The method of producing ethylbenzene hydroperoxide

 

(57) Abstract:

The invention relates to the petrochemical industry and can be used in the process of joint production of propylene oxide and styrene. The purpose of the invention: increasing the selectivity of the formation of ethylbenzene hydroperoxide. This goal is achieved by way of liquid-phase catalytic oxidation of ethylbenzene to ethylbenzene hydroperoxide at a high temperature oxygen-containing gas in the presence as catalyst of a mixture of compounds of metals of constant valency 1A and/or 2A groups C-d and/or 4-year periods and variable valence 7 and/or 8 groups of the 4th period of the periodic system, taken in the aggregate amount calculated on the metal 0,0001,0031 wt. % by total weight ratio of metal of constant valency metals of variable valence equal 300-1:1-100. The catalyst may be pre-treated at a temperature of 0-150oWith oxygen and/or nitrogen-containing organic compound and/or a peroxide compound, and/or ozone. As oxygen-containing organic compounds using organic Gidropress, ketone, alcohol, carboxylic acid or their mixture, and as azotosoderjashchig the art. The oxidation is carried out in a cascade of 3-5 reactor at a temperature of 110-160oC. the Catalyst may be introduced into the reactor with the return ethylbenzene. 4 C.p. f-crystals.

The invention relates to the petrochemical industry and can be used in the process of joint production of propylene oxide and styrene.

It is known that the gidroperekisi alkylaromatic hydrocarbons obtained by oxidation of the corresponding hydrocarbon at an elevated temperature in the presence of alkaline additives and initiator of oxidation with subsequent isolation of the target product by known methods (ed. St. USSR 259884, class C 07 C 179/035 A, publ. 22.12.69 and bull. N 3, 1979).

To improve the selectivity of the oxidation process is carried out in the presence of a catalyst is a chromium-Nickel steel containing chromium, Nickel, titanium, manganese, etc. When this catalyst can serve as a reactor or a nozzle in the form of rings or chips from the specified steel. The disadvantages of this method are the low rate of accumulation of oxidation products and a significant concentration of carboxylic acids in oxidate and, as a consequence, a significant loss of propylene oxide under epoxidation of propylene with ethylbenzene hydroperoxide.

The closest is in molecular oxygen in the liquid phase in the presence of a catalyst. The oxidation reaction is also thermally initiate unstable compounds, such as peroxides or hydroperoxides (ed.St. Czechoslovakia N 196648, class C 07 C 179/02, publ.15.11.81).

To improve the selectivity of the formation of ethylbenzene hydroperoxide, we propose a method of liquid-phase catalytic oxidation of ethylbenzene to ethylbenzene hydroperoxide at a high temperature oxygen-containing gas in the presence as catalyst of a mixture of compounds of metals of constant valency 1a and/or 2a group 3 and/or 4-year periods and variable valence 7b and/or 8b groups of the 4th period of the periodic system, taken in the aggregate amount calculated on the metal 0,0001 - 0,0031 wt.% when the total weight ratio of metal of constant valency metals of variable valence equal to 300 - 1 : 1 - 100. You can pre-treatment of the catalyst at 0 - 150oC oxygen and/or nitrogen-containing organic compound and/or a peroxide compound, and/or oxygen and/or ozone. As oxygen-containing organic compounds using organic Gidropress, ketone, alcohol, carboxylic acid or their mixture, and as a nitrogen-containing organic compounds using the basis of the Directors at a temperature of 110-160oC. the Catalyst serves to return ethylbenzene.

As compounds containing metals of constant valency and the metals with variable valence, can be used a variety of inorganic and/or organic compounds, however, the most preferred are the oxides, hydroxides, chlorides, sulfates, sulfites, sulfides, nitrides, nitrates, or mixtures thereof, alcoholate, reaction, glycolate, diketonates and carboxylates derived from mon-, di - and polycarboxylic aliphatic, aromatic and alicyclic carboxylic acids or their mixtures. The catalyst may be used in the form of solutions, suspensions or emulsions of the compounds of these metals in the initial charge applied to the oxidation and/or in solutions containing all possible oxygen-containing compounds such as water, alcohols, peroxides and hydroperoxides, ketones, ethers and esters, or mixtures thereof. In the case of the oxidation process in a cascade of reactors or in a partitioned reactor, the oxidation catalyst may be supplied in the same thread with the raw materials, starting from the first reactor or the first section, or in each reactor or section separately. Pre-processing is Kari, ketones, alcohols, organic acids or simple or esters in the presence of organic or inorganic nitrogen-containing compounds and/or molecular oxygen and/or ozone in the temperature range 0-150oC provides additional effect on increasing the selectivity and the rate of formation of hydroperoxide by placing the catalyst in the active complex.

