![]() | |
![]() Space-filling model | |
Names | |
---|---|
Preferred IUPAC name 1,4-Xylene [1] | |
Systematic IUPAC name 1,4-dimethylbenzene | |
Other names | |
Identifiers | |
3D model (JSmol) | |
1901563 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.088 |
EC Number |
|
2697 | |
KEGG | |
PubChem CID | |
RTECS number |
|
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C8H10 | |
Molar mass | 106.168 g·mol−1 |
Appearance | Colorless liquid |
Odor | Aromatic [5] |
Density | 0.861 g/mL |
Melting point | 13.2 °C (55.8 °F; 286.3 K) |
Boiling point | 138.35 °C (281.03 °F; 411.50 K) |
Insoluble | |
Solubility in ethanol | Very soluble |
Solubility in diethyl ether | Very soluble |
Vapor pressure | 9 mmHg (20°C) [5] |
-76.78·10−6 cm3/mol | |
Refractive index (nD) | 1.49582 |
Viscosity | 0.7385 cP at 0 °C 0.6475 cP at 20 °C |
0.00 D [6] | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Harmful or if swallowed. Vapor maybe toxic. [7] Flammable liquid and vapor. |
GHS labelling: | |
![]() ![]() ![]() | |
Danger | |
H226, H302, H304, H312, H315, H319, H332, H335, H412 | |
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P331, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 27 °C (81 °F; 300 K) [8] |
528 °C (982 °F; 801 K) [8] | |
Explosive limits | 1.1%-7.0% [5] |
Threshold limit value (TLV) | 100 ppm [8] (TWA), 150 ppm [8] (STEL) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 4300 mg/kg [9] |
LC50 (median concentration) | 4550 ppm (rat, 4 hr) [10] |
LCLo (lowest published) | 3401 ppm (mouse) [10] |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 100 ppm (435 mg/m3) [5] |
REL (Recommended) | TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3) [5] |
IDLH (Immediate danger) | 900 ppm [5] |
Safety data sheet (SDS) | External MSDS |
Related compounds | |
Related aromatic hydrocarbons | benzene toluene o-xylene m-xylene |
Supplementary data page | |
P-Xylene (data page) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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). [11]
The production of p-xylene is industrially significant, with annual demand estimated at 37 million tons in 2014, and still on the increase. [12] [13] p-Xylene is produced by catalytic reforming of petroleum naphtha as part of the BTX aromatics (benzene, toluene and the xylene isomers) extracted from the catalytic reformate. The p-xylene is then separated out in a series of distillation, adsorption or crystallization and reaction processes from the m-xylene, o-xylene, and ethylbenzene. Its melting point is the highest among this series of isomers, but simple crystallization does not allow easy purification due to the formation of eutectic mixtures.
Such separation procedures are major cost factors in the production of p-xylene, and the search for alternative methods continues. For example, a reverse-osmosis technique has been proposed to improve various aspects of the processes. [14]
p-Xylene is an important chemical feedstock. Among other industrial applications, it is a raw material in the large scale synthesis of various polymers. In particular it is a component in the production of terephthalic acid for polyesters such as polyethylene terephthalate (generally known as PET). It also may be polymerised directly to produce parylene.
