Phenothiazine → Ethyl Acrylate

HRID 1814404Notes

Reaction equation

HRID 1814404 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].[C:7]([O:11][CH2:12][CH3:13])(=[O:10])[CH:8]=[CH2:9].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>C(O)C>[C:7]([O:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])(=[O:10])[CH:8]=[CH2:9].[C:7]([O:11][CH2:12][CH3:13])(=[O:10])[CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 7108PhenothiazineHCID 79022-(Dimethylamino)ethanolHCID 8821Ethyl Acrylate2×

Product 2

HCID 8821Ethyl AcrylateHCID 171112-(Dimethylamino)ethyl acrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a stirred reactor provided with superposed distillation column (100 cm, 0.5 cm Raschig rings) and condenser a mixture of 223 g of dimethylaminoethanol, 500 g of ethyl acrylate (H2O content=0.02% by weight), 20.3 g of catalyst from Example 3 and 0.01 g of phenothiazine was heated to boiling under atmospheric pressure while stirring. The reaction temperature rose from 105° C. to 130° C. during the reaction time (3.5 hours). A mixture of ethanol and ethyl acrylate was taken off at the top of the column. The reflux ratio was initially 1:1 and was increased after 3 hours to 5:1. 230 g of distillate were separated off. After the transesterification was complete, the reaction mixture was subjected to a simple vacuum distillation (25 mbar, final temperature of 120° C.). 475 g of distillate (349 g of dimethylaminoethyl acrylate, 126 g of ethyl acrylate) were obtained. The distillation residue, mainly catalyst, inhibitor and polymers, amounted to 28 g. According to analysis of the distillate by gas chromatography, a yield of 97.5%, based on the alcohol, was achieved.

Workup

  1. customIn a stirred reactor provided with superposed distillation column (100 cm, 0.5 cm Raschig rings) and condenser
  2. temperaturewas heated
  3. customrose from 105° C. to 130° C. during the reaction time (3.5 hours)
  4. temperaturewas increased after 3 hours to 5:1
  5. custom230 g of distillate were separated off
  6. distillationthe reaction mixture was subjected to a simple vacuum distillation (25 mbar
  7. customtemperature of 120° C.

Sources & evidence

ORD record
ord-3cbcc2d7094845e38b45900c6112535e
Source dataset
uspto-grants-2005_04
Patent number
US06875888B2

Reaction notes

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