CN114105845A - Selective decomposition method of cymene oxidation product and application thereof - Google Patents
Selective decomposition method of cymene oxidation product and application thereof Download PDFInfo
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
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Abstract
The invention discloses a selective decomposition method of an cymene oxidation product, which comprises the following steps: under the catalysis of strong basic ion exchange resin, carrying out selective decomposition reaction on PCHP in the oxidation product of the cymene to obtain a reserved TCHP product; the oxidation product of the cymene contains PCHP and TCHP. The invention adopts strong-base ion exchange resin as the catalyst, thereby not only avoiding the generation of a large amount of alkali-containing wastewater and being more environment-friendly, but also avoiding the entrainment of alkaline substances in the product and facilitating the subsequent reaction. The invention also discloses a cresol production process, and the decomposition method is adopted as a step, so that the generation of alkali-containing wastewater is reduced, and the method is more suitable for industrial production.
Description
Technical Field
The invention belongs to the field of chemical intermediate production, relates to a production method of cresol and an intermediate thereof, and particularly relates to a selective decomposition method of an cymene oxidation product and application thereof.
Background
The oxidation product of the cymene contains TCHP (p-cymene tertiary hydroperoxide) and PCHP (p-cymene primary hydroperoxide), and the TCHP is further subjected to acidolysis and hydrogenation to obtain cresol which is an important chemical intermediate. Cresol is an important raw material for synthesizing fine chemical products such as BHT (2, 6-di-tert-butyl-p-cresol), anisic aldehyde, p-hydroxybenzaldehyde and the like. If PCHP is subjected to acidolysis reaction with TCHP, it will be decomposed into isopropyl phenol and formaldehyde, and formaldehyde will undergo phenolic condensation reaction with cresol, which is the reaction product of TCHP, thereby affecting the yield of cresol. Wherein the TCHP and PCHP have the following structural formulas:
in the currently reported patents (for example, US5166451, US5600026, and US 56329922), PCHP is selectively decomposed (or referred to as alkaline hydrolysis) by using alkaline substances (sodium hydroxide solution and quaternary ammonium base) to generate p-isopropyl benzyl alcohol and p-isopropyl benzaldehyde, so as to prevent the acid hydrolysis yield of TCHP from being affected. The reaction mechanism is as follows: PCHP contains alpha hydrogen, is unstable to alkali, is prone to Kornblum-Delamare decomposition reaction, and TCHP is slightly decomposed into p-methyl phenyl isopropanol under the action of alkali.
The reaction equation is as follows:
the alkaline hydrolysis reaction in the prior patent is mostly a liquid-liquid system, and the good contact between the alkaline site and the PCHP is realized by stirring and adding an auxiliary agent.
The sumitomo chemical industries co, CN1009927B, discloses a method for treating a hydroperoxide mixture containing an aromatic primary hydroperoxide and an aromatic tertiary hydroperoxide in the presence of a base and an organic ammonium salt, the PCHP decomposition rate can reach 100%, the TCHP retention rate can reach 98.0%, the method analyzes the product ratio after the treatment only by a liquid phase method, and no subsequent treatment steps are given. The Sumitomo chemical industry Co., Ltd later gave in CN1079952A a relatively complete cresol production process, in which the treatment of the hydroperoxide mixture employed a selective decomposition reaction of the oxidation product of cymene with liquid base and an auxiliary agent, which was able to decompose PCHP with high selectivity while retaining TCHP, but the product was subjected to phase separation and water washing to remove the base, with numerous steps, complicated operations, and at the same time, all operations were batch-wise.
Further, from the Sumitomo chemical industry Co., Ltd, CN1058002C discloses a method for post-treating a hydroperoxide mixture, which suggests that although the selectivity of the previously reported methods (alkali and organic quaternary ammonium salts) is high, the anions of the organic quaternary ammonium salts are harmful to the equipment and also generate amine compounds which are difficult to separate, and proposes that an alkali metal hydroxide or alkaline earth metal hydroxide (solution) is used as a catalyst, a metal carboxylate is added as an aid to carry out a decomposition reaction, the PCHP decomposition rate can reach 99%, the TCHP retention can reach more than 96%, and the method still uses an excessive amount of an inorganic aqueous alkali solution and requires a phase separation treatment; in addition, in order to ensure the stability and safety of the subsequent steps, a process of removing alkali by organic phase acid washing or water washing is needed, and partial loss of products is caused.
