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o-Xylene structure

o-Xylene
  • CAS：95-47-6
  • MW:106.17
  • MF：C8H10
o-Xylene, with the chemical formula C8H10 and CAS registry number 95-47-6, is a colorless, sweet-smelling liquid widely used as a solvent and in the production of various chemicals, less dense than water. Insoluble in water. Irritating vapor. It is a component of many petroleum products and is commonly found in gasoline and diesel fuels. o-Xylene is utilized in the manufacture of phthalic anhydride, which is a precursor to plasticizers and polyester resins. Additionally, it serves as a feedstock in the synthesis of other chemicals, including herbicides, insecticides, and dyes. This aromatic hydrocarbon is flammable and poses health hazards upon exposure, including irritation to the respiratory system and central nervous system depression. It is regulated in many countries due to its potential environmental and health impacts. View more+
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1. Names and Identifiers
1.1 Name
o-Xylene
1.2 Synonyms
1,2-DIMETHYLBENZENE; 1,2-dimethyl-benzene; 1，2-Xylene; 1,2-Xylene standard in Methanol; AKOS BBS-00004266; EINECS 202-422-2; MFCD00008519; O-Dimethylbenzene; ortho-Dimethylbenzene; Orthoxylene; O-XYLENE FOR SYNTHESIS; o-Xylol; XYLENES; XYLOL;
1.3 CAS No.
95-47-6
1.4 CID
7237
1.5 EINECS
202-422-2
1.6 Molecular Formula
C8H10
1.7 Inchi
InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
1.8 InChkey
CTQNGGLPUBDAKN-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=CC=CC=C1C
1.10 Isomers Smiles
CC1=CC=CC=C1C
2. Properties
2.1 Vapour pressure
3.7 (vs air)
2.2 Solubility
water: partially soluble0.1705 g/L at 25°C
2.3 Viscosity
0.760 mPa.s at 25 deg C
2.4 VaporDensity
3.7 (vs air)
2.5 Appearance
O-xylene appears as a colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor. (USCG, 1999)
2.6 Atmospheric OH Rate Constant
1.37e-11 cm3/molecule*sec
2.7 Storage
Ambient temperatures.
2.8 Chemical Properties
It appears as colorless transparent liquid with aromatic odor. It is miscible with ethanol, ethyl ether, acetone and benzene but insoluble in water.
2.9 Physical Properties
Clear, colorless liquid with an aromatic odor. An odor threshold concentration of 380 ppbv wasreported by Nagata and Takeuchi (1990).
2.10 Color/Form
Yellow to beige
2.11 Corrosivity
No reaction with common materials
2.12 Decomposition
Hazardous decomposition products formed under fire conditions - Carbon oxides.
2.13 Heat of Combustion
-17,558 Btu/lb = -9754.7 cal/g = -408.41 X 105 J/kg
2.14 Heat of Vaporization
43.43 kJ/mol at 25 deg C; 36.24 kJ/mol at 144.5 deg C
2.15 HenrysLawConstant
0.01 atm-m3/mole
2.16 Ionization Potential
8.56 eV
2.17 Odor
Sweet
2.18 Odor Threshold
0.05 ppm
2.19 pKa
>15 (Christensen et al., 1975)
2.20 Water Solubility
Sparingly soluble in water. (0.2g/L)
2.21 Spectral Properties
Index of refraction: 1.5058 at 20 deg C/D
Negligible absorption above 290 nm
IR: 3576 (Coblentz Society Spectral Collection)
UV: 7 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 201 (Varian Associates NMR Spectra Catalogue)
MASS: 63387 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version); 322 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Raman: 78 (Dollish et al, Characteristic Raman Frequencies of Organic Compounds, John Wiley and Sons, New York)
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2.22 Stability
Stable. Incompatible with oxidizing agents. Flammable. Hygroscopic.
2.23 StorageTemp
Store below +30°C.
2.24 Surface Tension
29.76 dynes/cm at 25 deg C
3. Use and Manufacturing
3.1 Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
3.2 Definition
ChEBI: A xylene substituted by methyl groups at positions 1 and 3.
3.3 Description
o-Xylene (CAS 95-47-6) is a colorless liquid with a sweet, aromatic odor. It has a basic structure consisting of a benzene ring with two methyl groups attached to it. This chemical is highly soluble in organic solvents such as ethanol and ether, but only slightly soluble in water. o-Xylene has a boiling point of 144.4°C and a melting point of -25.2°C. It is flammable and can form explosive mixtures with air. In terms of chemical properties, o-Xylene can undergo various reactions such as oxidation, halogenation, and nitration.

