2-Ethylhexanol → 2-Ethylhexyl 2-ethylhexanoate

HRID 433057Notes

Reaction equation

HRID 433057 reaction equation
[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([OH:6])=[O:5])[CH3:2].[CH2:11]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]O)[CH3:12]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].O>[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([O:6][CH2:14][CH:13]([CH2:11][CH3:12])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 77202-EthylhexanolHCID 86972-Ethylhexanoic Acid

Product 1

HCID 239062-Ethylhexyl 2-ethylhexanoateYield 95.9%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

144 g (1 mol) of 2-ethylhexanoic acid and 143 g (1.1 mol) of 2-ethylhexanol were fed to a four-necked flask equipped with a stirrer, a thermometer and a water separator having a condenser tube, and the mixture was heated to 200° C. under reduced pressure in the presence of a tetraisopropyl titanate catalyst. Esterification reaction was carried out for about 9 hours while removing the formed water by the water separator. After the reaction, the excess 2-ethylhexanol was distilled off, and the product was neutralized with excess sodium hydroxide and then washed with water to neutrality. The product was then treated with activated carbon (0.3 wt. % relative to the starting materials fed) at 90° C., and was then filtered, giving 246 g of (2-ethylhexyl) 2-ethylhexanoate, which was then dehydrated for 5 hours at a temperature of 100° C. and a reduced pressure of 13.3 MPa. The resulting ester had a total acid number of 0.01 mgKOH/g, a water content of 11 ppm, a kinematic viscosity of 2.7 mm2/s (40° C.) and 1.1 mm2/s (100° C.), a volume resistivity of 3.0×1013 Ω·cm, and a two-layer separation temperature of −24° C.

Workup

  1. customequipped with a stirrer
  2. customEsterification reaction
  3. customwhile removing the formed water by the water separator
  4. customAfter the reaction
  5. distillationthe excess 2-ethylhexanol was distilled off
  6. washwashed with water to neutrality
  7. additionThe product was then treated with activated carbon (0.3 wt. % relative to the starting materials
  8. customat 90° C.
  9. filtrationwas then filtered

Sources & evidence

ORD record
ord-e9fedbf3eca946f2b81f96c9650e735c
Source dataset
uspto-grants-2003_12
Patent number
US06667285B1

Reaction notes

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