CN110862323A - Synthesis method of diaminodiphenylethane compound - Google Patents
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- 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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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Abstract
The invention discloses a synthesis method of a diaminodiphenylethane compound, relating to the technical field of compound preparation; adding an alkaline solution into an ionic liquid catalyst and nitro-o-xylene to prepare a nitro-o-xylene solution, carrying out coupling reaction on the nitro-o-xylene solution under the action of continuous oxygen introduction, neutralizing to neutrality, filtering and washing to obtain a dimethyl dinitro-diphenylethane solid if a solvent in the alkaline solution is mutually soluble with water, preparing the dimethyl dinitro-diphenylethane solid into a dimethyl dinitro-diphenylethane solution, layering if the solvent in the alkaline solution is not mutually soluble with water to obtain a dimethyl dinitro-diphenylethane solution as an oil layer, carrying out hydrogenation reaction on the dimethyl dinitro-diphenylethane solution under the action of continuous hydrogen introduction, and distilling the oil layer after reaction liquid layering to obtain the dimethyl diamino-diphenylethane.
Description
Technical Field
The invention discloses a synthesis method of a diaminodiphenylethane compound, and relates to the technical field of compound preparation.
Background
The derivatives of the diaminodiphenylethane compound are important intermediates for preparing various chemical raw materials, dyes, medicines, pesticides, various auxiliaries, optical materials, electronic materials and devices thereof.
When the diaminodiphenylethane compound is synthesized, the used solid catalyst must have the conditions of high activity, good selectivity and long-term stability as much as possible, and must also have high mechanical strength and good heat transfer, mass transfer and hydrodynamic properties, the use conditions are harsh, the problems of long reaction period, high consumption, high cost and high waste amount are easily caused, and the large-scale industrial production is not facilitated.
Disclosure of Invention
The invention aims at the problems of the prior art and discloses a method for synthesizing a diaminodiphenylethane compound, which takes 3- (or 4-) nitro-o-xylene as an initial raw material and prepares dimethyl dinitrodiphenylethane through coupling reaction under the strong alkaline condition and the action of an ionic liquid catalyst and under the condition that oxygen is taken as an oxidant; then the dimethyl diamino diphenylethane is prepared by catalytic hydrogenation. The invention provides a synthesis method of a diaminodiphenylethane compound, which has the advantages of high catalytic activity, high yield, continuous operation, less storage of online dangerous materials, safer relative operation, easy stable control, stable product quality, high yield, short reaction period, lower consumption, lower cost and less three wastes, and meets the requirement of clean production by adopting an environment-friendly oxidant, namely oxygen oxidation and hydrogenation reduction, thereby being beneficial to large-scale industrial production.
The specific scheme provided by the invention is as follows:
a method for synthesizing a diaminodiphenylethane compound comprises the following steps: adding an alkaline solution into an ionic liquid catalyst and the nitro-o-xylene to prepare a nitro-o-xylene solution,
the nitro-o-xylene solution is subjected to coupling reaction under the action of continuous oxygen introduction, neutralized to be neutral,
if the solvent in the alkaline solution is mutually soluble with water, filtering and washing to obtain dimethyl dinitrodiphenylethane solid, preparing the dimethyl dinitrodiphenylethane solid into dimethyl dinitrodiphenylethane solution,
if the solvent in the alkaline solution is not mutually soluble with water, the oil layer is layered to obtain a dimethyl dinitrodiphenylethane solution, the dimethyl dinitrodiphenylethane solution is subjected to hydrogenation reaction under the action of continuously introducing hydrogen, and after the reaction liquid is layered, the oil layer is distilled to obtain the dimethyl diaminodiphenylethane.
The solvent of the alkaline solution in the synthesis method includes but is not limited to the following solvents: methanol, ethanol, propanol, butanol, tert-butanol, pentanol, tetrahydrofuran, dioxane, N-dimethylformamide, acetone, butanone, pentanone, dichloroethane, chloroform, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, cyclohexane, ethyl acetate,
the mass ratio of the solvent of the alkaline solution to the nitro-o-xylene is 1-10: 1.
In the synthesis method, dimethyl dinitrodiphenylethane solid is utilized and is not limited to the following solvents: butanone, pentanone, dichloroethane, chloroform, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, cyclohexane, ethyl acetate,
preparing a dimethyl dinitrodiphenylethane solution, wherein the mass ratio of the solvent to the nitro-o-xylene is 1-10: 1.
