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    PROCESSES AND CATAYLSTS FOR THE SELECTIVE HYDROGENATION OF COMPOUNDS HAVING CARBONYL CARBON ATOMS
    11.
    发明申请
    PROCESSES AND CATAYLSTS FOR THE SELECTIVE HYDROGENATION OF COMPOUNDS HAVING CARBONYL CARBON ATOMS 有权

    公开(公告)号：US20240368100A1

    公开(公告)日：2024-11-07

    申请号：US18775179

    申请日：2024-07-17

    Applicant: ARCHER-DANIELS-MIDLAND COMPANY

    Inventor： James Brazdil ,  Chi-Cheng Ma

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

    Abstract: 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 BIOBASED PRODUCTS FROM SUGARS
    13.
    发明申请
    PROCESS FOR MAKING BIOBASED PRODUCTS FROM SUGARS 有权

    公开(公告)号：US20220363628A1

    公开(公告)日：2022-11-17

    申请号：US17265004

    申请日：2019-07-31

    Applicant: Archer Daniels Midland Company

    Inventor： James Brazdil ,  Chi-Cheng Ma

    IPC: C07C303/32 ,  B01J23/755 ,  B01J23/644 ,  B01J21/18 ,  B01J21/06 ,  B01J25/02 ,  B01J23/42 ,  B01J23/44 ,  B01J31/02 ,  B01J31/28 ,  B01J29/70 ,  B01J41/07 ,  B01J41/14 ,  C07C213/02

    Abstract: An integrated, co-product capable process is provided for producing taurine in particular with optionally one or both of monoethanolamine and diethanolamine from one or more sugars, comprising pyrolyzing one or more sugars to produce a crude pyrolysis product mixture including glycolaldehyde and formaldehyde; optionally removing formaldehyde from the crude pyrolysis product mixture, then combining the crude pyrolysis product mixture with an aminating agent in the presence of hydrogen and further in the presence of a catalyst to produce at least monoethanolamine from the crude pyrolysis product mixture; optionally recovering diethanolamine from the crude reductive amination product, sulfating at least a portion to all of the monoethanolamine product to produce 2-aminoethyl hydrogen sulfate ester; and sulfonating the 2-aminoethyl hydrogen sulfate ester to produce taurine.

    DEHYDRATION AND AMINATION OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO ALPHA-AMINO ACIDS
    14.
    发明申请
    DEHYDRATION AND AMINATION OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO ALPHA-AMINO ACIDS 有权

    公开(公告)号：US20210163400A1

    公开(公告)日：2021-06-03

    申请号：US17046730

    申请日：2019-04-02

    Applicant: Archer Daniels Midland Company

    Inventor： James Brazdil ,  Donald Rogness ,  Chi-Cheng Ma

    IPC: C07C227/08 ,  B01J23/46

    Abstract: 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).

    Process of making bioderived propylene glycol
    15.
    发明授权
    Process of making bioderived propylene glycol 有权

    公开(公告)号：US09938215B2

    公开(公告)日：2018-04-10

    申请号：US15304666

    申请日：2015-04-09

    Applicant: ARCHER DANIELS MIDLAND COMPANY

    Inventor： Chi-Cheng Ma ,  Todd Werpy

    IPC: C07C29/60 ,  C07C29/151

    CPC classification number: C07C29/60 ,  C07C29/1512 ,  C07C31/205

    Abstract: An improved process for making bioderived propylene glycol from a feed composition including at least one of lactic acid, glycerol, a five carbon sugar, a five carbon sugar alcohol, a six carbon sugar and a six carbon sugar alcohol, wherein production of four carbon and higher diols is reduced by adding base after the initiation of the reaction. In preferred embodiments, the process pH and other process conditions are initially established at targeted values for obtaining the highest conversion for a given catalyst consistent with the production of substantially no pentanediol byproducts in the product mixture, and base is added thereafter to control the process pH proximate to the initially targeted value.

    Dehydration and amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids
    18.
    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

    Applicant: Archer Daniels Midland Company

    Inventor： James Brazdil ,  Donald Rogness ,  Chi-Cheng Ma

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

    Abstract: 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).

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