Method of obtaining cyclohexyltoluene hydroperoxide

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

 

The invention relates to a method for producing cumene cyclohexylamine, which can serve as a source of joint production of Cresols and cyclohexanone [Bedkruli, Bigelowiella. Joint production of phenol and acetone. - M.: Costoptimized, 1963; Gdipalloc, Uwisconsin Phenols, - M.: Chemistry, 1974], and also as an initiator emulsion polymerization of unsaturated hydrocarbons [Gaiazova, Waalaikum, Ehitatava. USP, 21, 379 (1952)].

The closest is a method of obtaining cumene cyclohexylamine liquid-phase oxidation of cyclohexylamine oxygen at atmospheric pressure and a temperature of 110-150°C in the presence of initiator (of cumene hydroperoxide), catalyst (octoate cobalt), alkaline additives (soda). In the presence of cumene hydroperoxide at a temperature of 110°C was able to accumulate 5,0% cumene cyclohexylamine for 7 hours. With increasing temperature up to 140°C, the amount of hydroperoxide increases to 12.5% during the same time. Further increase in temperature does not give a positive result, so at 150°C has been able to accumulate 8,9% cumene cyclohexylamine for 7 h, and then begins the process of decomposition. The use of alkaline additives together with the initiator at 130°C results in an increase in the rate of accumulation of hydroperoxide from 0.9 to 2.1 (%/h), similar to OTL is of renders the use of octoate cobalt. The process conditions are presented in tables 1, 2 [Tourkova, Iagubova, Nvidea and other news WU s, 2007, t (4), pp.37-41].

The disadvantages of the above process is the low oxidation rate (not more than 2.3%), long process (5-7 hours), which in some cases leads to the spontaneous decomposition of hydroperoxides. The use of inorganic materials not reused. 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 cyclohexylamine, reducing process time and reduced energy consumption.

This technical problem is solved using the method of producing cumene cyclohexylamine by liquid-phase oxidation of cyclohexylamine oxygen at atmospheric pressure and a temperature of 110-140°C., in the presence of N-hydroxyphthalimide, in the amount of 0.5-2.5 wt.%. In these conditions it is possible to oxidize cyclohexylethyl for 2-3 hours until the content of cumene cyclohexylethyl to 22%. When the selectivity of its founding more than 90%. A characteristic feature of the used catalyst is the simplicity of its receipt and the possibility of repeatedly what about use.

The present invention is illustrated by the following examples.

Example 1

In a glass reactor with a capacity of 10 cm3downloaded 4 cm3cyclohexylamine and to 1.87 wt.% N-hydroxyphthalimide was given oxygen at atmospheric pressure, a temperature of 130 for 3 hours and continuous stirring. The content of hydroperoxide amounted to 22.2%. Oxidat analyzed for the content of hydroperoxide by iodometric method of analysis. Cyclohexylurea was obtained by alkylation of toluene with cyclohexanol.

Example 2

In a glass reactor with a capacity of 10 cm3downloaded 4 cm3cyclohexylamine and to 1.87 wt.% N-hydroxyphthalimide was given oxygen at atmospheric pressure, a temperature of 140 for 2 h and continuous stirring. The content of hydroperoxide amounted to 21.0%. Oxidat analyzed for the content of hydroperoxide by iodometric method of analysis. Cyclohexylurea was obtained by alkylation of toluene with cyclohexanol.

The results of the experiments are shown in table 3.

Obtaining cumene cyclohexylethyl of the proposed method in comparison with the prototype reduced in 2-4 time, energy costs are reduced by 25-30%.

Table 1
The oxidation of the CEC is geksillaurat at a temperature of 110-150°C
no experienceThe amount of cumene hydroperoxide, taken on oxidation, wt.%The reaction temperature, °CThe maximum content of cumene cyclohexylamine, %The time of oxidation, hThe average rate of formation hydroperoxide of cyclohexylamine, (%/h)
11,531105,070,7
21,531206,570,8
31,531307,570,9
41,5314012,571,8
51,531508,971,3
60,711305,970,8
72,7013012,871,8

Table 3
Auto-oxidation of cyclohexylamine in the presence of N-hydroxyphthalimide.
No experienceThe number N of cumene hydroperoxide, taken on oxidation, wt.%The reaction temperature, °CThe maximum content of cumene cyclohexylamine, %The time of oxidation, hThe average rate of formation of cumene cyclohexylethyl, (%/h)
11,8711012,234,1
21,87120 20,236,7
31,8713022,237,4
41,8714021,02the 10.1

The method of obtaining cumene cyclohexylamine liquid-phase oxidation of cyclohexylamine oxygen at atmospheric pressure and a temperature of 110-140°C in the presence of a catalyst, characterized in that the oxidation of cyclohexylamine hold for 2-3 h, and the catalyst used N-hydroxyphthalimide.



 

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