Method for the production of cyclic diesters, in particular dilactide
AssigneeUhde Inventa-Fischer GmbH
InventorsCaspar Paetz, Udo Muehlbauer, Habib Driouch
Life of this patent
Estimating the term…
Abstract
The present invention relates to a method for the production of cyclic carboxylic acid esters, in particular intramolecular lactones, such as e.g. dilactide, the production of these cyclic esters from oligomeric carboxylic acids being effected by cyclizing depolymerization. During this reaction, a condensation product of these oligomeric carboxylic acids is produced as by-product, i.e. a mixture of higher-molecular oligomeric carboxylic acids which are hydrolyzed in a further step and hence recovered. This hydrolysate can be added again to the cyclizing depolymerization which is implemented in the first step.
Claims15
A method for the production of cyclic esters of general formula I
- in which
- a) in a first step, a part of a mixture of oligomeric carboxylic acids of formula II
- respectively R being selected, in formulae I to II, from linear or branched aliphatic radicals with 1 to 6 carbon atoms and, in formula II, the average value for n being between 2 and 40, is catalytically converted by cyclising depolymerisation into the cyclic diester of general formula I, wherein the catalyst is a tin containing catalyst, wherein the cyclic depolymerisation is implemented at temperatures between 100 and 300° C., and the thereby produced cyclic diester of general formula I is separated, the part of the oligomeric carboxylic acid of formula II, which is not converted into the cyclic diester of general formula I, is made to react to form a residue during the cyclising depolymerisation, which residue comprises a mixture of oligomeric carboxylic acids of formula II with a higher average value for n than the mixture of oligomeric carboxylic acids of formula II fed into the first step,
- b) in a second step, the residue obtained in a first step is hydrolysed at pressures between 500 mbar and 2 bar and/or at temperatures between 50 and 300° C. to a mixture of oligomeric carboxylic acids of formula II, the average value for n being between 1 and 20, an alpha-hydroxycarboxylic acid of formula III,
- or a mixture of oligomeric carboxylic acids of formula II with an average value for n between 1 and 20 and an alpha-hydroxycarboxylic acid of formula III, and
- c) the hydrolysate obtained in the second step is fed at least partially or completely into the first step,
- wherein the cyclising depolymerisation of the first step is implemented until at most 98% by weight of the mixture of oligomeric carboxylic acids of formula II, which is utilized, is converted by the cyclising depolymerisation into the cyclic diester of general formula I.
Dependencies are inferred from the claim text.