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.

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.

The present invention provides a system and method of storing hydrogen (H.sub.2) 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.

The present invention provides a system and method of storing hydrogen (H.sub.2) 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.

The present invention provides a system and method of storing hydrogen (H.sub.2) 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.

The filter medium is a filter medium which uses a liquid containing oil and water as a separation target, and has a channel for the liquid. The filter medium includes a base constituting the channel, and one or more of nitrogen-containing fluorine compounds which are provided on at least a portion of a surface of the channel. The nitrogen-containing fluorine compound includes an oil-repellency imparting group and any one hydrophilicity imparting group selected from a group consisting of an anion type, a cation type, and an amphoteric type, in a molecule.

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.

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.

An anionic-cationic-nonionic surfactant as substantially represented by the formula (I) exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced.

##STR00001##

In the formula (I), each group is as defined in the specification.

An anionic-cationic-nonionic surfactant as substantially represented by the formula (I) exhibits significantly improved interfacial activity and stability as compared with the prior art. With the present anionic-cationic-nonionic surfactant, a flooding fluid composition for tertiary oil recovery with improved oil displacement efficiency and oil washing capability as compared with the prior art could be produced.

##STR00001##

In the formula (I), each group is as defined in the specification.