CN113173874B - Method for extracting hydroperoxide from m-diisopropylbenzene oxidation product - Google Patents
Method for extracting hydroperoxide from m-diisopropylbenzene oxidation product Download PDFInfo
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Abstract
The invention provides a method for extracting hydroperoxide from m-diisopropylbenzene oxidation products. According to the method, alkaline liquor extraction, neutralization and back extraction are sequentially carried out on the hydroperoxide intermediate DHP and byproducts generated after primary oxidation of m-diisopropylbenzene, the influence of pH value on the effect of back extraction DHP is explored, the capability of accurately regulating and controlling intermediate product treatment is realized, and therefore subsequent secondary oxidation is facilitated and the yield of resorcinol is remarkably improved.
Description
Technical Field
The invention relates to a process for preparing m-diphenol by m-diisopropylbenzene oxidation, in particular to a method for extracting hydroperoxide from m-diisopropylbenzene oxidation products.
Background
Resorcinol (Resorcinol) is an important chemical intermediate and is widely applied to the fields of agriculture, dyes, medicines, rubber and the like. At present, the industrial production process of resorcinol mainly comprises the following steps: a sulfonation alkali fusion method using benzene as a raw material, an oxidation method using m-diisopropylbenzene as a raw material and a m-phenylenediamine hydrolysis method. The process for preparing resorcinol by m-diisopropylbenzene oxidation is firstly proposed in 1967, resorcinol and byproduct acetone are prepared by oxidation, decomposition, separation and purification and other stages, and the process is widely concerned by scholars at home and abroad due to the characteristics of small pollution, low cost, short flow, high yield and the like. The reaction principle of the m-diisopropylbenzene oxidation method is shown in figure 2, m-Diisopropylbenzene (DIPB) is firstly oxidized to generate a 1, 3-dihydroperoxide Diisopropylbenzene (DHP) intermediate, and the intermediate is decomposed under the acid catalysis condition to generate resorcinol and acetone. In general, to ensure complete oxidation, DHP is formed from DIPB by primary oxidation (FIG. 3) and secondary oxidation (FIG. 5), and crude resorcinol is obtained by decomposition and neutralization.
The diisopropylbenzene oxidation method has many defects while having advantages, and has high technical content, complex operation and higher requirements on equipment. In the primary oxidation process of m-diisopropylbenzene, hydroperoxide byproducts (as shown in fig. 3-4) which can not be directly decomposed into resorcinol by subsequent catalysis are generated, and the generation of the byproducts causes lower yield and purity of resorcinol, so that raw materials for reaction cause a large amount of waste, and the industrial popularization of the method is hindered.
For the purpose of increasing the yield of resorcinol, there has been known an improvement method such as Nakagawa et al (Nakagawa, hiroaki et al. Process for the preparation of resorcinol: US 4283570 2 [ P ], [ 2 ]]1981) before the decomposition reaction, the primary oxidation product is reacted with H 2 O 2 The secondary oxidation is carried out under the condition of an acid catalyst (such as sulfuric acid), a solvent is toluene, and a byproduct water is distilled out in the form of toluene azeotrope, so that the balance is shifted to the right due to the continuous reduction of water in the system, and the yield is improved. Then in a system using acetone as a solvent, si-Al is used as a catalyst to carry out decomposition reaction, and the yield can reach 85%.
Wu et al, for the first time, realized a low temperature, normal pressure oxidation process under anhydrous, alkali-free conditions (Wu Ching-Yong et al, process for the preparation of stress: US 4849549P].1987；Wu Ching-Yong et al.Decomposition of dihydroperoxide to resorcinol:US 4847436[P].1989). After the first oxidation, the hydroperoxide was extracted with hot methyl isobutyl ketone. Distilling off the extractant, dissolving it in an organic solvent such as toluene, and then adjusting the content of H by an amount of 13 to 18% 2 O 2 And 96% of H 2 SO 4 The solution is secondarily oxidized at 40 ℃ for 1 hour and then BF is used 3 The resorcinol is obtained by decomposition with a catalyst, and the yield is 89%.
