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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.
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公开(公告)号：US20140288306A1
公开(公告)日：2014-09-25
申请号：US14297116
申请日：2014-06-05
Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Inventor： David Milstein , Chidambaram Gunanathan
IPC: C07C209/16 , B01J31/14 , C07D305/06 , C07D213/38 , C07D307/52
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
Abstract translation: 本发明提供新型的钌基催化剂，以及通过在这种催化剂存在下使伯醇和氨反应制备胺的方法，以产生胺和水。 根据本发明的方法，伯醇直接与氨反应，以高产率和高的周转数产生伯胺和水。 该反应由新的钌络合物催化，其优选由喹啉基或吖啶基的钳形配体组成。
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公开(公告)号：US08779136B2
公开(公告)日：2014-07-15
申请号：US14058191
申请日：2013-10-18
Applicant: Yeda Research and Development Co. Ltd.
Inventor： David Milstein , Chidambaram Gunanathan
IPC: C07F9/28
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
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4.发明授权公开(公告)号：US11746006B2
公开(公告)日：2023-09-05
申请号：US17416772
申请日：2019-12-30
Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Inventor： David Milstein , You-Quan Zou , Aviel Anaby
CPC classification number: C01B3/0015 , B01J31/189 , B01J31/20 , B01J31/2404 , B01J2231/763 , B01J2531/821
Abstract: This invention provides a reversible hydrogen loading and discharging system and a reversible method for loading and discharging hydrogen. The system and the methods of this invention comprise ethylene glycol as a liquid organic hydrogen carrier and at least one transition metal. By reacting ethylene glycol with at least one transition metal; at least one hydrogen molecule and at least one oligoester of ethylene glycol are formed (hydrogen releasing)⋅, and by reacting at least one oligoester of ethylene glycol with at least one transition metal and at least one hydrogen molecule, at least one ethylene glycol is formed (hydrogen loading).
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公开(公告)号：US09738685B2
公开(公告)日：2017-08-22
申请号：US15017049
申请日：2016-02-05
Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Inventor： David Milstein , Chidambaram Gunanathan , Yehoshua Ben-David , Ekambaram Balaraman , Boopathy Gnanaprakasam , Jing Zhang
IPC: C07K5/12 , C07C209/50 , C07C213/00 , C07C231/00 , C07C231/02 , C07D307/52 , C08L79/02 , C07C67/03 , C07C45/00 , C07C51/235 , C07C67/28 , C07D241/12 , C07D295/185 , C07D487/14 , C07C29/136 , C07C67/39 , C07K1/02 , C07K1/10
CPC classification number: C07K5/12 , C07C29/136 , C07C45/002 , C07C51/235 , C07C67/03 , C07C67/28 , C07C67/39 , C07C209/50 , C07C213/00 , C07C231/00 , C07C231/02 , C07C2601/08 , C07C2601/14 , C07D241/12 , C07D295/185 , C07D307/52 , C07D487/14 , C07K1/02 , C07K1/10 , C08L79/02 , Y02P20/52 , C07C233/05 , C07C235/06 , C07C235/10 , C07C233/36 , C07C211/27 , C07C215/28 , C08L1/00 , C07C69/14 , C07C69/24 , C07C31/04 , C07C31/08 , C07C31/10 , C07C31/12
Abstract: A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.
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Patent Agency Ranking
公开(公告)号：US08889865B2
公开(公告)日：2014-11-18
申请号：US14297116
申请日：2014-06-05
Applicant: Yeda Research and Development Co. Ltd.
Inventor： David Milstein , Chidambaram Gunanathan
IPC: C07F15/00 , B01J21/02 , C07F5/02 , C07C209/16 , C07D307/52 , B01J31/14 , C07D213/38 , C07D305/06
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
Abstract translation: 本发明提供新型的钌基催化剂，以及通过在这种催化剂存在下使伯醇和氨反应制备胺的方法，以产生胺和水。 根据本发明的方法，伯醇直接与氨反应，以高产率和高的周转数产生伯胺和水。 该反应由新的钌络合物催化，其优选由喹啉基或吖啶基的钳形配体组成。
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公开(公告)号：US20140046065A1
公开(公告)日：2014-02-13
申请号：US14058191
申请日：2013-10-18
Applicant: Yeda Research and Development Co. Ltd.
Inventor： David Milstein , Chidambaram Gunanathan
CPC classification number: C07C209/16 , B01J31/146 , C07B43/04 , C07C213/02 , C07C2601/14 , C07D213/38 , C07D305/06 , C07D307/52 , C07F9/60 , C07F9/64 , C07F15/0046 , C07C211/07 , C07C211/17 , C07C211/27 , C07C217/08 , C07C217/58
Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
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公开(公告)号：US12145139B2
公开(公告)日：2024-11-19
申请号：US18351557
申请日：2023-07-13
Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD. , Arkadi Nerush
Inventor： David Milstein , Alex Nerush , Matthias Vogt , Arup Mukherjee , Noel Angel Espinosa-Jalapa , Subrata Chakraborty
Abstract: The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C—C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.
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公开(公告)号：US11731116B2
公开(公告)日：2023-08-22
申请号：US16076697
申请日：2017-02-08
Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD. , Arkadi Nerush
Inventor： David Milstein , Alex Nerush , Matthias Vogt , Arup Mukherjee , Noel Angel Espinosa-Jalapa , Subrata Chakraborty
CPC classification number: B01J31/181 , B01J31/2428 , C07C249/02 , B01J2231/348 , B01J2531/72 , C07B43/06 , C07B43/08
Abstract: The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C—C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a hydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.
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10.发明授权公开(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.
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