CN113045440A - Preparation method of 1-aminoanthraquinone - Google Patents

Preparation method of 1-aminoanthraquinone Download PDF

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CN113045440A
CN113045440A CN202110353925.4A CN202110353925A CN113045440A CN 113045440 A CN113045440 A CN 113045440A CN 202110353925 A CN202110353925 A CN 202110353925A CN 113045440 A CN113045440 A CN 113045440A
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aminoanthraquinone
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吴秀荣
叶友余
黄华南
胡华南
王卫杰
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Jiujiang Shanshui Technology Co ltd
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    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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Abstract

The preparation method of 1-aminoanthraquinone of the invention uses nickel carbonyl loaded by superparamagnetic nano particles as catalyst, 1-nitroanthraquinone as reaction substrate, hydrogen is introduced after adding solvent, and reaction is carried out for 2-8h at 60-80 ℃ and 0.3-0.5 MPa; then adding a magnetic field to the reaction product to recover the catalyst, and carrying out post-treatment to obtain 1-aminoanthraquinone; wherein: the mass of the catalyst is 0.003 time of that of the 1-nitroanthraquinone, and the mass ratio of the 1-nitroanthraquinone to the solvent is 15: 4. The synthesis process of the 1-aminoanthraquinone is simple, high in selectivity, environment-friendly, low in equipment investment and suitable for industrial production. The nickel carbonyl loaded by the superparamagnetic nano particles has moderate catalytic activity, can selectively reduce nitro, avoids over reduction of carbonyl, has high yield of 1-aminoanthraquinone, can be collected and recycled by an external magnetic field, and can be reused for at least 5 times.

