CN115417757A - Method for separating 4-chlorobenzophenone or benzophenone from benzophenone tail distillation waste - Google Patents
Method for separating 4-chlorobenzophenone or benzophenone from benzophenone tail distillation waste Download PDFInfo
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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Abstract
The invention discloses a method for separating 4-chlorobenzophenone or benzophenone from benzophenone tailing waste. 4-chlorobenzophenone with important value in the waste is separated and purified by the solid tailing waste generated in the production process of the benzophenone in an innovative simple batch washing mode. Putting the liquid tail distillation waste liquid of the benzophenone and the derivative into a reduced pressure distillation device with the pressure of 1.5 to 2.0KPa, and carrying out reduced pressure distillation under the condition of oil bath heating. The crude benzophenone product in the benzophenone tailing waste liquid can be preliminarily separated through the reduced pressure distillation operation, and then a good solvent and a poor solvent are added into the crude benzophenone product for further low-temperature recrystallization and purification, so that the high-purity benzophenone is obtained. High-temperature distillation treatment is avoided, separation and purification of the benzophenone solid waste are realized through simple batch washing and suction filtration operation, the investment cost of equipment and energy is reduced, and the recycling of resources is realized.
Description
Technical Field
The invention relates to a method for separating and purifying 4-chlorobenzophenone or benzophenone from benzophenone waste.
Background
Benzophenone derivatives are important organic chemical products and widely exist in natural products, materials, medicines and other bioactive molecules. Among them, 4-chlorobenzophenone is an important pharmaceutical active intermediate, and is commonly used as an intermediate for medicines and pesticides and a UV-curable coating and ink. Besides, benzophenone derivatives are widely used as radical photoinitiators in radical ultraviolet curing systems, such as coatings, inks, adhesives, and the like. Meanwhile, the benzophenone derivatives have wide application in biology and medicine, can be used as a unique medicinal chemical stent material to synthesize effective active components with antifungal, anti-HIV, antibacterial, antiviral and antioxidant effects. The benzophenone derivatives have wide market prospect and great commercial value, but are accompanied with the generation of a large amount of tailing waste in industrial production, if the generated tailing waste is not treated after being placed for a long time, not only the full utilization of resources is not realized, but also the serious problem of environmental pollution is caused. Therefore, it is necessary to explore the separation and purification of the tail distillation in the production of benzophenone derivatives.
The invention provides a method for separating and purifying benzophenone by using benzophenone tail fraction. Putting the mixed components of the tail distillation to be treated in a vacuum distillation device according to different boiling point values under different pressures, heating the oil bath to 140-160 ℃, and carrying out vacuum distillation treatment on the benzophenone liquid tail distillation waste liquid when the pressure of the vacuum distillation device is 1.5-2.0 KPa. The method can successfully preliminarily separate out a crude benzophenone product from the benzophenone liquid tail distillation waste liquid, and then obtain the high-purity benzophenone through one-step recrystallization treatment. The method not only solves the problem of recycling and treating the waste liquid of the tail distillation generated in the production process of the benzophenone and the derivatives thereof by a means of simpler, more convenient, more efficient and easier operation, but also solves the problem of serious environmental pollution caused by the tail distillation of the benzophenone liquid by using low-cost equipment and energy input.
The invention also provides a method for separating and purifying the 4-chlorobenzophenone from the benzophenone waste. The method comprises the steps of sequentially carrying out simple primary washing and secondary washing operations on the generated benzophenone waste, further carrying out reduced pressure suction filtration separation, and carrying out vacuum drying to complete separation and purification of the benzophenone waste and obtain the high-content 4-chlorobenzophenone. The method avoids high equipment and cost investment, and can complete the recovery and purification of the benzophenone waste material through batch washing, reduced pressure suction filtration and vacuum drying in sequence, namely the recovery and treatment of the benzophenone waste material are realized by a method which is simple in operation, energy-saving and environment-friendly, and the pollution problem of the benzophenone waste material to the environment is reduced.
Disclosure of Invention
The invention mainly aims to provide a method for separating and purifying 4-chlorobenzophenone from benzophenone waste.
