Methanesulfonic Acid → B-Naphthyl oleate grade II

HRID 1611467Notes

Reaction equation

HRID 1611467 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].CCOCC.[C:17](O)(=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].CS(O)(=O)=O>>[C:17]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 445639Oleic AcidHCID 197425842-Naphthol Ether

Product 1

HCID 24881592B-Naphthyl oleate grade II

Conditions

Temperature
220 °C

Procedure

To a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer, temperature probe and condenser is charged 1102.84 g (1.85 moles) of the Alkoxylate from example 15 and 497.16 g (1.76 moles) of Oleic 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-cdcde885cc0b4279908b1bf564203d65
Source dataset
uspto-grants-2006_01
Patent number
US06987195B2

Reaction notes

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