Methyl Methacrylate → HCID 197116, compound

HRID 2372699Notes

Reaction equation

HRID 2372699 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([O:12][CH3:13])(=[O:11])[C:8]([CH3:10])=[CH2:9].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC>C1(C)C(C)=CC=CC=1.C(O)C>[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([O:12][CH3:13])(=[O:11])[C:8]([CH3:10])=[CH2:9]

Participants

7

Reactant 4

HCID 6658Methyl Methacrylate2×HCID 7187Benzoyl Peroxide2×HCID 8058HexaneHCID 87595Methacrylate2×

Product 1

HCID 197116HCID 197116, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7237O-XyleneSolvent2×

Procedure

Methacrylic acid (0.1 mol) and hexaethyldititanoxane (0.05 mol) were dissolved in xylene and subjected to reaction. The water that formed as the reaction proceeded was removed together 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 triethyltitanyl methacrylate (m.p. 89° C.; yield, 54%). This triethyltitanyl 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 triethyltitanyl 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. This solid product was dissolved in ethanol, added slowly to ice water and subjected to re-precipitation. The precipitate was recovered and dried to obtain poly(triethyltitanyl methacrylate-methyl methacrylate). Yield, 75%, Mn, 35,000; Mw/Mn=2.2, IR (ν cm-1), 1720, 1710, 1160, 1100, 720; atomic absorption spectrum (Ti content), 14.80 (found) and 14.95 (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
  11. customsubjected to re-precipitation
  12. customThe precipitate was recovered
  13. customdried

Sources & evidence

ORD record
ord-f06fe41255e249df85cc1dcbb222b194
Source dataset
uspto-grants-1992_03
Patent number
US05100762

Reaction notes

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