CN114149327B - Method for synthesizing o-phenylenediamine by continuous ammonification - Google Patents
Method for synthesizing o-phenylenediamine by continuous ammonification Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- 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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- 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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- 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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- 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
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Abstract
The invention relates to a method for synthesizing o-phenylenediamine by continuous ammonification, which comprises the following steps: adding o-dichlorobenzene into a continuous reaction kettle, stirring, adding liquid ammonia, heating to 85-100 ℃, controlling the reaction pressure to 5-6MPa, 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 1:5-10, and the dosage of the catalyst is 1-1.5% of the weight of the o-dichlorobenzene; the catalyst comprises cuprous chloride and a synergistic body, wherein the synergistic body can be a phosphorus ligand skeleton structure from the structural aspect, 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 invention has excellent catalytic performance on synthesizing o-phenylenediamine.
Description
Technical Field
The invention belongs to the technical field of o-phenylenediamine synthesis, and particularly relates to a method for synthesizing o-phenylenediamine by continuous ammonification.
Background
The o-phenylenediamine is an important intermediate of organic chemical industry, is used for dye production, is also a main raw material of systemic bactericides such as pesticide carbendazim, benomyl, (methyl) thiophanate and the like, and is also an important raw material of developer, leveling agent, surfactant and the like.
The synthesis of o-phenylenediamine mainly comprises the following method, patent CN102633653 reports a method for preparing o-phenylenediamine by catalytic hydrogenation of o-nitroaniline, wherein the o-nitroaniline is used as a raw material, alcohol is used as a solvent, nickel is used as a catalyst, reduction reaction is carried out for 2-10 hours at the hydrogen pressure of 1-6MPa and the temperature of 40-80 ℃, white o-phenylenediamine is obtained by rectification, and the reaction formula is as follows.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for synthesizing o-phenylenediamine by continuous ammonification.
The aim of the invention can be achieved by the following technical scheme:
a method for synthesizing o-phenylenediamine by continuous ammonification comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle, stirring, adding liquid ammonia, heating to 85-100 ℃, controlling the reaction pressure to 5-6MPa, 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 1:5-10, and the dosage of the catalyst is 1-1.5% of the weight of the o-dichlorobenzene;
the catalyst is prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 3-5:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding a decomplexing agent, slowly stirring for 1h, standing for 1h, removing lower 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, wherein the dosage of the decomplexing agent is 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 filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring continuously for 5min, placing in an ice-water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring at a constant speed, reacting for 30min, heating to 25 ℃, preserving heat for 30h to obtain a mixed solution, filtering, steaming to remove half of the solvent, sealing, standing at-25 ℃ for 20h, removing supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and drying in vacuum 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 synergistic body, and the reaction process is as follows:
the synergistic body is structurally a phosphorus ligand skeleton structure, can be used as a strong power supply ligand, and can influence the space structure and the electronic effect of a metal center when being combined with a metal catalyst, so that the catalytic activity of a catalytic system is improved.
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 decomplexing agent 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 ammonification, which solves the technical problems of poor product quality, high energy consumption, high safety risk and the like of the intermittent ammonification method adopted at present by adopting the continuous ammonification method to synthesize the o-phenylenediamine, improves the yield of the o-phenylenediamine, and prepares a catalyst which comprises cuprous chloride and a synergistic body, wherein the synergistic body structurally can be a phosphorus ligand skeleton structure and can be used as a strong power supply ligand, and when the synergistic body is combined with the cuprous chloride, the space structure and the electronic effect of a metal center can be influenced to improve the catalytic activity of a catalytic system, so that the catalyst has excellent catalytic performance on the o-phenylenediamine synthesis, and the yield of the o-phenylenediamine is further improved without increasing the energy consumption and causing a large amount of energy consumption.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A method for synthesizing o-phenylenediamine by continuous ammonification comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in an invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 85 ℃, controlling the reaction pressure to 5MPa, adding a catalyst, reacting for 6 hours, separating an oil phase at 100 ℃ after the reaction is finished, and performing 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 consumption 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 prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 3:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1:1:1.2, wherein the consumption of the pyridine is 3% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring continuously for 5min, placing in an ice-water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring at a constant speed, reacting for 30min, heating to 25 ℃, preserving heat for 30h to obtain a mixed solution, filtering, steaming to remove half of the solvent, sealing, standing at-25 ℃ for 20h, removing supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and drying in vacuum 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 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 ammonification comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in an invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 85 ℃, controlling the reaction