Toluene → Methyl p-toluenesulfonate

HRID 2399179Notes

Reaction equation

HRID 2399179 reaction equation
CC(C([O:6][CH2:7]CN(C)C)=O)=C.CC1C=CC([S:19](C)(=[O:21])=[O:20])=CC=1.[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[S:19]([C:26]1[CH:27]=[CH:28][C:23]([CH3:29])=[CH:24][CH:25]=1)([O:6][CH3:7])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 17869(Dimethylamino)ethyl methacrylate3×HCID 18521p-Tolyl methyl sulfone3×

Product 1

HCID 6645Methyl p-toluenesulfonate

Conditions

Temperature
55 °C

Procedure

To a 500 milliliter 4 neck round bottom flask equipped with a mechanical stirrer, an argon inlet and outlet on top of a water condenser, and a thermometer was charged 204.1 grams of the AB diblock copolymer toluene solution, prepared as described in Example I, and 110 grams of additional toluene solvent. This solution contains about 100 grams (49 weight percent of solids) of block copolymer of which 19.15 grams (0.1218 mole) are DMAEMA repeat units as determined by 1H-NMR. To this vigorously stirred solution at ambient temperature, about 25° C. throughout, unless otherwise noted, and under a gentle argon flow were added in one portion 20.4 grams (0.1096 mole) of methyl p-toluene sulfonate. The charged mole percent ratio of methyl p-toluene sulfonate to DMAEMA repeat units is 90 percent, thus nearly all of the DMAEMA repeat units have been targeted for conversion to the methyl p-toluene sulfonate quaternary ammonium AB diblock charge director. After about 1 hour, the internal temperature gently exothermed from 20° C. to 27° C. and then began to drop. After about 2 hours after the addition of the methyl p-toluene sulfonate, a heating mantle (set at 25 volts) was applied to the reaction vessel. An internal temperature of about 55° C. was maintained for the next 24 hours. A small aliquot (2.20 grams) of the methyl p-toluene sulfonate quaternary ammonium AB diblock charge director toluene solution was concentrated in the vacuum oven (50° to 55° C. for 28 hours at about 0.5 millimeter Hg) giving 0.78 gram of solid and establishing the solids level at 35.45 weight percent. To 6.79 grams of the 35.45 weight percent of methyl p-toluene sulfonate quaternary ammonium AB diblock charge director solution was added 198 grams of NORPAR 15™ and the mixture was rotoevaporated for about 1 hour at 50° to 60° C. at 40 to 60 millimeters Hg to remove the toluene.

Workup

  1. customprepared
  2. customat ambient temperature
  3. customabout 25° C.
  4. customgently exothermed from 20° C. to 27° C.
  5. concentrationA small aliquot (2.20 grams) of the methyl p-toluene sulfonate quaternary ammonium AB diblock charge director toluene solution was concentrated in the vacuum oven (50° to 55° C. for 28 hours at about 0.5 millimeter Hg)

Sources & evidence

ORD record
ord-d16e9d7d7c5c409cb4ebbaed05043c46
Source dataset
uspto-grants-1995_09
Patent number
USH0001483

Reaction notes

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