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;
	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	230.30 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).
	verify (what is ?)
	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

Synthetic production

DDDA is typically produced through two methods. 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.

Biotech production

A biotechnology is used to convert paraffin wax into DDDA with a special strain of Candida tropicalis yeast in a multi-step process.^[5] Verdezyne has created a method to use plant-oil sourced feedstocks, which makes it the only producer using renewable feedstocks for DDDA.^[3]

References

↑ "Nylon-6,12".
↑ 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.
1 2 "BIOLON® DDDA". verdezyne.com. Retrieved 2016-09-23.
↑ Klaus Weissermel, Hans-Jurgen Arpe (1997). Industrial Organic Chemistry (3rd ed.). John Wiley & Sons. ISBN 3-527-28838-4.
↑ "Products". www.hilead-europe.com. Retrieved 2016-09-23.

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[1] "Nylon-6,12".

[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] 1 2 "BIOLON® DDDA". verdezyne.com. 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] "Products". www.hilead-europe.com. Retrieved 2016-09-23.