactor, a gas-liquid separator and an extraction pump, wherein the feeding pump, the preheater, the reactor, the gas-liquid separator and the extraction pump are sequentially connected in series, a plurality of hydrogen distribution pipes are arranged in the reactor, a plurality of through holes are formed in the side surfaces of the hydrogen distribution pipes, and catalysts are arranged in the hydrogen distribution pipes; the method for synthesizing 2,5-dichloroaniline by kettle type continuous hydrogenation comprises the following steps: inputting the 2, 5-dichloronitrobenzene solution into a reactor through a feed pump, inputting hydrogen into the reactor, and reacting the hydrogen with the 2, 5-dichloronitrobenzene solution to generate 2,5-dichloroaniline after the hydrogen is adsorbed by a catalyst;
the concentration of the 2, 5-dichloronitrobenzene solution is 0.5-2.0 mol/L, and the catalyst is one or more of Raney Ni and Pd/C, Pt/C, Ru/C.
2. The kettle-type continuous hydrogenation method for synthesizing 2,5-dichloroaniline according to claim 1, wherein the total mass of noble metals in the catalyst accounts for 5.0-20.0% of the mass of the catalyst.
3. The kettle-type continuous hydrogenation method for synthesizing 2,5-dichloroaniline according to claim 1, wherein the metal carrier of the catalyst is activated carbon; the specific surface area of the catalyst is 50-250 m2The pore volume of the catalyst is 1.5-2.8 mL/g.
4. The method for synthesizing 2,5-dichloroaniline through kettle-type continuous hydrogenation according to claim 1, wherein the solvent in the 2, 5-dichloronitrobenzene solution is one or more of tetrahydrofuran, methanol and ethanol.
5. The kettle-type continuous hydrogenation method for synthesizing 2,5-dichloroaniline according to claim 1, wherein the reaction temperature of the hydrogen and the 2, 5-dichloronitrobenzene solution is 40-10 ℃, and the hydrogen pressure in the reactor during the reaction process is 0.1-3.0 MPa.
6. The kettle-type continuous hydrogenation method for synthesizing 2,5-dichloroaniline according to claim 1, wherein the feeding volume space velocity of the 2, 5-dichloronitrobenzene solution is 1.0-2.5 h-1The volume ratio of the hydrogen gas inflow to the feed liquid of the raw material liquid is 100-1200: 1.
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| CN114307862A (en) * | 2021-12-01 | 2022-04-12 | 中海油天津化工研究设计院有限公司 | Method for preparing methyl substituted aniline through membrane dispersion hydrogenation |
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| CN114307862A (en) * | 2021-12-01 | 2022-04-12 | 中海油天津化工研究设计院有限公司 | Method for preparing methyl substituted aniline through membrane dispersion hydrogenation |
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