1,2-Dichloropropane

Description

Dichloropropane is a colorless stable liquid.Sweet, chloroform-like odor. The odor threshold in air is0.25 ppm. Molecular weight=112.99; Specific gravity(H2O:1)=1.16; Boiling point=96℃; Freezing/Meltingpoint=-100℃; Vapor pressure=40 mmHg at 20℃;Flash point=16℃ (cc); Autoignition temperature=557℃.Explosive limits: LEL=3.4%; UEL=14.5%. HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 3, Reactivity 0. Very slightly soluble in water; solubility=0.3% at 20℃.

Chemical properties

colourless liquid

Chemical properties

Dichloropropane is a colorless stable liquid. Sweet, chloroform-like odor. The odor threshold in air is 0.25 ppm.

Physical properties

Clear, colorless liquid with a sweet, chloroform-like odor. The average least detectable odor threshold concentration in water at 60 °C was 0.10 mg/L (Alexander et al., 1982). Experimentally determined detection and recognition odor threshold concentrations were 1.2 mg/m³ (260 ppb_v) and 2.4 mg/m³ (520 ppb_v), respectively (Hellman and Small, 1974).

The Uses of 1,2-Dichloropropane

1,2-Dichloropropane is a byproduct in the production of epichlorohydrin (E582310), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links.

The Uses of 1,2-Dichloropropane

Solvent for oils, fats, resins, waxes, rubber; in ion exchange manufacture; in photographic film production; paper coating; petroleum catalyst regeneration. Has been used as a soil fumigant.

The Uses of 1,2-Dichloropropane

Soil fumigant for nematodes.

The Uses of 1,2-Dichloropropane

1,2-Dichloropropane is used as a soil fumigant, often as a mixture with 1,3-dichloropropene to control nematodes and soil pests.

What are the applications of Application

1,2-Dichloropropane is A byproduct in the production of epichlorohydrin

Definition

ChEBI: Rac-1,2-dichloropropane is a racemate comprising equimolar amounts of (R)- and (S)-1,2-dichloropropane. It is used as a fumigant to control nematodes in soil and insects in stored grain. It has a role as a fumigant insecticide, an agrochemical, a carcinogenic agent and a polar aprotic solvent. It contains a (R)-1,2-dichloropropane and a (S)-1,2-dichloropropane.

General Description

Colorless watery liquid with a sweet odor. Sinks in water. Produces an irritating vapor.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

1,2-Dichloropropane reacts with strong oxidizers and strong acids. 1,2-Dichloropropane also reacts with aluminum. When confined, this reaction can lead to an explosion. 1,2-Dichloropropane is incompatible with bases and aluminum alloys. 1,2-Dichloropropane will attack some forms of plastics, rubber and coatings.

Hazard

Flammable, dangerous fire risk, explosive limits in air 3.4–14.5%. Toxic by ingestion and inhalation. Upper respiratory tract irritant and body weight effects. Questionable carcinogen.

Health Hazard

Contact with skin or eyes may cause irriation.

Fire Hazard

Special Hazards of Combustion Products: Toxic and irritating gases may be generated.

Flammability and Explosibility

Highly flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Suspected carcinogen with experimental carcinogenic data. Moderately toxic by inhalation and ingestion. Mddly toxic by skin contact. An eye irritant. Mutation data reported. Can cause liver, kidney, and heart damage. Can cause dermatitis. One of the more toxic chlorinated hydrocarbons. A suggested order of increasing toxicity is dichloromethane, trichloroethylene, carbon tetrachloride, dichloropropane, dichloroethane. Animals exposed to hgh concentrations often showed marked visceral congestion, fatty degeneration of the liver, kidney, and, less frequently, of the heart. They also showed areas of coagulation and necrosis of the liver. There was found to be a heavy mortality among mice exposed to 400 ppm concentrations. A flammable liquid and very dangerous fire hazard when exposed to heat or flame. Reacts with aluminum to form aluminum chloride. This reaction, when confined, can lead to explosion. Can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS , ALIPH AT1 C

Potential Exposure

Dichloropropane is used as a chemical intermediate in perchloroethylene and carbon tetrachloride synthesis, and as a lead scavenger for antiknock fluids. It is also used as a solvent for fats, oils, waxes, gums and resins; and in solvent mixtures for cellulose esters and ethers. Other applications include the use of dichloropropane; as a fumigant, alone and in combination with dichloropropane, as a scouring compound; and a metal degreasing agent. It is also used as an insecticidal fumigant

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

Carcinogenicity

The EPA states, “This substance has not undergone a complete evaluation and determination under US EPA’s IRIS program for evidence of human carcinogenicity potential.”
An epidemiological study of 71 Italian florists, who were found to have used an average of 162 kg/year of 1,2- dichloropropane, showed that the mean frequency of peripheral lymphocyte micronuclei for the florists was higher than the mean for 75 controls, but these findings are questionable.
An oral cancer bioassay conducted in rats and mice by NTP, concluded that there was “some evidence of carcinogenicity in both male and female mice based on incidences of liver tumors (primarily adenomas, equivocal evidence of carcinogenicity in female rats based on mammary gland adenocarcinomas and no evidence of carcinogenicity in male rats.” Additional detail is provided below. Propylene dichloride was fed by gavage to rats and mice, 5 days/week for 103 weeks. Dosageswere 0 (corn oil controls), 125, and 250 mg/kg for mice and 0, 62, and 125 mg/kg for rats. Survival was reduced in high-dose female rats and mice (possibly due to infection in female mice). Body weight was reduced in high-dose rats of both sexes, and clear-cell changes and necrosis of the livers were found in high-dose female rats. The investigators concluded that dose-related increases were observed for adenomas of the liver in both male (control, 7/50; low dose, 10/50; high dose, 17/50) and female mice. The increase in the frequency of liver carcinomas supported the evidence that there was a neoplastic response in the mouse liver for both sexes (males: 11/50, 17/50, 16/50; females: 1/50, 3/50, 4/50). Hepatocytomegaly and hepatic necrosis were increased in male mice, but not in female mice.

