Xylene

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The term xylene refers to a group of three benzene
(/entry/Benzene) derivatives, each of which has two
methyl functional groups (/entry/Functional_group)
attached to the benzene ring. The three members of the
group are isomers (/entry/Isomer) and are called ortho-,
meta-, and para-xylene (or o-, m-, and p-xylene). Each
xylene is a colorless, sweet-smelling liquid that is highly
flammable. They occur naturally in petroleum (/entry/File:Iupac-cyclic.png)
(/entry/Petroleum) and coal tar and are formed during The three xylene isomers, each of which has two methyl
forest fires. groups attached to a benzene ring. The carbon atoms on the
benzene ring are numbered from one through six, and each
The xylene group methyl group is indicated by a straight line.
Contents ranks among the
top 30 chemicals produced in the United States (/entry/United_States),
1 Nomenclature
measured in terms of volume. The xylenes are solvents (/entry/Solvent) and are
2 Notable characteristics
3 Applications used as cleaning agents. They are found in pesticides (/entry/Pesticide), paint
4 Health effects thinners, paints (/entry/Paint), and varnishes (/entry/Varnish), and they are used
5 See also by the printing (/entry/Printing), rubber (/entry/Rubber), and leather industries.
6 Notes
7 References
Nomenclature
8 External links
9 Credits The o-, m- and p- isomers specify the relative positions of attachment of the two
methyl groups to carbon (/entry/Carbon) atoms on the main ring structure. A ring
carbon atom directly bonded to a methyl group is considered as position one,
pH Theory and the other ring carbon atoms are then counted, while moving toward the point
Guide of attachment of the next methyl group. In this manner, the o- isomer takes the
name 1,2-dimethylbenzene, according to the system recommended by the
Get an electronic Guide
on pH measurement. IUPAC (International Union of Pure and Applied Chemistry). Likewise, the m-
Download now! isomer has the IUPAC name 1,3-dimethylbenzene, and the p- isomer has the
METTLER TOLEDO
IUPAC name 1,4-dimethylbenzene.

Notable characteristics
The xylenes have very similar properties, differing slightly from isomer to isomer. The boiling point
(/entry/Boiling_point) for each isomer is around 140 C (284.00 F), and the melting point (/entry/Melting_point) lies
between 47.87 C (54.17 F) (m-xylene) and 13.26 C (55.87 F) (p-xylene). The density is at around 0.87 kg/L
(7.26 lb/U.S. gallon or 8.72 lb/imp gallon), indicating that each xylene 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 (/entry/Water)
at 0.53 to 1.8 ppm.

With oxidizing agents such as potassium permanganate (KMnO4), the methyl group can be oxidized to a carboxylic
acid (/entry/Carboxylic_acid). By oxidizing both methyl groups towards the acid, o-xylene forms phthalic acid, and p-
xylene forms terephthalic acid.

The Xylene Group

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 formula
C8H10
(/entry/Chemical_formula)

SMILES Cc1c(C)cccc1 Cc1cc(C)ccc1 Cc1ccc(C)cc1

Molar mass (/entry/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 (/entry/Density) and phase 0.864 g/mL, liquid 0.88 g/mL, liquid 0.86 g/mL, liquid 0.86 g/mL, liquid

Solubility in water practically insoluble

Soluble in non-polar solvents (/entry/Solvent) such as aromatic hydrocarbons (/entry/Hydrocarbon)

-47.4C (-53.3F; 25C (-13F; 248 48C (-54.4F; 13C (55.4F; 286
Melting point (/entry/Melting_point)
226 K) K) 225 K) K)

138.5C (281.3F; 144C (291.2F; 139C (282.2F; 138C (280.4F;

Boiling point (/entry/Boiling_point)
412 K) 417 K) 412 K) 411 K)

.812 cP at 20 C .62 cP at 20 C .34 cP at 30 C

Viscosity (/entry/Viscosity)
(68 F) (68 F) (86 F)

Hazards

MSDS Xylenes[1] o-Xylene[2] m-Xylene[3] p-Xylene[4]

EU Classification Harmful (Xn)

3
NFPA 704 2 0

(/entry/File:NFPA_704.svg)
Flash point 24 C (75 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 & properties n (/entry/Refractive_index), r (/entry/Dielectric_constant), etc.

