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Revision as of 16:11, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 458715441 of page 1,2-Dichloroethene for the Chem/Drugbox validation project (updated: '').  Latest revision as of 10:26, 15 June 2024 edit Renamed user 1e23409a06e0b7922c2dfc98dde51974 (talk | contribs)Extended confirmed users1,813 edits They definitely don't have 4 hydrogensTags: Mobile edit Mobile web edit Advanced mobile edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 443901242
| Watchedfields = changed
| Name = ''cis''-1,2-Dichloroethene (Z) <small>(left)</small> and ''trans''-1,2-Dichloroethene (E) <small>(right)</small>
| verifiedrevid = 477203654
| ImageFileL1 = Cis-1,2-dichloroethene.png | ImageFileL1 = Cis-1,2-dichloroethene.png
| ImageSizeL1 = 110px
| ImageNameL1 = Skeletal formula of cis-1,2-dichloroethene | ImageNameL1 = Skeletal formula of cis-1,2-dichloroethene
| ImageFileR1 = Trans-1,2-dichloroethene.png | ImageFileR1 = Trans-1,2-dichloroethene.png
| ImageSizeR1 = 110px
| ImageNameR1 = Skeletal formula of trans-1,2-dichloroethene | ImageNameR1 = Skeletal formula of trans-1,2-dichloroethene
| ImageFileL2 = Cis-dichloroethylene-3D-balls.png | ImageFileL2 = Cis-1,2-dichloroethene-3D-balls.png
| ImageSizeL2 = 110px
| ImageNameL2 = Ball-and-stick model of cis-1,2-dichloroethene | ImageNameL2 = Ball-and-stick model of cis-1,2-dichloroethene
| ImageFileR2 = Trans-dichloroethylene-3D-balls.png | ImageFileR2 = Trans-1,2-dichloroethene-3D-balls.png
| ImageSizeR2 = 110px
| ImageNameR2 = Ball-and-stick model of trans-1,2-dichloroethene | ImageNameR2 = Ball-and-stick model of trans-1,2-dichloroethene
| IUPACName = 1,2-Dichloroethene | ImageCaptionL2= ''cis''-1,2-Dichloroethene (''Z'')
| ImageCaptionR2= ''trans''-1,2-Dichloroethene (''E'')
| OtherNames = 1,2-Dichloroethylene<br />1,2-DCE
| PIN = 1,2-Dichloroethene
| OtherNames = 1,2-Dichloroethene<br />1,2-DCE<br/>Acetylene dichloride<br />''sym''-Dichloroethylene
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 22: Line 20:
| ChEBI = 18882 | ChEBI = 18882
| ChemSpiderID = 10438 | ChemSpiderID = 10438
| EINECS = 208-750-2
| PubChem = 643833
| PubChem_Comment = (''Z'')
| PubChem1 = 638186
| PubChem1_Comment = (''E'')
| PubChem2 = 10900
| PubChem2_Comment = (''E''/''Z'')
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06792 | KEGG = C06792
Line 35: Line 40:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 156-59-2 | CASNo = 156-59-2
| CASNo_Comment = (Z) | CASNo_Comment = (''Z'')
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1 = 156-60-5 | CASNo1 = 156-60-5
| CASNo1_Comment = (E) | CASNo1_Comment = (''E'')
| CASNo2_Ref = {{cascite|correct|??}}
| CASNo2 = 540-59-0 | CASNo2 = 540-59-0
| CASNo2_Comment = (racemate) | CASNo2_Comment = (''E''/''Z'')
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FYO9G15JYD
| UNII_Comment = (''Z'')
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 41799BI61U
| UNII1_Comment = (''E'')
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = XU9RUA6YUT
| UNII2_Comment = (''E''/''Z'')
| SMILES = Cl=CCl | SMILES = Cl=CCl
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>2</sub>Cl<sub>2</sub> | Formula = C{{sub|2}}H{{sub|2}}Cl{{sub|2}}
| MolarMass = 96.95 g/mol | MolarMass = 96.95 g/mol
| Density = Z: 1.28 g/cm³<br />E: 1.26 g/cm³ | Density = ''Z'': 1.28 g/cm{{sup|3}}<br />''E'': 1.26 g/cm{{sup|3}}
| MeltingPt = Z: -81 °C<br />E: -81 °C | MeltingPt = ''Z'': −81.47 °C<br />''E'': −49.44 °C
| BoilingPt = Z: 60.3 °C<br />E: 47.5 °C | BoilingPt = ''Z'': 60.2 °C<br />''E'': 48.5 °C
| Dipole = Z (cis): 1.9 ]<br />E (trans): 0 ] | Dipole = ''Z'': 1.9 ]<br />''E'': 0 ]
| Appearance = colorless liquid
| Odor = sweet<ref name=Ullmann/>
| MagSus = {{Plainlist|
* −51.0·10{{sup|−6}} cm{{sup|3}}/mol (cis)
* −48.9·10{{sup|−6}} cm{{sup|3}}/mol (trans)
}}
}} }}
| Section3 = {{Chembox Hazards
| PEL = TWA 200 ppm (790 mg/m{{sup|3}})<ref name=NIOSH>{{PGCH|0195}}</ref>
| FlashPtF = 36-39<ref name=NIOSH/>
| ExploLimits = 5.6–12.8%<ref name=NIOSH/>
| IDLH = 1000 ppm<ref name=NIOSH/>
| REL = TWA 200 ppm (790 mg/m{{sup|3}})<ref name=NIOSH/>
| LC50 = 21,273 ppm (mouse, 6 hr, ''trans''-isomer)<ref name=IDLH>{{IDLH|540590|1,2-Dichloroethylene}}</ref>
| LD50 = 770 mg/kg (oral, rat)<br/>1275 mg/kg (oral, rat, ''trans''-isomer)<ref name=IDLH/>
| LCLo = 16,000 ppm (rat, 6 hr, ''cis''-isomer)<ref name=IDLH/>
}} }}
}}