The above patents all adopt the mode of mixing alkali-containing solution and oxidation products to carry out the selective decomposition reaction of PCHP, and the mode has the following defects: 1. the operation is complicated because the treatment after clarification, phase separation and washing is needed; 2. the alkaline solution may be carried in the oxidation product, so that a catalyst (sulfuric acid) in the acidolysis process is consumed, the acidolysis reaction cannot be effectively carried out, the concentration of the residual peroxide is high, and great potential safety hazard is brought; 3. the reaction is carried out in an intermittent mode by adding alkaline water and then staying for a certain time; 4. the alkaline solution is used as a catalyst, a large amount of strong alkaline waste water is generated after the reaction is finished, and a large amount of acid is consumed for neutralization.
With respect to the above-mentioned problem of entrainment of the alkali at point 2, CN1764637A particularly describes the phenomenon of treating the organic hydroperoxide containing reaction product with an aqueous alkaline solution and proposes a solution to washing with water, which requires special equipment and processes, is costly, and does not fundamentally solve the problem of treating the organic hydroperoxide with an alkaline solution.
Disclosure of Invention
The invention aims to solve the technical problem of providing a selective decomposition method of an oxidation product of cymene and application thereof, wherein the decomposition method has the advantages of clean and environment-friendly reaction process, no generation of alkali-containing wastewater, no entrainment of alkaline substances in the decomposition product, and higher PCHP decomposition rate and TCHP retention rate.
The technical scheme of the invention is as follows:
a process for the selective decomposition of oxygenated cymene, comprising:
under the catalysis of strong basic ion exchange resin, carrying out selective decomposition reaction on PCHP in the oxidation product of the cymene to obtain a reserved TCHP product;
the oxidation product of the cymene contains PCHP and TCHP.
The inventor adopts strong-base ion exchange resin to catalyze PCHP to decompose, and finds that although the reaction is a solid-liquid interface reaction, the alkali sites with enough strength and enough quantity can be contacted with a reaction liquid, the alkali decomposition reaction of the oxidation product of the cymene can be catalyzed well, the effect of the liquid phase reaction under the catalysis of an auxiliary agent and alkali is basically consistent, the decomposition rate of the PCHP can reach more than 90%, and the TCHP can be reserved more than 95%; in addition, as the solid alkali is adopted, alkaline substances cannot be carried in the product, so that the consumption of a catalyst (sulfuric acid) in the acidolysis process is avoided, the acidolysis reaction cannot be effectively carried out, the concentration of residual peroxide is high, and greater potential safety hazard is brought, thereby ensuring the safety of the post-treatment of acidolysis and rectification; and the reaction process is clean, no alkali-containing wastewater is generated, and the method is more environment-friendly.
Preferably, the strongly basic ion exchange resin is filled in a fixed bed reactor, and the oxidation product of the cymene is continuously fed into the fixed bed reactor for reaction, so that the reactor is simple in form, the fixed bed is continuously operated, the product does not need phase separation operation, the service life of the catalyst is long, and the catalytic effect is more stable.
Preferably, the reaction temperature is 50 to 90 ℃, more preferably 80 to 90 ℃, and the reaction pressure is 0 to 0.5MPa (gauge pressure).
Preferably, the feeding space velocity of the oxidation product of the cymene is 0.5-1.0 h-1。
The strong-base ion exchange resin has a key influence on the treatment process, and the PCHP decomposition rate and the TCHP retention rate can be high only by using a proper strong-base ion exchange resin, and preferably, the strong-base ion exchange resin is one or more of AmberLite HPR900 OH, Amberlyst A26OH, AmberLite FPA40 Cl and AmberLite FPA98 Cl.
Preferably, the strongly basic ion exchange resin is a macroporous ion exchange resin, which enables higher PCHP decomposition rate and TCHP retention than gel resin, and more preferably, the strongly basic ion exchange resin is AmberLite HPR900 OH or Amberlyst A26 OH.
