Reaction #985246

Reaction equation

tetrahydrofuran

tetrabutylammonium m-chlorobenzoate

methanol

Tetrahydrofuran

1,1-bis(trimethylsiloxy) 2-methyl propene

tetrabutylammonium m-chlorobenzoate

→

2-hydroxyethyl methacrylate

methacrylic acid

benzyl methacrylate

ethyltriethyleneglycol methacrylate

Conditions

Workup

1. 1
   OtherA 3-liter flask was equipped with a mechanical stirrer
2. 2
   Otherwere started at time 0 minutes
3. 3
   workup.ADDITIONFeed I was added over 200 minutes
4. 4
   TemperatureThe pot was heated
5. 5
   Temperatureto reflux
6. 6
   workup.DISTILLATION500 g were distilled
7. 7
   workup.ADDITIONA solution of water (124 g) and dichloroacetic acid (0.2 g) were added to the pot and
8. 8
   Temperaturerefluxed for 60 minutes
9. 9
   TemperatureAfter refluxing
10. 10
    workup.DISTILLATION725 g were distilled
11. 11
    workup.ADDITION2-pyrrolidinone (889 g) was added

Procedure

A 3-liter flask was equipped with a mechanical stirrer, thermocouple, N2 inlet, condenser, drop funnel and syringe pump. Tetrahydrofuran (950 g), 1,1-bis(trimethylsiloxy) 2-methyl propene (46.2 g) and tetrabutylammonium m-chlorobenzoate (2 g) was added into pot. Feed I (tetrahydrofuran (5 g) and tetrabutylammonium m-chlorobenzoate (0.8 g)) and Feed II (benzyl methacrylate (600 g), 2-(trimethylsiloxy)ethyl methacrylate (312 g), ethyltriethyleneglycol methacrylate (100 g) and trimethylsilyl methacrylate (152 g)) were started at time 0 minutes. Feed I was added over 200 minutes. Feed II was added over 60 minutes. After 360 minutes 90 g of methanol was added to the pot. The pot was heated to reflux and 500 g were distilled. A solution of water (124 g) and dichloroacetic acid (0.2 g) were added to the pot and refluxed for 60 minutes. After refluxing, 725 g were distilled and 2-pyrrolidinone (889 g) was added. This synthesis produced a random acrylic polymer of 60 wt % benzyl methacrylate, 20 wt % 2-hydroxyethyl methacrylate, 10 wt % ethyltriethyleneglycol methacrylate and 10 wt % methacrylic acid at a Mn of 5300. The final solution contained 52% polymer solids in 2-pyrrolidinone.

Source