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. Overexposure of p-xylene in humans can cause headache, fatigue, dizziness, listlessness, confusion, irritability, gastrointestinal disturbances including nausea and loss of appetite, flushing of the face, and a feeling of increased body heat. p-Xylene vapor exposure over the recommended exposure limit of 100 parts per million (ppm) can cause irritation to eye, nose, and throat and possible chest tightening and an abnormal gait. [15]
p-Xylene occurs naturally in petroleum and coal tar. It is emitted by most combustion sources, including automobile exhaust and tobacco smoke. [16]
Inhaling p-xylene can cause dizziness, headache, drowsiness, and nausea. If exposure through inhalation occurs, first aid includes fresh air, rest and possible medical attention. Through the use of ventilation or breathing protection, exposure to p-xylene through inhalation can be prevented. [17]
Exposure of p-xylene through the skin can cause dry skin and redness. If skin exposure occurs, first aid includes rinsing and then washing the affected area with soap and water as well as removing any contaminated clothing and thoroughly cleaning and drying before reuse. Exposure can be prevented through the use of protective gloves. [17]
Exposure of p-xylene to eyes can cause redness and pain. If eyes are exposed, first aid includes rinsing of the eyes with water for several minutes, removal of contact lenses if applicable, and medical attention. Eye exposure can be prevented through the use of safety glasses or safety goggles. [17]
Ingestion of p-xylene can result in a burning sensation, abdominal pain, dizziness, drowsiness, headache, and nausea. If p-xylene is ingested one's mouth should be rinsed and vomiting should not be induced. Further medical attention should be sought. Ingestion can be prevented by not eating, drinking, or smoking when working with p-xylene. [17]
p-Xylene can cause issues with the central nervous system and if swallowed could cause chemical pneumonitis when breathed into the lungs. [17]
Liquid p-xylene exposure to the skin over long periods of time can remove the fat from the skin. The substance may also have effects on the central nervous system. Exposure can enhance hearing loss caused by noise exposure. Animal tests suggest that this substance could cause damage to human development and reproductive systems. [17]
Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for the 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.
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.
Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.
Chemical hazards are hazards present in hazardous chemicals and hazardous materials. Exposure to certain chemicals can cause acute or long-term adverse health effects. Chemical hazards are usually classified separately from biological hazards (biohazards). Chemical hazards are classified into groups that include asphyxiants, corrosives, irritants, sensitizers, carcinogens, mutagens, teratogens, reactants, and flammables. In the workplace, exposure to chemical hazards is a type of occupational hazard. The use of personal protective equipment may substantially reduce the risk of adverse health effects from contact with hazardous materials.
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.
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.
Germane is the chemical compound with the formula GeH4, and the germanium analogue of methane. It is the simplest germanium hydride and one of the most useful compounds of germanium. Like the related compounds silane and methane, germane is tetrahedral. It burns in air to produce GeO2 and water. Germane is a group 14 hydride.
Cadmium fluoride (CdF2) is a mostly water-insoluble source of cadmium used in oxygen-sensitive applications, such as the production of metallic alloys. In extremely low concentrations (ppm), this and other fluoride compounds are used in limited medical treatment protocols. Fluoride compounds also have significant uses in synthetic organic chemistry. The standard enthalpy has been found to be -167.39 kcal. mole−1 and the Gibbs energy of formation has been found to be -155.4 kcal. mole−1, and the heat of sublimation was determined to be 76 kcal. mole−1.
sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.
1,1,2-Trichloroethane, vinyl trichloride or 1,1,2-TCA, is an organochloride solvent with the molecular formula C2H3Cl3 and the structural formula CH2Cl—CHCl2. It is a colourless, sweet-smelling liquid that does not dissolve in water, but is soluble in most organic solvents. It is an isomer of 1,1,1-trichloroethane, and a byproduct of its manufacture.
Xylidine can refer to any of the six isomers of xylene amine, or any mixture of them.
Butane-1-thiol, also known as butyl mercaptan, is a volatile, clear to yellowish liquid with a fetid odor, commonly described as "skunk" odor. In fact, 1-butanethiol is structurally similar to several major constituents of a skunk's defensive spray but is not actually present in the spray. The scent of 1-butanethiol is so strong that the human nose can easily detect it in the air at concentrations as low as 10 parts per billion. The threshold level for 1-butanethiol is reported as 1.4 ppb
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.
1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.
Thiram is the simplest thiuram disulfide and the oxidized dimer of dimethyldithiocarbamate. It is used as a fungicide, ectoparasiticide to prevent fungal diseases in seed and crops and similarly as an animal repellent to protect fruit trees and ornamentals from damage by rabbits, rodents and deer. It is effective against Stem gall of coriander, damping off, smut of millet, neck rot of onion, etc. Thiram has been used in the treatment of human scabies, as a sun screen and as a bactericide applied directly to the skin or incorporated into soap.
Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V-sub x and GD-7.
EPN is an insecticide of the phosphonothioate class. It is used against pests such as European corn borer, rice stem borer, bollworm, tobacco budworm, and boll weevil.
Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.
n-Butyl lactate is an industrial chemical and food additive.
{{cite web}}
: Missing or empty |url=
(help)