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Process for producing polyhydric phenol

A technology of polyphenols and group elements, applied in the field of preparation of polyphenols, can solve problems such as DHQ yields that are not specified

Active Publication Date: 2012-05-16
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of DHQ is not described in Non-Patent Document 4

Method used

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  • Process for producing polyhydric phenol
  • Process for producing polyhydric phenol
  • Process for producing polyhydric phenol

Examples

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no. 1 Embodiment approach

[0027] In this embodiment, the steps (a) and (b) of the present invention will be specifically described. That is, in the present embodiment, the second step (b) of the present invention is carried out by dehydration reaction in the absence of an acid catalyst. According to the above method, in the reaction to obtain THB from DOI, the compound represented by the above formula (1) is used as a reaction intermediate, and the dehydration reaction is carried out in the absence of an acid catalyst. Accordingly, the amount of by-products generated in the presence of the acid catalyst can be reduced. Therefore, THB can be produced industrially using chemical methods.

[0028] In the method of this embodiment, it is preferable to dissolve the compound represented by said formula (1) in a reaction solvent, and to perform dehydration reaction, heating to 120 degreeC or more. The reaction temperature is more preferably 120°C to 200°C. Water can be used as a reaction solvent. The conc...

no. 2 Embodiment approach

[0040] In this embodiment, the 3rd step (c) and 4th step (d) of this invention are demonstrated concretely.

[0041] As described above, as a method for industrially producing hydroquinone using a chemical method, the prior art described in the above literature still has room for improvement in terms of yield. For example, in the step of synthesizing hydroquinone from THB, further improvement in yield can be expected.

[0042] Non-Patent Document 1 does not disclose DHQ as an intermediate in the step of producing hydroquinone from THB. In addition, the yield of the reaction to obtain DHQ from THB and the yield of the reaction to obtain hydroquinone from DHQ are not specifically described, respectively.

[0043] In addition, considering the purity, the yield of DHQ in Non-Patent Document 2 is 63%. However, in order to replace the existing petroleum method with a chemical method, further improvement in yield is expected.

[0044]In addition, Non-Patent Document 3 does not spe...

no. 3 Embodiment approach

[0093] This embodiment is a method for preparing hydroquinone using DOI as a starting material. Said method implements the steps represented by (e) and (f) in addition to the steps (a) to (d) of the present invention. Specifically, as described below, it is performed in the order of (a-1), (b-1), (c-2), (d-2), (e), and (f).

[0094]Step (a-1): In the absence of an acid catalyst, the compound represented by the above formula (1), ie (4S, 5R, 6S)-4,5,6-trihydroxy-2-ring, is prepared from DOI by dehydration reaction Hexen-1-one.

[0095] Step (b-1): THB is produced from the compound represented by the above formula (1) obtained in the step represented by (a-1) by dehydration reaction in the absence of an acid catalyst.

[0096] Step (c-2): The alkali metal of DHQ is prepared from THB obtained in the step represented by (b) by a catalytic hydrogenation reaction using a metal catalyst containing an iron group element as a metal component in the presence of a hydroxide of an alkal...

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Abstract

A process for producing a polyhydric phenol, characterized by using the following steps (a) to (d) to produce the phenol: (a) a first step in which (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexcen-1-one is produced from 2-deoxy-scyllo-inosose through dehydration, (b) a second step in which 1,2,4-trihydroxybenzene is produced through dehydration from the (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexen-1-one obtained in the first step, (c) a third step in which 4-hydroxycyclohexane-1,3-dione is produced from the 1,2,4-trihydroxybenzene through catalytic hydrogenation using a metal catalyst, and (d) a fourth step in which the 4-hydroxycyclohexane-1,3-dione is heated to thereby produce hydroquinone.

Description

technical field [0001] The invention relates to a preparation method of polyphenol. Background technique [0002] Hydroquinone is a dihydric phenol having two hydroxyl groups on the benzene ring, and is an important compound as a polymerization inhibitor, a photographic developer, a dye intermediate (pigment, etc.), industrial chemicals, or a raw material for drugs, pesticides, fragrances, and the like. In addition, 1,2,4-trihydroxybenzene is a trihydric phenol having three hydroxyl groups on a benzene ring, and is an important compound as a raw material for industrial chemicals such as oxygen absorbers, pharmaceuticals, and agricultural chemicals. Currently, tens of thousands of tons of the polyphenols are produced within a year using petroleum as a raw material. However, in view of the current state of global environmental pollution, it is imperative to develop new production methods that do not depend on petroleum. [0003] Non-Patent Document 1 discloses that 1,2,4-tri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/07C07C39/10
CPCC07B2200/07C07C45/66C07C45/513C07C37/07C07C2101/16C07C2601/16Y02P20/52C07C39/10C07C39/08C07C49/713B01J23/04C07C46/06
Inventor 北川英男清须纯也斋藤奖林贵臣吉村成利中川亚弥
Owner MITSUI CHEM INC
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