Preferably, the oxidation product of cymene is a reaction solution obtained by oxidation of cymene or a product obtained by post-treating (for example, washing, filtering or concentrating) the reaction solution. The oxidation product of the cymene comprises, besides a primary p-cymene hydroperoxide PCHP and a tertiary p-cymene hydroperoxide TCHP, unreacted cymene and other impurities such as ketone, aldehyde, alcohol and the like, wherein the mass content ratio of the PCHP to the TCHP is 1: 2-1: 10, generally, the mass content of the PCHP is 2-4%, and the mass content of the TCHP is 15-18%.
The invention also provides a production process of cresol, which comprises the following steps:
(1) performing oxidation reaction on cymene and oxygen or oxygen-containing gas to obtain an cymene oxidation product;
(2) the oxidation product of the cymene is treated by the decomposition method to obtain a decomposition product;
(3) and carrying out acidolysis on the decomposition product to obtain cresol.
Wherein, the oxidation and acid hydrolysis of the steps (1) and (3) are the prior art, for example, refer to the operation in CN1079952A, and further, after the acid hydrolysis of the step (3) is completed, the hydrogenation can be continued according to the description of the prior art to improve the yield of cresol.
Preferably, the decomposition product obtained in step (2) is subjected to acid hydrolysis directly after removing unreacted cymene by distillation. The decomposition product in the step (2) of the cresol production process does not need to be washed for many times by water, the generation of alkali-containing wastewater is effectively reduced, the cresol production process is more suitable for industrial production, and no alkaline substance is carried in the decomposition product, so that the adverse effect on the acidolysis process is avoided.
Further, the acidolysis adopts sulfuric acid as a catalyst, and the mass ratio of the sulfuric acid to TCHP is 0.01-0.2%: 1.
further, the acidolysis reaction temperature is 50-80 ℃, and the reaction pressure is 0-0.1 MPa (gauge pressure).
Compared with the prior art, the invention has the beneficial effects that:
(1) according to the invention, the strong-base ion exchange resin is used as a catalyst to replace an alkaline aqueous solution for reaction, so that the generation of strong-base wastewater is effectively reduced under the condition of ensuring the decomposition rate of PCHP and the retention rate of TCHP, and the method is cleaner and more environment-friendly and is beneficial to industrial production;
(2) according to the invention, the strong-base ion exchange resin is used as a catalyst to replace an alkaline aqueous solution for reaction, so that alkali liquor residue in the product is avoided, and the subsequent acidification reaction is ensured to be carried out smoothly;
(3) the invention adopts the fixed bed reactor for reaction, can realize continuous operation and has simpler operation.
Drawings
FIG. 1 is a schematic view of an apparatus for decomposing an oxidation product of cymene according to the present invention.
Detailed Description
The oxidation method of cymene in the present invention is a known method, and for example, patent methods such as CN1079952A and CN1058002C can be referred to.
Example 1
(1) Preparing raw materials: the liquid phase oxidation of the cymene obtains a mixture 1 containing TCHP and PCHP with the total mass content of 20 percent and the mass ratio of TCHP to PCHP of 5.5: 1. The rest materials in the mixture 1 are mainly unreacted cymene and also contain a small amount of impurities such as ketone, aldehyde, alcohol and the like.
(2) Decomposition of oxidation products of cymene: a fixed bed 20mm in diameter and 1000mm in height was packed with 200g A26-OH (DuPont AMBERLYST, USA)TM) Strongly basic ion exchange resins (which are macroporous ion exchange resins). Taking the mixture 1 as a raw material, and feeding airspeed of 0.7h-1. The reaction temperature is 90 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 5 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 100 percent, and the TCHP retention rate is 97.2 percent.
(3) Acid hydrolysis: distilling the alkaline hydrolysis product under reduced pressure to recover unreacted cymene and raise the TCHP concentration to 65%. And (3) performing acidolysis treatment on the concentrated solution by using acetone as a reaction substrate, and adding acetone and sulfuric acid into the bottom of the three-necked flask, wherein the mass of the sulfuric acid is 0.05 percent of that of the TCHP, and the mass of the acetone is 30 percent of that of the TCHP. Slowly dripping 10g of the concentrated solution into a reaction bottle, wherein the reaction temperature is 56 ℃, and preserving heat for 20min after dripping. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the TCHP conversion rate is 99.8 percent, and the cresol yield is 96.1 percent.
