1,5-Pentanediol

1,5-Pentanediol[1]
Names
IUPAC name
pentane-1,5-diol
Other names
Pentamethylene glycol
1,5-Dihydroxypentane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.505
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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored 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]

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. ↑ 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. ↑ Kaufman, D.; Reeve, W. (1946). "3-Methyl-2(5H)-furanone". Organic Syntheses. 26: 83. ; Collective Volume, 3, p. 693
  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. ↑ Associated Press (2007-11-09). "Mom: Chemical-laced toy made son 'drunk'". USA Today.
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