1823-59-2

Basic information

• Product Name: Bis-(3-phthalyl anhydride) ether
• Synonyms: 4,4'-Oxydiphthalic dianhydride;5,5’-oxybis-3-isobenzofurandione;oxydiphthalicanhydride;4-4'-OXYDIPHTHALIC ACID ANHYDRIDE;4,4'-OXYDIPHTHALIC ANHYDRIDE;BIS-(3-PHTHALYL ANHYDRIDE) ETHER;ODPA;4,4'-Oxydiphthalic Acid
• CAS NO: 1823-59-2
• Molecular Formula: C₁₆H₆O₇
• Molecular Weight: 310.21
• EINECS: 412-830-4
• Product Categories: Industrial/Fine Chemicals;Aromatic Tetracarboxylic Dianhydrides (for High-Performance Polymer Research);Diphenyl Ethers (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Anhydride Monomers;Monomers;Polymer Science;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;strong recommend
• Mol File: 1823-59-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 225-229 °C(lit.)
• Boiling Point: 410.39°C (rough estimate)
• Flash Point: 260.7 °C
• Appearance: off-white to white powder
• Density: 1.4942 (rough estimate)
• Vapor Pressure: 2.41E-13mmHg at 25°C
• Refractive Index: 1.6380 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: very slightly in Toluene,Acetone
• CAS DataBase Reference: Bis-(3-phthalyl anhydride) ether(CAS DataBase Reference)
• NIST Chemistry Reference: Bis-(3-phthalyl anhydride) ether(1823-59-2)
• EPA Substance Registry System: Bis-(3-phthalyl anhydride) ether(1823-59-2)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 2
• Hazardous Substances Data: 1823-59-2(Hazardous Substances Data)

Usage

Description

ODPA 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

Notclassified

InChI:InChI=1/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

Synthetic route

4-chlorophthalic anhydride (118-45-6) + C8H3O4(1-)*Na(1+) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
In N,N-dimethyl-formamide; toluene at 110℃; for 6h;	98.1%

4-iodophthalic anhydride (28418-89-5) + C8H3O4(1-)*Na(1+) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
In toluene; acetonitrile at 130℃; for 8h;	97.9%

4-fluorophthalic anhydride (319-03-9) + C8H3O4(1-)*K(1+) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; dimethyl sulfoxide at 120℃; for 8h;	97.8%

4,4'-oxydiphthalic acid (7717-76-2) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With 2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In propyl cyanide for 12h; Reflux;	90%
In water at 120℃; Purification / work up;
In 1,2-dichloro-benzene at 200℃; Product distribution / selectivity; Heating / reflux;
at 120 - 220℃; for 24h;
at 210 - 230℃;

4-chlorophthalic anhydride (118-45-6) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate; hexaethylguanidinium chloride In water; 1,2-dichloro-benzene for 3.5h; Heating / reflux;	85%
With potassium carbonate; sodium nitrite In N,N-dimethyl acetamide; toluene at 162 - 170℃; for 5h;	85%
Stage #1: 4-chlorophthalic anhydride With monopotassium carbonate; tetraphenylphosphonium bromide; potassium hydrogencarbonate In 2,4-dichlorotoluene for 7.5h; Heating / reflux; Nitrogen atmosphere; Stage #2: Conversion of starting material; Heating / reflux;	82%

triphenyl phosphite (101-02-0) + 4-chlorophthalic anhydride (118-45-6) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	71.5%

4-chlorophthalic anhydride (118-45-6) + 4-(3-nitrobenzoyl)oxyphthalic anhydride + tetraphenylphosphonium bromide (2751-90-8) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	61%

4-chlorophthalic anhydride (118-45-6) + 4-benzoyloxyphthalic anhydride + tetraphenylphosphonium bromide (2751-90-8) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	56%

4-nitrophthalic anhydride (5466-84-2) + 4-(4-methyl-1-piperidinyl)pyridine (80965-30-6) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
	51%

4-chlorophthalic anhydride (118-45-6) + 4-(4-methylbenzoyl)oxyphthalic anhydride + tetraphenylphosphonium bromide (2751-90-8) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	24%

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	10%

4-chlorophthalic anhydride (118-45-6) + oxyphthalic anhydride + tetraphenylphosphonium bromide (2751-90-8) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate	10%

