Water → Octyl methacrylate

HRID 513882Notes

Reaction equation

HRID 513882 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:9]([OH:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].C(=O)(O)[O-].[Na+].O>FC(F)(F)S(O)(=O)=O>[C:9]([O:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

6

Reactant 4

HCID 962WaterHCID 4093Methacrylic AcidHCID 81251-OcteneHCID 516892Sodium Bicarbonate

Product 1

HCID 16542Octyl methacrylateYield 83.2%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidCatalyst

Conditions

Temperature
90 °C

Procedure

To 30.0 g (267 mmoles, 3 eq) of 1-octene was added 0.802 g (5.35 mmoles, 0.06 eq) of trifluoromethanesulfonic acid followed by 7.67 g (89.1 mmoles, 1 eq) of methacrylic acid. This mixture was heated to 90° C. for 6 hours. By NMR, the yield was 81% based on acrylic acid consumed. To the reaction mixture was added 36.16 g of a saturated solution of sodium bicarbonate in water (8.28 wt-%, 35.6 mmoles, 0.4 eq) and the mixture was stirred at room temperature for 1 hour. The aqueous phase was removed and the residue was distilled at 25° C./10-20 torr. The receiver was cooled with dry ice to trap the octene. This gave 14 grams of recovered octene. The product was distilled at 103° C./1.0 torr to give 14.7 g of octyl methacrylate (83.2% yield based on acrylic acid consumed).

Workup

  1. customconsumed
  2. customThe aqueous phase was removed
  3. distillationthe residue was distilled at 25° C./10-20 torr
  4. temperatureThe receiver was cooled with dry ice to trap the octene
  5. distillationThe product was distilled at 103° C./1.0 torr

Sources & evidence

ORD record
ord-2e877fc48a304e6baf172528f1b12d6c
Source dataset
uspto-grants-2015_08
Patent number
US09102774B2

Reaction notes

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