Reaction #2631

Reaction equation

epichlorohydrin

methyl violet

Butoxytriglycol

1-chlorooctane

epichlorohydrin

→

BTG H2O

Solvents

toluene

water

acetic acid

toluene

acetic acid

Conditions

Workup

1. 1
   OtherTo a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube
2. 2
   OtherTo a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube
3. 3
   TemperatureBoth flasks were heated
4. 4
   workup.DISTILLATIONto azeotropically distill off the water
5. 5
   Othersparge
6. 6
   ConcentrationAfter the water concentration in each flask
7. 7
   workup.ADDITIONSodium methoxide was added to each flask in an amount that OH
8. 8
   TemperatureHeat
9. 9
   workup.DISTILLATIONto distill off
10. 10
    Otherformed methanol
11. 11
    workup.DISTILLATIONby distilling off half of the initial weight of toluene from the flask
12. 12
    TemperatureIn the first flask, the reaction mixture was then refluxed for 1 hour
13. 13
    TemperatureThe reaction mixture was then maintained at 70° C. for about 2 hours
14. 14
    Temperaturethe contents heated to 75°-85° C. for 2 hours
15. 15
    workup.ADDITIONwas added such that the mole ratio of Cl
16. 16
    TemperatureThe reaction mixture was then refluxed until the alkalinity titration value

Procedure

To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)150 -OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)50 -OH (surfactant) and 2 parts of toluene. Both flasks were heated to azeotropically distill off the water with stirring +N2 sparge. After the water concentration in each flask was less than 50 ppm the mixture was cooled to 55° C. Sodium methoxide was added to each flask in an amount that OH:NaOMe=1:1 based on the calculated hydroxyl value of surfactant. Heat was applied to distill off formed methanol by distilling off half of the initial weight of toluene from the flask. In the first flask, the reaction mixture was then refluxed for 1 hour. The flask was cooled to 60° C. afterwhich 1.1 moles of epichlorohydrin were added per mole sodium alkoxide. The reaction mixture was then maintained at 70° C. for about 2 hours. When alkalinity by titration approached zero, the excess epichlorohydrin was vacuum stripped. A 4.0 gram aliquot of the reaction mixture +4 grams of tetraethylammonium bromide were dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The difference in the total alkalinity minus the HClO4 titration equals the amount of epoxide. The contents of the first and second flasks were mixed in a third flask such that the epoxy/alkoxide molar ratio was equal to 1:1 and the contents heated to 75°-85° C. for 2 hours. When the epoxy titration value equaled zero, 1-chlorooctane was added such that the mole ratio of Cl:ONa was 1:1. The reaction mixture was then refluxed until the alkalinity titration value was zero. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight.

Source