The method commonly used in industry at present is to extract the primary oxidation liquid with alkali liquor before the secondary oxidation reaction, so that the hydroperoxide generated in the primary oxidation stage exists in an aqueous phase in the form of ions, then add sulfuric acid to the aqueous phase extracted from the alkali liquor, so that hydroxide ions in the aqueous phase are converted into hydroperoxide oily matter, and then use methyl isobutyl ketone (MIBK) to perform back extraction on the hydroperoxide in the aqueous phase, so as to obtain an intermediate rich in DHP. However, the methods still have limited improvement of resorcinol yield, and the technological parameters of the intermediate treatment process cannot be accurately regulated.
Therefore, it is an urgent need to provide a method for improving the yield of resorcinol by improving the ability of extracting DHP, which is a target intermediate oxidation product, from resorcinol oxidation product, with simple operation and low cost.
Disclosure of Invention
The invention provides a method for extracting hydroperoxide from m-diisopropylbenzene oxidation products. According to the method, alkaline liquor extraction, neutralization and back extraction are sequentially carried out on the hydroperoxide intermediate DHP and byproducts generated after primary oxidation of m-diisopropylbenzene, the influence of pH value on the effect of back extraction DHP is explored, the capability of accurately regulating and controlling intermediate product treatment is realized, and therefore subsequent secondary oxidation is facilitated and the yield of resorcinol is remarkably improved.
The technical scheme of the invention is as follows:
a process for extracting hydroperoxides from a m-diisopropylbenzene oxidation product, said process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen into m-Diisopropylbenzene (DIPB) for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: adding DIPB into the primary oxidation liquid, extracting the hydroperoxide intermediate DHP generated in the primary oxidation stage by using alkali liquor, wherein the DHP exists in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introducing CO 2 The gas is used for adjusting the pH value of the water phase extracted from the alkali liquor, so that hydroperoxide ions in the water phase are converted into hydroperoxide organic matters, and meanwhile oily sediment rich in hydroperoxide is formed in the water phase;
(4) A back extraction stage: DHP was back-extracted using methyl isobutyl ketone (MIBK).
Further, in the primary oxidation stage, the oxidation reaction temperature of DIPB is controlled to be 70-95 ℃.
Further, in the primary oxidation stage, the space velocity of the oxygen is 500ml/min-900ml/min.
Further, in the primary oxidation stage, in addition to the oxidation of DIPB to produce the hydroperoxide intermediate DHP, side reactions occur, such as diisopropylbenzene Monohydroperoxide (MHP), diisopropylbenzene 1-hydroperoxide-3-benzyl alcohol (HHP), diisopropylbenzene monobenzyl alcohol (MCL), diisopropylbenzene Monoethyl Ketone (MKT), diisopropylbenzene 1, 3-dibenzyl alcohol (DCL), diisopropylbenzene 1-peroxide-3-ethyl Ketone (KHP), diisopropylbenzene 1-benzyl alcohol-3-ethyl Ketone (KCL), and the like.
Further, in the alkali liquor extraction stage, the amount of the DIPB accounts for 3% -10% of the mass of the primary oxidation liquid.
Further, in the alkali liquor extraction stage, the alkali liquor is NaOH solution with the mass concentration of 4% -5%, and the adding amount of the alkali liquor is 0.6-1 of the mass of all oil phases containing DIPB in the primary oxidation solution.
Further, in the alkali liquor extraction stage, the extraction time is 30min-60min, and the extraction temperature is 30 ℃ to 60 ℃.
Further, in the neutralization stage, CO is introduced 2 The gas adjusts the aqueous phase extracted from the lye so that the pH of the aqueous phase is 7-14, preferably 7-8.
Further, in the stripping stage, the dosage of the MIBK is 0.6-1 of the mass ratio of the feed to be stripped.
