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    Dehydration and cyclization of α-, β-dihydroxy carbonyl compounds to 2-substituted furan derivatives
    1.
    发明授权
    Dehydration and cyclization of α-, β-dihydroxy carbonyl compounds to 2-substituted furan derivatives 有权

    公开(公告)号：US11578048B2

    公开(公告)日：2023-02-14

    申请号：US17046754

    申请日：2019-04-04

    申请人： Archer Daniels Midland Company

    发明人： James Brazdil ,  Donald Rogness

    IPC分类号： C07D307/68

    摘要： 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═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 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 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 amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids
    2.
    发明授权
    Dehydration and amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids 有权

    公开(公告)号：US11414376B2

    公开(公告)日：2022-08-16

    申请号：US17046730

    申请日：2019-04-02

    申请人： Archer Daniels Midland Company

    发明人： James Brazdil ,  Donald Rogness ,  Chi-Cheng Ma

    IPC分类号： C07C227/08 ,  B01J23/46 ,  B01J21/18 ,  C07C215/08 ,  C07C51/02 ,  C07C51/353 ,  C07C51/373 ,  C07C51/41 ,  C07C51/377

    摘要： Processes are disclosed for the synthesis of an α-amino acid or α-amino acid derivative, 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 (adjacent a carbonyl group of the starting compound) and removal of the β-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 (—NH2) group, for producing the corresponding α-amino acid(s).

    PROCESSES AND CATAYLSTS FOR THE SELECTIVE HYDROGENATION OF COMPOUNDS HAVING CARBONYL CARBON ATOMS
    6.
    发明申请
    PROCESSES AND CATAYLSTS FOR THE SELECTIVE HYDROGENATION OF COMPOUNDS HAVING CARBONYL CARBON ATOMS 有权

    公开(公告)号：US20220064136A1

    公开(公告)日：2022-03-03

    申请号：US17421492

    申请日：2020-01-09

    申请人： Archer Daniels Midland Company

    发明人： James Brazdil ,  Chi-Cheng Ma

    IPC分类号： C07D307/42 ,  B01D3/40 ,  C07C45/64

    摘要： Selective hydrogenation processes are disclosed that can upgrade impure feeds, such as those obtained from biomass and containing a number of small (e.g., 2-6 carbon atom) molecules having aldehyde and/or ketone carbon atoms. For example, whereas glycolaldehyde and its methylated derivative, hydroxyacetone (acetol) are both high value intermediates for certain downstream processing reactions, they are normally recovered in a condensate from pyrolysis of carbohydrates (e.g., aldose-containing sugars) together with glyoxal and its methylated derivative, pyruvaldehyde. The selective hydrogenation of these compounds bearing two carbonyl carbon atoms, without over-hydrogenation to ethylene glycol and propylene glycol, can increase the concentration of the desired intermediates. These beneficial effects of selective hydrogenation may be achieved through the use of a hydrogenation catalyst comprising noble metals such as Ru and Pt.

    PROCESS FOR MAKING TAURINE
    8.
    发明公开
    PROCESS FOR MAKING TAURINE 审中-公开

    公开(公告)号：US20230348370A1

    公开(公告)日：2023-11-02

    申请号：US18002329

    申请日：2021-06-18

    申请人： Archer Daniels Midland Company

    发明人： Chi Cheng Ma ,  James Brazdil ,  Hao Luo

    IPC分类号： C07C309/14

    CPC分类号： C07C309/14

    摘要： A process is described for forming taurine, which comprises reacting monoethanolamine with sulfuric acid to provide an 2-aminoethanol hydrogen sulfate ester product, combining the 2-aminoethanol hydrogen sulfate ester product with at least one of carbon dioxide, a carbonate or bicarbonate and with at least one of a sulfite or bisulfite to form a sulfonation reaction mixture, and heating the sulfonation reaction mixture for a sufficient time to form a taurine product therefrom. The efficiency of the sulfonation step is improved sufficiently to enable a continuous process for making taurine, particularly with at least some concurrent water removal in the first, esterification step to facilitate full conversion of the monoethanolamine to the desired 2-aminoethanol hydrogen sulfate ester intermediate.

    PROCESS FOR SULFONATION OF 2-AMINOETHANOL HYDROGEN SULFATE ESTER TO PRODUCE TAURINE
    9.
    发明公开
    PROCESS FOR SULFONATION OF 2-AMINOETHANOL HYDROGEN SULFATE ESTER TO PRODUCE TAURINE 审中-公开

    公开(公告)号：US20230227403A1

    公开(公告)日：2023-07-20

    申请号：US18000801

    申请日：2021-06-04

    申请人： Archer Daniels Midland Company

    发明人： Chi Cheng Ma ,  James Brazdil ,  Hao Luo

    IPC分类号： C07C303/24 ,  B01D9/00

    CPC分类号： C07C303/24 ,  B01D9/0013

    摘要： A process comprises continuously adding a first stream and a second stream to a sulfonation vessel, wherein the first stream comprises aminoethanol sulfate ester (AES) and the second stream comprises an aqueous solution of sodium sulfite (Na2SO3). The process comprises continuously mixing the AES and the aqueous solution of Na2SO3 in the sulfonation vessel, thus producing a mixture. The process comprises continuously subjecting the mixture to heat in the presence of an inert gas, thus converting the AES to the taurine via sulfonation. In an aspect, the AES has a residence time of no more than four hours in the sulfonation vessel. In an aspect the heating step is conducted at a temperature of at least 115° C. and a pressure of at least 200 psi.