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A kind of preparation method of dicumyl hydroperoxide

A technology of dicumyl hydroperoxide and propylbenzene hydroperoxide, which is applied in the direction of the preparation of peroxy compounds, the preparation of organic compounds, chemical instruments and methods, etc., and can solve the problem of decomposition of dicumyl hydroperoxide , Unable to realize continuous production, incompatibility of inorganic alkali solution and other problems, to achieve the effect of simple preparation method, easy continuous production, and promotion of neutralization reaction

Active Publication Date: 2022-08-05
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Patent US4237319A discloses a method for liquid-phase oxidation of m-dicumene, the oxidation reaction is carried out in NaOH or NaOH 2 CO 3 Carry out under the condition of inorganic base, yet this scheme has following problem at least: 1) inorganic base can cause dicumyl hydroperoxide to decompose, reduce the selectivity of DHP; 2) inorganic base solution and raw material are immiscible, and reaction efficiency is low, And the equipment requirements are high; 3) NaOH is highly corrosive
This method does not solve the problems caused by using NaOH as the basic catalyst, and still has the defects of low reaction efficiency and low DHP selectivity, and the operation of changing alkali is complicated, and continuous production cannot be realized
[0008] Patent CN101851187A discloses a method for preparing dicumyl dihydroperoxide with a quaternary ammonium base or a quaternary ammonium salt organic base as a catalyst, but it can be seen from the data of its examples that the reaction time is as high as 20h or more, and the reaction rate Still slower and with lower product yields

Method used

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  • A kind of preparation method of dicumyl hydroperoxide
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] [Preparation Example 1] Preparation of Catalyst A

[0057](1) 0.2 mol of phenylhydroxylamine and 0.06 mol of diketene were dissolved in 400 ml of carbon tetrachloride solvent, stirred, heated to 80° C., refluxed for 10 h, and the reaction solution was separated by silica gel column chromatography to obtain intermediate m, The yield is about 40%.

[0058] Silica gel column chromatography conditions: the solvent was removed by rotary evaporation, and the crude product was separated and purified by column chromatography after concentration (eluent: ethyl acetate: petroleum ether=9:1).

[0059] (2) Dissolve 0.2 mol of intermediate m and 0.4 mol of semicarbazide in 500 ml of ethanol, stir, heat to 80° C., reflux for 8 h, and separate the reaction solution by silica gel column chromatography to obtain intermediate n with a yield of about 20% .

[0060] Silica gel column chromatography conditions: the solvent was removed by rotary evaporation, and the crude product was separ...

Embodiment 2

[0067] Using the intermediate n prepared in Preparation Example 1 as a raw material, prepare catalyst B:

[0068] 0.2 mol of intermediate n, 0.2 mol of propylene, 10 g of ZSM-5 molecular sieve catalyst, 200 ml of methanol solvent, 100° C. and 1 MPa pressure were stirred and reacted for 2 h, and catalyst B was obtained by separation.

[0069] The NMR analysis data are as follows:

[0070] 1 H NMR (500MHz, CDCL3): δ 7.77–7.38 (m, 2H), 7.28–6.90 (m, 2H), 4.92 (s, 2H), 3.23 (s, 1H), 2.87 (m, 1H), 1.20 (d, J=12.8Hz, 6H).

[0071] 13 C NMR: (125MHz, CDCL3) δ162.27, 147.64, 147.35, 126.27, 121.68, 33.96, 23.38.

[0072] The structure of analytical catalyst B is represented as follows:

[0073]

Embodiment 3

[0075] Using the intermediate n prepared in Preparation Example 1 as a raw material, prepare catalyst C:

[0076] 0.2 mol of intermediate n, 0.2 mol of 1-heptene, 10 g of ZSM-5 molecular sieve catalyst, 200 ml of methanol solvent, 130° C. and 0.3 MPa pressure were stirred and reacted for 2 h, and catalyst C was obtained by separation.

[0077] The NMR analysis data are as follows:

[0078] 1 H NMR (500MHz, CDCL3): δ7.61(s,1H), 7.58–7.48(m,2H), 7.11–7.01(m,2H), 5.68(s,2H), 2.67–2.50(m,1H) ,1.68–1.52(m,2H),1.34–1.20(m,6H),1.18–1.10(d,J=13.0Hz,3H),0.93–0.85(m,3H).

[0079] 13 C NMR (125MHz, CDCL3): δ162.27, 146.02, 144.52, 126.42, 121.88, 39.67, 36.08, 31.59, 27.65, 23.16, 20.62, 14.00.

[0080] The structure of analytical catalyst C is expressed as follows:

[0081]

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Abstract

The invention discloses a preparation method of dicumyl benzene hydroperoxide, which comprises the following steps: a structural compound represented by the following formula is used as a catalyst, and dicumyl benzene is contacted and reacted with an oxygen-containing gas to generate dicumyl benzene-containing hydrogen Peroxide reaction solution. The method has the advantages of simple operation, fast reaction rate, high reaction yield, good safety and excellent industrial application prospect.

Description

technical field [0001] The invention relates to a preparation method, in particular to a preparation method of dicumyl hydroperoxide. Background technique [0002] Diisopropylbenzene hydroperoxide is a mixed peroxide obtained from the oxidation of diisopropylbenzene. It can be used as a free radical reaction initiator, an oxidant, an intermediate in organic synthesis, etc. It has been industrially applied to the production of α , α'-dihydroxy-diisopropylbenzene (DC for short), diphenol and acetone, etc. [0003] The mainstream production route of dicumyl benzene hydroperoxide is: dicumyl benzene is oxidized to prepare dicumyl benzene hydroperoxide through oxidant (such as oxygen) under alkaline environment, and the reaction expression is as follows: [0004] [0005] Among them, DHP, MHP, HHP are all effective products dicumyl hydroperoxide. [0006] Patent US4237319A discloses a method for liquid phase oxidation of m-dicumene, and the oxidation reaction is performed in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C409/12C07C409/10C07C407/00B01J31/02
CPCC07C407/00B01J31/0249B01J2231/70C07C409/12C07C409/10
Inventor 刘振峰冯民昌刘释水李俊平边新建马德森
Owner WANHUA CHEM GRP CO LTD
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