Water → allylsuccinat

Water (321 g, 321 mL, 1.78 moles) was placed in a 1 L, 3-neck RBF and briefly vacuumed to remove oxygen. Then allyl succinic anhydride (50 g, 42.7 mL, 357 mmoles) was added and the reaction solution heated to 110 C overnight. The reaction solution was then cooled to room temperature and the volatiles removed from a sample to prepare for FTIR analysis. After confirming the anhydride had been converted to carboxylic acid, the volatiles were removed by vacuum transfer while stirring the reaction solution at 30 C. The reaction flask temperature was maintained with a temperature controller while being monitored using a thin wire thermocouple placed between the heating mantle and reaction flask. As the product began to solidify, the solids were broken up to facilitate drying. After the majority of the water had been removed, the flask was connected directly to the Schlenk line to achieve a pressure <20 mtorr overnight. The product is a white solid (55.6 g, 352 mmoles, 98.5% yield). 1H NMR (DMSO-d6, δ): 2.07 to 2.35 and 2.42 to 2.52 (m, 4H, CH2═CHCH2CH(CO2H)CH2CO2H), 2.66 to 2.74 (m, 1H, CH2CH(CO2H)CH2), 5.00 to 5.09 (m, 2H, CH2═CHCH2) 5.6 to 5.78 (m, 1H, CH2═CHCH2CH). IR (cm−1, diamond): 2300 to 3700 (broad CO2H), 3029 w (sp2 C—H), 2978w, 2921w (sp3 C—H), 1689 s (C═O).

1. customto remove oxygen
2. temperaturethe reaction solution heated to 110 C overnight
3. customthe volatiles removed from a sample
4. customto prepare for FTIR analysis
5. customthe volatiles were removed by vacuum transfer
6. temperatureThe reaction flask temperature was maintained with a temperature controller
7. customthermocouple placed between the heating mantle and reaction flask
8. customto facilitate drying
9. customAfter the majority of the water had been removed
10. customa pressure <20 mtorr overnight

ORD-Eintrag

ord-a8cc8c3ecf4b4955ad022a7f31b6237c

Quelldatensatz

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09139770B2