Dow Agrosciences LLC

The Dow Chemical Company

Dowelanco

Dow Global Technolgoies LLC

James William Ringer

Ronald B Leng

Xiaoyong Li

Jossian Oppenheimer

Shawn D Feist

Jimmy J Tai

Reetam Chakrabarti

Jason S Fisk

Siyu Tu

Douglas L Pearson

Mark Muehlfeld

Robert S Bauman

Mark A Nitz

Anne P Wallin

Carmen A Scott

Robert E Hefner, Jr

John N Argyropoulos

Jerry E White

David Craig Molzahn

Dennis A Hucul

John Wesley Hull, Jr

Daniel A Hickman

Jon A Orvik

Richard C Krauss

Karl L Krumel

Fredric L Buchholz

Michael Allen Gonzalez

Dawn L Shiang

Herbert Nathan Praay

Julie L Maurer

Mark Victor Michael Emonds

Thomas A Olmstead

Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling

Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling

An epoxy resin reactive diluent composition comprises an epoxy resin diluent (A) and a resin compound (B), wherein the epoxy resin diluent (A) comprises a cis, trans-1,3- and -1,4-cyclohexanedimethylether moiety; and wherein the resin compound (B) comprises one or more epoxy resins other than the epoxy resin diluent (A). A curable epoxy resin composition comprises the epoxy resin reactive diluent composition and a curing agent and/or curing catalyst therefore. A cured epoxy resin is prepared by curing the curable epoxy resin composition.

Epoxy resin reactive diluent compositions

The present invention is a process for the purification of glyphosate (PMG) comprising:

Purification of n-(phosphonomethyl)glycine

In general the present invention relates to a continuous process for manufacturing (N-phosphonomethyl) glycine, glyphosate, by the catalyzed oxidation of N-phosphonomethyliminodiacetic acid. Glyphosate can be provided in high yield and in a cost efficient process by minimizing the competing side reactions and by-products. The process includes conducting the oxidation reaction and selecting an appropriate catalyst to maximize the rate of the oxidation of N-phosphonomethyliminodiacetic acid while at the same time minimizing the rate of oxidation of glyphosate in the same reaction.

Continuous process for preparing N-phosphonomethyl glycine

Aliphatic primary alcohols, including aliphatic primary alcohols possessing one or more oxygen, nitrogen and/or phosphorus heteroatoms that may be atoms substituting for carbon atoms in the alkyl group or component atoms of substituents on the alkyl group, were converted into salts of carboxylic acids by contacting an alkaline aqueous solution of the primary alcohol with a catalyst comprising cobalt, copper, and at least one of cerium, iron, zinc, and zirconium. Diethanolamine, for example, was converted to sodium iminodiacetate by treatment in an aqueous medium containing sodium hydroxide with a catalyst that was obtained by reducing a mixture of cobalt, copper, and zirconium oxides with hydrogen.

Process for preparing carboxylic acids

N-arylsulfilimine compounds, such as S,S-dimethyl-N-(2,6-dichlorophenyl)sulfilimine, were prepared and found to catalyze the reaction of aromatic sulfonyl chloride compounds, such as 2-chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine, with aromatic amine compounds, such as 2,6-dichloroaniline, to form N-arylarylsulfonamide compounds, such as N-(2,6-dichlorophenyl)-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine-2 -sulfonamide. The aryl moiety of the N-arylsulfilimine catalyst and the aryl moiety of the aromatic amine compound were generally chosen to be identical.

N-arylsulfilimine compounds and their use as catalysts in the

Chloropyrimidine compounds, such as 4,6-dichloro-2-ethoxypyrimidine, were prepared in good yield and good purity from the corresponding hydroxypyrimidine compounds in the absence of organic solvents and with a reduced amount of phosphorus oxychloride by carrying out the reaction in the presence of a trialkylamine compound and phosphorus trichloride. The additions of hydroxypyrimidine compound and trialkylamine compound could be made in segments. The chloropyrimidine compounds produced were recovered in an improved manner by adding chlorine to convert the chlorophosphoric acid by-products and phosphorus trichloride to phosphorus oxychloride, diluting the mixture with additional chloropyrimidine compound and removing the phosphorus oxychloride by distillation, combining the residue with water and a base, distilling the trialkylamine compound from the resulting mixture, and removing the aqueous phase.

Chloropyrimidine process

N-arylsulfilimine compounds, such as S,S-dimethyl-N-(2,6-dichlorophenyl)sulfilimine, were prepared and found to catalyze the reaction of aromatic sulfonyl chloride compounds, such as 2-chlorosulfonyl-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]pyrimidine, with aromatic amine compounds, such as 2,6-dichloroaniline, to form N-arylarylsulfonamide compounds, such as N-(2,6-dichlorophenyl)-7-fluoro-5-ethoxy[1,2,4]triazolo[1,5-c]-pyrimidine- 2-sulfonamide. The aryl moiety of the N-arylsulfilimine catalyst and the aryl moiety of the aromatic amine compound were generally chosen to be identical.

2-Chlorosulfonyl-5-alkoxy[1,2,4]triazolo-[1,5-c]pyrimidine compounds, such as 2-chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine, that are useful for the preparation of 5-alkoxy[1,2,4]triazolo [1,5-c]pyrimidine-2-sulfonamide herbicides, were prepared in an improved manner from 5-alkoxy[1,2,4]triazolo [1,5-c]pyrimidine-2(3H)-thione compounds, such as 5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)-thione, by oxidation with hydrogen peroxide to obtain novel 2,2'-dithiobis(5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine) compounds, such as 2,2'-dithiobis (5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine), and subsequent chloroxidation of these intermediate compounds.

5-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine-2(3H)--thione compounds and

4-Haloquinazolines can be prepared by the halogenation of the corresponding 4-hydroxyquinazolines with a phosphoryl, thionyl or carbonyl halide in the presence of a catalytically effective amount of a N,N-dialkylformamide. The reaction is catalyzed by the addition of soluble organic halide salts.

Process for the preparation of 4-haloquinazolines

Polyethers having improved barrier to oxygen are normally solid, thermoplastic polyethers having backbone repeating units of m-phenylene, p-phenylene, carbonyldiphenylene and/or sulfonyldiphenyl and pendent hydroxyl moieties. Such polyethers are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol A with resorcinol.

Hydroxy-functional polyethers as thermoplastic barrier resins

This invention relates to an improved process for polymerizing vinyl monomers, the improvement comprising using an amine having a functionally effective amount of .alpha.-hydrogens to act as an initiator site and as a crosslinking site for development of a polymer chain. The amine compound acts as a reducing agent in a redox pair initiator system and has a sufficient number of .alpha.-hydrogens available for oxidation to render polymer chain growth from more than two locations on the amine. Through the various available .alpha.-hydrogens and thus polymer chains, the amine compound imparts crosslinking in the polymer and simultaneously acts as an initiator site for polymerization. The crosslinking is therefore produced out from the initiator/crosslinker, instead of by linking existing or growing polymer chains together. The method by which the crosslinking occurs in the present invention is thought to decrease the number of dangling chains present when conventional polymerization methods are used.

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Midland, MI, United States of America

James William Ringer