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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 expensive raw materials, difficult to operate reagents, and environmental impact

Inactive Publication Date: 2006-09-06
BORREGAARD ITALIA SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 to maintain the stirring state of the material. Add 84g of 10% (0.25 mole) H in about 4 hours 2 O 2 , The temperature of the suspension is maintained at 60°C. The suspension was stirred at 60°C for 1 hour, and after the organic phase was separated from the TS-1 catalyst, it was then analyzed.

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

Embodiment 2

[0035] The same method as in 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 the GLC analysis of the organic phase: MDB conversion rate=12%; 5-hydroxy-MDB selectivity=58%.

Embodiment 3

[0038] Using the same method as in Example 1, but adding 70 g of H in place of the solvent mixture in a quantitative manner 2 O and 28g 30% (0.25 mol) H 2 O 2 .

[0039] The following results were obtained from the GLC analysis of the organic phase: MDB conversion rate = 10%; 5-hydroxy-MDB selectivity = 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 method for hydroxylation of aromatic compounds containing heterocyclic ring systems. [0002] More specifically, the present invention relates to a method for the hydroxylation of 1,3-benzodioxole. [0003] More specifically, the present invention relates to the hydroxylation of 1,3-benzodioxol (MDB) to produce 5-hydroxy-1,3-benzodioxol (5-hydroxy-MDB) Methods. Background technique [0004] Known from the literature methods for oxidizing aromatic compounds containing heterocyclic systems (such as benzodioxole), which produce products such as 5-hydroxy-MDB, which are used in agriculture, pharmaceuticals and cosmetics industries And used as an intermediate in organic synthesis. [0005] For example, the British Patent GB2,323,843 describes a method for preparing 5-hydroxy-MDB, which includes the use of hydrogen peroxide (H 2 O 2 ) Piperonal oxide. However, because piperonal is a natural product and needs to be extracted from...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/60C07D317/50C07B61/00C07D317/64
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