Decalin → Ethylene/methyl acrylate methyl cyclohexene methyl acrylate

HRID 11193

Reaction equation

HRID 11193 reaction equation
[CH2:1]1C2C(CCCC2)CC[CH2:2]1.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].[CH3:17][CH:18]1[CH:23](CO)[CH2:22][CH2:21][CH:20]=[CH:19]1>C(Cl)(Cl)Cl>[CH2:1]=[CH2:2].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].[CH3:16][O:15][C:11](=[O:14])[CH:12]=[CH2:13].[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

5

Reactant 3

HCID 7044DecalinHCID 7294Methyl AcrylateHCID 130627053-Methyl-cyclohex-1-ene-4-methanol

Product 1

HCID 86760217Ethylene/methyl acrylate methyl cyclohexene methyl acrylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
170 °C

Procedure

550 ml of decalin® was placed in a flask. To this was added 350 g of Chevron EMAC SP-2260 which has 24 weight % of methyl acrylate (0.9767 moles of methyl acrylate) and 0.48 g of Irganox®1076 (0.1 mole). The temperature of the mixture was gradually raised while stirring. When the temperature reached approximately 120° C., 127.1 g (0.9767 moles) of 3-methyl-cyclohex-1-ene-4-methanol (97%) was added. When the temperature reached approximately 140° C., 4.8 g of the catalyst Ti(OC2H5)4 was added a portion at a time. The temperature was maintained at 170° C. while stirring. The course of the reaction was observed by subjecting samples of the mixture to NMR at hourly intervals. The percent conversion is given in Table 1 below. After 5 hours of reaction, the mixture was cooled and 400 ml of CHCl3 was added and the mixture was then precipitated by adding it to 4 liters of CH3OH in a Waring blender. The precipitate is filtered and washed with CH3OH and dried in a vacuum oven at 50° C. The dried mixture yielded 407.5 g of ethylene/methyl acrylate/methyl cyclohexene methyl acrylate (EMCM).

Workup

  1. additionTo this was added 350 g of Chevron EMAC SP-2260 which
  2. temperatureThe temperature of the mixture was gradually raised
  3. customreached approximately 120° C.
  4. customreached approximately 140° C.
  5. stirringwhile stirring
  6. customAfter 5 hours of reaction
  7. temperaturethe mixture was cooled
  8. customthe mixture was then precipitated
  9. additionby adding it to 4 liters of CH3OH in a Waring blender
  10. filtrationThe precipitate is filtered
  11. washwashed with CH3OH
  12. customdried in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-eba59b58661c4797b82e6da436495a6a
Source dataset
uspto-grants-2006_08
Patent number
US07097890B1

Linked notes

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