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Revision as of 16:04, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476141684 of page 1,2,3-Trichloropropane for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 18:15, 9 May 2024 edit BerryForPerpetuity (talk | contribs)Extended confirmed users, Rollbackers2,262 edits Reverting edit(s) by Deary1 (talk) to rev. 1193504251 by Ira Leviton: Vandalism (UV 0.1.5)Tags: Ultraviolet Undo 
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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 | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 456494356
| verifiedrevid =477202504
| Name = 1,2,3-Trichloropropane
| ImageFile1 = 1,2,3-trichloropropane.svg | Name =1,2,3-Trichloropropane
| ImageFile1 =1,2,3-trichloropropane.svg
| ImageSize1 = 200px
| ImageFile2 = 1,2,3-Trichloropropane-3D-balls.png | ImageFile2 =1,2,3-Trichloropropane-3D-balls.png
| ImageAlt =
| ImageSize2 = 200px
| ImageCaption =Trichloropropane
| ImageAlt =
| ImageCaption = Trichloropropane | PIN = 1,2,3-Trichloropropane
| OtherNames = TCP<br />Allyl trichloride<br />Glycerol trichlorohydrin<br />Trichlorohydrin
| IUPACName = 1,2,3-Trichloropropane
|Section1={{Chembox Identifiers
| SystematicName = Trichloropropane
| Abbreviations = TCP
| OtherNames = TCP; Allyl trichloride; Glycerol trichlorohydrin; Trichlorohydrin
| CASNo = 96-18-4
| Section1 = {{Chembox Identifiers
| CASNo_Comment =
| Abbreviations = TCP
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 96-18-4 -->
| CASNo_Comment = | ChEBI = 34036
| CASNo_Ref = {{cascite|changed|??}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| CASNos =
| CASOther =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 346933 | ChEMBL = 346933
| PubChem = | PubChem =7285
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem_Comment =
| PubChem5 =
| PubChem5_Comment =
| PubChemOther =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7013 | ChemSpiderID = 7013
| EINECS = 202-486-1
| ChemSpiderID_Comment =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID5 =
| ChemSpiderIDOther =
| EINECS = 202-486-1
| EC-number =
| EINECSCASNO =
| UNNumber =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| KEGG_Ref = {{keggcite|correct|kegg}} | Gmelin =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG = C14400
| MeSHName = | MeSHName =
| RTECS = TZ9275000
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | UNNumber = 2810
| RTECS = | UNII = 3MJ7QCK0Z0
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| ATCvet =
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H5Cl3/c4-1-3(6)2-5/h3H,1-2H2 | StdInChI = 1S/C3H5Cl3/c4-1-3(6)2-5/h3H,1-2H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CFXQEHVMCRXUSD-UHFFFAOYSA-N | StdInChIKey = CFXQEHVMCRXUSD-UHFFFAOYSA-N
| SMILES = | SMILES = ClCC(Cl)CCl
}}
| InChI =
|Section2={{Chembox Properties
| Beilstein =
| Formula = {{chem|C|3|H|5|Cl|3}}
| Gmelin =
| MolarMass = 147.43 g
| KEGG_Ref = {{keggcite|correct|kegg}}
| Appearance = colorless or straw yellow transparent liquid
| KEGG = C14400
| Odor = ]-like<ref name=PGCH />
| 3DMet =}}
| Density = 1.387g/mL
| Section2 = {{Chembox Properties
| MeltingPtC = -14
| Formula = {{chem|C|3|H|5|Cl|3}}
| MeltingPt_notes =
| MolarMass = 147.43 g
| BoilingPtC = 156.85
| Appearance = colorless or straw yellow transparent liquid
| BoilingPt_notes =
| Density = 1.38g mol<sup>-1</sup>
| MeltingPtC = -14 | LogP = 2.27
| Solubility = 1,750 mg/L
| Melting_notes =
| VaporPressure = 3 mmHg (20°C)<ref name=PGCH />
| BoilingPtC = 156.85
| HenryConstant = 4.087 x 10{{sup|−4}}
| Boiling_notes =
| AtmosphericOHRateConstant =
| LogP = 2.27
| pKa =
| VaporPressure = 3.1
| pKb =}}
| HenryConstant = 4.087 x 10<sup>-4</sup>
|Section3={{Chembox Structure
| AtmosphericOHRateConstant =
| pKa = | CrystalStruct =
| pKb = | Coordination =
| Sheet Resistance = | MolShape = }}
|Section4={{Chembox Thermochemistry
| Methacrylate Equiv Wt =
| DeltaHf =
| Bulk Conductivity = }}
| DeltaHc =
| Section3 = {{Chembox Structure
| Entropy =
| CrystalStruct =
| Coordination = | HeatCapacity =
}}
| MolShape = }}
| Section4 = {{Chembox Thermochemistry |Section7={{Chembox Hazards
| ExternalSDS =
| Solubility = 1,750 mg/L
| SolubleOther = | MainHazards =
| Solvent = = | NFPA-H =
| DeltaHc = | NFPA-F =
| NFPA-R =
| DeltaHf
| Entropy = | NFPA-S =
| GHSPictograms = {{GHS07}}{{GHS08}}
| HeatCapacity = }}
| GHSSignalWord = Warning
| Section7 = {{Chembox Hazards
| HPhrases = {{H-phrases|302|312|332|350|360F}}
| ExternalMSDS =
| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+312|304+340|308+313|312|322|330|363|405|501}}
| EUClass =
| EUIndex = | FlashPtF = 160
| FlashPt_ref = <ref name=PGCH />
| MainHazards =
| NFPA-H = | AutoignitionPt =
| ExploLimits = 3.2%-12.6%<ref name=PGCH />
| NFPA-F =
| NFPA-R = | LD50 =
| PEL = TWA 50 ppm (300 mg/m{{sup|3}})<ref name=PGCH>{{PGCH|0631}}</ref>
| NFPA-O =
| IDLH = Ca <ref name=PGCH />
| RPhrases =
| REL = Ca TWA 10 ppm (60 mg/m{{sup|3}}) <ref name=PGCH />
| SPhrases =
| LC50 = 555 ppm (mouse, 2 hr)<ref name=IDLH>{{IDLH|96184|1,2,3-Trichloropropane}}</ref>
| RSPhrases =
| LCLo = 5000 ppm (mouse, 20 min)<ref name=IDLH/>
| FlashPt =
}}
| Autoignition =
|Section8={{Chembox Related
| ExploLimits =
| LD50 = | OtherAnions =
| PEL = }} | OtherCations =
| OtherFunction =
| Section8 = {{Chembox Related
| OtherFunction_label =
| OtherAnions =
| OtherCations = | OtherCompounds = }}
| OtherFunctn =
| Function =
| OtherCpds = }}
}} }}

