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. ##STR00001## ##STR00002##

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

The present invention relates to a process for the manufacturing of 3-phenylpropan-1-ol, from nature derived starting material, wherein said nature derived starting material comprises not less than 80 wt. % of cinnamaldehyde. In another aspect, the present invention relates to the process, which further comprises the steps: a) conversion of cinnamaldehyde as starting material to 3-phenylpropan-1-ol by a catalytic hydrogenation; b) optional purification of the 3-phenylpropan-1-ol by alkaline water extraction; c) distillation of 3-phenylpropan-1-ol. In a third aspect the present invention relates to use of 3-phenylpropan-1-ol obtained by the process of the invention in perfumes and/or personal care and/or cleaning products.

The present invention relates to a process for the manufacturing of 3-phenylpropan-1-ol, from nature derived starting material, wherein said nature derived starting material comprises not less than 80 wt. % of cinnamaldehyde. In another aspect, the present invention relates to the process, which further comprises the steps: a) conversion of cinnamaldehyde as starting material to 3-phenylpropan-1-ol by a catalytic hydrogenation; b) optional purification of the 3-phenylpropan-1-ol by alkaline water extraction; c) distillation of 3-phenylpropan-1-ol. In a third aspect the present invention relates to use of 3-phenylpropan-1-ol obtained by the process of the invention in perfumes and/or personal care and/or cleaning products.

A catalyst includes a carrier, and a metal obtained by reducing a metal ion supported on the carrier 1) in a supercritical state or 2) in a polar organic solvent, wherein the carrier is an inorganic porous body having a hierarchical porous structure. By employing the catalyst, it is possible to exhibit better catalytic activity than a conventional catalyst. Heat generation and spontaneous ignition are prevented because no organic porous body is used.

A catalyst includes a carrier, and a metal obtained by reducing a metal ion supported on the carrier 1) in a supercritical state or 2) in a polar organic solvent, wherein the carrier is an inorganic porous body having a hierarchical porous structure. By employing the catalyst, it is possible to exhibit better catalytic activity than a conventional catalyst. Heat generation and spontaneous ignition are prevented because no organic porous body is used.

A mixture of two alkoxylates surfactants, one being an aryl aliphatic carbinol alkoxylate, the other one being a dialiphatic carbinol alkoxylate, said mixture being useful for stabilizing emulsions and dispersions used in agricultural or pharmaceutical formulations. The alkoxylates surfactants may serve as substitutes for nonylphenol ethoxylates (NPE) and tristyrylphenol ethoxylates (TSE).