p-Toluic acid

p-Toluic acid (4-methylbenzoic acid) is a substituted benzoic acid with the formula CH3C6H4CO2H. It is a white solid that is poorly soluble in water but soluble in acetone. A laboratory route to p-toluic acid involves oxidation of p-cymene with nitric acid.[2]

p-Toluic acid
Skeletal formula of p-toluic acid
Ball-and-stick model of the p-toluic acid molecule
Names
Preferred IUPAC name
4-Methylbenzoic acid
Other names
para-toluic acid
p-toluic acid
para-methylbenzoic acid
p-methylbenzoic acid
toluene-4-carboxylic acid
crithminic acid
Identifiers
3D model (JSmol)
3904552
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.549
EC Number
  • 202-803-3
KEGG
RTECS number
  • XU1575000
UNII
  • InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10) checkY
    Key: LPNBBFKOUUSUDB-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)
    Key: LPNBBFKOUUSUDB-UHFFFAOYAB
  • O=C(O)c1ccc(cc1)C
Properties
C8H8O2
Molar mass 136.150 g·mol−1
Appearance Crystalline solid
Density 1.06g/mL
Melting point 180 to 181 °C (356 to 358 °F; 453 to 454 K)[1]
Boiling point 274 to 275 °C (525 to 527 °F; 547 to 548 K)[1]
Sparingly soluble in hot water
Thermochemistry
-429 kJ/mol
3862 kJ/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H317, H319, H335
P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Role in production of terephthalic acid

p-Toluic acid is an intermediate in the conversion of p-xylene to terephthalic acid, a commodity chemical used in the manufacture of polyethylene terephthalate. It is generated both by the oxidation of p-xylene as well as the hydrogenolysis of 4-carboxybenzaldehyde. In related processes it is converted to methyl p-toluate, which is oxidized to monomethyl terephthalate.[3]

p-Toluic acid is an intermediate in the production of terephthalic acid.

See also

References
  1. Merck Index, 12th Edition, 9673
  2. W. F. Tuley; C. S. Marvel (1947). "p-Toluic Acid". Org. Synth. 27: 86. doi:10.15227/orgsyn.027.0086.
  3. Tomas, Rogerio A. F.; Bordado, Joao C. M.; Gomes, Joao F. P. (2013). "p-Xylene Oxidation to Terephthalic Acid: A Literature Review Oriented toward Process Optimization and Development". Chemical Reviews. 113 (10): 7421–7469. doi:10.1021/cr300298j. PMID 23767849.


Material Safety Data Sheet

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