'''1,2,3-Trichloropropane''' (TCP) is an ] with the formula CHCl(CH<sub>2</sub>Cl)<sub>2</sub>. It is a colorless liquid that is used as a solvent and in other specialty applications.<ref name=Ross/>

== Production ==
1,2,3-Trichloropropane is produced by the addition of chlorine to ].<ref name=Ross>{{Ullmann | last1 = Rossberg | first1 = M. | last2 = Lendle | first2 = W. | last3 = Pfleiderer | first3 = G. | last4 = Tögel | first4 = A. | last5 = Dreher | first5 = E. L. | last6 = Langer | first6 = E. | last7 = Rassaerts | first7 = H. | last8 = Kleinschmidt | first8 = P. | last9 = Strack | first9 = H. | last10 = Cook | first10 = R. | last11 = Beck | first11 = U. | last12 = Lipper | first12 = K.-A. | last13 = Torkelson | first13 = T.R.| last14 = Löser | first14 = E. | last15 = Beutel | first15 = K.K. | last16 = Mann | first16 = T. | title= Chlorinated Hydrocarbons| year = 2006 | isbn = 3527306730 | doi=10.1002/14356007.a06_233.pub2 | pmc = }}</ref> TCP also may be produced as a by-product also is produced in significant quantities as an unwanted by-product of the production of other chlorinated compounds such as ] and ].<ref name=atsdr>{{cite report|title=Toxicological Profile for 1,2,3-Trichloropropane|publisher= U.S. CDC – Agency for Toxic Substances and Disease Registry |year=1992|url=https://www.atsdr.cdc.gov/toxprofiledocs/index.html?id=912&tid=186}}</ref><ref name=USEPA>{{cite report|title=Interim Guidance for Investigating Potential 1,2,3-Trichloropropane Sources in San Gabriel Valley Area 3|publisher= U.S. EPA|year= 2005|url=http://yosemite.epa.gov/r9/sfund/r9sfdocw.nsf/3dc283e6c5d6056f88257426007417a2/a554456e6ae6250a8825771c007c9c60/$FILE/REVISED_123-TCP%20Interim%20Guidance.pdf}}</ref>

== Uses ==
Historically, TCP has been used as a paint or varnish remover, a ] and degreasing agent, an anaesthetic and a solvent.<ref name=Ross/> It is also used as an intermediate in the production of ].<ref name=epa>{{cite report|url= http://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P1000SKK.txt| last=Cooke|first= Mary|publisher= United States EPA|title= Emerging Contaminant--1,2,3-Trichloropropane (TCP)|year= 2009}}</ref> It is a ] for ] polymers and sealants.

