[ CAS No. 2444-90-8 ] {[proInfo.proName]}

Name: 2444-90-8|Sodium 4,4'-(propane-2,2-diyl)diphenolate|95%
Brand: Ambeed
SKU: A190059
Rating: 90 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 2444-90-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2444-90-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2444-90-8 ]

SDS Specification

Alternatived Products of [ 2444-90-8 ]

Product Details of [ 2444-90-8 ]

CAS No. :	2444-90-8	MDL No. :	MFCD01763349
Formula :	C₁₅H₁₄Na₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WGMBWDBRVAKMOO-UHFFFAOYSA-L
M.W :	272.25	Pubchem ID :	17127
Synonyms :

Calculated chemistry of [ 2444-90-8 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.2
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.66
TPSA :	46.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-20.85
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	4.3
Log Po/w (MLOGP) :	3.2
Log Po/w (SILICOS-IT) :	3.29
Consensus Log Po/w :	-1.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.95
Solubility :	0.0302 mg/ml ; 0.000111 mol/l
Class :	Soluble
Log S (Ali) :	-3.96
Solubility :	0.0295 mg/ml ; 0.000108 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.59
Solubility :	0.00692 mg/ml ; 0.0000254 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.52

Safety of [ 2444-90-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2444-90-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2444-90-8 ]
Downstream synthetic route of [ 2444-90-8 ]

[ 2444-90-8 ] Synthesis Path-Upstream 1~3

1
[ 80-05-7 ]
[ 2444-90-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; potassium carbonate In water at 100℃; for 1 h;	0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous K₂CO₃solution 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.; EXAMPLE 27; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 35percent aqueous K₂CO₃solution 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
95%	With sodium hydroxide; potassium hydrogencarbonate In water at 100℃; for 1 h;	0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 20percent aqueous KHCO₃solution 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
94%	With sodium hydroxide In isopropyl alcohol at 60℃; for 1 h;	0.01 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.

94%	With sodium hydrogencarbonate; sodium carbonate In water at 100℃; for 1 h;	0.01 Mole of bisphenol A, 0.021 mole of Na₂CO₃and 200 mL of 8.4percent aqueous sodium bicarbonate 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 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.
94%	With sodium hydroxide In butan-1-ol at 50℃; for 4 h;	0.01 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.
94%	With sodium hydroxide In 2-methyl-propan-1-ol at 60℃; for 1 h;	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.
92%	With sodium hydroxide In propan-1-ol at 60℃; for 3 h;	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.
92%	With sodium hydroxide In acetone at 60℃; for 1 h;	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.
90%	With sodium hydroxide; sodium carbonate In water at 100℃; for 1 h;	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.

Reference： [1] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4-5
[2] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4
[3] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2
[4] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4
[5] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 3
[6] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2
[7] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 2
[8] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 3
[9] Patent: US2005/272957, 2005, A1, . Location in patent: Page/Page column 4
[10] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 10, p. 1953 - 1956[11] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 10, p. 2175 - 2178
[12] Patent: US2005/49439, 2005, A1, . Location in patent: Page/Page column 12; 13
[13] Patent: US4202993, 1980, A,
[14] Patent: WO2015/160931, 2015, A1, . Location in patent: Paragraph 0067

2
[ 319-03-9 ]
[ 2444-90-8 ]
[ 38103-06-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 180℃; for 0.25 h;	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).
82%	at 175℃; for 1 h;	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.

Reference： [1] Patent: US2006/205958, 2006, A1, . Location in patent: Page/Page column 6
[2] Patent: US2006/205958, 2006, A1, . Location in patent: Page/Page column 5; 6

3
[ 118-45-6 ]
[ 2444-90-8 ]
[ 38103-06-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	at 180℃; for 5 h;	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.

Reference： [1] Patent: US2006/205958, 2006, A1, . Location in patent: Page/Page column 6

[ 2444-90-8 ] Synthesis Path-Downstream 1~16

1
[ 80-05-7 ]
[ 2444-90-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; potassium carbonate; In water; at 100℃; for 1.0h;Product distribution / selectivity;	0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 10percent aqueous K2CO3 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.; EXAMPLE 27; 0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 35percent aqueous K2CO3 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
95%	With sodium hydroxide; potassium hydrogencarbonate; In water; at 100℃; for 1.0h;Product distribution / selectivity;	0.01 Mole of bisphenol A, 0.02 mole of NaOH and 150 mL of 20percent aqueous KHCO3 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 25.8 g of bis-sodium salt of bisphenol A. The yield was 95percent.
94%	With sodium hydroxide; In isopropyl alcohol; at 60℃; for 1.0h;	0.01 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.

