Preparation of hydroxyphenyl phosphine oxide mixtures

Patent metadata

Field	Value
Publication number	US-9388340-B2
Application number	US-201313757945-A
Country	US
Kind code	B2
Filing date	Feb 4, 2013
Priority date	Sep 11, 2009
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

A hydroxyphenyl or alkoxyphenyl phosphine oxide composition comprising (i) a first mixture of mono-(hydroxyphenyl) or (alkoxyphenyl)phosphine oxide isomers, (ii) a second mixture of bis-(hydroxyaryl) or (alkoxyphenyl)phosphine oxide isomers, (iii) a third mixture of tris-(hydroxyaryl) or (alkoxyphenyl)phosphine oxide isomers, and optionally iv) a minority amount of non-hydroxy or non-alkoxy tris-phenyl phosphine oxides is provided. Also provided are epoxy resins compositions with excellent flame retardancy and physical properties, which resins comprise the phosphine oxide composition.

First claim

What is claimed:

1. A method of producing a hydroxyphenyl or alkoxyphenyl phosphine oxide composition, the method comprising:
(a) reacting phenol with an alkyl halide having from 1 to 6 carbon atoms in the presence of an alkali metal base to produce a first product mixture comprising an alkoxybenzene and an alkali metal halide;
(b) contacting said first product mixture with an oxidizing agent under conditions such that the alkali metal halide reacts with the alkoxybenzene to produce a first mixture of ortho and para-haloalkoxybenzenes;
(c) reacting said first reaction mixture with magnesium;
(d) adding a benzene halide to the mixture produced in (c) and reacting the benzene halide with magnesium to produce a mixture of alkoxy and non-alkoxy benzene Grignard reagents; and
(e) reacting said mixture of alkoxy and non-alkoxy benzene Grignard reagents with phosphorus oxychloride to produce said alkoxyphenyl phosphine oxide composition comprising:
(i) from about 10 to about 50 wt % of a first mixture of mono-(hydroxyphenyl) or (alkoxyphenyl) phosphine oxide isomers each having the formula (I):

(ii) from about 30 to about 60 wt %2 of a second mixture of bis-(hydroxyphenyl) or (alkoxyphenyl) phosphine oxide isomers each having the formula (II):

(iii) from about 10 to about 50 wt % of a third mixture of tris-(hydroxyphenyl) or (alkoxyphenyl) phosphine oxide isomers each having the formula (III):

iv) 0 to 10 mol % of triphenyl phosphine oxides of the formula IV:

wherein R is an alkyl group containing from 1 to 6 carbon atoms, and each OR group is in the ortho or para position with respect to the bond between the P atom and the associated phenyl group such that, for each mixture (i), (ii) and (iii), the ratio of the number of OR groups in the ortho-position with respect to the bond between the P atom and the associated phenyl group to the number of OR groups in the para-position with respect to the bond between the P atom and the associated phenyl group is from about 20:80 to about 1:99.

2. The method of claim 1 , wherein the alkyl halide comprises methyl bromide.

3. The method of claim 1 , wherein the benzene halide comprises chlorobenzene or bromobenzene.

4. The method of claim 1 , wherein said oxidizing agent comprises hydrogen peroxide.

5. The method of claim 1 and further comprising reacting the product of (e) with an acid to produce said hydroxyphenyl phosphine oxide composition wherein R in each of formulas (I), (II) and (III) is hydrogen.

Assignees

• Timberlake Larry D
• Hanson Mark V
• Siebecker James D
• Chemtura Corp

Inventors

• Timberlake Larry D
• Hanson Mark V
• Siebecker James D

Classifications

• C09K21/12 Primary

  containing phosphorus · CPC title

• C07F9/5325

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title