The process in these terms allows to increase the selectivity of the formation of cumene ethylbenzene, to reduce the content of carboxylic acid in the resulting oxidate.

Example 1. The oxidation of ethylbenzene with oxygen in the air carry out the laboratory facility is equipped with reverse water and carbon dioxide refrigerators, dosing systems and control, at a temperature of 130oC and flow rate of air supply 250 h-1. Ethylbenzene is served with a speed of 4 mol/h In fed to the oxidation of ethylbenzene contains a catalyst consisting of 0,00001 wt.% benzoate of iron in the calculation of the metal, and 0.003 wt. % of a mixture of hydroxide and sodium carbonate for sodium. The ratio Na/Fe-300 g/g, the concentration of catalyst in the calculation of the metals 0,00301 wt.%.

The conversion of ethylbenzene was 8.1%. Output GPIB and Bq on unreacted ethylbenzene 91,11 and 0.96 mol.% respectively.

Example 2. The oxidation of ethylbenzene with oxygen is carried out on a laboratory setup described in example 1 at 110oC and flow rate of air supply 250 h-1. For oxidation using ethylbenzene containing a catalyst consisting of 0,0003 wt.% oksihinolina within 0.00001 wt.% phthalate manganese based on metal, of 0.003 wt.% calcium stearate based on the calcium. The ratio of Ca/Mn was 300 g/g, the concentration of catalyst 0,00301 wt.% in the calculation of the metals. Ethylbenzene fed into the oxidation reactor at a speed of 4 mol/h

At the exit of the reactor get oxidized ethylbenzene containing 0,345 mol/h GPIB, 0,0019 mol/h of acid in terms of Bq and 0,0451 mol/h other by-products.

The conversion of ethylbenzene is 9.8%. Output GPIB and Bq on proreagirovali the effect as in example 1. In the reaction zone is administered ethylbenzene containing catalyst, comprising of 0.0005 wt.% of iron acetylacetonate in the calculation of the metal within 0.00001 wt. % of potassium phenolate in the calculation of the metal and 0.0002 wt.% 2,6-ditretbutyl-4-dimethylaminomethylphenol (base manniche). The ratio K/Fe is 1:50 g/g, the concentration of catalyst 0,00051 wt.%. in the calculation of the metals. The mixture is supplied to the oxidation, prior to feeding into the reactor maintained at 130oC for 1 min.

At the exit of the reactor get oxidized ethylbenzene containing 0,3326 mol/h GPEB. The conversion of ethylbenzene is 9.3%. Output GPIB unreacted ethylbenzene 89,4 mol.%.

Example 4. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 1. In the reaction zone is administered ethylbenzene containing in suspension a mixture of 0.0001 wt.% oxide of Nickel in the calculation of the metal within 0.00001 wt.% ethylate magnesium per metal and 0.05 wt.% the hydrogen peroxide. The ratio of Mg/Ni is 1:10 g/g, the concentration of catalyst 0,00011 wt.% in the calculation of the metals. Before feeding into the reactor oxidation of ethylbenzene containing hydrogen peroxide and metal compounds, heated to a temperature of 100oC and kept at this temperature 15 C.

On leaving react to 8.1%. Output GPIB on unreacted ethylbenzene 90,3 mol.%.

Example 5. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 1.

In the reaction zone is administered ethylbenzene containing a suspension of 0.0001 wt.%. sodium sulfate and 0.0005 wt.% nitrate of cobalt per metal. The ratio Na/Co 1:5 g/g, the concentration of catalyst 0,0006 wt.% in the calculation of the metals. Prepared suspensions of the compounds of sodium and cobalt in water before entry into the reactor is treated at a temperature of 150oC oxygen within 8 minutes

The output of the plant to get oxidized ethylbenzene containing 0,353 mol/h GPIB.

The conversion of ethylbenzene 9.7%. Output GPIB on unreacted ethylbenzene 91,02 mol.%.

Example 6. The oxidation of ethylbenzene with oxygen is carried out on a laboratory setup of example 1 according to the proposed method at 150oC and flow rate of air supply 100 h-1. Ethylbenzene and the catalyst containing dissolved iron compounds in an amount of 0.0001 wt.% in the calculation of the metal derived from trimethylsilanol acid and 0.0005 wt.% in the calculation of the metal derivative, obtained on the basis of KOHN and benzene-1,2,3,4,5-tetracarboxylate 0,0006 wt.% in the calculation of the metals.

