2,2-Bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride

OtherSolid

79 g (0.63 mol) of a 32percent by weight aqueous sodium hydroxide solution and 62.4 g (0.3 mol) of bisphenol A were charged into the reactor.Stir and dissolve, The temperature rises to 85 ° C and the solution is transparent.Next, 510 g of a trimethylbenzene solvent and 4.2 g of a benzyltriethylammonium chloride catalyst were added.Warming and refluxing, The temperature rose to 172 ° C, Stirring reaction for 15 hours, Then cool down to 130 ° C, 108 g (0.6 mol) of 4-chlorophthalic anhydride and 4.86 g of benzyltriethylammonium chloride catalyst were added.Heating from 140 ° C to 145 ° C, Reflow reaction for 5 hours, Then filter hot, Pumping the filtrate into the crystallization kettle, The filtrate is cooled to room temperature.Crystallized for 12 hours, filter, The precipitate is washed with ion-free water, Filtration, precipitation was obtained and washed with 250 g of ethanol.Stirring for 2 hours, filter, Get wet material 125g, After drying, 120 g of bisphenol A diether dianhydride product (yield 85percent), The product is white powder, A dry 100 mL flask was charged with 1.69 g (7.3 mmol) of the disodium salt of biphenol, 2.44 g, (146 mmol) of 4-fluorophthalic anhydride, 2 mL (14 mmol) of hexaethylguanidinium chloride as a 15 weight percent solution in o-dichlorobenzene, and 44 g of dry o-dichlorobenzene. The flask was immersed in an oil bath maintained at 180° C. and the mixture was stirred magnetically. After 15 minutes, the reaction mixture was filtered hot to remove the sodium fluoride by-product. The filtrate was allowed to cool to room temperature and the product dianhydride crystallized from the solvent as a cream colored solid which was isolated by filtration (3.1 g, 90percent yield).A dry 25 mL flask was charged with 403 mg (1.482 mmol) of the disodium salt of bisphenol A, 500 mg (3.012 mmol) of 4-fluorophthalic anhydride, 46 mg (0.148 mmol) of 4-(N, N-dibutylamino)-N-neopentylpyridinium chloride, 8.5 g (10percent solids) of dry o-dichlorobenzene and 55 mg of o-terphenyl (internal standard). The flask was immersed in an oil bath maintained at 180° C. and the mixture was stirred magnetically. The temperature within the reaction flask was about 175° C. Samples (0.1 mL) were withdrawn periodically dissolved in 6 mL of acetic acid and approximately. 0.5 mL of methylamine (40percent aqueous soln.) and heated at 125-130° C. for 1.5 hours. These samples were analyzed for the bis N-methyl imide of bisphenol A dianhydride by liquid chromatography. By following the diether dianhydride formation in this manner it was determined that the yield of product bisphenol A dianhydride (BPADA) had reached 82percent after one hour.A dry 100 mL flask was charged with 2.0 g (7.3 mmol) of the disodium salt of bisphenol A, 2.67 g (14.6 mmol) of 4-chlorophthalic anhydride, 4 mL (14 mmol) of hexaethylguanidinium chloride as a 15 weight percent solution in o-dichlorobenzene, 48 g of dry o-dichlorobenzene, and 100 mg of o-terphenyl (internal standard). The flask was immersed in an oil bath maintained at 180° C. and the mixture was stirred magnetically. The reaction was followed as in Example 1. The yield of biphenol dianhydride had reached 25percent after 5 hours.In a typical procedure, a reactor was charged with 4, 4?-bisphenol A-bis-N- methylphthalimide (which can also include small amounts of 3, 4?-bisphenol A-bis-N- methylphthalimide and 3, 3?-bisphenol A-bis-N-methylphthalimide) (32.93 grams, 0.0602 mole) and phthalic anhydride (29.98 grams, 0.2024 mole). The reaction was conducted in the presence of a triethylamine (TEA) exchange catalyst, which was provided in the form of an aqueous solution having the following composition: 15.1 wt. % triethylamine, and 13.0 wt.% phthalic anhydride, with the balance being water. 23.53 grams of this aqueous solution were added to the exchange reaction. Water was used as the solvent to provide an aqueous reaction mixture having a solids content (%solids) in the range of 13 to 15%. The bisimide/dianhydride exchange reaction was carried out at l70C for 2 hours. For simplicity of the discussion that follows, ?N- methylphthalimide' will be referred to as'PI?, the'4, 4?-bisphenol A-bis-N-methylphthalimide' mixture will be referred to as'BI?, and the'4, 4?-bisphenol A dianhydride' product will be referred to as'DA?.

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

Intermediates

Molecular Weight:520.5
XLogP3:6.5
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:6
Exact Mass:520.11581759
Monoisotopic Mass:520.11581759
Topological Polar Surface Area:105
Heavy Atom Count:39
Complexity:897
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes