Xylene

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See also: o-Xylene, m-Xylene,  and p-Xylene

The term xylene or xylol refers to a mixture of three structural isomers of the aromatic
hydrocarbon dimethylbenzene. Xylene is a clear, colorless, sweet-smelling liquid that is very
flammable. It is usually refined from crude oil in a process called alkylation. It is also produced
as a by-product from coal carbonisation derived from coke ovens, extracted from crude benzole
from gas, or by dehydrocyclodimerization and methylating of toluene and benzene.[1] It is also
manufactured from reformate.

Xylene is used as a solvent in the printing, rubber, and leather industries. Xylene is also used as
an inhalant drug for its intoxicating properties.

Contents
[hide]

 1 Chemical properties
 2 Applications
 3 Related compounds
 4 Health effects
 5 See also
 6 References
 7 External links

[edit] Chemical properties

Xylene encompasses ortho-, meta-, and para- isomers of dimethyl benzene. The o-, m- and p-
designations specify to which carbon atoms (of the benzene ring) the two methyl groups are
attached. Counting the carbon atoms from one of the ring carbons bonded to a methyl group, and
counting towards the second ring carbon bonded to a methyl group, the o- isomer has the IUPAC
name of 1,2-dimethylbenzene, the m- isomer has the IUPAC name of 1,3-dimethylbenzene, and
the p- isomer has the IUPAC name of 1,4-dimethylbenzene. Solvent grade xylene usually
contains a small percentage of ethylbenzene as a contaminant.
The chemical properties differ slightly from isomer to isomer. The melting point is between
−47.87 °C (−54.17 °F) (m-xylene) and 13.26 °C (55.87 °F) (p-xylene). The boiling point for each
isomer is around 140 °C (284.00 °F). The density is at around 0.87 g/mL (7.26 lb/U.S. gallon or
8.72 lb/imp gallon) and thus is less dense than water. Xylene in air can be smelled at 0.08 to 3.7
parts of xylene per million parts of air (ppm) and can begin to be tasted in water at 0.53 to 1.8
ppm.

Xylene Isomers
General
Common name Xylenes o-Xylene m-Xylene p-Xylene
1,2- 1,3- 1,4-
Systematic name Dimethylbenzenes
Dimethylbenzene Dimethylbenzene Dimethylbenzene
o-Xylol; m-Xylol; p-Xylol;
Other names Xylols
Orthoxylene Metaxylene Paraxylene
Molecular
C8H10, C6H4(CH3)2 or C6H4C2H6
formula
SMILES Cc1c(C)cccc1 Cc1cc(C)ccc1 Cc1ccc(C)cc1
Molar mass 106.16 g/mol
Appearance clear, colorless liquid
CAS number [1330-20-7] [95-47-6] [108-38-3] [106-42-3]
Properties
Density and
0.864 g/mL, liquid 0.88 g/mL, liquid 0.86 g/mL, liquid 0.86 g/mL, liquid
phase
Solubility in
practically insoluble
water
Soluble in non-polar solvents such as aromatic hydrocarbons
−47.4 °C (−53.3 −25 °C (−13 °F; −48 °C (−54.4 °F; 13 °C (55.4 °F;
Melting point
°F; 226 K) 248 K) 225 K) 286 K)
 138.5 °C (281.3 °F; 144 °C (291.2 °F; 139 °C (282.2 °F; 138 °C (280.4 °F;
Boiling point
412 K) 417 K) 412 K) 411 K)
0.812 cP at 20 °C 0.62 cP at 20 °C 0.34 cP at 30 °C
Viscosity
(68 °F) (68 °F) (86 °F)
Hazards
MSDS Xylenes o-Xylene m-Xylene p-Xylene
EU
Harmful (Xn)
Classification

NFPA 704 3
2
0
 
Flash point 30 °C (86 °F) 17 °C (63 °F) 25 °C (77 °F) 25 °C (77 °F)
R/S statement R10, R20/21, R38: (S2), S25
RTECS number ZE2450000 ZE2275000 ZE2625000
Supplementary data page
Structure &
n, εr, etc.
properties
Thermodynamic Phase behaviour
data Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related aromatic
toluene, mesitylene, benzene, ethylbenzene
hydrocarbons
Related
xylenols - types of phenols
compounds
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

The xylenes, as with many alkylbenzene compounds form complexes with various halocarbons.
The complexes of different isomers often have dramatically different properties from each other.
[2]
[edit] Applications
 p-Xylene is used as a feedstock in the production of terephthalic acid and dimethyl
terephthalate, both monomers used in the production of polyethylene terephthalate (PET)
plastic bottles and polyester clothing. 98% of p-Xylene production, and half of all xylene,
is used for polymer production.[3][4]
 Xylene is often used as a solvent and in the printing, rubber, and leather industries.
 It is used as a cleaning agent for steel and for silicon wafers and chips
 It is used as a thinner for paint, and in paints and varnishes. It may be substituted for
toluene to thin lacquers where slower drying is desired.
 It is found in small amounts in gasoline and airplane fuel.
 In animal studies it is often swabbed on the ears of rabbits to facilitate blood flow and
collection, although the area must subsequently be cleansed with alcohol to prevent
inflammation.
 In histology, xylene is also used for clearing the tissues following dehydration in
preparation for paraffin wax infiltration. It is also used after sections have been stained to
make them hydrophobic so that a coverslip may be applied with a resin in solvent.
 It is used as a carrier for acrylic based concrete sealers.

[edit] Related compounds

Xylenes are a starting material for the production of other chemicals. For instance chlorination of
both methyl groups gives three isomeric xylene dichlorides or 1,2-bis(chloromethyl)benzenes.
With oxidizing agents, such as potassium permanganate (KMnO4), the methyl group can be
oxidized to a carboxylic acid. By oxidizing both methyl groups, o-xylene forms phthalic acid and
p-xylene forms terephthalic acid, of which 30 million tons are made annually as a precursor for
polyethylene terephthalate (PET).

In articles of commerce, the term xylol refers to the solvent mixture of three xylene isomers,
sometimes containing ethylbenzene. In the chemical trade, this mixture is referred to as xylenes
(plural). This substance must not be confused with the toxic and corrosive xylenol compounds,
which are dimethyl phenol isomers.

[edit] Health effects

Xylene exhibits neurological effects. High levels from exposure for acute (14 days or less) or
chronic periods (more than 1 year) can cause headaches, lack of muscle coordination, dizziness,
confusion, and alterations in body balance[citation needed] . Exposure of people to high levels of xylene
for short periods can also cause irritation of the skin, eyes, nose, and throat, difficulty in
breathing and other problems with the lungs, delayed reaction time, memory difficulties,
stomach discomfort, and possibly adverse effects on the liver and kidneys. It can cause
unconsciousness and even death at very high levels (see inhalants). Xylene or products
containing Xylene should not be used indoors or around food. Xylene is not a controlled
substance.
Studies of unborn animals indicate that high concentrations of xylene may cause increased
numbers of deaths, and delayed growth and development.[citation needed] In many instances, these
same concentrations also cause damage to the mothers. It is not yet known whether xylene harms
the unborn fetus if the mother is exposed to low levels of xylene during pregnancy.

Besides occupational exposure, the principal pathway of human contact is via soil contamination
from leaking underground storage tanks containing petroleum products. Humans who come into
contact with the soil or groundwater may become affected. Use of contaminated groundwater as
a water supply could lead to adverse health effects