Tetradecanedioic acid

Tetradecanedioic acid
Names
	Other names Tetradecane-1,14-dioic acid
Identifiers
CAS Number	821-38-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:76308;
ChemSpider	12630;
ECHA InfoCard	100.011.342
EC Number	212-476-9;
PubChem CID	13185;
UNII	UEC3AC47H1;
CompTox Dashboard (EPA)	DTXSID5061166 ;
	InChI InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18) Key: HQHCYKULIHKCEB-UHFFFAOYSA-N;
	SMILES C(CCCCCCC(=O)O)CCCCCC(=O)O;
Properties
Chemical formula	C14H26O4
Molar mass	258.358 g·mol−1
Density	1.04 g/cm3
Melting point	127 °C (261 °F; 400 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H315, H318, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetradecanedioic acid is an organic compound with the formula (CH₂)₁₂(CO₂H)₂. It is a colorless solid. As a 14-carbon dicarboxylic acid, it is a potential precursor to polyesters.^[1]

The compound is of historic interest in the context of the Leopold Ružička's synthesis of large ring ketones. It was first prepared by hydrolysis of the dinitrile (CH₂)₁₂(CN)₂, which was in turn obtained from 1,12-dibromododecane.^[2] It was subsequently synthesized from dihydroresorcinol (1,3-cyclohexanedione).^[3]

References

^ Sullivan, Kevin P.; Werner, Allison Z.; Ramirez, Kelsey J.; Ellis, Lucas D.; Bussard, Jeremy R.; Black, Brenna A.; Brandner, David G.; Bratti, Felicia; Buss, Bonnie L.; Dong, Xueming; Haugen, Stefan J.; Ingraham, Morgan A.; Konev, Mikhail O.; Michener, William E.; Miscall, Joel; Pardo, Isabel; Woodworth, Sean P.; Guss, Adam M.; Román-Leshkov, Yuriy; Stahl, Shannon S.; Beckham, Gregg T. (2022). "Mixed plastics waste valorization through tandem chemical oxidation and biological funneling". Science. 378 (6616): 207–211. doi:10.1126/science.abo4626. OSTI 1900007. PMID 36227984.
^ Chuit, Philippe (1926). "Préparation d'acides polyméthylène-dicarboniques de 11 à 19 atomes de carbone et de quelques-uns de leurs dérivés". Helvetica Chimica Acta. 9: 264–278. doi:10.1002/hlca.19260090131.
^ Stetter, Hermann; Dierichs, Wolfgang (1953). "Eine neue Methode zur Darstellung langkettiger Carbonsäuren, V. Mitteil.: Darstellung einiger langkettiger Dicarbonsäuren". Chemische Berichte. 86 (6): 693–696. doi:10.1002/cber.19530860606.

[1] Sullivan, Kevin P.; Werner, Allison Z.; Ramirez, Kelsey J.; Ellis, Lucas D.; Bussard, Jeremy R.; Black, Brenna A.; Brandner, David G.; Bratti, Felicia; Buss, Bonnie L.; Dong, Xueming; Haugen, Stefan J.; Ingraham, Morgan A.; Konev, Mikhail O.; Michener, William E.; Miscall, Joel; Pardo, Isabel; Woodworth, Sean P.; Guss, Adam M.; Román-Leshkov, Yuriy; Stahl, Shannon S.; Beckham, Gregg T. (2022). "Mixed plastics waste valorization through tandem chemical oxidation and biological funneling". Science. 378 (6616): 207–211. doi:10.1126/science.abo4626. OSTI 1900007. PMID 36227984.

[2] Chuit, Philippe (1926). "Préparation d'acides polyméthylène-dicarboniques de 11 à 19 atomes de carbone et de quelques-uns de leurs dérivés". Helvetica Chimica Acta. 9: 264–278. doi:10.1002/hlca.19260090131.

[3] Stetter, Hermann; Dierichs, Wolfgang (1953). "Eine neue Methode zur Darstellung langkettiger Carbonsäuren, V. Mitteil.: Darstellung einiger langkettiger Dicarbonsäuren". Chemische Berichte. 86 (6): 693–696. doi:10.1002/cber.19530860606.

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