Description

Preparation method of 1-aminoanthraquinone
Technical Field
The invention relates to a preparation method of 1-aminoanthraquinone, in particular to a method for preparing 1-aminoanthraquinone by taking nickel carbonyl loaded by superparamagnetic nano particles as a catalyst, which is green and efficient, and belongs to the technical field of organic synthesis.
Background
The 1-aminoanthraquinone is an important intermediate for synthesizing anthraquinone series dyes, has the widest application and the largest consumption, and plays an extremely important role in the dye industry. In recent years, with the annual increase of environmental protection requirements, the production of anthraquinone series dyes is reduced or stopped at home and abroad. Therefore, the improvement of the process, the reduction of pollution, the improvement of quality and the reduction of cost are the problems which are urgently needed to be solved for the production of the 1-aminoanthraquinone.
The process for producing 1-aminoanthraquinone mainly comprises a sodium sulfide method and a sulfonation ammonolysis method. The method for refining the 1-aminoanthraquinone by the sulfuration subtraction method is a mainstream method for producing the 1-aminoanthraquinone in China, the I-aminoanthraquinone synthesized by the method has high impurity content and needs a complicated purification process, the refining method mainly comprises a sodium hydrosulfite method, a sublimation method, a rectification method and a sulfuric acid method, the process flow is long, three wastes are more, and the environmental pollution is serious. Therefore, the search for an environment-friendly, economical and green process is an inevitable way to produce 1-aminoanthraquinone. Currently, the green processes which are relatively concerned mainly comprise 2 kinds of processes, namely an ammonolysis method and a catalytic hydrogenation reduction method. The ammonolysis method requires high temperature and high pressure, and has potential safety hazard. In comparison, the catalytic hydrogenation reduction method has advantages over the ammonolysis method in terms of operation and equipment safety, especially, the high temperature has great influence on the dye color, in addition, the reaction time is long, the temperature is high, so that the side reactions are more, some by-products have serious corrosion to the equipment, and the equipment investment is increased. Compared with an alkali sulfide method, the catalytic hydrogenation reduction method does not generate a large amount of alkaline sulfur-containing waste liquid which is difficult to treat, and the product yield is higher. However, the catalytic hydrogenation method has obvious disadvantages in actual production, such as large catalyst usage, low efficiency, difficult recovery and treatment, high cost, and difficult solution of technical problems of catalyst screening, activity, selectivity and the like, which are still not broken through. Chinese patent (201010596904.7) discloses a method for preparing high-purity 1-aminoanthraquinone by catalytic hydrogenation, which comprises the steps of taking 1-nitroanthraquinone as a raw material, taking N, N-dimethylformamide or xylene as a solvent, and adding a catalyst for hydrogenation reduction reaction. Wherein, the active carbon catalyst comprises the following components: the doping of one or more of Pd, Ni, Co, Cu, Ru and Pt, including the non-supported form, the supported form and the amorphous form, although the product purity is up to 99 percent and the yield is up to more than 98 percent, the technical method only remains in a small test stage and has no record of industrialized mass production. And moreover, the Pd/C catalyst has too high reaction activity, so that the reaction selectivity is reduced, carbonyl in the structure is also reduced, and the 1-aminoanthraquinone with corresponding purity can be obtained after the reduction solution is oxidized. In addition, the organic solvent such as N, N-dimethylformamide or xylene causes pollution to air or surface water to some extent. Therefore, it is important to develop a catalytic system with mild catalytic reaction activity and environmental protection.
In recent years, the application of a superparamagnetic nanoparticle supported catalyst is an emerging green catalytic reaction technology. Based on the above, the invention provides a nickel carbonyl catalyst loaded by superparamagnetic nano particles, which is applied to the production of 1-aminoanthraquinone. Compared with the phase process of Pd/C catalytic reduction, the nickel carbonyl loaded by the superparamagnetic nano particles has moderate catalytic activity, the reaction process is easy to control, the high-purity 1-aminoanthraquinone can be obtained without an oxidation step after reduction, the reaction temperature is low, the yield is high, the catalyst is simple and efficient to recover, an external magnetic field can be recovered, and the catalyst can be repeatedly used.
Disclosure of Invention
The invention aims to adopt a superparamagnetic nanoparticle supported catalyst for green catalytic synthesis of 1-aminoanthraquinone.
The invention relates to a preparation method of 1-aminoanthraquinone, which adopts nickel carbonyl loaded by superparamagnetic nano particles as a catalyst and 1-nitroanthraquinone as a reaction substrate to obtain the 1-aminoanthraquinone through catalytic hydrogenation, and comprises the following specific processes:
using nickel carbonyl loaded by superparamagnetic nano particles as a catalyst, 1-nitroanthraquinone as a reaction substrate, adding a solvent, introducing hydrogen, and reacting for 2-8h at the temperature of 60-80 ℃ and under the pressure of 0.3-0.5 MPa; then adding a magnetic field to the reaction product to recover the catalyst, and then carrying out acidification, cooling, filter pressing and drying treatment to obtain 1-aminoanthraquinone; wherein: the mass of the catalyst is 0.003 time of that of the 1-nitroanthraquinone, and the proportion of the 1-nitroanthraquinone to the solvent is 1 mol/80L;
the structural formula of the superparamagnetic nanoparticle-loaded nickel carbonyl is as follows:
