Formaldehyde → 1-Naphthaldehyde
Reaction equation
[CH2:1]=[O:2].S(=O)(=O)(O)O.[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.C(C1C=CC=CC=1)C>>[C:16]1([CH:1]=[O:2])[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][CH:15]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
A bottom-removable four-necked flask having an inner volume of 2 L and equipped with a Dimroth condenser, a thermometer and a stirring blade was charged with 912 g of an aqueous 37% by mass formalin solution (11.2 mol as formaldehyde, produced by Mitsubishi Gas Chemical Company, Inc.) and 485 g of 98% by mass sulfuric acid (produced by Mitsubishi Gas Chemical Company, Inc.) in a nitrogen stream, 288 g of naphthalene (2.25 mol, produced by Wako Pure Chemical Industries, Ltd.) was dropped thereto over 6 hours while stirring under reflux under ordinary pressure at about 100° C., and the reaction was performed as it was for further 1 hour. Thereto was added 500 g of ethylbenzene (produced by Wako Pure Chemical Industries, Ltd.) as a dilution solvent and left to still stand, and then an aqueous phase as a lower phase was removed. Furthermore, the resultant was subjected to neutralization and washing with water, and ethylbenzene and unreacted naphthalene were distilled off under reduced pressure to thereby provide 371 g of a naphthalene formaldehyde resin as a light yellow solid.
Workup
- customA bottom-removable four-necked flask having
- customan inner volume of 2 L and equipped with a Dimroth condenser
- additionwas dropped
- waitwas for further 1 hour
- waitleft
- customan aqueous phase as a lower phase was removed
- washwashing with water, and ethylbenzene and unreacted naphthalene
- distillationwere distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-184c262999d9457e9c253da5076a358e
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200105B2
Reaction notes
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