1,5-Pentanediol
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Names | |
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IUPAC name
pentane-1,5-diol | |
Other names
Pentamethylene glycol 1,5-Dihydroxypentane | |
Identifiers | |
3D model (JSmol) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.505 |
PubChem CID |
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Properties | |
C5H12O2 | |
Molar mass | 104.14758 |
Density | 0.994 g/mL at 25 °C |
Melting point | −18 °C (0 °F; 255 K) |
Boiling point | 242 °C (468 °F; 515 K) |
Miscible | |
Hazards | |
NFPA 704 | |
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 | |
1,5-Pentanediol is the organic compound with the formula HOCH2CH2CH2CH2CH2OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.[2]
Preparation
1,5-Pentanediol is manufactured by hydrogenation of glutaric acid and its derivatives.[3] It can also be prepared by hydrogenation of furfural followed by hydrogenolysis of the substituted tetrahydrofuran.[4]
Contamination of Bindeez
A toy called Bindeez (Aqua Dots in North America) was recalled by the distributor in November 2007 because of the unauthorized substitution of 1,5-pentanediol with 1,4-butanediol. The toy consists of small beads that stick to each other upon sprinkling with water. 1,4-Butanediol, which when ingested is metabolized to gamma-hydroxybutyric acid, was detected by GC-MS.[5][6] ChemNet China lists the price of 1,4-butanediol at between about US$1,350–2,800/tonne, while the price for 1,5-pentanediol is about US$9,700/tonne.[7]
References
- ↑ 1,5-Pentanediol at Sigma-Aldrich
- ↑ Merck Index, 11th Edition, 7073.
- ↑ Werle, P.; Morawietz, M., "Alcohols, Polyhydric", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_305
- ↑ Kaufman, D.; Reeve, W. (1946). "3-Methyl-2(5H)-furanone". Organic Syntheses. 26: 83. ; Collective Volume, 3, p. 693
- ↑ Wang, L. (2007-11-09). "Industrial Chemical Sullies Popular Children's Toy". Chemical & Engineering News.
- ↑ Griffiths, J. (2008). "Government and Society: Scientific sleuthing: how GC/MS uncovered toy danger". Analytical Chemistry. 80 (1): 6. doi:10.1021/ac085987i.
- ↑ Associated Press (2007-11-09). "Mom: Chemical-laced toy made son 'drunk'". USA Today.