Butyl methanesulfonate → Butyl Stearate

HRID 1593719

Reaction equation

[C:1]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([O-])(=O)CCCCCCCCCCCCCCCCC.[K+:45].[CH3:46][S:47]([O:50]CCCC)(=[O:49])=[O:48]>>[CH3:46][S:47]([O-:50])(=[O:49])=[O:48].[K+:45].[C:1]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 15953Butyl methanesulfonate

HCID 31278Butyl Stearate

HCID 23673840Potassium Stearate

Product 2

HCID 31278Butyl Stearate

HCID 23666501Potassium methanesulphonate

Procedure

An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired butyl methanesulfonate (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50° C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with butyl methanesulfonate to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted butyl methanesulfonate, a 51% reduction.

Sources & evidence

ORD record: ord-10d5384285bd45ec8ec72b7fe6287bbb
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297813B2

Linked notes

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