m-Xylene

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m-Xylene
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
1,3-Xylene[1]
Systematic IUPAC name
1,3-Dimethylbenzene
Other names
m-Xylene[1]
Identifiers
3D model (JSmol)
605441
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.252 Edit this at Wikidata
EC Number
  • 203-576-3
101390
KEGG
RTECS number
  • ZE2275000
UNII
UN number 1307
  • InChI=1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3 checkY
    Key: IVSZLXZYQVIEFR-UHFFFAOYSA-N checkY
  • Cc1cccc(c1)C
  • CC1=CC(C)=CC=C1
Properties
C8H10
Molar mass 106.16 g/mol
Appearance Colorless liquid
Density 0.86 g/mL
Melting point −48 °C (−54 °F; 225 K)
Boiling point 139 °C (282 °F; 412 K)
insoluble
Solubility in ethanol miscible
Solubility in diethyl ether miscible
Vapor pressure 9 mmHg (20°C)[2]
-76.56·10−6 cm3/mol
1.49722
Viscosity 0.8059 cP at 0 °C
0.6200 cP at 20 °C
Dipole moment
 0.33-0.37 D[3]
Hazards
Main hazards Harmful or fatal if swallowed. Vapor harmful. Flammable liquid and vapor.
Safety data sheet (SDS) External MSDS
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word
 Danger
H226, H304, H312, H315, H318, H332
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P331, P332+P313, P362, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
1
3
0
Flash point 27 °C (81 °F; 300 K) [4]
527 °C (981 °F; 800 K)[4]
Explosive limits 1.1%-7.0%[2]
100 ppm[4] (TWA), 150 ppm[4] (STEL)
Lethal dose or concentration (LD, LC):
LCLo (lowest published)
 2010 ppm (mouse, 24 hr)
8000 ppm (rat, 4 hr)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (435 mg/m3)[2]
REL (Recommended)
 TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3)[2]
IDLH (Immediate danger)
 900 ppm[2]
Related compounds
benzene
toluene
o-xylene
p-xylene
Supplementary data page
M-Xylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[6]

Production and use[]

Petroleum contains about 1 weight percent xylenes.[7]

The major use of meta-xylene is in the production of isophthalic acid, which is used as a copolymerizing monomer to alter the properties of polyethylene terephthalate. The conversion m-xylene to isophthalic acid entails catalytic oxidation. meta-Xylene is also used as a raw material in the manufacture of 2,4- and 2,6-xylidine as well as a range of smaller-volume chemicals.[8][6] Ammoxidation gives isophthalonitrile.

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.[6]

See also[]

References[]

  1. ^ a b 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. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0669". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ DeanHandb, Lange´s Handbook of chemistry, 15th edition,1999.
  4. ^ a b c d "m-Xylene". International Chemical Safety Cards. IPCS/NIOSH. July 1, 2014. Archived from the original on December 5, 2017. Retrieved September 9, 2017.
  5. ^ "Xylene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. ^ a b c Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433.
  7. ^ 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
  8. ^ Ashford's Dictionary of Industrial Chemicals, third edition, page 9692.
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