Phenol, 4,4′-(1-methylethylidene)bis-, sodium salt (1:2)

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0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous K0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 20percent aqueous KHCO0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isopropyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.021 mole of Na0.01 Mole of bisphenol A, 0.0205 mole of NaOH and 100 mL of n-butyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 50° C. for 4 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 50 mL of hot n-butyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isobutyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isobutyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of n-propyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 3 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot n-propyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of acetone were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot acetone, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 24.6 g of bis-sodium salt of bisphenol A. The yield was 90percent, and the purity was 99.7percent.; EXAMPLE 24; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 18percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 93percent, and the purity was 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous K0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 20percent aqueous KHCO0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isopropyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.021 mole of Na0.01 Mole of bisphenol A, 0.0205 mole of NaOH and 100 mL of n-butyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 50° C. for 4 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 50 mL of hot n-butyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of isobutyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isobutyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of n-propyl alcohol were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 3 hrs, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot n-propyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was measured by titration to be 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 200 mL of acetone were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 60° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot acetone, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 92percent, and the purity was 99.9percent.0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 24.6 g of bis-sodium salt of bisphenol A. The yield was 90percent, and the purity was 99.7percent.; EXAMPLE 24; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 18percent aqueous sodium carbonate solution were charged into a 250 mL three necked flask, and nitrogen gas was bubbled to remove oxygen in the flask. The mixture was allowed to react at 100° C. for 1 hr, and a precipitate was obtained. The precipitate was filtered out under nitrogen atmosphere, washed twice with 30 mL of hot isopropyl alcohol, and then dried under reduced pressure at 200° C. for 3 hrs, to yield 25.0 g of bis-sodium salt of bisphenol A. The yield was 93percent, and the purity was 99.9percent.Example 12Conversion of Treated 4NPI to BisimideA 2-liter, 5-necked oil jacketed glass vessel, equipped with a Dean and Stark receiver topped with a reflux condenser, a mechanical stirrer, and means for maintaining a nitrogen atmosphere, was charged with 335 g (1.63 mol) of 4-NPI in 1000 g of toluene (resulting from the bicarbonate treatment of the 4NPI/water slurry, see above), and 6.2 g (0.008 mol HEG-Cl) of a catalyst solution composed of 34.4percent by wt. HEG-Cl, 10.0percent sodium chloride, and 55.6percent water. An additional 500 g of toluene was added. The solution was brought to reflux using an external hot oil unit set at 120° C. to supply hot oil to the jacket of the vessel, and the water was removed by azeotropic distillation. Approximately 500 g of toluene was removed during the distillation. The dry 4-NPI/catalyst toluene solution was then added via a flexible fitting to a 5-liter, 5-necked oil jacketed glass vessel (equipped with a Dean and Stark Receiver topped with a reflux condenser, mechanical stirrer, and means for maintaining a nitrogen atmosphere) containing 222 g (8.15 mol) of BPA disodium salt and 700 g of toluene (the salt solution can also be added to the NPI solution). The temperature on the 5-liter vessel was maintained at 120° C. using a hot oil recirculating unit. HPLC of the reaction mixture indicated that the displacement reaction was complete in 60 min. to afford a 99.4percent yield of BPA bisimide. The mixture was cooled to 80° C. and extractively purified with three 580 mL portions of 1percent aqueous sodium hydroxide to afford pure bisimide with a yellowness index (YI) of 2.0.The YI was measured with a Macbeth 7000 spectrometer using ASTM D-1925. A blank of methylene chloride was measured for YI prior to measurement of the sample. This YIblank measurement was recorded for use in correcting the final measurement. About 0.5 g of a sample was dissolved into 10 mL of methylene chloride. The sample was then filtered through a 0.5 g HPLC filter. The mixture was then transferred to a 3.7 cm.x.5 cm.x.10 mm path length cell. The cell was placed into the calorimeter (ASTM D11925) and the YI was determined.The equation (I) below was used to correct the YI. This equation (I) is general and allows for solutions to also be measured for YI.YIcor=(YImeas-YIblank)*0.5*100/(wt. Sample in G*percent solids of the sample) (I) The washes were done at 80° C., with a 5 minute agitation time and a 7 minute settling time. The YI of the material was 2.2. The YI of a typical reaction (without bicarbonate treatment of the 4NPI/water slurry) is 3 to 4.EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to It was dried by addition of 12 successive 50-ml portions of dry (maximum 5 ppm water) anisole and distillation under a positive argon atmosphere, and finally reduced again to a paste containing about 10 ml of anisole. A 250 ml three-necked round-bottomed flask, fitted with a stirrer and male joint, was charged with For example, 22.8 g (0.1 mol) of hisphenol-A, 300 mL of dimethylsulfoxide, 100 mL of toluene, and 16.0 g of sodium hydroxide as a 50percent aqueous solution (0.2 mol) is heated to reflux under a nitrogen atmosphere using a Dean Stark trap for 5 hours to remove the water from the system. The toluene is distilled from the vessel after the bulk of the water is removed until the temperature of the reaction mixture exceeds 145° C. In this way, dry The procedure of is repeated, except that o-dichlorobenzene is substituted for the toluene. The disodium salt of bisphenol A is obtained in finely divided form as a slurry in o-dichlorobenzene.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.A dry 100 mL flask was charged with 2.0 g (7.3 mmol) of the

Intermediates

Molecular Weight:272.25
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:272.07891825
Monoisotopic Mass:272.07891825
Topological Polar Surface Area:46.1
Heavy Atom Count:19
Complexity:209
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes