Processes for the preparation of D-chiro-inositol

• US 5,714,643 A
• Filed: 02/09/1996
• Issued: 02/03/1998
• Est. Priority Date: 08/11/1993
• Status: Expired due to Fees

• Current Assignee: Hokko Chemical Industry Company Limited, Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
• Original Assignee: Hokko Chemical Co. Ltd., Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
• Inventors: Sato, Kiyoshi, Yoshida, Makoto, Hirazawa, Kiyoshi, Kanbe, Kenji, Takeuchi, Tomio
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): White, Everett
• Application Number:
  US08/596,131
• Time in Patent Office: 725 Days
• Field of Search: 568/833
• US Class Current: 568/833
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 29/10 of ethers, including cyclic ethers, e.g. oxiranes
• CPC Class Codes: C07C 35/16 Inositols

Abstract

An aqueous solution of kasugamycin or its salt is either mixed with a strongly acidic ion-exchange resin of the H⁺ -form in a reaction vessel, or is brought into contact with a strongly acidic ion-exchange resin of the H⁺ -form in a column containing said resin, followed by heating said aqueous solution and the resin under an atmospheric pressure or an elevated pressure, thereby to effect hydrolytic reaction of kasugamycin. By this reaction, an acidic reaction solution containing D-chiro-inositol is produced. This acidic reaction solution containing D-chiro-inositol is separated from the strongly acidic ion-exchange resin. Subsequently, D-chiro-inositol is recovered from the reaction solution. For this recovery, the acidic reaction solution is passed successively through a column of a strongly acidic ion-exchange resin of the H⁺ -form and through a column of a strongly basic ion exchange resin of the OH^- -form, so that a neutral aqueous eluate containing D-chiro-inositol is obtained. This neutral aqueous eluate is then concentrated and crystals of D-chiro-inositol are made to deposit, whereby D-chiro-inositol of a high purity can be harvested with high efficiency.

Claims

1. A process for the preparation of D-chiro-inositol comprising mixing an aqueous solution of kasugamycin or a salt thereof with particles of a strongly acidic ion-exchange resin of the H⁺ -form, heating the resulting mixture under an atmospheric pressure or an elevated pressure to effect hydrolysis of kasugamycin, separating the resulting acidic reaction solution containing D-chiro-inositol so formed, from the strongly acidic ion-exchange resin, thereby to obtain the acidic reaction solution containing D-chiro-inositol, and then recovering D-chiro-inositol from said acidic reaction solution.

2. A process for the preparation of D-chiro-inositol comprising continuously introducing an aqueous solution of kasugamycin or a salt thereof into a column packed with a strongly acidic ion-exchange resin of the H⁺ -form, heating the aqueous solution of kasugamycin and the resin within said column under an atmospheric pressure or an elevated pressure to effect hydrolysis of kasugamycin, allowing the resulting acidic reaction solution containing D-chiro-inositol so formed, to flow out of the resin column, and recovering D-chiro-inositol from said acidic reaction solution.

3. A process for the preparation of D-chiro-inositol comprising conducting successively the following first to fourth steps:

in a first step, mixing an aqueous solution of kasugamycin or a salt thereof with particles of a strongly acidic ion-exchange resin of the H⁺ -form, heating the resulting mixture under an atmospheric pressure or an elevated pressure to effect hydrolysis of kasugamycin, separating the resulting acidic reaction solution containing D-chiro-inositol so formed, from the strongly acidic ion-exchange resin, thereby to obtain the acidic reaction solution containing D-chiro-inositol,

in a second step, passing said acidic reaction solution so obtained in the first step, through a column packed with a strongly acidic ion-exchange resin of the H⁺ -form, to eliminate the basic impurities contained in said reaction solution and, removing any unreacted kasugamycin, whereby an acidic aqueous solution containing D-chiro-inositol is obtained,

in a third step, passing said acidic aqueous solution so obtained in the second step, through a column packed with a strongly basic ion-exchange resin of the OH^- -form, thereby to obtain a neutralized aqueous eluate containing D-chiro-inositol, and

in a fourth step, concentrating said eluate so obtained in the third step, to deposit D-chiro-inositol of a high purity from the resulting concentrated solution.

4. A process for the preparation of D-chiro-inositol comprising conducting the following first to fourth steps:

in a first step, continuously introducing an aqueous solution of kasugamycin or a salt thereof into a column packed with a strongly acidic ion-exchange resin of the H⁺ -form, heating under an atmospheric pressure or an elevated pressure the aqueous solution of kasugamycin and the resin within the column to effect hydrolysis of the kasugamycin, and allowing the resulting acidic reaction solution containing d-chiro-inositol so formed, to flow out of the resin column, thereby to obtain the acidic reaction solution containing D-chiro-inositol,

in a second step, passing the acidic reaction solution so obtained in the first step, through a column packed with a strongly acidic ion-exchange resin of the H⁺ -form, to eliminate the basic impurities contained in said reaction solution and, removing any unreacted kasugamycin, whereby an acidic aqueous solution containing D-chiro-inositol is obtained,

in a third step, passing said acidic aqueous solution so obtained in the second step, through a column packed with a strongly basic ion-exchange resin of the OH^- -form, thereby to obtain a neutralized aqueous eluate containing D-chiro-inositol, and

in a fourth step, concentrating said eluate so obtained in the third step, to deposit D-chiro-inositol of a high purity to deposit from the resulting concentrated solution.