4,4'-Oxydiphthalic anhydride 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

• Language:English Provider:SigmaAldrich

4,4'-Oxydiphthalic anhydride 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.

Flammability and Explosibility

Not classified

Synthesis

The general procedure for the synthesis of 4,4'-oxybisphthalic anhydride from 4-chlorophthalic anhydride is as follows: 1. 4-chlorophthalic anhydride (16 g, 87.7 mmol) was added to a 150 ml three-necked flask fitted with a distillation head, which was pre-filled with about 100 ml of distilled o-dichlorobenzene containing less than 5 ppm of water. 2. The mixture was heated to reflux for 0.5 h under nitrogen protection, followed by distillation to remove about 80 ml of o-dichlorobenzene. 3. To another flask was added powdered potassium carbonate (6.06 g, 43.8 mmol) and 50 ml of anhydrous o-dichlorobenzene. 4. The suspension was heated to reflux for 0.5 h under nitrogen protection and 40 ml of o-dichlorobenzene was distilled. 5. The 4-chlorophthalic anhydride solution prepared in step 1 was transferred to a flask containing potassium carbonate. 6. The mixture was stirred, hexaethylguanidine chloride (468 mg, 1.77 mmol, as an 18% solution in o-dichlorobenzene containing less than 15 ppm of water) was added and refluxing was continued, observing a gradual change in color of the solution to yellow. 7. The mixture was analyzed periodically and 93% yield of 4,4'-oxybisphthalic anhydride was achieved after 3 hours. 8. in a control experiment using the same molar percentage of tetraphenylphosphonium bromide and powdered potassium carbonate it took 13 hours to achieve the same yield. 9. Repeating the experiment, switching to granular potassium carbonate and adjusting the amount of hexaethylguanidine chloride to 2.0 mol% of 4-chlorophthalic anhydride, the product formation was stabilized after 3 hours in an overall yield of about 85% or better. Note: The above description and embodiments are for illustrative purposes only and should not be regarded as a limitation of the present invention. Various modifications, adaptations and substitutions may be made by those skilled in the art without departing from the spirit and scope of the present invention.

IC 50

HepG2: IC50 = 121 μM (human); SK-HEP1: IC50 = 199 μM (human); Hepatocyte: IC50 >200 μM (rat)

References

[1] Patent: US6706897, 2004, B1. Location in patent: Page column 3-4
[2] Patent: CN108250168, 2018, A. Location in patent: Paragraph 0009-0010; 0011-0012; 0013-0014; 0015-0016
[3] Patent: US6727370, 2004, B1. Location in patent: Page column 4
[4] Patent: US6727370, 2004, B1. Location in patent: Page column 4
[5] Patent: US2007/117990, 2007, A1. Location in patent: Page/Page column 12-13

4,4'-Oxydiphthalic anhydride(1823-59-2)Related Product Information

• Phthaloyl dichloride
• Isatoic Anhydride
• CIS-BUTENEDIOIC ANHYDRIDE
• Trifluoromethanesulfonic anhydride
• Caronic anhydride
• Succinic anhydride
• Dibutyl phthalate
• O-Phthalimide
• Glutaric anhydride
• Phthalic anhydride
• PHTHALAMIDE
• 4-Tolyl ether
• 5-Methoxy-isobenzofuran-1,3-dione
• 3,4'-DIMETHYLDIPHENYL ETHER
• 3-Phenoxybenzaldehyde
• Phthalates
• Acetic anhydride
• 4,4'-BIS(METHOXYMETHYL)DIPHENYL ETHER