Dodecanedioic acid

Dodecanedioic acid
Names
	IUPAC name Dodecanedioic acid
	Other names DDDA
Identifiers
CAS Number	693-23-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4676 ;
ChemSpider	12213 ;
ECHA InfoCard	100.010.680
KEGG	C02678 ;
PubChem CID	12736;
UNII	978YU42Q6I ;
CompTox Dashboard (EPA)	DTXSID3027297 ;
	InChI 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) Key: TVIDDXQYHWJXFK-UHFFFAOYSA-N ; 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;
	SMILES O=C(O)CCCCCCCCCCC(=O)O;
Properties
Chemical formula	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)
Solubility in water	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.
"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.

[1] Nylon#Homopolymers

[2] 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.

[:0-3] "BIOLON® DDDA". verdezyne.com. Archived from the original on 2016-09-24. Retrieved 2016-09-23.

[Weissermel-4] Klaus Weissermel, Hans-Jurgen Arpe (1997). Industrial Organic Chemistry (3rd ed.). John Wiley & Sons. ISBN 3-527-28838-4.

[5] "Dibasic acids". www.cathaybiotech.com. Retrieved 2019-03-15.

[6] 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.