96-18-4

Usage

Source

Produced in large quantities as an epichlorohydrin production byproduct, TCP is a synthetic compound that does not occur naturally in the environment. In the agrochemical industry, TCP is formed via the manufacture of dichloropropene-derived nematicides (pesticides used to kill parasitic nematodes), and it is also present as an impurity in these soil fumigants. As a result, application of these products has produced significant atmosphere, soil, and groundwater contamination, which in turn can induce various health problems in wildlife and humans. The toxicological effects of TCP depend on dose and duration, but can range from kidney and liver damage to tumors and cancers.

health standards

The EPA has established drinking water health advisories for 1,2,3-Trichloropropane, which are drinking water specific risk level concentrations for cancer (10-4 cancer risk) and concentrations of drinking water contaminants at which noncancer adverse health effects are not anticipated to occur over specific exposure durations. EPA established a 1-day health advisory of 0.6 milligrams per liter (mg/L) and a 10-day health advisory of 0.6 mg/L for TCP in drinking water for a 10 kilogram (kg) child (EPA 2012a).

Reference

Samin, G, and D. B. Janssen. "Transformation and biodegradation of 1,2,3-trichloropropane (TCP). " Environmental Science & Pollution Research 19.8(2012): 3067-3078. Liu, P., et al. "Successful therapy with hemoperfusion and plasma exchange in acute 1,2,3-trichloropropane poisoning." Human & Experimental Toxicology 31.5(2012): 523-527.

Reactivity Profile

1,2,3-Trichloropropane is sensitive to prolonged exposure to light. Sensitive to heat. May react with active metals, strong caustics and oxidizing agents. Attacks some plastics, rubber and some coatings .

Health Hazard

Inhalation of vapor causes anesthesia, dizziness, and nausea. Vapor is highly irritating by inhalation routes and moderately irritating by dermal routes. Exposure of eyes to vapor may result in slight, transient injury to the cornea.

Health Hazard

Inhalation of its vapors can produce depres sion of the central nervous system, which canprogress to narcosis and convulsion as theconcentration increases. A 30-minute expo sure to a 5000-ppm concentration causedconvulsions in rats. Acute as well as chronicexposure to high concentrations can causeliver damage. 1,2,3-Trichloropropane is moretoxic than its 1,1,1-isomer. Acute oral tox icity is moderate, with LD50 values rang ing between 300 and 550 mg/kg in differentspecies of experimental animals. The liquidis a strong irritant to the eyes.

Fire Hazard

Combustible liquid; flash point (closed cup) 73°C (164°F), (open cup) 82°C (180°F). Vapors of 1,2,3-trichloropropane form explo sive mixtures with air, with LEL and UEL values of 3.2% and 12.6% by volume in air, respectively. The compound reacts vigorously with alkali metals, powdered magnesium, or aluminum; caustic alkalies; and oxidizers.

Flammability and Explosibility

Nonflammable

Safety Profile

Confirmed carcinogen. Poison by ingestion. Moderately toxic by inhalation and skin contact. Experimental reproductive effects. A skin and severe eye irritant. Mutation data reported. Moderately flammable by heat, flames (sparks), or powerful oxidizers. See also ALLYL COMPOUNDS and CHLORINATED HYDROCARBONS, ALIPHATIC. When heated to decomposition it yields hghly toxic Cl-. To fight fre, use water (as a blanket), spray, mist, dry chemical.

Potential Exposure

Trichloropropane dissolves oils, fats, waxes, chlorinated rubber; and numerous resins; it is used as a paint and varnish remover; a solvent; and a degreasing agent.

Carcinogenicity

1,2,3-Trichloropropane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental fate

Chemical/Physical. The hydrolysis rate constant for 1,2,3-trichloropropane at pH 7 and 25 °C was determined to be 1.8 x 10-6/h, resulting in a half-life of 43.9 yr (Ellington et al., 1988). The hydrolysis half-lives decrease at varying pHs and temperature. At 87 °C, the hydrolysis half-lives at pH values of 3.07, 7.12, and 9.71 were 21.1, 11.6, and 0.03 d, respectively (Ellington et al., 1986). By analogy to 1,2-dibromo-2-chloropropane, the following hydrolysis products would be formed: 2,3-dichloro-1-propanol, 2,3-dichloropropene, epichlorohydrin, 1-chloro-2,3- dihydroxypropane, glycerol, 1-hydroxy-2,3-propylene oxide, 2-chloro-3-hydroxypropene, and HCl (Kollig, 1993). The volatilization half-life of 1,2,3-trichloropropane (1 mg/L) from water at 25 °C using a shallow-pitch propeller stirrer at 200 rpm at an average depth of 6.5 cm was 56.1 min (Dilling, 1977).