The ionic liquid catalyst in the synthesis method includes, but is not limited to, tetrafluoroborated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) BF4, hexafluorophosphorylated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) PF6, tetrafluoroborated 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) BF4, hexafluorophosphorylated 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) PF6, tetrafluoroborated 1-octyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (ODBU) BF4, hexafluorophosphorylated 1-octyl-1, one or more of 8-diazabicyclo (5, 4, 0) undec-7-ene (ODBU) PF6,
the mass ratio of the ionic liquid catalyst to the nitro-o-xylene is 0.01-1: 1.
The solute of the alkaline solution in the synthesis method comprises but is not limited to one or a mixture of more of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium hydride, sodium ethoxide, triethylamine, triethanolamine, sodium tert-butoxide, potassium tert-butoxide and sodium amide,
the molar ratio of the solute of the alkaline solution to the nitro-o-xylene is 0.1-5: 1.
In the synthesis method, the coupling reaction is carried out in a microchannel reactor, and the hydrogenation reaction is carried out in a fixed bed reactor.
In the synthesis method, the feeding rate of the nitro-o-xylene solution entering the fixed bed reactor is 500kg/h-4000 kg/h.
In the synthesis method, the feeding rate of oxygen entering the fixed bed reactor is 30kg/h-200 kg/h.
The catalyst adopted in the hydrogenation reaction in the synthesis method is a Pd/C catalyst.
The coupling reaction equation in the synthesis method is as follows:
or the following steps:
the equation for the hydrogenation reduction reaction is:
or the following steps:
a diaminodiphenylethane compound is synthesized by the following method: adding an alkaline solution into an ionic liquid catalyst and the nitro-o-xylene to prepare a nitro-o-xylene solution,
the nitro-o-xylene solution is subjected to coupling reaction under the action of continuous oxygen introduction, neutralized to be neutral,
if the solvent in the alkaline solution is mutually soluble with water, filtering and washing to obtain dimethyl dinitrodiphenylethane solid, preparing the dimethyl dinitrodiphenylethane solid into dimethyl dinitrodiphenylethane solution,
if the solvent in the alkaline solution is not mutually soluble with water, the oil layer is layered to obtain a dimethyl dinitrodiphenylethane solution, the dimethyl dinitrodiphenylethane solution is subjected to hydrogenation reaction under the action of continuously introducing hydrogen, and after the reaction liquid is layered, the oil layer is distilled to obtain the dimethyl diaminodiphenylethane.
The application of the diaminodiphenylethane compound is provided. For example, derivatives of diaminodiphenylethane compounds are used to prepare chemical raw materials, dyes, medicines, pesticides, various auxiliaries, optical materials, electronic materials and important intermediates of devices thereof.
The invention has the advantages that:
the invention provides a method for synthesizing a diaminodiphenylethane compound, which selects ionic liquid as a catalyst for coupling reaction, overcomes the defects of the existing solid catalyst and homogeneous catalyst, has high catalytic activity and high yield, has less on-line dangerous materials storage in continuous reaction, is relatively safe to operate, is easy to stably control, realizes continuous and stable operation, and is suitable for large-scale industrial mass production. The temperature and the feeding speed can be simply and controllably controlled, the reaction efficiency is correspondingly improved due to the great improvement of the reaction speed, the production process is changed from the existing intermittent operation into the continuous operation, the reaction time is shortened, the energy consumption is reduced, reaction byproducts are correspondingly and greatly reduced due to the great reduction of the reaction time, the selectivity is high, the obtained product has less impurities, and the product purity can reach more than 99.0 percent; the product has high synthesis yield which is more than or equal to 88 percent calculated by the nitro-o-xylene, low consumption and low cost, and simultaneously, the green and environment-friendly oxidant oxygen is adopted for oxidation, and the hydrogenation reduction also meets the requirement of clean production.
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FIG. 1 is a schematic flow diagram of the process of the present invention.
