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Preferred IUPAC name 2,2′-Oxydiacetic acid | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.003.476 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H6O5 | |
Molar mass | 134.09 g/mol |
Melting point | 140-144°C |
Acidity (pKa) | 2.79, 3.93 (20°C) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diglycolic acid is an aliphatic dicarboxylic acid, its acidity is between the one of acetic acid and oxalic acid. [1] It is formed in the oxidation of diethylene glycol in the body and can lead to severe complications with fatal outcome. [2]
Oxidation of diethylene glycol with concentrated nitric acid was described by A. Wurtz in 1861 [3]
In parallel, W. Heintz reported the synthesis of diglycolic acid from chloroacetic acid by heating with sodium hydroxide solution. [4]
In a version with barium hydroxide solution as an alkaline medium, diglycolic acid is obtained in 68% yield after acidification. [5]
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%. [6] 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. [7]
The oxidation of diethylene glycol with air, oxygen or ozone avoids the use of expensive nitric acid and prevents the inevitable formation of nitrous gases. [8] In the presence of a platinum catalyst, yields of 90% can be obtained by air oxidation. [9]
On a bismuth platinum contact catalyst, yields of 95% are to be achieved under optimized reaction conditions. [10]
The oxidation of 1,4-dioxan-2-one (p-dioxanone, a lactone which is used as a comonomer in biodegradable polyesters with nitric acid or dinitrogen tetroxide) is also described with yields of up to 75%. [11]
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 free-flowing flakes. [12]
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). [13]
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 exchangers or steam boilers. [14]
Diglycolic acid can be used as a diester component in homo- and copolymeric polyesters (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: [15]
Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space.
Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.
Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization. PGA has been known since 1954 as a tough fiber-forming polymer. Owing to its hydrolytic instability, however, its use has initially been limited. Currently polyglycolide and its copolymers (poly(lactic-co-glycolic acid) with lactic acid, poly(glycolide-co-caprolactone) with ε-caprolactone and poly (glycolide-co-trimethylene carbonate) with trimethylene carbonate) are widely used as a material for the synthesis of absorbable sutures and are being evaluated in the biomedical field.
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic 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 HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.
Wilhelm Rudolph Fittig was a German chemist. He discovered the pinacol coupling reaction, mesitylene, diacetyl and biphenyl. Fittig studied the action of sodium on ketones and hydrocarbons. He discovered the Fittig reaction or Wurtz–Fittig reaction for the synthesis of alkylbenzenes, he proposed a diketone structure for benzoquinone and isolated phenanthrene from coal tar. He discovered and synthesized the first lactones and investigated structures of piperine, naphthalene, and fluorene.
Polyester is a category of polymers that contain one or two ester linkages 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 naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.
The Hunsdiecker reaction is a name reaction in organic chemistry whereby silver salts of carboxylic acids react with a halogen to produce an organic halide. It is an example of both a decarboxylation and a halogenation reaction as the product has one fewer carbon atoms than the starting material and a halogen atom is introduced its place. A catalytic approach has been developed.
Dimethyl oxalate is an organic compound with the formula (CO2CH3)2 or (CH3)2C2O4. It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water.
Polybutylene succinate (PBS) is a thermoplastic polymer resin of the polyester family. PBS is a biodegradable aliphatic polyester with properties that are comparable to polypropylene.
Poly(ethylene succinate) (PES) is an aliphatic synthetic polyester with a melting point from 103–106 °C. It is synthesized from dicarboxylic acids; either by ring-opening polymerization of succinic anhydride with ethylene oxide or by polycondensation of succinic acid and ethylene glycol. Thermophilic Bacillus sp. TT96 is found in soil and can degrade PES. Mesophilic PES degrading microorganisms were found in the Bacillus and Paenibacillus species; strain KT102; a relative of Bacillus pumilus was the most capable of degrading PES film. The fungal species NKCM1003 a type of Aspergillus clavatus also degrades PES film. The solubility of lithium salts (e.g. lithium perchlorate, LiClO4) in PES made it a good alternative to poly(ethylene oxide) (PEO) during early development of solid polymer electrolytes for lithium ion batteries.
N-Hydroxyphthalimide is the organic compound with the formula C6H4(CO)2NOH. A white or yellow solid, it is a derivative of phthalimide. The compound is as a catalyst in the synthesis of other organic compounds. It is soluble in water and organic solvents such as acetic acid, ethyl acetate and acetonitrile.
2-Methylglutaronitrile is the organic compound with the formula NCCH2CH2CH(CH3)CN. This dinitrile is obtained in the large-scale synthesis of adiponitrile. It is a colorless liquid with an unpleasant odor. It is the starting compound for the vitamin nicotinamide and for the diester dimethyl-2-methylglutarate and the ester amide methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, which are promoted as green solvents. 2-Methylglutaronitrile is chiral but is mainly encountered as the racemate. It is also used to make Dytek A.
p-Dioxanone (1,4-dioxan-2-one) is the lactone of 2-(2-hydroxyethoxy)acetic acid. It is a monomer that can undergo ring-opening polymerization to give polydioxanone, a biodegradable implant material. It is isomeric to trimethylene carbonate (1,3-dioxan-2-one).
1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.
1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds possessing nucleophilic functional groups, for example hydroxy groups (as in the case of β-cyclodextrin) or amino groups (as in the case of polymethine dyes). In such, the sulfobutyl group is present as neutral sodium salt and considerably increases the water solubility of the derivatives.
Itaconic anhydride is the cyclic anhydride of itaconic acid and is obtained by the pyrolysis of citric acid. It is a colourless, crystalline solid, which dissolves in many polar organic solvents and hydrolyzes forming itaconic acid. Itaconic anhydride and its derivative itaconic acid have been promoted as biobased "platform chemicals" and bio- building blocks.) These expectations, however, have not been fulfilled.
5-Amino-1-pentanol is an amino alcohol with a primary amino group and a primary hydroxy group at the ends of a linear C5-alkanes. As a derivative of the platform chemical furfural (that is easily accessible from pentoses), 5-amino-1-pentanol may become increasingly important in the future as a building block for biodegradable polyesteramides and as a starting material for valerolactam — the monomer for polyamides.
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