Furthermore, in the back extraction stage, the temperature is controlled to be 40-60 ℃, and the extraction time is 30-60 min.
The invention has the following technical effects:
1. in the method, the DIPB is added into the primary oxidation liquid before the alkali liquor extraction, so that the dissolution of organic matters is promoted, the difficulty of the alkali liquor extraction is reduced, and a demulsifier is not required to be added.
2. Introducing CO 2 The gas is used for adjusting the pH value of the water phase, and other pH values are avoidedThe components are introduced, so that the use amount of MIBK in the subsequent back extraction stage is saved; CO in comparison with other acidic substances 2 The price is low, the storage is convenient, the potential safety hazard is small, and the cost of industrial production is reduced.
3. The method of the invention sequentially performs alkali liquor extraction, neutralization and back extraction on the hydroperoxide intermediate DHP and byproducts generated after the primary oxidation of m-diisopropylbenzene, simultaneously explores the influence of pH value on the effect of back extraction DHP, and realizes the capability of accurately regulating and controlling the treatment of the intermediate product. Experiments have shown that the purity of the hydroperoxide correlates with the pH value after neutralization. For MIBK back extraction experiments, the low pH value is favorable for back extraction, the higher the pH value is, the lower the content of the target product DHP in the oil phase of the back extraction is, and the higher the content of the by-product is. When the pH value is lower than 8, the back extraction result is better, wherein the content of DHP is higher than 91.7%, and the content of MCL is lower than 0.01%. Therefore, the pH value should be controlled to be lower than 8 in the back extraction experiment.
Drawings
FIG. 1 is a process flow diagram of the present invention for extracting hydroperoxide from m-diisopropylbenzene oxidation products;
FIG. 2 is a reaction schematic diagram of m-diisopropylbenzene oxidation process for preparing resorcinol;
FIG. 3 is a reaction equation of the primary oxidation of m-diisopropylbenzene;
FIG. 4 is a diagram of the by-products of the primary oxidation reaction of m-diisopropylbenzene;
FIG. 5 is a schematic diagram of a secondary oxidation reaction of m-diisopropylbenzene;
Detailed Description
The invention is further illustrated by the following examples:
example 1
A process for extracting hydroperoxide from m-diisopropylbenzene oxidation product, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen with the space velocity of 500ml/min into m-Diisopropylbenzene (DIPB) at the temperature of 70 ℃ for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: taking 100 parts by weight of primary oxidation liquid, adding 5 parts by weight of DIPB into the primary oxidation liquid, uniformly stirring, adding 84 parts by weight of alkali liquor, wherein the alkali liquor is NaOH solution with the mass concentration of 4%, stirring for 30min at 40 ℃, layering, allowing a hydroperoxide intermediate DHP generated in an oxidation stage to exist in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introducing CO 2 Adjusting the pH value of the aqueous phase extracted from the alkali liquor to 13.5 by using gas, so that hydroperoxide ions in the aqueous phase are converted into hydroperoxide organic matters, and meanwhile, oily sediment rich in hydroperoxide is formed in the aqueous phase;
(4) A back extraction stage: introducing the water phase with pH =13.5 into a stripping tower, adding methyl isobutyl ketone (MIBK) with equal mass, stirring at 60 deg.C for 30min for stripping,
the extract had a DHP content of 78.37%, a KHP content of 1.38%, a HHP content of 12.36%, a MHP content of 5.96%, and an MCL content of 2.96%.
