Water → Propylene glycol methyl ether acetate

HRID 2284886Notes

Reaction equation

HRID 2284886 reaction equation
CC(N=N[C:8]([C:11]#N)([CH3:10])C)(C#N)C.[OH2:13].C(#N)C.[CH:17]([OH:20])([CH3:19])C.C[C:22](=[O:25])CC>CCCCCC>[C:17]([O:20][CH:8]([CH3:10])[CH2:11][O:25][CH3:22])(=[O:13])[CH3:19]

Participants

7

Reactant 5

HCID 962WaterHCID 3776IsopropanolHCID 6342AcetonitrileHCID 6547AzobisisobutyronitrileHCID 6569Methyl Ethyl Ketone2×

Product 1

HCID 7946Propylene glycol methyl ether acetateYield 77%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

1.8 g (20 mol %) of the compound (M-2) and 8.2 g (20 mol %) of the compound (M-16) were dissolved in 10 g of 2-butanone, and 0.37 g (5 mol % based on the total number of moles of the compounds) of AIBN (initiator) was added to the solution to prepare a monomer solution. A three-necked flask (100 mL) was charged with 5 g of 2-butanone, purged with nitrogen for 30 minutes, and heated to 80° C. with stirring. The monomer solution prepared as described above was added dropwise to the flask from a dropping funnel over 4 hours. The monomers were polymerized for 6 hours from the start of dropwise addition of the monomer solution. After completion of polymerization, the polymer solution was cooled with water to 30° C. or less. After transferring the polymer solution to a separating funnel (500 mL), 10 g of acetonitrile, 5 g of isopropanol, and 65 g of n-hexane were added to the polymer solution, and the mixture was stirred, and allowed to stand for 1 hour. The lower layer was then collected, and the solvent was replaced with propylene glycol monomethyl ether acetate to obtain a propylene glycol monomethyl ether acetate solution of a polymer (D-1) (yield: 77%). The polymer (D-1) had an Mw of 8100 and a dispersity (Mw/Mn) of 1.63. It was found by 13C-NMR analysis that the content of structural units derived from the compound (M-2) and the content of structural units derived from the compound (M-16) in the polymer (D-1) were 18.5 mol % and 81.5 mol %, respectively.

Workup

  1. additionwas added to the solution
  2. customto prepare a monomer solution
  3. custompurged with nitrogen for 30 minutes
  4. customThe monomer solution prepared
  5. additionabove was added dropwise to the flask from a dropping funnel over 4 hours
  6. customThe monomers were polymerized for 6 hours from the start of dropwise addition of the monomer solution
  7. customAfter completion of polymerization
  8. additionwere added to the polymer solution
  9. stirringthe mixture was stirred
  10. customThe lower layer was then collected

Sources & evidence

ORD record
ord-7bb5f40e246544f3a30ba742b2b158cc
Source dataset
uspto-grants-2015_09
Patent number
US09146466B2

Reaction notes

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