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100-21-0

Basic Information
CAS No.: 100-21-0
Name: Terephthalic acid
Article Data: 717
Cas Database
Molecular Structure:
Molecular Structure of 100-21-0 (Terephthalic acid)
Formula: C8H6O4
Molecular Weight: 166.133
Synonyms: Terephthalicacid (7CI,8CI);1,4-Dicarboxybenzene;4-Carboxybenzoic acid;Amoco TA 33;NSC36973;QTA;TA 33LP;WR 16262;p-Benzenedicarboxylic acid;p-Carboxybenzoic acid;p-Dicarboxybenzene;p-Phthalic acid;PTA;1,4-Benzenedicarboxylic acid;
EINECS: 262-050-1
Density: 1.51 g/cm3
Melting Point: 300 °C
Boiling Point: 392.4 °C at 760 mmHg
Flash Point: 260°C
Solubility: slightly soluble in water (0,017 g/L at 25°C)
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: N/A
PSA: 74.60000
LogP: 1.08300
Synthetic route
106-42-3

para-xylene

100-21-0

terephthalic acid

Conditions
ConditionsYield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid at 200℃; under 30753.1 Torr; for 10h; Time; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;99.9%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;98%
With oxygen; acetic acid; hydrogen bromide; cobalt(II) acetate; manganese(II) acetate In water at 200℃; under 22502.3 Torr; for 0.05h; Product distribution / selectivity; Inert atmosphere;98.3%
99-94-5

p-Toluic acid

100-21-0

terephthalic acid

Conditions
ConditionsYield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;99.1%
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;99.1%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;97%
106-42-3

para-xylene

A

100-21-0

terephthalic acid

B

619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With air; hydrogen bromide; acetic acid; cobalt(II) acetate; manganese(II) acetate at 180℃; under 25745 Torr; for 0.166667h;A 98.3%
B 1.4%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; cerium(III) acetate at 165℃; under 25745 Torr; for 0.166667h;A 98.2%
B 1.1%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; manganese(II) acetate at 170℃; under 25745 Torr; for 0.166667h;A 97.5%
B 1.9%
106-42-3

para-xylene

A

100-21-0

terephthalic acid

B

104-87-0

4-methyl-benzaldehyde

C

619-66-9

4-Carboxybenzaldehyde

D

99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogen bromide; oxygen; acetic acid; cobalt(II) acetate; manganese(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 98.1%
B 0.2%
C 0.4%
D 0.4%
With oxygen; acetic acid; palladium diacetate; antimony(III) acetate In water at 182 - 195℃; under 16501.7 - 20929.4 Torr; for 1 - 1.5h; Product distribution / selectivity;A 50.3%
B 7.2%
C 6.4%
D 6.2%
With hydrogen bromide; oxygen; acetic acid; zirconium oxyacetate; cobalt(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 4.9%
B 3%
C 1.9%
D 36.9%
623-27-8

terephthalaldehyde,

100-21-0

terephthalic acid

Conditions
ConditionsYield
With NADH oxidase and vanillin dehydrogenase 2 co-expressed in Escherichia coli cells In aq. phosphate buffer at 30℃; for 12h; pH=7; Microbiological reaction;98%
With tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen In acetonitrile at 20℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;95%
With sodium perborate In acetic acid at 45 - 50℃;93%
619-66-9

4-Carboxybenzaldehyde

100-21-0

terephthalic acid

Conditions
ConditionsYield
With water; ozone In acetonitrile for 5h; Irradiation;98%
With NADH oxidase and vanillin dehydrogenase 2 co-expressed in Escherichia coli cells In aq. phosphate buffer at 30℃; for 3h; pH=7; Microbiological reaction;98%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;97%
201230-82-2

carbon monoxide

74-11-3

para-chlorobenzoic acid

100-21-0

terephthalic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide at 65℃; for 8h;98%
With sodium hydroxide; dicobalt octacarbonyl In water at 65℃; under 1471.02 Torr; for 6h; Product distribution; Irradiation;93.4 % Chromat.
104-87-0