The technical scheme of the invention is as follows:
a method for separating and purifying 4-chlorobenzophenone from benzophenone tailing waste comprises the following steps:
(1) Carrying out reduced pressure suction filtration on benzophenone tail distillation waste to be treated to remove residual waste liquid on the surface;
(2) Adding a first washing solvent into the solid waste after the suction filtration treatment, stirring, washing, and then carrying out vacuum filtration to obtain a crude product of the 4-chlorobenzophenone;
(3) And adding a second washing solvent into the crude product of the 4-chlorobenzophenone, stirring, washing, decompressing, filtering, and drying to obtain the 4-chlorobenzophenone.
In the step (1), the benzophenone tailing waste comprises 5-12% of benzophenone, 4-8% of 2-chlorobenzophenone, 50-66% of 4-chlorobenzophenone, 5-12% of 3-chlorobenzophenone and 10-20% of a mixture of 2,4 '-dichlorobenzophenone and 2,6' -dichlorobenzophenone.
The temperature of the reduced pressure filtration in the step (1) is 20 to 35 ℃, and the pressure of the reduced pressure filtration is-0.06 to-0.1 MPa.
The first washing solvent in the step (2) is one or a combination of more of petroleum ether and cyclohexane.
And (3) the second washing solvent is ethyl acetate.
The stirring speed in the steps (2) and (3) is controlled to be 400 to 600 r/min, the temperature of reduced pressure suction filtration is 20 to 35 ℃, and the pressure is-0.06 to-0.1 MPa.
The normal temperature drying is carried out under the vacuum degree of-0.08 to-0.1 MPa.
The content of 4-chlorobenzophenone in the benzophenone waste can be improved to more than 90 percent by the separation and purification method. The method does not need temperature-resistant and pressure-resistant equipment and high waste treatment cost investment, can complete separation and purification of the benzophenone waste through simple batch washing and reduced pressure suction filtration operation, obtains high-content 4-chlorobenzophenone, and has the advantages of energy conservation, environmental protection, simplicity, convenience, high efficiency, high operability and the like.
The invention also provides a method for separating and purifying benzophenone in benzophenone tail distillation, which comprises the steps of carrying out reduced pressure distillation on the tail distillation waste material to be treated under the heating condition, collecting fractions to obtain a crude benzophenone product, adding a good solvent and a poor solvent into the crude benzophenone product for recrystallization, and washing and drying the recrystallized product to obtain the benzophenone.
The content of benzophenone in the tailing waste is 50-60%; the content of the 2-chlorobenzophenone is 10-14%; the content of 4-chlorobenzophenone is 10-15%; 5-10% of 3-chlorobenzophenone and 1-5% of others.
Under the condition of normal pressure, the boiling point of the benzophenone is above 300 ℃, so the purpose of reducing the boiling point of the benzophenone is achieved by reducing the pressure during distillation. The boiling points of the benzophenone under different pressures are measured by using a vapor pressure curve simulated by a Trouton-Hildebrand-Everett rule, and the boiling point-pressure conversion curve of the benzophenone is obtained as shown in a table 1 and shown in a figure 2; and then, combining with actual conditions, selecting to carry out reduced pressure distillation operation at 140-160 ℃ under the pressure of 1.5-2.0 KPa.
TABLE 1 simulated boiling points of benzophenone and its derivatives at different pressures
In the recrystallization process, by trying the recrystallization effect of some common solvents, one or more of ethyl acetate and methanol are selected as good solvents.
The poor solvent is one or the combination of more of petroleum ether and dichloromethane.
Wherein the volume ratio of the good solvent to the poor solvent in the recrystallization is 1 to 5 times. The temperature is 0 to-20 ℃.
The reduced pressure distillation and recrystallization operation of the benzophenone liquid tailing waste in the step can improve the content of the benzophenone in the tailing mixture to about 99 percent by the separation and purification method.
