Herein is provided a process for combined renewable 1-decene and renewable carboxylic diacid production from a fatty acid ester containing feedstock, wherein the feedstock is first subjected to metathesis reaction conditions, recovery of 1-decene and then to microbial oxidation to yield diacids in a fermentation broth. Diacids of unusual carbon chains lengths are thereby obtainable.

Herein is provided a process for combined renewable 1-decene and renewable carboxylic diacid production from a fatty acid ester containing feedstock, wherein the feedstock is first subjected to metathesis reaction conditions, recovery of 1-decene and then to microbial oxidation to yield diacids in a fermentation broth. Diacids of unusual carbon chains lengths are thereby obtainable.

A process for manufacturing a substituted cyclohexanecarbonitrile said process comprising the following steps: —reacting the corresponding substituted cyclohexanecarboxylic acid with thionyl chloride to make the corresponding acyl chloride; and simultaneously or subsequently —reacting the chloride with sulfonamide in sulfolane as solvent to make the substituted cyclohexanecarbonitrile.

A process for manufacturing a substituted cyclohexanecarbonitrile said process comprising the following steps: —reacting the corresponding substituted cyclohexanecarboxylic acid with thionyl chloride to make the corresponding acyl chloride; and simultaneously or subsequently —reacting the chloride with sulfonamide in sulfolane as solvent to make the substituted cyclohexanecarbonitrile.

The present invention relates to the technical field of chiral synthesis, and specifically provides a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.

The present invention relates to the technical field of chiral synthesis, and specifically provides a new type of oxa-spirodiphosphine ligands. The bisphosphine ligand is prepared with oxa-spirobisphenol as a starting material after triflation, palladium catalyzed coupling with diaryl phosphine oxide, reduction of trichlorosilane, further palladium catalyzed coupling with diaryl phosphine oxide, and further reduction of trichlorosilane. The oxa-spiro compound has central chirality, and thus includes L-oxa-spirodiphosphine ligand and R-oxa-spirodiphosphine ligand. The racemic spirodiphosphine ligand is capable of being synthesized from racemic oxa-spirobisphenol as a raw material. The present invention can be used as a chiral ligand in the asymmetric hydrogenation of unsaturated carboxylic acids. The complex of the ligand with ruthenium can achieve an enantioselectivity of greater than 99% in the asymmetric hydrogenation of methyl-cinnamic acid.

A method of reducing an aromatic ring or a cyclic, allylic ether in a compound includes preparing a reaction mixture including a compound including an aromatic moiety or a cyclic, allylic ether moiety, an alkali metal, and either ethylenediamine, diethylenetriamine, triethylenetetramine, or a combination thereof, in an ether solvent; and reacting the reaction mixture at from −20° C. to 30° C. for a time sufficient to reduce a double bond in the aromatic moiety to a single bond or to reduce the cyclic, allylic ether moiety.

A method of reducing an aromatic ring or a cyclic, allylic ether in a compound includes preparing a reaction mixture including a compound including an aromatic moiety or a cyclic, allylic ether moiety, an alkali metal, and either ethylenediamine, diethylenetriamine, triethylenetetramine, or a combination thereof, in an ether solvent; and reacting the reaction mixture at from −20° C. to 30° C. for a time sufficient to reduce a double bond in the aromatic moiety to a single bond or to reduce the cyclic, allylic ether moiety.

Provided is a hydrogenation method of a phthalate compound. According to the present invention, stereoselectivity of the hydrogenation reaction may be increased, and thus the content of a cis isomer in a product may be increased. As a result, quality of the hydrogenation product as a plasticizer may be improved.

Provided is a hydrogenation method of a phthalate compound. According to the present invention, stereoselectivity of the hydrogenation reaction may be increased, and thus the content of a cis isomer in a product may be increased. As a result, quality of the hydrogenation product as a plasticizer may be improved.