Methanol → Methacrylic Acid

HRID 898064Notes

Reaction equation

HRID 898064 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O:8][C:9]([O:13][Si](C)(C)C)=[C:10]([CH3:12])[CH3:11].Cl[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([O-:26])=[O:25].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:47][OH:48]>>[C:9]([O:13][CH2:24][C:23]1[CH:27]=[CH:28][CH:29]=[CH:21][CH:22]=1)(=[O:8])[C:10]([CH3:12])=[CH2:11].[C:24]([O:26][CH2:3][CH2:2][OH:1])(=[O:25])[C:23]([CH3:22])=[CH2:27].[C:9]([OH:13])(=[O:8])[C:10]([CH3:12])=[CH2:11].[CH2:10]([CH:9]([OH:8])[CH2:47][O:48][CH2:3][CH2:2][O:1][CH2:5][CH2:4][OH:25])[CH3:11].[C:9]([OH:13])(=[O:8])[C:10]([CH3:12])=[CH2:11]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028Tetrahydrofuran2×HCID 111179393,5-Dioxa-2,6-disilaheptane, 2,2,6,6-tetramethyl-4-(1-methylethylidene)-HCID 219221871-Butanaminium, N,N,N-tributyl-, 3-chlorobenzoate (1:1)2×

Product 4

HCID 4093Methacrylic AcidHCID 133602-Hydroxyethyl MethacrylateHCID 17236Benzyl methacrylateHCID 86594594HCID 86594594, compound

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.

Workup

  1. customA 3-liter flask was equipped with a mechanical stirrer
  2. customwere started at time 0 minutes
  3. additionFeed I was added over 200 minutes
  4. temperatureThe pot was heated
  5. temperatureto reflux
  6. distillation500 g were distilled
  7. additionA solution of water (124 g) and dichloroacetic acid (0.2 g) were added to the pot and
  8. temperaturerefluxed for 60 minutes
  9. temperatureAfter refluxing
  10. distillation725 g were distilled
  11. addition2-pyrrolidinone (889 g) was added

Sources & evidence

ORD record
ord-1f1bb58ce2004b879c4d56d5e63d6e17
Source dataset
uspto-grants-2008_04
Patent number
US07351278B2

Reaction notes

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