Formaldehyde → HCID 20524062, compound

HRID 1902603Notes

Reaction equation

HRID 1902603 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:16]=[O:17]>C(O)(=O)C>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:16]=[O:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 931NaphthaleneHCID 1118Sulfuric Acid

Product 1

HCID 20524062HCID 20524062, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 25.6 g (0.200 mole) naphthalene in 128 ml. glacial acetic acid, contaning 11.1 ml (0.200 mole) 96% sulfuric acid, was maintained at 116°-120° C. during addition, over 13 minutes, of 16 ml (0.200 mole) 37% formaldehyde solution. After heating and stirring at 111°-116° C. for two hours, the suspension of slightly gummy solids was cooled to room temperature and the reaction contents poured into 500 ml ice-water mixture. The solids were filtered, washed with water, and air dried. The polymer solids were dissolved in 70 ml. tetrahydrofuran and the solution added slowly to 700 ml. methanol with vigorous stirring to re-precipitate the purified polymer. The solids were collected, washed with methanol, and the precipitation procedure from tetrahydrofuran/methanol repeated. The yield of the naphthalene/formaldehyde polymer, showing a softening point of about 145° C., was 25.0 g. The weight average molecular weight, determined by light scattering in chloroform at room temperature, was 2300±100.

Workup

  1. temperatureAfter heating
  2. additionthe suspension of slightly gummy solids
  3. customthe reaction contents
  4. filtrationThe solids were filtered
  5. washwashed with water, and air
  6. customdried
  7. dissolutionThe polymer solids were dissolved in 70 ml
  8. additiontetrahydrofuran and the solution added slowly to 700 ml
  9. stirringmethanol with vigorous stirring
  10. customThe solids were collected
  11. washwashed with methanol
  12. customthe precipitation procedure from tetrahydrofuran/methanol
  13. customa softening point of about 145° C.
  14. customdetermined by light scattering in chloroform at room temperature

Sources & evidence

ORD record
ord-5462b133d0384df3ac1fa71853aa465e
Source dataset
uspto-grants-1982_12
Patent number
US04364927

Reaction notes

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