1,2,3-Trichloropropane

changed changed 477202504 1,2,3-Trichloropropane 1,2,3-trichloropropane.svg 1,2,3-Trichloropropane-3D-balls.png Trichloropropane 1,2,3-Trichloropropane TCPAllyl trichlorideGlycerol trichlorohydrinTrichlorohydrin TCP 96-18-4 correct CAS 34036 correct EBI 346933 7285 correct chemspider 7013 202-486-1 correct drugbank correct kegg C14400 TZ9275000 2810 3MJ7QCK0Z0 correct chemspider 1S/C3H5Cl3/c4-1-3(6)2-5/h3H,1-2H2 correct chemspider CFXQEHVMCRXUSD-UHFFFAOYSA-N ClCC(Cl)CCl C 3 H 5 Cl 3 147.43 g colorless or straw yellow transparent liquid chloroform-like 1.387g/mL -14 156.85 2.27 1,750 mg/L 3 mmHg (20°C) 4.087 x 10−4 07 08 Warning 302 312 332 350 360F 201 202 261 264 270 271 280 281 301+312 302+352 304+312 304+340 308+313 312 322 330 363 405 501 160 3.2%-12.6% TWA 50 ppm (300 mg/m3)0631 Ca [100 ppm] Ca TWA 10 ppm (60 mg/m3) [skin] 555 ppm (mouse, 2 hr)96184 1,2,3-Trichloropropane 5000 ppm (mouse, 20 min) 1,2,3-Trichloropropane (TCP) is an organic compound with the formula CHCl(CH2Cl)2. It is a colorless liquid that is used as a solvent and in other specialty applications. Production 1,2,3-Trichloropropane is produced by the addition of chlorine to allyl chloride. Rossberg M. Lendle W. Pfleiderer G. Tögel A. Dreher E. L. Langer E. Rassaerts H. Kleinschmidt P. Strack H. Cook R. Beck U. Lipper K.-A. Torkelson T.R. Löser E. Beutel K.K. Mann T. Chlorinated Hydrocarbons 2006 3527306730 10.1002/14356007.a06_233.pub2 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 epichlorohydrin and dichloropropene.Toxicological Profile for 1,2,3-Trichloropropane U.S. CDC – Agency for Toxic Substances and Disease Registry 1992 https://www.atsdr.cdc.gov/toxprofiledocs/index.html?id=912&tid=186Interim Guidance for Investigating Potential 1,2,3-Trichloropropane Sources in San Gabriel Valley Area 3 U.S. EPA 2005 http://yosemite.epa.gov/r9/sfund/r9sfdocw.nsf/3dc283e6c5d6056f88257426007417a2/a554456e6ae6250a8825771c007c9c60/$FILE/REVISED_123-TCP%20Interim%20Guidance.pdf https://web.archive.org/web/20140413140527/http://yosemite.epa.gov/r9/sfund/r9sfdocw.nsf/3dc283e6c5d6056f88257426007417a2/a554456e6ae6250a8825771c007c9c60/$FILE/REVISED_123-TCP%20Interim%20Guidance.pdf dead April 13, 2014 Uses Historically, TCP has been used as a paint or varnish remover, a cleaning and degreasing agent, an anaesthetic and a solvent. It is also used as an intermediate in the production of hexafluoropropylene. https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P1000SKK.txt Cooke Mary United States EPA Emerging Contaminant--1,2,3-Trichloropropane (TCP) 2009 It is a crosslinking agent for polysulfide 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 carcinogen, 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. Regulation United States Proposed federal regulation 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 United States Environmental Protection Agency (EPA), TCP was one of sixteen suspected human carcinogens being considered for regulation in 2011. US EPA Basic Questions and Answers for the Drinking Water Strategy Contaminant Groups Effort 2011 http://water.epa.gov/lawsregs/rulesregs/sdwa/dwstrategy/upload/FactSheet_DrinkingWaterStrategy_VOCs.pdf https://web.archive.org/web/20110212001804/http://water.epa.gov/lawsregs/rulesregs/sdwa/dwstrategy/upload/FactSheet_DrinkingWaterStrategy_VOCs.pdf dead February 12, 2011 State regulation Pre-1980s, agricultural use of chloropropane-containing soil fumigants for use as pesticides and nematicides 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 ng/L (parts per