CN107286005B - Method for preparing p-diacetylbenzene by homogeneous oxidation of p-diethylbenzene - Google Patents
Method for preparing p-diacetylbenzene by homogeneous oxidation of p-diethylbenzene Download PDFInfo
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- CN107286005B CN107286005B CN201610217339.6A CN201610217339A CN107286005B CN 107286005 B CN107286005 B CN 107286005B CN 201610217339 A CN201610217339 A CN 201610217339A CN 107286005 B CN107286005 B CN 107286005B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
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Abstract
The invention relates to a method for preparing p-diacetylbenzene by homogeneous oxidation of p-diethylbenzene. The method takes p-diethylbenzene as a raw material, takes soluble metal salt as a catalyst, adds an oxidant, an auxiliary agent and a solvent, and uniformly stirs to react to obtain the product p-diacetylbenzene. The method has the advantages of mild reaction conditions, simple operation, high conversion rate of p-diethylbenzene and high yield of p-diacetylbenzene, low catalyst consumption, low energy consumption, high reaction safety, high economic benefit and the like, and has wide industrial application prospect.
Description
Technical Field
The invention relates to a method for preparing p-diacetylbenzene by homogeneous phase selective catalytic oxidation of p-diethylbenzene, belonging to the technical field of fine chemical engineering.
Background
The p-diacetylbenzene is an important chemical intermediate and is mainly applied to the production fields of permanent waving agents, medicines, pesticides and the like. At present, no large-scale device for producing p-diacetylbenzene exists in China, the industrially used p-diacetylbenzene mainly depends on import, and the p-diethylbenzene is in a situation of passing supply and demand in China, so that the development of the synthesis process for preparing the p-diacetylbenzene by directly oxidizing the p-diethylbenzene has wide market prospect and great economic value.
The main production method of the prior p-diacetylbenzene is Friedel-Crafts acylation reaction by using AlCl3Is a catalyst. Patent EP 1053990a2 discloses a process for the preparation of aromatic compounds containing two or more acyl groups by catalytic oxidation of alkylaromatic hydrocarbons containing two or more methylene groups, using at least one metal compound and at least one of ammonia, an organic base or an onium halide salt as catalyst, a halogen-containing compound as promoter and oxygen as oxidant, in the absence or presence of a solvent. In the provided process, the metal compound is preferably soluble metal salt, the cation is preferably cobalt, manganese and cerium, the anion is preferably chlorine, bromine and acetic acid, the organic base is preferably tertiary amine compound, and the halogen compound is preferably bromine-containing compound. When the reaction was carried out at a reaction temperature of 120 ℃ for 40 hours, the conversion of p-diethylbenzene was 87.4% and the yield of p-diacetobenzene was 22%. In the absence of added pyridine and hydrobromic acid, the conversion of p-diethylbenzene was only 27.4% and the yield of p-diacetylbenzene was only 4.78%. The provided process has the following disadvantages:
(1) in the process, ammonia water and organic alkali are added, so that equipment is easily and seriously corroded, the equipment investment cost and the operation cost are increased, and potential safety hazards are left;
(2) various catalysts and auxiliaries are added in the process, but the conversion rate of p-diethylbenzene and the yield of p-diacetylbenzene are still low, the catalytic activity of the catalyst is low, raw materials are wasted, the production cost is increased, and difficulty is caused for the separation of products;
(3) the presence of water in the process is liable to cause hydrolysis of the soluble metal salt and is also detrimental to the contact of the reaction raw materials with the active components of the catalyst. The water generated in the reaction needs to be separated and removed at any time in the generation process, so that the process is complex, the equipment investment and the operation cost are increased, and the load and the cost of three-waste treatment are increased by the generated wastewater;
(4) in the process, the air flow velocity is too large, so that more oxidant is needed, the oxidation efficiency is reduced, and energy and resources are wasted.
Patent CN 101759541A discloses a method for preparing p-diethylbenzene by biomimetic catalytic oxygen oxidation of p-diethylbenzene. The method comprises the steps of taking p-diethylbenzene as a raw material, selecting any one or combination of 1-30 ppm of mononuclear metalloporphyrin and mu-oxo-dinuclear metalloporphyrin as a catalyst under the conditions of normal pressure and no solvent, introducing oxygen at the flow rate of 10-60 mL/min, initiating reaction at 140-170 ℃, and then reacting at 80-130 ℃ for 10-20 hours to obtain p-diacetylbenzene. The maximum conversion of p-diethylbenzene in the example provided is 93.2%, corresponding to a yield of p-diethylbenzene of 59.8%. The method has the advantages of high-temperature initiation, quick start, shortened reaction time and improved reaction efficiency, but has the advantages of higher reaction temperature, higher energy consumption, complex catalyst structure, expensive porphyrin-like metal complex, higher catalyst preparation cost, lower yield of the p-diacetylbenzene and more byproducts, inconvenience for separation and purification of a back-end product and great improvement on production cost.
