Dodecanedioic acid

Dodecanedioic acid (DDDA) is a dicarboxylic acid with the formula (CH2)10(CO2H)2. 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.

Dodecanedioic acid
Names
Preferred IUPAC name
Dodecanedioic acid
Other names
DDDA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.680
KEGG
UNII
  • InChI=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) checkY
    Key: TVIDDXQYHWJXFK-UHFFFAOYSA-N checkY
  • 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)
    Key: TVIDDXQYHWJXFK-UHFFFAOYAC
  • O=C(O)CCCCCCCCCCC(=O)O
Properties
C12H22O4
Molar mass 230.304 g·mol−1
Appearance White flakes
Density 1.066 g/cm3
Melting point 127–129 °C (261–264 °F; 400–402 K)
Boiling point 245 °C (473 °F; 518 K)
pH dependent
Hazards
Flash point 220 °C (428 °F; 493 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Production

DDDA has traditionally been produced from butadiene using a multi-step chemical process.[1] Butadiene is first converted to cyclododecatriene through cyclotrimerization.[2] 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.[3]

Ozonolysis of cyclododecene to dodecanedioic acid.

Biological process

Paraffin wax can be converted into DDDA on a laboratory scale[4] with a special strain of Candida tropicalis yeast in a multi-step process.[5] Renewable plant-oil feedstocks sourced from switchgrass could also be used to produce DDDA.[1]

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.[6] 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.[7]

References
  1. "BIOLON® DDDA". verdezyne.com. Archived from the original on 2016-09-24. Retrieved 2016-09-23.
  2. Klaus Weissermel, Hans-Jurgen Arpe (1997). Industrial Organic Chemistry (3rd ed.). John Wiley & Sons. ISBN 3-527-28838-4.
  3. Cornils, Boy; Lappe, Peter; By Staff, Updated (2014). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–18. doi:10.1002/14356007.a08_523.pub3. ISBN 9783527306732.
  4. "Dibasic acids". www.cathaybiotech.com. Retrieved 2019-03-15.
  5. Kroha, Kyle. "Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids" (PDF). Inform. American Oil Chemists Society. 15(9) (Sep 2004): 568. Archived from the original (PDF) on 6 October 2014. Retrieved 15 March 2019.
  6. Nylon#Homopolymers
  7. Greco, A. V.; Mingrone, G; Capristo, E; Benedetti, G; De Gaetano, A; Gasbarrini, G (1998). "The metabolic effect of dodecanedioic acid infusion in non-insulin-dependent diabetic patients". Nutrition. 14 (4): 351–7. doi:10.1016/s0899-9007(97)00502-9. PMID 9591306.
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