4-methyl-benzaldehyde

100-21-0

terephthalic acid

Conditions
ConditionsYield
With oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 60℃; under 12049.9 Torr; for 1h; Product distribution / selectivity;98%
201230-82-2

carbon monoxide

106-37-6

1.4-dibromobenzene

100-21-0

terephthalic acid

Conditions
ConditionsYield
With sodium hydroxide; cobalt(II) acetate In ethanol at 30℃; under 1520 Torr; for 4h; Irradiation;97.1%
With sodium hydroxide; dicobalt octacarbonyl In ethanol; water at 65℃; under 1471.02 Torr; for 4h; Product distribution; Irradiation;82.5 % Chromat.
589-29-7

p-xylylene glycol

100-21-0

terephthalic acid

Conditions
ConditionsYield
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication;97%
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;96%
With sodium hypochlorite; water at 25℃; for 0.5h;94%
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    CAS No.: 100-21-0 Formula: C8H6O4 Molecular Weight: 166.13 Melting Point: 300ºC Boiling Point: 392.4ºC at 760 mmHg

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    Product Name: Terephthalic acid CAS: 100-21-0 MF: C8H6O4 MW: 166.13 EINECS: 202-830-0 Melting point >300 °C (lit.) Boiling point 214.32°C (rough estimate) density 1.58 g/cm3 at 25 °C vapor pressure <

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Consensus Reports

Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

ACGIH TLV: TWA 10 mg/m3

Specification

The Terephthalic acid is an organic compound with the formula C8H6O4. The IUPAC name of this chemical is terephthalic acid. With the CAS registry number 100-21-0, it is also named as 1,4-Benzenedicarboxylic acid. The product's classification codes are Antioxidants; Drug / Therapeutic Agent; Free radical scavengers; Mutation data; Skin / Eye Irritant; TSCA Flag T [Subject to the Section 4 test rule under TSCA]. Besides, it is a white powder, which should be stored in a cool and ventilated place. It is used in the manufacture of synthetic resin, synthetic fibers, plasticizers and chromatography reagents.

Physical properties about Terephthalic acid are: (1)ACD/LogP: 2.00; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 2; (8)#Freely Rotating Bonds: 2; (9)Polar Surface Area: 74.6 Å2; (10)Index of Refraction: 1.618; (11)Molar Refractivity: 40.113 cm3; (12)Molar Volume: 114.493 cm3; (13)Polarizability: 15.902×10-24cm3; (14)Surface Tension: 70.304 dyne/cm; (15)Density: 1.451 g/cm3; (16)Flash Point: 205.267 °C; (17)Enthalpy of Vaporization: 67.722 kJ/mol; (18)Boiling Point: 392.373 °C at 760 mmHg.

Preparation: this chemical can be prepared by 1,4-dimethyl-benzene. This reaction will need reagent NHPI, Co(acac)2, O2 and solvent acetic acid. The reaction time is 12 hours with reaction temperature of 100 °C. The yield is about 23 %.



Uses of Terephthalic acid: it can be used to produce N,N'-p-phenylene-bis-carbamic acid diethyl ester by heating. It will need reagent polymer-supported diphenylphosphoryl azide, Et3N and solvent benzene with reaction time of 24 hours. The yield is about 36%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1C(=O)O)C(=O)O
(2)InChI: InChI=1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
(3)InChIKey: KKEYFWRCBNTPAC-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
(5)Std. InChIKey: KKEYFWRCBNTPAC-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 767mg/kg (767mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 469, 1971.
mouse LD50 intraperitoneal 1430mg/kg (1430mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 16, Pg. 1655, 1968.
mouse LD50 oral 3200mg/kg (3200mg/kg)   Kodak Company Reports. Vol. 21MAY1971,
rat LD50 oral > 6400mg/kg (6400mg/kg)   Kodak Company Reports. Vol. 21MAY1971,