N,N-Dimethyl-1,3-propanediamine → SDM

HRID 1658154Notes

Reaction equation

HRID 1658154 reaction equation
[CH:1]([C:9]1=[CH:10][C:11]([O:13][C:14]1=[O:15])=O)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=CC1C=CC=CC=1.C1C(=O)OC(=O)C=1.[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][NH2:36]>CN(C)C=O>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][N:36]1[C:14](=[O:15])[CH:9]=[CH:10][C:11]1=[O:13]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 62707Lytron 810HCID 54215275Styrenemaleic anhydride

Product 1

HCID 3080809SDM

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 250 g of copoly(styrene-maleic anhydride (commercially available from the Monsanto Chemical Company under the tradename of Lytron 810) in 2500 ml of dry dimethylformamide is made by stirring in a 5-liter flask, containing a reflux condenser, thermometer, stirrer, and dropping funnel. The mixture is heated to 110°C and 230 g of N,N-dimethyl-1,3-propanediamine is added slowly at a rate to keep the mixture boiling slightly. Polymer precipitates as a gummy mass at first but goes back into solution after about half of the amine is added. The condenser is replaced by a distillation column and about 500 ml of material is removed by distillation with stirring. The residue is cooled, precipitated in water, collected by filtration and air-dried at room temperature for 2 days. The solid is dissolved in acetone, and again precipitated in water and air-dried. Yield = 260 g of off-white, friable solid.

Workup

  1. additioncontaining a reflux condenser
  2. customthermometer, stirrer, and dropping
  3. customPolymer precipitates as a gummy mass at first but
  4. additionis added
  5. distillationThe condenser is replaced by a distillation column and about 500 ml of material
  6. customis removed by distillation
  7. stirringwith stirring
  8. temperatureThe residue is cooled
  9. customprecipitated in water
  10. filtrationcollected by filtration
  11. customair-dried at room temperature for 2 days
  12. dissolutionThe solid is dissolved in acetone
  13. customagain precipitated in water
  14. customair-dried

Sources & evidence

ORD record
ord-3272e17f5fcf442d80bddb8539f740db
Source dataset
uspto-grants-1976_06
Patent number
US03962527

Reaction notes

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