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88-99-3

Basic Information
CAS No.: 88-99-3
Name: Phthalic acid
Article Data: 903
Molecular Structure:
Molecular Structure of 88-99-3 (Phthalic acid)
Formula: C8H6O4
Molecular Weight: 166.133
Synonyms: Phthalicacid (8CI);NSC 5348;Sunftal 20;o-Benzenedicarboxylic acid;o-Carboxybenzoic acid;o-Dicarboxybenzene;o-Phthalic acid;1,2-Benzenedicarboxylicacid;
EINECS: 201-873-2
Density: 1.451 g/cm3
Melting Point: 210-211 °C (dec.)(lit.)
Boiling Point: 378.274 °C at 760 mmHg
Flash Point: 196.749 °C
Solubility: 7 g/L (25 °C) in water
Appearance: White crystals or fine white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 74.60000
LogP: 1.08300
Synthetic route
95-47-6

o-xylene

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.0833333h; microwave irradiation;89%
With manganese(II) bromide; dihydrogen peroxide; oxygen In supercritical water at 380℃; under 172517 - 180018 Torr;78%
With dihydrogen peroxide; sodium carbonate; acetic acid at 100℃; under 7500.75 Torr; for 12h; Reagent/catalyst; Green chemistry;78%
95-47-6

o-xylene

A

87-41-2

2-benzofuran-1(3H)-one

B

88-99-3

benzene-1,2-dicarboxylic acid

C

65-85-0

benzoic acid

D

119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 72%
C n/a
D n/a
With oxygen; manganese(II) bromide; hydrogen bromide In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 65%
C n/a
D n/a
With dihydrogen peroxide; manganese(II) bromide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 63%
C n/a
D n/a
643-79-8

o-phthalic dicarboxaldehyde

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 50h; Heating;93%
With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal In methanol at 20℃; for 7h;90%
With tert.-butylhydroperoxide; copper(l) chloride In acetonitrile at 20℃; for 2.5h;84%
95-47-6

o-xylene

A

87-41-2

2-benzofuran-1(3H)-one

B

88-99-3

benzene-1,2-dicarboxylic acid

C

65-85-0

benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With oxygen; manganese(II) bromide; hydrogen bromide In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With oxygen; hydrogen bromide; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 63%
C n/a
95-47-6

o-xylene

A

87-41-2

2-benzofuran-1(3H)-one

B

529-20-4

2-methylphenyl aldehyde

C

88-99-3

benzene-1,2-dicarboxylic acid

D

65-85-0

benzoic acid

E

119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 71%
D n/a
E n/a
With oxygen; hydrogen bromide; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 60%
D n/a
E n/a
With oxygen; hydrogenchloride; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 17%
D n/a
E n/a
With oxygen; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 8%
D n/a
E n/a
91-20-3

naphthalene

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.125h; microwave irradiation;78%
With sodium hypochlorite; ruthenium(III) chloride trihydrate; sulfuric acid; tetrabutylammomium bromide In water; 1,2-dichloro-ethane at 23℃; for 0.5h; pH=9; Green chemistry;58%
With silica gel at -196.1℃; Irradiation;49%
95-47-6

o-xylene

A

118-90-1

ortho-methylbenzoic acid

B

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: o-xylene With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen at 195℃; under 14251.4 Torr; for 0.2h;
Stage #2: With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen; acetic acid at 150℃; under 4500.45 Torr; for 4h; Temperature; Pressure; Reagent/catalyst;
A 89.3%
B 10.6%
Stage #1: o-xylene With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen at 120℃; under 2250.23 Torr; for 1.5h;
Stage #2: With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen; acetic acid at 170℃; under 12001.2 Torr; for 0.6h; Temperature; Pressure; Reagent/catalyst;
A 14.4%
B 85.3%
With zinc(II) oxide In N,N-dimethyl-formamide for 0.133333h; microwave irradiation;A 80%
B 5 % Spectr.
201230-82-2

carbon monoxide

2042-37-7

o-cyanobromobenzene

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 12h; Irradiation;78%
5779-72-6

2,4,5-trimethylbenzaldehyde

A

89-05-4

1,2,4,5-benzenetetracarboxylic acid

B

34240-10-3

5-methyl-1,2,4-benzenetricarboxylic acid

C

528-44-9

1,2,4-benzene tricarboxylic acid

D

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 2,4,5-trimethylbenzaldehyde With oxygen at 210℃; under 24002.4 Torr;
Stage #2: With oxygen; hydrogen bromide In water at 210℃; under 21752.2 Torr;
Stage #3: With hydrogen; 0.5% Pd/C at 150℃; under 7500.75 Torr;
95-47-6

o-xylene

A

118-90-1

ortho-methylbenzoic acid

B

87-41-2

2-benzofuran-1(3H)-one

C

88-99-3

benzene-1,2-dicarboxylic acid

D

65-85-0

benzoic acid

E

119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 74%
D n/a
E n/a
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 71%
D n/a
E n/a
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 52%
D n/a
E n/a
With dihydrogen peroxide; cobalt(II) bromide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 51%
D n/a
E n/a
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is phthalic acid. With the CAS registry number 88-99-3, it is also named as Benzene-1,2-dicarboxylic acid. The product's categorie is Phthalic Acids, Esters and Derivatives. It is white crystals or fine white powder which is soluble in methanol and ethanol, slightly soluble in water and ether, insoluble in chloroform. In addition, this chemical is stable, combustible and incompatible with strong oxidizing agents. Furthermore, it should be sealed in the container.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.88; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.618; (11)Molar Refractivity: 40.113 cm3; (12)Molar Volume: 114.493 cm3; (13)Polarizability: 15.902×10-24 cm3; (14)Surface Tension: 70.304 dyne/cm; (15)Enthalpy of Vaporization: 66.051 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Rotatable Bond Count: 2; (18)Exact Mass: 166.026609; (19)MonoIsotopic Mass: 166.026609; (20)Topological Polar Surface Area: 74.6; (21)Heavy Atom Count: 12; (22)Complexity: 177.

Preparation of Phthalic acid: It can be obtained by the hydrolysis of phthalic anhydride. Adding phthalic anhydride to the 60 °C water, and stirring while adding ammonia to the ph value of 8. After bleaching filtered and acidified with hydrochloric acid, we can get the product by  washing. Reactive process:

Uses of Phthalic acid: It is used in the preparation of standard solution, dyes, polyester resin, polyester, plasticizers and drugs. And it is also used as analytical reagent. Furthermore, this chemical can react with 2-chloro-6-methyl-aniline to get N-(2-chloro-6-methyl-phenyl)-phthalimide. The temperature is 190 - 220 °C and the yield is 64%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule structure. 
1. SMILES:c1ccc(c(c1)C(=O)O)C(=O)O
2. InChI:InChI=1/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 550mg/kg (550mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Proceedings of the Society for Experimental Biology and Medicine. Vol. 49, Pg. 471, 1942.
mouse LD50 oral 2530mg/kg (2530mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 711, 1992.
rat LD50 unreported 1100mg/kg (1100mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 32(8), Pg. 12, 1967.