1,10-Decanediol
Chemical compound
From Wikipedia, the free encyclopedia
1,10-Decanediol is an organic compound diol with the chemical formula (HOCH2(CH2)8CH2OH. It is a white solid with limited solubility in water.[1][3] The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.[4]
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
Decane-1,10-diol | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.003.614 |
| EC Number |
|
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C10H22O2 | |
| Molar mass | 174.284 g·mol−1 |
| Appearance | White solid[1] |
| Density | 0.891 g·cm−3 (80 °C)[1] |
| Melting point | 72–75 °C[1] 81.7 °C[2] Heat of fusion = 44.0 kJ·mol−1 (252.6 J·g−1).[2] |
| Boiling point | 297 °C (1013 hPa)[1] 170 °C (11 hPa)[1] |
| Poorly soluble[3] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Preparation
It is traditionally synthesized by reduction of diesters of sebacic acid, which are readily obtained from natural sources. One method is the Bouveault-Blanc reduction.[5]
Other more specialized reagents have been used such as sodium borohydride/cerium(III) chloride.[6] The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-decanediol.[7]
Other sebacic acid precursor have been used such as diethyl dithiosebacate with tetrabutylammonium borohydride[8] and sebacic acid itself and diisopropyltitanium(III) borohydride.[9]
Reactions
The bromination of 1,10-decanediol yields 1,10-dibromodecane,[10] whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.[11] The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile.[12]
Uses
Pyrolysis of poly(1,10-decylenecarbonate), the polycarbonate derived from 1,10-decanediol, gives 9-decenol as described by the following idealized equation:[13]
- (OCH2(CH2)8CH2O)CO → 2 CH2=CH(CH2)7CH2OH + CO2
1,10-Decanediol, along with its isomers 1,9-decanediol and 1,2-decanediol, functions as an inhibitor of soil nitrification.[14] This inhibition can mitigate nitrogen loss from soil and prevent the environmental issues associated with nitrification in agricultural settings.[14] Furthermore, these diols exhibit a significant inhibitory effect on nitrite-forming microorganisms, even at low concentrations.[14]