Detailed Description
The invention provides a synthesis method of diaminodiphenylethane compound, which comprises adding alkaline solution into ionic liquid catalyst and nitro-o-xylene to prepare nitro-o-xylene solution,
the nitro-o-xylene solution is subjected to coupling reaction under the action of continuous oxygen introduction, neutralized to be neutral,
if the solvent in the alkaline solution is mutually soluble with water, filtering and washing to obtain dimethyl dinitrodiphenylethane solid, preparing the dimethyl dinitrodiphenylethane solid into dimethyl dinitrodiphenylethane solution,
if the solvent in the alkaline solution is not mutually soluble with water, the oil layer is layered to obtain a dimethyl dinitrodiphenylethane solution, the dimethyl dinitrodiphenylethane solution is subjected to hydrogenation reaction under the action of continuously introducing hydrogen, and after the reaction liquid is layered, the oil layer is distilled to obtain the dimethyl diaminodiphenylethane.
Simultaneously provides a diaminodiphenylethane compound corresponding to the method, and is synthesized by the method.
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Example 1
Dissolving 10kg of sodium methoxide in 1500kg of ethanol, adding 306kg of 99% 4-nitro-o-xylene and 3kg of tetrafluoroborated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) BF4 to prepare a nitro-o-xylene solution,
controlling the temperature to be 25-35 ℃, the feeding rate of the nitro-o-xylene solution to be 1500kg/h-2000kg/h and the feeding rate of the nitro-o-xylene solution and oxygen to be 30kg/h-40kg/h, continuously feeding the mixture into a microchannel reactor at 25-35 ℃ for continuous coupling reaction, adding 1500kg of water into reaction liquid after the reaction lasts for a period of time, neutralizing the reaction liquid with 2.1kg of 31 percent hydrochloric acid until the pH value is 7,
cooling to 5 ℃, filtering to obtain dimethyl dinitrodiphenylethane solid wet material, drying the wet material at 80 ℃, adding 1500kg of dichloroethane, preparing dimethyl dinitrodiphenylethane solution, controlling the temperature to be 20-60 ℃, the feeding rate to be 900kg/h-1100kg/h, the feeding rate to hydrogen to be 8kg/h-14kg/h, continuously feeding the solution into a fixed bed reactor filled with 30kg of hydrogenation catalyst and 5 percent Pd/C for hydrogenation reaction at 20-60 ℃,
the reaction solution was layered, and the oil layer was distilled in a thin film evaporator to obtain 423kg of dimethyl diamino diphenyl ethane with a content of 99.3% and a yield of 88.3%.
Example 2
Dissolving 7kg of sodium hydride in 1000kg of dioxane, adding 306kg of 99% 3-nitro-o-xylene and 6kg of hexafluorophosphorylated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) PF6 to prepare a nitro-o-xylene solution,
controlling the temperature to be 40-60 ℃, the feeding rate of the nitro-o-xylene solution to be 1000kg/h-1500kg/h and the feeding rate of the nitro-o-xylene solution and oxygen to be 30kg/h-40kg/h, continuously feeding the mixture into a microchannel reactor at 40-60 ℃ for continuous coupling reaction, adding 1500kg of water into reaction liquid after the reaction lasts for a period of time, neutralizing the reaction liquid with 2kg of 31 percent hydrochloric acid until the pH value is 7,
cooling to 15 ℃, filtering to obtain a wet solid dimethyl dinitrodiphenylethane material, drying the wet material at 100 ℃, adding 583kg of chloroform to obtain a dimethyl dinitrodiphenylethane solution, controlling the temperature to be 30-60 ℃, the feeding rate to be 900kg/h-1100kg/h and the feeding rate to be 8kg/h-20kg/h, continuously feeding the solution into a fixed bed reactor filled with 20kg of hydrogenation catalyst and 5 percent Pd/C for hydrogenation reaction at the temperature of 30-60 ℃,
the reaction solution was layered, and the oil layer was distilled in a thin film evaporator to obtain 428kg of dimethyldiaminodiphenylethane with a content of 99.2% and a yield of 88.5%.