Environmental Fate

Biological. 1,2-Dichloropropane showed significant degradation with gradual adaptation in a static-culture flask-screening test (settled domestic wastewater inoculum) conducted at 25°C. At concentrations of 5 and 10 mg/L, percent losses after 4 weeks of incubation were 89 and 81, respectively. The amount lost due to volatilization was only 0–3% (Tabak et al., 1981).
Soil. Boesten et al. (1992) investigated the transformation of 14C-labeled 1,2-dichloropropane under laboratory conditions of three sub-soils collected from the Netherlands (Wassenaar low-humic sand, Kibbelveen peat, Noord-Sleen humic sand podsol). The groundwater saturated soils were incubated in the dark at 9.5–10.5°C. In the Wassenaar soil, no transformation of 1,2-dichloropropane was observed after 156 days of incubation. After 608 and 712 days, however, >90% degraded to nonhalogenated volatile compounds which were detected in the headspace above the soil. These investigators postulated these compounds could be propylene and n-propane in a ratio of 8:1. Degradation of 1,2- dichloropropane in the Kibbelveen peat and Noord-Sleen humic sand podsoil was not observed possibly because the soil redox potentials in both soils (50–180 and 650–670 mV, respectively) were higher than the redox potential in the Wassenaar soil (10–20 mV).
Groundwater. According to the U.S. EPA (1986) 1,2-dichloropropane has a high potential to leach to groundwater.
Photolytic. Distilled water irradiated with UV light (λ= 290 nm) yielded the following photolysis products: 2-chloro-1-propanol, allyl chloride, allyl alcohol and acetone. The half-lives in distilled water and distilled water containing hydrogen peroxide were 50 and 30 minutes, respectively (Milano et al., 1988).
Chemical/Physical. Hydrolysis of 1,2-dichloropropane in distilled water at 25°C produced 1-chloro-2-propanol and hydrochloric acid (Milano et al., 1988). The calculated hydrolysis half-life at 25°C and pH 7 is 15.8 years (Ellington et al., 1988). Ozonolysis yielded carbon dioxide at low ozone concentrations (Medley and Stover, 1983).
Emits toxic chloride fumes when heated to decomposition (Lewis, 1990).

Metabolic pathway

1,2-Dichloropropane is quite stable to hydrolytic and microbial degradation in soils. It is metabolised rapidly and extensively in animals via a combination of gluthathione conjugation, reductive dechlorination, hydrolytic displacement of the halogen and oxidation and hydroxylation reactions (Scheme 1).

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with 1,2-dichloropropane you should betrained on its proper handling and storage. Before enteringconfined space where this chemical may be present, checkto make sure that an explosive concentration does not exist.1,2-dichloropropane must be stored to avoid contact withaluminum since violent reactions occur. Store in tightlyclosed containers in a cool, well-ventilated area away fromstrong oxidizers (such as chlorine, bromine, and fluorine),strong acids (such as hydrochloric, sulfuric, and nitric), odichlorobenzene, and 1,2-dichloroethane. Sources of ignition, such as smoking and open flames, are prohibited where1,2-dichloropropane, is handled, used, or stored. Metal containers involving the transfer of=gallons or more of 1,2-dichloropropane should be grounded and bonded. Drumsmust be equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof 1,2-dichloropropane. Wherever 1,2-dichloropropane isused, handled, manufactured, or stored, use explosion-proofelectrical equipment and fittings. A regulated, marked areashould be established where this chemical is handled, used,or stored in compliance with OSHA Standard 1910.1045.

Shipping

UN1279 1,2-Dichloropropane, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Distil the propane from CaH2. It has a limited shelf life. [Beilstein 1 IV 195.]

Degradation

1,2-Dichloropropane (1) is stable to hydrolytic degradation with a DT₅₀ of 15.8 years (est.) at pH 7 and 25 °C (Ellington et aE., 1988). Milano et al. (1988) reported that the dechlorination of 1,2-dichloropropane in distilled water (25 °C) yielded 1-chloro-2-propanol(2) and HCl(3).
1,2-Dichloropropane was degraded rapidly in distilled water (DT₅₀ 50 min) after irradiation under UV light (290 nm) to yield 2, allyl chloride (4), allyl alcohol (5) and acetone (6) (Milano et al., 1988).

Incompatibilities

May form explosive mixture with air. May accumulate static electrical charges, and may cause ignition of its vapors. Contact with strong oxidizers, powdered aluminum may cause fire and explosion hazard. Strong acids can cause decomposition and the formation of hydrogen chloride vapors. Reacts with strong bases; o-dichlorobenzene, 1,2-dichloroethane. Corrosive to aluminum and its alloys. Attacks some plastics, rubber, and coatings.

Waste Disposal

Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.