Applicable Fields
o-Xylene has several applications in different fields:

Chemical Industry: In the chemical industry, o-Xylene is used as a solvent for various purposes. It is commonly employed in the production of phthalic anhydride, which is a key ingredient in the manufacturing of plasticizers, polyester resins, and alkyd resins. The mechanism of action involves o-Xylene dissolving or dispersing other substances, allowing for efficient chemical reactions.

Paint and Coatings Industry: o-Xylene is also utilized in the paint and coatings industry as a solvent for paints, varnishes, and lacquers. It helps in achieving the desired consistency and viscosity of the products. The mechanism of action involves o-Xylene acting as a carrier for the pigments and binders, allowing for easy application and drying.

Adhesive Industry: In the adhesive industry, o-Xylene is used as a solvent in the production of various types of adhesives. It helps in dissolving the adhesive components and provides the necessary viscosity for application. The mechanism of action involves o-Xylene evaporating after application, allowing the adhesive to bond the surfaces together.

Storage Conditions
The storage conditions for o-Xylene are as follows: Store in a cool, well-ventilated area, away from ignition sources and heat. Keep the container tightly closed and upright to prevent leakage. Avoid direct sunlight and exposure to flames or sparks.
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3.4 General Description
A colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor.
3.5 Purification Methods
o-Xylene (4.4Kg) is sulfonated by stirring for 4hours with 2.5L of conc H2SO4 at 95o. After cooling, and separating the unsulfonated material, the product is diluted with 3L of water and neutralised with 40% NaOH. On cooling, sodium o-xylene sulfonate separates and is recrystallised from half its weight of water. [A further crop of crystals is obtained by concentrating the mother liquor to one-third of its volume.] The salt is dissolved in the minimum amount of cold water, then mixed with the same amount of cold water, and with the same volume of conc H2SO4 and heated to 110o. o-Xylene is regenerated and steam distils. The distillate is saturated with NaCl, the organic layer is separated, dried and redistilled. [Beilstein 5 H 362, 5 I 179, 5 II 281, 5 III 807, 5 IV 917.] o-Xylene Preparation Products And Raw materials Raw materials
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3.6 Usage
(1) It is mainly used in the production of phthalic anhydride(2) O-xylene is the raw material for the production of germicide fenramine, tetrachlorophenyl peptide and the herbicide bensulfuron-methyl. It is used as intermediate for the manufacture of o-methyl benzoic acid.(3) It is mainly used as chemical raw materials and solvents. It can be used to produce phthalic anhydride, dyes, pesticides and drugs, such as vitamins. It can also be used as aviation gasoline additives.(4) Used as chromatographic standards and solvents(5) As raw materials of synthesis of anhydride and other organic synthesis;
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4. Safety and Handling
4.1 Octanol/Water Partition Coefficient
log Kow = 3.12
4.2 Fire Hazard
Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.
4.3 Other Preventative Measures
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. ... /Xylenes/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. All contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Skin that becomes contaminated with xylene should be promptly washed with soap or mild detergent and water to remove any xylene. Employees who handle liquid or solid xylene should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Xylenes/
A major concern in the painting studio is solvents, /including xylene/. ... Precautions include ... use of dilution and local exhaust ventilation, control of storage areas, disposal of solvent soaked rags in covered containers, minimizing skin exposure and the use of respirators and other personal protective equipment. The control of fire hazards is also important, since many of the solvents are highly flammable. /Xylenes/
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Xylenes/
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
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4.4 Cleanup Methods
Stop discharge if possible. Keep people away. Call fire department. Avoid contact with liquid and vapor. Isolate and remove discharged material. Notify local health and pollution control agencies.
1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear hood ductwork. Burn paper in suitable location away from combustible materials. Large quantities can be reclaimed or collected & atomized in suitable combustion chamber. Xylene should not be allowed to enter confined space, such as sewer. ... /Xylenes/
For spills on land, absorb remaining xylene with sand or vermiculite and put in metal containers for disposal. Activated carbon may be used on undissolved portion. /Xylenes/
For spills on water, contain and apply a universal gelling agent to solidify trapped mass then remove it. /Xylenes/
Soil: construct barriers to contain spill or divert to impermeable holding area. Remove material with pumps or vacuum equipment. Absorb residual liquid with natural or synthetic sorbents, shovel into containers with covers. /Xylenes/
Water: contain with booms, weirs, or natural barriers. Use (oil) skimming equipment or suction hoses to remove slick, followed by application of sorbents. /Xylenes/
