Dodecanedioic acid
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Names | |
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Preferred IUPAC name
Dodecanedioic acid | |
Other names
DDDA
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Identifiers | |
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3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.010.680 ![]() |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 | |
Dodecanedioic acid (DDDA) is a dicarboxylic acid mainly used in antiseptics, top-grade coatings, painting materials, corrosion inhibitors, surfactants, and engineering plastics such as nylon 612.[1]
Experimental work with dodecanedioic acid in type 2 diabetic patients has demonstrated that IV infusion helps to maintain normal blood sugar and energy levels without increasing the blood glucose load in the process.[2]
Production[]
DDDA is currently produced by both chemical and biological routes.
Chemical process[]
It has traditionally been produced from butadiene using a multi-step chemical process.[3] Butadiene is first converted to cyclododecatriene through a cyclotrimerization process.[4]
Cyclododecatriene (1) is converted to dodecanedioic acid (4) by hydrogenation to cyclododecane (2) followed by air oxidation in the presence of boric acid at elevated temperatures to a mixture of the alcohol (3a) and the ketone (3b). In the final step, this mixture oxidized further by nitric acid.
Biological process[]
Paraffin wax can be converted into DDDA[5] with a special strain of Candida tropicalis yeast in a multi-step process.[6] Renewable plant-oil feedstocks sourced from switchgrass can also be used to produce DDDA.[3]
References[]
- ^ Nylon#Homopolymers
- ^ 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.
- ^ a b "BIOLON® DDDA". verdezyne.com. Archived from the original on 2016-09-24. Retrieved 2016-09-23.
- ^ Klaus Weissermel, Hans-Jurgen Arpe (1997). Industrial Organic Chemistry (3rd ed.). John Wiley & Sons. ISBN 3-527-28838-4.
- ^ "Dibasic acids". www.cathaybiotech.com. Retrieved 2019-03-15.
- ^ 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.
- Dicarboxylic acids