Kuraray Co., Ltd.

Kurarayco., Ltd.

Yusuke Murata

Naoya Minamoto

Masahiro Torihara

Ryosuke Shimizu

Mitsumasa Kaneko

A method for producing a 1-acyloxy-2-methyl-2-propene represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in the presence of a catalyst, in a liquid phase, with an amount of the isobutylene used of more than 1 mol and 50 mol or less per 1 mol of the carboxylic acid. 

Method for producing 1-acyloxy-2-methyl-2-propene

A method for producing a 1,3-bisacyloxy-2-methylenepropane represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in a liquid phase, in the presence of a catalyst containing a carrier having carried thereon palladium and a transition metal of Group 11 in the periodic table, and a catalyst activator. 

Method for producing 1,3-bisacyloxy-2-methylene propane

A method of producing a bis-acyloxylated exomethylene compound represented by general formula (III), including reacting a monoacyloxylated exomethylene compound represented by general formula (I), a carboxylic acid represented by general formula (II), and oxygen in a liquid phase in the presence of a catalyst and optionally a solvent: 

Method for producing bis-acyloxylated exomethylene compound

The use of a metal complex containing a ruthenium ion or an osmium ion, and a tridentate aminodicarbene ligand, the tridentate aminodicarbene ligand having one secondary amino group and two specific heterocyclic carbene groups sandwiching the amino group, enables hydrogenation reduction of carbonyl compounds, such as ketones, carboxylic acid esters, lactones, carboxylic acid amides, and lactams, and imine compounds under relatively mild conditions to produce corresponding alcohols, amines, and the like in a high yield with high catalytic efficiency. The metal complex is obtained by a method comprising steps of reacting a specific metal compound with a specific aminodicarbene precursor and subsequently reacting a specific compound. Reduction of a carbonyl compound or an imine compound in the presence of this metal complex using a hydrogen donor makes it possible to reduce the carbonyl compound or imine compound by hydrogenation.

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Tsukuba, Japan

Yusuke Murata