Air: use water spray to control flammable vapor. Control runoff for later treatment and/or disposal. /Xylenes/
Spillage Disposal: Shut off all possible sources of ignition. Wear face shield, goggles, laboratory coat, and nitrile rubber gloves. Cover spill with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite) and sand, then shovel into bucket and transport to fume hood for atmospheric evaporation. Ventilate site of spillage well to evaporate remaining liquid and dispel vapor. /Xylenes/
Environmental considerations - air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment. /Xylenes/
Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Use surface active agent (eg, detergent, soaps, alcohols), if approved by EPA. Inject "universal" gelling agent to solidify encircled spill and increase effectiveness of booms. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. /Xylenes/
Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply "universal" gelling agent to immobilize spill. Apply appropriate foam to diminish vapor and fire hazard. /Xylenes/
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4.5 DisposalMethods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U239 and F003, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Xylenes/
Xylene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. /Xylenes/
A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. /Xylenes/
Recommendable methods: Incineration, use as a boiler fuel, & evaporation.
Xylene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
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4.6 DOT Emergency Guidelines
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Xylenes/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Xylenes/
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4.7 Fire Fighting Procedures
Foam, dry chemical, or carbon dioxide. Water may be ineffective. Cool exposed containers with water.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Xylenes/
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4.8 Safety Profile
Moderately toxic bj7intraperitoneal route. Mldly toxic byingestion and inhalation. An experimentalteratogen. A common air contaminant. Avery dangerous fire hazard when exposed toheat or flame. Explosive in the form ofvapor when exposed to heat or flame. Tofight fire, use foam, CO2, dry chemical.Incompatible with oxidzing materials.When heated to decomposition it emitsacrid smoke and irritating fumes. Emittedfrom modern building materials (CENEAR69,22,91). See also other xylene entries.
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4.9 Formulations/Preparations
Grade: 99%, free of hydrogen sulfide and sulfur dioxide; technical 95%; research 99.9%
4.10 Protective Equipment and Clothing
Approved canister or air-supplied mask; goggles or face shield; plastic gloves & boots.
Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum) ... to prevent repeated or prolonged skin contact with liquid or solid xylene. Clothing contaminated with xylene should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of xylene from the clothing. If the clothing is to be laundered ... the person performing the operation should be informed of xylene's hazardous properties. /Xylenes/
Breakthrough times /for natural rubber, neoprene, and polyvinyl chloride/ less (usually significantly less) than one hr reported by (normally) two or more testers. Breakthrough times /for polyvinyl alcohol/ greater than one hr reported by (normally) two or more testers. Some data suggesting breakthrough times /for nitrile rubber/ of approx an hour or more. /Xylenes/
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 900 ppm Assigned Protection Factor (APF) Respirator Recommendation APF = 10 Any chemical cartridge respirator with organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection. APF = 25 Any powered, air-purifying respirator with organic vapor cartridge(s). Substance reported to cause eye irritation or damage; may require eye protection. APF = 10 Any supplied-air respirator. Substance reported to cause eye irritation or damage; may require eye protection. APF = 50 Any self-contained breathing apparatus with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
Personnel protection: ... Wear appropriate chemical protective clothing. Wear positive pressure self-contained breathing apparatus.
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4.11 Reactivities and Incompatibilities
An attempt to chlorinate xylene with 1,3-dichloro-5,5-dimethyl-2,4-imidazolidindione (dichlorohydrantoin) caused a violent explosion. The haloimide undergoes immediate self accelerating decomp in the presence of solvents. /Xylenes/
Strong oxidizers, strong acids.
4.12 Skin, Eye, and Respiratory Irritations
Xylene vapor may cause irritation of the eyes, nose, and throat. At high concentrations, xylene vapor may cause severe breathing difficulties which may be delayed in onset. /Xylenes/
Vapor irritates eyes and mucous membranes ... Liquid irritates eyes and mucous membranes. /Xylenes/
Human data indicate that acute inhalation exposures to 460 ppm mixed xylene and 100 ppm p-xylene vapors produce mild and transient eye irritation ... . This effect is probably the result of direct contact of the xylene vapor with the eye.
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4.13 Toxicity
Acute oral LD50 in rats is approximately 5 g/kg (quoted, RTECS, 1992).
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H226 Flammable liquid and vapour