94%	With sodium hydrogencarbonate; sodium carbonate; In water; at 100℃; for 1.0h;Product distribution / selectivity;	0.01 Mole of bisphenol A, 0.021 mole of Na2CO3 and 200 mL of 8.4percent aqueous sodium bicarbonate 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 25.6 g of bis-sodium salt of bisphenol A. The yield was 94percent, and the purity was 99.9percent.
94%	With sodium hydroxide; In butan-1-ol; at 50℃; for 4.0h;Product distribution / selectivity;	0.01 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.
94%	With sodium hydroxide; In 2-methyl-propan-1-ol; at 60℃; for 1.0h;Product distribution / selectivity;	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.
92%	With sodium hydroxide; In propan-1-ol; at 60℃; for 3.0h;Product distribution / selectivity;	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.
92%	With sodium hydroxide; In acetone; at 60℃; for 1.0h;Product distribution / selectivity;	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.
90 - 93%	With sodium hydroxide; sodium carbonate; In water; at 100℃; for 1.0h;Product distribution / selectivity;	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.
	With sodium hydroxide;	EXAMPLE 1 A mixture of 2.020 parts of bisphenol-A, 1.407 part of a 50.3percent aqueous sodium hydroxide solution and 1.93 part of water was briefly heated to a boil. The resulting fluid slurry of the bisphenol-A disodium salt was spread over a nickle coated brass sheet on a hot plate which was inside of a dry box and which was preheated at 300° to 320° C. Evaporation of the water was instantaneous, resulting in a white powdery solid.
	With sodium hydroxide; In water; at 80℃; for 1.0h;Inert atmosphere; Dean-Stark;	Example 6: Synthesis of Na2BPA Slurry in DPS using BPA, aq NaOH, xylenes and DPS and polymerization with C1PAMI A 500 mL 3-neck round bottomed flask (24/40) was equipped with an overhead stirrer. The flask was also connected to a nitrogen sweep and a nitrogen blanket. The nitrogen blanket was connected to a bubbler via a Dean-Stark trap with its arm wrapped in a heating tape. The flask was then charged with 11.4145 g BPA (0.05 moles, 1 equiv.) and 0.1 moles aqueous NaOH solution. The overhead stirrer was turned on and the flask was immersed into the oil bath at 80°C. The stirring was continued for lh. Another 500 mL 3- neck flask with the above set-up was charged with 200 mL xylenes and heated to 140°C. The aqueous salt solution was slowly cannulated into the flask containing heated xylenes stripping off the water into the Dean-Stark trap. After removing majority of the water, the salt solution turned into a slurry. Once the salt is free of water, diphenyl sulfone (DPS) (100 g) was added to the slurry and xylenes was completely stripped off providing a Na2BPA slurry in DPS.

Reference： [1]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 4-5
[2]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 4
[3]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 2
[4]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 4
[5]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 3
[6]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 2
[7]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 2
[8]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 3
[9]Patent: US2005/272957,2005,A1 .Location in patent: Page/Page column 4
[10]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178
[11]Patent: US2005/49439,2005,A1 .Location in patent: Page/Page column 12; 13
[12]Patent: US4202993,1980,A
[13]Patent: WO2015/160931,2015,A1 .Location in patent: Paragraph 0067

2
[ 118-74-1 ]
[ 2444-90-8 ]
[ 110299-20-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1953 - 1956
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2175 - 2178

3
[ 2444-90-8 ]
N-phenyl-3-nitrophthalimide [ No CAS ]
[ 54395-38-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2099 - 2103

4
[ 116-14-3 ]
[ 124-38-9 ]
[ 2444-90-8 ]
[ 77-78-1 ]
[ 131043-00-0 ]
[ 131042-99-4 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 146 - 151

5
[ 79-38-9 ]
[ 124-38-9 ]
[ 2444-90-8 ]
[ 77-78-1 ]
[ 131043-06-6 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 146 - 151

6
[ 2444-90-8 ]
[ 131043-07-7 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 146 - 151

7
[ 2444-90-8 ]
[ 131043-08-8 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 146 - 151

