3,4'-Oxydiphthalic Anhydride Chemical Properties

Melting point:

180 °C

Boiling point:

554.4±35.0 °C(Predicted)

Density 

1.665

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

powder to crystal

color 

White to Orange to Green

InChI

InChI=1S/C16H6O7/c17-13-8-5-4-7(6-10(8)15(19)22-13)21-11-3-1-2-9-12(11)16(20)23-14(9)18/h1-6H

InChIKey

OPVHOFITDJSMOD-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(OC3C=CC4C(=O)OC(=O)C=4C=3)=CC=C2)C(=O)O1

Safety Information

HS Code 

29329990

3,4'-Oxydiphthalic Anhydride Usage And Synthesis

Appearance

White to Orange to Green powder to crystal

Uses

4-[(1,3-Dihydro-1,3-dioxo-5-isobenzofuranyl)oxy]-1,3-isobenzofurandione is a useful research chemical.

Uses

3,4'-Oxydiphthalic Anhydride (α-ODPA) can be used to prepare polyimides. The polymer is widely used in silicon-based anode plates, resin films and filler materials for high-performance lithium-ion batteries.

Synthesis

2,2',3,3'-ODPA and 2,3,3',4'-ODPA are synthesised using 3-Chlorophthalic anhydride as a raw material by chemical reaction^[1]. The specific synthesis steps are as follows:
Step1: 3-Chlorophthalic anhydride (348.83 g) was taken in a 2000-mL, three-necked, round-bottom flask fitted with a mechanical stirrer and a reflux condenser. About 1100 mL of glacial acetic acid were added. It was stirred for 20 min at 50 °C to dissolve the anhydride completely. Then, 198 g of aqueous methylamine solution (ca. 59.35 g of methylamine) were dropped in the flask. The resulting mixture was heated to reflux for 4 h and subsequently cooled to room temperature. The white crystals were filtered and dried; 314 g were obtained (yield: 84%, mp: 101–103 °C).
Step2: 3-(2,3-Dimethylphenoxy) phthalic acid (32.90 g) and potassium hydroxide (10.4 g) were dissolved in 1000 mL of water, and the solution was heated to about 80 °C. Then, solid potassium permanganate (116.6 g) was added gradually several times until the purple did not fade within 30 min. After reflux for 5 h, the excess potassium permanganate was destroyed with ethanol. The filtrate was acidified to a pH of 1 after concentration to 200 mL and cooled to room temperature. The acid solution was allowed to stand overnight, and the white precipitation was collected by filtration and dried and then purified by sublimation at 267 °C in vacuo. About 31.35 g of dianhydride (yield: 88%) were obtained; mp: 243–244 °C (lit.16 236 – 238 °C, lit.18 237 °C). IR (KBr): 1860, 1786 (CAO str), 1261 (asym COO str), 1048 cm1 (sym COO str). 1 H NMR (300 M, DMSO):  (ppm), 8.03– 8.01 (d, 2H), 7.98 – 7.92 (t, 2H), 7.60 –7.57 (d, 2H). ELEM. ANAL. Calcd. for C16H6O7: C, 61.95%; H, 1.95%. Found: C, 61.87%; H, 1.93%.
Step3: The reactions were the as same as the synthesis of 2,2,
3,3
-ODPA except for the replacement of 2,3-xylenol as 3,4-xylenol. The final dianhydride was recrystallized from the mixed solvents of acetic anhydride and toluene; mp: 177–178 °C (lit.16 174 –175.5 °C, lit.18 170 °C). IR (KBr): 1854, 1770 (CAO str), 1265 (asym COO str), 1081 (sym COO str) cm1 . 1 H NMR (300 MHz, DMSO-d6):  (ppm) 8.17– 8.14 (d, 1H), 8.10 – 8.08 (d, 1H), 8.05– 8.00 (t, 1H), 7.75–7.74 (d, 1H), 7.71 (s, 1H), 7.70 –7.68 (d, 1H). ELEM. ANAL. Calcd. for C16H6O7: C, 61.95%; H, 1.95%. Found: C, 61.90%; H, 1.97%.

References

[1] QINGXUAN LI. Polyimides from isomeric oxydiphthalic anhydrides[J]. Journal of Polymer Science Part A: Polymer Chemistry, 2003. DOI:10.1002/pola.10918.

3,4'-Oxydiphthalic Anhydride(50662-95-8)Related Product Information

• bicyclo[2.2.1]heptanebis(methylamine)