4,4'-(4,4'-ISOPROPYLIDENEDIPHENOXY)BIS(PHTHALIC ANHYDRIDE) Chemical Properties

Melting point:

184-187 °C(lit.)

Boiling point:

712.3±60.0 °C(Predicted)

Density 

1.406±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Light yellow

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C31H20O8/c1-31(2,17-3-7-19(8-4-17)36-21-11-13-23-25(15-21)29(34)38-27(23)32)18-5-9-20(10-6-18)37-22-12-14-24-26(16-22)30(35)39-28(24)33/h3-16H,1-2H3

InChIKey

MQAHXEQUBNDFGI-UHFFFAOYSA-N

SMILES

C(C1=CC=C(OC2C=CC3C(=O)OC(=O)C=3C=2)C=C1)(C1=CC=C(OC2C=CC3C(=O)OC(=O)C=3C=2)C=C1)(C)C

LogP

-2.22 at 21℃

EPA Substance Registry System

1,3-Isobenzofurandione, 5,5'-[(1-methylethylidene)bis(4,1-phenyleneoxy)]bis- (38103-06-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-42

Safety Statements 

26-36

WGK Germany 

3

RTECS 

NP7227500

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich

4,4'-(4,4'-ISOPROPYLIDENEDIPHENOXY)BIS(PHTHALIC ANHYDRIDE) Usage And Synthesis

Description

4,4'-(4,4'-Isopropylidenediphenoxy)diphthalic Anhydride (BPADA) is a diphthalic anhydride structural unit with a core of bisphenol A. BPADA is a precursor for the synthesis of polyimides, which are highly thermally stable and have strong mechanical properties using their bisphenol A core. Polyimide films synthesised from this molecule are incompletely conjugated and therefore have high optical transparency. With their isometric stretchability and high glass transition temperature (Tg = 207 °C), these films are ideal for flexible display substrates. In addition to their high heat resistance, the polyimides are chemically inert and can be used as ion transport membranes in fuel cells.BPADA can also be used to make aerogels that are superhydrophobic (Lotus effect).

Uses

4,4'-(4,4'-Isopropylidenediphenoxy)bis(phthalic anhydride) be used for the preparation of a polyimide material.

Preparation

4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic anhydride) can be synthesized from 4-chlorophthalic anhydride and bisphenol A. Mainly includes the following steps:(1) Chlorophenyl anhydride imide, synthesis of N-Phenyltetrachlorophthalimide;(2) the synthesis of bisphenol A disodium salt;(3) Nucleophilic substitution reaction in dipolar nonproton solvent;(4) hydrolysis to bisphenol A diether tetraic acid;(5) dehydration to 4,4'-(4,4'-isopropylidenediphenoxy)bis(phthalic anhydride).

Flammability and Explosibility

Not classified

Synthesis

The general procedure for synthesizing bisphenol A-type diethyl ether dianhydride from bisphenol A and 4-chlorophthalic anhydride is as follows: 79 g (0.63 mol) of 32 wt.% aqueous sodium hydroxide and 62.4 g (0.3 mol) of bisphenol A are added to a reactor, and stirred until completely dissolved. The reaction mixture was heated to 85°C, at which point the solution should appear clear. Subsequently, 510 g of trimethylbenzene was added as solvent and 4.2 g of benzyltriethylammonium chloride as catalyst. The reaction was started at room temperature, gradually warmed up to 172°C and continued stirring at this temperature for 15 hours. Upon completion of the reaction, the reaction mixture was cooled to 130 °C and 108 g (0.6 mol) of 4-chlorophthalic anhydride and 4.86 g of benzyltriethylammonium chloride catalyst were added. The reaction mixture was heated to 140°C to 145°C and kept at reflux for 5 hours. At the end of the reaction, it was filtered while hot and the filtrate was transferred to a crystallization kettle, cooled to room temperature and left to crystallize for 12 hours. After crystallization was completed, the precipitate was collected by filtration, washed with non-ionic water and filtered again. The precipitate was washed with 250 g of ethanol, stirred for 2 h and filtered to obtain 125 g of wet material. 120 g of bisphenol A diethyl ether dianhydride product was obtained after drying in 85% yield. The final product was in the form of white powder.

References

[1] Patent: CN108148029, 2018, A. Location in patent: Paragraph 0011; 0012; 0014

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