Eastman Chemical Company

Eastman-kodak Company

John Robert Monnier

Peter James Muehlbauer

Peter J Muehlbauer

Scott Donald Barnicki

Howard M Low

David Martin Hitch

Stephen Neal Falling

Jerome Leonard Stavinoha, Jr

Gerald W Phillips

Stephen A Godleski

George L Oltean

Brian D Roberts

Gary Wayne Hartley

Kimberly Thornton Peters

Jerome L Stavinoha

Shaowo Liang

Robert Sterling Kline

Timothy W Price

Elaine Beatrice Mackenzie

Michael J Hanrahan

Lynda W McGarry

Patricia Lopez-Maldonado

Gustav R Apai, Ii

Stanley John Okrasinski

Timothy Richard Nolen

Laughlin G McCullough

Cris S Moorehouse

Emily Elizabeth Jameson

Disclosed is a process for the preparation of tetrahydro-3-furoic acid by the thermal, non-catalytic oxidation of 3-formyltetrahydrofuran using molecular oxygen.

Preparation of tetrahydro-3-furoic acid

A method for restoring lost activity and selectivity of fresh cesium-promoted catalysts which comprises heating the catalyst at an elevated temperature in the presence of a sweep gas immediately prior to using the catalyst. The catalysts are particularly useful for the selective epoxidation of olefins to their corresponding olefin epoxides. Also described is a method for inhibiting or preventing deactivation of fresh Cs-promoted catalysts.

Reactivation of Cs-promoted, Ag catalysts for the selective epoxidation of butadiene to 3,4-epoxy-1-butene

Disclosed is a process for the preparation of mono-epoxides of certain diolefins wherein a conjugated diolefin, or polyolefin, that contains allylic carbon-hydrogen bonds, is contacted with molecular oxygen in the presence of a modified silver catalyst.

Selective epoxidation of conjugated diolefins

Processes for the selective preparation of 3,4-epoxy-1-butene (EpB) to 1,2-epoxy-butane (butylene oxide-BO) in the presence of the supported catalysts, comprising one or more Group VIII metals deposited on the support materials which have micropores filled with one or more inorganic oxides.

Process for the manufacture of 1,2-epoxybutane

Disclosed is a process for the efficient removal of carbon dioxide from a gas recycle system generated in an epoxidation process wherein 1,3-butadiene is selectively oxidized to 3,4-epoxy-1-butene. Carbon dioxide at low partial pressure is absorbed into an alkanolamine solution from a low pressure recycle gas stream containing high levels of oxygen. Also disclosed is a means for reclaiming the alkanolamine from a solution of a carbon dioxide-alkanolamine salt or adduct formed in the carbon dioxide removal process.

Process for the removal of carbon dioxide from 3,4-epoxy-1-butene process recycle streams

Disclosed are processes for the isoberization of epoxyalkenes to dihydrofurans by contacting an epovyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst. The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.

Isomerization of epoxyalkenes to 2,5-dihydrofurans

Disclosed are certain catalysts and catalyst support materials and processes for the preparation of the catalyst support materials and for the selective hydrogenation of 3,4-epoxy-1-butene (EpB) to 1,2-epoxy-butane (butylene oxide&mdash;BO). The catalyst support materials have micropores filled with one or more inorganic oxides and the supported catalysts comprise one or more Group VIII metals deposited on the support materials. The rhodium-containing supported catalysts are especially useful for the selective hydrogenation of EpB to BO.

Supported catalysts and catalyst support materials and process for the manufacture of 1,2-epoxybutane

Disclosed herein is an improved gas phase process for the selective epoxidation of non-allylic olefins wherein the epoxidation is carried out in the presence of one or more volatile, nitrogen-containing, basic compounds. The presence of a nitrogen-containing basic compound in the olefin-containing reaction gas or vapor suppresses the formation of an organic resinous material which coats the catalyst, thereby decreasing catalyst activity and life and also increases substantially the activity of the epoxidation catalyst. The disclosed process is particularly useful for the continuous manufacture of 3,4-epoxy-1-butene from 1,3-butadiene.

Gas phase process for the epoxidation of non-allylic olefins

The present invention is directed to a process for the selective epoxidation of non-allylic olefins. The process includes the step of contacting a gas mixture comprising a non-allylic olefin, oxygen, and a fluorinated hydrocarbon with a silver epoxidation catalyst at conditions effective to epoxidize the non-allylic olefin. The fluorinated hydrocarbon has a C--F bond dissociation energy of 110 kcal/mole or greater, and sufficiently non-acidic C--H bonds, if present, so as to avoid abstraction of HF from the fluorinated hydrocarbon under reaction conditions.

Use of fluorinated hydrocarbons as reaction media for selective

This invention provides an improved gas phase feed process using heterogeneous catalysis for the selective epoxidation of non-allylic olefins wherein the epoxidation is carried out in the presence of branched-chain alkane or cyclic aliphatic hydrocarbons with high autoignition temperatures and high Research Octane Numbers. The hydrocarbons useful in the present invention possess higher heat capacities as compared to other non-oxidizable materials, e.g., nitrogen, argon, helium, and other straight-chain hydrocarbons, e.g., methane, ethane, and n-butane, as well as smaller flammability (cool flame and explosive) regions than the above-stated hydrocarbons typically used as diluents or ballast gases in olefin epoxidations. The process is particularly useful for the continuous preparation of 3,4-epoxy-1-butene from 1,3-butadiene.

Disclosed is a process for the selective epoxidation of olefins, including diolefins, having more than 2 carbon atoms by the catalytic oxidation of such an olefin in the presence of a supported, fluorine-promoted, silver catalyst.

Epoxidation of butadiene using cesium fluoride promoted silver catalyst

Disclosed is a process for the preparation of 2,3-dihydrofurans from the corresponding isomeric 2,5-dihydrofurans wherein a 2,5-dihydrofuran compound is contacted with a supported, palladium or platinum catalyst in the presence of carbon monoxide to effect the isomerization of 2,5-dihyrofurans to 2,3-dihydrofurans.

Process for the preparation of 2,3-dihydrofurans

Disclosed is a process for the removal of organic chlorides from furan and hydrogenated furans by contacting a crude product stream comprising (i) furan, 2,3-DHF, 2,5-DHF, THF or a mixture thereof and (ii) one or more organic chlorides with a copper-containing scavenger material.

Process for the removal of organic chlorides from furan and hydrogenated

Disclosed is a process for the preparation of 2,3-dihydrofurans from the corresponding isomeric 2,5-dihydrofurans wherein a feed mixture comprising a 2,5-dihydrofuran compound and an aldehyde selected from alkanals containing 2 to 5 carbon atoms and alkenals containing 3 or 4 carbon atoms, an epoxide selected from 1,2-epoxyalkanes containing 2 to 5 carbon atoms and 3,4-epoxy-1-butene, or a mixture of 2 or more of such aldehydes or epoxides and, optionally, carbon monoxide is contacted with a supported, palladium or platinum catalyst to effect the isomerization of 2,5-dihyrofurans to 2,3-dihydrofurans.

Preparation of 2,3-dihydrofurans

Disclosed herein is an improved gas phase process for the selective epoxidation of non-allylic olefins wherein the epoxidation is carried out in the presence of certain inert, paraffin hydrocarbons. Such hydrocarbons possess higher heat capacities as compared to other materials, e.g., nitrogen, argon, methane and helium, typically used as inert diluents in olefin epoxidations. The disclosed process is particularly useful for the continuous manufacture of 3,4-epoxy-1-butene from 1,3-butadiene.

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Kingsport, TN, United States of America

John Robert Monnier