Figure 562130DEST_PATH_IMAGE001
the preparation process of the superparamagnetic nanoparticle loaded nickel carbonyl comprises the following steps:
3-chloropropyltriethoxysilane and imidazole are dispersed in anhydrous toluene according to the molar ratio of 1: 1, reflux reaction is carried out for 2h under the protection of nitrogen, and then the intermediate of siloxane imidazole salt is obtained through recrystallization;
Fe3O4/SiO2ultrasonically dispersing solid particles in anhydrous toluene for 10min, dropwise adding a toluene solution of a siloxane imidazolium salt intermediate under the protection of nitrogen, carrying out reflux stirring reaction for 10 h, washing the solid product collected by a magnet with anhydrous ethanol for three times, and carrying out vacuum drying to obtain siloxane magnetic solid particles; wherein Fe3O4/SiO2The mass ratio of the solid particles to the intermediate of the siloxane imidazolium salt is 3: 1;
ultrasonically dispersing siloxane magnetic solid particles into absolute ethyl alcohol for 10min, dropwise adding an ethanol solution of 2-chloroethyl diphenylphosphine under the protection of nitrogen, carrying out reflux stirring reaction for 12h, washing a solid product collected by a magnet for three times by the absolute ethyl alcohol, and carrying out vacuum drying to obtain load type siloxane magnetic solid particles; wherein the mass ratio of the siloxane magnetic solid particles to the 2-chloroethyl diphenylphosphine is 1: 5;
dispersing the loaded siloxane magnetic solid particles and nickel tetracarbonyl in absolute ethyl alcohol according to the mass ratio of 35: 1, carrying out reflux stirring reaction for 3-4h under the protection of nitrogen, cooling the product to 0-10 ℃, filtering, washing a filter cake for 2 times by using deionized water and absolute ethyl alcohol respectively, and carrying out vacuum drying to obtain the nickel carbonyl loaded by the superparamagnetic nano particles.
The solvent is water, methanol and ethanol, tetrahydrofuran, glycerol or PEG 400.
The reaction equation of the invention is as follows:
Figure 417960DEST_PATH_IMAGE002
the invention has the beneficial effects that:
the synthesis process of the 1-aminoanthraquinone is simple, high in selectivity, environment-friendly, low in equipment investment and suitable for industrial production. The nickel carbonyl loaded by the superparamagnetic nano particles has moderate catalytic activity, can selectively reduce nitro, avoids over reduction of carbonyl, does not need oxidation after reaction, and can obtain high-quality 1-aminoanthraquinone only by simple post-treatment, the yield is high, the catalyst can be collected and recovered by an external magnetic field, and the catalyst can be reused at least for 5 times, and the activity of the catalyst is not obviously reduced.
Detailed Description
Example 1
Preparation of superparamagnetic nanoparticle supported nickel carbonyl catalyst
Imidazole (68 g, 1 mol), 3-chloropropyltriethoxysilane (240 mL,1 mol), 500 mL toluene were weighed separately into a three-necked flask, N2Refluxing and stirring for reaction for 2h under protection, and recrystallizing to obtain a siloxane imidazolium salt intermediate;
30g of Fe are taken3O4/SiO2Adding the solid particles into a reaction container, adding 500 mL of anhydrous toluene, performing ultrasonic treatment for 10 minutes, dissolving 10 g of siloxane imidazole salt into 200mL of anhydrous toluene after the ultrasonic treatment is finished, and then dropwise adding the solution into the reaction system, wherein N is2Carrying out reflux stirring reaction for 10 h under protection, collecting by using a magnet after the reaction is finished, washing for three times by using ethanol, and drying in vacuum to obtain siloxane magnetic solid particles;
4g of siloxane magnetic solid particles are put into a reaction vessel, 100 mL of absolute ethyl alcohol is added, ultrasonic treatment is carried out for 10 minutes, 160 mmol (20 g) of 2-chloroethyl diphenylphosphine is dissolved by 400mL of absolute ethyl alcohol after the ultrasonic treatment is finished, then the solution is dripped into the reaction system, and N is added2Protected down refluxReacting for 12 hours, collecting by using a magnet after the reaction is finished, washing for three times by using ethanol, and drying in vacuum to obtain loaded siloxane magnetic solid particles, wherein the mass of the finally obtained gray nano particles is 280 g;
adding 280 g of load type siloxane magnetic solid particles and 8 g of nickel tetracarbonyl into 200mL of absolute ethyl alcohol, mechanically stirring and refluxing for 4h at 80 ℃ under the protection of nitrogen, cooling the reaction solution to 0-10 ℃ by using an ice water bath, filtering, washing filter cakes for 2 times by using deionized water and absolute ethyl alcohol respectively, and drying in vacuum to obtain the nickel carbonyl loaded with the superparamagnetic nano particles, wherein the yield is 95% calculated by nickel. Through elemental analysis, the effective loading amount of the nickel carbonyl loaded on the superparamagnetic nano particles is 0.86 mmol/g.
Example 2
Preparation of 1-aminoanthraquinones
Adding solvents of methanol (40 kg) and 1-nitroanthraquinone (150 kg) into a 1L autoclave in sequence, adding 450 g of superparamagnetic nanoparticle supported nickel carbonyl catalyst under stirring, replacing for 3 times with nitrogen, replacing for 3 times with hydrogen, introducing hydrogen, keeping the pressure at 0.35-0.4Mpa, stirring, heating to 60 ℃, reacting for 8 hours, and sampling and detecting. Cooling to 40-50 ℃, externally adding a magnetic field to recover the catalyst, transferring the reaction solution to an acidification kettle, dropwise adding 80 kg of 15wt% hydrochloric acid to adjust the pH value to 5.5-6.0, stirring and cooling to room temperature, carrying out filter pressing, and carrying out vacuum drying on the obtained 1-aminoanthraquinone wet product at 85-90 ℃ for 8 hours to obtain 129kg of 1-aminoanthraquinone, wherein the yield is 98%, and the purity is 99.8% (HPLC detection).

