| Revision as of 08:52, 25 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikip← Previous edit | Latest revision as of 16:38, 22 April 2023 edit undoM97uzivatel (talk | contribs)Extended confirmed users6,577 editsNo edit summary | ||
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| {{DISPLAYTITLE:''p''-Xylene}} | {{DISPLAYTITLE:''p''-Xylene}} | ||
| {{chembox | {{chembox | ||
| | |
|Verifiedfields = changed | ||
| |Watchedfields = changed | |||
| | verifiedrevid = 390143220 | |||
| |verifiedrevid = 415835068 | |||
| | Name = ''p''-Xylene | |||
| | |
|Name = ''p''-Xylene | ||
| |ImageFile = Para-Xylol - para-xylene.svg | |||
| | ImageName = Skeletal formula | |||
| |ImageName = Skeletal formula | |||
| | ImageSize = 160px | |||
| |ImageCaption = ] | |||
| | ImageFile1 = p-xylene-spaceFilling.png | |||
| |ImageSize = 180px | |||
| | ImageSize1 = 150px | |||
| |ImageFile1 = p-xylene-spaceFilling.png | |||
| | ImageName1 = Space-filling model | |||
| |ImageSize1 = 150px | |||
| | OtherNames = ''p''-Xylol<br />1,4-Dimethylbenzene | |||
| |ImageName1 = Space-filling model | |||
| | Section1 = {{Chembox Identifiers | |||
| |ImageCaption1 = Space-filling model | |||
| | CASNo_Ref = {{cascite|correct|CAS}} | |||
| |PIN = 1,4-Xylene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 139 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4}}</ref> | |||
| | CASNo = 106-42-3 | |||
| |SystematicName = 1,4-dimethylbenzene | |||
| | RTECS = ZE2625000 | |||
| |OtherNames = ''p''-Xylene, ''p''-dimethylbenzene; ''p''-xylol; 1,4-xylene; ''p''-methyltoluene;<ref>Not to be used</ref> paraxylene; chromar; scintillar; 4-methyltoluene;<ref>Archaic name</ref> NSC 72419; or 1,4-dimethylbenzene.<ref name=NIST>{{cite web|title=p-xylene|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C106423&Mask=200|publisher=NIST|access-date=21 February 2013}}</ref> | |||
| | KEGG_Ref = {{keggcite|changed|kegg}} | |||
| |Section1 = {{Chembox Identifiers | |||
| | KEGG = C06756 | |||
| |CASNo_Ref = {{cascite|correct|CAS}} | |||
| | SMILES = CC1=CC=C(C)C=C1 | |||
| |CASNo = 106-42-3 | |||
| }} | |||
| |Beilstein = 1901563 | |||
| | Section2 = {{Chembox Properties | |||
| |ChEBI_Ref = {{ebicite|correct|EBI}} | |||
| | Appearance = Colorless liquid<br>colorless crystalline solid | |||
| |ChEBI = 27417 | |||
| | Formula = C<sub>8</sub>H<sub>10</sub> | |||
| |ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| | MolarMass = 106.16 g/mol | |||
| |ChEMBL = 31561 | |||
| | BoilingPtC = 138.35 | |||
| |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | MeltingPtC = 13.2 | |||
| |ChemSpiderID = 7521 | |||
| | Density = 0.861 g/mL | |||
| |EINECS = 203-396-5 | |||
| | RefractIndex = 1.49582 | |||
| |Gmelin = 2697 | |||
| | Solubility = insoluble | |||
| |KEGG_Ref = {{keggcite|correct|kegg}} | |||
| | Solubility1 = very soluble | |||
| |KEGG = C06756 | |||
| | Solvent1 = ethanol | |||
| |PubChem = 7809 | |||
| | Solubility2 = very soluble | |||
| |RTECS = ZE2625000 | |||
| | Solvent2 = diethyl ether | |||
| |UNII_Ref = {{fdacite|correct|FDA}} | |||
| | Viscosity = 0.7385 c] at 0 °C<br>0.6475 c] at 20 °C | |||
| |UNII = 6WAC1O477V | |||
| | Dipole = 0.07 ] | |||
| |SMILES = CC1=CC=C(C)C=C1 | |||
| }} | |||
| |InChI = 1/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3 | |||
| | Section7 = {{Chembox Hazards | |||
| |InChIKey = URLKBWYHVLBVBO-UHFFFAOYAE | |||
| | ExternalMSDS = | |||
| |StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| | FlashPt = 25 °C | |||
| |StdInChI = 1S/C8H10/c1-7-3-5-8(2)6-4-7/h3-6H,1-2H3 | |||
| | MainHazards = Harmful or fatal if swallowed. Vapor harmful. Flammable liquid and vapor. | |||
| |StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| | NFPA-H = 2 | |||
| |StdInChIKey = URLKBWYHVLBVBO-UHFFFAOYSA-N | |||
| | NFPA-F = 3 | |||
| }} | |||
| | NFPA-R = 0 | |||
| |Section2 = {{Chembox Properties | |||
| | NFPA-O | |||
| |Appearance = Colorless liquid | |||
| | RPhrases = {{R10}} {{R20}} {{R21}} {{R36}} {{R38}} | |||