H312 Harmful in contact with skin

H315 Causes skin irritation

H332 Harmful if inhaled
Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P264 Wash ... thoroughly after handling.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P332+P313 If skin irritation occurs: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
1H NMR : 400 MHz in CDCl3  
IR : liquid film  
Raman : 4880 A,200 M,liquid  
Mass  
7. Synthesis Route
95-47-6Total: 190 Synthesis Route
 
89-95-2
89-95-2 78 Suppliers
 
95-47-6
95-47-6 160 Suppliers
 
85-44-9
85-44-9 310 Suppliers
 
95-47-6
95-47-6 160 Suppliers
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8. Precursor and Product
precursor:
95-63-6
95-63-6
89-92-9
89-92-9
95-48-7
95-48-7
84-66-2
84-66-2
87-41-2
87-41-2
89-95-2
89-95-2
91-20-3
91-20-3
85-44-9
85-44-9
95-46-5
95-46-5
product:
88-99-3
88-99-3
91-15-6
91-15-6
83-41-0
83-41-0
89-92-9
89-92-9
99-51-4
99-51-4
89-95-2
89-95-2
85-44-9
85-44-9
95-65-8
95-65-8
78-98-8
78-98-8
91-13-4
91-13-4
9. Computed Properties
10.Other Information
Usage
o-Xylene is widely used in the production of phthalic anhydride. It is also used in fuels as well as fuel additives. It can be used in the production of isophthalic acid and terephthalic acid. It is utilized in polyvinyl chloride production, alkyl resin and unsaturated polyester resins. It is also used as a solvent in paint, varnish, glue, printing ink, dyes and in rubber.
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Usage
o-Xylene is largely used in the production of phthalic anhydride, and is generally extracted by distillation from a mixed Xylene stream in a plant primarily designed for p-Xylene production.
Usage
o-Xylene is used as a solvent for paints and adhesives, and to make other chemicals.
Merck
14,10081
BRN
1815558
Xylene
Xylene refers to the aromatic hydrocarbon with the two hydrogen atoms on the benzene ring being substituted by two methyl groups. It has three isomers o-xylene (1, 2-Dimethylbenzene), m-xylene and p-xylene. The industrial products are the mixtures of the three isomers with 10% o-10%, 70% m-, and 20% p-. In the coking industry, it is one of crude benzene refined products.
Xylene is a kind of colorless flammable liquid; the melting point of o-, m-and p-xylene is-25.2 ℃,-47.9 ℃ and 13.3 ℃; the boiling points are respectively 144.4 ℃, 139.1 ℃ and 138.3 ℃ while the relative density is 0.8802, 0.8642 and 0.8611, respectively; It is not soluble in water but miscible with many kinds of organic solvents immiscibility. Upon catalytic oxidation, they respectively, generate phthalic anhydride, isophthalic acid and terephthalic acid.
Xylene is one kind of important raw materials of organic chemicals, naturally existing in coal tar and some kinds of petroleum. It can be obtained through the fractionation of the light oil part of the coal tar or catalytic reforming light gasoline. Industry mainly performs extracting using the C8 fraction in the naphtha reformates. It can be alternatively manufactured through the disproportionation reaction of toluene in the presence of catalyst and high temperature, high pressure. At present time, industry mainly applies the method of cryogenic crystallization, adsorption and formation of complexes or molecular sieves to separate them. O-xylene has a relatively high boiling point, being able to be separated using distillation. p-xylene also has a high melting point and can be purified through fractional