The invention has the following beneficial effects:
the invention discloses a method for separating and purifying 4-chlorobenzophenone from benzophenone waste for the first time. The separation and purification method does not need temperature-resistant and pressure-resistant equipment and high cost investment, and can realize separation and purification of benzophenone waste by selecting appropriate primary washing solvent and secondary washing solvent to carry out simple batch washing, reduced pressure suction filtration and vacuum drying operation, thereby obtaining the high-content 4-chlorobenzophenone. The method not only can separate and purify the 4-chlorobenzophenone with high content from the benzophenone waste, but also avoids the problems of resource waste and environmental pollution caused by the waste generated in the production process.
The invention discloses a method for separating and purifying benzophenone by using benzophenone tail fraction for the first time. Adjusting the pressure of a reduced pressure distillation device to 1.5 to 2.0KPa according to different boiling points under different pressures, and carrying out corresponding reduced pressure distillation operation at 140 to 160 ℃. In the vacuum distillation device, the vacuum distillation method can be adopted to carry out primary separation on the benzophenone in the benzophenone liquid tail mixture. The obtained crude product of the benzophenone is recrystallized in one step to obtain the benzophenone with the content of 99 percent. The method is simple and convenient to operate, high in separation degree and easy to industrialize, avoids resource waste and reduces serious pollution of benzophenone liquid tail distillation waste liquid to the environment.
Drawings
FIG. 1: the separation and purification device for benzophenone liquid tail distillation waste material is characterized by that it includes (1) thermometer, 2. Thorn-type distillation column, 3. Oil bath pot, 4. Straight condenser tube, 5. Vacuum pump, 6. Trident swallow tail tube and 7. Vacuum pump.
FIG. 2: boiling point-pressure conversion curve of benzophenone.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Instruments and reagents:
SHZ-E model circulating water type vacuum pump (Shanghai Rongyasheng chemical instruments factory); a 2YZ-4A rotary vane type vacuum oil pump (Winghao vacuum equipment factory in Linhai City); DZF-6020B vacuum drying oven (Shanghai Qixin scientific instruments Co., ltd.); EB2005A electronic balance; ethyl Acetate (AR).
The benzophenone solid tailing waste used in the embodiment is obtained from Utility friend source industry Co., ltd, and the physicochemical property is that the content of the benzophenone is about 7.71%; the content of 2-chlorobenzophenone is about 6.24%; the content of 4-chlorobenzophenone is about 66.52%; about 7.69% 3-chlorobenzophenone; the total content of other 2,4 '-dichlorobenzophenone, 2,6' -dichlorobenzophenone, and the like is about 11.84%.
The separation and purification device for benzophenone liquid tail distillation waste material mainly includes reduced pressure distillation device formed from thermometer, thorn-type distillation column, oil bath pot, straight condenser tube, vacuum meter, trifurcate swallow tail tube and vacuum pump, in the described separation and purification device a thorn-type distillation column is mounted between distillation flask and thermometer, as shown in figure 1.
In this example, the benzophenone liquid tailing waste mixture was obtained from Utility City, utility industries, inc., and contained components including benzophenone, 2-chlorobenzophenone, 4-chlorobenzophenone, 3-chlorobenzophenone and others in amounts such that the content of the corresponding components was about 50.23% for benzophenone, respectively; the content of 2-chlorobenzophenone is about 13.73%; the content of 4-chlorobenzophenone is about 14.30%; about 9.57% 3-chlorobenzophenone; the other mixture was about 12.17%.
Example 1
The boiling point values of benzophenone in the tailing waste liquid mixture at different pressures were simulated by the Trouton-Hildebrand-Everett rule. The reduced pressure distillation at 150 ℃ is selected by combining the simulation value, and the pressure of the reduced pressure distillation is 1.8KPa.
Example 2
And putting 180g of the benzophenone liquid tailing waste mixture into a reduced pressure distillation device, carrying out reduced pressure distillation at 150 ℃, and collecting distillate liquid according to a simulated vapor pressure curve. After distillation under reduced pressure, 91.6g of distillate was collected as a yellow oil. Wherein, the content of the benzophenone is about 81.54 percent; the content of 2-chlorobenzophenone is about 3.84%; the content of 4-chlorobenzophenone is about 5.93%; the content of 3-chlorobenzophenone is 6.48%; the other mixture was about 2.21%.
