1,5-Pentanediol

1,5-Pentanediol[1]
Names
	IUPAC name pentane-1,5-diol
	Other names Pentamethylene glycol; 1,5-Dihydroxypentane
Identifiers
CAS Number	111-29-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL448289 ;
ChemSpider	13839441 ;
ECHA InfoCard	100.003.505
PubChem CID	8105;
UNII	07UXZ0SCST ;
CompTox Dashboard (EPA)	DTXSID2041256 ;
	InChI InChI=1S/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 Key: ALQSHHUCVQOPAS-UHFFFAOYSA-N ; InChI=1/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 Key: ALQSHHUCVQOPAS-UHFFFAOYAE;
	SMILES OCCCCCO;
Properties
Chemical formula	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)
Solubility in water	Miscible
Hazards
NFPA 704 (fire diamond)	1 2 0
	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]

1,5-Pentanediol is produced by hydrogenation of glutaric acid and its derivatives.[3] It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol.[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.
Nakagawa, Yoshinao; Tomishige, Keiichi (2012). "Production of 1,5-Pentanediol from Biomass via Furfural and Tetrahydrofurfuryl Alcohol". Catalysis Today. 195: 136–143. doi:10.1016/j.cattod.2012.04.048.
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.
"Mom: Chemical-laced toy made son 'drunk'". USA Today. Associated Press. 2007-11-09.

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[1] 1,5-Pentanediol at Sigma-Aldrich

[2] Merck Index, 11th Edition, 7073.

[3] Werle, P.; Morawietz, M. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.

[4] Nakagawa, Yoshinao; Tomishige, Keiichi (2012). "Production of 1,5-Pentanediol from Biomass via Furfural and Tetrahydrofurfuryl Alcohol". Catalysis Today. 195: 136–143. doi:10.1016/j.cattod.2012.04.048.

[5] Wang, L. (2007-11-09). "Industrial Chemical Sullies Popular Children's Toy". Chemical & Engineering News.

[6] Griffiths, J. (2008). "Government and Society: Scientific sleuthing: how GC/MS uncovered toy danger". Analytical Chemistry. 80 (1): 6. doi:10.1021/ac085987i.

[7] "Mom: Chemical-laced toy made son 'drunk'". USA Today. Associated Press. 2007-11-09.