Method for preparation of cyclohexylisopropylbenzene hydroperoxide

FIELD: chemistry.

SUBSTANCE: present invention refers to the method for preparation of cyclohexylisopropylbenzene hydroperoxide which can be used as initiator of unsaturated hydrocarbons emulsion polymerisation. According to the invention cyclohexylisopropylbenzene hydroperoxide is prepared by oxidation of cyclohexylisopropylbenzene with air oxygen at temperature 100-120°C and atmospheric pressure during 1-3 hrs in the presence of catalyst N-hydroxyphthalimide up to cyclohexylisopropylbenzene hydroperoxide concentration 64%.

EFFECT: enhancing of the cyclohexylisopropylbenzene hydroperoxide formation rate; decrease of the process time and energy consumption.

1 cl, 3 tbl, 2 ex

 

The invention relates to a method for producing cumene cyclohexylpropionate, which can be used as an initiator emulsion polymerization of unsaturated hydrocarbons [1 - Gaiazova, Waalaikum, Ehitatava, USP, 21, 379 (1952)].

A method of obtaining cumene cyclohexylpropionate liquid-phase oxidation of cyclohexylpropionate oxygen at atmospheric pressure and a temperature of 100-120°C in the presence of initiators (of cumene hydroperoxide, peroxide of barium), catalyst (resinate manganese), alkaline additives (caustic soda, sodium hydroxide, calcium hydroxide). Cyclohexylpropionate in the presence of one of resinate manganese oxidizes much more slowly and less deeply than in the presence of resinate manganese and alkaline additives. Effect of additives soda and calcium hydroxide is approximately the same. For example, in the presence of resinate manganese and soda maximum content of hydroperoxide is achieved for 8 h and is 38%; in the presence of resinate manganese and calcium hydroxide, the maximum concentration of hydroperoxide is achieved for 10 h at 36%, while with one resinatum manganese for 18 h, it reaches only 21% under the same conditions. With the most high speed, about 6% in h, and the maximum concentration hydrop is rockside 61% auto-oxidation of cyclohexylpropionate proceeds in the presence of resinate manganese, soda and peroxide of barium at 118-120°C. the process Conditions, the composition of the initiator additives and catalyst are presented in tables 1, 2 [2 - Svetasreni, Weltevrede, DAN, 129, №1, 113 (1959)], [3 - Innovacom, Amentaeva, Rigilene, GOH, 32, 2955, (1962)].

A characteristic feature of the above processes is the low oxidation rate (no more than 4-5,7% of hydroperoxide per hour), long process (8-49 hours), which in some cases leads to the spontaneous decomposition of hydroperoxides, the use of a large number of inorganic material non reusable reuse. All the above leads to a significant energy consumption.

The technical purpose of this invention is to eliminate the above disadvantages, the increase in the speed of formation of cumene cyclohexylpropionate, a sharp decrease in the duration of the process, the reduction of energy consumption.

This technical problem is solved using the method of producing cumene cyclohexylpropionate by liquid-phase oxidation of cyclohexylpropionate oxygen at atmospheric pressure and a temperature of 100-120°C, in the presence as catalyst of N-hydroxyphthalimide, in an amount of 0.1-2.5% of the speakers. In these conditions it is possible to oxidize cyclohexylpropionate for 1-3 hours until the content of cumene cyclohexylpropionate ~ 64% with a selectivity of its formation more than 95%. A characteristic feature of the used catalyst is the simplicity of its receipt and the possibility of its repeated use.

The present invention is illustrated by the following examples.

Example 1

In a glass reactor with a capacity of 10 cm3downloaded 4 cm3cyclohexylpropionate and 1.6% of the mass. N-hydroxyphthalimide was given oxygen at atmospheric pressure, a temperature of 120°C for 1 h and continuous stirring. The hydroperoxide content was 63,3%. Oxidat analyzed for the content of hydroperoxide by iodometric method of analysis.

Example 2

In a glass reactor with a capacity of 10 cm3downloaded 4 cm3cyclohexylpropionate and 1.6% of the mass. N-hydroxyphthalimide was given oxygen at atmospheric pressure, a temperature of 110°C for 3 h and continuous stirring. The content of hydroperoxide to 57.0%. Oxidat analyzed for the content of hydroperoxide by iodometric method of analysis.

The results of the experiments are shown in table 3.

Table 3
The oxidation of isopropylalcohol is albenzae
no experienceThe number N of hydroxyphthalimide taken for oxidation, % of the mass.The reaction temperature, °CThe maximum content of hydroperoxide, %The time of oxidation, hThe average rate of formation of hydroperoxide, % / h
123456
11,610037,1312,4
21,611057,0319,0
123456
31,612063,3163,3
411049,2316,4
52,411052,7317,6

Obtaining cumene cyclohexylpropionate of the proposed method in comparison with the prototype is reduced to 10-50 times, energy consumption by 25-30%.

