Docosanedioic acid: Difference between revisions
move PIN |
|||
| (One intermediate revision by one other user not shown) | |||
| Line 28: | Line 28: | ||
| Density = 0.972 g/cm<sup>3</sup> |
| Density = 0.972 g/cm<sup>3</sup> |
||
| MeltingPtC = 119-125 |
| MeltingPtC = 119-125 |
||
| |
| MeltingPt_ref = <ref>{{Cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/306673 | title = Docosanedioic acid }}</ref> |
||
| BoilingPtC = 527 |
| BoilingPtC = 527 |
||
| Solubility = Insoluble in water |
| Solubility = Insoluble in water |
||
| Line 53: | Line 53: | ||
== References == |
== References == |
||
{{Reflist}} |
{{Reflist}} |
||
{{Navbox linear saturated dicarboxylic acids}} |
|||
[[Category:Dicarboxylic acids]] |
[[Category:Dicarboxylic acids]] |
||
Latest revision as of 01:15, 22 July 2022
| |
| Names | |
|---|---|
| Preferred IUPAC name
Docosanedioic acid | |
| Other names
Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.127.871 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C22H42O4 | |
| Molar mass | 370.574 g·mol−1 |
| Appearance | White solid |
| Density | 0.972 g/cm3 |
| Melting point | 119–125 °C (246–257 °F; 392–398 K)[1] |
| Boiling point | 527 °C (981 °F; 800 K) |
| Insoluble in water | |
| Hazards | |
| Flash point | 286.6 °C (547.9 °F; 559.8 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH
2)
20COOH.
Uses
[edit]Docosanedioic acid finds uses in organic chemistry and is a starting material for ultrasound contrast agents. It is also used to produce the fluffy white solid 1,22-docosanediol, which in turn is a precursor to 1,22-bis-2-(trimethylammonium)ethylphospatyldocosane, a phosphocholine derivative with antifungal activity.
Synthesis
[edit]Disodium 7,16-diketodocosanedioate is reacted with triethanolamine, hydrazine hydrate, potassium hydroxide and a little hydrochloric acid to afford docosanedioic acid via a Wolff–Kishner reduction.[clarification needed]
Alternately, 2,5-bis(ω-carboyoctyl)thiophene is desulfurized with Raney nickel to afford docosanedioic acid.
It can also be produced through oxidative coupling of 10-undecynoic acid to docosa-10,12-diynedoic acid and reduction of this intermediate with a palladium catalyst.