P-Xylene

HCID 7809CAS 106-42-3

Basic information

Standard SMILES
Cc1ccc(C)cc1
InChIKey
URLKBWYHVLBVBO-UHFFFAOYSA-N
Molecular formula
C8H10
Average molar mass
106.16 g/mol
Monoisotopic mass
106.07825032

Overview

P-xylene appears as a colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor. Freezing point is 56 °F. (USCG, 1999)

Names & identifiers

Preferred name
P-Xylene
IUPAC
1,4-xylene
English name
P-XYLENE
Molecular formula
C8H10
Molecular weight
106.17

Names & synonyms

P-XYLENE106-42-31,4-DimethylbenzenePara-Xylene1,4-Xylenep-Methyltoluenep-Dimethylbenzenep-XylolBenzene, 1,4-dimethyl-4-Xylene4-MethyltolueneChromar
Show more names
p-Xylene (1.4-p-Xylene for HPLC, >=99%
Scintillar1,4-DimethylbenzolparaxyleneDTXSID20218686WAC1O477VNSC-72419DTXCID701868CHEBI:27417

Database identifiers

CAS
106-42-3、116598-94-8
PubChem CID
7809
DTXSID
DTXSID2021868
ChEMBL
CHEMBL31561
ChEBI
CHEBI:27417
UNII
6WAC1O477V
EC Number
203-396-5
Nikkaji
J3.609I

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Aromatic Solvents
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 items

log Kow = 3.15

3.15

3.42

Odor · 3 items

Sweet

Aromatic odor

Characteristic odor

Density · 5 items

0.861 at 68 °F (USCG, 1999) - Less dense than water; will float

0.86104 at 20 °C/4 °C

Critical density: 2.64 mmol/cu cm; Critical volume: 379.0 cu cm/mol

Relative density (water = 1): 0.86 (20 °C)

0.86

Physicochemical properties

Melting point
12 · 12-13 °C (lit.)
Boiling point
138 °C · 138 °C (lit.)
Density
0.861 g/mL · 0.861 g/mL at 20 °C (lit.)
vapor density
3.7 · 3.7 (vs air)
vapor pressure
9 mm · 9 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.495(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P317, P321, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.8% (11 of 1380) of reports.

Danger

H226 (99.2%): Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: Benzene, 1,4-dimethyl-

Benzene, 1,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,4-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 19-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15791

Benzene, 1,4-dimethyl-: HSNO Approval: HSR001048 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Xylenes: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 2 items

Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. (USCG, 1999)

Flammable. Above 25 °C explosive vapour/air mixtures may be formed.

Health Hazards · 1 item

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. (USCG, 1999)

Hazards Summary · 2 items

A skin and eye irritant; May have CNS effects; An aspiration hazard by ingestion (may cause chemical pneumonitis); May have adverse effects on human reproduction or development, based on animal studies; [ICSC] May cause smarting and reddening of skin if spilled and allowed to remain on clothes; High vapor concentrations may cause mild smarting of eyes and respiratory system; May cause liver and kidney injury; [CHRIS] A local irritant; Inhalation of high concentrations may cause narcotic effects, severe coughing, and pulmonary edema; Ingestion may cause kidney and liver injury; [NTP] A skin irritant; Harmful by inhalation and skin absorption; May cause narcosis, lung irritation, chest pain, pulmonary edema, CNS depression, blood disorders, liver and kidney injury, and reproductive disorders; [Sigma-Aldrich MSDS] An OTO notation is recommended for p-xylene based on human and animal ototoxicity data. [2021 ACGIH] See Xylene isomers.

