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Hydroxylation process for aromatic compounds containing a dioxa-heterocyclic system

A technology for the hydroxylation of aromatic compounds, applied in the field of hydroxylation of aromatic compounds, can solve problems such as difficult to operate reagents, expensive raw materials, and environmental impact

Inactive Publication Date: 2005-09-21
BORREGAARD ITALIA SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Indeed, these methods have the following drawbacks: the use of expensive raw materials, which are used when they are not readily available; the use of difficult or dangerous reagents; in any case characterized by serious environmental impacts

Method used

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  • Hydroxylation process for aromatic compounds containing a dioxa-heterocyclic system
  • Hydroxylation process for aromatic compounds containing a dioxa-heterocyclic system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 30 g of TS-1 catalyst, 150 g of methyl isobutyl ketone, 150 g of acetone and 150 g (1.23 moles) of MDB were charged into a reactor equipped with a stirrer, thermometer, condenser and heating / cooling jacket. The resulting suspension was heated to 60°C, maintaining the mass under agitation. Add 84 g of 10% (0.25 mol) H in about 4 hours 2 o 2 , the temperature of the suspension was maintained at 60 °C. The suspension was stirred at 60° C. for 1 hour and the organic phase was subsequently analyzed after separation from the TS-1 catalyst.

[0033] The following results were obtained from GLC analysis of the organic phase: MDB conversion = 15%; selectivity to 5-hydroxy-MDB = 62%.

Embodiment 2

[0035] The same procedure as Example 1 was used, but only 300 g of acetone was added instead of the acetone / methyl isobutyl ketone mixture.

[0036] The following results were obtained from GLC analysis of the organic phase: MDB conversion = 12%; selectivity to 5-hydroxy-MDB = 58%.

Embodiment 3

[0038] Using the same method as Example 1, but dosing 70 g of H in place of the solvent mixture 2 O and 28 g of 30% (0.25 mole) H 2 o 2 .

[0039] The following results were obtained from GLC analysis of the organic phase: MDB conversion = 10%; selectivity to 5-hydroxy-MDB = 25%.

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Abstract

Process for the hydroxylation of aromatic compounds containing a dioxa-heterocyclic system which comprises directly hydroxylating said compounds with hydrogen peroxide in; the presence of a zeolitic catalyst having the general formula: xTi02'(1 -x)Si02 wherein x is i a number ranging from 0.0001 to 0.04.

Description

technical field [0001] The present invention relates to a process for the hydroxylation of aromatic compounds containing heterocyclic ring systems. [0002] More specifically, the present invention relates to a process for the hydroxylation of 1,3-benzodioxoles. [0003] Still more particularly, the present invention relates to the hydroxylation of 1,3-benzodioxole (MDB) to 5-hydroxy-1,3-benzodioxole (5-hydroxy-MDB) Methods. Background technique [0004] Known from the literature are processes for the oxidation of aromatic compounds containing heterocyclic ring systems, such as benzodioxoles, which lead to products such as 5-hydroxy-MDB, which are used in the agricultural, pharmaceutical and cosmetic industries and used as an intermediate in organic synthesis. [0005] For example, British Patent GB2,323,843 describes a process for the preparation of 5-hydroxy-MDB, which involves the use of hydrogen peroxide (H 2 o 2 ) oxidized piperonal. However, since piperonal is a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/50C07B61/00C07D317/64
CPCC07D317/64
Inventor G·安德鲁缇P·潘瑟里V·麦索里O·玛利安尼G·伯格尼尼
Owner BORREGAARD ITALIA SPA
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