crystallization purification. Mixed xylene without separation can be directly used as a solvent with being supplemented to the gasoline capable of improving the anti-explosive properties. They are components of aviation gasoline. O-xylene is mainly used for the preparation of phthalic anhydride, which is an important raw material for the manufacture of a variety of dyes and indicators (such as phenolphthalein). In addition, o-xylene can also be used for preparation of polyester resin, insect repellent, plasticizers and dyes. M-xylene, through nitration and reduction, can generate 4, 6-dimethyl-1, 3-phenylenediamine that is the intermediate for synthetic dyes. M-xylene can also be used as the raw materials for synthetic fragrances (such as xylene musk). P-xylene is mainly used in the manufacture of terephthalic acid, which is an important raw material for synthetic polyester fiber (polyester).
  the chemical structure of the three isomers of xylene, ortho-xylene, m-xylene, p-xylene chemical structure
Figure 1 the chemical structure of the three isomers of xylene, ortho-xylene, m-xylene, p-xylene chemical structure.
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Precision Distillation for separation of O-xylene and p-xylene
Xylene is presented in coked crude benzene and petroleum cracked oil. Crude benzene, after initial distillation, sulfuric acid washing and distillation for separation of benzene and toluene, followed by distillation, we can obtain xylene, also known as coking xylene. The quality of the coked xylene depends on the separation capacity of the distillation column, the temperature at the top of the column and the reflux ratio. China has classified the coking xylene products into three levels. The coking xylene generally contains 16% if o-xylene, 50% of m-xylene, 21% of p-xylene and 7% of ethylbenzene. The xylene produced in the petroleum industry has a low content of m-xylene and a high content of ethylbenzene. Industrial xylene is not only the solvent and additive of rubber and coatings industry, but also the additives of aviation and power fuel. O-xylene, m-xylene and p-xylene separated from industrial xylene are the raw materials of phthalic acid, isophthalic acid and terephthalic acid, respectively. Phthalic acid and terephthalic acid are used in the production of plasticizers, polyester resins and polyester fibers. M-xylene can be used alone as solvent and fuel additives. The o-xylene contained in the industrial xylene has a over 5.2 ℃ difference with other isomers. With precision distillation, we can obtain o-xylene with a purity of over 95%, followed by using sulfonation and distillation for purification so we can get further purer o-xylene. 
Xylene belongs to Lewis base, which can form a polar complex with HF-BF3 (Lewis acid). The alkalinity of M-xylene is about 100 times as strong as that of other C8 aromatics. When the isomer mixture of xylene comes into contact with HF-BF3 solvent, m-xylene can form a complex with fluoride and is preferentially extracted into the fluoride phase. The m-xylene-containing fluoride phase is heated at a lower pressure to decompose the complex, thereby separating m-xylene from the mixture. HF-BF3 solvent can be recovered by distillation for recycling. If the raw material is a mixture of ortho-xylene, m-xylene and p-xylene, after the m-xylene is extracted, we can further use precision distillation to separate the o-xylene and p-xylene.

