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.Boy Cornils, Peter Lappe "Dicarbox ...

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-CH=CH2. 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 ...

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. The triene is then hydrogenated to cyclododecane.

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 orthoborate, trihydroxidoboron or boracic acid. It is usually encountered as colorless crystals or a white ...

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. Like its smaller analogs but unlike the larger ones, it has a camphor-like odor. History and synthesis It ...

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

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

. An alternative route involves

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...

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 melting poi ...

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, ech ...

'' 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 55th parallel north, 55°N latitude in Canada southwards into the United States and Mexico. Switch ...

could also be used to produce DDDA.

Uses

DDDA is used in

antiseptics An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abili ...

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

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

s, and

polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

s. It is one of two precursors to the

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

nylon Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieti ...

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

ethylene glycol Ethylene glycol ( IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...

is a

synthetic musk Synthetic musks are a class of synthetic aroma compounds to emulate the scent of deer musk and other animal musks (castoreum and civet). Synthetic musks have a clean, smooth and sweet scent lacking the fecal notes of animal musks. They are used as ...

of the macrocyclic lactones group commercially marketed as "Arova 16".

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