M-Xylene

Last updated
m-Xylene
Skeletal formula Meta-Xylene-2D-structure.svg
Skeletal formula
Space-filling model M-xylene-spaceFilling.png
Space-filling model
Names
Preferred IUPAC name
1,3-Xylene [1]
Systematic IUPAC name
1,3-Dimethylbenzene
Other names
m-Xylene, [1] meta-Xylol
Identifiers
3D model (JSmol)
605441
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.252 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-576-3
101390
KEGG
PubChem CID
RTECS number
  • ZE2275000
UNII
UN number 1307
  • InChI=1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3 Yes check.svgY
    Key: IVSZLXZYQVIEFR-UHFFFAOYSA-N Yes check.svgY
  • Cc1cccc(c1)C
  • CC1=CC(C)=CC=C1
Properties
C8H10
Molar mass 106.16 g/mol
AppearanceColorless liquid
Odor Aromatic in high concentrations
Density 0.86 g/mL
Melting point −48 °C (−54 °F; 225 K)
Boiling point 139 °C (282 °F; 412 K)
does not react with water
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
0.33-0.37 D [3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful if swallowed. Vapor harmful. Flammable liquid and vapor.
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H226, H302, 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)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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):
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]
Safety data sheet (SDS) External MSDS
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

Production and use

Petroleum contains about 1 weight percent xylenes. [7] The meta isomer can be isolated from a mix of xylenes by the partial sulfonation (to which other isomers are less prone) followed by removal of unsulfonated oils and steam distillation of the sulfonated product.

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

Related Research Articles

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

Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

<span class="mw-page-title-main">Isocyanate</span> Chemical group (–N=C=O)

In organic chemistry, isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers.

<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">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

<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.

<span class="mw-page-title-main">Vanadium(V) oxide</span> Precursor to vanadium alloys and industrial catalyst

Vanadium(V) oxide (vanadia) is the inorganic compound with the formula V2O5. Commonly known as vanadium pentoxide, it is a brown/yellow solid, although when freshly precipitated from aqueous solution, its colour is deep orange. Because of its high oxidation state, it is both an amphoteric oxide and an oxidizing agent. From the industrial perspective, it is the most important compound of vanadium, being the principal precursor to alloys of vanadium and is a widely used industrial catalyst.

<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.

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.

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

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

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

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.

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

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

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

Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ortho-terphenyl, meta-terphenyl, and para-terphenyl. Commercial grade terphenyl is generally a mixture of the three isomers. This mixture is used in the production of polychlorinated terphenyls, which were formerly used as heat storage and transfer agents.

ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

References

  1. 1 2 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. 1 2 3 4 5 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. 1 2 3 4 "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. 1 2 3 Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433. ISBN   978-3527306732.
  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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