Toxicity evaluation

It is currently believed that TCP itself has very low activity, while its metabolites mainly cause toxicity, carcinogenicity, and other effects. The liver can metabolize TCP by cytochrome P450 enzymes to give reactive intermediates, which bind to glutathione or other protein for excretion. The reactive intermediates can bind to DNA, proteins, and other molecules and cause hepatocellular damage, gene mutation, and organ dysfunction. Activation of the molecule may occur by reaction with glutathione. The metabolites (e.g., dichloroacetone) accumulated through glutathione depletion and consequently covalent binding to DNA and other macromolecules such as microsomal proteins.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent decomposition with chemically active metals; strong bases. Keep away from chlorinated rubber, resins and waxes; and sunlight.

InChI:InChI=1/C3H5Cl3/c4-1-3(6)2-5/h3H,1-2H2

Upstream product

• 75-30-9 2-iodo-propane 
• 74-87-3 methylene chloride 
• 187737-37-7 propene 
• 870-76-8 chlorosulfuric acid 2-chloro-1-chloromethyl-ethyl ester 
• 872819-04-0 chlorosulfuric acid-(2,3-dichloro-propyl ester) 
• 872272-77-0 sulfurous acid bis-(β,β'-dichloro-isopropyl ester) 
• 26198-63-0 1,2-Dichloropropane 
• 74-98-6 propane 
• 56-81-5 glycerol 
• 107-05-1 3-chloroprop-1-ene 
• 106-89-8 epichlorohydrin 
• 627-40-7 methylallylether 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 

Downstream Products

• 591-76-4 2-Methylhexane 
• 464-06-2 triptane 
• 590-35-2 2,2-dimethylpentane 
• 555-45-3 tritetradecanoylglycerol 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 4756-13-2 1,2,3-propanetrithiol 
• 18495-30-2 1,1,2,3-tetrachloropropane 
• 38729-96-3 2-chloroallylamine 
• 64531-10-8 bis-(2-chloro-allyl)-amine 
• 56-81-5 glycerol 
• 101096-57-5 2-chloro-1,3-bis-(4-chloro-phenylsulfanyl)-propane 
• 56374-49-3 1,2,3-triphenylpropane 
• 1081-75-0 1,3-diphenylpropane 

Relevant academic research and scientific papers

Continuous flow preparation method 1,trichlorhydrin

The invention relates to a continuous flow preparation method of 1,when 3 - chloropropene liquid and liquid chlorine are pumped into the reaction device through the metering pump, and the reaction is continuously reacted under -20 - 30 °C conditions to obtain 1,trichlorhydrin. Compared with the prior art, the technical scheme provided by the invention has the advantages of small liquid holding amount, large liquid chlorine gas flux, good mass transfer heat transfer effect, short reaction time, no byproduct generation, less occupied area, high product yield and high content, and is safe and reliable in reaction and suitable for large-scale industrial production.

Novel method for producing 2-amino-1, 3-propylene glycol by JIT method

The invention belongs to the field of fine chemical engineering, and relates to a novel method for producing 2-amino-1, 3-propylene glycol by a JIT method, the novel method is composed of a catalytic chlorination reaction and a catalytic amination reaction, glycerol is chlorinated by hydrogen chloride under the catalysis of zinc chloride to obtain 2-chloro-1, 3-propylene glycol, and the 2-chloro-1, 3-propylene glycol is subjected to a catalytic reaction by urotropin to obtain 2-chloro-1, 3-propylene glycol.

Synthesis method of 2,3-dichloropropene

The invention discloses a synthesis method of 2,3-dichloropropene. The synthesis method comprises the step that 2,3-dichloropropene is obtained through cleavage reaction of 1,2,3-trichloropropane. Thesynthesis method is simple in technology, continuous production is adopted to change a gas-liquid reaction into a gas-gas reaction, the reaction route is short, the cost is low, the benefit is high,and the mole yield is 98% (relative to 1,2,3-trichloropropane). The production efficiency and the equipment utilization rate are high, nitrogen is utilized to dilute and protect 2,3-dichloropropene, the product quality is stable, and the technology is safe and reliable. The technological design is reasonable, the process is safe and controllable, the production fee is low, and no waste water is generated.

Synthesis method of 1,2,3-trichloropropane

The invention discloses a synthesis method of 1,2,3-trichloropropane. The synthesis method comprises the following steps of: after vaporizing 3-chloropropene, reacting with chlorine gas and obtaining1,2,3-trichloropropane. The synthesis method disclosed by the invention has the beneficial effects that the process is simple, continuous production is adopted, gas-liquid reaction is changed into gas-gas reaction, the reaction path is short, the cost is low, the yield is high, and the molar yield is 98%; the production efficiency and the equipment utilization rate are high, and nitrogen gas is used for dilution and protection, so that the product quality is stable, and the process is safe and reliable; the automation degree is high, the process is safe and controllable, the production cost islow and no waste water is produced.