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + 2,6-dichlorobenzoic acid (50-30-6) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + p-Toluic acid (99-94-5) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + ortho-chlorobenzoic acid (118-91-2) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + para-chlorobenzoic acid (74-11-3) + 1,2,4-Trichlorobenzene (120-82-1) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + 2,5-dichlorotoluene (19398-61-9) + tetraphenylphosphonium bromide (2751-90-8) + para-chlorobenzoic acid (74-11-3) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + 2,4-dichlorotoluene (95-73-8) + tetraphenylphosphonium bromide (2751-90-8) + para-chlorobenzoic acid (74-11-3) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + para-chlorobenzoic acid (74-11-3) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate In water; benzonitrile
With potassium carbonate
With potassium carbonate
With potassium carbonate In water; nitrobenzene

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + 1,2-dichloro-benzene (95-50-1) + para-chlorobenzoic acid (74-11-3) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-chlorophthalic anhydride (118-45-6) + tetraphenylphosphonium bromide (2751-90-8) + 2,5-dichlorobenzoic acid (50-79-3) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium carbonate

4-fluorophthalic anhydride (319-03-9) + 4-(4-chlorobenzoyl)oxyphthalic anhydride (138976-01-9) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With potassium fluoride In water; N,N-dimethyl-formamide

4-chlorophthalic anhydride (118-45-6) + Potassium benzoate (582-25-2) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium carbonate

4-chlorophthalic anhydride (118-45-6) + potassium carbonate (584-08-7) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene at 210℃; for 4h; Inert atmosphere;

4-nitro-N-methyl-phthalimide (41663-84-7) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium acetate / N,N-dimethyl-formamide / 80 °C 1.2: 0.5 h / Reflux 2.1: water; sodium hydroxide / Reflux 3.1: 24 h / 120 - 220 °C View Scheme

4-bromophthalic anhydride (86-90-8) + C8H3O4(1-)*Na(1+) → 4,4'-oxydiphthalic dianhydride (1823-59-2)

Conditions	Yield
In tert-butyl methyl ether; toluene at 140℃; for 10h;

[(m-aminophenylamino)-4-aminophenylmethylidene]propanedinitrile (439385-19-0) + 4,4'-oxydiphthalic dianhydride (1823-59-2) → polyimide; monomer(s): [(m-aminophenylamino)-4-aminophenylmethylidene]propanedinitrile; 4,4'-oxydiphthalic anhydride

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; chlorobenzene at 20 - 190℃;	100%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C22H24N2O5Si2

Conditions	Yield
at 130 - 140℃;	98%

4,4'-oxydiphthalic dianhydride (1823-59-2) + L-Tryptophan (73-22-3) → C27H16N2O8

Conditions	Yield
With pyridine; acetic acid at 120℃; for 16h; Reflux;	97%

(2-aminomethylpyridine) (3731-51-9) + 4,4'-oxydiphthalic dianhydride (1823-59-2) → N,N′-di(2-picolyl)-4,4′-oxybisphthalimide

Conditions	Yield
With acetic acid for 6h; Reflux;	97%

3,3'-bis(N-aminophthalimide) (916066-54-1) + 4,4'-oxydiphthalic dianhydride (1823-59-2) + 4,4'-oxydiphenylene diamine (101-80-4) → polymer, Mn/Mw = 1.1, Mn = 31630 g/mol, Mw = 35040 g/mol, inherent viscosity = 0.36 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 4,4\-oxydianiline; 3,3\44,4\-oxy(diphthalic anhydride)

Conditions	Yield
With 4-chloro-phenol; benzoic acid at 100 - 190℃;	96%

4,4'-oxydiphthalic dianhydride (1823-59-2) + (S)-methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate (65615-90-9) → C46H46N4O13

Conditions	Yield
Stage #1: 4,4'-oxydiphthalic dianhydride; (S)-methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate With N,N-dimethyl acetamide at 20℃; for 22h; Inert atmosphere; Stage #2: With acetic anhydride; triethylamine at 80℃; for 2.5h; Inert atmosphere;	95.2%

