Eastman Chemical Company

Eastman-Kodak Company

William Anthony Beavers

Don L Morris

William E Choate

Alexey Victorovitch Ignatchenko

Robert D Culp

Zhufang Liu

Disclosed is a process for the preparation of 3-methyltetrahydrofuran (MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (HOMeTHF) or 3-formyltetrahydrofuran (FTHF) by contacting HOMeTHF or 3-formyltetrahydrofuran with a secondary alcohol in the presence of a hydrous zirconia catalyst.

Process for preparing 3-methyltetrahydrofuran

The invention is a base-modified clay that selectively catalyzes the formation of a glycol monoester from an aldehyde. The base-modified clay comprises a clay having secluded conjugate base sites and exchangeable interstitial cationic spaces. In the base-modified clay, the interstitial hydroxyl groups have been converted to oxide sites, at least one structural hydroxyl group has been converted to an oxide site. The base-modified clay contains sufficient conjugate base cations to balance charge of said oxide groups. Processes for preparing the base-modified clay are described. The invention also provides a process for preparing a glycol monoester. This process includes heating in a reaction vessel an aldehyde and a catalytic amount of the base-modified clay under conditions sufficient to produce a glycol monoester.

Basic clay catalyst for the production of glycol monoester

Disclosed is a process for the preparation of 3-methyltetrahydrofuran (MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (HOMeTHF) by contacting HOMeTHF with hydrogen in the presence of an acidic, supported catalyst comprising a Group VIII metal.

Process for the preparation of 3-methyltetrahydrofuran

The invention is a base-modified clay that selectively catalyzes the formation of a glycol monoester from an aldehyde. The base-modified clay comprises a clay having secluded conjugate base sites and exchangeable interstitial cationic spaces. In the base-modified clay, the interstitial hydroxyl groups have been converted to oxide sites, at least one structural hydroxyl group has been converted to an oxide site. The base-modified clay contains sufficient conjugate base cations to balance the charge of said oxide groups. Processes for preparing the base-modified clay are described. The invention also provides a process for preparing a glycol monoester. This process includes heating in a reaction vessel an aldehyde and a catalytic amount of the base-modified clay under conditions sufficient to produce a glycol monoester.

Basic clay catalyst for the production of pentylglycol monoesters

Disclosed is a process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF) by a plurality of process steps comprising (1) esterifying 3-HOMeTHF to produce a carboxylate ester of 3-HOMeTHF, (2) pyrrolyzing the carboxylate ester to produce 3-methylenetetrahydrofuran (3-methyleneTHF), and (3) hydrogenating the 3-methyleneTHF to produce 3-MeTHF. The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and as a monomer in the manufacture of polymers such as elastomers.

Disclosed is a process for the preparation of 3-alkyltetrahydrofurans by a two-step process wherein 2,3-dihydrofuran is reacted with an acetal to form an intermediate compound which may be converted to a 3-alkyltetrahydrofuran by contacting the intermediate with hydrogen in the presence of a catalytic amount of a Group VIII noble metal or rhenium, water and a strong acid.

Preparation of 3-alkyltetrahydrofurans

Disclosed is a process for the recovery of formyltetrahydrofurans (FTHF's) produced by the rhodium-catalyzed hydroformylation of 2,5-dihydrofuran (2,5-DHF) wherein the FTHF's are recovered as an equilibrium mixture of 2- & 3-FTHF and their hydrates, 2- and 3-�di(hydroxy)methyl!tetrahydrofuran from a hydroformylation product solution comprising a rhodium catalyst, 2- and 3-FTHF and an organic hydroformylation solvent obtained as a liquid product take-off from a hydroformylation process wherein 3-FTHF is produced by the hydro-formylation of 2,5-DHF 3-FTHF is a valuable organic intermediate useful, for example, in the preparation of 3-methyltetrahydrofuran and 3-amino-methyltetrahydorfuran.

Production of aqueous solutions of mixtures of formyltertrahydrofuran

Disclosed is a process for the preparation of 3-methyltetrahydrofuran (3-MeTHF) which comprises contacting 3-formyltetrahydrofuran with hydrogen in the presence of a catalyst system comprising a Group VIII noble metal or rhenium and a strong acid under hydrogenolysis conditions of temperature and pressure to produce 3-MeTHF. The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and, more importantly, as a monomer in the manufacture of polymers such as elastomers.

Preparation of 3-Alkyltetrahydrofurans

Disclosed is a two-step process wherein (1) 2,3-dihydrofuran is reacted with a trialkyl orthoformate in the presence of an acidic catalyst to produce a 2-alkoxy-3-(dialkoxymethyl)tetrahydrofuran intermediate and (2) the intermediate is contacted with hydrogen in the presence of a catalyst system comprising a Group VIII noble metal or rhenium and a strong acid to convert the intermediate to a mixture of 3-methyltetrahydrofuran (3-MeTHF) and 3-(hydroxymethyl)tetrahydrofuran (3-HOMeTHF). The 3-MeTHF produced in accordance with the present invention is useful as an industrial solvent and as a co-monomer in the manufacture of polymers such as elastomers. 3-HOMeTHF may be used as a solvent and in the manufacture of pharmaceutical and agricultural chemicals and acrylate and methacrylate esters for use in preparing polymers such as polyacrylates.

Preparation of 3-methytetra-hydrofuran from 2,3-dihydrofuran

Disclosed is a very economical way to produce vinyl carbonyls such as ethyl vinyl ketone. Disclosed also is a purification process of separating vinyl carbonyls and coreactants. The catalyst and reaction conditions give useful yields of vinyl carbonyls, the thermodynamically unfavorable product along with coreactants that are more thermodynamically favored. Disclosed also is the separation of reactants that takes place at low distillation temperatures and pressures in the presence of antioxidant.

Process for the production and purification of vinyl carbonyls

Process for the production of vinyl carbonyls

A process for producing dimeric unsaturated aldehydes from alpha, beta unsaturated aldehyde is disclosed. This process is conducted by contacting the alpha, beta unsaturated aldehyde with a copper (II) catalyst and a complexing amine catalyst in a medium with a relatively high dielectric constant in substantially anhydrous and aprotic conditions.

Oxidative coupling of alpha, beta unsaturated aldehydes

Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.

Continuous process for the preparation of

Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone. Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.

Growing community of inventors

Longview, TX, United States of America

William Anthony Beavers