CN114149327A - Method for synthesizing o-phenylenediamine through continuous ammoniation - Google Patents
Method for synthesizing o-phenylenediamine through continuous ammoniation Download PDFInfo
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- CN114149327A CN114149327A CN202111300885.3A CN202111300885A CN114149327A CN 114149327 A CN114149327 A CN 114149327A CN 202111300885 A CN202111300885 A CN 202111300885A CN 114149327 A CN114149327 A CN 114149327A
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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
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention relates to a method for synthesizing o-phenylenediamine by continuous ammoniation, which comprises the following steps: adding o-dichlorobenzene into a continuous reaction kettle, adding liquid ammonia while stirring, heating to 85-100 ℃, controlling the reaction pressure to be 5-6MPa, adding a catalyst, reacting for 6 hours, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 5-10, and the amount of the catalyst is 1-1.5% of the weight of the o-dichlorobenzene; the catalyst comprises cuprous chloride and a synergosome, wherein the synergosome can be a phosphorus ligand framework structure in structural view, can be used as a strong power supply ligand, can influence the space structure and the electronic effect of a metal center when being combined with the cuprous chloride, and improves the catalytic activity of a catalytic system, so that the catalyst prepared by the method has excellent catalytic performance on the synthesis of o-phenylenediamine.
Description
Technical Field
The invention belongs to the technical field of o-phenylenediamine synthesis, and particularly relates to a method for continuously ammoniating and synthesizing o-phenylenediamine.
Background
O-phenylenediamine is an important organic chemical intermediate, is used for producing dyes, is also a main raw material of systemic bactericides such as carbendazim, benomyl, (methyl) thiophanate and the like, and is also an important raw material of developers, leveling agents, surfactants and the like.
The synthesis of o-phenylenediamine is mainly as follows, and patent CN102633653 reports a method for preparing o-phenylenediamine by catalytic hydrogenation of o-nitroaniline, wherein o-nitroaniline is used as a raw material, alcohol is used as a solvent, nickel is used as a catalyst, the reaction is carried out for 2-10 hours under the hydrogen pressure of 1-6MPa and the temperature of 40-80 ℃, and white o-phenylenediamine is obtained by rectification.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for continuously ammoniating and synthesizing o-phenylenediamine.
The purpose of the invention can be realized by the following technical scheme:
a method for synthesizing o-phenylenediamine by continuous ammoniation comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle, adding liquid ammonia while stirring, heating to 85-100 ℃, controlling the reaction pressure to be 5-6MPa, adding a catalyst, reacting for 6 hours, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 5-10, and the amount of the catalyst is 1-1.5% of the weight of the o-dichlorobenzene;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 3-5: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, then adding the crude product into n-heptane, adding a decomplexing agent, slowly stirring for 1h, standing for 1h, removing lower-layer liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of the benzene, the phosphorus trichloride and the aluminum trichloride to be 1: 1.2-1.3, and controlling the dosage of the decomplexing agent to be 3-5% of the weight of the crude product;
in the step S1, benzene, phosphorus trichloride and aluminum trichloride react to generate an intermediate 1, and the reaction process is as follows:
step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, then placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, then heating to 25 ℃, preserving heat, reacting for 30h to obtain a mixed solution, filtering, performing rotary evaporation to remove a half of a solvent, sealing, standing for 20h at-25 ℃, removing a supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and then performing vacuum drying to obtain a synergistic body, wherein the volume ratio of the intermediate 1, the triethylamine and the tetrahydrofuran is controlled to be 2.65 mL: 2.15-2.2 mL: 20 mL.
In the step S2, the intermediate 1 reacts with 2-aminophenol to generate a synaptosome, and the reaction process is as follows:
the synergist is a phosphorus ligand framework structure in structural view, can be used as a strong power supply ligand, can influence the spatial structure and electronic effect of a metal center when being combined with a metal catalyst, and improves the catalytic activity of a catalytic system, so that on one hand, the yield is improved by a continuous ammoniation mode, and on the other hand, the catalyst with high catalytic activity is prepared, the yield of o-phenylenediamine is further improved, the energy consumption is not increased, and a large amount of energy consumption is not caused.
