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Process for producing 3,3',5,5'-tetraalkyl-4,4'-biphenol

A manufacturing method, tetraalkyl technology, applied in 3 fields, can solve problems such as prolonged reaction time, achieve the effect of suppressing the increase of reaction time, suppressing the decline of conversion rate, and reducing the amount of waste

Active Publication Date: 2007-09-26
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present inventors tried to distill and recover the azeotropic mixture containing the above-mentioned water and dialkylphenol and reuse it directly as a part of the raw material, but encountered a predetermined conversion in the oxidative dimerization reaction during repeated recovery and reuse. The rate of reaction time is gradually extended to the problem

Method used

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  • Process for producing 3,3',5,5'-tetraalkyl-4,4'-biphenol
  • Process for producing 3,3',5,5'-tetraalkyl-4,4'-biphenol
  • Process for producing 3,3',5,5'-tetraalkyl-4,4'-biphenol

Examples

Experimental program
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Embodiment

[0076] Hereinafter, although an Example demonstrates this invention, this invention is not limited to the following Example. In addition, the analysis methods of 2,6-xylenol and 3-methylsalicylaldehyde (MSA) in Examples and Comparative Examples are as follows.

[0077] For quantitative analysis of 2,6-xylenol and MSA, a capillary column ("CBP-5" manufactured by J&W Co., Ltd.) packed with phenylmethylpolysiloxane with a crosslinking degree of 5% was used as a column, and as a detector , performed by gas chromatography ("GC-14B" manufactured by Shimadzu Corporation) using a hydrogen flame ionization detector. 20 g of the test material was dissolved in 20 ml of dimethylformamide to prepare and measure the test material, and phenol was used as an internal standard substance. Quantification of 2,6-xylenol by the internal standard method, and for MSA, the purity of 2,6-xylenol quantified by the internal standard method and the areas of the gas chromatograms of 2,6-xylenol and MSA ...

reference example 1

[0079] In a 1L separable flask with a baffle, add 183g of 2,6-xylenol containing a specified amount of 3-methyl salicylaldehyde, 20g of borax, 0.6g of sodium lauryl sulfate, 600g of water, Copper acetate (monohydrate) 6mg (0.03mmol), stirring while heating. Oxygen introduction was started when the content reached 70°C. In the state of keeping the reaction temperature at 70°C and the oxygen partial pressure at 0.01MPaG, keep stirring, monitor the oxygen absorption, and adjust the reaction speed. The results are shown in Table 1 below.

[0080] experiment

Embodiment 1

[0082] 100 parts by weight of a distillation recovery liquid containing 11 weight % of 2,6-xylenol, 89 parts by weight of water, and a small amount of MSA are supplied from the recovery raw material tank to a stainless steel reactor. ), continue to add new raw material 2, 64 parts by weight of 6-xylenol and 42 parts by weight of new water, heat up while stirring. The concentration of MSA contained in 2,6-xylenol (75 parts by weight) in the added reaction liquid was 0.07 parts by weight. When the temperature of the contents reached 60° C., 3.3 parts by weight of borax, 0.13 parts by weight of sodium lauryl sulfate, and 0.004 parts by weight of copper acetate (monohydrate) were added, and the temperature was raised while stirring. When the temperature of the contents reached 70°C, the introduction of oxygen was started. Stirring was continued with the reaction temperature kept at 70°C, and when the oxygen consumption reached the amount of oxidative dimerization of about 85% by ...

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Abstract

An industrially advantageous process for producing a tetraalkylbiphenol (TABP) in which an unreacted dialkylphenol (DAP) can be repeatedly recovered and reused. The process comprises: a step (A) in which a DAP is oxidatively dimerized with an oxygenic gas in the presence of a water solvent and a metallic catalyst to obtain an aqueous slurry which comprises a liquid reaction mixture containing the unreacted DAP, the metallic catalyst, and an aromatic aldehyde as an impurity and a TABP dispersed in the mixture; and a step (B) in which the TABP is separated from the resultant aqueous slurry by solid-liquid separation. In the process, the aqueous slurry and / or the aqueous liquid reaction mixture recovered in the step (B) is distilled to recover an azeotropic mixture comprising water and the unreacted DAP, and part of the recovered fraction containing the aromatic aldehyde is supplied to the oxidative dimerization to regulate the amount of the aromatic aldehyde contained in a feed reaction mixture so as to be up to 60 times by mole the amount of the metallic catalyst therein.

Description

technical field [0001] The present invention relates to a process for the production of 3,3',5,5'-tetraalkyl-4,4'-bisphenols, in particular, to the industrially advantageous use of oxidative dimerization of 2,6-dialkylphenols Process for the manufacture of 3,3',5,5'-tetraalkyl-4,4'-bisphenols. Hereinafter, 3,3',5,5'-tetraalkyl-4,4'-bisphenol may also be simply referred to as "tetraalkylbisphenol". Background technique [0002] Tetraalkylbisphenols are useful compounds as raw materials for epoxy resins, polyester resins, polycarbonate resins, etc., or as raw materials for stabilizers and plasticizers for petroleum products. Among them, tetraalkylbisphenols whose alkyl groups are methyl groups are useful as raw materials for epoxy resins in the electrical and electronic fields. [0003] As a method for synthesizing tetraalkylbisphenols, it is known to oxidatively dimerize 2,6-dialkylphenols (hereinafter sometimes simply referred to as "dialkylphenols") in an aqueous solvent ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/11C07C39/15
CPCC07C39/15C07C37/11C07C37/00C07C39/00
Inventor 下山典克村井浩也泽田善秋
Owner MITSUBISHI RAYON CO LTD