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.

A process for removing water from an oxidative esterification reactor includes (a) conducting an oxidative esterification reaction in a reactor; (b) removing a crude product stream from the reactor; (c) passing a first portion of the crude product stream directly to a product recovery zone; (d) introducing a second portion of the crude product stream to a distillation column to generate a column overheads stream and a column bottoms stream; (e) passing at least a portion of the columns bottoms stream to the product recovery zone; and (f) recycling a recycle stream comprising at least a portion of the overheads stream to the reactor; wherein the recycle stream contains less than 1 weight percent (wt %) water based on the total weight of the recycle stream, wherein the weight ratio of the first portion to the second portion is at least 1:10, and wherein the amount of the recycle stream recycled to the reactor is such that the reactor contains less than or equal to 2.5 wt % water, based on the weight of the reactor contents.

A process for removing water from an oxidative esterification reactor includes (a) conducting an oxidative esterification reaction in a reactor; (b) removing a crude product stream from the reactor; (c) passing a first portion of the crude product stream directly to a product recovery zone; (d) introducing a second portion of the crude product stream to a distillation column to generate a column overheads stream and a column bottoms stream; (e) passing at least a portion of the columns bottoms stream to the product recovery zone; and (f) recycling a recycle stream comprising at least a portion of the overheads stream to the reactor; wherein the recycle stream contains less than 1 weight percent (wt %) water based on the total weight of the recycle stream, wherein the weight ratio of the first portion to the second portion is at least 1:10, and wherein the amount of the recycle stream recycled to the reactor is such that the reactor contains less than or equal to 2.5 wt % water, based on the weight of the reactor contents.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

A method of preparing a compound of formula (I): ##STR00001##
is disclosed. The compound of formula (I) can be used as an antioxidant agent. The compound can also be used as an antibacterial agent to inhibit Staphylococcus aureus MRSA 18-222 and Pseudomonas aeruginosa MDR-PA 18-1774.

A method of preparing a compound of formula (I): ##STR00001##
is disclosed. The compound of formula (I) can be used as an antioxidant agent. The compound can also be used as an antibacterial agent to inhibit Staphylococcus aureus MRSA 18-222 and Pseudomonas aeruginosa MDR-PA 18-1774.

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R.sup.1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring. ##STR00001##

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R.sup.1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring. ##STR00001##