Edetate Sodium → Dimethyl acetylenedicarboxylate

HRID 1252014Notes

Reaction equation

HRID 1252014 reaction equation
[C:1](N)(=[O:4])[CH:2]=[CH2:3].CN(C)[C:8](=[O:11])C=C.C(N(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].[Na+].[PH2]([O-])=O.[Na+].C[C:42]([O:44][CH:45]=C)=[O:43].C=CCl.S(OOS([O-])(=O)=O)([O-])(=O)=O>O>[CH3:8][O:11][C:1]([C:2]#[C:3][C:42]([O:44][CH3:45])=[O:43])=[O:4]

Participants

8

Conditions

Temperature
72 °C

Procedure

For comparison purposes, a terpolymer outside the scope of applicants' invention was prepared and tested. Into a 1 liter resin reaction flask fitted with a stirrer, thermometer, condenser, nitrogen inlet and a port for adding liquid, is placed 470.1 g of deionized water, 75.2 g of a 50% solution of acrylamide, 350 g of a 50% solution of AMPS, 37.6 g of N, N-dimethylacrylamide and 0.1 g of Versene 100. The solution is stirred and to it added a solution of 0.5 g of sodium hypophosphite dissolved in 16 g of deionized water. The solution is sparged sub-surface with nitrogen and then heated to 72° C. with an external heating jacket. A solution of 0.4 g of ammonium persulfate dissolved in 50 g of deionized water is prepared and placed in a metering pump connected to the flask at the inlet part with a fine bore tygon tubing. The persulfate solution is added uniformly to the flask over a period of three hours, maintaining a temperature of 72 ° C.±2° C. in the reactor by initially cooling and then warming. After the persulfate solution is added, the 72° C. temperature is maintained for an additional hour, then the solution is cooled to about 40 C and discharged. The resulting product was a clear, very pale yellow, viscous liquid with a solids content of 25%. The viscosity, as measured on a Brookfield viscometer, was 21,300 cps, spindle 4, speed 12. The pH of the solution was 3.0.

Workup

  1. customFor comparison purposes, a terpolymer outside the scope of applicants' invention was prepared
  2. customfitted with a stirrer
  3. additionthermometer, condenser, nitrogen inlet and a port for adding liquid
  4. customThe solution is sparged sub-surface with nitrogen
  5. dissolutionA solution of 0.4 g of ammonium persulfate dissolved in 50 g of deionized water
  6. customis prepared
  7. temperaturemaintaining a temperature of 72 ° C.±2° C. in the reactor
  8. temperatureby initially cooling
  9. temperaturewarming
  10. temperaturethe 72° C. temperature is maintained for an additional hour
  11. temperaturethe solution is cooled to about 40 C

Sources & evidence

ORD record
ord-c60bfd01d1d64c86925c4f6c59d8178a
Source dataset
uspto-grants-1988_05
Patent number
US04741843

Reaction notes

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