Diisopropanolamine → HCID 69203824, compound

HRID 2116742Notes

Reaction equation

HRID 2116742 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][NH:4][CH2:5][CH:6]([OH:8])[CH3:7].[C:10](O)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17]>>[CH3:1][CH:2]1[O:9][C:10]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[O:8][CH:6]([CH3:7])[CH2:5][N:4]2[CH2:3]1

Participants

3

Reactant 2

HCID 8086DiisopropanolamineHCID 33635Isononanoic acid2×

Product 1

HCID 69203824HCID 69203824, compound

Conditions

Temperature
180 °C

Procedure

To a 1 liter stirred reactor, equipped with a distillation column, condenser, and graduated receiver, the following constituents were added: 331.2 g of diisopropanol amine (DIPA) and 390.5 g (98%) of isononanoic acid. The contents were heated to 180° C. under a nitrogen blanket. After 3.5 hours, 43.4 g of water was collected overhead. The pressure was then slowly lowered to strip out unreacted DIPA. At a batch temperature of 183° C. and a pressure of 60 Pa, a cut consisting of 188 g of DIPA was removed. The batch temperature was then raised to 200° C. and the pressure dropped 333 Pa. During this period, a cut of 220 g of the amide acetal was recovered. The water of reaction passed through the condenser and was not captured with the amide acetal. This represents a 35% conversion of the isononanoic acid to amide acetal.

Workup

  1. customequipped with a distillation column, condenser
  2. additionthe following constituents were added
  3. custom43.4 g of water was collected overhead
  4. customAt a batch temperature of 183° C.
  5. customwas removed
  6. temperatureThe batch temperature was then raised to 200° C.
  7. additionthe pressure dropped 333 Pa
  8. waitDuring this period
  9. customa cut of 220 g of the amide acetal was recovered
  10. customThe water of reaction

Sources & evidence

ORD record
ord-f360933121234ad9a59362cdcdf19e6e
Source dataset
uspto-grants-2008_10
Patent number
US07439354B2

Reaction notes

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