== Effects of exposure ==
Humans can be exposed to TCP by inhaling its fumes or through skin contact and ingestion. TCP is recognized in California as a human ], and extensive animal studies have shown that it causes cancer. Short term exposure to TCP can cause throat and eye irritation and can affect muscle coordination and concentration. Long term exposure can affect body weight and kidney function.<ref name=epa/>

== Regulation ==
===United States===
==== Proposed federal regulation ====
{{As of|2013}} TCP was not regulated as a contaminant by the federal government, but research shows that it could have severe health effects; only the state of California had significant regulation of this compound.

In a drinking water project proposed by the ] (EPA), TCP was one of sixteen suspected human carcinogens being considered for regulation in 2011.<ref name=memo>{{cite report|publisher = US EPA|title=Basic Questions and Answers for the Drinking Water Strategy Contaminant Groups Effort|year=2011|url=http://water.epa.gov/lawsregs/rulesregs/sdwa/dwstrategy/upload/FactSheet_DrinkingWaterStrategy_VOCs.pdf}}</ref>

==== State regulation ====
Pre-1980s, agricultural use of chloropropane-containing ]s for use as pesticides and ]s was prevalent in the United States. Some soil fumigants, which contained a mixture of primarily 1,3-dichloropropene and 1,2-dichloropropane, and in which 1,2,3-TCP was a minor component, e.g., trade name of D-D, were marketed for the cultivation of various crops including citrus fruits, pineapples, soy beans, cotton, tomatoes, and potatoes. D-D was first marketed in 1943, but is no longer available in the United States, and has been replaced with Telone II, which was first available in 1956. Telone II reportedly contains as much as 99 percent 1,3-dichloropropene and up to 0.17 percent by weight 1,2,3-TCP (Zebarth et al., 1998). Before 1978, approximately 55 million pounds/year of 1,3-dichloropropene were produced annually in the United States, and approximately 20 million pounds/year of 1,2-dichloropropane and 1,2,3-TCP were produced as by-products in the production of 1,3-dichloropropene. Over 2 million pounds of pesticides containing 1,3-dichloropropene were used in California alone in 1978. Telone II is still used for vegetables, field crops, fruit and nut trees, grapes, nursery crops, and cotton.

The California State Water Resources Control Board's Division of Drinking Water established an enforceable Maximum Contaminant Level (MCL) of 5&nbsp;ng/L (parts per trillion).<ref name=DDW>{{cite web|url=http://www.waterboards.ca.gov/drinking_water/certlic/drinkingwater/123TCP.shtml |title=123-TCP |publisher=waterboards.ca.gov |access-date=2017-12-30}}</ref> The state of Alaska has promulgated standards establishing cleanup levels for 1,2,3-trichloropropane contamination in soils and groundwater.<ref>{{cite web|url=http://dec.alaska.gov/commish/regulations/pdfs/18%20AAC%2075.pdf|title=18 AAC 75 Oil and Other Hazardous Substances Pollution Control Revised as of May 8, 2016|access-date=2018-11-26|archive-url=https://web.archive.org/web/20170211195437/https://dec.alaska.gov/commish/regulations/pdfs/18%20AAC%2075.pdf|archive-date=2017-02-11|url-status=dead}}</ref> The state of California considers 1,2,3-trichloropropane to be a regulated contaminant that must be monitored. The state of Colorado has also promulgated a groundwater standard although there is no drinking water standard. Although there is not much regulation on this substance, it has proved that TCP is a carcinogen in laboratory mice, and most likely a human carcinogen as well. On a federal scale, there is no MCL for this contaminant. The Permissible Exposure Limit (PEL) in occupational setting for air is 50 ppm or 300&nbsp;mg/m{{sup|3}}. The concentration in air at which TCP becomes an Immediate Danger to Life and Health (IDLH) is at 100 ppm. These regulations were reviewed in 2009.

