4-Nonylphenol → HCID 14122791, compound

HRID 2305011Notes

Reaction equation

HRID 2305011 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]([OH:16])=[CH:14][CH:15]=1.C1[O:19]C1>[OH-].[Na+].C(O)(=O)C>[CH2:13]1[O:16][CH2:14]1.[CH2:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[OH:19])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 2

HCID 17524-Nonylphenol2×HCID 6354Ethylene Oxide3×

Product 1

HCID 14122791HCID 14122791, compoundYield 500.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 14798Sodium HydroxideCatalyst

Conditions

Temperature
120 °C

Procedure

To a 1,000 ml autoclave equipped with an ethylene oxide inlet tube, 220 g (0.998 moles) of nonylphenol having a branched mixture of nonyl group and an ortho/para ratio of 1/9 and 0.83 g (8.3 mmoles as sodium hydroxide) of 40% aqueous sodium hydroxide solution were charged. The reaction system was substituted with nitrogen, heated to 120° C., successively evacuated to 50 mmHg, and dehydrated for an hour under reduced pressure. After the dehydration, the reaction system was returned to atmospheric pressure by feeding nitrogen and heated to 150° C. While maintaining the temperature, 440 g (9.99 moles) of ethylene oxide was fed to the reaction system over 8 hours under increased gauge pressure of 0.2 to 0.4 MPa to carry out ethylene oxide addition reaction of nonylphenol. After ethylene oxide charge, the reaction system was further kept at the same temperature for an hour. After cooling the reaction system, the reaction system was neutralized with 0.52 g (8.7 mmoles) of acetic acid to obtain 660 g of nonylphenol ethylene oxide adduct. Nonylphenol ethylene oxide adduct thus obtained had an average ethylene oxide addition mole number of 10.0.

Workup

  1. customTo a 1,000 ml autoclave equipped with an ethylene oxide inlet tube
  2. customsuccessively evacuated to 50 mmHg
  3. waitdehydrated for an hour under reduced pressure
  4. temperatureheated to 150° C
  5. temperatureunder increased gauge pressure of 0.2 to 0.4 MPa
  6. waitthe reaction system was further kept at the same temperature for an hour
  7. temperatureAfter cooling the reaction system

Sources & evidence

ORD record
ord-95d763c56fda4198bfaae50215a67b11
Source dataset
uspto-grants-2002_08
Patent number
US06437194B2

Reaction notes

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