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
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 ?)
Infobox references

1,5-Pentanediol is the organic compound with the formula HO(CH2)5OH. 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.[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 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.[7][8] 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.[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 978-3-527-30673-2.
  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.
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