| |C=8 | H=10 | |||
| | SPhrases = {{S25}} | |||
| |BoilingPtC = 138.35 | |||
| }} | |||
| |Odor = Aromatic<ref name=PGCH/> | |||
| | Section8 = {{Chembox Related | |||
| |MeltingPtC = 13.2 | |||
| | Function = ] | |||
| |Density = 0.861 g/mL | |||
| | OtherFunctn = ]<br />]<br />]<br />] | |||
| |RefractIndex = 1.49582 | |||
| }} | |||
| |Solubility = Insoluble | |||
| |Solubility1 = Very soluble | |||
| |Solvent1 = ethanol | |||
| |Solubility2 = Very soluble | |||
| |Solvent2 = diethyl ether | |||
| |Viscosity = 0.7385 c] at 0 °C<br>0.6475 c] at 20 °C | |||
| |Dipole = 0.00 ]<ref>Perry's Handbook of Chemical Engineers</ref> | |||
| |VaporPressure = 9 mmHg (20°C)<ref name=PGCH/> | |||
| |MagSus = -76.78·10<sup>−6</sup> cm<sup>3</sup>/mol | |||
| }} | |||
| |Section3 = {{Chembox Hazards | |||
| |ExternalSDS = | |||
| |FlashPtC = 27 | |||
| |FlashPt_ref = <ref name=ICSC/> | |||
| |MainHazards = Harmful or if swallowed. Vapor maybe toxic.<ref>P-Xylene: main hazards</ref> Flammable liquid and vapor. | |||
| |NFPA-H = 2 | |||
| |NFPA-F = 3 | |||
| |NFPA-R = 0 | |||
| |GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} | |||
| |GHSSignalWord = Danger | |||
| |HPhrases = {{H-phrases|226|302|304|312|315|319|332|335|412}} | |||
| |PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|301+310|302+352|303+361+353|304+312|304+340|305+351+338|312|321|322|331|332+313|337+313|362|363|370+378|403+233|403+235|405|501}} | |||
| |PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0670}}</ref> | |||
| |ExploLimits = 1.1%-7.0%<ref name=PGCH/> | |||
| |LC50 = 4550 ppm (rat, 4 hr)<ref name=IDLH>{{IDLH|95476|Xylenes}}</ref> | |||
| |REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<ref name=PGCH/> | |||
| |TLV-TWA = 100 ppm<ref name=ICSC>{{cite web |url = https://www.cdc.gov/niosh/ipcsneng/neng0086.html |title = p-Xylene |work = International Chemical Safety Cards |publisher = ICSC/NIOSH |date = July 1, 2014}}</ref> | |||
| |TLV-STEL = 150 ppm<ref name=ICSC/> | |||
| |IDLH = 900 ppm<ref name=PGCH/> | |||
| |AutoignitionPtC = 528 | |||
| |AutoignitionPt_ref = <ref name=ICSC/> | |||
| |LD50 = 4300 mg/kg<ref>P-Xylene: toxicity for rats</ref> | |||
| |LCLo = 3401 ppm (mouse)<ref name=IDLH/> | |||
| }} | |||
| |Section4 = {{Chembox Related | |||
| |OtherFunction_label = ] | |||
| |OtherFunction = ]<br />]<br />]<br />] | |||
| }} | |||
| }} | }} | ||
| '''''p''-Xylene''' is an ], based on ] with two ] ]s. The “p” stands for ''para'', identifying the location of the methyl groups as across from one another. | |||
| '''''p''-Xylene''' (''']-xylene''') is an ]. It is one of the three ]s of ] known collectively as ]s. 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 ], that it differs from the other isomers, ] and ]. All have the same chemical formula C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub>. All xylene isomers are colorless and highly flammable. The odor threshold of ''p''-xylene is 0.62 ] (ppm).<ref name=MSDS>{{cite web|title=p-Xylene MSDS|publisher=ScienceLab.com}}</ref> | |||
| It is an isomer of ]. Other isomers include ] and ]. | |||
| ''p''-Xylene is used on a large scale for the manufacture of ] for ]. Its ] is known as ]. | |||
| ==Production== | |||
| ''p''-Xylene is produced by ] of naptha (petroleum derivative) and separated in a series of distillation, adsorption or crystallization and reaction processes from ''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. | |||
| The production of ''p''-xylene is industrially significant, with annual demand estimated at 37 million tons in 2014, and still on the increase.<ref name="Ullmann">{{cite book |url= |title=Ullmann's Encyclopedia of Industrial Chemistry |last1=Fabri |first1=Jörg |last2=Graeser |first2=Ulrich |last3=Simo |first3=Thomas A. |publisher=Wiley Online Library |year=2000 |doi=10.1002/14356007 |isbn=9783527303854 }}</ref><ref>Nature 532,435–437 (28 April 2016) doi:10.1038/532435a</ref> ''p''-Xylene is produced by ] of petroleum ] as part of the ] 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 ]. Its melting point is the highest among this series of isomers, but simple crystallization does not allow easy purification due to the formation of ] 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.<ref>{{cite journal|journal=Science|year=2016|volume=353|issue=6301|pages=804–7|doi=10.1126/science.aaf1343|pmid=27540170|title=Reverse osmosis molecular differentiation of organic liquids using carbon molecular sieve membrane|author1=Koh, D. Y.|author2=McCool, B. A.|author3=Deckman, H. W.|author4=Lively, R. P.|bibcode=2016Sci...353..804K|s2cid=9480478}}</ref> | |||
| ==Industrial applications== | |||
| ''p''-Xylene is an important chemical ]. Among other industrial applications, it is a raw material in the large scale synthesis of various ]s. In particular it is a component in the production of ] for ]s such as ] (generally known as PET). It also may be polymerised directly to produce ]. | |||
| :] | |||
| ==Toxicity and exposure== | |||
| Xylenes are not acutely toxic, for example the ] (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.<ref name=properties>{{cite web|title=Material Safety Data Sheet – Para-Xylene|url=http://siri.org/msds/mf/amoco/files/01263000.html|publisher=Amoco|access-date=13 February 2013|archive-url=https://web.archive.org/web/20160304000856/http://siri.org/msds/mf/amoco/files/01263000.html|archive-date=4 March 2016|url-status=dead}}</ref> | |||
| ''p''-Xylene occurs naturally in petroleum and coal tar. It is emitted by most combustion sources, including automobile exhaust and ].<ref>EPA-454/R-93-048 | |||
| Emission Inventory Branch Technical Support Division Office of Air Quality Planning and Standards ] | |||
| March 1994</ref> | |||
| ===Inhalation=== | |||
| 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.<ref name="Exposure">{{cite web|url=https://www.cdc.gov/niosh/ipcsneng/neng0086.html|title=para-Xylene|publisher=National Institute for Occupational Safety and Health|access-date=12 February 2013}}</ref> | |||
| ===Skin=== | |||
| 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.<ref name=Exposure/> | |||
| ===Eyes=== | |||
| 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.<ref name=Exposure/> | |||
| ===Ingestion=== | |||
| 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.<ref name=Exposure/> | |||
| ===Short-term exposure=== | |||
| ''p''-Xylene can cause issues with the central nervous system and if swallowed could cause chemical pneumonitis when breathed into the lungs.<ref name=Exposure /> | |||
| ===Long-term exposure=== | |||
| 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 ]. Exposure can enhance hearing loss caused by noise exposure. Animal tests suggest that this substance could cause damage to human development and reproductive systems.<ref name=Exposure /> | |||
| ==References== | ==References== | ||
| {{reflist}} | |||
| {{Unreferenced|date =March 2008}} | |||
| <references/> | |||
| ==External links== | ==External links== | ||
| Line 65: | Line 136: | ||
| {{DEFAULTSORT:Xylene, p-}} | {{DEFAULTSORT:Xylene, p-}} | ||
| {{Hydrocarbons}} | |||
| ] | |||
| {{hydrocarbon-stub}} | |||
| ] | |||
| ] | |||
| ] | ] | ||
| ] | |||
| ] | |||
Latest revision as of 16:38, 22 April 2023
 Skeletal formula | |
 Space-filling model | |
| Names | |
|---|---|
| Preferred IUPAC name 1,4-Xylene | |
| Systematic IUPAC name 1,4-dimethylbenzene | |
| Other names p-Xylene, p-dimethylbenzene; p-xylol; 1,4-xylene; p-methyltoluene; paraxylene; chromar; scintillar; 4-methyltoluene; NSC 72419; or 1,4-dimethylbenzene. | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Beilstein Reference | 1901563 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.088 
|
| EC Number |
|
| Gmelin Reference | 2697 |
| KEGG | |
| PubChem CID | |
| RTECS number |
|
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C8H10 |
| Molar mass | 106.168 g·mol |
| Appearance | Colorless liquid |
| Odor | Aromatic |
| 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) |
| Solubility in water | Insoluble |
| Solubility in ethanol | Very soluble |
| Solubility in diethyl ether | Very soluble |
| Vapor pressure | 9 mmHg (20°C) |
| Magnetic susceptibility (χ) | -76.78·10 cm/mol |
| Refractive index (nD) | 1.49582 |
| Viscosity | 0.7385 cP at 0 °C 0.6475 cP at 20 °C |
| Dipole moment | 0.00 D |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
| Main hazards | Harmful or if swallowed. Vapor maybe toxic. Flammable liquid and vapor. |
| GHS labelling: | |
| Pictograms |   
|
| Signal word | Danger |
| Hazard statements | H226, H302, H304, H312, H315, H319, H332, H335, H412 |
| Precautionary statements | 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) |
| Autoignition temperature |
528 °C (982 °F; 801 K) |
| Explosive limits | 1.1%-7.0% |
| Threshold limit value (TLV) | 100 ppm (TWA), 150 ppm (STEL) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (median dose) | 4300 mg/kg |
| LC50 (median concentration) | 4550 ppm (rat, 4 hr) |
| LCLo (lowest published) | 3401 ppm (mouse) |
| NIOSH (US health exposure limits): | |
| PEL (Permissible) | TWA 100 ppm (435 mg/m) |
| REL (Recommended) | TWA 100 ppm (435 mg/m) ST 150 ppm (655 mg/m) |
| IDLH (Immediate danger) | 900 ppm |
| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
| |
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).
Production
The production of p-xylene is industrially significant, with annual demand estimated at 37 million tons in 2014, and still on the increase. 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.
Industrial applications
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.
Toxicity and exposure
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.
p-Xylene occurs naturally in petroleum and coal tar. It is emitted by most combustion sources, including automobile exhaust and tobacco smoke.
Inhalation
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.
Skin
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.
Eyes
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.
Ingestion
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.
Short-term exposure
p-Xylene can cause issues with the central nervous system and if swallowed could cause chemical pneumonitis when breathed into the lungs.
Long-term exposure
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.
References
- Not to be used
- Archaic name
- "p-xylene". NIST. Retrieved 21 February 2013.
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 139. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ NIOSH Pocket Guide to Chemical Hazards. "#0670". National Institute for Occupational Safety and Health (NIOSH).
- Perry's Handbook of Chemical Engineers
- P-Xylene: main hazards
- ^ "p-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.
- P-Xylene: toxicity for rats
- ^ "Xylenes". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- "p-Xylene MSDS". ScienceLab.com.
{{cite web}}: Missing or empty|url=(help) - Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). Ullmann's Encyclopedia of Industrial Chemistry. Wiley Online Library. doi:10.1002/14356007. ISBN 9783527303854.
- Nature 532,435–437 (28 April 2016) doi:10.1038/532435a
- Koh, D. Y.; McCool, B. A.; Deckman, H. W.; Lively, R. P. (2016). "Reverse osmosis molecular differentiation of organic liquids using carbon molecular sieve membrane". Science. 353 (6301): 804–7. Bibcode:2016Sci...353..804K. doi:10.1126/science.aaf1343. PMID 27540170. S2CID 9480478.
- "Material Safety Data Sheet – Para-Xylene". Amoco. Archived from the original on 4 March 2016. Retrieved 13 February 2013.
- EPA-454/R-93-048 Locating and estimating air emissions from sources of xylene Emission Inventory Branch Technical Support Division Office of Air Quality Planning and Standards U.S. Environmental Protection Agency March 1994
- ^ "para-Xylene". National Institute for Occupational Safety and Health. Retrieved 12 February 2013.
External links
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