Traditional Chinese medicine composition and preparation method and application thereof

The invention provides traditional Chinese medicines. According to the traditional Chinese medicines, based on the traditional Chinese medicine principle of 'monarch, minister, assistant and guide', the traditional Chinese medicines are reasonablu prepared and are compatible with one another, and thus the purpose of preventing and curing cardiovascular and cerebrovascular diseases is achieved; inthe traditional Chinese medicines, radix ginseng, sanguis draconis, crocus sativus, a ginkgo folium extract and lumbrukinase can improve blood microcirculation in a synergistic mode, blood vessels areexpanded, and discharging of blood poison of heavy metals, lactic acid, fat and the like in the blood is promoted; radix notoginseng, hirudo, radix salviae miltiorrhizae, gastrodiae rhizoma, faeces trogopterori, persicae semen, eupolyphaga, rhizoma chuanxiong and liquidambar infructescence have the efficacy of decreasing the blood pressure, reducing blood fat, improving the human body immunity and clearing and activating the channels and collaterals, the rest medicines are matched for promoting blood microcirculation and achieving the efficacy of clearing and activating the channels and collaterals, and thus the medicine effect is promoted; the medicines are compatible to clear and activate the channels and collaterals, dredge the blood vessels and make blood circulation more smooth, andthe traditional Chinese medicines can effectively prevent and cure the cardiovascular and cerebrovascular diseases. According to a preparation method of a traditional Chinese medicines composition, effective components of ginkgo folium total flavone glycosides and ginkgo folium total lactone in ginkgo folium can be fully extracted, the pertinence of the method is high, and the extraction efficiency of effective components of the medicines is high.

A safer and greener chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate zeolite

Industrial production of dichloropropanols through chlorohydrination of allyl chloride suffers from a series of disadvantages such as use of hazardous Cl2, low atom economy, low dichloropropanol concentration and serious pollution. In this work, a safer and greener route for chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate (HTS) at mild condition is developed. Unlike the traditional Cl2-based chlorohydrination, this novel method is initiated via synergistic effect of Lewis acidity (HTS) and Br?nsted acidity (HCl) to promote occurrence of oxidation, protonation and nucleophilic reaction of allyl chloride simultaneously and hence dichloropropanols are generated. Owing to a completely different reaction route, the formation of 1,2,3-trichloropropane by-product is depressed and the content of dichloropropanol exceeded 22?wt%, which increase by about 4 times compared with traditional Cl2-based chlorohydrination (the content of dichloropropanol is below 4?wt%). At the optimized conditions, both of the allyl chloride conversion and dichloropropanol selectivity could approach 99% simultaneously and the waste is minimized. What's more, the HTS was reusable. Concentrated HCl solution treatment was adopted to test HTS's stability. The characterization and catalytic evaluation results reveal that, although parts of the framework Ti species have transformed into non-framework Ti and then leached into the solution, HTS remains structural stable, and the allyl chloride conversion and dichloropropanol selectivity didn't decrease obviously during the treatment.

Compositions comprising 2,3,3,3-tetrafluoropropene, 1,1,2,3-tetra-chloropropene, 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1,2-tetrafluoropropane

The present disclosure relates to compositions comprising 2,3,3,3-tetrafluoropropene that may be useful as heat transfer compositions, aerosol propellants, foaming agents, blowing agents, solvents, cleaning agents, carrier fluids, displacement drying agents, buffing abrasion agents, polymerization media, expansion agents for polyolefins and polyurethane, gaseous dielectrics, extinguishing agents, and fire suppression agents in liquid or gaseous form. Additionally, the present disclosure relates to compositions comprising 1,1,2,3-tetrachloropropene, 2-chloro-3,3,3-trifluoropropene, or 2-chloro-1,1,1,2-tetrafluoropropane, which may be useful in processes to produce 2,3,3,3-tetrafluoropropene.

Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions

A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri?phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

PROCESS FOR THE PRODUCTION OF CHLORINATED PROPENES

Processes for the production of chlorinated propenes are provided. The processes make use of 1,2-dichloropropane as a starting material and subject a feedstream comprising the same to an ionic chlorination process. At least a portion of any tri- and tetrachlorinated propanes not amenable to ionic chlorination conditions are removed from the ionic chlorination product stream, or, are subjected to chemical base dehydrochlorination step. In this way, recycle of intermediates not amenable to ionic chlorination reactions is reduced or avoided, as is the buildup of these intermediates within the process. Selectivity and, in some embodiments, yield of the process is thus enhanced.

SULFURYL CHLORIDE AS CHLORINATING AGENT

The use of sulfuryl chloride, either alone or in combination with chlorine, as a chlorinating agent is disclosed.