Terephthalic acid

Terephthalic acid
	Skeletal formula
	Ball-and-stick model of the terephthalic acid molecule
Names
	Preferred IUPAC name Benzene-1,4-dicarboxylic acid
	Other names Terephthalic acid; para-Phthalic acid; TPA; PTA; BDC
Identifiers
CAS Number	100-21-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1909333
ChEBI	CHEBI:15702 ;
ChEMBL	ChEMBL1374420;
ChemSpider	7208 ;
ECHA InfoCard	100.002.573
EC Number	202-830-0;
Gmelin Reference	50561
KEGG	C06337;
PubChem CID	7489;
RTECS number	WZ0875000;
UNII	6S7NKZ40BQ ;
CompTox Dashboard (EPA)	DTXSID6026080 ;
	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) Key: KKEYFWRCBNTPAC-UHFFFAOYSA-N ; InChI=1/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) Key: KKEYFWRCBNTPAC-UHFFFAOYAF;
	SMILES O=C(O)c1ccc(C(O)=O)cc1;
Properties
Chemical formula	C8H6O4
Molar mass	166.132 g·mol−1
Appearance	White crystals or powder
Density	1.519 g/cm3
Melting point	300 °C (572 °F; 573 K) Sublimes
Boiling point	Decomposes
Solubility in water	0.065 g/L at 25 °C
Solubility	polar organic solvents aqueous base
Acidity (pKa)	3.54, 4.34
Magnetic susceptibility (χ)	−83.5×10−6 cm3/mol
Structure
Dipole moment	2.6D
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−816.1 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point	260 °C (500 °F; 533 K)
Autoignition; temperature	496 °C (925 °F; 769 K)
Threshold limit value (TLV)	10 mg/m3 (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>1 g/kg (oral, mouse)
Safety data sheet (SDS)	MSDS sheet
Related compounds
Related carboxylic acids	Phthalic acid; Isophthalic acid; Benzoic acid; p-Toluic acid
Related compounds	p-Xylene; Polyethylene terephthalate; Dimethyl terephthalate
Supplementary data page
	Terephthalic acid (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Terephthalic acid is an organic compound with formula C₆H₄(CO₂H)₂. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually.^[8] The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

Terephthalic acid is also used in the production of PBT plastic (polybutylene terephthalate).^[10]

^ ^a ^b Haynes, p. 3.492
^ Haynes, p. 5.163
^ Haynes, p. 5.96
^ Haynes, p. 3.579
^ Karthikeyan, N.; Joseph Prince, J.; Ramalingam, S.; Periandy, S. (2015). "Electronic [UV–Visible] and vibrational [FT-IR, FT-Raman] investigation and NMR–mass spectroscopic analysis of terephthalic acid using quantum Gaussian calculations". Spectrochimica Acta Part A. 139: 229–242. Bibcode:2015AcSpA.139..229K. doi:10.1016/j.saa.2014.11.112. PMID 25561302.
^ Haynes, p. 5.37
^ Haynes, p. 16.42
^ ^a ^b Cite error: The named reference Ullmann was invoked but never defined (see the help page).
^ ^a ^b Haynes, p. 16.29
^ "Polybutylene Terephthalate (PBT) Material Guide & Properties Info". omnexus.specialchem.com. Archived from the original on 2023-11-24. Retrieved 2023-11-24.

[crc-1] Haynes, p. 3.492

[2] Haynes, p. 5.163

[3] Haynes, p. 5.96

[4] Haynes, p. 3.579

[5] Karthikeyan, N.; Joseph Prince, J.; Ramalingam, S.; Periandy, S. (2015). "Electronic [UV–Visible] and vibrational [FT-IR, FT-Raman] investigation and NMR–mass spectroscopic analysis of terephthalic acid using quantum Gaussian calculations". Spectrochimica Acta Part A. 139: 229–242. Bibcode:2015AcSpA.139..229K. doi:10.1016/j.saa.2014.11.112. PMID 25561302.

[6] Haynes, p. 5.37

[7] Haynes, p. 16.42

[Ullmann-8] Cite error: The named reference Ullmann was invoked but never defined (see the help page).

[crc2-9] Haynes, p. 16.29

[10] "Polybutylene Terephthalate (PBT) Material Guide & Properties Info". omnexus.specialchem.com. Archived from the original on 2023-11-24. Retrieved 2023-11-24.

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Terephthalic acid

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