96-24-2

Basic information

• Product Name: 3-Chloro-1,2-propanediol
• Synonyms: ,’-Dihydroxy-iso-propylchloride;1,2-Dihydroxy-3-chloropropane;1,2-Propanediol, 3-dichloro-;1-Chloro-1-deoxyglycerol;1-Chloropropane-2,3-diol;2-Propanediol,3-chloro-1;3-Chloro-1,2-dihydroxypropane;3-Chloro-1,2-propandiol
• CAS NO: 96-24-2
• Molecular Formula: C₃H₇ClO₂
• Molecular Weight: 110.54
• EINECS: 202-492-4
• Product Categories: Aliphatics;Metabolites & Impurities;Methocarbamol;Analytical Standards;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Chromatography;Environmental Standards;Metabolites;Organic Building Blocks;Oxygen Compounds;Pesticides;Pesticides &Polyols;Rodenticides;API Intermediate;fine chemical
• Mol File: 96-24-2.mol
• Article Data: 142

Chemical Properties

• Melting Point: -40°C
• Boiling Point: 213 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow/Liquid
• Density: 1.322 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.04 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.480(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 13.28±0.20(Predicted)
• Water Solubility: Soluble
• Merck: 14,2145
• BRN: 635684
• CAS DataBase Reference: 3-Chloro-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-1,2-propanediol(96-24-2)
• EPA Substance Registry System: 3-Chloro-1,2-propanediol(96-24-2)

Safety Data

• Hazard Codes: T
• Statements: 60-21-23/25-41-39-36-23/24/25-40
• Safety Statements: 53-26-36-39-45-38-36/37/39-28A-36/37
• RIDADR: UN 2689 6.1/PG 3
• WGK Germany: 3
• RTECS: TY4025000
• F: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 96-24-2(Hazardous Substances Data)

Usage

Description

3-Chloro-1, 2-propanediol is unusually formed upon the thermal processing of fat-containing foods1. It is useful in organic synthesis. It is an intermediate for the drug dyphylline; used as a solvent for acetate, etc., and as an intermediate for plasticizers, surfactants, and dyes2; be used as a solvent for preparing a plasticizer, a surfactant, a dye intermediate, a drug, or as a dye intermediate mainly for use as an acetyl fiber or the like. Also used as a plasticizer, surfactant and dye intermediate. In the pharmaceutical industry, it is used in the production of phlegm and phlegm and phlegm-removing guaiac oil ether, antiasthmatic drug theophylline, and hydroxyphylline. It is warned that it is a potential carcinogen and has antifertility activity1,3.

Sources

https://en.wikipedia.org/wiki/3-MCPD https://www.sigmaaldrich.com/catalog/product/aldrich/107271?lang=en®ion=US Gunn, S. A., T. C. Gould, and W. A. Anderson. "Possible mechanism of posttesticular antifertility action of 3-chloro-1, 2-propanediol. " Proceedings of the Society for Experimental Biology & Medicine Society for Experimental Biology & Medicine 132.2(1969): 656.

Chemical Properties

Clear pale yellow liquid

Uses

Different sources of media describe the Uses of 96-24-2 differently. You can refer to the following data:
1. To lower the freezing point of dynamite; in the manufacture of dye intermediates. As rodent chemosterilant.
2. (±)-3-Chloro-1,2-propanediol may be used as a reference standard for the determination of (±)-3-chloro-1,2-propanediol in food samples by gas chromatography with mass spectrometric detection (GC-MS).
3. It is used in the synthesis of glycerol esters,amines, and other derivatives; to lower thefreezing point of dynamite; and as a rodentchemosterilant (Merck 1989).

Definition

ChEBI: A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 294, 1941Synthetic Communications, 24, p. 1959, 1994 DOI: 10.1080/00397919408010203Synthesis, p. 295, 1989

General Description

A colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

Reactivity Profile

3-Chloro-1,2-propanediol is hygroscopic and may be sensitive to prolonged exposure to air. Glycols and their ethers undergo violent decomposition in contact with approximately 70% perchloric acid. .

Health Hazard

Different sources of media describe the Health Hazard of 96-24-2 differently. You can refer to the following data:
1. Glycerol α-monochlorohydrin is a highlytoxic, teratogenic, and carcinogenic com pound. It is also an eye irritant.Inhalation of 125 ppm in 4 hours wasfatal to rats. The lethal dose on mice viaintraperitoneal route was 10 mg/kg. Lowdosage can cause sleepiness, and on chronicexposure, weight lossLD50 value, oral (rats): 26 mg/kThis compound is a strong teratomer,causing severe reproductive effects. Animal studies indicated that the adverse effects wereof spermatogenesis type, related to the testes,sperm duct, and Cowper’s gland. These werepaternal effectsStudies on rats indicated that high exposure levels to glycerol chlorohydrin can giverise to thyroid tumors.
2. 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.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by inhalation. Experimental reproductive effects. A severe eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A chemosterilant for rodents. Combustible when exposed to heat or flame. Reaction with perchloric acid forms a sensitive explosive product more powerful than glyceryl nitrate. When heated to decomposition it emits toxic fumes of Cl-.

Waste Disposal

Chemical incineration is the most appropriatemethod of disposal.