Example 2
Preparing raw materials: the cymene is oxidized in liquid phase to obtain a mixture 2 containing TCHP and PCHP, wherein the total mass content of TCHP and PCHP is 18.2%, and the mass ratio of TCHP to PCHP is 5.4: 1.
A fixed bed 20mm in diameter and 1000mm in height was packed with 200g A26-OH (DuPont AMBERLYST, USA)TM) Strongly basic ion exchange resins (which are macroporous ion exchange resins). Taking the mixture 2 as a raw material, and feeding airspeed of 0.7h-1. The reaction temperature is 90 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 15 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 100 percent, and the TCHP retention rate is 96.8 percent.
Example 3
Preparing raw materials: the liquid phase oxidation of the cymene obtains a mixture 3 containing TCHP and PCHP with the total mass content of 23 percent and the mass ratio of 7.4: 1.
A fixed bed 20mm in diameter and 1000mm in height was packed with 200g A26-OH (DuPont AMBERLYST, USA)TM) Strongly basic ion exchange resins (which are macroporous ion exchange resins). Taking the mixture 3 as a raw material, and feeding airspeed of 0.7h-1. The reaction temperature is 90 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 30 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 99.5 percent, and the TCHP retention rate is 96.5 percent.
Example 4
Preparing raw materials: the liquid phase oxidation of the cymene obtains a mixture 1 containing TCHP and PCHP with the total mass content of 20 percent and the mass ratio of TCHP to PCHP of 5.5: 1.
A fixed bed 20mm in diameter and 1000mm in height was packed with 200g of HPR900-OH (DuPont AMBERLYST, USA)TM) A strongly basic ion exchange resin. Taking the mixture 1 as a raw material, and feeding airspeed of 0.7h-1. The reaction temperature is 85 ℃, the reaction temperature is normal pressure, and the reaction is continuously operated for 5 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 100 percent, and the TCHP retention rate is 97.3 percent.
Example 5
Preparing raw materials: the liquid phase oxidation of the cymene obtains a mixture 1 containing TCHP and PCHP with the total mass content of 20 percent and the mass ratio of TCHP to PCHP of 5.5: 1.
A fixed bed having a diameter of 20mm and a height of 1000mm was packed with 200g of a packingFPA40 (DuPont AMBERLYST, USA)TM) Strongly basic ion exchange resins (which are gel type ion exchange resins). The mixture 1 is taken as a raw material, and the feeding airspeed is 0.5h-1. The reaction temperature is 95 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 5 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 93.0 percent, and the TCHP retention rate is 99.0 percent.
Example 6
Preparing raw materials: the liquid phase oxidation of the cymene obtains a mixture 1 containing TCHP and PCHP with the total mass content of 20 percent and the mass ratio of TCHP to PCHP of 5.5: 1.
A fixed bed 20mm in diameter and 1000mm in height was packed with 200g of FPA98 (DuPont AMBERLYST, USA)TM) Strongly basic ion exchange resins (which are gel type ion exchange resins). The mixture 1 is taken as a raw material, and the feeding airspeed is 0.5h-1. The reaction temperature is 95 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 5 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 90.3 percent, and the TCHP retention rate is 99.2 percent.
The results of examples 5 and 6 show that the decomposition efficiency of the gel type ion exchange resin for PCHP is slightly low.
Example 7
The same as example 1 except that the reaction temperature in the decomposition step of the oxidation product of cymene was changed to 70 ℃. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 68 percent, and the TCHP retention rate is 99.0 percent.
The reaction temperature of this example was lowered, which may result in a decrease in the reaction rate and a decrease in the PCHP elution rate, but the TCHP retention rate was high, and alkaline waste water was not generated, and the problem of alkali lye remaining did not occur.
Example 8
Except that the feeding space velocity of the decomposition step of the oxidation product of the cymene is changed to 1.5h-1Otherwise, the same as in example 1. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 89%, and the TCHP retention rate is 98.7%.
