P-Toluic acid

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p-Toluic acid
4-Methylbenzoic acid.svg
P-Toluic-acid-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-803-3
KEGG
PubChem CID
RTECS number
  • XU1575000
UNII
  • InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10) Yes check.svgY
    Key: LPNBBFKOUUSUDB-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceCrystalline 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:
GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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. Oxidation of p-xylene to terephthalic acid.svg
p-Toluic acid is an intermediate in the production of terephthalic acid.

See also

Related Research Articles

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In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">Polyethylene terephthalate</span> Polymer

Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.

<span class="mw-page-title-main">Benzyl group</span> Chemical group (–CH₂–C₆H₅)

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH2−C6H5. Benzyl features a benzene ring attached to a methylene group group.

In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst a in solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in distinct phases, typically solid-gas, respectively. The term is used almost exclusively to describe solutions and implies catalysis by organometallic compounds. Homogeneous catalysis is an established technology that continues to evolve. An illustrative major application is the production of acetic acid. Enzymes are examples of homogeneous catalysts.

<span class="mw-page-title-main">Terephthalic acid</span> Chemical compound

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. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

<span class="mw-page-title-main">Isophthalic acid</span> Chemical compound

Isophthalic acid is an organic compound with the formula C6H4(CO2H)2. This colorless solid is an isomer of phthalic acid and terephthalic acid. The main industrial uses of purified isophthalic acid (PIA) are for the production of polyethylene terephthalate (PET) resin and for the production of unsaturated polyester resin (UPR) and other types of coating resins.

<i>p</i>-Xylene Chemical compound

p-Xylene (para-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The p- stands for para-, indicating that the two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and m-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of p-xylene is 0.62 parts per million (ppm).

<span class="mw-page-title-main">Dimethyl terephthalate</span> Chemical compound

Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.

Autoxidation refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation.

<i>o</i>-Toluic acid Chemical compound

o-Toluic acid, also 2-methylbenzoic acid, is an aromatic carboxylic acid, with formula (CH3)C6H4(COOH). It is an isomer of p-toluic acid and m-toluic acid. When purified and recrystallized, o-toluic acid forms needle-shaped crystals. o-Toluic acid was first noticed by Sir William Ramsay, credited discoverer of the noble gases and winner of the 1904 Nobel Prize in Chemistry.

<i>m</i>-Xylene Chemical compound

m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.

<span class="mw-page-title-main">Polyester</span> Category of polymers, in which the monomers are joined together by ester links

Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

<span class="mw-page-title-main">Photo-oxidation of polymers</span>

In polymer chemistry photo-oxidation is the degradation of a polymer surface due to the combined action of light and oxygen. It is the most significant factor in the weathering of plastics. Photo-oxidation causes the polymer chains to break, resulting in the material becoming increasingly brittle. This leads to mechanical failure and, at an advanced stage, the formation of microplastics. In textiles the process is called phototendering.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

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<span class="mw-page-title-main">2,5-Furandicarboxylic acid</span> Chemical compound

2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future. Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.

<span class="mw-page-title-main">Polycyclohexylenedimethylene terephthalate</span> Chemical compound

Polycyclohexylenedimethylene terephthalate (PCT) is a thermoplastic polyester formed from the polycondensation of terephthalic acid and cyclohexanedimethanol. Its chemical structure is similar to that of polyethylene terephthalate (PET), with which it shares properties like dimensional stability and chemical resistance. PCT is also particularly resistant to high temperatures and hydrolysis. The melting point is 545 °F. Common brand names are Thermx (Ticona), Eastar (Eastman) and SkyPURA.

2-Hydroxyethyl terephthalic acid is an organic compound with the formula HOC2H4O2CC6H4CO2H. It is the monoester of terephthalic acid and ethylene glycol. The compound is a precursor to poly(ethylene terephthalate) (PET), a polymer that is produced on a large scale industrially. 2-Hydroxyethyl terephthalic acid is a colorless solid that is soluble in water and polar organic solvents. Near neutral pH, 2-hydroxyethyl terephthalic acid converts to 2-hydroxyethyl terephthalate, HOC2H4O2CC6H4CO2.

Methyl <i>p</i>-toluate Chemical compound

Methyl p-toluate is the organic compound with the formula CH3C6H4CO2CH3. It is a waxy white solid that is soluble in common organic solvents. It is the methyl ester of p-toluic acid. Methyl p-toluate per se is not particularly important but is an intermediate in some routes to dimethyl terephthalate, a commodity chemical.

References

  1. 1 2 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.


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