497-04-1

Basic information

• Product Name: 2-chloropropane-1,3-diol
• Synonyms: 2-chloropropane-1,3-diol;2-CHLORO-1,3-PROPANEDIOL;2-MCPD;2-Chloro-1,3-dihydroxypropane;Glycerol beta-chlorohydrin;2-MCPD 2-Chloropropane-1,3-diol 98+%
• CAS NO: 497-04-1
• Molecular Formula: C₃H₇ClO₂
• Molecular Weight: 110.53948
• EINECS: 207-834-6
• Product Categories: Aliphatics;Metabolites & Impurities
• Mol File: 497-04-1.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 146℃ (18 Torr)
• Flash Point: 104.1°C
• Appearance: /
• Density: 1.3219
• Vapor Pressure: 0.00391mmHg at 25°C
• Refractive Index: 1.4831 (589.3 nm 20℃)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 13.57±0.10(Predicted)
• Stability: Stable. Hygroscopic. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2-chloropropane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloropropane-1,3-diol(497-04-1)
• EPA Substance Registry System: 2-chloropropane-1,3-diol(497-04-1)

Safety Data

• Hazardous Substances Data: 497-04-1(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

A metabolite of Dichloropropanols

General Description

Colorless liquid.

Air & Water Reactions

Hygroscopic. Water soluble .

Reactivity Profile

A halogenated alcohol. Many alcohols are flammable. Polyols are generally combustible, but their generally low volatility means that they are poorly flammable. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

Flash point data for 2-chloropropane-1,3-diol are not available. 2-chloropropane-1,3-diol is probably combustible.

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

Synthetic route

glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride; hexahydro-2H-oxepin-2-one In water at 110℃; under 6448.83 Torr; for 4h; Product distribution / selectivity;	A 1.9197% B 3.7294% C 93.414% D 0.5545%
With hydrogenchloride; malonic acid at 100 - 110℃; for 3 - 5h; Kinetics;	A ~ 0.5 %Chromat. B ~ 6 %Chromat. C 37 %Chromat. D 54 %Chromat.
With hydrogenchloride; succinic acid at 100℃; for 2.5h; Kinetics;	A 0.37 %Chromat. B 6.84 %Chromat. C 30.05 %Chromat. D 60.88 %Chromat.

acetic acid (64-19-7) + glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + 3-chloro-2-hydroxy-1-propyl acetate (24573-30-6) + 1,3-dichloro-2-acetoxypropane (3674-10-0) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride at 100℃; for 23.75h; Product distribution / selectivity;	A 1.11% B 4.03% C 57.78% D 0.42% E 0.34% F 9.98%

acetic acid (64-19-7) + glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + (+/-)-1-Acetoxy-2,3-dichloropropane (589-96-8) + 1,3-dichloro-2-acetoxypropane (3674-10-0)

Conditions	Yield
With hydrogenchloride at 90 - 123℃; under 5414.51 - 5724.8 Torr; for 1.5 - 2h; Product distribution / selectivity;	A 1% B 1.88% C 53.74% D 0.43% E 4.75%

1,3-dibromo-2-chloro-propane (51483-40-0) + silver(I) acetate (563-63-3) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
at 170℃; und nachfolgendes Verseifen mit ueberschuessigem Alkali bei 100grad;

oxiranyl-methanol (556-52-5) → 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With hydrogenchloride

oxiranyl-methanol (556-52-5) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride

allyl alcohol (107-18-6) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With water; chlorine im diffusen Tageslicht;
With air; water; chlorine im diffusen Tagenlicht;

allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With hypochloric acid

allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hypochloric acid

glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride
With disulfur dichloride

glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride at 100℃; durch Fraktionieren im Vakuum;
With hydrogenchloride; (2E)-but-2-enedioic acid at 100℃; for 2.5h; Conversion of starting material;
With hydrogenchloride; tartaric acid at 100℃; for 3h; Conversion of starting material;
With hydrogenchloride; acetyl chloride at 100℃; under 3375.34 Torr; for 1h;	A 9.2 %Chromat. B 78.7 %Chromat.

