Phosphoric Acid → 2-Nonylphenoxyethanamine

HRID 1197682Notes

Reaction equation

HRID 1197682 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13](O)=[CH:14][CH:15]=1.[CH3:17][C:18]1[O:19]CC[N:22]=1.P(=O)(O)(O)O.[OH-].[Na+]>O>[CH2:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[O:19][CH:18]([NH2:22])[CH3:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 17524-NonylphenolHCID 14798Sodium HydroxideHCID 707132-Methyl-2-oxazoline

Product 1

HCID 191076952-Nonylphenoxyethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To a 250-ml three-necked flask equipped with a thermometer, stirrer, condenser and nitrogen inlet were charged 66 g. of nonylphenol and 30 g. of 2-methyl-2-oxazoline. The mixture was heated to 200° C. for six hours. About 80 g. of 85% phosphoric acid and 20 g. of water were then added. The mixture was heated to reflux for eight hours. The resulting reaction mixture was neutralized with sodium hydroxide solution. The resulting product was washed with water and then dried. 2-Nonylphenoxyethanamine was obtained in quantitative yield and the product purity by NMR spectroscopy analysis was found to be about 98%.

Workup

  1. customTo a 250-ml three-necked flask equipped with a thermometer, stirrer, condenser and nitrogen inlet
  2. additionwere charged 66 g
  3. temperatureThe mixture was heated
  4. temperatureto reflux for eight hours
  5. customThe resulting reaction mixture
  6. washThe resulting product was washed with water
  7. customdried

Sources & evidence

ORD record
ord-59477bcafeae455e9fd5719adc44f9d9
Source dataset
uspto-grants-1994_01
Patent number
US05276192

Reaction notes

Loading…