Claims (3)

1. A preparation method of 1-aminoanthraquinone is characterized in that: the preparation method comprises the following steps of using nickel carbonyl loaded by superparamagnetic nano particles as a catalyst, using 1-nitroanthraquinone as a reaction substrate, and carrying out catalytic hydrogenation to obtain 1-aminoanthraquinone, wherein the specific process comprises the following steps:
using nickel carbonyl loaded by superparamagnetic nano particles as a catalyst, 1-nitroanthraquinone as a reaction substrate, adding a solvent, introducing hydrogen, and reacting for 2-8h at the temperature of 60-80 ℃ and under the pressure of 0.3-0.5 MPa; then adding a magnetic field to the reaction product to recover the catalyst, and then carrying out acidification, cooling, filter pressing and drying treatment to obtain 1-aminoanthraquinone; wherein: the mass of the catalyst is 0.003 time of that of the 1-nitroanthraquinone, and the mass ratio of the 1-nitroanthraquinone to the solvent is 15: 4;
the structural formula of the superparamagnetic nanoparticle-loaded nickel carbonyl is as follows:
Figure 387596DEST_PATH_IMAGE001
。
2. the process according to claim 1, wherein the reaction is carried out in the presence of a catalyst selected from the group consisting of: the preparation process of the superparamagnetic nanoparticle loaded nickel carbonyl comprises the following steps:
3-chloropropyltriethoxysilane and imidazole are dispersed in anhydrous toluene according to the molar ratio of 1: 1, reflux reaction is carried out for 2h under the protection of nitrogen, and then the intermediate of siloxane imidazole salt is obtained through recrystallization;
Fe3O4/SiO2ultrasonically dispersing solid particles in anhydrous toluene for 10min, dropwise adding a toluene solution of a siloxane imidazolium salt intermediate under the protection of nitrogen, carrying out reflux stirring reaction for 10 h, washing the solid product collected by a magnet with anhydrous ethanol for three times, and carrying out vacuum drying to obtain siloxane magnetic solid particles; wherein Fe3O4/SiO2The mass ratio of the solid particles to the intermediate of the siloxane imidazolium salt is 3: 1;
ultrasonically dispersing siloxane magnetic solid particles into absolute ethyl alcohol for 10min, dropwise adding an ethanol solution of 2-chloroethyl diphenylphosphine under the protection of nitrogen, carrying out reflux stirring reaction for 12h, washing a solid product collected by a magnet for three times by the absolute ethyl alcohol, and carrying out vacuum drying to obtain load type siloxane magnetic solid particles; wherein the mass ratio of the siloxane magnetic solid particles to the 2-chloroethyl diphenylphosphine is 1: 5;
dispersing the loaded siloxane magnetic solid particles and nickel tetracarbonyl in absolute ethyl alcohol according to the mass ratio of 35: 1, carrying out reflux stirring reaction for 3-4h under the protection of nitrogen, cooling the product to 0-10 ℃, filtering, washing a filter cake for 2 times by using deionized water and absolute ethyl alcohol respectively, and carrying out vacuum drying to obtain the nickel carbonyl loaded by the superparamagnetic nano particles.
3. The process according to claim 1, wherein the reaction mixture comprises: the solvent is water, methanol and ethanol, tetrahydrofuran, glycerol or PEG 400.
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN114478616A (en) * 2022-01-12 2022-05-13 湖北江瀚新材料股份有限公司 3- (N-imidazole) propyl triethoxysilane and synthesis method thereof
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