Benzoic Acid → HCID 131721753, compound

HRID 1003696Notes

Reaction equation

HRID 1003696 reaction equation
[CH2:1]([NH2:10])[CH2:2][NH:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][NH2:9].[C:11]([OH:19])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:1]([NH2:10])[CH2:2][NH:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][NH2:9].[C:11]([OH:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18]

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 5565Triethylenetetramine

Product 1

HCID 131721753HCID 131721753, compoundYield 92.9%

Conditions

Temperature
120 °C

Procedure

A 1.0 liter round bottom flask equipped with a nitrogen purge, thermocouple, dropping funnel, Dean Stark collector and condenser, vacuum connection and heating mantle was charged with 292.0 g of TETA (2.0 moles) and heated to 120° C. With agitation, 244.0 g of benzoic acid (2.0 moles) was added over a 30 minute period. After addition was complete, heat was again applied to the reaction mixture to slowly raise the temperature and distill off the water from the condensation reaction. When 36.0 g of distillate was removed the reaction mixture was cooled to room temperature and collected. 498.6 g of TETA/BzOH amidelimidazoline was obtained (98.7% of theory). The product contained 6.75% free TETA by GC, a viscosity of 4,900 cP and a calculated amine hydrogen equivalent weight (AHEW) of 68.2.

Workup

  1. customA 1.0 liter round bottom flask equipped with a nitrogen
  2. custompurge
  3. temperatureDean Stark collector and condenser, vacuum connection and heating mantle
  4. additionAfter addition
  5. temperatureheat
  6. temperatureto slowly raise the temperature
  7. distillationdistill off the water
  8. customfrom the condensation reaction
  9. customWhen 36.0 g of distillate was removed the reaction mixture
  10. temperaturewas cooled to room temperature
  11. customcollected

Sources & evidence

ORD record
ord-89b028da29cb4ff5a76f66b46b3dd22e
Source dataset
uspto-grants-2000_04
Patent number
US06046282

Reaction notes

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