1,5-Pentanediol

1,5-Pentanediol[1]
Names
Preferred IUPAC name
Pentane-1,5-diol
Other names
Pentamethylene glycol
1,5-Dihydroxypentane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.505 Edit this at Wikidata
EC Number
  • 203-854-4
UNII
  • InChI=1S/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 checkY
    Key: ALQSHHUCVQOPAS-UHFFFAOYSA-N checkY
  • InChI=1/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2
    Key: ALQSHHUCVQOPAS-UHFFFAOYAE
  • OCCCCCO
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
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H302
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,5-Pentanediol is the organic compound with the formula HO(CH2)5OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.[3]

Synthesis and reactions

1,5-Pentanediol is produced by hydrogenation of glutaric acid and its derivatives.[4] It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol.[5] 1,4-Pentadiene can be prepared from 1,5-pentadiol via the diacetate.[6]

Contamination of Bindeez

See also: 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.[7][8] 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.[9]

References

  1. ^ 1,5-Pentanediol at Sigma-Aldrich
  2. ^ "1,5-Pentanediol". pubchem.ncbi.nlm.nih.gov.
  3. ^ Merck Index, 11th Edition, 7073.
  4. ^ Werle, P.; Morawietz, M. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305. ISBN 978-3527306732.
  5. ^ 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.
  6. ^ R. E. Benson, B. C. McKusick, Oliver Grummitt, E. P. Budewitz, C. C. Chudd (1958). "1,4-Pentadiene". Organic Syntheses. 38: 78. doi:10.15227/orgsyn.038.0078.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Wang, L. (2007-11-09). "Industrial Chemical Sullies Popular Children's Toy". Chemical & Engineering News.
  8. ^ Griffiths, J. (2008). "Government and Society: Scientific sleuthing: how GC/MS uncovered toy danger". Analytical Chemistry. 80 (1): 6. doi:10.1021/ac085987i.
  9. ^ "Mom: Chemical-laced toy made son 'drunk'". USA Today. Associated Press. 2007-11-09.