Eastman Chemical Company

Kenneth Wayne Hampton, Jr

Damon Ray Billodeaux

Scott Donald Barnicki

Jeffrey Scott Kanel

Chad Johnson

Eugene H Brown

Thomas Allen Puckette

Charles Edwan Sumner, Jr

Gerald Charles Tustin

Robert Thomas Hembre

Guy R Steinmetz

Zhufang Liu

Xianchun Wu

Raymond Prescott Cottle

Robert Jacks Sharpe

Venkata Bharat Ram Boppana

Eduardo Gallas Cervo

Melissa Page Steffey

Venkata Bharat Boppana

Thomas K Brown

Amy K Paris

Kevin S Howe

Manik Lal Saha

Magnus Alexander Pauly

Guy Ralph Steinmetz

Chad A Johnson

Processes are disclosed for preparing carboxylic acids from organic esters, the processes comprising contacting an ester with water in the presence of an acid catalyst and a homogenizing solvent at conditions effective to form a carboxylic acid. The homogenizing solvent is present in an amount sufficient to form a single-phase reaction mixture comprising the ester, water, and homogenizing solvent. The homogenizing solvent may be selected from acetonitrile, dimethyl sulfoxide, and 1,4-dioxane.

Processes for producing carboxylic acids

An efficient process useful for the self-condensation of aliphatic aldehydes is provided, catalyzed by dialkylammonium carboxylate salts. In particular, the invention provides a facile method for the preparation of 2-ethyl hexenal via the self-condensation of butyraldehyde using various dialkylammonium carboxylates, e.g., diisopropylammonium acetate or dimethylammonium acetate, as catalyst. Additionally, residual nitrogen arising from the catalyst can be reduced to −100 ppm levels in the product via a simple washing procedure. The invention provides a process for preparing alkenals under conditions which limit the formation of undesired impurities and high-boiling oligomeric substances.

Self-condensation of aldehydes

The oxidation of isobutyraldehyde produces isobutyric acid and byproducts, such as isopropyl formate. A process of reducing the isopropyl formate byproduct and other byproducts in the oxidation of isobutyraldehyde is described. The process uses a carbonyl compound, such as acetone, to reduce byproduct levels in the resulting product. Process for use of static mixers in oxidation reactions of aldehydes are also provided.

Aldehyde oxidation processes

Disclosed is a method of making and using a titania supported palladium catalyst for the single step synthesis of 2-ethylhexanal from a feed of n-butyraldehyde. This titania supported palladium catalyst demonstrates high n-butyraldehyde conversion but also produces 2-ethylhexanal in an appreciable yield with maintained activity between runs. This method provides a single step synthesis of 2-ethylhexanal from n-butyraldehyde with a catalyst that can be regenerated that provides cleaner downstream separations relative to the traditional caustic route.

Single step conversion of N-butyraldehyde to 2-ethylhexanal

There is provided is a method for making a higher purity alcohol comprising: a) contacting an impure alcohol composition comprising: (i) an alcohol compound; and (ii) from about 50 ppm to about 5 weight percent, based on the weight of the impure alcohol composition, of at least one hydrogenable contaminant having an unsaturated bond, with hydrogen in a hydrogenation reactor and in the presence of a hydrogenation catalyst to produce a reaction mixture comprising the alcohol compound and a hydrogenated contaminant product wherein at least 10 mole % of the at least one hydrogenable contaminant in the reaction mixture is converted; and b) separating the alcohol compound from at least a portion of the reaction mixture to produce an enriched alcohol composition having a lower concentration of the hydrogenated contaminant product. There is also provided an alcohol composition having less than about 500 ppm of at least one hydrogenable contaminant.

Method for making a high purity alcohol

The oxidation of isobutyraldehyde produces isobutyric acid and byproducts, such as isopropyl formate. A method of reducing the isopropyl formate byproduct in the oxidation of isobutyraldehyde is described. The method uses a co-solvent, such as acetone, to the isobutyraldehyde feed to increase both the selectivity of the reaction to isobutyric acid and the production rate of isobutyric acid so that the isopropyl formate byproduct is significantly reduced.

Reduction of ester formation in isobutyraldehyde oxidation

An improved process for preparing hydroxy aldehydes, such as hydroxypivaldehyde, is provided. Specifically, the process employs an alkaline additive for separating by-product amine salts from a hydroxy aldehyde and other reaction products formed in the process of preparing a hydroxy aldehyde using an amine catalyst.

Preparation of hydroxy aldehydes

Disclosed is a process for the extractive recovery of a homogeneous ruthenium catalyst from the reaction product of the hydrogenation of glycolic acid, glycolate esters, and/or glycolic acid oligomers with an extractant comprising a hydrophobic solvent and an optional hydrophilic solvent. The ruthenium catalyst, which can include 1,1,1-tris(diaryl- or dialkylphosphinomethyl)alkane ligands, can be recovered from the hydrophobic extract phase by back extraction with a hydrophilic solvent and recycled to a process for the preparation of ethylene glycol by the hydrogenation of glycolic acid and glycolic acid derivatives.

Method for recovery and recycle of ruthenium homogeneous catalysts

Methods for recovery and recycle of ruthenium homogenous catalysts

A process for producing polyols (such as neopentyl glycol) is disclosed which comprises reacting formaldehyde and another aldehyde in the presence of a trialkylamine catalyst and a base promoter to form an Aldol condensation reaction product. The base promoter improves removal of nitrogen containing salts prior to hydrogenation of the hydroxy aldehyde to produce the polyol. The improved process also reduces trialkylamine catalyst usage, improves trialkylamine catalyst recovery, and reduces nitrogen-containing salts prior to hydrogenation.

Process for producing polyols

Disclosed is a process for the preparation of 1,2-glycols by hydrogenation of 1,2-dioxygenated organic compounds in the presence of a catalyst composition comprising a ruthenium compound, a trivalent phosphorus compound selected from 1,1,1-tris(diarylphosphinomethyl)alkyl or substituted alkyl, and a promoter selected from Lewis acids, protic acids having an ionization constant (K) of 5&#xd7;10or greater, and onium salts. The process is useful for the hydrogenation of glycolic acid or derivatives thereof to ethylene glycol.

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Gilmer, TX, United States of America

Kenneth Wayne Hampton, Jr