General Description
A colorless liquid with a mild odor. Slightly denser than water. Toxic by ingestion and inhalation . Flash point 270°F. Used to make plastics, resins and other chemicals.
Reactivity Profile
3-CHLOROPROPANOL-1(627-30-5) may be sensitive to prolonged exposure to light. This compound may react with oxidizing agents. .
Air & Water Reactions
Moderately soluble in water.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Chemical Properties
Colorless to pale-yellow liquid; characteristic
odor. Soluble in water, alcohols, and
ethers; insoluble in hydrocarbons. Combustible.
Uses
Chloropropanols have mutagenic and carcinogenic properties. The 3-monochloropropanol (3-MCPD) is the main chloropropanol found in hydrolyzates of vegetable protein (HVP) made by acid hydrolysis.
Uses
Trimethylene chlorohydrin is used in organicsynthesis to produce cyclopropane andtrimethylene oxide. It is an intermediate inthe synthesis of pharmaceuticals, agrochemicals, antiseptic agents, and dyes.
Preparation
3-Chloro-1-propanol is synthesized by the reaction of 1, 3-propanediol and hydrochloric acid, using benzene sulfonic acid as the catalyst.
Reaction: 250 g of trimethylene glycol are shaken with 450 g of sulfur chloride, the mixture becoming warm, sulfur dioxide being rapidly evolved, and sulfur deposited. This reaction continues for 1 hours without heating, whereafter the mixture is heated for a further 6 hours on the water-bath and then for 30 min, over a free flame. When no more sulfur dioxide is evolved, the mixture is allowed to cool, then extracted several times with ether. The sulfur is washed with ether, and the united ethereal layers are shaken with sodium carbonate solution to remove sulfur dioxide, dried over sodium sulfate, and freed from ether. The residue is fractionated and the fraction of b.p. 140-180° C is redistilled, giving 60% (160 g) of 3-chloro-1-propanol, b.p. 160-164°C/760 mm, 60-64° C/10 mm.
J. Amer. Chem. Soc, 38, 2481 (1916)
J. Chem. Soc, 1928, 2439
Synthesis Reference(s)
Journal of the American Chemical Society, 90, p. 2927, 1968
DOI: 10.1021/ja01013a033The Journal of Organic Chemistry, 55, p. 2968, 1990
DOI: 10.1021/jo00296a078Organic Syntheses, Coll. Vol. 1, p. 533, 1941
Waste Disposal
Trimethylene chlorohydrin is burned in achemical incinerator equipped with an afterburner and scrubber.