The method of obtaining cumene cyclohexylpropionate liquid-phase oxidation of cyclohexylpropionate oxygen at atmospheric pressure and a temperature of 100-120°C, in the presence of a catalyst, wherein the oxidation process is carried out in the presence as catalyst of N-hydroxyphthalimide within 1-3 hours



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining cyclohexyltoluene hydroperoxide, which can serve as source of joint obtaining of cresols and cyclohexanon and as initiator of emulsion polymerisation of unsaturated hydrocarbons. According to claimed method obtaining of cyclohexyltoluene hydroperoxide is carried out by oxidation of cyclohexyltoluene with air oxygen at atmospheric pressure in presence of catalyst N-hydroxyphtalimide at temperature of process 110-140°C, during 2-3 hours until content of cyclohexyltoluene hydroperoxide is 22.2%.

EFFECT: increase of target product formation rate, reduction of process duration and reduction of power consumption for its carrying out.

1 cl, 3 tbl, 2 ex

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of alkylaryl hydroperoxides useful as starting material in production of propylene oxide and alkenylaryl. Process of invention comprises following stages: oxidation of alkylaryl compound to form reaction product containing alkylaryl hydroperoxide; contacting at least part of reaction product with basic aqueous solution; separation of hydrocarbon phase containing alkylaryl hydroperoxide from aqueous phase; containing at least part of above hydrocarbon phase with aqueous solution containing waste water, said aqueous solution containing less than 0.2% alkali metal and/or salt (determined as ratio of metal component to total amount of solution); and separation of hydrocarbon phase from aqueous phase. By bringing at least part of above hydrocarbon phase containing alkylaryl hydroperoxide into interaction with propylene and catalyst, alkylaryl hydroxide and propylene oxide are obtained. At least part of propylene oxide is then separated from alkylaryl hydroxide. Dehydration of at least part of alkylaryl hydroxide results in formation of alkenylaryl.

EFFECT: reduced amount of contaminating by-products in alkylaryl hydroperoxide preparation stage.

8 cl, 4 ex

The invention relates to a method of obtaining-generatingcapacity of ethylbenzene oxidation of the latter with oxygen in the presence of a ternary catalyst system comprising a bis-acetylacetonate Nickel, electron-donor complexing compound, for example an alkali metal stearate - sodium or lithium, N-organic-2, hexamethylphosphorotriamide and phenol concentration (0,5-3,0)10-3mol/l,-generatingcapacity is used to obtain propylene oxide, the world production of which is more than 106tons per year, and 44% of production based on the use of EVP as epoxidised agent

The invention relates to a method of producing hydroperoxides by oxidation of hydrocarbons oxygen-containing gas in the presence of certain compounds for the selective conversion of hydrocarbons to the corresponding hydroperoxide
The invention relates to the petrochemical industry and can be used in the process of joint production of propylene oxide and styrene
The invention relates to the petrochemical industry and can be used in the process of joint production of propylene oxide and styrene

The invention relates to a reactor unit to obtain gidroperekisi ethylbenzene oxidation of ethylbenzene oxygen-containing gas (oxygen) and can be used to obtain, respectively, of hydroperoxides of isobutane and isopentane

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

The invention relates to a method for producing aliphatic and alkylaromatic hydroperoxides, which are widely used, for example, epoxidation of olefins, upon receipt of phenol and carbonyl compounds (acetone, acetaldehyde, etc.)

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of alkylaryl hydroperoxides useful as starting material in production of propylene oxide and alkenylaryl. Process of invention comprises following stages: oxidation of alkylaryl compound to form reaction product containing alkylaryl hydroperoxide; contacting at least part of reaction product with basic aqueous solution; separation of hydrocarbon phase containing alkylaryl hydroperoxide from aqueous phase; containing at least part of above hydrocarbon phase with aqueous solution containing waste water, said aqueous solution containing less than 0.2% alkali metal and/or salt (determined as ratio of metal component to total amount of solution); and separation of hydrocarbon phase from aqueous phase. By bringing at least part of above hydrocarbon phase containing alkylaryl hydroperoxide into interaction with propylene and catalyst, alkylaryl hydroxide and propylene oxide are obtained. At least part of propylene oxide is then separated from alkylaryl hydroxide. Dehydration of at least part of alkylaryl hydroxide results in formation of alkenylaryl.

EFFECT: reduced amount of contaminating by-products in alkylaryl hydroperoxide preparation stage.

8 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining cyclohexyltoluene hydroperoxide, which can serve as source of joint obtaining of cresols and cyclohexanon and as initiator of emulsion polymerisation of unsaturated hydrocarbons. According to claimed method obtaining of cyclohexyltoluene hydroperoxide is carried out by oxidation of cyclohexyltoluene with air oxygen at atmospheric pressure in presence of catalyst N-hydroxyphtalimide at temperature of process 110-140°C, during 2-3 hours until content of cyclohexyltoluene hydroperoxide is 22.2%.

EFFECT: increase of target product formation rate, reduction of process duration and reduction of power consumption for its carrying out.