Phase behaviour
Thermodynamic data
Solid, liquid, gas

Spectral data UV, IR, NMR, MS (/entry/Mass_spectrometry)

Related compounds
 Related aromatic
toluene (/entry/Toluene), mesitylene, benzene (/entry/Benzene), ethylbenzene
hydrocarbons (/entry/Hydrocarbon)

Related compounds xylenols - types of phenols

Except where noted otherwise, data are given for

materials in their standard state (at 25C, 100 kPa)

Applications
The xylenes are used as solvents (/entry/Solvent) and in the printing (/entry/Printing), rubber (/entry/Rubber), and
leather industries. p-Xylene is used as a feedstock in the production of terephthalic acid, which is a monomer used to
manufacture polymers (/entry/Polymer). The xylenes are also used as cleaning agents for steel (/entry/Steel), silicon
wafers, and integrated circuits (/entry/Integrated_circuit). They are found in pesticides (/entry/Pesticide), paint
thinners, paints (/entry/Paint), and varnishes (/entry/Varnish). A xylene mixture may be substituted for toluene
(/entry/Toluene) to thin lacquers where slower drying is desired. Xylene may be present in small amounts in airplane
fuel and gasoline (/entry/Gasoline). In animal studies, a xylene (or xylene mixture) is often swabbed on the ears of
rabbits to facilitate blood (/entry/Blood) flow and collection, although the area must be subsequently cleansed with
alcohol (/entry/Alcohol) to prevent inflammation.

Health effects
Xylene affects the brain (/entry/Brain). High levels from exposure for short periods (14 days or less) or long periods
(more than one year) can cause headaches, lack of muscle coordination, dizziness, confusion, and changes in one's
sense of balance. 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; problems with the lungs; delayed reaction time; memory difficulties;
stomach discomfort; and possibly changes in the liver and kidneys. It can cause unconsciousness and even death at
very high levels.

Studies of unborn animals (/entry/Animal) indicate that high concentrations of xylene may cause increased numbers
of deaths, and delayed growth and development. In many instances, these same concentrations also cause damage
to the mothers. It is not yet known whether xylene harms the unborn fetus (/entry/Fetus) if the mother is exposed to
low levels of xylene during pregnancy (/entry/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.

Another common form of human exposure to xylene is in the use of certain types of pens, writing and drawing
instruments, and art supplies.

See also
Benzene (/entry/Benzene)
Gasoline (/entry/Gasoline)
Organic chemistry (/entry/Organic_chemistry)
Paint (/entry/Paint)
Solvent (/entry/Solvent)
Toluene (/entry/Toluene)

Notes
1. Xylenes MSDS (http://sciencelab.com/msds.php?msdsId=9927646) ScienceLab.com. Retrieved January 4,
2008.
2. o-Xylene MSDS (http://sciencelab.com/msds.php?msdsId=9927647) ScienceLab.com. Retrieved January 4,
2008.
3. m-Xylene MSDS (http://sciencelab.com/msds.php?msdsId=9927323) ScienceLab.com. Retrieved January 4,
2008.
4. p-Xylene MSDS (http://sciencelab.com/msds.php?msdsId=9927324) ScienceLab.com. Retrieved January 4,
2008.

References
McMurry, John. 2004. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052
(http://www.amazon.com/dp/0534420052?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0534420052&adid=0NQQZXQ96PDAJGB1J8XS)
Morrison, Robert T., and Robert N. Boyd. 1992. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice Hall.
ISBN 0-13-643669-2 (http://www.amazon.com/dp/0136436692?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0136436692&adid=0NQQZXQ96PDAJGB1J8XS)
Solomons, T.W. Graham, and Craig B. Fryhle. 2004. Organic Chemistry. 8th ed. Hoboken, NJ: John Wiley.
ISBN 0471417998 (http://www.amazon.com/dp/0471417998?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0471417998&adid=0NQQZXQ96PDAJGB1J8XS)

External links
All links retrieved July 31, 2013.

NIOSH Pocket Guide to Chemical Hazards: o-Xylene (http://www.cdc.gov/niosh/npg/npgd0668.html)

NIOSH Pocket Guide to Chemical Hazards: m-Xylene (http://www.cdc.gov/niosh/npg/npgd0669.html)
NIOSH Pocket Guide to Chemical Hazards: p-Xylene (http://www.cdc.gov/niosh/npg/npgd0670.html)

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