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Acetone → alpha-Methylene-gamma-Butyrolactone Octadecyl Acrylate

HRID 83952
Notes
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Reaction equation

HRID 83952 reaction equation
O.CC(C)=O.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:9])[CH:7]=[CH2:8].C=C1CCOC1=O.C([O-])(=O)CCCCCCCCCCCCCCCCC.[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>>[CH2:14]=[C:13]1[CH2:12][CH2:11][O:10][C:6]1=[O:9].[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:9])[CH:7]=[CH2:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 6

HCID 180AcetoneHCID 962WaterHCID 62552Stearyl acrylateHCID 62655Sodium PersulfateHCID 68352alpha-Methylene butyrolactoneHCID 2724691Sodium Stearate

Product 1

HCID 86664979
alpha-Methylene-gamma-Butyrolactone Octadecyl Acrylate

Conditions

Temperature
60 °C

Procedure

To a high-pressure reactor with a magnetic stirrer is charged 31.50 g (1.75 mol) water, 13.50 g (0.232 mol) acetone, 25.0 g (7.70×10−2 mol) octadecyl acrylate, 25.0 g (0.255 mol) α-methylene-γ-butyrolactone, 1.25 g (4.08×10−3 mol) sodium stearate, and 0.13 g (5.46×10−4 mol) sodium persulfate. Two freeze-pump-thaw cycles using liquid nitrogen sufficiently degass the reaction medium prior to sealing the reactor and heating to 60° C. The reaction is stirred for 16 hours at 60° C. before cooling to room temperature and drying under vacuum at elevated temperature for isolation.

Workup

  1. customsufficiently degass the reaction medium
  2. temperaturebefore cooling to room temperature
  3. customdrying under vacuum at elevated temperature for isolation

Sources & evidence

ORD record
ord-0ab276d882e44ad1b14ab99621658f7b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846817B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes