Pentaerythritol

Structure:
Molecular formula: C₅H₁₂O₄
Molar mass: 136.15
IUPAC Name: 2,2-bis(hydroxymethyl)propane-1,3-diol
H bond acceptors: 4
H bond donors: 4
Freely Rotating Bonds: 8
Polar Surface Area: 36.92 Å²
Index of Refraction: 1.531
Molar Refractivity: 31.31 cm³
Molar Volume: 101.1 cm³
Surface Tension: 70.5 dyne/cm
Density: 1.346 g/cm³
Flash Point: 200.1 °C
Enthalpy of Vaporization: 72.71 kJ/mol
Boiling Point: 380.4 °C at 760 mmHg
Vapour Pressure: 2.38E-07 mmHg at 25°C
Appearance: white solid
Melting point: 260.5 °C
Solubility in water: 5.6 g/100 mL at 15 °C
EINECS: 204-104-9
Water Solubility: 1 g/18 mL (15 ºC)
Sensitive: Hygroscopic
Merck: 14,7111
BRN: 1679274
InChI
InChI=1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
Smiles
C(CO)(CO)(CO)CO
Stability: Stable. Incompatible with strong acids, strong oxidizing agents, acid chlorides, acid anhydrides. Combustible
Product Categories: Inorganic & organic chemicals; Organics
Synonyms: 2,2-Bis(hydroxymethyl)propane-1,3-diol ; 2,2-Bis(hydroxymethyl)-1,3-propanediol ; tetramethylolmethane ; 1,1,1-Tris(hydroxymethyl)ethanol ; 1,3-Propanediol,2,2-bis(hydroxymethyl)- ; 2,2-bis(hydroxymethyl)-3-propanediol ; 3-Propanediol,2,2-bis(hydroxymethyl)-1 ; Auxenutril

 Pentaerythritol (CAS NO.115-77-5) is manufactured by reaction of formaldehyde and acetaldehyde in the presence of a basic catalyst, generally an alkali or alkaline-earth hydroxide.

 In the process (Fig. 1), the main concern in mixing is to avoid loss of temperature control in this exothermic reaction, which can load to excessive by-product formation and/or reduced yields of pentaerythritol. The reaction time depends on the reaction temperature and may vary from about 0.5 to 4 hours at final temperatures of about 65 and 35 °C, respectively. The reactor product, neutralized with acetic or formic acid, is then stripped of excess formaldehyde and water to produce a highly concentrated solution of pentaerythritol reaction products. This is then cooled under carefully controlled crystallization conditions so that the crystals can be readily separated from the liquors by subsequent filtration.

 Staged reactions, where only part of the initial reactants is added, either to consecutive reactors or with a time lag to the same reactor, may be used to reduce dipentaerythritol content. This technique increases the effective formaldehyde-to-acetaldehyde mole ratio, maintaining the original stoichiometric one. It also permits easier thermal control of the reaction. Both batch and continuous reaction systems are used.

 Dipentaerythritol and tripentaerythritol are obtained as by-products of the pentaerythritol process and may be further purified by fractional crystallization or extraction.

FIGURE 1 Manufacture of pentaerythritol.

Risk Statements: 33
R33:Danger of cumulative effects.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: RZ2490000
HS Code: 29054200

 Pentaerythritol (CAS NO.115-77-5) is the organic compound with the formula C(CH₂OH)₄. It belongs to the class of polyhydric alcohols or polyols. And it is moderately soluble in water. Pentaerythritol (CAS NO.115-77-5) is a versatile building block for the preparation of many polyfunctionalized compounds such as the explosive PETN and pentaerythritol triacrylate. Derivatives of pentaerythritol are components of alkyd resins, varnishes, PVC stabilizers, tall oil esters and olefin antioxidants.