Pentaerythritol


Pentaerythritol
Pentaerythritol
Identifiers
CAS number 115-77-5 YesY
UNII SU420W1S6N YesY
Properties
Molecular formula C5H12O4
Molar mass 136.15
Appearance white solid
Density 1.396g/cm3
Melting point

260.5 °C

Boiling point

276 °C at 30 mmHg

Solubility in water 5.6 g/100 mL at 15°C
Hazards
Flash point 200.1°C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pentaerythritol is the organic compound with the formula C5H12O4. This white, crystalline polyol with the neopentane backbone is a versatile building block for the preparation of many polyfunctionalized compounds such as the explosive PETN and pentaerythritol tetraacrylate.[1] Derivatives of pentaerythritol are components of alkyd resins, varnishes, PVC stabilizers, tall oil esters, and olefin antioxidants.

Halogen-free pentaerythritol esters are also environmentally friendly alternative to conventional electrical transformer fluids, being both readily biodegradable and non-hazardous in water. They advantageously replace polychlorobiphenyl (PCB), and even silicone-based or fluorinated hydrocarbons, as dielectric fluid in transformers. Their low volatility and high flash point give them an excellent resistance to ignition in case of major electrical failure and transformer rupture.

Synthesis

Pentaerythritol can be prepared by condensation of acetaldehyde and formaldehyde in a basic environment (Tollens' reaction).[2] The process occurs by successive aldol reactions followed by a Cannizzaro reaction. Impurities include dipentaerythritol and tripentaerythritol.[3]

2 CH3CHO + 8 CH2O + Ca(OH)2 → 2 C(CH2OH)4 + (HCOO)2Ca

References

  1. ^ S. F. Marrian (1948). "The Chemical Reactions of Pentaerythritol and its Derivatives". Chemical Reviews 43 (1): 149–202. doi:10.1021/cr60134a004. PMID 18876970. 
  2. ^ H. B. J. Schurink (1941), "Pentaerythritol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0425 ; Coll. Vol. 1: 425 
  3. ^ M. S. Peters, J. A. Quinn (1955). "Pentaerythritol Production Yields". Industrial & Engineering Chemistry 47 (9): 1710–1713. doi:10.1021/ie50549a016. 

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Look at other dictionaries:

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  • pentaerythritol — [pen΄tə e rith′ri tôl΄, pen΄tə e rith′ritōl΄] n. [ PENTA + ERYTHRITOL] a colorless, crystalline compound, C(CH2OH) 4, prepared by reacting acetaldehyde with formaldehyde: used in the manufacture of alkyd resins, explosives, insecticides, etc …   English World dictionary

  • Pentaerythritol — Strukturformel Allgemeines Name Pentaerythrit Andere Namen Pentaerythritol 2,2 Bis(hydroxymethyl)1,3 propandiol …   Deutsch Wikipedia

  • pentaerythritol — pentaeritritolis statusas T sritis chemija formulė C(CH₂OH)₄ atitikmenys: angl. pentaerythritol rus. пентаэритрит ryšiai: sinonimas – 2,2 bis(hidroksimetil) 1,3 propandiolis …   Chemijos terminų aiškinamasis žodynas

  • pentaerythritol — /pen teuh i rith ri tawl , tol /, n. Chem. a white, crystalline, water soluble powder, C5H12O4, used chiefly in the manufacture of alkyd resins, varnishes, plasticizers, and explosives. [1890 95; PENTA + ERYTHRITOL] * * * …   Universalium

  • pentaerythritol — noun The polyhydric alcohol 2,2 bis(hydroxymethyl)1,3 propanediol C(CHOH) …   Wiktionary

  • pentaerythritol — The tetranitrate is a coronary vasodilator with action similar to that of other slow acting organic nitrates. * * * pen·ta·eryth·ri·tol .pent ə i rith rə .tȯl, .tōl n a crystalline alcohol C5H12O4 that is used chiefly in making synthetic resins …   Medical dictionary

  • pentaerythritol — n. chemical compound used to produce paints and explosives …   English contemporary dictionary

  • pentaerythritol — pen·ta·erythritol …   English syllables


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