Eastman Chemical Company

Daniel Latham Terrill

Damon Ray Billodeaux

Brian David McMurray

Adam Scott Howard

James Lon Little

Jerome Leonard Stavinoha, Jr

Stephen Neal Falling

Robert Scott Huss

Joseph Robert Zoeller

Robert Thomas Hembre

Thomas James Devon

Norma Lindsey Buchanan

Shaowo Liang

Jonathan Michael Penney

Steven Paul Bellner

David Martin Hitch

Timothy Richard Nolen

Kelley Margaret Moran

Jerry Lynn Miller

Colin Henry Ridyard

Clyde Neil Clubb

Elizabeth Celia Sharkey

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 liquid phase hydrogenolysis of acetal compounds, such as cyclic acetals and cyclic ketals, is disclosed. The acetal compounds are fed to a reaction zone and reacted in the presence of a noble metal catalyst supported on a carbon or silica support to make hydroxy mono-ether compounds in high selectivity, without the necessity of using acidic co-catalysts such as phosphorus containing acids or stabilizers such as hydroquinone.

Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals

Cyclic acetals can be produced in a reactive distillation apparatus by combining a polyhydroxyl compound and an aldehyde. High concentrations of cyclic acetals are removed as liquid products from the column while water is removed as an overhead vapor stream.

Production of cyclic acetals by reactive distillation

Disclosed is a process for producing glycolate ester oligomers. The process comprises reacting ethylene glycol and glycolic acid to produce a stream of glycolate ester oligomers and glycolic acid oligomers while simultaneously removing water. The stream of glycolate ester oligomers and glycolic acid oligomers has a low concentration of water and glycolic acid-ends, and thus is useful in a subsequent hydrogenation reaction to produce ethylene glycol.

Reactive distillation of a carboxylic acid and a glycol

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 process for the preparation of amines by continuously feeding a carboxamide, aqueous alkaline hypohalite, and aqueous alkaline hydroxide to a first reaction zone to form a N-halocarboxamide, measuring the concentration of at least one reaction component in the effluent from the first reaction zone, and using the result of that measurement to control the feed rate of at least one of the feed components of to achieve at least 90% conversion of the carboxamide in the first reaction zone. The effluent from the first reaction zone is fed continuously to a second reaction zone where it further reacts to form an aqueous solution of an amine. The effluent from the second reaction zone may be fed continuously to a distillation column. The process is particularly useful for the preparation of cyclopropylamine.

Continuous process for the preparation of amines

Disclosed is a process for the production of cyclopropylmethyl halides (CPMX) such as cyclopropylmethyl chloride (CPMCl) and cyclopropylmethyl bromide (CPMBr) wherein cyclopropanemethanol (CPMO) is contacted with an aqueous solution of a hydrogen halide (HX) at a temperature in the range of -30.degree. C. to 35.degree. C. Also disclosed is a three-step process wherein CPMO is converted to a CPMX, the CPMX is separated as a liquid organic phase from the aqueous hydrogen halide by decantation and then is subjected to fractional distillation to provide CPMX in high purity. Finally, a process for the co-production of a CPMX and a cyclobutyl halide (CBX) is disclosed.

Process for the production of cyclopropylmethyl halides

Disclosed is a process for the continuous production and recovery of 2,3-dihydrofuran (2,3-DHF) by the isomerization of 2,5-dihydrofuran (2,5-DHF) which contains certain impurities to 2,3-dihydrofuran in yields exceeding 95%. The process utilizes, in order, an isomerization zone containing one or more beds of a supported, palladium or platinum catalyst, a product recovery zone comprising a distillation column, a high boiler removal zone and means for feeding the 2,5-DHF component of the bottoms stream from the product recovery zone to the isomerization zone.

Growing community of inventors

Bristol, TN, United States of America

Daniel Latham Terrill