Archer Daniels Midland Company

Donald Rogness

James F Brazdil

James Brazdil

Chi-Cheng Ma

Chi Cheng Ma

Processes are disclosed for the synthesis of a cracked product or an end product, from a starting compound or substrate having a carbonyl functional group (C═O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. According a particular embodiment, an α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group and removal of the β-hydroxy group. The dicarbonyl intermediate is cracked to form the cracked product, in which the first and second carbonyl groups are preserved. Either or both of (i) the cracked product and (ii) a second cracked product generated from cleavage of a carbon-carbon bond of the dicarbonyl intermediate, may be further converted (e.g., by hydrogenation) to one or more end products, which, like the cracked product(s), also having fewer carbon atoms relative to the dicarbonyl intermediate and substrate.

Dehydration and cracking of alpha-, beta-dihydroxy carbonyl compounds to lactic acid and other products

Processes are disclosed for the synthesis of 2-substituted furan derivatives, such as furan dicarboxylic acid (FDCA), from a starting compound or substrate having a carbonyl functional group (C&#x2550;O), with hydroxy-substituted carbon atoms at alpha (&#x3b1;) and beta (&#x3b2;) positions, relative to the carbonyl functional group. According a particular embodiment, an &#x3b1;-, &#x3b2;-dihydroxy carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the &#x3b1;-hydroxy group to a second carbonyl group and removal of the &#x3b2;-hydroxy group. The dicarbonyl intermediate undergoes cyclization and dehydration, to produce the 2-substituted furan derivative. Optionally, a further step of oxidation may be carried out, for example to convert a hydroxymethyl group, as a 5-substituted about the furan ring, to a carboxy group of FDCA.

Dehydration and cyclization of &#x3b1;-, &#x3b2;-dihydroxy carbonyl compounds to 2-substituted furan derivatives

Processes are disclosed for the synthesis of an &#x3b1;-amino acid or &#x3b1;-amino acid derivative, from a starting compound or substrate having a carbonyl functional group (C&#x2550;O), with hydroxy-substituted carbon atoms at alpha (&#x3b1;) and beta (&#x3b2;) positions, relative to the carbonyl functional group. According a particular embodiment, an &#x3b1;-, &#x3b2;-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the &#x3b1;-hydroxy group to a second carbonyl group (adjacent a carbonyl group of the starting compound) and removal of the &#x3b2;-hydroxy group. The dicarbonyl intermediate is optionally cracked to form a second, in this case cracked, dicarbonyl intermediate having fewer carbon atoms relative to the dicarbonyl intermediate but preserving the first and second carbonyl groups. Either or both of the dicarbonyl intermediate and the cracked dicarbonyl intermediate may be aminated to convert the second carbonyl group to an amino (&#x2014;NH) group, for producing the corresponding &#x3b1;-amino acid(s).

Growing community of inventors

Del Mar, CA, United States of America

Donald Rogness