Dodecanedioic acid (DDDA) is a

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 ...

with the formula . A white solid, the compound finds a variety of applications ranging from polymers to materials. The unbranched compound is the most commonly encountered C12 dicarboxylic acid.

Production

DDDA has traditionally been produced from

butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...

using a multi-step chemical process. Butadiene is first converted to

cyclododecatriene Cyclododecatrienes are cyclic trienes with the formula C12H18. Four isomers are known for 1,5,9-cyclododecatriene. The ''trans'',''trans'',''cis''-isomer is a precursor in the production of nylon-12. : Production The ''trans'',''trans'',''cis'' ...

through

cyclotrimerization In organic chemistry, an alkyne trimerisation is a +2+2nbsp;cycloaddition reaction in which three alkyne units () react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applica ...

. The triene is then hydrogenated to

cyclododecane Cyclododecane is an organic compound with the chemical formula (CH2)12. It is a waxy white solid at room temperature, and is soluble in nonpolar organic solvents. It is an intermediate of Nylon 12, polyesters, and synthetic lubricating oils. ...

Autoxidation Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organi ...

by air in the presence of

boric acid Boric acid, more specifically orthoboric acid, is a compound of boron, oxygen, and hydrogen with formula . It may also be called hydrogen borate or boracic acid. It is usually encountered as colorless crystals or a white powder, that dissolves ...

gives a mixture of cyclodecanol and the

cyclododecanone Cyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature. It is produced by the oxidation of cyclododecane via cyclododecanol. Cyclododecanone is mainly consumed a ...

. In the final step, this mixture oxidized to the diacid using

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 ...

. An alternative route involves

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond ...

of cyclododecene. : Ozonolyse des Cyclododecen

Biological process

Paraffin wax Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and begins to m ...

can be converted into DDDA on a laboratory scale with a special strain of ''

Candida tropicalis ''Candida tropicalis'' is a species of yeast in the genus '' Candida''. It is a common pathogen in neutropenic hosts, in whom it may spread through the bloodstream to peripheral organs. For invasive disease, treatments include amphotericin B, ec ...

'' yeast in a multi-step process. Renewable plant-oil feedstocks sourced from

switchgrass ''Panicum virgatum'', commonly known as switchgrass, is a perennial warm season bunchgrass native to North America, where it occurs naturally from 55°N latitude in Canada southwards into the United States and Mexico. Switchgrass is one of the ...

could also be used to produce DDDA.

Uses

DDDA os used in

antiseptics An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...

, top-grade coatings, painting materials, corrosion inhibitors,

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

s, and

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

s. It is one of two precursors to the

engineering plastic Engineering plastics are a group of plastic materials that have better mechanical and/or thermal properties than the more widely used commodity plastics (such as polystyrene, PVC, polypropylene and polyethylene). Being more expensive than sta ...

nylon Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from petro ...

612. The once commercial nylon called Qiana was produced on scale using DDDA.

Medical

In type 2 diabetic patients DDDA demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.

References

{{Navbox linear saturated dicarboxylic acids Dicarboxylic acids