公开(公告)号：US10562767B2

公开(公告)日：2020-02-18

申请号：US15508117

申请日：2015-09-03

Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.

Inventor： David Milstein ,  Peng Hu ,  Eran Fogler

IPC: C01B3/00 ,  C07C29/149 ,  C07C213/00 ,  C07D241/08 ,  C07C231/08 ,  C07C231/10 ,  C07C249/02 ,  C07C209/50 ,  C07C211/10 ,  C07C233/36 ,  C07C237/08 ,  C07C251/08 ,  C07C211/00 ,  C07C215/08

Abstract: The present invention provides a system and method of storing hydrogen (H2) and releasing it on demand, comprising and making use of diaminoalkanes and alcohols, or aminoalcohols as liquid-organic hydrogen carrier systems (LOHC). 2-amino-ethanol (AE) or its N-methyl derivative 2-(methylamino)ethanol undergo catalytic dehydrogenation to form a cyclic dipeptide (glycine anhydride—GA) or its N,N-dimethyl derivative (N,N-dimethyl GA) with release of hydrogen. Similarly, ethylenediamine (ED) and ethanol undergo catalytic dehydrogenation to form N,N′-diacetylethylenediamine (DAE) with release of hydrogen. Glycine anhydride (GA) or N,N-dimethyl-GA may be hydrogenated back to 2-aminoethanol (AE) or 2-(methylamino)ethanol, respectively, each of which functions as a hydrogen storage system. N,N′-diacetylethylenediamine (DAE) may be hydrogenated back to ED and ethanol, which functions as a hydrogen storage system. These reactions may be catalyzed by a variety of compounds or complexes, including Ruthenium complexes as described herein.

公开(公告)号：US10533028B2

公开(公告)日：2020-01-14

申请号：US15508114

申请日：2015-09-03

Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.

Inventor： David Milstein ,  Peng Hu ,  Eran Fogler ,  Jai Anand Garg Narayana Rao

IPC: C07F15/00 ,  C07C29/149 ,  C07C213/00 ,  C07C227/02 ,  C07C231/08 ,  C07C231/10 ,  B01J31/24 ,  C07C67/40 ,  C07C249/02 ,  C07D207/16 ,  C07D241/08

Abstract: The present invention relates to novel Ruthenium complexes of formulae A1-A4 and their use, inter alia, for (1) dehydrogenative coupling of alcohols to esters; (2) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones), or polyesters); (3) preparing amides from alcohols and amines—(including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or polymerization of amino alcohols and/or forming cyclic dipeptides from p-aminoalcohols; (4) hydrogenation of amides (including cyclic dipeptides, polypeptides and polyamides) to alcohols and amines; (5) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (6) dehydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water and a base to form carboxylic acids; and (10) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. The present, invention further relates to the use of certain known Ruthenium complexes for the preparation of amino acids or their salts from amino alcohols.