CN118634758B - A method for treating residual hydrogen peroxide in phenol hydroxylation reaction liquid - Google Patents
A method for treating residual hydrogen peroxide in phenol hydroxylation reaction liquid Download PDFInfo
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Abstract
本发明提供了一种苯酚羟基化反应液中残余过氧化氢的处理方法，苯酚与过氧化氢在催化剂作用下，反应生成含有水、苯酚、苯二酚、焦油、少量过氧化氢和醌类物质的苯酚羟基化反应液，向所述苯酚羟基化反应液中加入如式Ⅱ所示的化合物，并在60~80℃下反应0.5~1h。本发明的处理方法利用式Ⅱ所示的化合物所具有的还原性、水溶性和高沸点的特点，避免了处理过程中分解产氧，无燃爆风险，符合本质安全的要求。
The present invention provides a method for treating residual hydrogen peroxide in a phenol hydroxylation reaction liquid, wherein phenol and hydrogen peroxide react under the action of a catalyst to generate a phenol hydroxylation reaction liquid containing water, phenol, hydroquinone, tar, a small amount of hydrogen peroxide and quinone substances, a compound as shown in formula II is added to the phenol hydroxylation reaction liquid, and the reaction is carried out at 60-80° C. for 0.5-1 h. The treatment method of the present invention utilizes the characteristics of reducibility, water solubility and high boiling point of the compound shown in formula II, avoids decomposition and oxygen production during the treatment process, has no risk of combustion and explosion, and meets the requirements of intrinsic safety.
Description
Technical Field
The invention relates to the technical field of a preparation method of benzenediol, in particular to a treatment method of residual hydrogen peroxide in a phenol hydroxylation reaction liquid.
Background
Catechol and hydroquinone are two important intermediate products, and have wide application, and the catechol can be used for synthesizing spice and medical products such as vanillin, (new) heliotropin and the like, and the hydroquinone can be used as polymerization inhibitor, rubber antioxidant, antioxidant and the like. The majority of catechol and hydroquinone sold in the market at present are prepared by the hydroxylation reaction of phenol and hydrogen peroxide, and mainly comprise a UBE method, a Rhone-Poulenc method, a Brichima method, an Enichem method and the like. The Japanese UBE process uses sulfuric acid as catalyst and has high requirement on equipment material, the French Rhone Poulenc process uses HClO 4/H3PO4 as catalyst, the single pass conversion rate of phenol is lower and is only 5%, the Brichima process uses iron catalyst, the safety risk is higher, the Italian Enichem process replaces Brichima process, the prior mainstream production process uses titanium-silicon molecular sieve (TS-1) as catalyst, and the reaction of 27.5% hydrogen peroxide and phenol is carried out to generate o/hydroquinone, the reaction condition is mild, and the selectivity of the benzenediol is more than 90%.
The hydroxylation reaction of phenol and hydrogen peroxide has obvious tailing effect, namely the lower the concentration of hydrogen peroxide is, the slower the reaction speed is, the hydrogen peroxide is difficult to consume completely, so the conversion rate of the hydrogen peroxide in the normal reaction process is usually maintained between 97 and 99 percent, and the hydroxylation reaction liquid contains 500 to 2000ppm of hydrogen peroxide. If the reaction solution containing 500-2000ppm hydrogen peroxide is not treated and enters a subsequent rectification system, the following two risks are brought about, namely 1) the reaction solution is easy to accumulate in a tower kettle with higher temperature and the like due to the higher boiling point of the hydrogen peroxide, and organic peroxide is easy to form after long-time heating. In the heating process, hydrogen peroxide can be decomposed to generate oxygen, the oxygen can form explosive mixture with organic solvents such as acetone or methanol in the reaction liquid, and explosion is very easy to occur when exposed fire or static electricity is encountered, and 2) quinone substances such as p-benzoquinone and o-benzoquinone exist in the hydroxylation reaction liquid, and the substances are easy to react with residual hydrogen peroxide to generate tar, so that the subsequent separation is plagued.
