Trichloropropane
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| Names | |
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Preferred IUPAC name
1,2,3-Trichloropropane
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| Other names
TCP
Allyl trichloride Glycerol trichlorohydrin Trichlorohydrin |
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| Identifiers | |
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3D model (JSmol)
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| Abbreviations | TCP |
| ChemSpider | |
| ECHA InfoCard | 100.002.261 |
| EC Number | 202-486-1 |
| KEGG | |
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| Properties | |
| C 3H 5Cl 3 |
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| Molar mass | 147.43 g |
| Appearance | colorless or straw yellow transparent liquid |
| Odor | chloroform-like |
| Density | 1.387g/mL |
| Melting point | −14 °C (7 °F; 259 K) |
| Boiling point | 156.85 °C (314.33 °F; 430.00 K) |
| 1,750 mg/L | |
| log P | 2.27 |
| Vapor pressure | 3 mmHg (20°C) |
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Henry's law
constant (kH) |
4.087 x 10−4 |
| Hazards | |
| Flash point | 71 °C; 160 °F; 344 K |
| Explosive limits | 3.2%-12.6% |
| Lethal dose or concentration (LD, LC): | |
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LC50 (median concentration)
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555 ppm (mouse, 2 hr) |
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LCLo (lowest published)
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5000 ppm (mouse, 20 min) |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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TWA 50 ppm (300 mg/m3) |
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REL (Recommended)
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Ca TWA 10 ppm (60 mg/m3) [skin] |
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IDLH (Immediate danger)
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Ca [100 ppm] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
1,2,3-Trichloropropane (TCP) is a chemical compound that was an impurity in 1,3-dichloropropene fumigants manufactured by Shell Chemical Company and Dow Chemical Company. Exposure by inhalation, skin contact, or ingestion can be harmful to health.
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.
Historically, TCP has been used as a paint or varnish remover, a cleaning and degreasing agent, and was an impurity in certain pesticides. It is also used as a chemical intermediate in the process of making chemicals, such as hexafluoropropylene and polysulfides, and as an industrial solvent.
1,2,3-TCP had purportedly been used in the past as a solvent for paint and varnish removal, as a cleaning and degreasing agent, and as a cleaning and maintenance solvent. No current information is available to indicate that it continues to be used for these purposes.
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.
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