826-91-5Relevant articles and documents
Hydroxynated nylons based on unprotected esterified D-Glucaric acid by simple condensation reactions
Kiely,Chen,Lin
, p. 571 - 578 (1994)
Convenient procedures are described for the preparation of hydroxylated nylons (polyhydroxypolyamides) from D-glucaric acid. The procedures, which do not require protection/deprotection of carbohydrate hydroxyl groups, can be used to make a variety of polymers with a range of properties from D-glucaric acid. Simple alcohol (e.g. methanol or ethanol) esterification mixtures of D-glucaric acid (from oxidation of D-glucose) were reacted with bis-primary diamines in a polar solvent, typically methanol, to produce the polyamides. D-Glucaric acid esterification mixtures contain varying amounts of dialkyl D-glucarate, alkyl-D glucarate 1,4-lactone, and alkyl, D-glucarate 6,3-lactone. These ester forms of D-glucaric acid are also in equilibrium under the conditions of the polymerization. Diamines employed included linear alkylenediamines, a branched alkylenediamine, arylalkylenediamines, and diamines with oxygen or nitrogen atoms in the alkylene chain. Considerable differences in polymers physical properties were observed by changing the diamine monomer. Linear aliphatic and arylalkylenediamines gave crustalline solid polyamides with high melting points. The C2 and C4 diamine copolymers were water soluble, whereas the C6 and above were water insoluble. The branched diamine copolymer and those with oxygen or nitrogen in the diamine chain had lower melting points and higher alcohol solubility than the unbranched alkylenediamine copolymers.
METHOD OF PREPARING D-GLUCARO-1,4:6,3-DILACTONE
-
Paragraph 0069-0071, (2020/03/09)
Disclosed is a method of preparing d-glucaro-1,4:6,3-dilactone using an organic acid or a salt thereof, such that d-glucaro-1,4:6,3-dilactone having high purity can be obtained using potassium glucarate as the organic acid, and simultaneously, the economic efficiency of the preparation process can be remarkably improved.
D-GLUTARIC ACID ESTERS/LACTONES USED IN CONDENSATION POLYMERIZATION TO PRODUCE HYDROXYLATED NYLONS - A QUALITATIVE EQUILIBRIUM STUDY IN ACIDIC AND BASIS ALCOHOL SOLUTIONS
Chen, Liang,Kiely, Donald E.
, p. 585 - 602 (2007/10/02)
Direct esterification of D-glutaric acid in acidic methanol solution produced a mixture of four esters/lactones: dimethyl D-glucarate (1), methyl D-glucarate 1,4-lactone (2), methyl D-glucarate 6,3-lactone (3), and D-glucaro-1,4:6,3-dilactone (4).The esters/lactones described in this study are activated forms of D-glucaric acid useful for condensation polymerization with diamines to produce hydroxylated nylons.Structures of the esterification products were determined using 1H NMR, 13C NMR and GC/MS techniques.Qualitative changes in equilibrium concentrations of the esters/lactones mixtures, as determined from 1H NMR spectral studies, were observed in acidic (methanol-d4/HCl) and basis (methanol-d4/triethylamine) alcohol solutions.Esterification of D-glucaric acid in ethanol produced ethyl esters/lactones mixtures which were observed to undergo changes in equilibrium composition in acidic and basic ethanol solutions comparable to those found with the methyl esters/lactones mixtures.