2-chloro-1,3-bis-trityloxy-propane (72767-38-5) → 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With hydrogenchloride In ethanol Heating;

diethyl 2-chloromalonate (14064-10-9) → 2-chloro-propane-1,3-diol (497-04-1)

Conditions	Yield
With aluminium hydride In tetrahydrofuran
With sodium tetrahydroborate In methanol at 0 - 20℃;

hypochloric acid (13898-47-0) + allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1)

hypochloric acid (13898-47-0) + allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

water (7732-18-5) + chlorine (7782-50-5) + allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

hydrogenchloride (7647-01-0) + glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 3-monochloro-1,2-propanediol (96-24-2)

hydrogenchloride (7647-01-0) + glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
in der Waerme;

hydrogenchloride (7647-01-0) + acetic acid (64-19-7) + glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
Abwesenheit;

allyl alcohol (107-18-6) → 2-chloro-propane-1,3-diol (497-04-1) + 3-Hydroxypropanal (2134-29-4) + hydroxy-2-propanone (116-09-6) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; copper dichloride; 6,6,6-trifluoro-1-phenylhexane-1,3,5-trione; tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) In tetrahydrofuran at 25℃;

3-monochloro-1,2-propanediol (96-24-2) + glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1)

Conditions	Yield
Stage #1: 3-monochloro-1,2-propanediol; glycerol With acetic acid at 110℃; for 0.333333h; Stage #2: With hydrogenchloride for 8.95h; Product distribution / selectivity;

glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + diglycerol (627-82-7) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
Stage #1: glycerol With acetic acid at 110℃; for 0.333333h; Stage #2: With hydrogenchloride for 8.95h; Product distribution / selectivity;

glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride; acetic acid at 105℃; under 975.098 Torr; for 5.5h; Product distribution / selectivity;
With hydrogenchloride; acetyl chloride at 100℃; under 3375.34 Torr; for 4h; Pressure; Reagent/catalyst;	A 5.3 %Chromat. B 86.8 %Chromat. C 7.4 %Chromat.
With hydrogenchloride; malonoyl dichloride at 100℃; under 3375.34 Torr; for 4h;	A 7.8 %Chromat. B 85.1 %Chromat. C 6.3 %Chromat.
With hydrogenchloride; phenylacetyl chloride at 100℃; under 3375.34 Torr; for 0.5h; Reagent/catalyst;	A 7.8 %Chromat. B 10.5 %Chromat. C 70.3 %Chromat.
With hydrogenchloride; acetic acid at 100℃; under 1500.15 - 6750.68 Torr; for 4h;

glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1)

Conditions	Yield
With hydrogenchloride; acetyl chloride at 100℃; under 7500.75 Torr; for 1h; Time;	A 5.1 %Chromat. B 8.8 %Chromat. C 86.1 %Chromat.

glycerol (56-81-5) → 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1)

Conditions	Yield
With hydrogenchloride; propionic acid at 100℃; under 3375.34 Torr; for 3h; Pressure; Reagent/catalyst;	A 5.1 %Chromat. B 92.9 %Chromat.
With hydrogenchloride; acetic acid at 100℃; under 1500.15 - 6750.68 Torr; for 4h;

glycerol (56-81-5) → 2,3-Dichloro-1-propanol (616-23-9) + 2-chloro-propane-1,3-diol (497-04-1) + 1,3-Dichloro-2-propanol (96-23-1) + oxiranyl-methanol (556-52-5) + 3-monochloro-1,2-propanediol (96-24-2)

Conditions	Yield
With hydrogenchloride; acetic acid at 100℃; under 6000.6 Torr; for 4h; Autoclave; Green chemistry;	A 188 g B n/a C 5.0 g D 8.1 g E n/a

2-chloro-propane-1,3-diol (497-04-1) + 8-amino-6-bromoquinoline (57339-57-8) → C12H6BrClN2

Conditions	Yield
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 12h;	78%

2-chloro-propane-1,3-diol (497-04-1) + 4-Bromo-1-naphthylamine (2298-07-9) → C13H7BrClN

Conditions	Yield
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 12h;	76%
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 12h;	75%

2-chloro-propane-1,3-diol (497-04-1) + 3-bromonaphthalen-1-amine (90766-34-0) → C13H7BrClN

Conditions	Yield
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 12h;	75%

2-chloro-propane-1,3-diol (497-04-1) + 3-<4-(methylphenyl)sulfonylaminomethylene>-1,1,7,7-tetramethoxy-4-heptanone (147189-48-8) → 2-chloro-1-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-propanol