1 cl, 3 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: present invention refers to the method for preparation of cyclohexylisopropylbenzene hydroperoxide which can be used as initiator of unsaturated hydrocarbons emulsion polymerisation. According to the invention cyclohexylisopropylbenzene hydroperoxide is prepared by oxidation of cyclohexylisopropylbenzene with air oxygen at temperature 100-120°C and atmospheric pressure during 1-3 hrs in the presence of catalyst N-hydroxyphthalimide up to cyclohexylisopropylbenzene hydroperoxide concentration 64%.

EFFECT: enhancing of the cyclohexylisopropylbenzene hydroperoxide formation rate; decrease of the process time and energy consumption.

1 cl, 3 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: present invention refers to the method for preparation of cyclohexyl-o-xylol hydroperoxide which can be used as the source of combined obtaining of xylenols and cyclohexanone and as the initiator of emulsion polymerisation of unsaturated hydrocarbons. According to the invention cyclohexyl-o-xylol hydroperoxide is prepared by oxidation of cyclohexyl-o-xylol with air oxygen at temperature 100-150°C and atmospheric pressure in the presence of catalyst N-hydroxyphthalimide during 1-3 hrs. up to cyclohexyl-o-xylol hydroperoxide concentration 34%.

EFFECT: enhancing of the cyclohexyl-o-xylol hydroperoxide formation rate; decrease of the process time and energy consumption during oxidation process.

1 cl, 2 tbl, 2 ex

FIELD: pharmacology.

SUBSTANCE: invention concerns cyclic hydrocarbons, particularly obtainment of cyclohexyl-p-xylol hydroperoxide, which can serve as source for simultaneous xylenol and cyclohexanol obtainment and as emulsion polymerisation initiator for unsaturated hydrocarbons. Cyclohexyl-p-xylol hydroperoxide is obtained by cyclohexyl-p-xylol oxidation by air oxygen at atmospheric pressure in the presence of N-hydroxyphthalamide catalyst in amount of 0.5-2.5 wt % and process temperature of 110-150°C for 1-3 hours till cyclohexyl-p-xylol hydroperoxide content reaches 9.8%.

EFFECT: reduced duration of oxidation process, reduced power cost.

1 cl, 2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to petrochemical industry and can be used in combined production of styrene and propylene oxide. Ethylbenzene hydroperoxide is obtained in accordance with the invention by oxidising ethylbenzene with atmospheric oxygen in a continuous reactor at atmospheric pressure in the presence of N-hydroxyphthalimide as a catalyst in amount of 0.5-3 wt % and temperature of the process of 125-130°C until achieving content of ethylbenzene hydroperoxide of 19.2%.

EFFECT: increased conversion of ethylbenzene and selectivity of the process.

1 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to synthesis of hydroperoxides of alkylaromatic hydrocarbons which can serve as a source of oxygen-containing organic compounds (phenol, methylphenols, acetone, cyclohexanone etc) and as an initiator of emulsion polymerisation of unsaturated hydrocarbons. The invention discloses a method for synthesis of hydroperoxides of alkylaromatic hydrocarbons through liquid-phase oxidation of these hydrocarbons with atmospheric oxygen at atmospheric pressure, process temperature of 110-130°C, for 1-3 hours in the presence of a 4-methyl-N-hydroxyphthalimide catalyst in amount of 1.0-2.0 wt %.

EFFECT: catalyst prevents use of an initiator and alkaline additives, which considerably simplifies the process, higher conversion of initial alkylaromatic hydrocarbons while preserving high selectivity of the process.

2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for liquid-phase oxidation of ethylbenzene to ethylbenzene hydroperoxide, where concentration of ethylbenzene hydroperoxide is kept below 20 wt % with respect to total weight of the reaction mixture and where styrene and/or a styrene derivative is added to ethylbenzene. Concentration of said styrene and/or styrene derivative can range from 0.01 to 5.0 wt %. The styrene derivative is a styrene derivative in which one or more unsubstituted carbon atoms of the styrene have an alkyl group and/or a halogen atom as a substitute. The invention also relates to a method of producing an alkylene oxide, preferably styrene and propyelene oxide.

EFFECT: improved method.

10 cl, 3 dwg, 1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to obtaining n-cemene hydroperoxide, which can be used for combined production of cresol and acetone. In accordance with invention claimed is method of obtaining n-cymene hydroperoxide by liquid-phase oxidation of n-cymene with air oxygen at atmospheric pressure, temperature of the process 80-110°C, for 1-3 hours, in presence of N-hydroxyphthalimide as catalyst in amount 1-5 wt %, until content of n-cymene hydroperoxyde is 25-28%.

EFFECT: catalyst excludes application of initiator and alkaline additives, which simplifies the process considerably; high rate of n-cymene oxidation is achieved.

1 cl, 3 ex

FIELD: chemistry.

SUBSTANCE: claimed invention relates to method of separating monoalkylbenzene from gas flow, including oxygen and monoalkylbenzene, in which gas flow, including oxygen and monoalkylbenzene, contacts with liquid flow, including naphthalene compound. In addition, claimed invention relates to method of obtaining alkylphenylhydroperoxide, including said monoalkylbenzene separation.

EFFECT: method makes it possible to separate monoalkylbenzene in effective and selective way.

12 cl, 1 ex, 1 tbl, 1 dwg

Up!