The major hazards encountered in the use and handling of 4-xylene stem from its toxicologic properties and flammability. Exposure to this colorless sweet-smelling liquid (solid, below 13 °C) may occur from its use as a solvent, as a component of gasoline, and as a chemical intermediate. Toxic by all routes of exposure (ie, dermal, ingestion, and inhalation), 4-xylene can cause effects including headache, dizziness, skin and eye irritation, kidney and liver damage, pulmonary edema, coma, and death. The ACGIH recommends a workplace exposure limit (TLV) of 100 ppm an 8-hr time-weighted average (TWA); however, to assure protection, wear an approved canister or air-supplied mask, face shield, plastic gloves, and boots. In emergency situations, a self-contained breathing apparatus and full protective clothing are recommended. If contact does occur, immediately flush exposed eyes with running water, wash exposed skin with soap and water, and remove contaminated clothing. Individuals with diseases of the central nervous system, liver, kidneys, and blood should be protected from exposure. 4-Xylene is easily ignitable by heat, sparks, or flame (flash point: 25 °C, closed cup), and may do so explosively in an enclosed area. Also, vapor may travel a considerable distance to a source of ignition and flash back. The heat of a fire may cause containers to explode and/or cause thermal degradation of 4-xylene, producing irritating and poisonous gases. Fires involving 4-xylene may be extinguished with dry chemical, CO2, water spray, fog, or foam. For massive fires in enclosed areas, use unmanned hose holders or monitor nozzles. If a 4-xylene tank car or truck is involved in a fire, isolate 1/2 mile in all directions. Runoff from fire control water may cause pollution and, upon entering a sewer, may create an explosion hazard. 4-Xylene should be stored in closed containers, in cool, well ventilated areas (outdoor or detached areas are preferable), away from sources of ignition, oxidizing agents, and any activity that could cause physical damage to containers. For small spills of 4-xylene, take up with sand or other non-combustible absorbent and place in containers for later disposal, or absorb on paper and evaporate in an appropriate exhaust hood. For large spills, isolate the area, dike far ahead of the spill, and collect the material for disposal. 4-Xylene is a good candidate for the Belliot process of oxidative destruction, as well as liquid injection, rotary kiln, and fluidized bed incineration. 4-Xylene may be sent to a solvent disposal company, but prior to implementing any land disposal of waste residue (including waste sludge), consult regulatory agencies for guidance.

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

First Aid · 2 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageFireproof. Store only in original container. Separated from strong oxidants and strong acids. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 2 items

Biological Exposure Indices (BEI) [ACGIH] - Xylenes (technical or commercial grades): 0.3 g/g creatine methylhippuric acids in urine at end of shift; [ACGIH TLVs and BEIs]

100.0 [ppm]

Fire Fighting Procedures · 4 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

Foam, dry chemical or carbon dioxide. Water may be ineffective. Cool exposed containers with water.

Toxicology

Body Burden · 3 items

4-Xylene was detected in expired breath samples of residents in Bayonne, NJ (3.0-3.2 ug/cu m), Los Angeles, CA (1.4-2.3 ug/cu m), and Pittsburgh, PA (1.1 ug/cu m)(1). 4-Xylene was detected in expired breath samples in Los Angeles, CA (2.43-3.46 ug/cu m)(2). Combined 3-/4-xylene was detected in expired breath samples in Bayonne, NJ at average concentrations of 4.7-10 ug/cu m(3). Based on a sample of 355 persons, it was determined that 95% of the population of Bayonne and Elizabeth, NJ had detectable levels of combined 3-/4-xylene in expired breath(4).

The mean concentration of 3-/4-xylene was 0.21 ng/mL in the blood of 134 school-age children that participated in the School Health Initiative: Environment, Learning, Disease (SHIELD) study in Minneapolis, MN(1). The mean concentration of 3-/4-xylene was 0.32 ng/mL in the blood of 43 children living in an inner city neighborhood of Minneapolis, MN(2).

The reported mean concentration of 3-/4-xylene measured in the personal air of 36 high school students in New York City participating in the TEACH study was 10.9 ug/cu m in the summer and 6.71 ug/cu m in the winter(1). A median measured personal 3-/4-xylene concentration of 4.4 ug/cu m was determined for participants of the BEAM study which included 55 individuals employed in non-manufacturing workplaces, including schools and offices, and living in suburban or urban locations in the greater Boston, MA area(2).