In order to consume the low concentration hydrogen peroxide in the reaction solution, patent CN114225933B discloses a manganese oxide catalyst for hydrogen peroxide decomposition and a preparation method thereof, after mixing a mixed solution of metal salt and manganese salt with citric acid and gel successively, heating to obtain the manganese oxide catalyst, wherein the decomposition removal rate of hydrogen peroxide with the initial concentration of 1000 ppm in water within 15min is close to 100 percent, suzan A and the like (Suzan A. Ali, J. Mater. Sci. Technol, vol. 20, no. 1,2004, 55-58) develop a novel cobalt oxide-copper oxide catalyst loaded by alumina and used for decomposing hydrogen peroxide, the initial hydrogen peroxide concentration is 0.73 percent, and the hydrogen peroxide can be decomposed in 2 hours under the conditions of normal pressure and 30 ℃. Patent CN106140148B discloses a hydrogen peroxide decomposition catalyst which consists of a mixture of oxides of metals of groups IVB, VIB, IB and IIIA and is applied to a reaction liquid of epoxidation of 3-chloropropene and hydrogen peroxide, and the concentration of hydrogen peroxide in the epoxidation reaction liquid is reduced from 0.508% to 0.021% at 35 ℃ within 30 min.
The strategy of the patent technology is to decompose residual hydrogen peroxide, but the hydrogen peroxide is decomposed to generate oxygen, the oxygen is easy to form an explosive mixture with combustible liquid, methanol or acetone is mostly adopted as a solvent in hydroxylation reaction liquid of phenol and hydrogen peroxide, and the hydroxylation reaction liquid is a class-A liquid, has a wider explosion limit, and has a larger potential safety hazard once encountering oxygen.
Disclosure of Invention
In order to overcome the two problems that residual hydrogen peroxide in the phenol hydroxylation reaction in the prior art is easy to cause decomposition and oxygen production and tar generation, the invention provides a treatment method of residual hydrogen peroxide in the phenol hydroxylation reaction liquid, and the influence of the residual peroxide on subsequent products caused by the direct entering of the rectification system is avoided.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
According to the method for treating residual hydrogen peroxide in the phenol hydroxylation reaction liquid, phenol and hydrogen peroxide react under the action of a catalyst to generate the phenol hydroxylation reaction liquid containing water, phenol, benzenediol, tar, a small amount of hydrogen peroxide and quinone substances, a compound shown as a formula II is added into the phenol hydroxylation reaction liquid, and the reaction is carried out for 0.5-1 h at 60-80 ℃;
II (II)
Wherein R is selected from H or CH 3、C2H5.
The phenol hydroxylation reaction liquid is prepared from 10-20% of water, 25-35% of phenol, 30-45% of methanol, 15-20% of benzenediol, 1-5% of tar, 0.05-0.2% of hydrogen peroxide and 0.005-0.015% of quinone substances. In some more specific embodiments, TS-1 may be used as a catalyst, phenol and hydrogen peroxide as reaction materials, and methanol as a reaction solvent, at a reaction temperature of about 60 ℃ for about 1.5 hours.
In some specific embodiments, the mass ratio of the phenol hydroxylation reaction solution to the compound shown in the formula II is (100-200): 1, such as 110,160,170,180,190, and preferably (120-150): 1, such as 125:1,130:1,135:1,140:1,145:1.
The treatment method of the invention can effectively consume hydrogen peroxide in the phenol hydroxylation reaction liquid to generate water by utilizing the reducibility of the compound shown in the formula II, avoid the decomposition and oxygen production, have no explosion risk, meet the requirement of intrinsic safety, and simultaneously, can react with p-benzoquinone in the reaction liquid to generate hydroquinone by utilizing the reducibility characteristic of the phosphite ester and the hydroxylation reaction liquid, and can convert tar into a product, thereby changing waste into valuable. The sulfonic acid group in the compound shown in the formula II has certain water solubility, can be dissolved in phenol hydroxylation reaction liquid, can generate homogeneous reaction with hydrogen peroxide, p-benzoquinone and the like, and improves the reaction efficiency. The high boiling point of the compound shown in the formula II enables the compound to be always positioned in a tower kettle in the rectification process, and finally the compound and tar are sent to incineration together, so that interference on product separation is avoided.
In the present invention, the preparation method of the compound shown in the formula II may be selected from the following modes:
(1) Reacting 1-naphthol or a derivative thereof shown in the following formula I with concentrated sulfuric acid to obtain 1-naphthol sulfonic acid or a derivative thereof;
(2) Reacting phosphorus trichloride, 1-naphthol sulfonic acid or derivatives thereof with triethylamine under a low-temperature condition to obtain a compound shown in the formula II;
I is a kind of
II (II)
In formula I and formula II, R is selected from H or CH 3、C2H5.
