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Benzyl Benzoate: Benzaldehyde and Sodium Benzylate
Benzyl benzoate is an oily ester that dissolves PVC when hot and softens it. Kamm (Organic Syntheses, 1921): a little sodium dissolved in benzyl alcohol turns two molecules of benzaldehyde into one of benzyl benzoate. Keep it below 50 to 60 °C as it mixes, or it overheats into benzyl ether. 454 g of benzaldehyde give 410 to 420 g. Sodium metal burns in water: keep it dry.
The picture: our own drawing.
Advanced
1 day
Instructions
1
1
Dissolve the sodium in benzyl alcohol
Dissolve the sodium in benzyl alcohol
Goggles and gloves on. Warm 3 g of sodium in 70 g of pure benzyl alcohol for half an hour until it dissolves. Let it cool to room temperature.
Tools needed:
Sodium
Benzyl Alcohol
Round-Bottom Flask
Large Pot (lower, for water bath)
Balance Scale
Rubber Gloves
Chemical Splash Goggles2
2
Add it to the benzaldehyde, cool
Add it to the benzaldehyde, cool
Add the solution little by little to 454 g of benzaldehyde, mixing well. Cool if needed to keep it just below 50 to 60 °C. It sets to a pasty jelly.
Materials for this step:
Benzaldehyde454 gTools needed:
Round-Bottom Flask
ThermometerLarge Pot (lower, for water bath)3
3
Warm on the water bath
Warm on the water bath
When the temperature stops rising, after about half an hour, warm it on the water bath for one to two hours, shaking now and then.
Tools needed:
Large Pot (lower, for water bath)Round-Bottom Flask4
4
Wash
Wash
Cool, add 200 ml of water and separate the oil. Wash it once more with water.
Tools needed:
Water
Separating Funnel5
5
Distil under vacuum
Distil under vacuum
Distil under vacuum. Benzyl alcohol, leftover aldehyde and water come first. When the temperature jumps, change the receiver: benzyl benzoate boils at 184 to 185 °C at 15 mm. Expect 410 to 420 g.
Tools needed:
Glass Distillation Flask
Condenser Coil
Vacuum PumpThermometer
Glass Bottles with StoppersMaterials
1- 454 gPlaceholder
Tools Required
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