In the embodiment, the feeding space velocity is increased by 1.5h-1The PCHP conversion decreased slightly corresponding to the decreased residence time, but the TCHP retention was higher since no production was possibleAlkaline wastewater is generated, the problem of alkali liquor residue is avoided, and the comprehensive effect is superior to that of the prior art.
Comparative example 1
The fixed bed with a diameter of 20mm and a height of 1000mm was packed with 200g A21 (DuPont AMBERLYST, USA)TM) Weakly basic ion exchange resins. Starting from mixture 1 of example 1, the feed rate was 2.8 mL/min. The reaction temperature is 90 ℃, the reaction is carried out at normal pressure, and the reaction is continuously carried out for 5 hours. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP elution rate is 67.0 percent, and the TCHP retention rate is 93.7 percent.
Comparing the results of example 1 and comparative example 1, it is understood that the kind of ion exchange resin greatly affects the treatment results, and the elution rate is greatly reduced by using a weakly basic ion exchange resin.
Comparative example 2
Using 100g of the oxidation product mixture 1 of cymene of example 1 as a starting material, 10g of 12% NaOH aqueous solution and 0.5g of tetramethylammonium bromide were added, and the reaction was carried out at 80 ℃ under normal pressure for 0.5 hour. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP decomposition rate is 99.0%, and the TCHP retention rate is 98.1%.
Distilling the alkaline hydrolysis product under reduced pressure to recover unreacted cymene and raise the TCHP concentration to 65%. And (3) performing acidolysis treatment on the concentrated solution by using acetone as a reaction substrate, and adding acetone and sulfuric acid into the bottom of the three-necked bottle, wherein the mass of the sulfuric acid is 0.05 percent of the mass of the TCHP. And (3) dropwise adding 10g of the concentrated solution into a reaction bottle, wherein the reaction temperature is 56 ℃, and keeping the temperature for 20min after dropwise adding. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the TCHP conversion rate is 8.3 percent, and the yield of the p-cresol is 7.8 percent.
Comparing the results of example 1 and comparative example 2, it is understood that the yield of the subsequent acidolysis reaction is greatly reduced by the alkali + ammonium salt decomposition method, and the residual alkali has a very adverse effect on the subsequent reaction and must be strictly treated.
Comparative example 3
Using 100g of the oxidation product mixture 1 of cymene of example 1 as a starting material, 10g of 12% NaOH aqueous solution and 0.5g of tetramethylammonium bromide were added, and the reaction was carried out at 80 ℃ under normal pressure for 0.5 hour. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP is decomposed by 99.0 percent, and the TCHP is reserved by 98.1 percent.
And (3) washing the alkaline hydrolysis product with 10g of deionized water each time, wherein the pH values of the water phases after 3 times of washing are 10.0, 7.9 and 7.1 respectively.
Distilling the alkaline hydrolysis product under reduced pressure to recover unreacted cymene and raise the TCHP concentration to 65%. And (3) performing acidolysis treatment on the concentrated solution by using acetone as a reaction substrate, and adding acetone and sulfuric acid into the bottom of the three-necked bottle, wherein the mass of the sulfuric acid is 0.05 percent of the mass of the TCHP. And (3) dropwise adding 10g of the concentrated solution into a reaction bottle, wherein the reaction temperature is 56 ℃, and keeping the temperature for 20min after dropwise adding. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the TCHP conversion rate is 99.7 percent, and the yield of the p-cresol is 95.8 percent.
The results of comparative examples 2 and 3 show that when the alkali + ammonium salt decomposition method is used, a large amount of water is required for multiple treatments to perform subsequent acidolysis reactions, and a large amount of wastewater with high alkali content is generated in industrial production.
Comparative example 4
Using 100g of the oxidation product mixture 1 of cymene of example 1 as a starting material, 10g of 12% NaOH aqueous solution was added and the reaction was carried out at 80 ℃ under normal pressure for 0.5 hour. The detection and analysis result of the liquid chromatography Ultimate3000 shows that the PCHP decomposition rate is 62 percent, and the TCHP retention rate is 99.0 percent.