The output of the plant to get oxidized ethylbenzene containing of 0.56 mol/h GPIB.

The conversion of ethylbenzene is 15%. Output GPIB on unreacted ethylbenzene to 92.1 mol.%.

Example 7. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is administered ethylbenzene, the catalyst containing 0,0006 wt. % (based on the reaction to the weight of the mixture of adipinate calcium and iron concentration of 0.0005 and 0.0001 wt.% in the calculation of the metal, respectively, taken in a weight ratio of Ca/Fe equal to 5:1, and also containing about 0.001 wt.% methylphenylcarbinol, 0.01 wt.% of acetophenone and 0.015 wt.% the gidroperekisi ethylbenzene. Ethylbenzene such structure serves to oxidation at 150oC.

The output of the plant to get oxidized ethylbenzene containing 0,572 mol/h GPIB.

The conversion of ethylbenzene is 15.3 per cent. Output GPIB on unreacted ethylbenzene 93,2 mol.%.

Example 8. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is administered ethylbenzene containing as catalyst 0.005 wt.% methylphenylcarbinol, 0.005 wt.% of acetophenone, 0.005 wt.% the gidroperekisi ethylbenzene, 0.005 wt.% hydrogen peroxide and 0.001 wt.% a mixture of resinato potassium, calcium, D. fed into the oxidation reactor is heated to 150oC and maintained at this temperature for 10 minutes

At the exit of the reactor get oxidized ethylbenzene containing 0.55 mol/h GPIB.

The conversion of ethylbenzene is 14.8%. Output GPIB on unreacted ethylbenzene 92,7 mol.%.

Example 9. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is injected emulsion catalyst consisting of ethylbenzene containing 0.01 wt.% methylphenylcarbinol, 0.005 wt.% acetophenone and 0.08 wt. % gidroperekisi ethylbenzene and 0,0009 wt.% in the calculation of the metal mixture glycolate, sodium and calcium and hexahydrophthalate iron and manganese in triethylene glycol, taken in a weight ratio of (Na+Ca)/(Fe+Mn) equal to 6:1.

At the outlet of the oxidation reactor get oxidized ethylbenzene containing 0,605 mol/h GPIB.

The conversion of ethylbenzene is 16,1%. Output GPIB on unreacted ethylbenzene 93,8 mol.%.

Example 10. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is administered ethylbenzene and the catalyst containing 0,0009 wt. % mixture of compounds sodium nitrite, benzoate calcium and iron, and manganese chloride, taken in a weight ratio in the calculation of the metal (Na+Ca)/(Fe+Mn), is Anzola. In this mixture before entry into the reactor is also introduced to 0.0001 wt.% oksihinolina.

At the exit of the reactor get oxidized ethylbenzene containing 0,57 mol/h GPIB.

The conversion of ethylbenzene is 15,41%. Output GPIB on unreacted ethylbenzene of 92.5 mol.%.

Example 11. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is administered ethylbenzene containing about 0.001 wt.% in the calculation of the reaction mass is a mixture of glycolate, sodium and iron phenolate, taken in a weight ratio of Na/Fe of 1:100. The charge to the oxidation containing a mixture of compounds of metals of constant and variable valence, enter oxidized ethylbenzene containing 25 wt.% the gidroperekisi and 0.0001 wt.% diethylhydroxylamine. The mixture of solutions is carried out at 100oC for 1 min Content gidroperekisi ethylbenzene in the resulting charge on the oxidation of 0.5 wt.%.

At the outlet of the oxidation reactor get oxidized ethylbenzene containing of 0.56 mol/h GPIB.

The conversion of ethylbenzene is 15,23%. Output GPIB on unreacted ethylbenzene to 91.8 mol.%.

Example 12. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone is introduced as katal is the ratio Na/Fe, equal to 100:1, in the form of a solution in benzene fed to the oxidation. The solution oxyhydrate iron and sodium sulfide in the ethylbenzene before putting them into the mixture in the oxidation process ozone at 25oC for 5 minutes

At the exit of the reactor get oxidized ethylbenzene, containing 0.62 mol/h GPIB, 0,0035 mol/h of acid in terms of Bq and 0,022 mol/h other by-products.

The conversion of ethylbenzene is 15,63%, Output GPIB and Bq on unreacted ethylbenzene 95,8 and of 0.48 mol.% respectively.