pressure to 5MPa, 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 1:6, the consumption 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 prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 3.5:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1:1:1.25, wherein the consumption of the pyridine is 3.5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring continuously for 5min, placing in an ice-water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring at a constant speed, reacting for 30min, heating to 25 ℃, preserving heat for 30h to obtain a mixed solution, filtering, steaming to remove half of the solvent, sealing, standing at-25 ℃ for 20h, removing supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and drying in vacuum 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/2.18 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 ammonification comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in an invention patent CN201710645689.7, adding liquid ammonia while stirring, heating to 90 ℃, controlling the reaction pressure to 5.5MPa, adding a catalyst, reacting for 6 hours, separating an oil phase at 100 ℃ after the reaction is finished, and performing 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 consumption 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 is 99.5%;
the catalyst is prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 4.5:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1:1:1.28, wherein the consumption of the pyridine is 4.5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring continuously for 5min, placing in an ice-water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring at a constant speed, reacting for 30min, heating to 25 ℃, preserving heat for 30h to obtain a mixed solution, filtering, steaming to remove half of the solvent, sealing, standing at-25 ℃ for 20h, removing supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and drying in vacuum 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/2.2 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 ammonification comprises the following steps:
adding o-dichlorobenzene into a continuous reaction kettle disclosed in an 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 consumption 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 prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 5:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding pyridine, slowly stirring for 1h, standing for 1h, removing lower liquid, carrying out reduced pressure distillation to obtain an intermediate 1, controlling the molar ratio of benzene, phosphorus trichloride and aluminum trichloride to be 1:1:1.3, wherein the consumption of the pyridine is 5% of the weight of the crude product;
step S2, adding the intermediate 1 into a flask filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring continuously for 5min, placing in an ice-water bath, dropwise adding a tetrahydrofuran solution of 2-aminophenol while stirring at a constant speed, reacting for 30min, heating to 25 ℃, preserving heat for 30h to obtain a mixed solution, filtering, steaming to remove half of the solvent, sealing, standing at-25 ℃ for 20h, removing supernatant, washing a filter cake with absolute ethyl alcohol at-30 ℃, and drying in vacuum 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/2.2 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 comparative example adopts a common reaction kettle for ammonification, and the yield of the o-phenylenediamine is 90.5 percent and the purity is 99.0 percent.
Comparative example 2
In this comparative example, compared with example 1, the yield of o-phenylenediamine was 89.3% and the purity was 99.2% using cuprous chloride as a catalyst.
In the description of the present specification, the descriptions of the terms "one embodiment," "example," "specific example," and the like, 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 present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. 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 merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the scope of the invention or exceeding the scope of the invention as defined in the claims.
Claims (6)
1. A method for synthesizing o-phenylenediamine by continuous ammonification 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 5-6MPa, 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;
the catalyst is prepared by mixing cuprous chloride and a synergistic body according to the weight ratio of 3-5:1, wherein the synergistic body comprises the following steps:
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, adding the crude product into n-heptane, adding a decomplexing agent, slowly stirring for 1h, standing for 1h, removing lower liquid, and carrying out reduced pressure distillation to obtain an intermediate 1;
step S2, adding the intermediate 1 into a flask filled with tetrahydrofuran, stirring at a constant speed, adding triethylamine, stirring for 5min, placing in 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 ℃, preserving heat, reacting for 30h, preparing a mixed solution, and purifying to obtain a synergistic body;
2. a process for the continuous ammonification of o-phenylenediamine according to claim 1, wherein: in the step S1, the mol ratio of benzene, phosphorus trichloride and aluminum trichloride is controlled to be 1:1:1.2-1.3.
3. A process for the continuous ammonification of o-phenylenediamine according to claim 1, wherein: in the step S2, the volume ratio of the intermediate 1 to the triethylamine to the tetrahydrofuran is controlled to be 2.65mL to 2.15 to 2.2mL to 20mL, and the dosage of the decomplexer is 3 to 5 percent of the weight of the crude product.
4. A process for the continuous ammonification of o-phenylenediamine according to claim 1, wherein: the mol ratio of the o-dichlorobenzene to the liquid ammonia is controlled to be 1:5-10, and the dosage of the catalyst is 1-1.5 percent of the weight of the o-dichlorobenzene.
5. A process for the continuous ammonification of 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.
6. A process for the continuous ammonification of o-phenylenediamine according to claim 1, wherein: the decomplexing agent is any one of pyridine and picoline.
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| CN105037171B (en) * | 2015-06-08 | 2017-03-08 | 江阴市华亚化工有限公司 | A kind of o-dichlorohenzene prepares the synthetic method of o-phenylenediamine |
| CN107188905B (en) * | 2017-05-22 | 2019-05-24 | 东北石油大学 | A kind of amino phenolic group phosphorus ligand and its application in vinyl polymerization and oligomerisation |
| CN110218226A (en) * | 2019-07-02 | 2019-09-10 | 浙江扬帆新材料股份有限公司 | A kind of synthetic method of diphenyl phosphine chloride |
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