Japan Tobacco Inc.

Makoto Shibagaki

Hajime Matsushita

Kyoko Takahashi

Hideyuki Kuno

Masataka Mori

Ichiro Honda

The present invention relates to a method of preparing an alcohol by reducing a carboxylic acid or a derivative thereof, more particularly, a method of preparing an alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst. A carboxylic acid or a carboxylic acid derivative is converted into a corresponding alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst using an alcohol as a hydrogen source. An alcohol can be prepared in a high yield in the present invention. To be more specific, the method of the present invention can convert a higher fatty acid or a carboxylic acid derivative, which has given a corresponding alcohol in a low yield in the presence of a zirconium catalyst alone, into the corresponding alcohol in a high yield. Further, the reaction can be performed easily, and the product can be easily separated from the catalyst.

Method of preparing an alcohol

Disclosed is a method of obtaining (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone (2) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone (3) by resolving a racemic mixture of the compounds (2) and (3). More specifically, disclosed is a method of obtaining the optically active nicotine derivatives (2) and (3) shown below, which comprises steps of binding (.+-.)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone to a sugar derivative, resolving the obtained compound into two types of stereoisomers, and treating them under an acidic condition. ##STR1##

Optical resolution method of a nicotine derivate

Method of producing aldehyde by oxidation of primary alcohol

Levoglucosenone is prepared by reaction sequence using 1,6-anhydro-.beta.-D-galactopyranose as a starting material. First, the starting material is reacted with ortho formate, obtaining an ortho ester of said starting material. Then, the ortho ester is placed under the conditions for a reductive elimination reaction of the ortho formate part of said ortho ester, thereby converting said ortho ester to a 1,6-anhydro-3,4-dideoxy derivative. The dideoxy derivative is placed under the conditions for oxidation of the hydroxy group of said dideoxy derivative, thereby forming levoglucosenone.

Method of preparing levoglucosenone

Disclosed is a process of reduction of aldehydes or ketones by means of reaction with alcohols, in the presence of a catalyst, to produce alcohols which correspond to said respective aldehyde or ketone. A solid of partially dehydrated one or more metal hydroxides whose metal is selected from the group consists of titanium, tin, ion, aluminum, cerium, and niobium is used as the catalyst. This process can be conducted either in a gas phase or in a liquid phase.

Catalyst for the reduction of aldehydes and ketones

An alcohol compound is produced by reducing a carboxylic acid or an ester thereof with an alcohol in the presence of a solid catalyst. The catalyst includes a hydrous metal oxide belonging to Group IV of the Periodic Table.

Method of producing alcohol compounds

An amine is reached with dimethyformamioe in the presence of a solid catalyst to produce a formamide corresponding to the amine. The solid catalyst includes an oxide of metals belonging to Groups III, IV and V of the Periodic Table.

Method of producing formamide compounds

A carboxylic acid or its ester is reduced by formic acid in the presence of a hydrous metal oxide solid catalyst, to produce a corresponding aldehyde. Using this method, no harmful waste is by-produced, an aldehyde compound can be produced at relatively low cost, and the aldehyde produced can be easily recovered.

Method of producing aldehyde compound

A method of preparing an acetal or ketal from a corresponding aldehyde or ketone is disclosed. A hydrous oxide of an element of Group IV of the Periodic Table is used as a catalyst, and the aldehyde or ketone is caused to react with an alcohol. The hydrous oxide can be obtained by partially dehydrating a hydroxide of the corresponding element. The method does not require an acid catalyst and is applicable to a carbonyl compound which is not stable in acids.

Method of preparing acetal or ketal

A method of reducing a nitrile into a corresponding alcohol is disclosed. The nitrile is caused to react with an alcohol by using a zirconium hydrous oxide as a catalyst. The zirconium hydrous oxide is obtained by partially dehydrating zirconium hydroxide. The nitrile can be reduced to the corresponding alcohol in a one-step reaction.

Method of reducing nitrile into a corresponding alcohol

Disclosed is a process of reduction of aldehydes or ketones by means of reaction with alcohols, in the presence of a catalyst, to produce alcohols which correspond to said respective aldehyde or ketone. A solid of partially dehydrated one or more metal hydroxides whose metal is selected from the group consists of titanium, tin, ion, aluminium, cerium, and niobium is used as the catalyst. This process can be conducted either in a gas phase or in a liquid phase.

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Kawasaki, Japan

Makoto Shibagaki