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 5 items

Sixteen men were studied in an exposure chamber to assess the effect of four hr exposure to toluene (3.25 mmol/cu m), p-xylene (2.84 mmol/cu m) a mixture of toluene and p-xylene (2.20 + 0.94 mmol/cu m) and a control condition. With the aid of microcomputers subjects performed tests of simple reaction time, short term memory, and choice reaction time immediately after entering the chamber, after two, and after four hours of exposure. The results indicate that the performance on the tests was unaffected by exposure. In the light of this result, the risk of an acute effect on central nervous functions after exposure for four hours at these concn was considered to be minimal.

Eight male subjects were experimentally exposed to toluene, p-xylene, and a combination of toluene and p-xylene to study the influence of coexposure and exposure to different levels of each solvent on their uptake and elimination. The exposures were performed for 4 hr at exposure levels equivalent to or lower than the Swedish threshold limit value for toluene, 300 mg/cu m (3.2 mmol/cu m). During and after the exposure, solvent concentrations were measured in blood and in expired air. In addition, the pulmonary ventilation rate was measured during the exposure. Decreases in the blood/end exhaled air concentration ratio were found for both toluene and p-xylene when given in combination compared with separate exposure. The total solvent uptake relative to the exposure level was decreased after exposure to the higher solvent concentration, and the apparent clearance was also decreased after exposure to the higher concentration of solvent. Finally, the blood solvent concentration were lower at the end of the exposure compared with the maximal concentration during each exposure condition. In the kinetics of toluene and p-xylene, the total amount of toluene or p-xylene, or both, seems to be of major importance. The change in blood/end exhaled air concentration ratio may indicate an effect of coexposure.

It is unclear whether the pneumotoxicity observed with bromobenzene in phenobarbital-induced rats is related to bromobenzene bioactivation in lung, liver or both. To help differentiate pulmonary from hepatic bioactivation, bromobenzene was admin alone and in combination with p-xylene, which inhibits pulmonary but induces hepatic cytochrome P450. Exposure to p-xylene alone (3400 ppm for 4 hr) produced no changes in bronchoalveolar lavage fluid measurements ... or serum sorbitol dehydrogenase. p-Xylene incr hepatic microsomal benzyloxy-, pentoxy-, and ethoxy-resorufin O-dealkylase activities but decr pulmonary microsomal benzyloxy- and pentoxy-resorufin O-dealkylase activities. Immunoblot analysis revealed an induction of hepatic but not pulmonary microsomal P450IIB apoprotein. When rats were exposed to p-xylene (2800 ppm) or room air for 4 hr, treated 12 hr later with bromobenzene (0.5 mL/kg, ip) or corn oil, and killed after 12 hr, p-xylene incr hepatic P450IIB (27-fold) concomitant with a similar incr in benzyloxy-resorufin O-dealkylase activity. p-Xylene also incr hepatic P450IA apoprotein (3 to 4-fold) with a complimentary incr in ethoxy-resorufin O-dealkylase activity. p-Xylene potentiated bromobenzene-induced hepatotoxicity. In pulmonary microsomes p-xylene and bromobenzene each produced similar decr in both ethoxy- and benzyloxy-resorufin O-dealkylase activities. The combination of p-xylene and bromobenzene had an additive effect on pulmonary P450IA1 reduction. Bronchoalveolar lavage fluid analysis and histopathology revealed no pneumotoxicity with any treatment. p-Xylene potentiation of bromobenzene-induced hepatotoxicity without pneumotoxicity suggests that the liver does not produced metabolites of bromobenzene which are directly involved in pulmonary damage.

