Pentaerythritol

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Pentaerythritol
Names
IUPAC name
2,2-Bis(hydroxymethyl)1,3-propanediol
Systematic IUPAC name
Pentaerythritol
Other names
Tetramethylolmethane
Hercules Aqualon
Hercules P 6
Monopentaerythritol
Pentaerythrite
Pentek
PETP
THME
Identifiers
Jmol-3D images Image
Properties
C5H12O4
Molar mass 136.15
Appearance White crystalline solid
Odor None
Density 1.396 g/cm3
Melting point 260.5 °C (500.9 °F; 533.6 K)
Boiling point 276 °C (529 °F; 549 K)
5.6 g/100 mL (15 °C)
Solubility soluble in ethanol, ethylene glycol, formamide, glycerol, methanol
insoluble in acetone, benzene, CCl4, diethyl ether, paraffin, toluene
Vapor pressure 0.00000008 mmHg (20°C)
Hazards
Safety data sheet FischerSci
Flash point 200.1 °C
Lethal dose or concentration (LD, LC):
10,000 mg/kg (rat, oral)
50,000 mg/L (freshwater fish, 48 h)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pentaerythritol (sometimes shortened to PE) is an organic compound with the formula C5H12O4, a polyol with the neopentane backbone. It has no relation to erythritol.

Properties

Chemical

Pentaerythritol can react with with various halogenated organic compounds to yield many ethers or esters. It can also react with benzaldehyde.

Physical

PE is a white crystalline solid, with no smell (if pure). It has a density of 1.396g/cm3. PE is slightly soluble in water (5.6 g/100 ml at 15 °C). It is also soluble in ethanol, ethylene glycol, formamide, glycerol, methanol, but insoluble in aprotic organic solvents such as acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, paraffin.

Availability

Pentaerythritol is sold by chemical suppliers. Some products may contain traces of borax as additive.

Certain cosmetics contain a small amount of PE or its derivates.

Preparation

Pentaerythritol can be made by reacting formaldehyde with acetaldehyde, in the presence of a strong base, such as sodium hydroxide, though calcium hydroxide can also be used. A full recipe can be found here.

Acetaldehyde can be replaced with lactonitrile.[1]

Reacting formaldehyde with 3-hydroxybutanal in the presence of lead(II) hydroxide also yields pentaerythritol.[2][3]

It can also be prepared from propylene oxyide.[4]

Projects

Handling

Safety

Pentaerythritol is irritant to skin, eyes, nose and mouth. It presents some toxicity if ingested.[5]

Storage

Pentaerythritol should be stored in closed bottles, away from any flame source or oxidizer. Just about any clean bottle is suitable.

Disposal

Pentaerythritol can be safely burned as it releases no toxic byproducts.

References

  1. http://www.google.com/patents/US2711431
  2. Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), vol. 45, p. 1452
  3. Chemisches Zentralblatt (1914), vol. 85, nb. I, p. 758
  4. https://www.google.gg/patents/US20120016049
  5. http://www.sciencelab.com/msds.php?msdsId=9926416

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