p-Xylene

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).[11]

p-Xylene
Skeletal formula
Space-filling model
Space-filling model
Names
Preferred IUPAC name
1,4-Xylene[1]
Systematic IUPAC name
1,4-dimethylbenzene
Other names
p-Xylene, p-dimethylbenzene; p-xylol; 1,4-xylene; p-methyltoluene;[2] paraxylene; chromar; scintillar; 4-methyltoluene;[3] NSC 72419; or 1,4-dimethylbenzene.[4]
Identifiers
3D model (JSmol)
1901563
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.088
EC Number
  • 203-396-5
2697
KEGG
RTECS number
  • ZE2625000
UNII
  • InChI=1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3 ☒N
    Key: URLKBWYHVLBVBO-UHFFFAOYSA-N ☒N
  • InChI=1/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3
    Key: URLKBWYHVLBVBO-UHFFFAOYAE
  • CC1=CC=C(C)C=C1
Properties
C8H10
Molar mass 106.168 g·mol−1
Appearance Colorless liquid
Odor Aromatic[5]
Density 0.861 g/mL
Melting point 13.2 °C (55.8 °F; 286.3 K)
Boiling point 138.35 °C (281.03 °F; 411.50 K)
Insoluble
Solubility in ethanol Very soluble
Solubility in diethyl ether Very soluble
Vapor pressure 9 mmHg (20°C)[5]
-76.78·10−6 cm3/mol
1.49582
Viscosity 0.7385 cP at 0 °C
0.6475 cP at 20 °C
0.00 D[6]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful or if swallowed. Vapor maybe toxic.[7] Flammable liquid and vapor.
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H302, H304, H312, H315, H319, H332, H335, H412
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P331, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
3
0
Flash point 27 °C (81 °F; 300 K)[8]
528 °C (982 °F; 801 K)[8]
Explosive limits 1.1%-7.0%[5]
100 ppm[8] (TWA), 150 ppm[8] (STEL)
Lethal dose or concentration (LD, LC):
4300 mg/kg[9]
4550 ppm (rat, 4 hr)[10]
3401 ppm (mouse)[10]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (435 mg/m3)[5]
REL (Recommended)
 TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3)[5]
IDLH (Immediate danger)
 900 ppm[5]
Safety data sheet (SDS) External MSDS
Related compounds
benzene
toluene
o-xylene
m-xylene
Supplementary data page
P-Xylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Production

The production of p-xylene is industrially significant, with annual demand estimated at 37 million tons in 2014, and still on the increase.[12][13] p-Xylene is produced by catalytic reforming of petroleum naphtha as part of the BTX aromatics (benzene, toluene and the xylene isomers) extracted from the catalytic reformate. The p-xylene is then separated out in a series of distillation, adsorption or crystallization and reaction processes from the m-xylene, o-xylene, and ethylbenzene. Its melting point is the highest among this series of isomers, but simple crystallization does not allow easy purification due to the formation of eutectic mixtures.

Such separation procedures are major cost factors in the production of p-xylene, and the search for alternative methods continues. For example, a reverse-osmosis technique has been proposed to improve various aspects of the processes.[14]

Industrial applications

p-Xylene is an important chemical feedstock. Among other industrial applications, it is a raw material in the large scale synthesis of various polymers. In particular it is a component in the production of terephthalic acid for polyesters such as polyethylene terephthalate (generally known as PET). It also may be polymerised directly to produce parylene.

Terephthalic acid

Toxicity and exposure

Xylenes are not acutely toxic, for example the LD50 (rat, oral) is 4300 mg/kg. Effects vary with animal and xylene isomer.

Concerns with xylenes focus on narcotic effects. Overexposure of p-xylene in humans can cause headache, fatigue, dizziness, listlessness, confusion, irritability, gastrointestinal disturbances including nausea and loss of appetite, flushing of the face, and a feeling of increased body heat. p-Xylene vapor exposure over the recommended exposure limit of 100 parts per million (ppm) can cause irritation to eye, nose, and throat and possible chest tightening and an abnormal gait.[15]

p-Xylene occurs naturally in petroleum and coal tar. It is emitted by most combustion sources, including automobile exhaust and tobacco smoke.[16]

Inhalation

Inhaling p-xylene can cause dizziness, headache, drowsiness, and nausea. If exposure through inhalation occurs, first aid includes fresh air, rest and possible medical attention. Through the use of ventilation or breathing protection, exposure to p-xylene through inhalation can be prevented.[17]

Skin

Exposure of p-xylene through the skin can cause dry skin and redness. If skin exposure occurs, first aid includes rinsing and then washing the affected area with soap and water as well as removing any contaminated clothing and thoroughly cleaning and drying before reuse. Exposure can be prevented through the use of protective gloves.[17]

Eyes

Exposure of p-xylene to eyes can cause redness and pain. If eyes are exposed, first aid includes rinsing of the eyes with water for several minutes, removal of contact lenses if applicable, and medical attention. Eye exposure can be prevented through the use of safety glasses or safety goggles.[17]

Ingestion

Ingestion of p-xylene can result in a burning sensation, abdominal pain, dizziness, drowsiness, headache, and nausea. If p-xylene is ingested one's mouth should be rinsed and vomiting should not be induced. Further medical attention should be sought. Ingestion can be prevented by not eating, drinking, or smoking when working with p-xylene.[17]

Short-term exposure

p-Xylene can cause issues with the central nervous system and if swallowed could cause chemical pneumonitis when breathed into the lungs.[17]

Long-term exposure

Liquid p-xylene exposure to the skin over long periods of time can remove the fat from the skin. The substance may also have effects on the central nervous system. Exposure can enhance hearing loss caused by noise exposure. Animal tests suggest that this substance could cause damage to human development and reproductive systems.[17]

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 139. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. Not to be used
  3. Archaic name
  4. "p-xylene". NIST. Retrieved 21 February 2013.
  5. NIOSH Pocket Guide to Chemical Hazards. "#0670". National Institute for Occupational Safety and Health (NIOSH).
  6. Perry's Handbook of Chemical Engineers
  7. P-Xylene: main hazards
  8. "p-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.
  9. P-Xylene: toxicity for rats
  10. "Xylenes". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  11. "p-Xylene MSDS". ScienceLab.com. {{cite web}}: Missing or empty |url= (help)
  12. Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). Ullmann's Encyclopedia of Industrial Chemistry. Wiley Online Library. doi:10.1002/14356007. ISBN 9783527303854.
  13. Nature 532,435–437 (28 April 2016) doi:10.1038/532435a
  14. Koh, D. Y.; McCool, B. A.; Deckman, H. W.; Lively, R. P. (2016). "Reverse osmosis molecular differentiation of organic liquids using carbon molecular sieve membrane". Science. 353 (6301): 804–7. Bibcode:2016Sci...353..804K. doi:10.1126/science.aaf1343. PMID 27540170. S2CID 9480478.
  15. "Material Safety Data Sheet – Para-Xylene". Amoco. Archived from the original on 4 March 2016. Retrieved 13 February 2013.
  16. EPA-454/R-93-048 Locating and estimating air emissions from sources of xylene Emission Inventory Branch Technical Support Division Office of Air Quality Planning and Standards U.S. Environmental Protection Agency March 1994
  17. "para-Xylene". National Institute for Occupational Safety and Health. Retrieved 12 February 2013.
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