Example 3
In order to solve the technical effect of example 2, the present application further purifies benzophenone by recrystallization, and 30mL of acetone is added to the distillate to fully dissolve the distillate in the acetone. Then, 6mL of cyclohexane is slowly added along the wall of the container, the mixture is kept stand at minus 10 ℃ to minus 20 ℃ for recrystallization, and the recrystallized crystals are sequentially filtered and vacuum-dried at normal temperature. The results show that no benzophenone is precipitated under the matching use of the good solvent and the poor solvent.
Example 4
And (3) selecting methanol and dichloromethane to carry out recrystallization operation of the benzophenone. 30mL of methanol was added to the distillate to dissolve the distillate sufficiently in methanol. Then, slowly adding 6mL of dichloromethane along the wall of the container, standing the mixture at the temperature of minus 10 ℃ to minus 20 ℃, recrystallizing the mixture, and sequentially filtering and drying the recrystallized crystals in vacuum at normal temperature. The result shows that the content of the benzophenone separated and purified is about 95.30 percent under the condition of matching the good solvent and the poor solvent.
Example 5
Benzophenone was further purified, and 30mL of ethyl acetate was added to the distillate to sufficiently dissolve the distillate in ethyl acetate. Then, slowly adding 10mL of petroleum ether along the wall of the container, standing at-10 to-20 ℃, recrystallizing, sequentially filtering the recrystallized crystal, and drying in vacuum at normal temperature. The result shows that the content of the benzophenone separated and purified under the matching use of the good solvent and the poor solvent is about 99.0 percent.
Example 6
Performing reduced pressure filtration separation on 100g of benzophenone tailing waste in a reduced pressure filtration device at the temperature of between 20 and 35 ℃ and the pressure of between-0.06 and-0.1 MPa, and removing residual waste liquid on the surface. The solid waste after completion of suction filtration was 69.78g, and the properties were changed from yellow solid to white solid. After the treatment of one-time vacuum filtration, the content of the 4-chlorobenzophenone is improved. Wherein, the content of the benzophenone is about 4.07%; the content of 2-chlorobenzophenone is about 2.28%; the content of 4-chlorobenzophenone is about 86.03%; the total content of other 2,4 '-dichlorobenzophenone, 2,6' -dichlorobenzophenone, and the like mixtures was about 7.62%.
Example 7
Aiming at the technical effect of the embodiment 5, toluene (30 mL) is added into the filtered white solid, the mixture is stirred for 5min at the rotating speed of 600 r/min, and then the reduced pressure filtration is further carried out at the temperature of 20 to 35 ℃ and the pressure of-0.06 to-0.1 MPa; and adding methanol (3 mL) into the obtained solid, stirring for 5min at 600 r/min, carrying out vacuum filtration at the temperature of 20-35 ℃ and the pressure of-0.06-0.1 MPa, and carrying out vacuum drying on the obtained solid at normal temperature, wherein the content of the 4-chlorobenzophenone is not improved.
Example 8
Aiming at the technical effect of the embodiment 5, petroleum ether (30 mL) is added into the filtered white solid, the mixture is stirred for 5min at the rotating speed of 600 r/min, and then the reduced pressure filtration is further carried out at the temperature of 20 to 35 ℃ and the pressure of-0.06 to-0.1 MPa; and adding ethyl acetate (3 mL) into the obtained solid, stirring at 600 r/min for 5min, carrying out vacuum filtration at the temperature of 20 to 35 ℃ and the pressure of-0.06 to-0.1 MPa, and carrying out vacuum drying on the obtained solid at normal temperature to obtain the 4-chlorobenzophenone with the content of 98%.
Example 9
Adding cyclohexane (30 mL) into the filtered white solid, stirring at the rotating speed of 600 r/min for 5min, and carrying out further reduced pressure filtration at the temperature of 20-35 ℃ and the pressure of-0.06-0.1 MPa; and adding ethyl acetate (3 mL) into the obtained solid, stirring at 600 r/min for 5min, carrying out vacuum filtration at the temperature of 20 to 35 ℃ and the pressure of-0.06 to-0.1 MPa, and carrying out vacuum drying on the obtained solid at normal temperature to obtain the 4-chlorobenzophenone with the content of 95%.