8
[ 80-00-2 ]
[ 2444-90-8 ]
[ 90139-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	CH3O3S(1-)*C13H38N7P2(1+); In 1,2-dichloro-benzene; at 180℃; for 4.0h;Heating / reflux;Conversion of starting material;	General Procedure for Model Reactions (Displacement Reactions of 4-Chlorophenyl Phenyl Sulfone); Dry <strong>[2444-90-8]bisphenol A disodium salt</strong> (BPANa2) was weighed into a 50-mL flask, and a 2 mole percent excess of 4-chlorophenyl phenyl sulfone was added. The transfers were carried out in a dry box. The flask was capped, removed from the dry box, and was fitted with a condenser and a nitrogen purge. Sufficient solvent was added to achieve a final product concentration to approximately 20 weight percent, assuming quantitative conversion of starting materials to product. Phenanthrene was added (typically 100 mg) as an internal standard. The reaction mixture was stirred magnetically while being heated to reflux. Once reflux had been achieved, the phase transfer catalyst (PTC) was added, and the timer was started. Samples were removed periodically, and were analyzed by HPLC.FIGS. 1 and 2 illustrate the behavior of the new phase transfer catalysts in the formation of 1,1'-(1-methylethylidene)bis[4-[4-(phenylsulfonyl)phenoxy]benzene (CAS No. 90139-53-0). When the P2-EthylMethyl mesylate was used as a PTC at 1.0 mole percent in the model reaction in refluxing o-DCB at 180° C. (See 4 (FIG. 1)), the reaction exhibited pseudo-first order kinetics. This indicates that no catalyst decomposition nor diminution in rate was occurring during the reaction. In order to further test the stability of the phosphazenium salt, similar reactions were carried out at higher temperatures, in 3,4-dichlorotoluene (bp=200° C.) (See 6 (FIG. 1)) and in 1,2,4-trichlorobenzene (bp=214° C.) (See 2 (FIG. 1)). As shown in FIG. 1, even at 200° C., essentially linear reaction kinetics were observed, indicating no decomposition of the P2-EthylMethyl mesylate phase transfer catalyst. In trichlorobenzene, only a small amount of decomposition was observed, after 60 minutes (See 2 (FIG. 1)). In this instance only 0.5 mole percent catalyst was used, since after initial range-finding experiments it was determined that reaction using 1.0 mole percent would be too fast to follow accurately at 214° C. The results shown in FIG. 1 illustrate that because they are highly stable, the phosphazenium salt phase transfer catalysts are effective over a broad range of temperatures. Under the reaction conditions examined (2, 4, 6 FIG. 1) the stability of the phosphazenium salt catalyst was observed to be superior relative to a representative guanidinium salt phase transfer catalyst, hexaethylguanidium chloride (HEGCl). FIG. 2 illustrates the enhanced stability of the phosphazenium catalysts and compares a reaction utilizing HEGCl in o-DCB at 180° C. (See 10 FIG. 2) to the same reaction using a phosphazenium catalyst at either 180° C. (See 20 FIG. 2) or at 200° C. (See 30 FIG. 2). Although HEGCl provides a faster initial rate (See 12 FIG. 2) than the phosphazenium salt at 180° C. (See 22 FIG. 2), the reactions incorporating a phosphazenium salt phase transfer catalyst ultimately give higher yields (Compare 18, 28, and 36 FIG. 2). At 200° C. (30, FIG. 2), the rate increase obtained by increasing the reaction temperature more than compensates for the relative effectiveness of the catalysts, and reaction rates faster than could be achieved with HEGCl were obtained (Compare 12 and 32 FIG. 2).
