Formaldehyde → 1-Naphthaldehyde

HRID 1499317Notes

Reaction equation

HRID 1499317 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(O)CCC.O>[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]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 931NaphthaleneHCID 1118Sulfuric AcidHCID 7500Ethylbenzene

Product 1

HCID 61951-NaphthaldehydeYield 102.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

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 384 g of 86% by mass paraformaldehyde (11.0 mol as formaldehyde, produced by Mitsubishi Gas Chemical Company, Inc.), 437 g of ion-exchange water (produced by Mitsubishi Gas Chemical Company, Inc.), 297 g of 1-butanol (produced by Wako Pure Chemical Industries, Ltd.) and 398 g of 98% by mass sulfuric acid (produced by Mitsubishi Gas Chemical Company, Inc.) in a nitrogen stream, 256 g of naphthalene (2.0 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 2 hours. 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 319 g of a naphthalene formaldehyde resin as a light yellow liquid.

Workup

  1. customA bottom-removable four-necked flask having
  2. customan inner volume of 2 L and equipped with a Dimroth condenser
  3. additionwas dropped
  4. waitwas for further 2 hours
  5. waitleft
  6. customan aqueous phase as a lower phase was removed
  7. washwashing with water, and ethylbenzene and unreacted naphthalene
  8. distillationwere distilled off under reduced pressure

Sources & evidence

ORD record
ord-ce550ce267d941a7bee7e3a6390268b3
Source dataset
uspto-grants-2015_12
Patent number
US09200105B2

Reaction notes

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