Figure 2 the precision distillation method for separation of o-xylene and p-xylene.
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Chemical properties
It appears as colorless transparent liquid with aromatic odor. It is miscible with ethanol, ethyl ether, acetone and benzene but insoluble in water.
Uses
(1)  It is mainly used in the production of phthalic anhydride
(2)  O-xylene is the raw material for the production of germicide fenramine, tetrachlorophenyl peptide and the herbicide bensulfuron-methyl. It is used as intermediate for the manufacture of o-methyl benzoic acid.
(3)  It is mainly used as chemical raw materials and solvents. It can be used to produce phthalic anhydride, dyes, pesticides and drugs, such as vitamins. It can also be used as aviation gasoline additives.
(4)  Used as chromatographic standards and solvents
(5)  As raw materials of synthesis of anhydride and other organic synthesis;
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Production method
Industry applied super-distillation method to separate out the o-xylene from the mixed xylene. O-xylene has a over 5 ℃ difference in the boiling point compared with other components in the mixed xylene. For the distillation, the required tray number is about 150; the reflux ratio being 5-8 and consume relative much energy.
O-xylene was originally produced mainly from coal tar. Currently most of the domestic and foreign production of o-xylene is mainly via extraction from oil catalytic reforming and thermal cracking of aromatic hydrocarbon. Owing to that the structures of o-xylene, p-xylene, and m-xylene in the xylene are very similar; their physical parameters are also quite similar. Industrial o-xylene separation mainly adopts super-distillation method; first separate out the o-xylene and ethylbenzene from the mixed xylene which demands the using of 100~150 tray distillation tower; followed by separation of o-xylene and ethylbenzene to obtain pure o-xylene.
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Category
Flammable liquids
Toxicity grading
poisoning
Acute toxicity
Oral-rat LDL0: 5000 mg/kg; abdominal injection-mouse LD50: 1364 mg/kg
EXPLOSIVES and HAZARDOUS CHARACTERISTICS
being explosive when mixed with air
Flammability and Hazardous characteristics
being flammable upon flame, heat, oxidant Flammable with combustion releasing irritant smoke
Storage and transportation characteristics
warehouse: ventilated, low temperature and dry; gently load and unload; store it separately from oxidants and acids.
Fire extinguishing agent
mist water, foam, sand, carbon dioxide, 1211 extinguishing agent
Occupational Standard
TLV-TWA 100 PPM (440 mg/m 3); STEL 150; PPM (655 mg/m 3)
Chemical Properties
colourless liquid
Physical properties
Clear, colorless liquid with an aromatic odor. An odor threshold concentration of 380 ppbv was reported by Nagata and Takeuchi (1990).
Uses
Preparation of phthalic acid, phthalic anhydride, terephthalic acid, isophthalic acid; solvent for alkyd resins, lacquers, enamels, rubber cements; manufacture of dyes, pharmaceuticals, and insecticides; motor fuels.
Uses
Xylene, xylenes, and total xylenes are used interchangeably since xylene usually exists as a mixture of three isomers: 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene, i.e., o-, m-, and p-xylene, and is usually used as a mixture of the three forms. The mixture often also contains ethylbenzene. It is a high volume industrial chemical used in the synthetic fiber, chemical and plastics industries and as a solvent, cleaning agent and thinner for paints and varnishes.
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Definition
ChEBI: A xylene substituted by methyl groups at positions 1 and 3.
Synthesis Reference(s)
Journal of the American Chemical Society, 97, p. 7262, 1975 DOI: 10.1021/ja00858a011
The Journal of Organic Chemistry, 44, p. 2185, 1979 DOI: 10.1021/jo01327a032
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General Description
A colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
1,2-Dimethylbenzene may react with oxidizing materials. .
Health Hazard
Vapors cause headache and dizziness. Liquid irritates eyes and skin. If taken into lungs, causes severe coughing, distress, and rapidly developing pulmonary edema. If ingested, causes nausea, vomiting, cramps, headache, and coma. Can be fatal. Kidney and liver damage can occur.
Fire Hazard
Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Moderately toxic bj7 intraperitoneal route. Mldly toxic by ingestion and inhalation. An experimental teratogen. A common air contaminant. A very dangerous fire hazard when exposed to heat or flame. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Incompatible with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes. Emitted from modern building materials (CENEAR 69,22,91). See also other xylene entries.
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Source
Detected in distilled water-soluble fractions of 87 octane gasoline (3.83 mg/L), 94 octane gasoline (11.4 mg/L), Gasohol (8.49 mg/L), No. 2 fuel oil (1.73 mg/L), jet fuel A (0.87 mg/L), diesel fuel (1.75 mg/L), military jet fuel JP-4 (1.99 mg/L) (Potter, 1996), new motor oil (16.2 to 17.5 μg/L), and used motor oil (294 to 308 μg/L) (Chen et al., 1994). The average volume percent and estimated mole fraction in American Petroleum Institute PS-6 gasoline are 2.088 and 0.01959, respectively (Poulsen et al., 1992). Schauer et al. (1999) reported o-xylene in a diesel-powered medium-duty truck exhaust at an emission rate of 830 μg/km. Diesel fuel obtained from a service station in Schlieren, Switzerland contained o-xylene at a concentration of 223 mg/L (Schluep et al., 2001).
