Amphiphilic Amide Derivatives of D‐Glucaric Acid. Synthesis and Complexing Properties Toward Lanthanide(III) Ions

Abstract

Hydrophobic derivatives of D‐glucaric acid, HOOC−(CHOH)4−CONHR,where R is an alkyl chain having 3, 8, 10, or 12 carbon atoms, have been synthesized from D‐glucaro‐1,4‐lactone and the corresponding amines. The complexing abilities of these compounds toward trivalent lanthanide cations have been studied, using the water‐soluble propyl compound, and compared to that of gulonic acid, which corresponds to the complexing part of these molecules. The formation constants of the complexes have been determined and their structures discussed. The surfactant properties of the C8, C10 and C12 glucaramides and their extracting ability toward LnIII ions have also been evaluated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

Synthesis and Surfactant Properties of Nonionic Biosourced Alkylglucuronamides

“…Starting from glucuronolactone 9 for the C 8 glucoside 10a provides the product with a better yield (76%) under the same conditions. For all the products, only the beta isomer on the anomeric position was obtained according to the 13 C NMR shift at 110 ppm instead of 104 ppm for the alpha isomers in the furanoside series. 31 Another reported protocol using supported sulfuric acid on silica may offer 10% of the alpha isomer.…”

“…Glucose 2 can be oxidized on its anomeric position to provide gluconic acid which lactonizes to give the lactone 3 (also referred as gluconolactone). Such lactone can be opened by an amine to provide 4 ( path b ). , Starting from glucaric acid 5 , the use of two equivalents of amine allows obtaining of the ammonium carboxylate function and the amide, giving a product which lactonizes ( 6 ) under acidic conditions ( path c ) . Lastly, glucuronic acid 7 can be used as a precursor to provide glucamides.…”

“…11,12 Starting from glucaric acid 5, the use of two equivalents of amine allows obtaining of the ammonium carboxylate function and the amide, giving a product which lactonizes (6) under acidic conditions (path c). 13 Lastly, glucuronic acid 7 can be used as a precursor to provide glucamides. Direct amidation of 7 has not been reported, but compound 8 has been obtained through per-acetylation of glucuronic acid 3 to give the mixed anhydride, followed by amidation and deacetylation (path d).…”

Aerobic Oxidation of Glucose to Glucaric Acid under Alkaline-Free Conditions: Au-Based Bimetallic Catalysts and the Effect of Residues in a Hemicellulose Hydrolysate

“…It has been ranked as a “top value-added chemical” from biomass by the US Department of Energy; however, the full potential of glucaric acid has not yet been exploited. It is used in the formulation of phosphate-free detergents and metal complexation agents and as a monomer in the preparation of a variety of biopolymers, ,− and it is an intermediate in the production of biobased adipic acid. , It has been recently identified as a corrosion inhibitor that can be applied to road deicers and cooling towers, and it has been qualified as a concrete admixture for set retardancy and water reduction . Its derivatives have also been studied for medical and cosmetic purposes. − However, the chemical has not yet been produced in sufficient volumes or cost-competitively enough, because of the difficulty of commercial scale production and restrictions in market uptake.…”

Oxidation of Aldoses Contained in Softwood Hemicellulose Acid Hydrolysates into Aldaric Acids under Alkaline or Noncontrolled pH Conditions

“…Glucaric acid, derived from glucose, has been ranked as a “top value-added chemical” from biomass . It is a promising raw material for polymers, as well as detergent builder, chelating agent, deicing agent, and corrosion inhibitor. − Its derivatives have also been studied for therapeutic purposes. , Aside from glucaric acid, the other carbohydrate diacids (mannaric, galactaric or mucic, xylaric, and arabinaric acids) could also be used to make a range of bioproducts, and a class of polymers referred as polyhydroxypolyamides, − or silicon polyamides . Oxidation of the aldoses to the corresponding aldaric acids can be conducted using nitric acid, ,− TEMPO or 4-acetylamino-TEMPO mediated oxidation in aqueous solutions at high pH of 11–12 .…”