Conditions	Yield
With sulfuric acid In 1,2-dichloro-ethane for 4.5h; Heating;	70%

diethyl acetal (105-57-7) + 2-chloro-propane-1,3-diol (497-04-1) → 5-chloro-2-methyl-[1,3]dioxane (5695-74-9)

Conditions	Yield
With hydrogenchloride

2-chloro-propane-1,3-diol (497-04-1) + potassium cyanide (151-50-8) → β,β'-dihydroxy-isobutyronitrile (98070-55-4)

Conditions	Yield
With water

2-chloro-propane-1,3-diol (497-04-1) → 5-chloro-[1,3,2]dioxathiane trans-2-oxide (16508-36-4)

Conditions	Yield
With thionyl chloride

2-chloro-propane-1,3-diol (497-04-1) → 5-chloro-[1,3,2]dioxathiane cis-2-oxide (16508-35-3)

Conditions	Yield
With thionyl chloride; diethyl ether

2-chloro-propane-1,3-diol (497-04-1) → 2-iodo-1,3-propanediol (5349-29-1)

Conditions	Yield
With acetone; sodium iodide at 100℃;

2-chloro-propane-1,3-diol (497-04-1) → trimethyleneglycol (504-63-2)

Conditions	Yield
With hydrogenchloride; sodium amalgam

2-chloro-propane-1,3-diol (497-04-1) + acetic anhydride (108-24-7) → acetic acid-(2-chloro-3-hydroxy-propyl ester) (859053-78-4)

2-chloro-propane-1,3-diol (497-04-1) + benzoyl chloride (98-88-4) → 1,3-bis-benzoyloxy-2-chloro-propane

Conditions	Yield
With pyridine; chloroform

2-chloro-propane-1,3-diol (497-04-1) + phenyl isocyanate (103-71-9) → phenyl-carbamic acid-(2-chloro-3-hydroxy-propyl ester)

glycerol 2-phosphate, free acid (17181-54-3) + 2-chloro-propane-1,3-diol (497-04-1) + ethylene glycol (107-21-1) → phosphoric acid-(β,β'-dihydroxy-isopropyl ester)-(2,3-dihydroxy-propyl ester) (145094-05-9)

Conditions	Yield
das Dinatriumsalz reagiert;

2-chloro-propane-1,3-diol (497-04-1) + acetone (67-64-1) → 5-chloro-2,2-dimethyl-[1,3]dioxane

Conditions	Yield
With phosphorus pentoxide

2-chloro-propane-1,3-diol (497-04-1) → 5-chloro-[1,3,2]dioxaselenane 2-oxide (27528-16-1)

Conditions	Yield
With selenious acid

2-chloro-propane-1,3-diol (497-04-1) + n-hexadecanoyl chloride (112-67-4) → 2-MCPD 1-palmitate (63326-63-6)

Conditions	Yield
With pyridine In diethyl ether

2-chloro-propane-1,3-diol (497-04-1) → 2-chloro-1,3-ditosylate propane (127395-13-5)

Upstream product

• 56-81-5 glycerol 
• 14064-10-9 diethyl 2-chloromalonate 
• 51483-40-0 1,3-dibromo-2-chloro-propane 
• 563-63-3 silver(I) acetate 
• 64-19-7 acetic acid 
• 96-24-2 3-monochloro-1,2-propanediol 
• 107-18-6 allyl alcohol 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 13898-47-0 hypochloric acid 
• 72767-38-5 2-chloro-1,3-bis-trityloxy-propane 
• 556-52-5 oxiranyl-methanol 

Downstream Products

• 5349-29-1 2-iodo-1,3-propanediol 
• 504-63-2 trimethyleneglycol 
• 145094-05-9 phosphoric acid-(β,β'-dihydroxy-isopropyl ester)-(2,3-dihydroxy-propyl ester) 
• 63326-63-6 2-MCPD 1-palmitate 
• 127395-13-5 2-chloro-1,3-ditosylate propane 
• 36518-02-2 3-(2,3-dihydroxypropyl)-2-methylquinazolin-4(3H)-one 
• 96-24-2 3-monochloro-1,2-propanediol 
• 534-03-2 serinol 
• 1639207-42-3 2-MCPD 1,3-dioleate 
• 26787-56-4 2-MCPD 1,3-distearate 
• 169471-41-4 2-chloro-1,3-(dipalmitoyloxy)propane 
• 556-52-5 oxiranyl-methanol 
• 56-81-5 glycerol 
• 106-89-8 epichlorohydrin 

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