	1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In 1,2-dichloro-benzene; at 180 - 200℃; for 0.5h;Heating / reflux;Conversion of starting material;	General Procedure for Model Reactions (Displacement Reactions of 4-Chlorophenyl Phenyl Sulfone); Dry <strong>[2444-90-8]bisphenol A disodium salt</strong> (BPANa2) was weighed into a 50-mL flask, and a 2 mole percent excess of 4-chlorophenyl phenyl sulfone was added. The transfers were carried out in a dry box. The flask was capped, removed from the dry box, and was fitted with a condenser and a nitrogen purge. Sufficient solvent was added to achieve a final product concentration to approximately 20 weight percent, assuming quantitative conversion of starting materials to product. Phenanthrene was added (typically 100 mg) as an internal standard. The reaction mixture was stirred magnetically while being heated to reflux. Once reflux had been achieved, the phase transfer catalyst (PTC) was added, and the timer was started. Samples were removed periodically, and were analyzed by HPLC.
	CH3O3S(1-)*C13H38N7P2(1+); In 1,2,4-Trichlorobenzene; at 214℃; for 2.0h;Heating / reflux;Conversion of starting material;	General Procedure for Model Reactions (Displacement Reactions of 4-Chlorophenyl Phenyl Sulfone); Dry <strong>[2444-90-8]bisphenol A disodium salt</strong> (BPANa2) was weighed into a 50-mL flask, and a 2 mole percent excess of 4-chlorophenyl phenyl sulfone was added. The transfers were carried out in a dry box. The flask was capped, removed from the dry box, and was fitted with a condenser and a nitrogen purge. Sufficient solvent was added to achieve a final product concentration to approximately 20 weight percent, assuming quantitative conversion of starting materials to product. Phenanthrene was added (typically 100 mg) as an internal standard. The reaction mixture was stirred magnetically while being heated to reflux. Once reflux had been achieved, the phase transfer catalyst (PTC) was added, and the timer was started. Samples were removed periodically, and were analyzed by HPLC.FIGS. 1 and 2 illustrate the behavior of the new phase transfer catalysts in the formation of 1,1'-(1-methylethylidene)bis[4-[4-(phenylsulfonyl)phenoxy]benzene (CAS No. 90139-53-0). When the P2-EthylMethyl mesylate was used as a PTC at 1.0 mole percent in the model reaction in refluxing o-DCB at 180° C. (See 4 (FIG. 1)), the reaction exhibited pseudo-first order kinetics. This indicates that no catalyst decomposition nor diminution in rate was occurring during the reaction. In order to further test the stability of the phosphazenium salt, similar reactions were carried out at higher temperatures, in 3,4-dichlorotoluene (bp=200° C.) (See 6 (FIG. 1)) and in 1,2,4-trichlorobenzene (bp=214° C.) (See 2 (FIG. 1)). As shown in FIG. 1, even at 200° C., essentially linear reaction kinetics were observed, indicating no decomposition of the P2-EthylMethyl mesylate phase transfer catalyst. In trichlorobenzene, only a small amount of decomposition was observed, after 60 minutes (See 2 (FIG. 1)). In this instance only 0.5 mole percent catalyst was used, since after initial range-finding experiments it was determined that reaction using 1.0 mole percent would be too fast to follow accurately at 214° C. The results shown in FIG. 1 illustrate that because they are highly stable, the phosphazenium salt phase transfer catalysts are effective over a broad range of temperatures. Under the reaction conditions examined (2, 4, 6 FIG. 1) the stability of the phosphazenium salt catalyst was observed to be superior relative to a representative guanidinium salt phase transfer catalyst, hexaethylguanidium chloride (HEGCl). FIG. 2 illustrates the enhanced stability of the phosphazenium catalysts and compares a reaction utilizing HEGCl in o-DCB at 180° C. (See 10 FIG. 2) to the same reaction using a phosphazenium catalyst at either 180° C. (See 20 FIG. 2) or at 200° C. (See 30 FIG. 2). Although HEGCl provides a faster initial rate (See 12 FIG. 2) than the phosphazenium salt at 180° C. (See 22 FIG. 2), the reactions incorporating a phosphazenium salt phase transfer catalyst ultimately give higher yields (Compare 18, 28, and 36 FIG. 2). At 200° C. (30, FIG. 2), the rate increase obtained by increasing the reaction temperature more than compensates for the relative effectiveness of the catalysts, and reaction rates faster than could be achieved with HEGCl were obtained (Compare 12 and 32 FIG. 2).