DE 1245361B discloses a process for oxidizing 1, 4-diisopropenylbenzene in the molten state to p-isopropenylacetophenone and p-diacetophenone by the introduction of air or oxygen. Under the conditions that the reaction temperature is 100 ℃, the oxygen adding speed is 0.5L/h, and the reaction time is 41h, the yield of the p-diacetylbenzene is about 20-30%. Although the provided process does not need a solvent and uses clean and pollution-free oxygen as an oxidant, the reaction time is too long, the energy consumption is high, the potential safety hazard is high, and the yield of the p-diacetylbenzene is low, so that the process is not widely applied in industry.
The method for synthesizing p-diacetylbenzene by oxidizing ethyl acetophenone with potassium permanganate is reported by cinnabar (fine petrochemical, 2011) and the like, magnesium oxide, concentrated nitric acid and a large amount of water are required to be added in the reaction process, then the mixture is continuously stirred for 4.5 hours at the temperature of 58-62 ℃, and the separation yield of the p-diacetylbenzene is 63.5% by adopting benzene as an extracting agent. Although the method has low reaction temperature and short reaction time, concentrated nitric acid and a large amount of water are added in the reaction process, so that the resource waste is caused, the waste liquid is difficult to treat, and the toxic and harmful benzene is adopted as an extracting agent to pollute the environment and is difficult to recycle.
Lelinsha (chemical reagent, 2012) et al reported a process for synthesizing p-diethylbenzene from p-diethylbenzene. 13.4g of p-diethylbenzene and 0.001g of self-made tetraphenylcobaloporphyrin chloride catalyst are added into a 100mL three-necked flask, oxygen is introduced at the flow rate of 40mL/min, the mixture is stirred at 150 ℃ for reaction for 12h and then filtered, petroleum ether or ethanol water solution is used for washing to obtain white solid, water is used for recrystallization, white needle-shaped solid is obtained after drying, and the yield of the p-diacetylbenzene is 55.5 percent finally. The method has the advantages of high reaction temperature, high catalyst price, complex preparation method and still-to-be-researched catalyst stability.
In summary, the prior p-diacetylbenzene synthesis process has the following problems:
(1) in the synthesis process, corrosive substances such as strong acid or strong base are required to be added, a large amount of wastewater is generated, the environment is polluted, and equipment corrosion is caused, so that higher requirements on the corrosion resistance of the equipment are provided, and the investment cost of the equipment is increased;
(2) the temperature required by the synthesis reaction is high, the energy consumption is high, the equipment requirement and the operation cost are greatly improved, and potential safety hazards exist;
(3) the catalyst activity is low, so that the conversion rate of p-diethylbenzene and the yield of p-diacetylbenzene are low, byproducts generated in the synthesis process are increased, and the difficulty in separation and purification of subsequent products is increased;
(4) the reaction time is long and the reaction efficiency is low.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide the method for preparing the p-diacetylbenzene by the homogeneous phase selective catalytic oxidation of the p-diethylbenzene, which has the advantages of simple catalyst structure, reasonable price, strong catalytic activity, short reaction time, low reaction temperature, high product yield and environmental protection.
The purpose of the invention is realized by the following technical scheme:
the invention relates to a method for preparing p-diacetylbenzene by homogeneous phase selective catalytic oxidation of p-diethylbenzene, which comprises the following steps: the method comprises the steps of taking p-diethylbenzene as a raw material, taking soluble metal salt as a catalyst, adding an oxidant, an auxiliary agent and a solvent, wherein the feeding flow rate of the oxidant is 4-300 mL/h, the molar ratio of the auxiliary agent to the p-diethylbenzene is 0-10, the volume ratio of the solvent to the p-diethylbenzene is 1-20, the stirring speed is 200-500 r/min, the reaction temperature is 50-100 ℃, and the reaction time is 2-6 h, so that the product p-diacetylbenzene is obtained.
The purity of the p-diethylbenzene is 85-99.5 wt%.
The active metal of the catalyst for selectively catalyzing and oxidizing p-diethylbenzene to prepare p-diacetylbenzene is Fe (NO)3)3·9H2O、NiCl2·6H2O、MnSO4·H2O、Co(CH3COO)2·4H2O、Cu(NO3)2·3H2O、CuSO4·5H2O、Co(NO3)2·6H2One or a mixture of more than two of O in any proportion.
The molar ratio of the catalyst to the p-diethylbenzene is 0.05-0.5: 1.
the oxidant is one of oxygen, hydrogen peroxide or tert-butyl hydroperoxide.
The assistant is one or two of potassium bromide, potassium chloride or sodium iodide.
The solvent is one of glacial acetic acid, DMF or acetonitrile.
Compared with the prior method for synthesizing p-diacetylbenzene, the method has the following beneficial effects:
(1) the invention adopts the homogeneous catalyst for selectively catalyzing and oxidizing the p-diethylbenzene to prepare the p-diethylbenzene, and the catalyst has the advantages of simple structure, lower cost, stronger mass transfer capacity and stronger catalytic activity;
(2) the reaction temperature is 50-100 ℃, the reaction temperature is low, the energy consumption is reduced, the cost is saved, and the safety is improved;
(3) the reaction time is 2-6 h, the reaction time is short, the reaction efficiency is greatly improved, and the reaction energy consumption and the operation cost are reduced;
(4) the invention does not use strong acid or strong alkali, reduces the corrosion to equipment, reduces the environmental pollution and reduces the equipment investment cost;
(5) the method does not use toxic solvent, eliminates the harm of the toxic solvent to the environment, and reduces the cost for treating three wastes;
(6) the method has the advantages of high conversion rate of the p-diethylbenzene, high yield of the p-diacetylbenzene selective base, increased product yield and reduced product separation difficulty and energy consumption.
Detailed Description
Example 1
1mL of p-diethylbenzene with purity of 85 wt% was added to a 50mL three-necked flask and the catalyst was Fe (NO)3)3·9H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.05, oxygen is introduced at the flow rate of 300mL/h, no auxiliary agent is added, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 10, and when the reaction temperature is 50 ℃, the reaction time is 2h and the stirring speed is 500r/min, the conversion rate of the p-diethylbenzene is 87.7 percent, the selectivity of the p-diacetylbenzene is 58.1 percent and the yield is 50.6 percent.
Example 2
In a 50mL three-neck flask, 1mL of p-diethylbenzene with purity of 85 wt% was added and catalyst was NiCl2·6H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, oxygen is introduced at the flow rate of 300mL/h, the molar ratio of the auxiliary agent NaCl to the p-diethylbenzene is 5, the volume ratio of the solvent DMF to the p-diethylbenzene is 1, and when the reaction temperature is 50 ℃, the reaction time is 2h and the stirring speed is 500r/min, the conversion rate of the p-diethylbenzene is 88.4 percent, the selectivity of the p-diacetylbenzene is 57.9 percent, and the yield is 51.2 percent.
Example 3
2mL of p-diethylbenzene with the purity of 90 wt% is added into a 100mL three-neck flask, and the catalyst is MnSO4·H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, oxygen is introduced at the flow rate of 300mL/h, the molar ratio of the auxiliary agent NaCl to the p-diethylbenzene is 5, and solvents of acetonitrile and the p-diethylbenzeneThe volume ratio is 10, the conversion rate of the diethylbenzene is 91.3 percent, the selectivity of the p-diacetylbenzene is 60.2 percent and the yield is 55.0 percent when the reaction temperature is 80 ℃, the reaction time is 4 hours and the stirring speed is 500 r/min.
Example 4
In a 100mL three-neck flask, 2mL of p-diethylbenzene with purity of 90 wt% was added and the catalyst was Co (CH)3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, oxygen is introduced at the flow rate of 300mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 5, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 10, and when the reaction temperature is 80 ℃, the reaction time is 4h and the stirring speed is 500r/min, the conversion rate of the p-diethylbenzene is 90.4%, the selectivity of the p-diacetylbenzene is 62.3% and the yield is 56.3% are measured.
Example 5
5mL of p-diethylbenzene with a purity of 99 wt% was added to a 250mL three-necked flask in the presence of Cu (NO) as a catalyst3)2·3H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.1, the tert-butyl hydroperoxide is introduced at the flow rate of 5mL/h, the molar ratio of the auxiliary NaCl to the p-diethylbenzene is 5, the volume ratio of the solvent DMF to the p-diethylbenzene is 1, and when the reaction temperature is 50 ℃, the reaction time is 2h and the stirring speed is 200r/min, the conversion rate of the p-diethylbenzene is 89.8 percent, the selectivity of the p-diacetylbenzene is 59.5 percent and the yield is 53.4 percent are measured.
Example 6
In a 250mL three-neck flask, 5mL of p-diethylbenzene with a purity of 99.5 wt% was added and the catalyst was Fe (NO)3)3·9H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.5, oxygen is introduced at the flow rate of 300mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 10, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 20, and when the reaction temperature is 100 ℃, the reaction time is 6h and the stirring speed is 500r/min, the conversion rate of the p-diethylbenzene is 93.4%, the selectivity of the p-diacetylbenzene is 61.8% and the yield is 57.7% are measured.
Example 7
In a 50mL three-neck flask, 1mL of p-diethylbenzene with a purity of 99.5 wt% was added and the catalyst was NiCl2·6H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.1, hydrogen peroxide is introduced at the flow rate of 10mL/h, the molar ratio of the auxiliary agent NaBr to the p-diethylbenzene is 5, the volume ratio of the solvent DMF to the p-diethylbenzene is 1, and when the reaction temperature is 50 ℃, the reaction time is 4h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 91.9 percent, the selectivity of the p-diacetylbenzene is 60.4 percent and the yield is 55.5 percent are measured.
Example 8
1mL of p-diethylbenzene with a purity of 99.5 wt% was added to a 50mL three-necked flask in the presence of CuSO as a catalyst4·5H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.5, hydrogen peroxide is introduced at the flow rate of 4mL/h, the molar ratio of the auxiliary agent NaBr to the p-diethylbenzene is 5, the volume ratio of the solvent acetonitrile to the p-diethylbenzene is 10, and when the reaction temperature is 50 ℃, the reaction time is 6h and the stirring speed is 200r/min, the conversion rate of the p-diethylbenzene is 92.6 percent, the selectivity of the p-diacetylbenzene is 63.6 percent and the yield is 58.9 percent are measured.
Example 9
1mL of p-diethylbenzene with a purity of 99.5 wt% was added to a 50mL three-necked flask in the presence of Cu (NO) as a catalyst3)2·3H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.1, hydrogen peroxide is introduced at the flow rate of 10mL/h, the molar ratio of the auxiliary agent NaBr to the p-diethylbenzene is 10, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 10, and when the reaction temperature is 100 ℃, the reaction time is 4h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 94.1%, the selectivity of the p-diacetylbenzene is 57.4% and the yield is 54.0% are measured.
Example 10
1mL of p-diethylbenzene with a purity of 99.5 wt% was added to a 50mL three-necked flask and Co (NO) was used as a catalyst3)2·6H2O and Cu (NO)3)2·3H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.1, the tert-butyl hydroperoxide is introduced at the flow rate of 4mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 10, the volume ratio of the solvent DMF to the p-diethylbenzene is 20, the conversion rate of the p-diethylbenzene is 98.7 percent, the selectivity of the p-diacetylbenzene is 64.7 percent, and the yield is measured at the reaction temperature of 60 ℃, the reaction time of 6h and the stirring speed of 400r/minThe content was 63.9%.
Example 11
1mL of p-diethylbenzene with the purity of 99.5 wt% was added into a 50mL three-necked flask, and the catalyst was MnSO4·H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, the tert-butyl hydroperoxide is introduced at the flow rate of 4mL/h, the molar ratio of the auxiliary agent NaCl-NaBr to the p-diethylbenzene is 2, the volume ratio of the solvent DMF to the p-diethylbenzene is 10, and when the reaction temperature is 60 ℃, the reaction time is 4h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 91.1 percent, the selectivity of the p-diacetylbenzene is 57.2 percent and the yield is 52.1 percent are measured.
Example 12
In a 50mL three-necked flask, 1mL of p-diethylbenzene having a purity of 99.5 wt% was added and Co (CH) was used as a catalyst3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.1, oxygen is introduced at the flow rate of 300mL/h, the molar ratio of the auxiliary agent NaCl to the p-diethylbenzene is 5, the volume ratio of the solvent DMF to the p-diethylbenzene is 10, and when the reaction temperature is 60 ℃, the reaction time is 6h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 94.3 percent, the selectivity of the p-diacetylbenzene is 61.5 percent, and the yield is 58.0 percent.
Example 13
In a 50mL three-necked flask, 1mL of p-diethylbenzene having a purity of 99.5 wt% was added and Co (CH) was used as a catalyst3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, hydrogen peroxide is introduced at the flow rate of 10mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 2, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 5, and when the reaction temperature is 80 ℃, the reaction time is 6h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 97.4%, the selectivity of the p-diacetylbenzene is 72.3% and the yield is 70.4% are measured.
Example 14
In a 50mL three-necked flask, 1mL of p-diethylbenzene having a purity of 99.5 wt% was added and Co (CH) was used as a catalyst3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, hydrogen peroxide is introduced at the flow rate of 10mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 2, and solvents of glacial acetic acid and p-diethylbenzene areThe volume ratio of the ethyl benzene is 10, the conversion rate of the diethyl benzene is 99.8 percent, the selectivity of the p-diacetylbenzene is 80.2 percent and the yield is 80.0 percent when the reaction temperature is 80 ℃, the reaction time is 6 hours and the stirring speed is 400 r/min.
Example 15
In a 50mL three-necked flask, 1mL of p-diethylbenzene having a purity of 99.5 wt% was added and Co (CH) was used as a catalyst3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, hydrogen peroxide is introduced at the flow rate of 10mL/h, the molar ratio of the auxiliary agent KBr to the p-diethylbenzene is 2, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 10, and when the reaction temperature is 80 ℃, the reaction time is 4h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 98.7%, the selectivity of the p-diacetylbenzene is 74.2% and the yield is 73.2% are measured.
Example 16
In a 50mL three-necked flask, 1mL of p-diethylbenzene having a purity of 99.5 wt% was added and Co (CH) was used as a catalyst3COO)2·4H2O, the molar ratio of the catalyst to the p-diethylbenzene is 0.2, hydrogen peroxide is introduced at the flow rate of 10mL/h, no auxiliary agent is added, the volume ratio of the solvent glacial acetic acid to the p-diethylbenzene is 10, and when the reaction temperature is 80 ℃, the reaction time is 6h and the stirring speed is 400r/min, the conversion rate of the p-diethylbenzene is 86.4%, the selectivity of the p-diacetylbenzene is 56.7% and the yield is 49.0%.
Claims (3)
1. A method for preparing p-diacetylbenzene by homogeneous oxidation of p-diethylbenzene is characterized in that p-diethylbenzene is taken as a raw material, a catalyst, an oxidant, an auxiliary agent and a solvent are added, and the mixture is uniformly stirred for reaction to obtain a product p-diacetylbenzene;
wherein the feeding flow rate of the oxidant is 4-300 mL/h, the molar ratio of the auxiliary agent to the p-diethylbenzene is 0-10: 1, the volume ratio of the solvent to the p-diethylbenzene is 1-20: 1, and the purity of the raw material p-diethylbenzene is 85-99.5 wt%;
the catalyst is selected from Fe (NO)3)3·9H2O、NiCl2·6H2O、MnSO4·H2O、Co(CH3COO)2·4H2O、Cu(NO3)2·3H2O、CuSO4·5H2O、Co(NO3)2·6H2One or a mixture of more than two of O in any proportion;
the reaction temperature is 50-100 ℃, and the reaction time is 2-6 h;
the molar ratio of the catalyst to the p-diethylbenzene is 0.05-0.5: 1;
the oxidant is any one of oxygen, hydrogen peroxide or tert-butyl hydroperoxide;
the auxiliary agent is one or two of potassium bromide, potassium chloride or sodium iodide.
2. The process for the homogeneous oxidation of para-diethylbenzene to para-diethylbenzene as described in claim 1 wherein said solvent is one of glacial acetic acid, DMF or acetonitrile.
3. The method for preparing p-diethylbenzene by homogeneous oxidation of p-diethylbenzene as claimed in claim 1, wherein the stirring speed is 200 to 500 r/min.
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| US4162268A (en) * | 1976-10-22 | 1979-07-24 | Asahi Kasei Kogyo K.K. | Process for preparing diacetylbenzene |
| CN101759541A (en) * | 2010-01-29 | 2010-06-30 | 北京工业大学 | Method for preparing p-diacetylbenzene by biomimetic catalytic oxidation of p-diethylbenzene with oxygen |
| CN102675072A (en) * | 2012-05-28 | 2012-09-19 | 华南理工大学 | Method for producing acetophenone through catalytic oxidation of ethylbenzene |
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