3,3'-bis(N-aminophthalimide) (916066-54-1) + 4,4'-oxydiphthalic dianhydride (1823-59-2) → polymer, Mn/Mw = 1.1, Mn = 20710 g/mol, Mw = 23260 g/mol, inherent viscosity = 0.20 dL/g; monomer(s): 3,3\-bis(N-aminophthalimide); 3,3\44,4\-oxy(diphthalic anhydride)

Conditions	Yield
With 4-chloro-phenol; benzoic acid at 100 - 190℃;	94%

4,4'-oxydiphthalic dianhydride (1823-59-2) → 4,4'-oxydiphthalic acid (7717-76-2)

Conditions	Yield
With phosphoric acid In 1,2-dichloro-benzene Product distribution / selectivity;	93%
With water; oxalic acid; N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene at 100℃; for 3h; Product distribution / selectivity;	82%
With water; citric acid; N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In 1,2-dichloro-benzene for 1h; Product distribution / selectivity;	82%

4,4'-oxydiphthalic dianhydride (1823-59-2) + methylamine (74-89-5) → oxo-bis-4,4'-(N-methylphthalimide) (27507-54-6)

Conditions	Yield
In water; toluene for 1h; Reflux;	90%

4,4'-oxydiphthalic dianhydride (1823-59-2) + (Benzocyclobutenyl)methylamine (1005-19-2) → C34H24N2O5

Conditions	Yield
Stage #1: 4,4'-oxydiphthalic dianhydride; (Benzocyclobutenyl)methylamine In N,N-dimethyl acetamide at 20℃; for 5h; Inert atmosphere; Stage #2: With acetic anhydride; triethylamine In N,N-dimethyl acetamide at 100℃; for 4h; Inert atmosphere;	85%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 1-amino-2-propene (107-11-9) → N,N'-diallyldiamide of 4,4'-oxydiphthalic acid (56070-47-4)

Conditions	Yield
With acetic acid at 20℃; for 11h; Reflux; Inert atmosphere;	84%

4,4'-oxydiphthalic dianhydride (1823-59-2) + ethanolamine (141-43-5) → 5,5'-bis[phthalimido-N-2-hydroxy ethyl]ether (50444-29-6)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 139 - 170℃;	81%
In N,N-dimethyl-formamide for 9h; Reflux;	45%
In N,N-dimethyl-formamide for 9h; Reflux;	45%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane Inert atmosphere; Reflux;
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane Reflux;

4,4'-oxydiphthalic dianhydride (1823-59-2) + 4,4'-oxydiphenylene diamine (101-80-4) → C40H26N4O7

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;	81%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 1,4-phenylenediamine (106-50-3) → C28H18N4O5

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;	80%

4,4'-oxydiphthalic dianhydride (1823-59-2) + m-phenylenediamine (108-45-2) → C28H18N4O5

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one; toluene at 170℃; for 5h; Cooling; Dean-Stark;	78%

4,4'-oxydiphthalic dianhydride (1823-59-2) + cycloheptanamine (5452-35-7) → C30H32N2O5

Conditions	Yield
With acetic acid at 120℃; for 8h;	77%

4,4'-oxydiphthalic dianhydride (1823-59-2) + propan-1-ol-3-amine (156-87-6) → C22H20N2O7

Conditions	Yield
With acetic acid at 120℃; for 8h;	75%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 4-amino-n-butyric acid (56-12-2) → C24H20N2O9 (1134083-69-4)

Conditions	Yield
In N,N-dimethyl-formamide	74%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 6-aminohexanoic acid (60-32-2) → C28H28N2O9 (1230103-67-9)

Conditions	Yield
In N,N-dimethyl-formamide	73%

4,4'-oxydiphthalic dianhydride (1823-59-2) + nickel(II) nitrate hexahydrate + water (7732-18-5) + N,N'-bis(pyrid-4-yl)piperazine (213008-55-0) → 2C14H16N4*2H2O*2Ni(2+)*C16H6O9(4-)

Conditions	Yield
With lithium hydroxide at 160℃; for 72h; Sonication;	71%

4,4'-oxydiphthalic dianhydride (1823-59-2) + Cyclopentamine (1003-03-8) → 4,4'-oxybis(N-cyclopentylphthalimide)