Example 2
A process for extracting hydroperoxide from m-diisopropylbenzene oxidation products, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen with the space velocity of 650ml/min into m-Diisopropylbenzene (DIPB) at the temperature of 80 ℃ for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: taking 100 parts by weight of primary oxidation liquid, adding 5 parts by weight of DIPB into the primary oxidation liquid, uniformly stirring, adding 84 parts by weight of alkali liquor, wherein the alkali liquor is NaOH solution with the mass concentration of 5%, stirring for 30min at 45 ℃, layering, allowing a hydroperoxide intermediate DHP generated in an oxidation stage to exist in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introduction of CO 2 The gas is used for adjusting the pH value of the aqueous phase extracted from the alkali liquor to 12, so that the hydroperoxide ions in the aqueous phase are converted into hydroperoxide organic matters, and meanwhile, hydrogen peroxide-rich hydrogen peroxide is formed in the aqueous phaseOily precipitation of the material;
(4) A back extraction stage: introducing the water phase with pH =12 into a stripping tower, adding methyl isobutyl ketone (MIBK) with equal mass, stirring at 60 deg.C for 30min for stripping,
the extract had a DHP content of 78.37%, a KHP content of 1.2%, a HHP content of 5.54%, a MHP content of 5.54%, and an MCL content of 5.22%.
Example 3
A process for extracting hydroperoxide from m-diisopropylbenzene oxidation products, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen with the space velocity of 700ml/min into m-Diisopropylbenzene (DIPB) at the temperature of 85 ℃ for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: taking 100 parts by weight of primary oxidation liquid, adding 5 parts by weight of DIPB into the primary oxidation liquid, uniformly stirring, adding 84 parts by weight of alkali liquor, wherein the alkali liquor is NaOH solution with the mass concentration of 5%, stirring for 30min at 50 ℃, layering, allowing a hydroperoxide intermediate DHP generated in an oxidation stage to exist in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introducing CO 2 Adjusting the pH value of the aqueous phase extracted from the alkali liquor to 9.8 by using the gas, so that hydroperoxide ions in the aqueous phase are converted into hydroperoxide organic matters, and meanwhile, oily sediment rich in hydroperoxide is formed in the aqueous phase;
(4) A back extraction stage: introducing the water phase with pH =9.8 into a stripping tower, adding methyl isobutyl ketone (MIBK) with equal mass, stirring at 60 deg.C for 30min for stripping,
the extract had a DHP content of 81.36%, a KHP content of 0.99%, a HHP content of 8.91%, a MHP content of 5.38%, and an MCL content of 3.25%.
Example 4
A process for extracting hydroperoxide from m-diisopropylbenzene oxidation products, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen with the space velocity of 700ml/min into m-Diisopropylbenzene (DIPB) at the temperature of 75 ℃ for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: taking 100 parts by weight of primary oxidation liquid, adding 5 parts by weight of DIPB into the primary oxidation liquid, uniformly stirring, adding 84 parts by weight of alkali liquor, wherein the alkali liquor is NaOH solution with the mass concentration of 5%, stirring at 50 ℃ for 30min, layering, allowing a hydroperoxide intermediate DHP generated in an oxidation stage to exist in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introducing CO 2 Adjusting the pH value of the water phase extracted from the alkali liquor to 7.8 by using the gas, so that hydroperoxide ions in the water phase are converted into hydroperoxide organic matters, and meanwhile, oily sediment rich in hydroperoxide is formed in the water phase;
(4) A back extraction stage: introducing the water phase with pH =7.8 into a back extraction tower, adding equal mass of methyl isobutyl ketone (MIBK), stirring at 60 ℃ for 30min for back extraction,
the extract contains DHP 92.45%, KHP 0.16%, HHP 4.27%, MHP 3.13%, and MCL 0.01%.