Comparative example 5
Using mixture 1 in example 1 as a starting material, 200g of CaO was used in place of 200g of A26-OH strongly basic ion exchange resin, and the same procedure (2) as in example 1 was repeated, and the results of liquid chromatography Ultimate3000 detection and analysis showed that PCHP was decomposed by 30.0% and TCHP was retained by 99.5%.
The results of comparative example 5 show that the solid CaO is used as the catalyst for reaction, the decomposition rate of PCHP is greatly reduced, the generation of alkali-containing wastewater can be avoided, but the elution rate is not high, and the solid calcium oxide is not suitable for replacing a sodium hydroxide aqueous solution for application due to small specific surface area, weak alkalinity and low activity.
Comparative example 6
Preparation of a supported solid base catalyst: mixing Na2CO3Preparing a solution with the concentration of 15%, putting the H beta molecular sieve into the solution for dipping according to the solid-liquid mass ratio of 1: 1-5, stirring for 1-2H at 50-80 ℃, performing rotary evaporation to dryness, drying in a 100 ℃ oven for 6-12H, and roasting in a muffle furnace for 5-10H at 800-1000 ℃ to obtain the catalyst;
using mixture 1 of example 1 as a starting material, 200g of the supported solid base catalyst prepared in comparative example 6 was used in place of 200g A26-OH strong basic ion exchange resin, and the same procedure (2) of example 1 was repeated, and the results of liquid chromatography Ultimate3000 detection analysis showed that PCHP was decomposed by 10.3% and TCHP was retained by 99.8%.
The results of comparative example 6 show that the decomposition rate of PCHP is greatly reduced by using another supported solid base catalyst as the catalyst, and the reaction rate may be reduced due to weak basicity of sodium carbonate, small pore channels of the molecular sieve and difficult mass transfer.
Claims (10)
1. A process for the selective decomposition of oxygenated cymene, comprising:
under the catalysis of strong basic ion exchange resin, carrying out selective decomposition reaction on PCHP in the oxidation product of the cymene to obtain a reserved TCHP product;
the oxidation product of the cymene contains PCHP and TCHP.
2. The method of claim 1, wherein the strongly basic ion exchange resin is packed in a fixed bed reactor, and the oxidation product of cymene is continuously fed into the fixed bed reactor for reaction.
3. The method for selectively decomposing an oxidation product of cymene according to claim 1 or 2, wherein the reaction temperature is 50 to 90 ℃ and the reaction pressure is 0 to 0.5 MPa.
4. The method for selectively decomposing the oxidation product of cymene according to claim 3, wherein the reaction temperature is 80-90 ℃.
5. The method for selectively decomposing the oxidation product of cymene as claimed in claim 2, wherein the feeding space velocity of the oxidation product of cymene is 0.5-1.0 h-1。
6. The method of claim 1, wherein the strongly basic ion exchange resin is one or more selected from AmberLite HPR900 OH, Amberlyst A26OH, AmberLite FPA40 Cl, and AmberLite FPA98 Cl.
7. The process of claim 1, wherein the strongly basic ion exchange resin is a macroporous ion exchange resin.
8. The method for selectively decomposing an oxidation product of cymene according to claim 1, wherein said oxidation product of cymene is a reaction solution obtained by oxidation of cymene or a product obtained by post-treatment of the reaction solution.
9. The production process of cresol is characterized by comprising the following steps:
(1) performing oxidation reaction on cymene and oxygen or oxygen-containing gas to obtain an cymene oxidation product;
(2) treating the oxidation product of the cymene by adopting the decomposition method of any one of claims 1 to 8 to obtain a decomposition product;
(3) and carrying out acidolysis on the decomposition product to obtain cresol.
10. The process for producing a cresol according to claim 9, wherein the decomposition product obtained in the step (2) is subjected to acid hydrolysis directly after removing unreacted cymene by distillation.
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| CN1079952A (en) * | 1992-05-27 | 1993-12-29 | 住友化学工业株式会社 | The production technique of cresols |
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| CN1764637A (en) * | 2003-02-28 | 2006-04-26 | 国际壳牌研究有限公司 | Method |
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