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1,5-Pentanediol

1,5-Dihydroxypentane | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0

1,5-Pentanediol is the organic compound with the formula HO(CH)OH. Like other diols, this viscous, colorless liquid is used as a plasticizer and also forms polyesters, which are used as emulsifying agents and resin intermediates.

Synthesis and reactions

1,5-Pentanediol is produced by hydrogenation of glutaric acid and its derivatives. It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol. 1,4-Pentadiene can be prepared from 1,5-pentadiol via the diacetate.

Contamination of Bindeez

A toy called Bindeez (Aqua Dots in North America) was recalled by the distributor in November 2007 due to the unauthorized substitution of 1,5-pentanediol with 1,4-butanediol. The toy consists of small beads that stick to each other when sprinkled with water. 1,4-Butanediol, which when ingested is metabolized to gamma-hydroxybutyric acid, was detected by GC-MS.{{cite news | url = https://pubs.acs.org/cen/news/85/i46/8546news11.html | newspaper = Chemical & Engineering News | title = Industrial Chemical Sullies Popular Children's Toy | author = Wang, L. | date = 2007-11-09 }} ChemNet China lists the price of 1,4-butanediol at between US$1,350–2,800/tonne, while the price for 1,5-pentanediol is about US$9,700/tonne.

References

References

  1. [https://www.sigmaaldrich.com/US/en/product/aldrich/p7703 1,5-Pentanediol] at [[Sigma-Aldrich]]
  2. "1,5-Pentanediol".
  3. ''Merck Index'', 11th Edition, '''7073'''.
  4. Werle, P.. "Alcohols, Polyhydric".
  5. Nakagawa, Yoshinao. (2012). "Production of 1,5-Pentanediol from Biomass via Furfural and Tetrahydrofurfuryl Alcohol". Catalysis Today.
  6. R. E. Benson, B. C. McKusick, Oliver Grummitt, E. P. Budewitz, C. C. Chudd. (1958). "1,4-Pentadiene". Organic Syntheses.
  7. Griffiths, J.. (2008). "Government and Society: Scientific sleuthing: how GC/MS uncovered toy danger". Analytical Chemistry.
  8. (2007-11-09). "Mom: Chemical-laced toy made son 'drunk'". [[USA Today]].
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