Process for conversion of phenol to hydroquinone and quinones

a technology of hydroquinone and phenol, which is applied in the direction of catalyst activation/preparation, group 3/13 element organic compounds, physical/chemical process catalysts, etc., can solve the problems of increasing the cost of the process, and reducing the efficiency of the process

Inactive Publication Date: 2005-03-31
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The main objective of the present investigation is to provide a new heterogeneous catalytic process for the oxidation of phenol to hydroquinone, which avoids the drawbacks as detailed above.
It is another object of the invention to provide a process for the oxidation of phenols, which is environmentally efficient and economical, and avoids the formation of tar by-products.
It is a further object of the invention to provide a simple process for the oxidation of phenol, without affecting the selectivity and activity in the process.
In another embodiment, a variety of phenols (where R=H, Me, Cl, Br, I, t-Bu, etc.) can be converted to the corresponding quinones in excellent yield and selectivity.

Problems solved by technology

Oxidation of phenol with Y-zeolites containing transition metals such as Cu, Mn, Fe, Cr, etc. makes use of expensive cyclic ligands for effective conversion of phenol to hydroquinone; separation of these cyclic ligands is also tedious.
Use of sulfonic acid and peroxy carboxylic acids often results in mixture of catechol and hydroquinone with poor selectivity, which makes the separation of products more difficult.
Use of benzaldehye adds to the cost of the process and also generates benzoic acid as the side product.
This leads to an additional raw material consumption and separation issue.
Use of Cu with 2,2′bipyridine or phenanthroline ligands in CH3CN is a homogeneous process in which catalyst separation from the product is tedious and the catalyst cannot be reused.

Method used

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  • Process for conversion of phenol to hydroquinone and quinones
  • Process for conversion of phenol to hydroquinone and quinones
  • Process for conversion of phenol to hydroquinone and quinones

Examples

Experimental program
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Effect test

example 1

Preparation of 1,4-hydroquinone

A mixture of phenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20% w / w) in acetic acid (5 ml) was heated with stirring at 50-60° C. under inert atmosphere. To this reaction mixture was added aq. 10% H2O2 (20 mmol) drop wise over 15 min. and heated for 2 h. After this, water (5 ml) was added and the reaction mixture was heated to reflux for 8 h. The catalyst was recovered by simple filtration and 1,4-hydroquinone formed (20%) was separated by chromatographic purification.

example 2

Preparation of 1,4-hydroquinone

A mixture of phenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20% w / w) in acetic acid (5 ml) was heated with stirring at 50-60° C. under inert atmosphere. To this reaction mixture was added aq. 50% H2O2 (20 mmol) drop wise over 15 min. and heated for 1 h. After this, water (5 ml) was added and the reaction mixture was heated to reflux for 7 h. The catalyst was recovered by simple filtration and 1,4-hydroquinone formed (61%) was separated by chromatographic purification.

example 3

Preparation of 1,4-hydroquinone

A mixture of phenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20% w / w) in acetic acid (5 ml) was heated with stirring at 50-60° C. under inert atmosphere. To this reaction mixture was added aq. 30% H2O2 (20 mmol) drop wise over 15 min. and heated for 1 h. After this, water (5 ml) was added and the reaction mixture was heated to reflux for 6 h. The catalyst was recovered by simple filtration and 1,4-hydroquinone formed (60%) was separated by chromatographic purification.

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Abstract

The present invention relates to a process for the conversion of phenol to hydroquinone and quinones. More particularly this invention relates to a process for the oxidation of phenol to a mixture of 1,4-benzoquinone and hydroquinone using an oxidant in the presence of titanium superoxide as a reusable catalyst in a liquid phase condition.

Description

FIELD OF THE INVENTION The present invention relates to a process for the conversion of phenol to hydroquinone and quinones. More particularly this invention relates to a process for the oxidation of phenol to a mixture of 1,4-benzoquinone and hydroquinone using aq. hydrogen peroxide as the oxidant in the presence of titanium superoxide as a reusable catalyst in a liquid phase condition. BACKGROUND OF THE INVENTION Several processes are described in the art for the hydroxylation of phenol to hydroquinone and catechol using hydrogen peroxide as the oxidant and transition metals as catalysts. In the prior art, catalytic conversion of phenol to catechol and hydroquinone has been achieved by the following procedures. European patent 0266825 (1988), 0265018; U.S. Pat. No. 4,396,783 (1983), U.S. Pat. No. 5,493,061 (1996); UK patent No. 2116974; Japanese patent No. JP 10291948, JP 2001158756; Chinese patent CN 1268502, CN 1129607 all disclose various methods for the use of titanium sili...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B01J21/06B01J37/03C07C37/60C07C39/08C07C46/06
CPCB01J21/063B01J37/033C07C37/60C07C46/06C07C50/24C07C50/04C07C50/02C07C39/08
Inventor DEWKAR, GAJANAN KUNDALITHAKUR, VINAY VIJAYRAJPARDHY, SANJEEVANI AMRITSUDALAI, ARUMUGAMDEVOTTA, SUKUMAR
Owner COUNCIL OF SCI & IND RES
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