The above-described embodiments are merely preferred technical solutions of the present invention, and should not be construed as limiting the present invention, and the embodiments and features in the embodiments in the present application may be arbitrarily combined with each other without conflict. The protection scope of the present invention is defined by the claims, and includes equivalents of technical features of the claims. I.e., equivalent alterations and modifications within the scope hereof, are also intended to be within the scope of the invention.
Claims (10)
1. The method for separating 4-chlorobenzophenone from benzophenone tailing waste is characterized by comprising the following steps:
(1) Carrying out reduced pressure suction filtration on benzophenone tailing waste to be treated to remove residual waste liquid on the surface;
(2) Adding a first washing solvent into the solid waste after the suction filtration treatment, stirring, washing, and then carrying out vacuum filtration to obtain a crude product of the 4-chlorobenzophenone;
(3) And adding a second washing solvent into the crude product of the 4-chlorobenzophenone, stirring, washing, decompressing, filtering, and drying to obtain the 4-chlorobenzophenone.
2. The method for separating 4-chlorobenzophenone from the benzophenone waste from the step (1) according to claim 1, wherein the benzophenone waste from the step (1) comprises 5 to 12% of benzophenone, 4 to 8% of 2-chlorobenzophenone, 50 to 66% of 4-chlorobenzophenone, 5 to 12% of 3-chlorobenzophenone, and 10 to 20% of a mixture of 2,4 '-dichlorobenzophenone and 2,6' -dichlorobenzophenone.
3. The method for separating 4-chlorobenzophenone from benzophenone tailing waste according to claim 1, wherein the temperature of the vacuum filtration in the step (1) is 20 to 35 ℃, and the pressure of the vacuum filtration is-0.06 to-0.1 MPa.
4. The method for separating 4-chlorobenzophenone from benzophenone tailing waste according to claim 1, wherein the first washing solvent in step (2) is one or more of petroleum ether and cyclohexane, and the second washing solvent in step (3) is ethyl acetate;
the stirring speed in the steps (2) and (3) is controlled to be 400 to 600 r/min, the temperature of reduced pressure suction filtration is 20 to 35 ℃, the pressure is-0.06 to-0.1 MPa, and the drying in the step (3) is carried out under the vacuum degree of-0.08 to-0.1 MPa.
5. The method for separating the benzophenone from the benzophenone tailing waste is characterized by comprising the steps of carrying out reduced pressure distillation on the tailing waste to be treated under the heating condition, collecting fractions to obtain a crude benzophenone product, adding a good solvent and a poor solvent into the crude benzophenone product for recrystallization, washing and drying the recrystallized product to obtain the benzophenone.
6. The method for separating benzophenone from the waste material of benzophenone rectification of claim 5, characterized in that the waste material of benzophenone rectification to be treated is distilled under reduced pressure under heating condition, the distillate is collected to obtain crude product of benzophenone, the crude product of benzophenone is added with good solvent and poor solvent to be recrystallized, the recrystallized product is washed and dried to obtain benzophenone.
7. The method for separating benzophenone from the waste material of benzophenone tailing distillation of claim 6, wherein the content of benzophenone in the waste material of tailing distillation is 50-60%; the content of the 2-chlorobenzophenone is 10-14%; the content of 4-chlorobenzophenone is 10-15%; 5-10% of 3-chlorobenzophenone and 1-5% of others.
8. The method for separating benzophenone from benzophenone tailing waste material according to claim 6, wherein the temperature is 140 to 160 ℃ and the pressure is 1.5 to 2.0KPa in the vacuum distillation process.
9. The method for separating benzophenone from the benzophenone tail distillation waste material as claimed in claim 6, wherein the good solvent is one or more of ethyl acetate and methanol;
the poor solvent is one or the combination of more of petroleum ether and dichloromethane.
10. The method for separating benzophenone from the benzophenone tailing waste material as claimed in claim 6, wherein the volume ratio of the good solvent to the poor solvent in the recrystallization is 1 to 5 times; the temperature during recrystallization is 0 to-20 ℃.
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