CS256098B1 - Preparation of 3-oxa-pentadial - Google Patents

Abstract

The solution concerns a method of preparing 3-oxa-pentanedial. The essence of the solution is that 1,5-dihydroxy-3-oxa-pentane (1 mol) is treated with 2 to 10 mols of manganese dioxide monohydrate in a medium of 20 to 40 mols of acetone or methyl ethyl ketone or their mixture for 2 to 8 hours at a temperature of 20 to 40 °C. After the reaction is complete, the resulting product is separated from the catalyst by filtration and from the solvent by distillation. The method of preparation is used in organic chemistry and in the chemistry of biopolymers in the crosslinking and modification of natural substances containing primary amino groups.

Description

The present invention relates to a process for preparing 3-oxa-pentanedial. The essence of the solution is that 1, 5-dihydroxy-3-oxa-pentane (1 mole) is treated with 2 to 10 moles of manganese oxide monohydrate in an environment of 20 to 40 moles of acetone or methyl ethyl ketone or a mixture thereof for 2 to 8 hours at a temperature of 20-40 ° C. After completion of the reaction, the resulting product is separated from the catalyst by filtration and distilled from the solvent. The method of preparation has utility in organic chemistry and in biopolymers chemistry in the blending and modification of natural compounds containing primary amino groups. 256098 256098

The invention relates to a process for the preparation of 3-oxa-pentanedial. Low molecular weight bifunctional aliphatic, aromatic, or lieterocyclic compounds that are capable of reacting with catalytic or structural biopolymers manifest themselves as crosslinking agents. Also 3-oxa-pentanedial has such properties.

Its preparation is based on anhydroalditols [H. R. Greenberg, A. S. Perlin: Carbohydrate Research 35, 195 (1974)] from the condensation product of 2-chloromethyloxirane with glycerol (3,3'-dioxy-propanediol-1,2) [F. J. Lopez Aparicio, Seanz de Buonaga y Seena, J., Gimenez Martinez, J. J .: An. Quim. 72, 975 (1976)] or ozonolysis of 2,5-dihydrofuran [Ger. Offen. 2,554,587]. These processes are disadvantageous due to the difficult availability of starting materials.

The above mentioned drawbacks are solved by the process according to the invention, characterized in that on 1 mol of 1,5-dihydroxy-3-oxapentane is added 2 to 10 moles of manganese dioxide monohydrate in an environment of 20 to 40 moles of acetone or methyl ethyl ketone or their mixture at 20 ° C. to 40 ° C for 2 to 8 hours. The yield of the reaction is almost quantitative. The catalyst deposit of this oxidation reaction is washed with further portions of acetone. The presence of an oxygen atom in the parent pentandial molecule manifests itself by a reduction in the ability of this compound to pass into animal cells and thus by a decrease in the mutagenicity of the compound. The presence of etheric oxygen in the 3-oxapentandial molecule is manifested both by an increase in solubility and by a further increase in boiling point and a reduction in vapor tension compared to the pentandial properties. Example 1 1,5-dihydroxy-3-oxapentane (106 gj was added to a solution of 20 moles of dry acetone and dry manganese dioxide monohydrate was added with stirring (1020 gj) The diethylene glycol oxidation reaction was carried out at 20 ° C for 8 hours. The catalyst slurry was separated by filtration, the separated filter catalyst was washed three times with 1 dm 3 of acetone, and 3-oxa-pentanedial was separated from the reaction filtrate by vacuum distillation after separation of acetone. -oxa-pentanedial had a boiling point of 197 ° C and its bis (2,4-dinitrophenylhydrazone) had a melting point of 156 ° C.

The procedure of Example 1 was followed except that methyl ethyl ketone was used instead of acetone. The yield of 3-oxa-pentadial was 97 / / o. Example 3

The procedure of Example 1 was followed except that the oxidation reaction was carried out at 40 ° C in a mixture of acetone and methylethylglycol (1: 1, 2 moles by volume) for 4 hours. The yield of 3-oxa-pentanedial was 97%.

The invention can be found to be useful in organic chemistry and in biopolymers chemistry in combining and modifying the properties of natural compounds containing primary amino groups using in various sectors of social practice.

Claims (1)

SUBSTANCE Method for the preparation of 3-oxa-pentanedial, characterized in that 2 to 10 moles of manganese dioxide monohydrate are added to 1 mole of 1,5-dihydroxy-3-oxapentane in an environment of 20 to 40 moles of acetone or methyl ethyl ketone or a mixture thereof at 20 to 40. ° C for 2 to 8 hours.