1,5-Pentanediol

Last updated
1,5-Pentanediol [1]
Pentanediol.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-854-4
PubChem CID
UNII
  • InChI=1S/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 Yes check.svgY
    Key: ALQSHHUCVQOPAS-UHFFFAOYSA-N Yes check.svgY
  • 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]
GHS-pictogram-exclam.svg
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.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

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]

Related Research Articles

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In organic chemistry, a diene ; also diolefin, dy-OH-lə-fin) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alkene units, with the standard prefix di of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

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<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

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gamma-Butyrolactone Chemical compound

Gamma-butyrolactone (GBL) or γ-butyrolactone is a hygroscopic, colorless, water-miscible liquid with a weak, characteristic odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.

<span class="mw-page-title-main">Wacker process</span> Chemical reaction

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<span class="mw-page-title-main">Glutaric acid</span> Chemical compound

Glutaric acid is the organic compound with the formula C3H6(COOH)2. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

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<span class="mw-page-title-main">1,4-Butynediol</span> Chemical compound

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<span class="mw-page-title-main">1,2-Butanediol</span> Chemical compound

1,2-Butanediol is the organic compound with the formula HOCH2(HO)CHCH2CH3. It is classified as a vic-diol (glycol). It is chiral, although typically it is encountered as the racemic mixture. It is a colorless liquid.

1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a colorless water-soluble solid.

<span class="mw-page-title-main">Tetrahydrofurfuryl alcohol</span> Chemical compound

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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.