The effects of p-xylene and ethanol on the lung metabolism of benzo(a)pyrene were studied. p-Xylene was admin by ip injection at doses ranging from 0.1 to 1.0 g/kg (1:1 in soybean oil). Ethanol was admin po at 5 g/kg (40% w/v). Rats given p-xylene, ethanol, or p-xylene and ethanol were sacrificed 1 hr after treatment. Additional time points of 15 min, 30 min, 4 hr, and 24 hr after p-xylene (1 g/kg) were examined. 3-Hydroxy-benzo(a)pyrene (3-OH) formation was measured fluorometrically as aryl hydrocarbon hydroxylase activity in lung microsomes. p-Xylene (1 g/kg) inhibited the formation of 3-OH benzo(a)pyrene 40% at 15 min, 27% at 30 min, 43% at 1 hr, and 39% at 4 hr after treatment. Inhibition of aryl hydrocarbon hydroxylase activity was still present 24 hr after dosing (41%). Aryl hydrocarbon hydroxylase activity was inhibited 27% and 46% at 0.5 mg/kg and 1.0 mg/kg p-xylene (1 hr), respectively, while the lowest dose (0.1 mg/kg) did not change activity. Analysis of the major metabolites of benzo(a)pyrene by HPLC demonstrated that the formation of 3-OH and 4,5-diol benzo(a)pyrene were inhibited 32% and 50%, respectively, in lung microsomes prepared 24 hr after a single injection of p-xylene (1 g/kg). None of the other metabolites analyzed were changed by p-xylene. Ethanol had no effect on 3-OH benzo(a)pyrene formation during a 1-hr treatment. A combined dose of ethanol and p-xylene moderately inhibited 3-OH benzo(a)pyrene formation. These findings indicate that benzo(a)pyrene detoxication (i.e., 3-OH formation) in rat lung is selectively inhibited by p-xylene but not ethanol. Ethanol appears to modify the inhibitory effect of p-xylene.

For more Interactions (Complete) data for 4-XYLENE (6 total), please visit the HSDB record page.

Target OrgansEyes, skin, respiratory system, central nervous system, gastrointestinal tract, blood, liver, kidneys
Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Ecotoxicity Values · 5 items

LC100; Species: Tetrahymena pyriformis (Ciliate); Concentration: 3.77 mmole/L for 24 hr /Conditions of bioassay not specified/

LC50; Species: Crangon franciscorum (Shrimp); Concentration: 2.0 ppm for 96 hr /Conditions of bioassay not specified/

EC50; Species: Chlamydomonas angulosa (Green algae) age 72-96 hr exponential growth phase, 5X10+4 cells/mL; Conditions: static, 19 °C, pH 6.5; Concentration: 430 mmol/cu m for 3 hr; Effect: physiology, photosynthesis /formulated product/

EC50; Species: Chlorella vulgaris (Green algae) age 3-4 days exponential growth phase, 20X10+4 cells/mL; Conditions: static, 19 °C, pH 6.5; Concentration: 990 mmol/cu m for 3 hr; Effect: physiology, photosynthesis /formulated product/

For more Ecotoxicity Values (Complete) data for 4-XYLENE (16 total), please visit the HSDB record page.

Regulatory information

RCRA Requirements · 2 items

F003; When xylene is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F003), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations. /Xylenes/.

U239; As stipulated in 40 CFR 261.33, when xylene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /Xylenes/

TSCA Requirements · 2 items

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. p-Xylene is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 1/26/94; Reporting date: 3/28/94.

Atmospheric Standards · 2 items

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. p-Xylene is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 4-Xylene is included on this list.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 item

p-Xylene is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

State Drinking Water Standards(CA) CALIFORNIA 1750 ug/L

Safety data

OEB
A
OEL
TWA: 100 ppm (435 mg/m3), STEL: 150 ppm (655 mg/m3)
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
ZE2625000

Chemistry & industry

Pharmacology

Biological Half-LifeElimination half-times from fat were estimated to be 2-7 hr.
Metabolism/Metabolites · 6 items

/When administered to rabbit, rat, and guinea pig/ p-xylene was excreted as p-toluic acid derivative, but a 2,5-dimethylphenol glucuronide was also isolated ... .

Metab of p-xylene (100 umol) studied in isolated, perfused rabbit livers and lungs. Release of p-tolualdehyde into circulation did not occur in perfused rabbit livers. P-toluric acid (n-p-toluylglycine) was major hepatic metabolite, with smaller amt of toluic acid & p-methylbenzyl alcohol. Rabbit livers did not produce detectable amt of p-tolualdehyde, 2,5-dimethylphenol or any glucuronide conjugates. One major pulmonary metab was p-methylbenzyl alc. Predominance of this metab reflects deficiency of lung tissue in alc dehydrogenase. Perfused lung also produced 2,5-dimethylphenol a derivative not produced in the liver. During p-xylene metab in perfused lungs, derivatives which became covalently bound to lung proteins were formed which suggests that p-xylene metab might proceed at least partially through reactive intermediate(s) causing destruction of pulmonary cytochrome P450. Metab was also characterized using reconstituted monooxygenase systems containing purified rabbit pulmonary lung cytochrome P450 (i) & (ii).