Conditions	Yield
With acetic acid at 120℃; for 8h;	70%

4,4'-oxydiphthalic dianhydride (1823-59-2) + 2-[5-methyl-5-(4-aminophenyl)-1,3-dioxooctahydroisoindol-2-yl]-3-methylbutanoic acid → (S)-2-(5-(4-(5-(2-(4-(2-((S)-1-carboxy-3-methylbutyl)-5-methyl-1,3-dioxooctahydro-1H-isoindol-5-yl)phenyl)-1,3-dioxoisoindolin-5-yloxy)-1,3-dioxoisoindolin-2-yl)phenyl)-5-methyl-1,3-dioxo-1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)-3-methylbutanoic acid

Conditions	Yield
With pyridine; acetic acid for 4h; Reflux;	69%

propylamine (107-10-8) + 4,4'-oxydiphthalic dianhydride (1823-59-2) → C24H24N2O5

Conditions	Yield
With acetic acid at 120℃; for 8h;	68%

Upstream product

• 319-03-9 4-fluorophthalic anhydride 
• 28418-89-5 4-iodophthalic anhydride 
• 86-90-8 4-bromophthalic anhydride 
• 118-45-6 4-chlorophthalic anhydride 
• 41663-84-7 4-nitro-N-methyl-phthalimide 
• 584-08-7 potassium carbonate 
• 5466-84-2 4-nitrophthalic anhydride 
• 80965-30-6 4-(4-methyl-1-piperidinyl)pyridine 
• 101-02-0 triphenyl phosphite 
• 582-25-2 Potassium benzoate 
• 138976-01-9 4-(4-chlorobenzoyl)oxyphthalic anhydride 
• 2751-90-8 tetraphenylphosphonium bromide 
• 50-79-3 2,5-dichlorobenzoic acid 
• 95-50-1 1,2-dichloro-benzene 

Downstream Products

• 89-20-3 4-chlorophthalic acid 
• 7717-76-2 4,4'-oxydiphthalic acid 

Relevant articles and documents

Preparation method of 4, 4'-diphenyl ether tetracarboxylic dianhydride

The invention provides a preparation method of 4, 4'-diphenyl ether tetracarboxylic dianhydride, which comprises the following steps: S1, dissolving 4-nitrophthalic acid in a solvent, and heating for dehydration; S2, adding a molybdenum salt catalyst, a halogen promoter and carbonate into the reaction liquid obtained in S1, and carrying out etherification coupling reaction to obtain a 4, 4'-diphenyl ether tetracarboxylic acid crude product; S3, refining and dehydrating the crude product obtained in S3 to obtain 4, 4'-diphenyl ether tetracarboxylic dianhydride; wherein the weight ratio of the 4-nitrophthalic acid to the solvent to the molybdenum salt to the halogen is 1: (2-3.5): (0.02-0.05): (0.1-0.3); and the molar ratio of the 4-nitrophthalic acid to the carbonate is 1: (0.55-0.75). The molybdenum powder serves as the catalyst, the halogen serves as the cocatalyst, the conversion rate of the 4-nitrophthalic acid is larger than 99%, the molar yield of the 4, 4'-diphenyl ether tetracarboxylic acid crude product is larger than 85%, the method is unique, the technological process is simple, operation is easy, the yield is high, the cost is low, and the production efficiency and economic benefits are high.

Preparation method of 4,4'-oxydiphthalic anhydride

The invention relates to the technical field of synthesis of compounds, and particularly discloses a preparation method of 4,4'-oxydiphthalic anhydride. The preparation method comprises the followingsteps: mixing a specific compound, a solvent and a water-carrying agent, carrying out a dehydration coupling reaction at 110-155 DEG C, and carrying out cooling and crystallization to obtain 4,4'-oxydiphthalic anhydride crystals. The method has the advantages of short reaction process route, fewer byproducts and high purity and yield of the reaction product, and can be widely popularized and used.

Preparation method for diphenyl ether tetracarboxylic acid dianhydride

The invention relates to a preparation method for 3,3',4,4'-diphenyl ether tetracarboxylic acid dianhydride. The method comprises the following steps: reacting 4-chlorophthalic anhydride with potassium carbonate for 4-5h at the temperature of 162-170 DEG