Methanesulfonic Acid → 2-Phenoxyethyl docosanoate

HRID 1611474

Reaction equation

HRID 1611474 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:38])[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][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].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:38])[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][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8215Docosanoic AcidHCID 694146262-Phenoxyethanol Ether

Product 1

HCID 222571502-Phenoxyethyl docosanoate

Conditions

Temperature
220 °C

Procedure

To a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer, temperature probe and condenser is charged 925.05 g (2.08 moles) of the Alkoxylate from example 27 and 674.95 g (1.98 moles) of Behenic 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-6958fb2a598542dd839ab0cf45555506
Source dataset
uspto-grants-2006_01
Patent number
US06987195B2

Linked notes

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