Dodecanedioic acid

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title: "Dodecanedioic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["dicarboxylic-acids"] topic_path: "general/dicarboxylic-acids" source: "https://en.wikipedia.org/wiki/Dodecanedioic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 455206624 | ImageFile = Dodecanedioic acid structure.svg | ImageSize = 250px | PIN = Dodecanedioic acid | SystematicName = Dodecanedioic acid | OtherNames = DDDA DC12 1,10-Decanedicarboxylic acid Decamethylenedicarboxylic acid 1,10-dicarboxydecane | Section1 = {{Chembox Identifiers | KEGG_Ref = | KEGG = C02678 | InChIKey = TVIDDXQYHWJXFK-UHFFFAOYAC | StdInChI_Ref = | StdInChI = 1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) | StdInChIKey_Ref = | StdInChIKey = TVIDDXQYHWJXFK-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 693-23-2 | UNII_Ref = | UNII = 978YU42Q6I | PubChem = 12736 | ChemSpiderID_Ref = | ChemSpiderID = 12213 | ChEBI_Ref = | ChEBI = 4676 | SMILES = O=C(O)CCCCCCCCCCC(=O)O | InChI = 1/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16) | Section2 = {{Chembox Properties | C=12 | H=22 | O=4 | Appearance = White flakes | Density = 1.066 g/cm3 | MeltingPtC = 127-129 | MeltingPt_notes = | BoilingPtC = 245 | Solubility = pH dependent | Section3 = {{Chembox Hazards | MainHazards = | FlashPtC = 220 | AutoignitionPtC =

Dodecanedioic acid (DDDA) is a dicarboxylic acid 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 using a multi-step chemical process. Butadiene is first converted to cyclododecatriene through cyclotrimerization. The triene is then hydrogenated to cyclododecane. Autoxidation by air in the presence of boric acid gives a mixture of cyclodecanol and the cyclododecanone. In the final step, this mixture oxidized to the diacid using nitric acid. An alternative route involves ozonolysis of cyclododecene. :[[File:Ozonolyse des Cyclododecen.svg|Ozonolysis of cyclododecene to dodecanedioic acid.]]

Biological process

Paraffin wax can be converted into DDDA on a laboratory scale with a special strain of Candida tropicalis yeast in a multi-step process. Renewable plant-oil feedstocks sourced from switchgrass could also be used to produce DDDA.

Uses

DDDA is used in antiseptics, top-grade coatings, painting materials, corrosion inhibitors, surfactants, and polymers. It is one of two precursors to the engineering plastic nylon 612. The once commercial nylon called Qiana was produced on scale using DDDA. DDDA ester with ethylene glycol is a synthetic musk 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.{{Cite journal | pmid = 9591306 | year = 1998 | last1 = Greco | first1 = A. V. | title = The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients | journal = Nutrition | volume = 14 | issue = 4 | pages = 351–7 | last2 = Mingrone | first2 = G | last3 = Capristo | first3 = E | last4 = Benedetti | first4 = G | last5 = De Gaetano | first5 = A | last6 = Gasbarrini | first6 = G | doi=10.1016/s0899-9007(97)00502-9

References

References

  1. "BIOLON® DDDA".
  2. Klaus Weissermel, Hans-Jurgen Arpe. (1997). "Industrial Organic Chemistry". John Wiley & Sons.
  3. (2014). "Ullmann's Encyclopedia of Industrial Chemistry".
  4. "Dibasic acids".
  5. "Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids". American Oil Chemists Society.
  6. [[Nylon#Homopolymers]]

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dicarboxylic-acids