Phthalic anhydride

Base Information

• Chemical Name: Phthalic anhydride
• CAS No.: 85-44-9
• Deprecated CAS: 39363-63-8
• Molecular Formula: C6H4(CO)2O
• Molecular Weight: 148.118
• Hs Code.: 29173500
• European Community (EC) Number: 201-607-5
• ICSC Number: 0315
• NSC Number: 10431
• UN Number: 2214
• UNII: UVL263I5BJ
• DSSTox Substance ID: DTXSID2021159
• Nikkaji Number: J4.919K
• Wikipedia: Phthalic_anhydride
• Wikidata: Q410882
• Metabolomics Workbench ID: 55429
• ChEMBL ID: CHEMBL1371297
• Mol file: 85-44-9.mol

Synonyms:1,2-benzenedicarboxylic anhydride;1,3-isobenzofurandione;phthalic acid anhydride;phthalic anhydride;phthalic anhydride, 14C-labeled cpd

Chemical Property of Phthalic anhydride

Chemical Property:

• Appearance/Colour: white flakes
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: 131-134 °C(lit.)
• Refractive Index: 1.646
• Boiling Point: 295 °C at 760 mmHg
• PKA: 2.97[at 20 ℃]
• Flash Point: 139.7 °C
• PSA: 43.37000
• Density: 1.53 g/cm³
• LogP: 0.99720
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: 6g/l (slow decomposition)
• Water Solubility.: 6 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 148.016043985
• Heavy Atom Count: 11
• Complexity: 187
• Transport DOT Label: Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

Phthalic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41-42/43
• Safety Statements: 23-24/25-26-37/39-46-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)OC2=O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• Description: Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. Phthalic anhydride is an important chemical intermediate in the plastics industry from which are derived numerous phthalate esters that function as plasticizers in synthetic resins. Phthalic anhydride itself is used as a monomer for synthetic resins such as glyptal, the alkyd resins, and the polyester resins. Phthalic anhydride is also used as a precursor of anthraquinone, phthalein, rhodamine, phthalocyanine, fluorescein, and xanthene dyes. Phthalic anhydride is used in the synthesis of primary amines, the agricultural fungicide phaltan, and thalidomide. Other reactions with phthalic anhydride yield phenolphthalein, benzoic acid, phthalylsulfathiazole (an intestinal antimicrobial agent), and orthophthalic acid.
• Physical properties: Colorless to pale cream crystals with a characteristic, choking odor. Moisture sensitive. Odor threshold concentration is 53 ppb (quoted, Amoore and Hautala, 1983).
• Uses: Phthalic anhydride is used in the manufacture of unsaturated polyesters and as a curing agent for epoxy resins. When used as a pigment, it can be responsible for sensitization in ceramic workers.

Technology Process of Phthalic anhydride

There total 394 articles about Phthalic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 4.1%

Lapachol (84-79-7) → phthalic anhydride (85-44-9) + 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (137493-02-8,66512-82-1,41192-67-0) + naphtho[1,2-b]furan-4,5?dione (32358-83-1) + 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione (15297-92-4) + α-lapachone (4707-33-9) + 10,11-epoxy-lapachol (195156-48-0) + 3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione (119626-45-8,144125-22-4) + nor-lapachol (15297-99-1) + 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione (82423-03-8,41019-53-8) + 2-(methylvinyl)-2,3,4,9-tetrahydronaphtho[2,3-b]furan-4,9-dione (18635-24-0,80482-88-8,51920-95-7)

Guidance literature:

With (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; iodosylbenzene; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2012.06.042

Reference yield:

3,6-dibromo-cyclohex-1-ene-1,2-dicarboxylic acid → phthalic anhydride (85-44-9) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

at 200 ℃;

Reference yield:

monoethyl phthalate (2306-33-4) + 2-(ethoxycarbonyl)-5-hydroxybenzoic acid → phthalic anhydride (85-44-9) + 4-hydroxysalicylic acid (89-86-1) + 4-hydroxyphthalic acid (610-35-5) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5)

Guidance literature:

With sodium hydroxide; In water; pH=10; Reagent/catalyst; pH-value; Catalytic behavior; UV-irradiation;

DOI:10.1039/c8pp00307f

upstream raw materials:

4-methyleneoxetan-2-one

benzene-1,2-dicarboxylic acid

maleic anhydride

1,4-bisethylthiobuta-1,3-diene

Downstream raw materials:

2-(1H-pyridin-2-ylidene)-indan-1,3-dione

2-(4-pyridyl)-indane-1,3-dione

2-(5-chlorothiophene-2-carbonyl)benzoic acid

2-(5-bromo-2-thenoyl)benzoic acid

Refernces

• 1、 Norton. "-". . p. 1545. Retrieved 1961.
• 2、 Chatterjee, Koustuv,Hazra, Anasuya,Dollimore, David,Alexander, Kenneth S.. "An evaporation study for phthalic acids - A rapid method for pharmaceutical characterization". . p. 1156 - 1168. Retrieved 2002.
• 3、 Kisenyi, Jonathan M.,Cabeza, Javier A.,Smith, Arnold J.,Adams, Harry,Sunley, Glenn J.,et al.. "The Cyclometallation of Benzoic Acid and the X-Ray Crystal Structure of ". . p. 770 - 771. Retrieved 1985.
• 4、 Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra. "Efficient synthesis of symmetrical anhydrides by cross dehydrogenative coupling of aryl aldehydes over CuFe2O4 nanoparticles". . p. 461 - 468. Retrieved 2021/04/09.
• 5、 Ishchenko, A. V.,Rudina, N. A.,Yudanova, L. I.. "Thermal Decomposition of [Cu(H2O)2(C8H4O4)], [CuNi(H2O)4(C8H4O4)2], and [Ni(H2O)2(C8H4O4)2](H2O)2 with the Formation of Metal and Bimetal Nanoparticles". . p. 1663 - 1670. Retrieved 2021/08/24.