Eastman Chemical Company

Brian David McMurray

Damon Ray Billodeaux

Daniel Latham Terrill

Adam Scott Howard

James Lon Little

Robert Lin

Shane Kipley Kirk

Ruairi Seosamh O'Meadhra

A process for making a cyclic compounds such as cyclic acetal or cyclic ketones by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction zone at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a solid acid such as an acidic ion exchange resin, to generate a liquid reaction mixture without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid reaction mixture from the reaction zone as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal compounds from unreacted polyhydroxyl compounds, and optionally recycling back the unreacted polyhydroxyl compounds to the reaction zone. The process produces cyclic acetal compounds in yields of at least 90% with long catalyst life. The process is also suitable to make cyclic ketals from ketone compounds.

Production of cyclic acetals or ketals using solid acid catalysts

A liquid composition containing at least 2 mole % of water, at least 50 mole % of polyhydroxyl compounds, at least 3 mole % of cyclic compounds, and at least 0.01 mole % of a homogeneous acid catalyst. The mole percentages are based on the moles of all liquids in the composition. The liquid composition optionally contains up to 20 mole % of carbonyl compounds, based on the number of moles of the cyclic compounds. The cumulative amount of any other liquid ingredient in the liquid composition does not exceed 10 mole %. The cyclic compounds include cyclic acetals, cyclic ketals, or a combination thereof. The liquid composition is derived from a process for making cyclic compounds by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction vessel at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a homogeneous acid catalyst to generate a liquid phase homogeneous reaction mixture containing the acid catalyst without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid phase homogeneous reaction mixture from the reaction vessel as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal or ketal compounds from unreacted polyhydroxyl compounds.

Production of cyclic acetals or ketals using liquid-phase acid catalysts

A process for making a cyclic compounds such as cyclic acetal or cyclic ketones by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction vessel at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a homogeneous acid catalyst to generate a liquid phase homogeneous reaction mixture containing the acid catalyst without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid phase homogeneous reaction mixture from the reaction vessel as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal compounds from unreacted polyhydroxyl compounds, and optionally recycling back the unreacted polyhydroxyl compounds and/or acid catalyst to the reaction vessel. The process produces cyclic acetal compounds in high yields. The process is also suitable to make cyclic ketals from ketone compounds.

Disclosed is a method for the recovery of crystalline terephthalic acid containing less than about 150 ppmw p-toluic acid by subjecting a solution of terephthalic acid containing minor amounts of p-toluic acid to crystallization in a crystallization zone comprising a plurality of series-connected crystallizers wherein the solution is subjected to rate-controlled evaporative cooling by sequential reduction in pressure and temperature to cause crystallization of terephthalic acid, wherein the pressure of the solution at the end of the crystallization zone is about ambient pressure or less. Solvent which is evaporated from the crystallizers is collected and condensed and the condensed solvent is returned to the crystallization zone at a point subsequent to the crystallizer from which it was obtained.

Growing community of inventors

Hiltons, VA, United States of America

Brian David McMurray