Diglycolic acid is an aliphatic

dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show ...

, its

acidity In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

is between the one of

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

and

oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early inve ...

. It is formed in the oxidation of

diethylene glycol Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon dimer of ethylene glycol. It is miscible in water, alcohol, ...

in the body and can lead to severe complications with

fatal Fatal may refer to: * ''Fatal'' (album), by Hussein Fatal, 2002 * ''Fatal'' (film), a 2010 French film starring Michaël Youn and Stéphane Rousseau * '' F.A.T.A.L.'', a tabletop role-playing game released in 2003 * Fatal Recordings, a record la ...

outcome.

Preparation

Oxidation of

with concentrated

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...

was described by A. Wurtz in 1861 In parallel, W. Heintz reported the synthesis of diglycolic acid from

chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds ...

by heating with

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

solution. In a version with

barium hydroxide Barium hydroxide is a chemical compound with the chemical formula Ba(OH)2. The monohydrate (''x'' = 1), known as baryta or baryta-water, is one of the principal compounds of barium. This white granular monohydrate is the usual commercial form. P ...

solution as an alkaline medium, diglycolic acid is obtained in 68% yield after

acidification Acidification may refer to: * Ocean acidification, decrease in the pH of the Earth's oceans * Freshwater acidification, atmospheric depositions and soil leaching of SOx and NOx * Soil acidification, buildup of hydrogen cations, which reduces the ...

. The yields of the described reactions are unsatisfactory for use on a technical scale. The single-stage nitric acid process gives even in the presence of an oxidation catalyst ( vanadium(V)oxide) yields of only 58-60%. In a multi-stage process of nitric acid oxidation at 70 °C and multiple crystallization steps, evaporation of the residues and return of the diethylene glycol-containing mother liquor, product yields of up to 99% (based on diethylene glycol) can be achieved. The oxidation of diethylene glycol with air, oxygen or

ozone Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lo ...

avoids the use of expensive nitric acid and prevents the inevitable formation of nitrous gases. In the presence of a

platinum Platinum is a chemical element with the symbol Pt and atomic number 78. It is a dense, malleable, ductile, highly unreactive, precious, silverish-white transition metal. Its name originates from Spanish , a diminutive of "silver". Platinu ...

catalyst, yields of 90% can be obtained by air oxidation. On a

bismuth Bismuth is a chemical element with the Symbol (chemistry), symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental ...

platinum contact catalyst, yields of 95% are to be achieved under optimized reaction conditions. The oxidation of 1,4-dioxan-2-one ( p-dioxanone, a

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

which is used as a comonomer in biodegradable polyesters with nitric acid or dinitrogen tetroxide) is also described with yields of up to 75%.

Properties

Diglycolic acid is readily water soluble and crystallizes from water in monoclinic prisms as a white, odorless solid. At an air humidity of more than 72% and 25 °C the monohydrate is formed. The commercial product is the anhydrous form as a free-flowing flakes.

Application

Diesters of diglycolic acid with (branched) higher alcohols can be used as softeners for polyvinyl chloride (PVC) with comparable properties as di-n-octyl phthalate (DOP). Basic solutions of diglycolic acid are described for the removal of limescale deposits in gas and oil bores, as well as in systems such as

heat exchanger A heat exchanger is a system used to transfer heat between a source and a working fluid. Heat exchangers are used in both cooling and heating processes. The fluids may be separated by a solid wall to prevent mixing or they may be in direct contac ...

s or

steam boilers Steam is a substance containing water in the gas phase, and sometimes also an aerosol of liquid water droplets, or air. This may occur due to evaporation or due to boiling, where heat is applied until water reaches the enthalpy of vaporization. ...

. Diglycolic acid can be used as a diester component in homo- and

copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...

polyester Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...

s (so-called polyalkylene diglycolates) which are biocompatible and biodegradable and can be used alone or in blends with aliphatic polyesters as tissue adhesives, cartilage substitutes or as implant materials: Synthese von Polyalkylenglycolaten

References

{{Reflist Dicarboxylic acids Ethers