Eastman Chemical Company

Adam Scott Howard

Damon Ray Billodeaux

Daniel Latham Terrill

Brian David McMurray

James Lon Little

Kenny Randolph Parker

Mesfin Ejerssa Janka

Charles Edwan Sumner, Jr

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.

Methods and apparatus for producing a carboxylic acid employing a solvent from esterification of lignocellulosic materials. An acid-containing composition from esterification of lignocellulosic materials can be employed in the oxidation of para-xylene to terephthalic acid. The acid-containing composition can comprise acetic acid, acetic anhydride, and one or more terpenes or terpenes derivatives.

Growing community of inventors

Gray, TN, United States of America

Adam Scott Howard