The involvement of sequential side-chain oxidn, sulfation, & glutathione conjugation in formation of mercapturic acids from xylenes was investigated. The position of methyl groups attached to the aromatic nucleus affected metabolism. Factors that are involved in high yield of mercapturic acids after admin of o-xylene as compared to m-xylene & p-xylene incl relatively low apparent affinity of o-methylbenzyl alcohol for cytosolic alcohol dehydrogenase, the relatively high apparent affinity of o-methylbenzyl alc for cytosolic sulfotransferase, & the high electrophilic reactivity of the o-methylbenzyl sulfate.

Meta & para isomers are ... extensively oxidized to toluic acids (about 90% of the dose), & these are conjugated mostly with glycine. Hydroxylation to corresponding xylenols also occurs to a small extent.

For more Metabolism/Metabolites (Complete) data for 4-XYLENE (14 total), please visit the HSDB record page.

P-xylene has known human metabolites that include 2,5-dimethylphenol and 4-Methylbenzylalcohol.

Absorption, Distribution and Excretion · 5 items

In rats and mice, m- and p-xylene are distributed primarily to lipid-rich tissues, such as fat, blood, and brain and also in organs highly perfused with blood such as kidney and liver. Small amounts of p-xylene and o-xylene cross the placenta and distribute to amnionic fluid and fetal tissue. Oral administration of m-xylene to rats led to distribution of 14C-m-xylene in adipose tissue, approximately 0.3% of dose in female and 0.1% in males.

Humans exposed to 46 or 92 ppm of o-, m-, p-xylene or a mixture (1:1:1) of the three for 8 hr absorbed approx 64% of the inhaled xylene. No difference in the absorption rate was reported due to level of exposure, length of exposure, or the type and/or mixture of the xylene isomers. The absorption of xylene appeared to vary among individuals due to differences in ventilation rate. ... Individuals with an incr ventilation rate retained less xylene.

In rats exposed to 208 mg/cu m methyl-(14)C para-xylene for 1 hour, distribution of radioactivity immediately after termination of the exposure was highest in the kidneys, followed by subcutaneous fat, ischiatic nerve, blood, liver and lungs. Activity was 1/5 to 1/30 of these levels 6 hours after the end of exposure.

Pregnant mice were exposed by inhalation to (14)C para-xylene (theoretical concentration, 2000 ppm (8680 mg/cu m)) for 10 min on days 11, 14 or 17 of gestation, and distribution of the label was determined 0, 0.5, 1 and 4 hours after exposure. The label quickly entered the embryo, but uptake was low relative to maternal tissues. All fetal activity was extractable, indicating that no firmly bound metabolite was present.

For more Absorption, Distribution and Excretion (Complete) data for 4-XYLENE (10 total), please visit the HSDB record page.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 6 items

Permitted for use as an inert ingredient in non-food pesticide products; [EPA] Found in coal tar; Commercial xylene is a mixture of the o-, m-, and p- isomers; Used as a solvent, raw material, catgut sterilant, and in microscopy; [Merck Index] Used predominately to make purified terephthalic acid (PTA) and dimethyl terephthalate (DMT) which are used in polyester production; Also used as a solvent, for paints, in the printing trade, and in the production of di-paraxylene and herbicides; [HSBD]

Painting (Solvents) [Category: Paint]

Synthesis of terephthalic acid for polyester resins and fibers and in the manufacture of vitamins, pharmaceuticals, and insecticides

PX /4-xylene/ is the most important commercial isomer. Almost all of the PX is converted to terephthalic acid and dimethylterephthalate, and then to poly(ethylene terephthalate) for ultimate use in fibers, films, and resins. Miscellaneous uses include as solvent, production of di-paraxylene, and as a herbicide.

p-Xylene ... frequently ... used for paints or in the printing trade.

