Butyl Methacrylate → Methacrylic Acid

HRID 1655137Notes

Reaction equation

HRID 1655137 reaction equation
O1CCCC1.[C:6]([O:11][Si](C)(C)C)(=[O:10])[C:7]([CH3:9])=[CH2:8].[C:16]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:20])[C:17]([CH3:19])=[CH2:18]>CC1C=CC(C)=CC=1>[C:16]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:20])[C:17]([CH3:19])=[CH2:18].[C:6]([OH:11])(=[O:10])[C:7]([CH3:9])=[CH2:8]

Participants

6

Reactant 3

HCID 7354Butyl MethacrylateHCID 8028TetrahydrofuranHCID 27338392-Propenoic acid, 2-methyl-, trimethylsilyl ester

Product 2

HCID 4093Methacrylic AcidHCID 7354Butyl Methacrylate

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A block copolymer of n-butyl methacrylate and methacrylic acid was prepared by adding 3750 grams of tetrahydrofuran and 7.4 grams of p-xylene to a 12-liter flask equipped with a mechanical stirrer, thermometer, nitrogen inlet, drying tube outlet and addition funnels. Feed I, which consisted of 3.0 ml of a 1.0 M solution of tetrabutyl ammonium m-chlorobenzoate catalyst in acetonitrile, was started at 0 minutes and added over 150 minutes and 291.1 gm (1.25 mole) of an initiator, 1,1-bis(trimethylsiloxy-2-methyl propene), was injected. Feed II, which consisted of 1976 gm (12.5 M) trimethylsilyl methacrylate, was started at 0 minutes and added over 35 minutes. One hundred eighty minutes after Feed II was completed (over 99% of the monomers had reacted), Feed III, which consisted of 1772 gm (12.5 M) butyl methacrylate, was started and added over 30 minutes.

Workup

  1. customequipped with a mechanical stirrer
  2. customthermometer, nitrogen inlet, drying
  3. additiontube outlet and addition funnels
  4. additionadded over 150 minutes
  5. waitwas started at 0 minutes
  6. additionadded over 35 minutes
  7. customOne hundred eighty minutes
  8. additionadded over 30 minutes

Sources & evidence

ORD record
ord-a72a83f17a1c4019962f740a6dd9f504
Source dataset
uspto-grants-1993_10
Patent number
US05250109

Reaction notes

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