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{{DISPLAYTITLE:''m''-Xylene}} |
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{{DISPLAYTITLE:''m''-Xylene}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 277865671 |
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|Watchedfields = changed |
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| Name = ''m''-Xylene |
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|verifiedrevid = 400399538 |
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| ImageFileL1 = Meta-Xylol - meta-xylene 2.svg |
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|Name = ''m''-Xylene |
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| ImageNameL1 = Skeletal formula |
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|ImageFileL1 = Meta-Xylene-2D-structure.svg |
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| ImageSizeL1 = 100px |
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|ImageNameL1 = Skeletal formula |
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| ImageFileR1 = m-xylene-spaceFilling.png |
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|ImageSizeL1 = 100px |
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| ImageSizeR1 = 150px |
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|ImageFileR1 = m-xylene-spaceFilling.png |
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| ImageNameR1 = Space-filling model |
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|ImageSizeR1 = 150px |
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| OtherNames = ''m''-Xylol<br />1,3-Dimethylbenzene |
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|ImageNameR1 = Space-filling model |
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| Section1 = {{Chembox Identifiers |
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|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> |
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| CASNo_Ref = {{cascite}} |
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|SystematicName = 1,3-Dimethylbenzene |
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| CASNo = 108-38-3 |
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|OtherNames = ''m''-Xylene,<ref name=iupac2013 /> meta-Xylol <!-- not m-methyltoluene, substitution of toluene by additional methyl groups is not allowed --> |
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| | PubChem = 7929 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 7641 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = Cc1cccc(c1)C |
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|CASNo = 108-38-3 |
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| RTECS = ZE2275000 |
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|Beilstein = 605441 |
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| SMILES = CC1=CC(C)=CC=C1 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| StdInChI = 1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3 |
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|ChEBI = 28488 |
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| StdInChIKey = IVSZLXZYQVIEFR-UHFFFAOYSA-N |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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}} |
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|ChEMBL = 286727 |
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| Section2 = {{Chembox Properties |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance = Colorless liquid |
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|ChemSpiderID = 7641 |
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| Formula = C<sub>8</sub>H<sub>10</sub> |
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|EC_number = 203-576-3 |
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| MolarMass = 106.16 g/mol |
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|Gmelin = 101390 |
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| BoilingPtC = 139 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| MeltingPtC = -48 |
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|KEGG = C07208 |
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| Density = 0.86 g/mL |
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|PubChem = 7929 |
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| RefractIndex = 1.49722 |
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|RTECS = ZE2275000 |
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| Solubility = insoluble |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Solubility1 = very soluble |
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|UNII = O9XS864HTE |
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| Solvent1 = ethanol |
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|UNNumber = 1307 |
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| Solubility2 = very soluble |
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|SMILES = Cc1cccc(c1)C |
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| Solvent2 = diethyl ether |
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|SMILES1 = CC1=CC(C)=CC=C1 |
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| Viscosity = 0.8059 c] at 0 °C<br>0.6200 c] at 20 °C |
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|Jmol1 = none |
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}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Section7 = {{Chembox Hazards |
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|StdInChI = 1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3 |
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| ExternalMSDS = |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| FlashPt = 25 °C |
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|StdInChIKey = IVSZLXZYQVIEFR-UHFFFAOYSA-N |
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| MainHazards = Harmful or fatal if swallowed. Vapor harmful. Flammable liquid and vapor. |
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| NFPA-H = 1 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| NFPA-O |
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| RPhrases = {{R10}} {{R20}} {{R21}} {{R38}} |
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| SPhrases = {{S25}} |
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}} |
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| Section8 = {{Chembox Related |
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| Function = ] |
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| OtherFunctn = ]<br />]<br />]<br />] |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Appearance = Colorless liquid |
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|Formula = C<sub>8</sub>H<sub>10</sub> |
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|MolarMass = 106.16 g/mol |
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|BoilingPtC = 139 |
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|MeltingPtC = -48 |
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|Density = 0.86 g/mL |
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|RefractIndex = 1.49722 |
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|Odor = Aromatic in high concentrations |
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|Solubility = does not react with water |
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|Solubility1 = miscible |
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|Solvent1 = ethanol |
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|Solubility2 = miscible |
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|Solvent2 = diethyl ether |
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|Viscosity = 0.8059 c] at 0 °C<br>0.6200 c] at 20 °C |
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|Dipole = 0.33-0.37 ]<ref name="Lange´s">DeanHandb, Lange´s Handbook of chemistry, 15th edition, 1999.</ref> |
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|VaporPressure = 9 mmHg (20°C)<ref name=PGCH/> |
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|MagSus = -76.56·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Hazards |
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|ExternalSDS = |
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|FlashPtC = 27 |
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|FlashPt_ref = <ref name=ICSC/> |
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|MainHazards = Harmful if swallowed. Vapor harmful. Flammable liquid and vapor. |
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|NFPA-H = 1 |
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|NFPA-F = 3 |
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|NFPA-R = 0 |
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|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|302|304|312|315|318|332}} |
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|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}} |
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|PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0669}}</ref> |
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|ExploLimits = 1.1%-7.0%<ref name=PGCH/> |
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|IDLH = 900 ppm<ref name=PGCH/> |
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|REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<ref name=PGCH/> |
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|AutoignitionPtC = 527 |
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|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> |
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|TLV-TWA = 100 ppm<ref name=ICSC/> |
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|TLV-STEL = 150 ppm<ref name=ICSC/> |
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|LCLo = 2010 ppm (mouse, 24 hr)<br/>8000 ppm (rat, 4 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref> |
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}} |
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|Section4={{Chembox Related |
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|OtherFunction_label = ] |
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|OtherFunction = ]<br />]<br />]<br />] |
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}} |
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}} |
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'''''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> |
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==Production and use== |
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'''''m''-Xylene''' is an ] ], based on ] with two ] ]s. |
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] contains about 1 weight percent xylenes.<ref>EPA-454/R-93-048 |
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Emission Inventory Branch Technical Support Division Office of Air Quality Planning and Standards ] |
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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. |
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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 ]. |
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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. |
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==Toxicity and exposure== |
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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. |
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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.<ref name="Ullmann"/> |
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==See also== |
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*] |
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==References== |
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==References== |
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{{Unreferenced|date =September 2007}} |
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<references/> |
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<references/> |
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{{Hydrocarbons}} |
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{{DEFAULTSORT:Xylene, m-}} |
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{{DEFAULTSORT:Xylene, m-}} |
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