Abstract:
Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R is alkyl, cycloalkyl, or aryl), 5-HMF ethers (5-R′OCH2-furfural where R′ is alkyl, cycloalkyl, or aryl), 5-alkyl furfurals (5-R″-furfural where R″ is alkyl, cycloalkyl, or aryl), mixed feedstocks of 5-HMF and 5-HMF esters, mixed feedstocks of 5-HMF and 5-HMF ethers, and mixed feedstocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA.
Abstract:
A process for purifying a crude furan 2,5-dicarboxylic acid composition (cFDCA) by hydrogenation of a FDCA composition dissolved in a hydrogenation solvent such as water, and hydrogenating under mild conditions, such as at a temperature within a range of 130° C. to 225° C. by contacting the solvated FDCA composition with hydrogen in the presence of a hydrogenation catalyst under a hydrogen partial pressure within a range of 10 psi to 900 psi. A product FDCA composition is produced having a low amount of tetrahydrofuran dicarboxylic acid, a low b*, and a low amount of 5-formyl furan-2-carboxylic acid (FFCA).
Abstract:
Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.
Abstract:
Disclosed is a process for preparing two esters by reacting an aldehyde with an alcohol in the presence of a ruthenium complex compound as a catalyst. The process is particularly useful for preparing ethyl acetate and n-butyl acetate, isobutyl acetate, or 2-ethylhexyl acetate in high yield by coupling acetaldehyde with n-butanol, i-butanol, or 2-ethylhexanol.
Abstract:
Disclosed is a process for preparing two esters by reacting an aldehyde with an alcohol in the presence of a ruthenium complex compound as a catalyst. The process is particularly useful for preparing ethyl acetate and n-butyl acetate, isobutyl acetate, or 2-ethylhexyl acetate in high yield by coupling acetaldehyde with n-butanol, i-butanol, or 2-ethylhexanol.
Abstract:
The invention relates to a process that integrates the oxidation of toluene to benzoic acid with the production of benzoate plasticizers. Toluene is fed to an oxidation vessel in the presence of oxygen and an oxidation catalyst wherein benzoic acid serves as the solvent for the oxidation. The crude benzoic acid produced is not purified and is then reacted with an alcohol in the presence of an esterification catalyst to produce the crude benzoate ester. The oxidation catalyst, esterification catalyst, and other impurities can be mostly removed from the crude benzoate ester in subsequent washing and filtering steps. The benzoate esters produced through this method can be made in fewer steps with both yields and purities above 80%.
Abstract:
Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R is alkyl, cycloalkyl, or aryl), 5-HMF ethers (5-R′OCH2-furfural where R′ is alkyl, cycloalkyl, or aryl), 5-alkyl furfurals (5-R″-furfural where R″ is alkyl, cycloalkyl, or aryl), mixed feedstocks of 5-HMF and 5-HMF esters, mixed feedstocks of 5-HMF and 5-HMF ethers, and mixed feedstocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA.
Abstract:
Disclosed is a process to produce a dry purified carboxylic acid product comprising furan-2,5-dicarboxylic acid (FDCA). The process comprises oxidizing at least one oxidizable compound selected from the following group: 5-(hydroxymethyl)furfural (5-HMF), 5-HMF esters (5-R(CO)OCH2-furfural where R=alkyl, cycloalkyl and aryl), 5-HMF ethers (5-R′OCH2-furfural, where R′=alkyl, cycloalkyl and aryl), 5-alkyl furfurals (5-R″-furfural, where R″=alkyl, cycloalkyl and aryl), mixed feed-stocks of 5-HMF and 5-HMF esters and mixed feed-stocks of 5-HMF and 5-HMF ethers and mixed feed-stocks of 5-HMF and 5-alkyl furfurals to generate a crude carboxylic acid slurry comprising FDCA, cooling a crude carboxylic acid slurry in cooling zone to form a cooled slurry stream. The cooled slurry stream is routed to a solid-liquid separation zone to generate a crude wet cake stream comprising FDCA that is dried in a drying zone to generate a dry carboxylic acid product stream comprising crude FDCA (cFDCA).
Abstract:
A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream.
Abstract:
The present invention relates to a method of making low colored bis(2-ethylhexyl) furan-2,5-dicarboxylate (BEHFD) plasticizer via mild hydrogenation of highly colored BEHFD.