'''1,2-Dichloroethylene''' or '''1,2-DCE''' is the name for a pair of ] with the molecular formula {{chem2|C2H2Cl2}}. The two compounds are isomers, each being colorless liquids with a sweet odor. It can exist as either of two ], ''cis''-1,2-dichloroethene or ''trans''-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent.<ref name=Ullmann>{{cite book | author = E.-L. Dreher | author2 = T. R. Torkelson | author3 = K. K. Beutel | chapter = Chlorethanes and Chloroethylenes | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2011 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.o06_o01| isbn = 978-3527306732 }}</ref> In contrast to most ], the ''Z'' isomer (''cis'') is more stable than the ''E'' isomer (''trans'') by 0.4 kcal/mol.<ref>{{cite journal |title= ''cis''- and ''trans''-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.{{sup|–1}} and the Thermodynamic Properties |first1= Kenneth S. |last1= Pitzer |first2= J. L. |last2= Hollenberg |journal= J. Am. Chem. Soc. |year= 1954 |volume= 76 |issue= 6 | pages= 1493–1496 |doi= 10.1021/ja01635a010 }}</ref>

==Production, uses and reactions==
''cis''-DCE, the ''Z'' isomer, is obtainable by the controlled ] of ]:

:C{{sub|2}}H{{sub|2}} + Cl{{sub|2}} → C{{sub|2}}H{{sub|2}}Cl{{sub|2}}

Industrially both isomers arise as byproducts of the production of ], which is produced on a vast scale. Unlike ], the 1,2-dichloroethylene isomers do not polymerize.<ref name=Ullmann/>

''trans''-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.<ref>{{Cite web |url=http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ |title=Chlorinated Solvents and Feed Stock - Axiall |access-date=2016-03-23 |archive-url=https://web.archive.org/web/20160408122850/http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ |archive-date=2016-04-08 |url-status=dead }}</ref>

Both isomers participate in ] reactions. ''trans''-1,2-Dichloroethylene participates in ]s.<ref>{{cite journal |doi=10.1021/jo00078a031|title=Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzocyclooctene: Synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzocyclooctafluorene and 5,6-didehydro-10,11-methano-1H-benzocyclooctafluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzofluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopentatetraphenylene |year=1993 |last1=Wang |first1=Xiao Min |last2=Hou |first2=Xuelong |last3=Zhou |first3=Zhongyuan |last4=Mak |first4=Thomas C. W. |last5=Wong |first5=Henry N. C. |journal=The Journal of Organic Chemistry |volume=58 |issue=26 |pages=7498–7506 }}</ref>

==Safety and environmental concerns==
These compounds have "moderate oral toxicity to rats".<ref name=Ullmann/>

The dichloroethylene isomers occur in some polluted waters and soils, as the decomposition products of ]. Significant attention has been paid to their further degradation, e.g. by iron particles.<ref>{{cite journal|doi=10.1111/j.1574-6976.2010.00210.x|title=Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution |year=2010 |last1=Mattes |first1=Timothy E. |last2=Alexander |first2=Anne K. |last3=Coleman |first3=Nicholas V. |journal=FEMS Microbiology Reviews |volume=34 |issue=4 |pages=445–475 |pmid=20146755 |doi-access=free }}</ref><ref>{{cite journal |doi=10.1021/cm020737i|title=Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles |year=2002 |last1=Schrick |first1=Bettina |last2=Blough |first2=Jennifer L. |last3=Jones |first3=A. Daniel |last4=Mallouk |first4=Thomas E. |journal=Chemistry of Materials |volume=14 |issue=12 |pages=5140–5147 }}</ref>

==See also==
* ]
* ], which is also often abbreviated as 1,2-DCE

==References==
<references/>

==External links==
*{{ICSC|0436|04}}
*{{PGCH|0195}}

{{DEFAULTSORT:Dichloroethene, 1, 2-}}
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