Acetaldehyde → Formate

HRID 713535Notes

Reaction equation

HRID 713535 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].C=O.[CH:12](=[O:14])C.[OH-].[Na+].[OH:17]CC(CO)(CO)C=O>C1C=CC=CC=1.CCOCC.ClC(Cl)(Cl)Cl.O>[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[CH:12]([O-:14])=[O:17]

Participants

11

Reactant 5

HCID 177Acetaldehyde3×HCID 712Formaldehyde4×HCID 8285Pentaerythritol3×HCID 14798Sodium HydroxideHCID 77434Propanal, 3-hydroxy-2,2-bis(hydroxymethyl)-

Product 2

HCID 283FormateHCID 8285Pentaerythritol

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

Pentaerythritol[2,2-bis(hydroxymethyl)-1,3-propane diol, Penta, PE] is a white, crystalline powder with a sweet taste and is neither hygroscopic nor inflammable, density 1.399, melting point 262° C. and boiling point 276° C. (40 hPa). Pentaerythritol is highly soluble in boiling water, is poorly soluble in alcohol, and insoluble in benzene, tetrachloromethane, ether, petroleum ether. Pentaerythritol is manufactured industrially by reacting formaldehyde with acetaldehyde in an aqueous solution of Ca(OH)2 or NaOH at 15-45° C. The reaction takes place initially as an aldol reaction, whereby the formaldehyde reacts as the carbonyl component and the acetaldehyde as the methylene component. Due to the high carbonyl activity of the formaldehyde, the reaction of acetaldehyde with itself hardly occurs. Finally, the tris(hydroxymethyl)acetaldehyde undergoes a crossed Cannizzaro reaction with formaldehyde to afford pentaerythritol and formate.

Workup

  1. customat 15-45° C

Sources & evidence

ORD record
ord-9c0e3bd923cd4376bfa198bcd33e2c42
Source dataset
uspto-grants-2015_11
Patent number
US09181516B2

Reaction notes

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