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M-Xylene: Difference between revisions

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Revision as of 23:52, 3 December 2010 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits Added CSID, stdInChI, and stdInChIkey← Previous edit Latest revision as of 02:57, 7 November 2024 edit undoBD2412 (talk | contribs)Autopatrolled, IP block exemptions, Administrators2,458,998 editsm Clean up spacing around commas and other punctuation fixes, replaced: ,1999 → , 1999Tag: AWB 
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{{DISPLAYTITLE:''m''-Xylene}} {{DISPLAYTITLE:''m''-Xylene}}
{{chembox {{chembox
|Verifiedfields = changed
| verifiedrevid = 277865671
|Watchedfields = changed
| Name = ''m''-Xylene
|verifiedrevid = 400399538
| ImageFileL1 = Meta-Xylol - meta-xylene 2.svg
|Name = ''m''-Xylene
| ImageNameL1 = Skeletal formula
|ImageFileL1 = Meta-Xylene-2D-structure.svg
| ImageSizeL1 = 100px
|ImageNameL1 = Skeletal formula
| ImageFileR1 = m-xylene-spaceFilling.png
|ImageSizeL1 = 100px
| ImageSizeR1 = 150px
|ImageFileR1 = m-xylene-spaceFilling.png
| ImageNameR1 = Space-filling model
|ImageSizeR1 = 150px
| OtherNames = ''m''-Xylol<br />1,3-Dimethylbenzene
|ImageNameR1 = Space-filling model
| Section1 = {{Chembox Identifiers
|PIN = 1,3-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_Ref = {{cascite}}
|SystematicName = 1,3-Dimethylbenzene
| CASNo = 108-38-3
|OtherNames = ''m''-Xylene,<ref name=iupac2013 /> meta-Xylol <!-- not m-methyltoluene, substitution of toluene by additional methyl groups is not allowed -->
| | PubChem = 7929
|Section1={{Chembox Identifiers
| ChemSpiderID = 7641
|CASNo_Ref = {{cascite|correct|CAS}}
| SMILES = Cc1cccc(c1)C
|CASNo = 108-38-3
| RTECS = ZE2275000
|Beilstein = 605441
| SMILES = CC1=CC(C)=CC=C1
|ChEBI_Ref = {{ebicite|correct|EBI}}
| StdInChI = 1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3
|ChEBI = 28488
| StdInChIKey = IVSZLXZYQVIEFR-UHFFFAOYSA-N
|ChEMBL_Ref = {{ebicite|correct|EBI}}
}}
|ChEMBL = 286727
| Section2 = {{Chembox Properties
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Appearance = Colorless liquid
|ChemSpiderID = 7641
| Formula = C<sub>8</sub>H<sub>10</sub>
|EC_number = 203-576-3
| MolarMass = 106.16 g/mol
|Gmelin = 101390
| BoilingPtC = 139
|KEGG_Ref = {{keggcite|correct|kegg}}
| MeltingPtC = -48
|KEGG = C07208
| Density = 0.86 g/mL
|PubChem = 7929
| RefractIndex = 1.49722
|RTECS = ZE2275000
| Solubility = insoluble
|UNII_Ref = {{fdacite|correct|FDA}}
| Solubility1 = very soluble
|UNII = O9XS864HTE
| Solvent1 = ethanol
|UNNumber = 1307
| Solubility2 = very soluble
|SMILES = Cc1cccc(c1)C
| Solvent2 = diethyl ether
|SMILES1 = CC1=CC(C)=CC=C1
| Viscosity = 0.8059 c] at 0 °C<br>0.6200 c] at 20 °C
|Jmol1 = none
}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| Section7 = {{Chembox Hazards
|StdInChI = 1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3
| ExternalMSDS =
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| FlashPt = 25 °C
|StdInChIKey = IVSZLXZYQVIEFR-UHFFFAOYSA-N
| MainHazards = Harmful or fatal if swallowed. Vapor harmful. Flammable liquid and vapor.
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
| NFPA-O
| RPhrases = {{R10}} {{R20}} {{R21}} {{R38}}
| SPhrases = {{S25}}
}}
| Section8 = {{Chembox Related
| Function = ]
| OtherFunctn = ]<br />]<br />]<br />]
}}
}} }}
|Section2={{Chembox Properties
|Appearance = Colorless liquid
|Formula = C<sub>8</sub>H<sub>10</sub>
|MolarMass = 106.16 g/mol
|BoilingPtC = 139
|MeltingPtC = -48
|Density = 0.86 g/mL
|RefractIndex = 1.49722
|Odor = Aromatic in high concentrations
|Solubility = does not react with water
|Solubility1 = miscible
|Solvent1 = ethanol
|Solubility2 = miscible
|Solvent2 = diethyl ether
|Viscosity = 0.8059 c] at 0 °C<br>0.6200 c] at 20 °C
|Dipole = 0.33-0.37 ]<ref name="Lange´s">DeanHandb, Lange´s Handbook of chemistry, 15th edition, 1999.</ref>
|VaporPressure = 9 mmHg (20°C)<ref name=PGCH/>
|MagSus = -76.56·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Hazards
|ExternalSDS =
|FlashPtC = 27
|FlashPt_ref = <ref name=ICSC/>
|MainHazards = Harmful if swallowed. Vapor harmful. Flammable liquid and vapor.
|NFPA-H = 1
|NFPA-F = 3
|NFPA-R = 0
|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|226|302|304|312|315|318|332}}
|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|301+310|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|331|332+313|362|363|370+378|403+235|405|501}}
|PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0669}}</ref>
|ExploLimits = 1.1%-7.0%<ref name=PGCH/>
|IDLH = 900 ppm<ref name=PGCH/>
|REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<ref name=PGCH/>
|AutoignitionPtC = 527
|AutoignitionPt_ref =<ref name=ICSC>{{cite web |url = https://www.cdc.gov/niosh/ipcsneng/neng0085.html |title = m-Xylene |work = International Chemical Safety Cards |publisher = IPCS/NIOSH |date = July 1, 2014 |access-date = September 9, 2017 |archive-url = https://web.archive.org/web/20171205042535/https://www.cdc.gov/niosh/ipcsneng/neng0085.html |archive-date = December 5, 2017 |url-status = dead }}</ref>
|TLV-TWA = 100 ppm<ref name=ICSC/>
|TLV-STEL = 150 ppm<ref name=ICSC/>
|LCLo = 2010 ppm (mouse, 24 hr)<br/>8000 ppm (rat, 4 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref>
}}
|Section4={{Chembox Related
|OtherFunction_label = ]
|OtherFunction = ]<br />]<br />]<br />]
}}
}}
'''''m''-Xylene''' (''']-xylene''') is an ]. It is one of the three ]s of ] known collectively as ]s. The ''m-'' stands for ''meta-'', indicating that the two methyl groups in ''m''-xylene occupy positions 1 and 3 on a benzene ring. 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.<ref name="Ullmann">{{Ullmann|author1=Fabri, Jörg |author2=Graeser, Ulrich|author3= Simo, Thomas A.|title=Xylenes|year=2000|doi=10.1002/14356007.a28_433}}</ref>