Example 3
40kg of triethanolamine was dissolved in 2000kg of N, N-dimethylformamide, and 612kg of 99% 4-nitro-o-xylene and 12kg of 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene tetrafluoroborate (HDBU) BF4 were added to prepare a nitro-o-xylene solution,
controlling the temperature to be 60-80 ℃, the feeding rate of the nitro-o-xylene solution to be 1500kg/h-2000kg/h and the feeding rate of the nitro-o-xylene solution and oxygen to be 30kg/h-40kg/h, continuously feeding the mixture into a 60-80 ℃ microchannel reactor for continuous coupling reaction, adding 2000kg of water into reaction liquid after the reaction lasts for a period of time, neutralizing the reaction liquid with 4.5kg of 31 percent hydrochloric acid until the pH value is 7,
cooling to 10 ℃, filtering to obtain a wet solid dimethyl dinitrodiphenylethane material, drying the wet material at 100 ℃, then 1172kg, adding 1500kg of toluene to obtain a dimethyl dinitrodiphenylethane solution, controlling the temperature to be 70-80 ℃, the feeding rate to be 900kg/h-1100kg/h and the feeding rate to be 8kg/h-16kg/h of hydrogen, continuously feeding the solution into a fixed bed reactor filled with 50kg of hydrogenation catalyst 5% Pd/C for hydrogenation reaction at 70-80 ℃,
the reaction solution is layered, and the oil layer enters a film evaporator for distillation to obtain 870kg of dimethyl diamino diphenyl ethane with the content of 99.3 percent and the yield of 89.3 percent.
Example 4
90kg of potassium tert-butoxide was dissolved in 2000kg of toluene, and added to 612kg of 99% 3-nitro-o-xylene and 20kg of hexafluorophosphorylated 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) PF6 to prepare a nitro-o-xylene solution,
controlling the temperature to be 80-100 ℃, the feeding rate of the nitro-o-xylene solution to be 1500kg/h-2000kg/h and the feeding rate of the oxygen to be 40kg/h-60kg/h, continuously feeding the mixture into a microchannel reactor at the temperature of 80-100 ℃ for continuous coupling reaction, adding 500kg of water into reaction liquid after the reaction lasts for a period of time, neutralizing the reaction liquid to pH 7 by using 10kg of 31 percent hydrochloric acid, standing and layering, wherein an oil layer is a dimethyl dinitrodiphenylethane solution,
controlling the temperature to be 80-90 ℃, the feeding rate to be 900kg/h-1120kg/h, the feeding rate to hydrogen to be 8kg/h-20kg/h, continuously feeding the mixture into a fixed bed reactor filled with 50kg of hydrogenation catalyst and 5 percent Pd/C for hydrogenation reaction at the temperature of 80-90 ℃,
the reaction solution was layered, and the oil layer was distilled in a thin film evaporator to obtain 854kg of dimethyl diamino diphenyl ethane with a content of 99.4% and a yield of 88.6%.
Example 5
Dissolving 70kg of sodium amide in 3000kg of chlorobenzene, adding to a mixture of 918kg of 99% 3-nitro-o-xylene and 60kg of 1-octyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (ODBU) BF4 tetrafluoroborated and 20kg of 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) PF6 hexafluorophosphorated to prepare a nitro-o-xylene solution,
the temperature is controlled to be 100 ℃ and 120 ℃, and the feeding rate of the nitro-o-xylene solution is 2000kg/h-3000 kg/h. Feeding the mixture and oxygen at a feeding rate of 40-60 kg/h into a microchannel reactor at 100-120 ℃ for continuous coupling reaction, adding 500kg of water into reaction liquid after the reaction lasts for a period of time, neutralizing the reaction liquid to pH 7 with 10kg of 31% hydrochloric acid, standing and layering, wherein an oil layer is a dimethyl dinitrodiphenylethane solution, controlling the temperature to be 90-100 ℃, the feeding rate to be 900-1100 kg/h and the hydrogen feeding rate to be 8-20 kg/h, continuously feeding the mixture into a fixed bed reactor filled with 50kg of hydrogenation catalyst and 5% Pd/C for hydrogenation reaction at the temperature of 90-100 ℃,
the reaction solution was layered, and the oil layer was distilled in a thin film evaporator to obtain 1288kg of dimethyl diaminodiphenylethane with a content of 99.2% and a yield of 89.1%.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (10)
1. A process for synthesizing diamino-diphenylethane compound features that the alkaline solution is added to ionic liquid catalyst and nitro-o-xylene to obtain nitro-o-xylene solution or
The nitro-o-xylene solution is subjected to coupling reaction under the action of continuous oxygen introduction, neutralized to be neutral,
if the solvent in the alkaline solution is mutually soluble with water, filtering and washing to obtain dimethyl dinitrodiphenylethane solid, preparing the dimethyl dinitrodiphenylethane solid into dimethyl dinitrodiphenylethane solution,
if the solvent in the alkaline solution is not mutually soluble with water, the oil layer is layered to obtain a dimethyl dinitrodiphenylethane solution, the dimethyl dinitrodiphenylethane solution is subjected to hydrogenation reaction under the action of continuously introducing hydrogen, and after the reaction liquid is layered, the oil layer is distilled to obtain the dimethyl diaminodiphenylethane.
