Isophthalic acid

Isophthalic acid
Names
	Other names Benzene-1,3-dicarboxylic acid; meta-Phthalic acid
Identifiers
CAS Number	121-91-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30802 ;
ChemSpider	8182 ;
ECHA InfoCard	100.004.098
PubChem CID	8496;
CompTox Dashboard (EPA)	DTXSID3021485 ;
	InChI InChI=1S/C8H6O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)(H,11,12) Key: QQVIHTHCMHWDBS-UHFFFAOYSA-N ; InChI=1/C8H6O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)(H,11,12) Key: QQVIHTHCMHWDBS-UHFFFAOYAY;
	SMILES O=C(O)c1cccc(C(=O)O)c1;
Properties
Chemical formula	C6H4(COOH)2
Molar mass	166.14 g/mol
Appearance	White crystalline solid
Density	1.526 g/cm3, Solid
Solubility in water	Insoluble in water
Acidity (pKa)	3.46, 4.46
Related compounds
Related carboxylic acids	Benzoic acid; Phthalic acid (ortho) ; Terephthalic acid (para) ; Trimesic acid (benzene-1,3,5-tricarboxyllic acid)
	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

Isophthalic acid is an organic compound with the formula C₆H₄(CO₂H)₂. This colourless solid is an isomer of phthalic acid and terephthalic acid.

Preparation

Isophthalic acid is produced on the miliard kilogram per year scale by oxidizing meta-xylene using oxygen.^[2] The process employs a cobalt-manganese catalyst. In the laboratory, chromic acid can be used as the oxidant. It also arises by fusing potassium meta-sulphobenzoate, or meta-brombenzoate with potassium formate (terephthalic acid is also formed in the last case).

The barium salt (as its hexahydrate) is very soluble (a distinction between phthalic and terephthalic acids). Uvitic acid, 5-methylisophthalic acid, is obtained by oxidizing mesitylene or by condensing pyroracemic acid with baryta water.

Applications

Aromatic dicarboxylic acids are used as precursors (in form of acyl chlorides) to commercially important polymers, e.g. the fire-resistant material Nomex. Mixed with terephthalic acid, isophthalic acid is used in the production of resins for drink plastic bottles. The high-performance polymer polybenzimidazole is produced from isophthalic acid.^[2] Also, the acid is used as an important input to produce insulation materials.

References

^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
^ ^a ^b Richard J. Sheehan "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a26_193

External links

International Chemical Safety Card 0500

[1] Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.

[Ullmann-2] Richard J. Sheehan "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a26_193

[1]

[2]