Akzo Nobel N.v.

Akzo America Inc.

Stauffer Chemical Company

Imperial Chemical Industries Limited

Supresta LLC

John Tomko

Edward D Weil

Alan M Aaronson

Andrea Leone-Bay

Jeffrey E Telschow

Fred Jaffe

Carl C Greco

Danielle Angrand Bright

Peter E Timony

Sophia Dashevsky

Michael D Broadhurst

Eric W Burkhardt

George C Ciomo

Antoon Ten Kate

Johannes Hermanus Boelee

R Anthony Nunan

Robert L Protzmann

A crude phosphate ester product can be purified by first washing it with chelating agent composition (such as a dilute acidic solution) and then, preferably, water, drying the resulting product, and then treating the resulting product with an acid scavenger, as exemplified by an epoxy-containing compound, such as 3,4-epoxy cyclohexyl methyl-3,4-epoxy cyclohexyl carboxylate.

Process for purification of phosphate esters

Neopentylene 1-phenylvinyl phosphonate

A process for the synthesis of a hydrocarbylvinyl-1-phosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester, which utilizes: (a) the base catalyzed addition (preferably using a nonnucleophilic strong organic base) of a hydrocarbyl phosphite, such as a dialkyl phosphite containing no more than about eight carbon atoms in either of its alkyl groups, to an aldehyde or methyl ketone, such as a phenyl ketone, as exemplified by acetophenone, to form a hydrocarbyl 1-hydroxy-1-hydrocarbylphosphonate, such as a dialkyl 1-hydroxy-1-phenylalkylphosphonate compound; (b) the acid-catalyzed esterification (preferably acetylation) of the compound from (a) with an acid anhydride to form an acylated intermediate; and (c) the removal of carboxylic acid (preferably at a temperature of from about 50&deg; C. to about 215&deg; C. under reduced or atmospheric pressure) from the intermediate from (b) to form the desired hydrocarbylvinylphosphonic acid hydrocarbyl ester, such as a 1-phenylvinylphosphonic acid dialkyl ester.

Synthesis of a hydrocarbylvinylphosphonic acid hydrocarbyl ester

Styrene phosphonic acid (SPA) can be formed the reaction of phosphorous acid with acetophenone, preferably in the presence of a Lewis acid catalyst, to form a hydroxy adduct intermediate thereof which is then reacted with acetic anhydride to form the acyl derivative of the hydroxy adduct, followed by removal of an acetic acid moiety therefrom, preferably in the presence of an acidic catalyst, to form the styrene phosphonic acid product.

Formation of styrene phosphonic acid

A process for forming 1-phenylvinyl-1-phosphonic acid utilizes reacting a mixture of phosphorus trihalide, such as phosphorus trichloride, and acetophenone with water, under conditions in which the water is gradually added to the mixture with cooling to form a reaction mixture, which can be sparged of excess acetophenone with aqueous acid while under vacuum, comprising the 1-phenylvinyl-1-phosphonic acid. This product can be recovered from the reaction mixture by recrystallization from aqueous mineral acid, such as hydrochloric acid.

Formation of 1-phenylvinyl-1-phosphonic acid

Herbicides have the formula ##STR1## in which R is hydrogen, mono- or poly-halo, mono- or di-(C.sub.1 -C.sub.4 alkyl), C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, phenoxy or nitro;

Arylphosphonodiamide compounds and herbicidal compositions thereof

Epoxy resins can be cured by the use of a curing agent formed by the reaction of phosphorus pentoxide with a trialkyl phosphate or phosphonate.

Epoxy resin compositions containing a polyphosphoric/polyphosphonic

Melamine pyrophosphate is made by the direction reaction of pyrophosphoric acid and melamine in an aqueous reaction medium at a temperature of from about 0.degree. C. to about 60.degree. C., preferably from about 0.degree. C. to about 20.degree. C.

Process for manufacture of melamine pyrophosphate

Flame retardant polyester compositions are prepared by incorporating into a polymer from 1-20% by weight of a flame retardant having the structural formula: ##STR1## where Ar is aryl and R and R' are independently alkylene. This class of flame retardant shows high temperature stability and permits incorporation of the flame retardant into the polyester by hot milling at temperatures up to about 390.degree. C.

Thermally stable diphosphonate-type flame retardant additive for plastics

Diaryl sulfones are formed in a two-stage procedure. The first involves the reaction of an aryl sulfonic acid with an aryl reagent containing active hydrogen while by-product water is removed azeotropically. In the second stage, which contains unreacted sulfonic acid, is treated with a sulfone condensing agent and additional aryl reagent to react additional, unreacted aryl sulfonic acid from the first stage.

Preparation of diaryl sulfones

The reaction residue containing diaryl alkylphosphonate resulting from the reaction of triaryl phosphite and alcohol in the presence of a rearrangement catalyst is treated by optionally, and preferably, stripping phenol by-product therefrom, optionally, and then treating the residue with aqueous dilute acid to convert unreacted triaryl phosphite reagent to diaryl phosphite and remove it as an aqueous layer, and then treating the remaining residue with an aqueous base to yield a water phase containing the unwanted diarylphosphite by-product and an organic phase containing the desired diaryl alkylphosphonate, with subsequent removal of the water phase, prior to subsequent distillation of the remaining organic phase residue to remove purified diaryl alkylphosphonate therefrom.

Purification of diaryl alkylphosphonate reaction mixture

Herbicidal compounds having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl; C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms; and Y is benzyl or mono-substituted benzyl wherein the substituent is halogen, amino, nitro or C.sub.1 -C.sub.4 haloalkyl.

Herbicidal esters of 2-bromo-4-methylimidazole-5-carboxylic acid

Herbicidal compounds having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl; and Y is C.sub.3 -C.sub.8 cycloalkylalkyl wherein the alkyl has 1 to 6 carbon atoms; C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl.

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Dobbs Ferry, NY, United States of America

John Tomko