== TCP as an emerging contaminant ==
TCP does not readily adsorb to soil based on its low soil organic carbon-water partition coefficient (K<sub>oc</sub>). Instead, it is likely to rapidly either leach from soil into ] or evaporate from soil surfaces.<ref>(United States Environmental Protection Agency, Federal Facilities Restoration and Reuse Office, 2014)</ref> Because TCP is more ] than water, in groundwater aquifers, it would be more likely found at the interface with shallower higher permeability soil stratum and the next deeper low permeability soil stratum. This makes TCP in its pure form a DNAPL (]) and it can be more difficult to remediate groundwater.<ref name=epa /> TCP has been shown to undergo biodegradation under anaerobic conditions via reductive dechlorination by Dehalogenimonas (Dhg) species. However, the degradation is typically slower than for other volatile organic compounds. Groundwater remediation of TCP can occur through ], ]s, and other remediation techniques.<ref name=GAMPA>{{cite report|first=Jan |last=Stepek|url=http://www.swrcb.ca.gov/water_issues/programs/gama/docs/coc_tcp123.pdf|publisher=California State Water Resources Control Board|title=Groundwater Information Sheet: 1,2,3-Trichloropropane (TCP)|year= 2009}}</ref> Several TCP remediation strategies have been studied and/or applied with varying degrees of success. These include extraction with granular activated carbon, in situ chemical oxidation, and in situ chemical reduction.<ref>{{cite book|url=http://www.ebs.ogi.edu/tratnyek/resources/docs/TratnyekSarathyFortuna08-TCP.pdf|last1=Tratnyek|first1=P. G.|last2=Sarathy|first2=V.|last3=Fortuna|first3=J. H.|chapter=Fate and remediation of 1,2,3-trichloropropane|title=6th International Conference on Remediation of Chlorinated and Recalcitrant Compounds: Monterey, CA|year=2008|id=Paper C-047|access-date=2018-11-26|archive-url=https://web.archive.org/web/20120330120556/http://www.ebs.ogi.edu/tratnyek/resources/docs/TratnyekSarathyFortuna08-TCP.pdf|archive-date=2012-03-30|url-status=dead}}</ref> Recent studies suggest that reduction with zerovalent metals, particularly zerovalent zinc, may be particularly effective in TCP remediation.<ref>{{cite journal|doi=10.1021/es902595j|title=Degradation of 1,2,3-Trichloropropane (TCP): Hydrolysis, Elimination, and Reduction by Iron and Zinc|year=2010|last1=Sarathy|first1=Vaishnavi|last2=Salter|first2=Alexandra J.|last3=Nurmi|first3=James T.|last4=O’Brien Johnson|first4=Graham|last5=Johnson|first5=Richard L.|last6=Tratnyek|first6=Paul G.|journal=Environmental Science & Technology|volume=44|issue=2|pages=787–793|pmid=20000732}}</ref><ref>{{cite journal|doi=10.1021/jp105726u|title=Free Energies for Degradation Reactions of 1,2,3-Trichloropropane from ab Initio Electronic Structure Theory|year=2010|last1=Bylaska|first1=Eric J.|last2=Glaesemann|first2=Kurt R.|last3=Felmy|first3=Andrew R.|last4=Vasiliu|first4=Monica|last5=Dixon|first5=David A.|last6=Tratnyek|first6=Paul G.|journal=The Journal of Physical Chemistry A|volume=114|issue=46|pages=12269–82|pmid=21038905}}</ref><ref>{{cite journal|doi=10.1021/es104081p|title=Effects of Solution Chemistry on the Dechlorination of 1,2,3-Trichloropropane by Zero-Valent Zinc|year=2011|last1=Salter-Blanc|first1=Alexandra J.|last2=Tratnyek|first2=Paul G.|journal=Environmental Science & Technology|pages=4073–4079|volume=45 |issue=9|pmid=21486040|doi-access=free}}</ref> ] may also be a promising clean-up technique.<ref>{{cite journal|doi=10.1038/nchembio.205|title=Redesigning dehalogenase access tunnels as a strategy for degrading an anthropogenic substrate|year=2009|last1=Pavlova|first1=Martina|last2=Klvana|first2=Martin|last3=Prokop|first3=Zbynek|last4=Chaloupkova|first4=Radka|last5=Banas|first5=Pavel|last6=Otyepka|first6=Michal|last7=Wade|first7=Rebecca C|last8=Tsuda|first8=Masataka|last9=Nagata|first9=Yuji|last10=Damborsky|first10=J|journal=Nature Chemical Biology|volume=5|issue=10|pages=727–33|pmid=19701186}}</ref><ref>{{cite journal|doi=10.1111/j.1462-2920.2008.01804.x|title=Isolation of novel bacteria within the ''Chloroflexi'' capable of reductive dechlorination of 1,2,3-trichloropropane|year=2009|last1=Yan|first1=J.|last2=Rash|first2=B. A.|last3=Rainey|first3=F. A.|last4=Moe|first4=W. M.|journal=Environmental Microbiology|volume=11|issue=4|pages=833–43|pmid=19396942}}</ref>

== References ==
{{Reflist}}

== External links ==
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{{Authority control}}

{{DEFAULTSORT:Trichloropropane, 1, 2, 3-}}
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