Used as a chemical intermediate for the synthesis of 1,4-bis(chloromethyl)benzene; dimethyl terephthalate; poly-p-xylylene; terephthalic acid; 4-(tri-fluoromethyl)benzaldehyde; 4-(trifluoromethyl)benzyl alcohol; 2,5-xylidine.

U.S. Exports · 5 items

19.7% of total 1980 xylene market.

(1978) 3.19X10+11 G

(1983) 3.23X10+11 G

(1985) 5.03X10+11 g

For more U.S. Exports (Complete) data for 4-XYLENE (10 total), please visit the HSDB record page.

U.S. Imports · 5 items

(1978) 9.53X10+9 G

(1983) 3.18X10+10 G

(1985) 6.53X10+10 g

(1986) 3.71X10+7 gal

For more U.S. Imports (Complete) data for 4-XYLENE (9 total), please visit the HSDB record page.

U.S. Production · 6 items

2023: 5,500,000,000 - <7,000,000,000 lb

(1976) 1.32x10+12 g

(1977) 1.44X10+12 G

(1980) 1.9X10+12 G

(1981) 2.06x10+12 g

For more U.S. Production (Complete) data for 4-XYLENE (26 total), please visit the HSDB record page.

Consumption Patterns · 5 items

CHEMICAL PROFILE: Paraxylene. Dimethyl terephthalate and terephthalic acid for saturated polyester production, 100% (except negligible amounts used as solvents, coatings or pesticides) (1985)

CHEMICAL PROFILE: Paraxylene. Dimethyl terephthalate and terephthalic acid for saturated polyester production, 100% (except negligible amounts for use as solvents, coating or pesticides). This includes 75% for domestic consumption and 25% for export.

CHEMICAL PROFILE: Paraxylene. US Demand: 1985: 4.5 billion pounds; 1986: 4.7 billion pounds; 1990: 5.23 billion pounds /projected/

CHEMICAL PROFILE: Paraxylene. Dimethyl terephthalate and terephthalic acid, 85%; exports, 15%. (Domestically, negligible amounts are used in solvents, coatings and pesticides).

For more Consumption Patterns (Complete) data for 4-XYLENE (12 total), please visit the HSDB record page.

Consumer UsesNot Known or Reasonably Ascertainable
Applications · 5 items

Descriptionp-xylene is an aromatic hydrocarbon based on benzene with two methyl substituents with the chemical formula C8H10 or C6H4(CH3)2. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The “p” stands for para, identifying that he two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. p-Xylene is a colorless, flammable liquid practically insoluble in water. p-Xylene is a colorless watery liquid with a sweet odor and is dangerously flammable, with a flash point of 27°C. p-Xylene is widely used as a feedstock (or “building block”) to manufacture other industrial chemicals, notably terephthalic acid (TPA), purified terephthalic acid (PTA) and dimethyl-terephthalate (DMT). It also may be polymerised directly to produce parylene.

UsesXylene occurs in petroleum solvents andgasoline. The widest applications of xyleneare as solvents in paints, coatings, and rubber.Xylene isomers are used in the manufacture ofdyes, drugs, pesticides, and in many organicintermediates, such as terephthalic acid andphthalic anhydride.

Usesp-Xylene is used as a precursor in the production of benzoic, isophthalic, tetraphillic acids and dimethyle esters, which are used in the manufacture of polyester. It acts as an intermediate in plastic and rubber products.

UsesAs solvent; raw material for production of benzoic acid, phthalic anhydride, isophthalic and terephthalic acids as well as their dimethyl esters used in the manufacture of polyester fibers; manufacture of dyes and other organics; sterilizing catgut; with Canada balsam as oil-immersion in microscopy; clearing agent in microscope technique.

General DescriptionA colorless watery liquid with a sweet odor. Less dense than water. Insoluble in water. Irritating vapor. Freezing point is 56°F.

Additional notes

DefinitionChEBI: A xylene with methyl groups at positions 1 and 4.

Related reactions

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