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Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom

Inactive Publication Date: 2005-07-28
BORIACK CLINTON J +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] Another aspect of the present invention is directed to a process for manufacturing an α-halohydrin intermediate of at least one or more phenols using an in situ halide substitution-deesterification process to convert an α-hydroxy ester derivative of at least one or more phenols to the α-halohydrin intermediate. The process is preferably carried out under anhydrous conditions with an anhydrous hydrogen halide such as hydrogen chloride, hydrogen bromide, or hydrogen iodide, as a reactant; and optionally, the process is carried out in the presence of a solvent.
[0014] Yet another aspect of the present invention is directed to an alternative, non-epichlorohydrin process for

Problems solved by technology

Additionally, a large amount of water is used when converting allyl chloride into an α-chlorohydrin intermediate, and this water must eventually also be treated as waste.
In addition, epoxy resins made from ECH by either of the previously described two-step or single-step processes, may have a high organic chloride content which may be deemed as undesirable in some applications, for example, in electronic applications.
Glycidol is known to be a highly toxic and thermally unstable material tending to explosively self-polymerize.
At low temperatures, such as 70° C., glycidol is unstable and the loss of epoxide content of glycidol is significant.
Glycidol self-polymerization diminishes glycidol selectivity and product yield in its reactions, and the glycidol self-polymerization products complicate separation and purification of the desired reaction product.

Method used

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  • Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom
  • Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom
  • Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom

Examples

Experimental program
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Effect test

example 1

A. Epoxidation of Allyl Acetate to Glycidyl Acetate

experiment a1

[0216] In this part of Example 1, a 100-mL, four-necked, glass reactor equipped with a cooling condenser, a thermometer, a magnetic stirrer, a nitrogen inlet and a heating lamp with a thermocontroller was employed. To the reactor were added 20 g (0.2 mole) of allyl acetate (commercially available from Aldrich Chemical Co.), 20 mL of methylene chloride, 0.50 g (1.0 mole percent based on the amount of allyl acetate) of methyltrioxorhenium (MTO) and 0.76 g (15 mole percent based on the amount of allyl acetate) of pyrazole. The resultant reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 5 minutes. Then 38 g (2 molar equivalents based on the amount of allyl acetate) of aqueous 35 percent hydrogen peroxide solution as an oxidant was added into the reactor at ambient temperature. A slight exothermic reaction occurred, and the temperature of the reaction mixture reached 30° C. The reaction was carried out at 25° C. for about 12 hours and then at 30° C. for ...

experiment a2

[0219] In this part of Example 1, a 250-mL, four-necked, glass reactor equipped with a cooling condenser, a thermometer, a magnetic stirrer, a nitrogen inlet and an ice-water cooling bath was employed. To the reactor were added 50 cc of acetonitrile and a mixture containing 0.08 g (0.45 mmole) of MnSO4·H2O and 2 g of water. The resultant reaction mixture was thoroughly mixed and 0.12 g of N,N′,N″-trimethyl-1,3,9-triazacyclononane (TMTACN, 0.69 mmole mole) was added to the reaction mixture, followed by the addition of a mixture containing 0.042 g (0.45 mmole) of oxalic acid, 0.060 g (0.45 mmole) of sodium oxalate and 2 g of water.

[0220] After thoroughly mixing the resultant reaction mixture, 15 g of allyl acetate (0.15 mole) was added into the reaction mixture. The reactor contents were cooled to 10° C., and 28.5 g (0.3 mole) of aqueous 35 percent hydrogen peroxide solution was added to the reaction mixture over about 30 minutes. Upon addition of the first portion of hydrogen peroxi...

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Abstract

A process for manufacturing an α-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an α-halohydrin intermediate produced from an in situ halide substitution-deesterification of an α-hydroxy ester derivative which has been obtained by the coupling reaction of a phenol or a mixture of phenols and a glycidyl ester optionally in the presence of a catalyst.

Description

BACKGROUND OF THE INVENTION [0001] The present invention relates to a process for manufacturing an α-halohydrin ester derivative of at least one or more phenols and converting such α-halohydrin ester derivative to an epoxy resin. [0002] More specifically, the present invention relates to a process for manufacturing an α-halohydrin derivative at at least one or more phenols, converting such α-halohydrin ester derivative to an α-halohydrin intermediate of at least one or more phenols and utilizing such α-halohydrin intermediate of the at least one or more phenols to make an epoxy resin. For example, the present invention is useful for manufacturing bisphenol A (bis A) epoxy resin. α-Halohydrins are made, as reactive intermediates, via several processes which are well known to those skilled in the art. Generally, the intermediate α-halohydrins are subsequently converted into epoxides. In one widely practiced process, α-halohydrins are made by reacting low molecular weight olefin-contai...

Claims

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Application Information

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IPC IPC(8): C08G59/00C08G59/02C08G59/04
CPCC08G59/00C08G59/04C08G59/02
Inventor BORIACK, CLINTON J.LIAO, ZENG K.
Owner BORIACK CLINTON J