Phthalic Anhydride → Glycidyl neodecanoate

HRID 1289261Notes

Reaction equation

HRID 1289261 reaction equation
C(O)COCCO[CH2:7][CH2:8][OH:9].[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[CH3:22][CH:23]1CC=CC2C(OC(=O)C12)=O.[C:34]1(O)C(=CC(=CC=1)O)C.C1(=O)OC(=O)C=C1>C(O)COCCO>[CH3:22][CH2:23][CH2:20][CH2:19][CH2:18][CH2:17][C:13]([C:14]([O:16][CH2:11][CH:8]1[O:9][CH2:7]1)=[O:15])([CH3:12])[CH3:34]

Participants

7

Reactant 5

HCID 6811Phthalic AnhydrideHCID 7253MethylhydroquinoneHCID 7923Maleic AnhydrideHCID 8172Triethylene GlycolHCID 127266034-Methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione

Product 1

HCID 33600Glycidyl neodecanoate

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
205 °C

Procedure

593 parts of triethylene glycol, 206 parts of diethylene glycol, 305 parts of phthalic anhydride, 490 parts of 3-methyltetrahydrophthalic anhydride and 0.158 parts of toluhydroquinone were placed in a 2 liter flask containing four openings equipped with a thermometer, stirrer, inert gas introduction opening, and reflux condenser, respectively. The mixture was heated to 205° C. under a nitrogen atmosphere and allowed to react for 15 hours; upon reaching a solid acid value of 15, the mixture was cooled to 120° C. followed by addition of 87 parts of maleic anhydride. The temperature was then raised to 190° C. and allowed to react for 5 hours until reaching a solid acid value of 24, at which point it was cooled to 160° C. After 148 parts of CARDURA E-10 (an epoxy compound produced by Shell Chemicals Co., Ltd.) were added and allowed to react for 3 hours at 130° C., 1078 parts of dipropylene glycol monomethylether methacrylate were then added to produce a resin composition with a nonvolatile content of 60.0%, an acid value of 1.1 and a Gardner viscosity of S-T. 80 parts of the resin of Example 10 were then added to 20 parts of the above resin to produce a resin composition with a nonvolatile content of 60.0%, an acid value of 2.9 and a Gardner viscosity of P-Q. The resultant resin composition was then placed through the same evaluation tests as in Example 7, and the results are shown in Table 2.

Workup

  1. additioncontaining four openings
  2. customequipped with a thermometer, stirrer, inert gas introduction opening
  3. temperaturereflux condenser
  4. customto react for 15 hours
  5. temperaturethe mixture was cooled to 120° C.
  6. temperatureThe temperature was then raised to 190° C.
  7. customto react for 5 hours
  8. temperatureat which point it was cooled to 160° C

Sources & evidence

ORD record
ord-64131b7cf14a411ca8a1539fae18239c
Source dataset
uspto-grants-1998_05
Patent number
US05747597

Reaction notes

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