Itaconic acid → HCID 86676438, compound

HRID 868720Notes

Reaction equation

HRID 868720 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([OH:19])(=[O:18])[C:12]([CH2:14][C:15]([OH:17])=[O:16])=[CH2:13]>C([Sn](=O)CCCC)CCC>[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([OH:19])(=[O:18])[C:12]([CH2:14][C:15]([OH:17])=[O:16])=[CH2:13]

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 12597Isosorbide

Product 1

HCID 86676438HCID 86676438, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 61221Dibutyltin oxideCatalyst

Conditions

Temperature
120 °C

Procedure

To a 3-neck 250 mL round-bottomed flask equipped with a dean stark trap and a condenser was added isosorbide (40.0 g, 273.9 mmol, obtained from Archer Daniels, Midland, Ill.), itaconic acid (32.39 g, 248.9 mmol, obtained from Sigma-Aldrich), and FASCAT 4201 dibutyl tin oxide catalyst (0.07 g, 0.1 wt %, obtained from Arkema Inc.). The mixture was slowly heated under argon to 120° C., during which time the reagents melted. The temperature was then raised to 180° C., and condensation began around 150° C. The reaction mixture was stirred at 180° C. overnight (˜20 h). Thereafter, vacuum (1-2 mm-Hg) was applied for ˜30 min. A total of 3.0 mL water was collected in the dean stark trap. The reaction mixture was cooled under argon to ˜100° C. and discharged into an aluminum tray and cooled to room temperature to give 65 g of product as a glassy material. Tg(DSC)=19.5° C.; viscosity @130° C.=769 cps; viscosity @70° C.=6.63×105 cps. Mn(GPC)=689; Mw(GPC)=1245; Pd(GPC)=1.80.

Workup

  1. customTo a 3-neck 250 mL round-bottomed flask equipped with a dean stark trap and a condenser
  2. temperatureThe temperature was then raised to 180° C.
  3. customcondensation
  4. custombegan around 150° C
  5. waitThereafter, vacuum (1-2 mm-Hg) was applied for ˜30 min
  6. customA total of 3.0 mL water was collected in the dean stark trap
  7. temperatureThe reaction mixture was cooled under argon to ˜100° C.
  8. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-5f30546f6d8d4c51819846e9617029a3
Source dataset
uspto-grants-2015_03
Patent number
US08968452B2

Reaction notes

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