Specifically, the synthetic route for the compounds of formula II above is shown below:
In the specific embodiment of the preparation method, in the step (1), the weight ratio of the 1-naphthol or the derivative thereof to the concentrated sulfuric acid is 1 (2-3), for example, 1:2.2,1:2.5 and 1:2.8, and the reaction time is 3-5 hours, for example, 3.5 hours, 4 hours and 4.5 hours.
In some embodiments, the 1-naphthol or derivative thereof is reacted with concentrated sulfuric acid after being dissolved in a solvent, which may be selected from the group consisting of N, N-dimethylformamide, DMSO, acetonitrile, or water.
In some specific embodiments, in the step (2), 1-naphthol sulfonic acid or a derivative thereof and phosphorus trichloride are dissolved in a solvent to form a mixed solution, triethylamine is dripped into the mixed solution to react at a low temperature, specifically toluene, tetrahydrofuran, anisole or methylene dichloride is selected as the solvent, in some preferred embodiments, the reaction is carried out at-20-0 ℃ for 20-30 hours, in some more preferred embodiments, water quenching is added into the reaction solution after the reaction is finished, and then the upper oil phase is washed and separated by deionized water to obtain the compound shown in the formula II.
In a specific embodiment of the method for preparing a compound represented by formula II, in the step (2), the mass ratio of the 1-naphthol sulfonic acid or derivative thereof to phosphorus trichloride is controlled to be (1-3): 1, for example, 1.5:1,2.0:1,2.5:1.
In some embodiments, the mass ratio of 1-naphtholsulfonic acid or derivative thereof to triethylamine is controlled to be (1.0-1.5): 1, e.g., 1.2:1,1.3:1.
In some specific embodiments, the temperature of the low-temperature reaction in the step (2) is controlled to be-20-0 ℃, such as-15 ℃ -10 ℃ -5 ℃, and the reaction time is 20-30 hours, such as 25 hours and 28 hours.
In some embodiments, the phenol hydroxylation reaction solution is reacted with the compound of formula II in an aging reactor, wherein the aging reactor is selected from one of a reaction kettle, a fixed bed, a tower reactor, a fluidized bed, or a storage tank. Specifically, the aging reactor is arranged behind the hydroxylation reactor, and a certain residence time is arranged, so that the buffer effect is achieved on a subsequent rectification system, and excessive peroxide is prevented from directly entering the rectification system.
In some embodiments, the concentration of hydrogen peroxide at the outlet of the aging reactor is less than 10 ppm and the concentration of benzoquinone is less than 5 ppm after treatment by the treatment process of the present invention.
By adopting the technical scheme, the method has the following technical effects:
The treatment method of the invention utilizes the characteristics of reducibility, water solubility and high boiling point of the compound shown in the formula II, avoids the decomposition and oxygen production in the treatment process, has no explosion risk and meets the requirement of intrinsic safety. Meanwhile, the compound shown in the formula II has sulfonic acid groups, has certain water solubility, can be dissolved in phenol hydroxylation reaction liquid, and can perform homogeneous reaction with hydrogen peroxide, p-benzoquinone and the like, so that the reaction efficiency is improved.
The treatment method of the invention uses an aging reactor arranged behind the hydroxylation reactor and a certain residence time to buffer the subsequent rectification system, thereby avoiding residual excessive peroxide from directly entering the rectification system.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of a compound shown in a formula II prepared in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance spectrum of the compound shown in the formula II prepared in the embodiment 2 of the present invention;
FIG. 3 is a nuclear magnetic resonance spectrum of the compound of formula II prepared in example 3 of the present invention.
Detailed Description
The following describes specific embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
Unless otherwise indicated, the starting materials and reagents used in the following examples were either commercially available or may be prepared by known methods.
Example 1
(1) Injecting 30g of 1-naphthol and 150g of DMF into a three-necked flask, slowly dripping 60g of concentrated sulfuric acid (with the mass concentration of 98%) into a reaction system at normal temperature, reacting for 3 hours, and separating and purifying to obtain a compound 1-naphthol sulfonic acid;
(2) Under anhydrous condition, 30g of the prepared 1-naphthol sulfonic acid and 20g of phosphorus trichloride are dissolved in 150g of toluene, the mixture is injected into a three-necked flask, the three-necked flask is cooled to-15 ℃, 30g of triethylamine is dropwise added into the three-necked flask, the reaction is continued for 30h after the dropwise addition, and 20g of water is added for quenching reaction. Taking an upper oil phase, washing with deionized water, and separating to obtain a compound shown in the following formula II:
II (II)
The compound shown in the formula II prepared by the method is subjected to nuclear magnetic analysis, the analysis result of a hydrogen spectrum is shown as 2.0 (2H), 7.58 (2H), 7.61 (2H), 7.69 (2H), 8.00 (2H) and 8.09 (2H), and the specific spectrum is shown as figure 1.
20G of the compound shown in the formula II and 2000g of phenol hydroxylation reaction liquid are taken to react in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 18% of water, 27% of phenol, 35% of methanol, 17.2% of benzenediol, 2.7% of tar, 0.09% of hydrogen peroxide and 0.01% of quinone substances, the reaction liquid is reacted for 0.5h at 80 ℃, the concentration of the hydrogen peroxide at a discharge port of the reaction kettle is reduced to below 10ppm, and the concentration of p-benzoquinone is reduced to below 5 ppm.
Example 2
(1) Injecting 30g of 7-methyl-1-naphthol and 160g of DMSO into a three-necked flask, slowly dripping 66g of concentrated sulfuric acid (with the mass concentration of 98%) into a reaction system at normal temperature, reacting for 3.5h, and separating and purifying to obtain a compound 7-methyl-1-naphthol sulfonic acid;
(2) Under the anhydrous condition, 30g of the prepared 7-methyl-1-naphthol sulfonic acid and 15g of phosphorus trichloride are dissolved in 140g of toluene, the mixture is injected into a three-necked flask, the three-necked flask is cooled to-10 ℃,22 g of triethylamine is dropwise added into the three-necked flask, the reaction is continued for 25 hours after the dropwise addition, and then 20g of water is added for quenching reaction. Taking an upper oil phase, washing with deionized water, and separating to obtain a compound shown in the following formula II:
II (II)
The nuclear magnetic analysis is carried out on the compound shown in the formula II, which is prepared by the method, the analysis result of the hydrogen spectrum is as follows, 2.0 (2H), 2.45 (6H), 7.11 (2H), 7.65 (2H), 8.01 (2H), 8.03 (2H) and 8.40 (2H), and the specific spectrum is shown in figure 2.
20G of the compound shown in the formula II and 3000g of phenol hydroxylation reaction liquid are taken to react in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 16% of water, 30% of phenol, 32% of methanol, 18.9% of benzenediol, 2.969% of tar, 0.12% of hydrogen peroxide and 0.011% of quinone substances, the reaction liquid is reacted for 0.5h at 80 ℃, the concentration of the hydrogen peroxide at a discharge hole of the reaction kettle is reduced to below 5ppm, and the concentration of the p-benzoquinone is reduced to below 3 ppm.
Example 3
(1) Injecting 30g of 7-ethyl-1-naphthol and 165g of acetonitrile into a three-necked flask, slowly dropwise adding 75g of concentrated sulfuric acid (with the mass concentration of 98%) into a reaction system at normal temperature, reacting for 4 hours, and separating and purifying to obtain a compound 7-ethyl-1-naphthol sulfonic acid;
(2) Under anhydrous condition, 30g of the prepared 7-ethyl-1-naphthol sulfonic acid and 12g of phosphorus trichloride are dissolved in 140g of tetrahydrofuran, the solution is injected into a three-necked flask, the three-necked flask is cooled to-5 ℃, 24g of triethylamine is dripped into the three-necked flask, the reaction is continued for 28h after the dripping is completed, and 20g of water is added for quenching reaction. Taking an upper oil phase, washing with deionized water, and separating to obtain a compound shown in the following formula II:
II (II)
The nuclear magnetic analysis is carried out on the compound shown in the formula II, the hydrogen spectrum analysis results are 1.31 (6H), 2.71 (4H), 7.11 (2H), 7.65 (2H), 8.01 (2H), 8.03 (2H) and 8.40 (2H), and the specific spectrograms are shown in figure 3.