2. The synthesis method according to claim 1, wherein the solvent of the alkaline solution includes but is not limited to the following solvents: methanol, ethanol, propanol, butanol, tert-butanol, pentanol, tetrahydrofuran, dioxane, N-dimethylformamide, acetone, butanone, pentanone, dichloroethane, chloroform, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, cyclohexane, ethyl acetate,
the mass ratio of the solvent of the alkaline solution to the nitro-o-xylene is 1-10: 1.
3. The synthesis process according to claim 1 or 2, characterized in that the dimethyl dinitrodiphenylethane solid is obtained by using but not limited to the following solvents: butanone, pentanone, dichloroethane, chloroform, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, cyclohexane, ethyl acetate,
preparing a dimethyl dinitrodiphenylethane solution, wherein the mass ratio of the solvent to the nitro-o-xylene is 1-10: 1.
4. The synthesis method according to claim 3, characterized in that the ionic liquid catalyst includes but is not limited to tetrafluoroborated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) BF4, hexafluorophosphorylated 1-butyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (BDBU) PF6, tetrafluoroborated 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) BF4, hexafluorophosphorylated 1-hexyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (HDBU) PF6, tetrafluoroborated 1-octyl-1, 8-diazabicyclo (BU 5, 4, 0) undec-7-ene (ODBU) BF4, one or more of hexafluorophosphorylation 1-octyl-1, 8-diazabicyclo (5, 4, 0) undec-7-ene (ODBU) PF6,
the mass ratio of the ionic liquid catalyst to the nitro-o-xylene is 0.01-1: 1.
5. The synthesis method according to claim 1 or 4, wherein the solute of the alkaline solution includes but is not limited to one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium hydride, sodium ethoxide, triethylamine, triethanolamine, sodium tert-butoxide, potassium tert-butoxide and sodium amide,
the molar ratio of the solute of the alkaline solution to the nitro-o-xylene is 0.1-5: 1.
6. The synthesis process as claimed in claim 5, wherein the coupling reaction is carried out in a microchannel reactor and the hydrogenation reaction is carried out in a fixed bed reactor.
7. The synthesis process as claimed in claim 6, characterized in that the feeding rate of the nitro-o-xylene solution into the fixed bed reactor is from 500kg/h to 4000 kg/h.
8. The synthesis process as claimed in claim 6 or 7, characterized in that the feed rate of oxygen into the fixed-bed reactor is from 30kg/h to 200 kg/h.
9. A diamino diphenylethane compound is characterized by being synthesized by the following method: adding an alkaline solution into an ionic liquid catalyst and the nitro-o-xylene to prepare a nitro-o-xylene solution,
the nitro-o-xylene solution is subjected to coupling reaction under the action of continuous oxygen introduction, neutralized to be neutral,
if the solvent in the alkaline solution is mutually soluble with water, filtering and washing to obtain dimethyl dinitrodiphenylethane solid, preparing the dimethyl dinitrodiphenylethane solid into dimethyl dinitrodiphenylethane solution,
if the solvent in the alkaline solution is not mutually soluble with water, the oil layer is layered to obtain a dimethyl dinitrodiphenylethane solution, the dimethyl dinitrodiphenylethane solution is subjected to hydrogenation reaction under the action of continuously introducing hydrogen, and after the reaction liquid is layered, the oil layer is distilled to obtain the dimethyl diaminodiphenylethane.
10. Use of a diaminodiphenylethane compound according to claim 9.
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| CN113800478B (en) * | 2021-10-13 | 2023-12-15 | 山东迅达催化剂有限公司 | Low-carbon and ultralow-sulfur emission acid gas sulfur recovery process |
| CN114213651A (en) * | 2022-01-26 | 2022-03-22 | 东华大学 | Preparation method of polyetherimide |
| CN114213651B (en) * | 2022-01-26 | 2023-02-17 | 东华大学 | Preparation method of polyetherimide |
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