Water → Tributyltin methacrylate

HRID 2372695Notes

Reaction equation

HRID 2372695 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([Sn:11]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])O)[CH2:8][CH2:9][CH3:10].O>C1(C)C(C)=CC=CC=1>[C:1]([O:6][Sn:11]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:7][CH2:8][CH2:9][CH3:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4093Methacrylic AcidHCID 178448249HCID 178448249, compound

Product 1

HCID 16682828Tributyltin methacrylateYield 64%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methacrylic acid (0.1 mol) and tri-n-butylhydroxystannane (0.1 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 tri-n-butylstannyl methacrylate (m.p. 46° C.; yield, 64%). This tri-n-butylstannyl methacrylate was put into a round-bottom flask and xylene was added to attain a concentration of ca. 50%. As a polymerization initiator, benzoyl peroxide (1 mol % of)the tri-n-butylstannyl 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. Thereafter, the flask was heated to the reflux temperature and the remaining 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 poly(tri-n-butylstannyl methacrylate). Yield, 80%, Mn, 30,000; Mw/Mn=1.8, IR (ν -1), 1700, 1160, 700; atomic absorption spectrum (Sn content), 31.44 (found) and 31.64 (calculated).

Workup

  1. customsubjected to reaction
  2. customproceeded was removed together with the solvent by distillation
  3. distillationThe by-product of the reaction was distilled off under vacuum
  4. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-8ad08f894a954673800780b28274fc88
Source dataset
uspto-grants-1992_03
Patent number
US05100762

Reaction notes

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