trillion).https://www.waterboards.ca.gov/drinking_water/certlic/drinkingwater/123TCP.html 123-TCP waterboards.ca.gov 2017-12-30 The state of Alaska has promulgated standards establishing cleanup levels for 1,2,3-trichloropropane contamination in soils and groundwater.http://dec.alaska.gov/commish/regulations/pdfs/18%20AAC%2075.pdf 18 AAC 75 Oil and Other Hazardous Substances Pollution Control Revised as of May 8, 2016 2018-11-26 https://web.archive.org/web/20170211195437/https://dec.alaska.gov/commish/regulations/pdfs/18%20AAC%2075.pdf 2017-02-11 dead 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 mg/m3. 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 (Koc). Instead, it is likely to rapidly either leach from soil into groundwater or evaporate from soil surfaces.(United States Environmental Protection Agency, Federal Facilities Restoration and Reuse Office, 2014) Because TCP is more dense 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 (Dense Nonaqueous Phase Liquid) and it can be more difficult to remediate groundwater. 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 in situ chemical oxidation, permeable reactive barriers, and other remediation techniques.Jan Stepek https://www.waterboards.ca.gov/water_issues/programs/gama/docs/coc_tcp123.pdf California State Water Resources Control Board Groundwater Information Sheet: 1,2,3-Trichloropropane (TCP) 2009 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.http://www.ebs.ogi.edu/tratnyek/resources/docs/TratnyekSarathyFortuna08-TCP.pdf Tratnyek P. G. Sarathy V. Fortuna J. H. Fate and remediation of 1,2,3-trichloropropane 6th International Conference on Remediation of Chlorinated and Recalcitrant Compounds: Monterey, CA 2008 Paper C-047 2018-11-26 https://web.archive.org/web/20120330120556/http://www.ebs.ogi.edu/tratnyek/resources/docs/TratnyekSarathyFortuna08-TCP.pdf 2012-03-30 dead Recent studies suggest that reduction with zerovalent metals, particularly zerovalent zinc, may be particularly effective in TCP remediation.10.1021/es902595j Degradation of 1,2,3-Trichloropropane (TCP): Hydrolysis, Elimination, and Reduction by Iron and Zinc 2010 Sarathy Vaishnavi Salter Alexandra J. Nurmi James T. O’Brien Johnson Graham Johnson Richard L. Tratnyek Paul G. Environmental Science & Technology 44 2 787–793 2000073210.1021/jp105726u Free Energies for Degradation Reactions of 1,2,3-Trichloropropane from ab Initio Electronic Structure Theory 2010 Bylaska Eric J. Glaesemann Kurt R. Felmy Andrew R. Vasiliu Monica Dixon David A. Tratnyek Paul G. The Journal of Physical Chemistry A 114 46 12269–82 2103890510.1021/es104081p Effects of Solution Chemistry on the Dechlorination of 1,2,3-Trichloropropane by Zero-Valent Zinc 2011 Salter-Blanc Alexandra J. Tratnyek Paul G. Environmental Science & Technology 4073–4079 45 9 21486040 free Bioremediation may also be a promising clean-up technique.10.1038/nchembio.205 Redesigning dehalogenase access tunnels as a strategy for degrading an anthropogenic substrate 2009 Pavlova Martina Klvana Martin Prokop Zbynek Chaloupkova Radka Banas Pavel Otyepka Michal Wade Rebecca C Tsuda Masataka Nagata Yuji Damborsky J Nature Chemical Biology 5 10 727–33 1970118610.1111/j.1462-2920.2008.01804.x Isolation of novel bacteria within the Chloroflexi capable of reductive dechlorination of 1,2,3-trichloropropane 2009 Yan J. Rash B. A. Rainey F. A. Moe W. M. Environmental Microbiology 11 4 833–43 19396942 References External links California Department of Public Health CDC – NIOSH Pocket Guide to Chemical Hazards Category:Chloroalkanes Category:Halogenated solvents Category:IARC Group 2A carcinogens