California Phase II reformulated gasoline contained o-xylene at a concentration of 19.7 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 5.41 and 562 mg/km, respectively (Schauer et al., 2002).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average m+p-xylene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 8.611, 0.658, and 0.228 mg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average m+p-xylene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were lower, i.e., 6.068, 0.360, and 0.222 mg/L, respectively. Based on laboratory analysis of 7 coal tar samples, o-xylene concentrations ranged from 2 to 2,000 ppm (EPRI, 1990). A high-temperature coal tar contained o-xylene at an average concentration of 0.04 wt % (McNeil, 1983).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of o-xylene was 18.1 mg/kg of pine burned. Emission rates of o-xylene were not measured during the combustion of oak and eucalyptus.
Drinking water standard (final): For all xylenes, the MCLG and MCL are both 10 mg/L. In addition, a DWEL of 70 mg/L was recommended (U.S. EPA, 2000).
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Environmental fate
Biological. Reported biodegradation products of the commercial product containing xylene include α-hydroxy-p-toluic acid, p-methylbenzyl alcohol, benzyl alcohol, 4-methylcatechol, mand p-toluic acids (Fishbein, 1985). o-Xylene was also cometabolized resulting in the formation of o-toluic acid (Pitter and Chudoba, 1990). In anoxic groundwater near Bemidji, MI, o-xylene anaerobically biodegraded to the intermediate o-toluic acid (Cozzarelli et al., 1990). In gasolinecontaminated groundwater, methylbenzylsuccinic acid was identified as the first intermediate during the anaerobic degradation of xylenes (Reusser and Field, 2002).
Photolytic. Cox et al. (1980) reported a rate constant of 1.33 x 10-11 cm3/molecule?sec for the reaction of gaseous o-xylene with OH radicals based on a value of 8 x 10-12 cm3/molecule?sec for the reaction of ethylene with OH radicals.
Surface Water. The evaporation half-life of o-xylene in surface water (1 m depth) at 25 °C is estimated to be 5.18 h (Mackay and Leinonen, 1975).
Groundwater. Nielsen et al. (1996) studied the degradation of o-xylene in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine o-xylene concentrations with time. The experimentally determined firstorder biodegradation rate constant and corresponding half-life following a 7-d lag phase were 0.1/d and 6.93 d, respectively.
Photolytic. When synthetic air containing gaseous nitrous acid and o-xylene was exposed to artificial sunlight (λ = 300–450 nm) biacetyl, peroxyacetal nitrate, and methyl nitrate formed as products (Cox et al., 1980). A n-hexane solution containing o-xylene and spread as a thin film (4 mm) on cold water (10 °C) was irradiated by a mercury medium pressure lamp. In 3 h, 13.6% of the o-xylene photooxidized into o-methylbenzaldehyde, o-benzyl alcohol, o-benzoic acid, and omethylacetophenone (Moza and Feicht, 1989). Irradiation of o-xylene at ≈ 2537 ? at 35 °C and 6 mmHg isomerizes to m-xylene (Calvert and Pitts, 1966). Glyoxal, methylglyoxal, and biacetyl were produced from the photooxidation of o-xylene by OH radicals in air at 25 °C (Tuazon et al., 1986a).
Chemical/Physical. Under atmospheric conditions, the gas-phase reaction of o-xylene with OH radicals and nitrogen oxides resulted in the formation of o-tolualdehyde, o-methylbenzyl nitrate, nitro-o-xylenes, 2,3-and 3,4-dimethylphenol (Atkinson, 1990). Kanno et al. (1982) studied the aqueous reaction of o-xylene and other aromatic hydrocarbons (benzene, toluene, m- and p-xylene, and naphthalene) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride formed increased at lower pHs (Kanno et al., 1982). In the gas phase, o-xylene reacted with nitrate radicals in purified air forming the following products: 5-nitro-2-methyltoluene and 6-nitro-2-methyltoluene, o-methylbenzaldehyde, and an aryl nitrate (Chiodini et al., 1993).
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Purification Methods
o-Xylene (4.4Kg) is sulfonated by stirring for 4hours with 2.5L of conc H2SO4 at 95o. After cooling, and separating the unsulfonated material, the product is diluted with 3L of water and neutralised with 40% NaOH. On cooling, sodium o-xylene sulfonate separates and is recrystallised from half its weight of water. [A further crop of crystals is obtained by concentrating the mother liquor to one-third of its volume.] The salt is dissolved in the minimum amount of cold water, then mixed with the same amount of cold water, and with the same volume of conc H2SO4 and heated to 110o. o-Xylene is regenerated and steam distils. The distillate is saturated with NaCl, the organic layer is separated, dried and redistilled. [Beilstein 5 H 362, 5 I 179, 5 II 281, 5 III 807, 5 IV 917.]
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Storage features
Fireproof. Separated from strong oxidants and strong acids.
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12. Related Questions
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