Stearic Acid → 2-Phenoxyethyl octadecanoate

HRID 1611475Notes

Reaction equation

HRID 1611475 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[C:16](O)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].CS(O)(=O)=O>>[C:16]([O:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 5281Stearic AcidHCID 6395Methanesulfonic AcidHCID 694146262-Phenoxyethanol Ether

Product 1

HCID 222571522-Phenoxyethyl octadecanoate

Conditions

Temperature
220 °C

Procedure

To a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer, temperature probe and condenser is charged 994.13 g (2.24 moles) of the Alkoxylate from example 27 and 605.87 g (2.13 moles) of Stearic Acid. A catalytic amount of Methanesulfonic Acid (1.6 g) is charged and the reaction mixture is heated to 220° C. under nitrogen sparge. The reaction is monitored by measuring the acid value to an AV of preferably less than 5. Once the AV is reached, the temperature is cooled to 85° C. and the catalyst is neutralized with an equivalent molar amount of 45% KOH and washed once with water. The reaction is dried under vacuum yielding the desired product.

Workup

  1. customTo a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer
  2. customsparge
  3. temperaturethe temperature is cooled to 85° C.
  4. washwashed once with water
  5. customThe reaction is dried under vacuum

Sources & evidence

ORD record
ord-dea3f941130446cebc73c96aa396d45d
Source dataset
uspto-grants-2006_01
Patent number
US06987195B2

Reaction notes

Loading…