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Improved catalytic process for the preparation of epoxides from alkenes

A technology for epoxides and alkenes, applied in organic chemistry and other directions, which can solve the problems of poor utilization efficiency of oxygen atoms, difficult possibilities, and low value.

Inactive Publication Date: 2007-03-07
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method, despite its absorbency, has the following disadvantages (i) the olefin should be soluble in the alcohol solvent, thus limiting the scope of the process for other alcohol-insoluble olefins; (ii) the carbodiimide used is dicyclohexylcarbodiimide and is Expensive, while the equivalent urea produced at the end of the reaction has a low value; (iii) very inefficient use of oxygen atoms per mole of substrate and requires large volumes (10-fold excess) of oxidant
Therefore, the possibility of scaling up such systems for industrial applications is difficult

Method used

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  • Improved catalytic process for the preparation of epoxides from alkenes

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Experimental program
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Effect test

Embodiment 1

[0042] To styrene (0.1mol), dodecane (0.01mol), urea (2.08mol), sodium bicarbonate (0.03mol) and magnesium sulfate (0.0001mol) in a mechanically stirred solution of 50.0ml of water at 20 ° C 30% aqueous hydrogen peroxide (0.22 mol) was added dropwise over a period of 4 h. After 4.5 h the organic layer of the reaction mixture was separated by a separatory funnel. The aqueous layer was extracted with 4 x 20 mL ether. The combined organic layers were distilled to give styrene oxide. The conversion to epoxide was 99% and the selectivity was 94%.

Embodiment 2

[0044]To a mechanically stirred solution of styrene (0.1mol), dodecane (0.01mol), urea (2.08mol), sodium bicarbonate (0.03mol) in 50.0ml of water was added dropwise 30% of Aqueous hydrogen peroxide (0.22 mol). After 5 h the organic layer of the reaction mixture was separated by a separatory funnel. The aqueous layer was extracted with 4 x 20 mL ether. The combined organic layers were distilled to give styrene oxide. The conversion to epoxide was 99% with a selectivity of 95%.

Embodiment 3

[0046] To styrene (1.0mol), dodecane (0.1mol), urea (20.8mol), sodium bicarbonate (0.3mol) and magnesium sulfate (0.001mol) in a mechanically stirred solution of 500ml of water at 20 ° C for 5h 50% aqueous hydrogen peroxide (2.2 mol) was added dropwise over time. After 5 h the organic layer of the reaction mixture was separated by a separatory funnel. The aqueous layer was extracted with 4 x 20 mL ether. The combined organic layers were distilled to give styrene oxide. The conversion to epoxide was 99% with a selectivity of 94%.

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Abstract

An improved catalytic process for the preparation of epoxides from alkenes using a combination of transition metal salt, an inorganic promoter and an organic additive in absence of solvent or in the presence of a solvent with commercially available hydrogen per oxide has been disclosed. Thus, styrene oxide was prepared at a kilogram scale in 86% isolated yield with purity >95 %.

Description

field of invention [0001] This invention relates to an improved catalytic process for the preparation of epoxides from olefins. More particularly the present invention relates to the formation of olefins, i.e. styrene, indene, cyclohexene, 1,2-dihydronaphthalene, isoprene, alpha-pinene, 1-hexene, 1-octene, in the presence of hydrogen peroxide Use of alkenes and tert-4-octenes, transition metal salts in combination with inorganic bases and organic compounds. These epoxides find application as intermediates in the synthesis of aroma chemicals, drugs, pharmaceuticals and agrochemicals. Background of the invention [0002] Epoxides are highly reactive compounds that can be used in a wide variety of applications due to their reactivity. Epoxidation is a secondary reaction and a highly exothermic reaction with a heat of reaction (approximately 250 kJ / mol); care must therefore be taken at all times to ensure safe handling. Electron donating groups such as alkyl groups on double ...

Claims

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Application Information

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IPC IPC(8): C07D301/12
CPCC07D301/12
Inventor N-U·H·汗S·H·R·阿卜迪R·I·库雷希S·辛格I·阿迈德R·V·贾斯拉P·K·高希
Owner COUNCIL OF SCI & IND RES
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