Further: the tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
Further: the decomplexer is any one of pyridine and picoline.
The invention has the beneficial effects that:
the invention relates to a method for synthesizing o-phenylenediamine by continuous ammoniation, which solves the technical problems of poor product quality, high energy consumption, large safety risk and the like of the currently adopted intermittent ammoniation method by adopting a continuous ammoniation method to synthesize the o-phenylenediamine on the one hand, improves the yield of the o-phenylenediamine, and prepares a catalyst on the other hand, the catalyst comprises cuprous chloride and a synergosome, the synergosome can be a phosphorus ligand framework structure from the structural point of view, can be used as a strong power supply ligand, when the catalyst is combined with cuprous chloride, the space structure and the electronic effect of a metal center can be influenced, the catalytic activity of a catalytic system is improved, further, the catalyst prepared by the invention has excellent catalytic performance for synthesizing o-phenylenediamine, therefore, the invention further improves the yield of the o-phenylenediamine, does not increase energy consumption and does not cause large energy consumption.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for synthesizing o-phenylenediamine by continuous ammoniation comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in the invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 85 ℃, controlling the reaction pressure to be 5MPa, adding a catalyst, reacting for 6 hours, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 5, the amount of the catalyst is 1% of the weight of the o-dichlorobenzene, the yield of the o-phenylenediamine is 92.5%, and the purity is 99.1%;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 3: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, then adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower layer liquid, carrying out reduced pressure distillation to obtain an intermediate 1, and controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1: 1.2, wherein the using amount of pyridine is 3% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, then placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, then heating to 25 ℃, preserving heat, reacting for 30h to obtain a mixed solution, filtering, performing rotary evaporation to remove a half solvent, sealing, standing for 20h at-25 ℃, removing a supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and then performing vacuum drying to obtain a synergistic body, wherein the volume ratio of the intermediate 1, triethylamine and tetrahydrofuran is controlled to be 2.65 mL: 2.15 mL: 20 mL.
The tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
Example 2
A method for synthesizing o-phenylenediamine by continuous ammoniation comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in the invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 85 ℃, controlling the reaction pressure to be 5MPa, adding a catalyst, reacting for 6 hours, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 6, the dosage of the catalyst is 1.2% of the weight of the o-dichlorobenzene, the yield of the o-phenylenediamine is 92.8%, and the purity is 99.1%;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 3.5: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, then adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower-layer liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1: 1.25, and controlling the using amount of pyridine to be 3.5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, then placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, then heating to 25 ℃, preserving heat, reacting for 30h to obtain a mixed solution, filtering, performing rotary evaporation to remove a half solvent, sealing, standing for 20h at-25 ℃, removing a supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and then performing vacuum drying to obtain a synergistic body, wherein the volume ratio of the intermediate 1, triethylamine and tetrahydrofuran is controlled to be 2.65 mL: 2.18 mL: 20 mL.
The tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
Example 3
A method for synthesizing o-phenylenediamine by continuous ammoniation comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in the invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 90 ℃, controlling the reaction pressure to be 5.5MPa, adding a catalyst, reacting for 6h, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 8, the amount of the catalyst is 1.4% of the weight of the o-dichlorobenzene, the yield of the o-phenylenediamine is 92.3%, and the purity of the o-phenylenediamine is 99.5%;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 4.5: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, then adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower-layer liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1: 1.28, and controlling the using amount of pyridine to be 4.5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, then placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, then heating to 25 ℃, preserving heat, reacting for 30h to obtain a mixed solution, filtering, performing rotary evaporation to remove a half solvent, sealing, standing for 20h at-25 ℃, removing a supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and then performing vacuum drying to obtain a synergistic body, wherein the volume ratio of the intermediate 1, triethylamine and tetrahydrofuran is controlled to be 2.65 mL: 2.2 mL: 20 mL.
The tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
Example 4
A method for synthesizing o-phenylenediamine by continuous ammoniation comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in the invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 100 ℃, controlling the reaction pressure to be 6MPa, adding a catalyst, reacting for 6 hours, separating an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine, wherein the molar ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1: 10, the dosage of the catalyst is 1.5% of the weight of the o-dichlorobenzene, the yield of the o-phenylenediamine is 92.8%, and the purity is 99.0%;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 5: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, then adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower-layer liquid, carrying out reduced pressure distillation to obtain an intermediate 1, and controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1: 1.3, wherein the using amount of pyridine is 5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, then placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, then heating to 25 ℃, preserving heat, reacting for 30h to obtain a mixed solution, filtering, performing rotary evaporation to remove a half solvent, sealing, standing for 20h at-25 ℃, removing a supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and then performing vacuum drying to obtain a synergistic body, wherein the volume ratio of the intermediate 1, triethylamine and tetrahydrofuran is controlled to be 2.65 mL: 2.2 mL: 20 mL.
The tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
Comparative example 1
Compared with the example 1, the yield of the o-phenylenediamine is 90.5% and the purity is 99.0% by ammoniation in a common reaction kettle.
Comparative example 2
This comparative example compares with example 1, the yield of o-phenylenediamine is 89.3% with cuprous chloride as catalyst, and the purity is 99.2%.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (7)
1. A method for synthesizing o-phenylenediamine by continuous ammoniation is characterized by comprising the following steps: the method comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle, adding liquid ammonia while stirring, heating to 85-100 ℃, controlling the reaction pressure to be 5-6MPa, adding a catalyst, reacting for 6 hours, separating out an oil phase at 100 ℃ after the reaction is finished, and carrying out vacuum distillation to obtain o-phenylenediamine;
the catalyst is formed by mixing cuprous chloride and a synergist according to the weight ratio of 3-5: 1, and the synergist comprises the following steps:
step S1, adding benzene into a three-neck flask, sequentially adding phosphorus trichloride and aluminum trichloride, introducing nitrogen, stirring at a high speed, heating to 150 ℃, carrying out reflux reaction until white smoke generated disappears, cooling to room temperature to obtain a crude product, and carrying out post-treatment to obtain an intermediate 1;
and step S2, adding the intermediate 1 into a flask containing tetrahydrofuran, stirring at a constant speed, adding triethylamine, continuously stirring for 5min, placing into an ice water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring, stirring at a constant speed, reacting for 30min, heating to 25 ℃, keeping the temperature, reacting for 30h, preparing a mixed solution, and purifying to obtain the synergosome.
2. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 1, wherein: the post-treatment comprises the following steps: adding the crude product into n-heptane, adding decomplexing agent, slowly stirring for 1 hr, standing for 1 hr, removing lower layer liquid, and distilling under reduced pressure.
3. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 1, wherein: in step S1, the molar ratio of benzene, phosphorus trichloride and aluminum trichloride is controlled to be 1: 1.2-1.3.
4. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 1, wherein: in step S2, the volume ratio of the intermediate 1, triethylamine and tetrahydrofuran is controlled to be 2.65 mL: 2.15-2.2 mL: 20mL, and the dosage of the decomplexer is 3-5% of the weight of the crude product.
5. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 1, wherein: the mol ratio of o-dichlorobenzene to liquid ammonia is controlled to be 1: 5-10, and the dosage of the catalyst is 1-1.5% of the weight of the o-dichlorobenzene.
6. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 1, wherein: the tetrahydrofuran solution of the 2-aminophenol is prepared by mixing the 2-aminophenol and tetrahydrofuran according to the dosage ratio of 0.25g to 0.5 mL.
7. The method for continuously ammoniating and synthesizing o-phenylenediamine according to claim 2, wherein: the decomplexer is any one of pyridine and picoline.
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| CN105037171A (en) * | 2015-06-08 | 2015-11-11 | 江阴市华亚化工有限公司 | Method for synthesizing and preparing o-phenylenediamine from orthodichlorobenzene |
| CN107188905A (en) * | 2017-05-22 | 2017-09-22 | 东北石油大学 | A kind of amino phenolic group phosphorus part and its application in vinyl polymerization and oligomerisation |
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| CN112194583A (en) * | 2020-09-18 | 2021-01-08 | 江苏方圆芳纶研究院有限公司 | Preparation method of o-phenylenediamine |
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