ChemicalBook Product Catalog Chemical Reagents Organic reagents Ethers 4,4'-Oxydiphthalic anhydride

4,4'-Oxydiphthalic anhydride

Product Name4,4'-Oxydiphthalic anhydride
CAS1823-59-2
MFC16H6O7
MW310.21
EINECS412-830-4
MOL File1823-59-2.mol

Chemical Properties

Melting point	225-229 °C(lit.)
Boiling point	410.39°C (rough estimate)
Density	1.4942 (rough estimate)
refractive index	1.6380 (estimate)
storage temp.	Inert atmosphere,Room Temperature
solubility	very slightly in Toluene,Acetone
form	powder to crystal
color	White to Light yellow to Light orange
InChI	InChI=1S/C16H6O7/c17-13-9-3-1-7(5-11(9)15(19)22-13)21-8-2-4-10-12(6-8)16(20)23-14(10)18/h1-6H
InChIKey	QQGYZOYWNCKGEK-UHFFFAOYSA-N
SMILES	O(C1C=CC2C(=O)OC(=O)C=2C=1)C1C=CC2C(=O)OC(=O)C=2C=1
CAS DataBase Reference	1823-59-2(CAS DataBase Reference)
NIST Chemistry Reference	Bis-(3-phthalyl anhydride) ether(1823-59-2)
EPA Substance Registry System	1,3-Isobenzofurandione, 5,5'-oxybis- (1823-59-2)

Safety Information

Risk Statements	52/53
Safety Statements	61
WGK Germany	2
HS Code	29189900

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

4,4'-Oxydiphthalic anhydride/ODPA(CAS:1823-59-2) is a solid, melts in the range of 225-229 °C and was first introduced in the mid-1980s, offering a greater degree of flexibility than other commercial dianhydrides. It also is somewhat less reactive than BTDA. ODPA has largely been used in polyimides and much less so in epoxies. It imparts special performance properties in free films and in FCCL production for high-end personal electronic devices.

Chemical Properties

off-white to white powder

Uses

4,4'-oxydiphthalic anhydride be used for the preparation of a polyimide material.

Preparation

The preparation of 4,4'-Oxydiphthalic anhydride is as follows:Chlorophthalic anhydride (30g, 160mmol), tetraphenyl phosphonium bromide (0.3g, 0.7mmol), and 2,5-dichlorobenzoic acid (0.08g, 0.4mmol) were heated to approximately 220℃. Potassium carbonate (7.95g, 58mmol) was added over 45 minutes. The reaction was sampled after addition of the potassium carbonate and showed a 24.9% conversion to 4,4'-oxydiphthalic anhydride. The reaction was heated for an additional 45 minutes. The reaction mixture was diluted with 1,2,4-trichlorobenzene (90g) and filtered. The 4,4'-oxydiphthalic anhydride was allowed to crystallize and was collected, washed with 1,2,4-trichlorobenzene followed by hexane, and dried in an air circulating oven at 120℃. to give crude 4,4'-oxydiphthalic anhydride, 12.9g.