Methyl Methacrylate → HCID 131717215, compound

HRID 2372698Notes

Reaction equation

HRID 2372698 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([GeH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8].[C:14]([O:19][CH3:20])(=[O:18])[C:15]([CH3:17])=[CH2:16].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC>C1(C)C(C)=CC=CC=1>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([GeH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8].[C:14]([O:19][CH3:20])(=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

6

Reactant 4

HCID 6658Methyl Methacrylate2×HCID 7187Benzoyl Peroxide2×HCID 8058HexaneHCID 88509148HCID 88509148, compound2×

Product 1

HCID 131717215HCID 131717215, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

Methacrylic acid (0.1 mol) and hexaethyldigermoxane (0.05 mol) were dissolved in xylene and subjected to reaction. The water that formed as the reaction proceeded was removed with the solvent by distillation. The by-product of the reaction was distilled off under vacuum and the residue was dried under vacuum to obtain triethylgermane methacrylate (m.p. 78° C.; yield, 70%). This triethylgermane methacrylate and methyl methacrylate were put into a round-bottom flask at a molar ratio of 1:1 and xylene was added to achieve a concentration of ca. 50%. Benzoyl peroxide (1 mol % of the sum of the triethylgermane methacrylate and methyl methacrylate) dissolved in xylene was charged into a dropping funnel. After equipping the flask with this funnel, the benzoyl peroxide solution was dripped in an amount of about 10% of the total quantity of the solution. Thereafter, the flask was heated to the reflux temperature and the remaining polymerization initiator was slowly added dropwise until the reaction was completed in 8 hours. After the reaction, the content of the flask was added to n-hexane and subjected to re-precipitation. The resulting precipitate was recovered and dried to obtain a solid product, which was slowly added to ice water and re-precipitated. The precipitate was recovered and dried to obtain poly(triethylgermane methacrylate-methyl methacrylate). Yield, 82%, Mn, 50,000; Mw/Mn=2.0, IR (ν cm-1), 1720, 1135, 760, 710; atomic absorption spectrum (Ge content), 21.00 (found) and 21.05 (calculated).

Workup

  1. additionwas added
  2. additionwas charged into a dropping funnel
  3. temperatureThereafter, the flask was heated to the reflux temperature
  4. customthe remaining polymerization initiator
  5. additionwas slowly added dropwise until the reaction
  6. customAfter the reaction
  7. customsubjected to re-precipitation
  8. customThe resulting precipitate was recovered
  9. customdried
  10. customto obtain a solid product, which
  11. customre-precipitated
  12. customThe precipitate was recovered
  13. customdried

Sources & evidence

ORD record
ord-6e2716416b6344ed86383093a62ee159
Source dataset
uspto-grants-1992_03
Patent number
US05100762

Reaction notes

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