4-Nonylphenol → HCID 14122791, compound

HRID 2305003Notes

Reaction equation

HRID 2305003 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-NonylphenolHCID 6354Ethylene Oxide2×

Product 1

HCID 14122791HCID 14122791, compoundYield 333.5%

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 mole) of nonylphenol having a branched nonyl group and an ortho/para ratio of 1/9, and 0.55 g of 40% aqueous sodium hydroxide solution (5.5 mmoles of sodium hydroxide) were charged. The reaction system was substituted with nitrogen and thereafter heated to 120° C. Successively the reaction system was evacuated to 50 mmHg and dehydrated for an hour. After dehydration, the system was returned to atmospheric pressure with nitrogen and heated to 150° C. While maintaining the same temperature, 220 g (4.99 moles) of ethylene oxide were charged to the reaction system over 5 hours under the pressure of 0.2 to 0.4 MPa (gauge). After finishing ethylene oxide charge, the reaction mixture was kept at the same temperature for an hour. After cooling, the reaction mixture was neutralized with 0.0.35 g (5.8 mmoles) of acetic acid to obtain 440 g of nonylphenol ethylene oxide adduct. The adduct obtained had an ethylene oxide addition mole numbers of 5.0 for one mole of nonylphenol.

Workup

  1. customTo a 1,000 ml autoclave equipped with an ethylene oxide inlet tube
  2. customSuccessively the reaction system was evacuated to 50 mmHg
  3. waitdehydrated for an hour
  4. temperatureheated to 150° C
  5. additionwere charged to the reaction system over 5 hours under the pressure of 0.2 to 0.4 MPa (gauge)
  6. additioncharge
  7. waitthe reaction mixture was kept at the same temperature for an hour
  8. temperatureAfter cooling

Sources & evidence

ORD record
ord-5e5ff3faec094ae48ce0171f43e82015
Source dataset
uspto-grants-2002_08
Patent number
US06437194B2

Reaction notes

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