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Ripening of 1,4-bis (4-phenoxybenzoyl)benzene

a technology of phenoxybenzoyl benzene and 1,4-bis(4-phenoxybenzoyl)benzene, which is applied in the preparation of carbonyl compounds, organic chemistry, chemistry apparatus and processes, etc., to achieve the effect of improving the filterability and facilitating separation of 1,4-bis(4-phenoxybenzoyl)benzen

Inactive Publication Date: 2021-05-27
ARKEMA FRANCE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene with a high purity and yield, which can be carried out at an industrial level. The method involves a ripening step before the solid / liquid separation step, which leads to the formation of larger and easier to separate particles. This results in a better filterability of the product.

Problems solved by technology

Indeed, 1,4-bis(4-phenoxybenzoyl)benzene tends to be present after dissociation of the complex in the form of fine plate-like particles which are inconvenient to separate from the surrounding liquid.

Method used

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  • Ripening of 1,4-bis (4-phenoxybenzoyl)benzene
  • Ripening of 1,4-bis (4-phenoxybenzoyl)benzene
  • Ripening of 1,4-bis (4-phenoxybenzoyl)benzene

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0178]In a 2 L reactor equipped with a mechanical stirrer, with a nitrogen inlet and an outlet going to a scrubber system, 1066 g of ortho-dichlorobenzene, 92.7 g of terephthaloyl chloride and 233 g of diphenyl ether were introduced. After full solubilization, the mixture was set at 35° C. While keeping the temperature at 35° C., 198 g of aluminum trichloride was slowly added over 3 h to the reactant mixture. After completion of aluminum trichloride addition, the mixture was kept agitated at 35° C. during 3 h to finish the reaction. The mixture was then poured into a second reactor containing 830 g of water containing 3% HCl. After completion of this step, the mixture was settled during 3 h so that the aqueous phase could decant and be removed by suction. A second 3% HCl aqueous phase was then added, stirred and then settled during 1 h for decantation. This second acidic aqueous phase was also removed by suction.

[0179]The suspension thus obtained was then heated up to 120° C., and c...

example 2

[0180]A synthesis similar to Example 1 was carried out. After the removal of the second acidic aqueous phase, a sample A of the organic suspension was taken and analyzed by Scanning Electron Microscopy (SEM). The remaining organic suspension was then heated up to 118° C. and then cooled down at 23° C. in 3 h. A second sample B of the suspension was then taken and also analyzed by SEM.

[0181]Micrographs of sample A (2000× magnification) and sample B (1000× magnification) are shown in FIG. 1.

example 3

[0182]80 mL of the organic suspension of 1,4-bis(4-phenoxybenzoyl-benzene) obtained by a process analogous to example 2 was placed in a 100 mL stainless steel pressure filter holder (EMD Millipore©) fitted with a polypropylene filtration cloth (pore size=35 microns).

[0183]Below this filter, a flask was placed on a scale. The system was then closed tightly and nitrogen pressure (typically between 1.1 and 2 bars absolute) was applied to the upper part of the system 30 seconds after introduction of the suspension.

[0184]The amount of filtrate collected in the flask was registered as a function of time. After conversion of the mass data into Volume using the density of the liquid, the filtration time divided by the filtered volume (t / V) was plotted as a function of the filtered volume (V) (see FIG. 2).

[0185]The slope of the graph in the area where the regime is substantially linear was measured and inserted into the Kozeny-Carman equation mentioned above, along with the following values ...

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Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, including: reacting terephthaloyl chloride with diphenyl ether in a reaction solvent and in the presence of a Lewis acid, so as to obtain a product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex; putting the product mixture in contact with a protic solvent, so as to obtain a first phase containing the Lewis acid and a second phase containing 1,4-bis(4-phenoxybenzoyl)benzene; heating at least the second phase up to a maximum temperature, followed by cooling the second phase down to a separation temperature; subjecting at least the second phase to a solid / liquid separation step at the separation temperature, so as to recover solid 1,4-bis(4-phenoxybenzoyl)benzene.

Description

TECHNICAL FIELD[0001]The present application relates to a method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, as well as a method for manufacturing polyether ketone ketone polymers starting from said 1,4-bis(4-phenoxybenzoyl)benzene.TECHNICAL BACKGROUND[0002]Polyether ketone ketone (PEKK) polymers have a number of properties which make them useful for applications involving exposure to high temperature or to high mechanical or chemical stress. They are for instance useful in the aerospace industry, in off-shore drilling and in medical devices.[0003]One known route for manufacturing polyether ketone ketone polymers relies on the use of 1,4-bis(4-phenoxybenzoyl)benzene as a starting material. 1,4-bis(4-phenoxybenzoyl)benzene can be prepared by reacting terephthaloyl chloride and diphenyl ether in the presence of a Lewis acid such as aluminum trichloride.[0004]In document U.S. Pat. No. 4,816,556 (example 2), 1,4-bis(4-phenoxybenzoyl)benzene is prepared by dissolving terephthaloy...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C45/41C07C45/79C08G61/12C08G65/40
CPCC07C45/41C07C45/79C08G2261/3442C08G65/4043C08G2261/45C08G61/127C07C45/46C07C45/81C08L65/00C08G65/4012C07C49/84C07C45/51C07C45/30
Inventor JOUANNEAU, JULIENAMSTUTZ, JÉROMEVINCENT, GUILLAUME
Owner ARKEMA FRANCE SA
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