CH3O3S(1-)*C13H38N7P2(1+); In 3,4-Dichlorotoluene; at 200℃; for 1.0h;Heating / reflux;Conversion of starting material;

General Procedure for Model Reactions (Displacement Reactions of 4-Chlorophenyl Phenyl Sulfone); Dry <strong>[2444-90-8]bisphenol A disodium salt</strong> (BPANa2) was weighed into a 50-mL flask, and a 2 mole percent excess of 4-chlorophenyl phenyl sulfone was added. The transfers were carried out in a dry box. The flask was capped, removed from the dry box, and was fitted with a condenser and a nitrogen purge. Sufficient solvent was added to achieve a final product concentration to approximately 20 weight percent, assuming quantitative conversion of starting materials to product. Phenanthrene was added (typically 100 mg) as an internal standard. The reaction mixture was stirred magnetically while being heated to reflux. Once reflux had been achieved, the phase transfer catalyst (PTC) was added, and the timer was started. Samples were removed periodically, and were analyzed by HPLC.FIGS. 1 and 2 illustrate the behavior of the new phase transfer catalysts in the formation of 1,1'-(1-methylethylidene)bis[4-[4-(phenylsulfonyl)phenoxy]benzene (CAS No. 90139-53-0). When the P2-EthylMethyl mesylate was used as a PTC at 1.0 mole percent in the model reaction in refluxing o-DCB at 180° C. (See 4 (FIG. 1)), the reaction exhibited pseudo-first order kinetics. This indicates that no catalyst decomposition nor diminution in rate was occurring during the reaction. In order to further test the stability of the phosphazenium salt, similar reactions were carried out at higher temperatures, in 3,4-dichlorotoluene (bp=200° C.) (See 6 (FIG. 1)) and in 1,2,4-trichlorobenzene (bp=214° C.) (See 2 (FIG. 1)). As shown in FIG. 1, even at 200° C., essentially linear reaction kinetics were observed, indicating no decomposition of the P2-EthylMethyl mesylate phase transfer catalyst. In trichlorobenzene, only a small amount of decomposition was observed, after 60 minutes (See 2 (FIG. 1)). In this instance only 0.5 mole percent catalyst was used, since after initial range-finding experiments it was determined that reaction using 1.0 mole percent would be too fast to follow accurately at 214° C. The results shown in FIG. 1 illustrate that because they are highly stable, the phosphazenium salt phase transfer catalysts are effective over a broad range of temperatures. Under the reaction conditions examined (2, 4, 6 FIG. 1) the stability of the phosphazenium salt catalyst was observed to be superior relative to a representative guanidinium salt phase transfer catalyst, hexaethylguanidium chloride (HEGCl). FIG. 2 illustrates the enhanced stability of the phosphazenium catalysts and compares a reaction utilizing HEGCl in o-DCB at 180° C. (See 10 FIG. 2) to the same reaction using a phosphazenium catalyst at either 180° C. (See 20 FIG. 2) or at 200° C. (See 30 FIG. 2). Although HEGCl provides a faster initial rate (See 12 FIG. 2) than the phosphazenium salt at 180° C. (See 22 FIG. 2), the reactions incorporating a phosphazenium salt phase transfer catalyst ultimately give higher yields (Compare 18, 28, and 36 FIG. 2). At 200° C. (30, FIG. 2), the rate increase obtained by increasing the reaction temperature more than compensates for the relative effectiveness of the catalysts, and reaction rates faster than could be achieved with HEGCl were obtained (Compare 12 and 32 FIG. 2).

Reference： [1]Patent: US2006/69291,2006,A1 .Location in patent: Page/Page column 9
[2]Patent: US2006/69291,2006,A1 .Location in patent: Page/Page column 9
[3]Patent: US2006/69291,2006,A1 .Location in patent: Page/Page column 9
[4]Patent: US2006/69291,2006,A1 .Location in patent: Page/Page column 9

9
[ 319-03-9 ]
[ 2444-90-8 ]
[ 38103-06-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In 1,2-dichloro-benzene; at 180℃; for 0.25h;Product distribution / selectivity;	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).
82%	N-neopentyl chloride of 4-dibutylaminopyridine; In 1,2-dichloro-benzene; at 175℃; for 1.0h;Product distribution / selectivity;	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.

Reference： [1]Patent: US2006/205958,2006,A1 .Location in patent: Page/Page column 6
[2]Patent: US2006/205958,2006,A1 .Location in patent: Page/Page column 5; 6

10
[ 117-21-5 ]
[ 2444-90-8 ]
[ 52256-80-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In 1,2-dichloro-benzene; at 180℃; for 2.0h;	A dry 100 mL flask was charged with 2.0 g (7.3 mmol) of the <strong>[2444-90-8]disodium bisphenol</strong> A, 2.67 g (14.6 mmol) of 3-chlorophthalic anhydride, 4 mL (14 mmol) of hexaethylguanidinium chloride as a 15 weight % 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 bisphenol A dianhydride had reached 40 % after 2 hour.