==Production and use==
'''''m''-Xylene''' is an ] ], based on ] with two ] ]s.
] contains about 1 weight percent xylenes.<ref>EPA-454/R-93-048
Emission Inventory Branch Technical Support Division Office of Air Quality Planning and Standards ]
March 1994</ref> The ''meta'' isomer can be isolated from a mix of xylenes by the partial sulfonation (to which other isomers are less prone) followed by removal of unsulfonated oils and ] of the sulfonated product.


The major use of ''meta''-xylene is in the production of ], which is used as a ]izing ] to alter the properties of ]. The conversion ''m''-xylene to isophthalic acid entails ] ]. ''meta''-Xylene is also used as a raw material in the manufacture of 2,4- and 2,6-] as well as a range of smaller-volume chemicals.<ref>Ashford's Dictionary of Industrial Chemicals, third edition, page 9692.</ref><ref name="Ullmann"/> ] gives ].
It is an isomer of ] and ]. The ''m'' stands for '']'', meaning the two methyl substituents are at ]s 1 and 3 on the aromatic ring.


==Toxicity and exposure==
The major chemical use of metaxylene is in the manufacture of ], which is used as a ] to alter the properties of ] (PET) making PET more suitable for the manufacture of soft drinks bottles.
Xylenes are not acutely toxic, for example the {{LD50}} (rat, oral) is 4300&nbsp;mg/kg. Effects vary with animal and xylene isomer. Concerns with xylenes focus on narcotic effects.<ref name="Ullmann"/>

==See also==
*]


==References== ==References==
{{Unreferenced|date =September 2007}}
<references/> <references/>

{{Hydrocarbons}}


{{DEFAULTSORT:Xylene, m-}} {{DEFAULTSORT:Xylene, m-}}
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M-Xylene: Difference between revisions Add topic