Methanol → Methacrylic Acid

Participants

Reaction Steps

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.

Provenance & Evidence