InChI:InChI=1/C3H7ClO2/c4-2-1-3(5)6/h3,5-6H,1-2H2

Upstream product

• 51483-40-0 1,3-dibromo-2-chloro-propane 
• 563-63-3 silver(I) acetate 
• 107-18-6 allyl alcohol 
• 56-81-5 glycerol 
• 107-05-1 3-chloroprop-1-ene 
• 106-89-8 epichlorohydrin 
• 66089-98-3 methyl-2 phenyl-2 chloromethyl-4 dioxolanne-1,3 
• 71-41-0 pentan-1-ol 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 78-83-1 2-methyl-propan-1-ol 
• 67-63-0 isopropyl alcohol 
• 7647-01-0 hydrogenchloride 
• 556-52-5 oxiranyl-methanol 
• 7732-18-5 water 

Downstream Products

• 4847-93-2 3-piperidin-1-yl-propane-1,2-diol 
• 58403-04-6 4-chloromethyl-2-furan-2-yl-[1,3]dioxolane 
• 5579-92-0 1-(2,3-dihydroxy-propyl)-3,5-diiodo-1H-pyridin-4-one 
• 111038-24-5 7-(2,3-Dihydroxypropyl)-8-bromotheophylline 
• 69828-78-0 3-[1]naphthylamino-propane-1,2-diol 
• 72045-01-3 3-(4-n-hexylphenoxy)-propane-1,2-diol 
• 64049-49-6 4-(2,3-dihydroxypropoxy)benzaldehyde 
• 64049-48-5 2-(2,3-dihydroxy-propoxy)-benzaldehyde 
• 56266-47-8 1,2-bis-(2,3-dihydroxy-propoxy)-benzene 
• 76343-55-0 1-chloro-2,3-bis-(4-nitro-benzoyloxy)-propane 
• 145094-05-9 phosphoric acid-(β,β'-dihydroxy-isopropyl ester)-(2,3-dihydroxy-propyl ester) 
• 5149-48-4 3-(phenylthio)-1,2-propanediol 
• 621-24-9 3-m-Tolyloxy-propane-1,2-diol 
• 59-47-2 mephenesin 

Relevant articles and documents

Thermokinetics of reactions with liquid-liquid phase separation

Isothermal heat flow calorimetry with controlled thermoelectric cooling resp. heating is applied to study the critical slowing down of the kinetics of reactions with liquid-liquid phase separation. Results (i) on the acid-catalysed hydrolysis of chloromethyloxirane by water, and (ii) on the ring-opening and esterification of bromomethyloxirane by dichloroacetic acid in the presence of cyclohexane as an inert solvent, both at 298.15 K, are presented. The heat production w(t) which is proportional to the reaction rate ?ζ/?t (where ζ, is the reaction coordinate) exhibits a funnel-like fall-off when the reaction path intersects the binodal curve at the critical solution point CP. From the shape of this part of the w(t) curves an average value of the critical exponent Φ = 0.72±0,003, which refers to the change of ζ with t at constant T and p, is calculated. This result is to be compared with the theoretical value of Φ = 0.708 obtained from a modification of the Griffiths and Wheeler theory of critical points in multicomponent systems to chemically reacting systems far from equilibrium by introducing f as an additional extensive variable. This allows the critical slowing down of the reaction rates to be interpreted as resulting from the divergence of the correlation length ζ, resp. from the convergence of the transport phenomena to zero at the CP. ? VCH Verlagsgesellschaft mbH, 1996.

A Scalable and Efficient Synthesis of 3-Chloro-1,2-propanediol

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Selective synthesis of epichlorohydrin: Via liquid-phase allyl chloride epoxidation over a modified Ti-MWW zeolite in a continuous slurry bed reactor

The epoxidation of allyl chloride (ALC) to epichlorohydrin (ECH) with H2O2 using a piperidine (PI)-modified Ti-MWW catalyst (Ti-MWW-PI) in a continuous slurry reactor was investigated to develop an efficient reaction system for the corresponding industrial process. The reaction parameters, including solvent, reaction temperature, t-butanol/ALC mass ratio, ALC/H2O2 molar ratio, weight hourly space velocity of H2O2, and the addition amount of ammonia, were studied in detail to pursue high H2O2 conversion and ECH selectivity. A long catalytic lifetime of 244 h was achieved at high H2O2 conversion (>97.0%) and ECH selectivity (>99.8%) under optimized reaction conditions. The crystallinity was well maintained for the deactivated Ti-MWW-PI catalyst, which was regenerated by a combination of calcination and piperidine treatment. This journal is

Hydrogen-Catalyzed Acid Transformation for the Hydration of Alkenes and Epoxy Alkanes over Co-N Frustrated Lewis Pair Surfaces

Hydrogen (H2) is widely used as a reductant for many hydrogenation reactions; however, it has not been recognized as a catalyst for the acid transformation of active sites on solid surface. Here, we report the H2-promoted hydration of alkenes (such as styrenes and cyclic alkenes) and epoxy alkanes over single-atom Co-dispersed nitrogen-doped carbon (Co-NC) via a transformation mechanism of acid-base sites. Specifically, the specific catalytic activity and selectivity of Co-NC are superior to those of classical solid acids (acidic zeolites and resins) per micromole of acid, whereas the hydration catalysis does not take place under a nitrogen atmosphere. Detailed investigations indicate that H2 can be heterolyzed on the Co-N bond to form Hδ-Co-N-Hδ+ and then be converted into OHδ-Co-N-Hδ+ accompanied by H2 generation via a H2O-mediated path, which significantly reduces the activation energy for hydration reactions. This work not only provides a novel catalytic method for hydration reactions but also removes the conceptual barriers between hydrogenation and acid catalysis.

Preparation method for 1,3-propylene glycol from glycerol

The invention relates to a preparation method for 1,3-propylene glycol from glycerol, wherein the preparation method comprises the steps of chlorohydrination reaction, cyclization reaction, hydrogenation reaction and the like. The glycerin conversion rate of the preparation method reaches 99% or above, the yield of 1,3-propylene glycol reaches 65% or above, and the preparation method has the advantages of being simple in process, mild in reaction condition, small in investment, high in technical safety and easy to operate and control.