20G of the compound shown in the formula II and 2000g of phenol hydroxylation reaction liquid are taken to react in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 19% of water, 33% of phenol, 31% of methanol, 15.5% of benzenediol, 1.4% of tar, 0.09% of hydrogen peroxide and 0.01% of quinone substances, the reaction liquid is reacted for 0.5h at 80 ℃, the concentration of the hydrogen peroxide at a discharge hole of the reaction kettle is reduced to below 6ppm, and the concentration of the p-benzoquinone is reduced to below 4 ppm.
Example 4
(1) Injecting 30g of 1-naphthol and 170g of water into a three-necked flask, slowly dripping 80g of concentrated sulfuric acid (with the mass concentration of 98%) into a reaction system at normal temperature, reacting for 3.8h, and separating and purifying to obtain a compound 1-naphthol sulfonic acid;
(2) Under anhydrous condition, 30g of the prepared 1-naphthol sulfonic acid and 26g of phosphorus trichloride are dissolved in 130g of anisole, the mixture is injected into a three-necked flask, the three-necked flask is cooled to 0 ℃,20 g of triethylamine is dripped into the three-necked flask, the reaction is continued for 22h after the dripping is finished, and 20g of water is added for quenching reaction. Taking an upper oil phase, washing with deionized water, and separating to obtain a compound shown in the following formula II:
II (II)
The compound shown in the formula II prepared by the method is subjected to nuclear magnetic resonance analysis, and the hydrogen spectrum analysis results are as follows, namely 2.0 (2H), 7.58 (2H), 7.61 (2H), 7.69 (2H), 8.00 (2H) and 8.09 (2H), and the nuclear magnetic resonance spectrum of the compound is the same as that of the example 1 and is not provided repeatedly.
20G of the compound shown in the formula II and 3900g of phenol hydroxylation reaction liquid are taken to react in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 15% of water, 33% of phenol, 30% of methanol, 18% of benzenediol, 3.851% of tar, 0.14% of hydrogen peroxide and 0.009% of quinone substances, the reaction liquid is reacted for 0.5h at 80 ℃, the concentration of the hydrogen peroxide at a discharge hole of the reaction kettle is reduced to below 8ppm, and the concentration of the p-benzoquinone is reduced to below 3 ppm.
Comparative example 1
2000G of phenol hydroxylation reaction liquid is subjected to aging reaction in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 15% of water, 33% of phenol, 30% of methanol, 18% of benzenediol, 3.851% of tar, 0.14% of hydrogen peroxide and 0.009% of quinone substances, the reaction liquid is reacted for 3 hours at 80 ℃, the hydrogen peroxide at the discharge port of the reaction kettle is reduced to 500 ppm, the concentration of p-benzoquinone is about 80 and ppm, and nitrogen is continuously introduced after rectification, so that the decomposition of hydrogen peroxide to produce oxygen is avoided, and an explosive mixture is formed.
Comparative example 2
The compound of formula II below was prepared as in example 4;
II (II)
The compound shown in the formula II prepared by the method is subjected to nuclear magnetic resonance analysis, and the hydrogen spectrum analysis results are as follows, namely 2.0 (2H), 7.58 (2H), 7.61 (2H), 7.69 (2H), 8.00 (2H) and 8.09 (2H), and the nuclear magnetic resonance spectrum of the compound is the same as that of the example 1 and is not provided repeatedly.
Taking 20g of the prepared compound shown in the formula II and 200000g of phenol hydroxylation reaction liquid to perform aging reaction in a reaction kettle, wherein the phenol hydroxylation reaction liquid comprises 19% of water, 33% of phenol, 31% of methanol, 15.5% of benzenediol, 1.4% of tar, 0.09% of hydrogen peroxide and 0.01% of quinone substances, the reaction liquid is reacted for 3 hours at 80 ℃, the hydrogen peroxide at a discharge port of the reaction kettle is reduced to 200 ppm, the concentration of p-benzoquinone is about 50 ppm, and nitrogen is continuously introduced after the reaction kettle enters rectification to avoid the decomposition of the hydrogen peroxide to produce oxygen, so as to form an explosive mixture.
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| JP3155685B2 (en) * | 1995-07-20 | 2001-04-16 | 財団法人山形県企業振興公社 | Method for measuring peroxidase |
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