Example 5
A process for extracting hydroperoxide from m-diisopropylbenzene oxidation product, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen with the space velocity of 800ml/min into m-Diisopropylbenzene (DIPB) at the temperature of 75 ℃ for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: taking 100 parts by weight of primary oxidation liquid, adding 5 parts by weight of DIPB into the primary oxidation liquid, uniformly stirring, adding 84 parts by weight of alkali liquor, wherein the alkali liquor is NaOH solution with the mass concentration of 5%, stirring for 30min at 40 ℃, layering, enabling a hydroperoxide intermediate DHP generated in an oxidation stage to exist in a water phase in an ion form, and refluxing an extracted oil phase to a primary oxidation kettle for continuous reaction;
(3) And (3) a neutralization stage: introduction of CO 2 Adjusting the pH value of the water phase extracted from the alkali liquor to 7.5 by using the gas, so that hydroperoxide ions in the water phase are converted into hydroperoxide organic matters, and meanwhile, oily sediment rich in hydroperoxide is formed in the water phase;
(4) A back extraction stage: introducing the water phase with pH =7.5 into a back extraction tower, adding equal mass of methyl isobutyl ketone (MIBK), stirring at 60 deg.C for 30min for back extraction,
the extract liquid contains DHP 91.37%, KHP 0.33%, HHP 5%, MHP 2.94%, and MCL 0.01%.
The method of the invention sequentially performs alkali liquor extraction, neutralization and back extraction on the hydroperoxide intermediate DHP and byproducts generated after the primary oxidation of m-diisopropylbenzene, simultaneously explores the influence of pH value on the effect of back extraction DHP, and realizes the capability of accurately regulating and controlling the treatment of the intermediate product. Experiments have shown that the purity of the hydroperoxide is related to the pH value after neutralization. For MIBK back extraction experiments, the low pH value is favorable for back extraction, the higher the pH value is, the lower the content of the target product DHP in the oil phase of the back extraction is, and the higher the content of the by-product is. When the pH value is lower than 8, the back extraction result is better, wherein the content of DHP is higher than 91.7%, and the content of MCL is lower than 0.01%. Therefore, the pH value of the stripping experiment should be controlled to be lower than 8.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, but any modifications or equivalent variations made according to the technical spirit of the present invention are within the scope of the present invention as claimed.
Claims (3)
1. A process for extracting hydroperoxide from m-diisopropylbenzene oxidation product, the process comprising the steps of:
(1) A primary oxidation stage: continuously introducing oxygen into m-Diisopropylbenzene (DIPB) for continuous oxidation to obtain primary oxidation liquid containing hydroperoxide intermediate 1, 3-dihydroperoxide Diisopropylbenzene (DHP);
(2) Alkali liquor extraction stage: adding DIPB into the primary oxidation liquid, extracting the hydroperoxide intermediate DHP generated in the primary oxidation stage by using alkali liquor, wherein the DHP exists in a water phase in the form of ions, and refluxing the extracted oil phase to the primary oxidation kettle for continuous reaction;
the amount of the DIPB accounts for 3% -10% of the mass of the primary oxidation liquid; the alkali liquor is NaOH solution with the mass concentration of 4-5%, and the adding amount of the alkali liquor is 0.6-1 of the mass of all oil phases containing DIPB in the primary oxidation solution; and
the extraction time is 30-60 min, and the extraction temperature is 30-60 ℃;
(3) And (3) a neutralization stage: introduction of CO 2 The gas is used for adjusting the pH value of the water phase extracted from the alkali liquor, so that hydroperoxide ions in the water phase are converted into hydroperoxide organic matters, and meanwhile oily sediment rich in hydroperoxide is formed in the water phase; wherein, CO is introduced 2 Adjusting the pH of the aqueous phase extracted from the alkali liquor to 7-8 by using gas;
(4) A back extraction stage: using methyl isobutyl ketone (MIBK) to back-extract DHP;
the using amount of the MIBK is 0.6-1 of the mass ratio of the feed to be subjected to the back extraction treatment; and
in the back extraction stage, the temperature is controlled to be 40-60 ℃, and the extraction time is 30-60 min.
2. The process of claim 1 wherein said DIPB oxidation reaction temperature is controlled to be in the range of 70 ℃ to 95 ℃ during said primary oxidation stage.
3. The process of claim 2 wherein the space velocity of the oxygen in the primary oxidation stage is in the range of from 500ml/min to 900ml/min.
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