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1,2,3-Trichloropropane

Names
IUPAC name 1,2,3-Trichloropropane
Systematic IUPAC name Trichloropropane
Other names TCP; Allyl trichloride; Glycerol trichlorohydrin; Trichlorohydrin
Identifiers
CAS Number	96-18-4
Abbreviations	TCP
ChEMBL	ChEMBL346933
ChemSpider	7013
ECHA InfoCard	100.002.261
EC Number	202-486-1
KEGG	C14400
CompTox Dashboard (EPA)	DTXSID9021390
InChI InChI=1S/C3H5Cl3/c4-1-3(6)2-5/h3H,1-2H2Key: CFXQEHVMCRXUSD-UHFFFAOYSA-N
Properties
Chemical formula	C 3H 5Cl 3
Molar mass	147.43 g
Appearance	colorless or straw yellow transparent liquid
Density	1.38g mol
Melting point	−14 °C (7 °F; 259 K)
Boiling point	156.85 °C (314.33 °F; 430.00 K)
log P	2.27
Vapor pressure	3.1
Henry's law constant (kH)	4.087 x 10
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

1,2,3-Trichloropropane (TCP) is a chemical compound that is commonly used as an industrial solvent. Although it is not currently labeled as a contaminant by the United States federal government, new research shows that it could have severe health effects. Currently, only California has significant regulation on this compound.

Production

1,2,3-Trichloropropane can be produced via the chlorination of propylene. Other reported methods for producing 1,2,3-trichloropropane include the addition of chlorine to allyl chloride, reaction of thionyl chloride with glycerol, and the reaction of phosphorus pentachloride with either 1,3- or 2,3-dichloropropanol. TCP also may be produced as a byproduct of processes primarily used to produce chemicals such as dichloropropene (a soil fumigant), propylene chlorohydrin, propylene oxide, dichlorohydrin, and glycerol.

Uses

Historically, TCP has been used as a paint or varnish remover, a cleaning and degreasing agent, and in the production of pesticides. Currently, it is also being used as a chemical intermediate in the process of making chemicals such as hexafluoropropylene and polysulfides and as an industrial solvent.

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

Existing regulation

As of now, only the state of California has any regulation on 1,2,3-trichloropropane. Even there, it is only viewed as an unregulated contaminant that should be monitored. 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 (maximum concentration level) for this contaminant. In California, there is only a notification level of .005 ppb (parts per billion) in groundwater. However, other safety and health departments have created limits on how much exposure a person can have to TCP safely. The Permissible Exposure Limit (PEL) is 50 ppm or 300 mg/m. 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.

Proposed US federal regulation

In a new drinking water project that was proposed by the US Environmental Protection Agency (EPA), TCP is one of sixteen chemicals that are being considered for regulation. These sixteen chemicals are all suspected human carcinogens.

TCP as an emerging contaminant

TCP does not contaminate soil. Instead, it leaks down into ground water and settles down at the bottom of the ground water reservoir because TCP is more dense than water. This makes TCP in its pure form a DNAPL (Dense Nonaqueous Phase Liquid)and it is therefore harder to remove it from groundwater. There is no evidence that TCP can naturally decompose, but it might in favorable conditions. Groundwater remediation of TCP can occur through in situ chemical oxidation, permeable reactive barriers, and other remediation techniques. 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. Recent studies suggest that reduction with zerovalent metals, particularly zerovalent zinc, may be particularly effective in TCP remediation. Bioremediation may also be a promising clean-up technique.

References

1. Agency for Toxic Substances and Disease Registry (1992). Toxicological Profile for 1,2,3-Trichloropropane (Report). U.S. CDC.
2. ^ Cooke, Mary (2009). Emerging Contaminant--1,2,3-Trichloropropane (TCP) (Report). United States EPA.
3. Sedman, Richard (2009). Public Health Goals for Chemicals in Drinking Water: 1,2,3-Trichloropropane (Report). California EPA.
4. Basic Questions and Answers for the Drinking Water Strategy Contaminant Groups Effort (PDF) (Report). US EPA. 2011.
5. Stepek, Jan (2009). Groundwater Information Sheet: 1,2,3-Trichloropropane (TCP) (PDF) (Report). California State Water Resources Control Board.
6. Tratnyek, P. G.; Sarathy, V.; Fortuna, J. H. (2008). "Fate and remediation of 1,2,3-trichloropropane". 6th International Conference on Remediation of Chlorinated and Recalcitrant Compounds: Monterey, CA (PDF). Paper C-047.
7. Sarathy, Vaishnavi; Salter, Alexandra J.; Nurmi, James T.; o’Brien Johnson, Graham; Johnson, Richard L.; Tratnyek, Paul G. (2010). "Degradation of 1,2,3-Trichloropropane (TCP): Hydrolysis, Elimination, and Reduction by Iron and Zinc". Environmental Science & Technology. 44 (2): 787. doi:10.1021/es902595j.
8. Bylaska, Eric J.; Glaesemann, Kurt R.; Felmy, Andrew R.; Vasiliu, Monica; Dixon, David A.; Tratnyek, Paul G. (2010). "Free Energies for Degradation Reactions of 1,2,3-Trichloropropane from ab Initio Electronic Structure Theory". The Journal of Physical Chemistry A. 114 (46): 12269–82. doi:10.1021/jp105726u. PMID 21038905.
9. Salter-Blanc, Alexandra J.; Tratnyek, Paul G. (2011). "Effects of Solution Chemistry on the Dechlorination of 1,2,3-Trichloropropane by Zero-Valent Zinc". Environmental Science & Technology. 45 (9): 4073–4079. doi:10.1021/es104081p.
10. Pavlova, Martina; Klvana, Martin; Prokop, Zbynek; Chaloupkova, Radka; Banas, Pavel; Otyepka, Michal; Wade, Rebecca C; Tsuda, Masataka; Nagata, Yuji (2009). "Redesigning dehalogenase access tunnels as a strategy for degrading an anthropogenic substrate". Nature Chemical Biology. 5 (10): 727–33. doi:10.1038/nchembio.205. PMID 19701186.
11. Yan, J.; Rash, B. A.; Rainey, F. A.; Moe, W. M. (2009). "Isolation of novel bacteria within theChloroflexicapable of reductive dechlorination of 1,2,3-trichloropropane". Environmental Microbiology. 11 (4): 833–43. doi:10.1111/j.1462-2920.2008.01804.x. PMID 19396942.

External Links

California Department of Public Health

• Organochlorides
• Halogenated solvents
• IARC Group 2A carcinogens