Bayer Corporation

Mobay Corporation

Bayer Aktiengesellschaft

Mobay Chemical Corporation

Miles Inc.

Bayer Materialscience, LLC

Dennis E Jackman

Dietmar B Westphal

Vidyanatha A Prasad

Peter E Newallis

Vijay C Desai

Gary W Combs

Klaus Jelich

Thomas Schmidt

David T Erdman

Daniel M Wasleski

Jeffrey D Macke

Joe J Hanson

John W Brandriff

Thomas F Modrcin

John G Morgan

Cathy L Howerton

Westphal Dietmar B

The present invention provides a method of preparing 4-amino-3-alkylthio-1,2,4-triazine-5-ones of the formula (I):wherein R, R, Rand Rare as defined herein, the method comprising reacting in the presence of a base and under at least one condition selected from the presence of at least one inorganic compound selected from inorganic sulfites and inorganic bisulfites, an inert gas purge, and an alternating inert gas blanket and vacuum, a 4-amino-3-mercapto-1,2,4-triazin-5-one of the formula (II):wherein R, Rand Rare as defined herein, with an alkylating agent of the formula R&#x2014;X, wherein Rand X are as defined herein and collecting the reaction product.

Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones

A process for preparing 3,3-dimethylbutyric acid includes the steps of reacting trimethylpyruvic acid with a first portion of hydrazine to obtain a ketazine, and treating the ketazine with base and a second portion of hydrazine.

Processes for preparing 3.3-dimethylbutyric acid

A process for the production of methyl dithiocarbazinate includes the steps of providing a mixture comprising hydrazine, solvent, carbon disulfide and base; adding methyl bromide to the mixture; cooling the reaction mixture; and recovering methyl dithiocarbazinate. The methyl dithiocarbazinate may be recovered by filtering the reaction mixture to yield a solid methyl dithiocarbazinate retentate and a liquid filtrate; acidifying the filterate with a mineral acid; and adding methyl isobutylketone to the acidified filterate.

Processes for the production of methyl dithiocarbazinate

Methods of purifying 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole include the steps of providing a first 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole composition comprising 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole and organic solvent; performing a first extraction of the 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole composition with a first inorganic acid solution; and performing a second extraction of the 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole composition with a second inorganic acid solution.

Methods of purifying 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole

The present invention relates to an improved process for purifying &agr;-keto acids. In particular, the present invention pertains to the isolation of pivalic acid and other organic impurities from &agr;-keto acids. The process of the invention generally includes (i) the partial acidification of an aqueous solution of a sodium salt of the &agr;-keto acid (a&ldquo;keto salt&rdquo;), (ii) a first solvent extraction of the keto salt solution to remove organic impurities, (iii) further acidification of the keto salt solution, (iv) a second solvent extraction to remove the &agr;-keto acid, and (v) isolation of the &agr;-keto acid from the solvent. In a preferred embodiment, the present invention relates to the preparation of trimethylpyruvic acid (TMPA) of enhanced purity.

Process for purifying &agr;-keto acids

The present invention relates to a process for manufacturing substituted triazolinones, which are intermediates in the preparation of herbicidally active compounds. In particular, this invention relates to the reaction of an isothiocyanate with an alkanol to produce a thionocarbamate intermediate product; alkylation of the intermediate product, reaction of the alkylated intermediate with and alkoxycarbobyl or aryloxycarbonyl hydrazine and reaction of the resultant compound with a base to produce a substituted triazolinone. In this context the terms &ldquo;alkanol&rdquo; and &ldquo;alkylation&rdquo; represent generic terms and thus, include the use of alkanols and alkylating agents having an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, an aryl group or an arylalkyl group.

Process for manufacturing substituted triazolinones

The present invention relates to a dry composition that can be used as a herbicide. The composition contains N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadia zol-2-yl]oxy]acetamide, 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5-(4H)-one, and a pH adjusting agent. The pH adjusting agent is present in an amount such that it constitutes from about 0.1% to about 10% of the composition, and the resulting pH is from about 2.8 to about 5.4. The molar ratio of 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5-(4H)-one to N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadia zol-2-yl]oxy]acetamide in the composition is from about 1:1 to about 1:6.

Stable, dry compositions for use as herbicides

Disclosed herein is a process for preparing high yields of methyl dithiocarbazinate by reacting carbon disulfide, hydrazine and a base in an aqueous medium, in an effective ratio to form a dithiocarbazinate salt followed by methylating the dithiocarbazinate salt with methyl bromide.

Process for preparing methyl dithiocarbazinate by reacting methyl

Disclosed herein is an aqueous process for preparing high yields of methyl dithiocarbazinate by reacting carbon disulfide and hydrazine in an effective ratio, in an aqueous medium to form hydrazinium dithiocarbazinate salt followed by methylating the hydrazinium dithiocarbazinate with methyl bromide.

An epoxide is produced by reacting a sulfonium salt with a ketone in the presence of a low molecular weight alcohol or ether and an alkali metal hydroxide at a temperature of from about 60.degree. to about 90.degree. C. The alkali metal hydroxide is in the solid form. The reaction is generally carried out in the presence of an organic solvent such as toluene. The preferred low molecular weight ether is diethylene glycol. Water is not added to the reaction mixture.

Process for the preparation of an epoxide from ketones using an alcohol

In the oxidation of 2-hydroxy-3,3-dimethyl-butanoic acid in solution in the presence of a ruthenium oxide catalyst to produce 2-oxo-3,3-dimethyl-butanoic acid, the improvement wherein oxidation is effected with oxygen.

Oxygen-ruthenium oxide oxidation of 2-hydroxy-3,3-dimethyl-butanoic acid

The present invention is directed to a process for desulfurizing a compound selected from isothioureas and isothioamides comprising heating the compound to be desulfurized in the presence of a mercaptanol to produce the corresponding desulfurized keto compound.

Process for desulfurization of isothioureas and isothioamides

TCH is produced by a process which does not require expensive measures to remove hydrazine. In this process, hydrazinium dithiocarbazinate is reacted with an amine other than hydrazine or a strong base, optionally in the presence of water. It is preferred that a sulfur suppressing compound also be included in the reaction mixture. The precipitated TCH is removed from the reaction mixture to leave a mother liquor. Hydrazinium-dithiocarbazinate may then be added to the mother liquor. TCH precipitates and may be readily recovered.

Process for the production of thiocarbohydrazide

Thiocarbohydrazide (TCH) is made by reacting carbon disulfide and hydrazine in the presence of a mercaptan at an elevated temperature. The TCH is removed from the reaction mixture, the mother liquor is further treated to form HDTC which is further reacted to form TCH and the mother liquor is recycled. A major advantage of this process is the recyclability of the mother liquor without reduction in TCH yield.

TCH is produced in two stages. In the first stage, carbon disulfide and excess hydrazine are reacted in the presence of a mercaptan and optionally a strong base or an amine other than hydrazine. Carbon disulfide and a strong base (if none was present during the first stage) are then added to the reaction mixture which is further reacted to complete the formation of TCH.

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Prairie Village, KS, United States of America

Dennis E Jackman