Ethanethiol → Methyl Methacrylate

HRID 1840611Notes

Reaction equation

HRID 1840611 reaction equation
[CH3:1]CS.[N-]=[C:5]=[O:6].[C:7]([O-:20])(=[O:19])[CH2:8][CH2:9]CCCCCCCCC.[C:21]([O-:34])(=O)[CH2:22][CH2:23][CH2:24]CCCCCCCC.C([Sn+2]C[CH2:41][CH2:42][CH3:43])CCC>C1COCC1>[C:7]([O:6][CH3:5])(=[O:20])[C:8]([CH3:9])=[CH2:1].[C:7]([O:34][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:19])[C:42]([CH3:41])=[CH2:43]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 105034IsocyanateHCID 9809426Di-n-butyldilauryltin

Product 2

HCID 6658Methyl MethacrylateHCID 7354Butyl Methacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Methyl methacrylate (2.2 mol) and butyl methacrylate (1.5 mol) are polymerized with azoisobutyronitrile (AIBN) in THF. Thioethanol (0.12 mol) is added as regulator. To this solution are added a trifunctional isocyanate (trimeric hexamethylene diisocyanate; Basonat® HB 100, BASF) (0.12 mol), dissolved in THF, and also dibutyltin dilaurate. The solution is adjusted to a solids content of 50% with THF. In line with the remaining isocyanate content, an OH-terminated polyvinylpyrrolidone (K value about 17, 50% strength in methyl isobutyl ketone) is added. The reaction is continued until isocyanate groups are no longer detectable.

Workup

  1. customIn line with the remaining isocyanate content, an OH-terminated polyvinylpyrrolidone (K value about 17, 50% strength in methyl isobutyl ketone)
  2. additionis added

Sources & evidence

ORD record
ord-8688ba4dadf64132a5bf1ac63bb85d2c
Source dataset
uspto-grants-2004_01
Patent number
US06680355B1

Reaction notes

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