Reference： [1]Patent: US2006/205958,2006,A1 .Location in patent: Page/Page column 6

11
[ 118-45-6 ]
[ 2444-90-8 ]
[ 38103-06-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In 1,2-dichloro-benzene; at 180℃; for 5.0h;Product distribution / selectivity;	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 <strong>[118-45-6]4-chlorophthalic anhydride</strong>, 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.

Reference： [1]Patent: US2006/205958,2006,A1 .Location in patent: Page/Page column 6

Yield	Reaction Conditions	Operation in experiment
		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 bisphenol A disodium salt is prepared.
		EXAMPLE 2 The procedure of Example 1 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.

13
[ 1538-59-6 ]
[ 2444-90-8 ]
((C₆H₅)3SbBr)2(OC₆H₄C(CH₃)2C₆H₄O) [ No CAS ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1986,vol. 16,p. 623 - 644

14
[ 148935-94-8 ]
[ 2444-90-8 ]
polyetherimide [ No CAS ]
amic acids [ No CAS ]
[ 902759-72-2 ]

Yield	Reaction Conditions	Operation in experiment
0.25%; 0.363%	With 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. The results are given in Table II, in comparison with a control in which a solid isolated CIPAMI reagent was employed. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.
0.28%; 0.242%	With 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. The results are given in Table II, in comparison with a control in which a solid isolated CIPAMI reagent was employed. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.
0.19%; 0.200%	With 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. The results are given in Table II, in comparison with a control in which a solid isolated CIPAMI reagent was employed. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.

Reference： [1]Patent: EP1222168,2004,B1 .Location in patent: Page 8
[2]Patent: EP1222168,2004,B1 .Location in patent: Page 8
[3]Patent: EP1222168,2004,B1 .Location in patent: Page 8

15
[ 148935-94-8 ]
[ 2444-90-8 ]
polyetherimide [ No CAS ]
amic acids [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.21%	With 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. The results are given in Table II, in comparison with a control in which a solid isolated CIPAMI reagent was employed. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.
0.24%	With 1-[N-(4-chlorophthalimido)]-3-(N-phthalimido)benzene; 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.
< 0.1%	With 1,1,2,2,3,3-Hexaethylguanidiniumchlorid; In methoxybenzene; for 4.0h;Heating / reflux;	EXAMPLES 6-10 Each example employed a C1PAMI product (sample A or B) in the form of a paste prepared according to Example 2. 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 <strong>[2444-90-8]bisphenol A disodium salt</strong> and 100 ml of dry anisole. The mixture was dried by distillation under a positive argon atmosphere with removal of about 65 ml of anisole. It was then quantitatively transferred under argon pressure through an oven-dried adapter into the C1PAMI slurry. The combined mixture was heated in an oil bath at 170C, and 3.5 mole percent (based on bisphenol A salt) of hexaethylguanidinium chloride dissolved in anisole was added, also under argon. The mixture was heated under reflux for 4 hours to yield the desired polyetherimide. In each example the weight average molecular weight was determined by gel permeation chromatography; to avoid variations in analysis, it was additionally expressed as "Mw ratio" which is a percentage of the molecular weight of a single sample of commercial polyetherimide whose molecular weight was determined at the same time. The commercial polyetherimide was prepared by a method similar to that described in U.S. Patent 3,838,097. The results are given in Table II, in comparison with a control in which a solid isolated CIPAMI reagent was employed. It can be seen that the polyetherimide preparation method affords polymers having molecular weights comparable to or approaching that of a product prepared from solid C1PAMI. It is also apparent that amic acid proportions above 0.25%, as illustrated by Example 7, cause a decrease in molecular weight.

Reference： [1]Patent: EP1222168,2004,B1 .Location in patent: Page 8
[2]Patent: EP1222168,2004,B1 .Location in patent: Page 8
[3]Patent: EP1222168,2004,B1 .Location in patent: Page 8

16
[ 41663-84-7 ]
[ 2444-90-8 ]
[ 54395-52-7 ]

Yield	Reaction Conditions	Operation in experiment
99.4%Chromat.	With sodium chloride;HEG-Cl; In toluene; at 120℃;Inert atmosphere; Reflux;Product distribution / selectivity;	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)0.5100/(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.

Reference： [1]Patent: US2009/292128,2009,A1 .Location in patent: Page/Page column 11

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H401	Toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 2444-90-8 ] Synthesis Path-Upstream 1~3

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Aryls

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