Example 13. The oxidation of ethylbenzene with oxygen is carried out in a cascade of five reactors at a temperature of 150oC, the supply of ethylbenzene 4 mol/h and flow rate of air supply 100 h-1.

In the reaction zone of the first reactor introduced ethylbenzene containing of 0.0005 wt. % (based on the weight of the mixture of the reaction of benzoate in the reaction of sodium and iron taken in a weight ratio of Na/Fe equal to 50:1. In a solution of compounds of iron and sodium in benzene before putting them into the mixture for oxidation of injected base manniche in the amount of 0.0001 wt.% when 30oC. In other reactors of the cascade impose additional 1 wt.% etilbenzene mixture containing components of the catalyst.

The conversion of ethylbenzene is 15,63%. Output GPIB and Bq on unreacted ethylbenzene 95,8 and of 0.48 mol.% respectively.

Example 14. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 13. In a solution of compounds of iron and sodium in benzene before putting them into the mixture for oxidation of the injected mixture of Mannich bases and ethylhydroxylamine in the number 0,00015 wt.%, the pre-treated mixture containing 25 wt.% the gidroperekisi ethylbenzene and 2 wt.% hydrogen peroxide (50oC for 20 minutes In the other reactors of the cascade impose additional 1 wt.% etilbenzene mixture containing components of the catalyst.

At the outlet of the last reactor of the cascade get oxidized ethylbenzene containing of 0.58 mol/h GPEB. The conversion of ethylbenzene is 15,63%. Output GPIB and Bq on unreacted ethylbenzene 92,73 mol.%.

Example 15. The oxidation of ethylbenzene with oxygen is carried out in a cascade of three reactors according to the method of example 13. In a solution of compounds of iron and sodium in benzene before putting them into the mixture for oxidation of the injected mixture of Mannich bases and oksihinolina in the number 0,00015 wt.%, the pre-treated mixture containing 25 wt.% Gidropark the% of benzaldehyde at 0oC for 40 minutes In the other reactors of the cascade impose additional 1 wt.% etilbenzene mixture containing components of the catalyst.

At the outlet of the last reactor of the cascade get oxidized ethylbenzene containing 0,57 mol/h GPIB.

The conversion of ethylbenzene is 15.9 per cent. Output GPIB on unreacted ethylbenzene to 92.1% mol.

Example 16. The oxidation of ethylbenzene with oxygen of the air is carried out as in example 6. In the reaction zone to impose the charge, consisting of ethylbenzene containing 0.01 wt.% methylphenylcarbinol, of 0.003 wt.% of acetophenone and 0.005 wt.% the gidroperekisi ethylbenzene, and 0,0008 wt.% in the calculation of the metal mixture of benzoate and formate sodium and iron taken in a weight ratio of Na/Fe equal to 7:1. The entire catalyst is introduced with the return flow of ethylbenzene entering site batch preparation stages with strengthening oxidized ethylbenzene and separation of epoxide. The number of return ethylbenzene in etilbenzene the charge is 80%. The oxidation is carried out at 160oC.

At the outlet of the oxidation reactor get oxidized ethylbenzene containing 0,602 mol/h GPIB.

The conversion of ethylbenzene is 16%. Output GPIB on unreacted ethylbenzene 91,wt.% in the calculation of the reaction mass allows to obtain oxidized ethylbenzene, containing up to 16 wt.% GPIB with the selectivity of the formation of GPB to 96 mol.%.

1. The method of obtaining cumene ethylbenzene liquid-phase catalytic oxidation of ethylbenzene oxygen-containing gas at elevated temperature, characterized in that as the catalyst, a mixture of compounds of metals of constant valency 1A and/or 2A groups of the 3rd and/or 4th periods and variable valence 7b and/or 8b groups of the 4th period of the Periodic table of elements, taken in the aggregate amount calculated on the metal 0,0001-0,0031 wt. % by total weight ratio of metal of constant valency metals of variable valence equal 300-1 : 1-100.

2. The method according to p. 1, wherein the used catalyst, pretreated at a temperature of 0-150oC oxygen and/or nitrogen-containing organic compound and/or a peroxide compound, and/or oxygen and/or ozone.

3. The method according to PP.1 and 2, characterized in that as the oxygen-containing organic compounds using organic Gidropress, ketone, alcohol, carboxylic acid or their mixture, and as a nitrogen-containing organic compounds used according to manniche, oksihinolina-, al in the cascade of 3-5 reactor at a temperature of 110-160oC.

5. The method according to PP.1-4, characterized in that the catalyst is introduced into the reactor with the return ethylbenzene.

 

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