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1,2-Propanediol

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Name

1,2-Propanediol

EINECS 200-338-0
CAS No. 57-55-6 Density 1.036 g/cm3
PSA 40.46000 LogP -0.64050
Solubility miscible with water Melting Point -60 °C
Formula C3H8O2 Boiling Point 184.848 °C at 760 mmHg
Molecular Weight 76.0953 Flash Point 107.222 °C
Transport Information N/A Appearance clear viscous liquid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 57-55-6 (1,2-Propanediol) Hazard Symbols N/A
Synonyms

1,2-propane-diol;DL-1,2-Propanediol;(RS)-1,2-Propanediol;(+-)-1,2-Propanediol;Trimethyl glycol;Propylene Glycol(PG);alpha-Propylene glycol;2,3-Propanediol;Propylene glycol (TN);Propylene Glycol USP;Sirlene;1,2-dihydroxypropane;alpha-Propyleneglycol;Propylene glycol (JP14/USP);Isopropylene glycol;2-Hydroxypropanol;Sentry Propylene Glycol;Propane-1,2-diol;(+-)-Propylene glycol;Monopropylene glycol;Methylethyl glycol;Dowfrost;Methylethylene glycol;Propylene Glycol;

Article Data 785

1,2-Propanediol Synthetic route

56-81-5

glycerol

57-55-6

propylene glycol

Conditions
ConditionsYield
In isopropyl alcohol at 180℃; under 3750.38 Torr; for 8h; Inert atmosphere; Autoclave;100%
With sulfuric acid; hydrogen; Ni/Re pH=6.9 - 12.1; Industry scale;99%
With hydrogen In 1,4-dioxane at 179.84℃; under 7500.75 Torr; for 6h; Time; Reagent/catalyst; Autoclave;99%
75-56-9, 16033-71-9

methyloxirane

57-55-6

propylene glycol

Conditions
ConditionsYield
With CoIII(t-Bu-salen)-OTs; water at 40℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Autoclave;99%
With sulfuric acid; water at 27℃; for 6h;98.3%
With water at 40℃; for 3h; Catalytic behavior; Reagent/catalyst; Schlenk technique;93%
108-32-7

1,2-propylene cyclic carbonate

57-55-6

propylene glycol

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 10h; Catalytic behavior; Temperature; Time; Solvent; Pressure; Autoclave;99%
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Reagent/catalyst; Sealed tube; Autoclave;92%
With water; aluminum hydroxide; magnesium hydroxide at 140℃; Conversion of starting material;
124-38-9

carbon dioxide

371-40-4

4-fluoroaniline

75-56-9, 16033-71-9

methyloxirane

A

57-55-6

propylene glycol

B

3-(4-fluorophenyl)-5-methyloxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Autoclave;A n/a
B 99%
124-38-9

carbon dioxide

106-47-8

4-chloro-aniline

75-56-9, 16033-71-9

methyloxirane

A

57-55-6

propylene glycol

B

14423-08-6, 111609-86-0, 111609-87-1

3-(4-chlorophenyl)-5-methyloxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Autoclave;A n/a
B 99%
124-38-9

carbon dioxide

106-40-1

4-bromo-aniline

75-56-9, 16033-71-9

methyloxirane

A

57-55-6

propylene glycol

B

3-(4-bromophenyl)-5-methyloxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Autoclave;A n/a
B 99%
124-38-9

carbon dioxide

540-37-4

p-aminoiodobenzene

75-56-9, 16033-71-9

methyloxirane

A

57-55-6

propylene glycol

B

3-(4-iodophenyl)-5-methyloxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Autoclave;A n/a
B 99%
124-38-9

carbon dioxide

626-43-7

3,5-Dichloroaniline

75-56-9, 16033-71-9

methyloxirane

A

57-55-6

propylene glycol

B

3-(3,5-dichlorophenyl)-5-methyloxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Autoclave;A n/a
B 99%
116-09-6

hydroxy-2-propanone

57-55-6

propylene glycol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 179.84℃; under 7500.75 Torr; for 5h; Autoclave;98%
With 5%-palladium/activated carbon; water; zinc at 250℃; for 0.5h; Reagent/catalyst;98%
With 5% active carbon-supported ruthenium; water; zinc at 180℃; under 3750.38 Torr; for 20h; Autoclave; Inert atmosphere;82%
547-64-8

methyl lactate

57-55-6

propylene glycol

Conditions
ConditionsYield
With trans-RuCl2(PPh3)[PyCH2NH(CH2)2PPh2]; potassium methanolate; hydrogen In tetrahydrofuran at 40℃; under 37503.8 Torr; for 16h;98%
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 100℃; under 38002.6 Torr; for 2h; Autoclave;97%
With potassium tert-butylate; hydrogen; [tris(μ-chloro)bis((triphos)ruthenium(II))] chloride In methanol at 100℃; under 30003 Torr; for 15h; Product distribution / selectivity; Inert atmosphere; Autoclave;>= 99.9 %Chromat.

1,2-Propanediol Specification

1,2-Propanediol (CAS NO.57-55-6 ), also known as Propylene glycol, is a colorless, odorless, viscous, highly hygroscopic liquid with a faintly sweet taste. It is miscible with water, ethanol, ether, chloroform, acetone and other organic solvents. The solubility to hydrocarbons and chlorinated hydrocarbons is small, but it is strong than ethylene glycol. Propylene Glycol contains an asymmetrical carbon atom, so it exists in two optically active forms (dextrorotatory and sinistrorotatory isomers). And the commercial Propylene Glycol is a racemic mixture.

Physical properties about Propylene Glycol are: (1)ACD/LogP: -1.341; (2)ACD/LogD (pH 5.5): -1.34; (3)ACD/LogD (pH 7.4): -1.34; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 4.44; (7)ACD/KOC (pH 7.4): 4.44; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.43; (12)Molar Refractivity: 18.976 cm3; (13)Molar Volume: 73.444 cm3; (14)Polarizability: 7.523 10-24cm3; (15)Surface Tension: 38.0040016174316 dyne/cm; (16)Density: 1.036 g/cm3; (17)Flash Point: 107.222 °C; (18)Enthalpy of Vaporization: 49.011 kJ/mol; (19)Boiling Point: 184.848 °C at 760 mmHg; (20)Vapour Pressure: 0.203999996185303 mmHg at 25°C

Preparation of Propylene Glycol: Propylene Glycol can be obtaine by epoxypropane. It includes direct hydration and indirect hydration. The direct hydration is the reaction of epoxypropane and water at 150-160 °C and 0.78-0 .98 MPa. After evaporation and distillation, Propylene Glycol is obtained. The indirect hydration is the reaction of epoxypropane and water in the presence of catalyst sulfuric acid. In addition, Propylene Glycol also can be produced by direct catalytic oxidation from propylene. The catalyst is anhydrous tertiary butanol.

Uses of Propylene Glycol: Propylene Glycol is an important raw material in unsaturated polyester, epoxy resins, polyurethane resins, plasticizers and surfactants. The amount occupies about 45% of total consumption. This unsaturated polyester is largely used for surface coatings and reinforced plastics. Because of good viscosity and moisture absorption, and non-toxic, Propylene Glycol is widely used as a hygroscopic agent, antifreeze, lubricants and solvents in the food, pharmaceutical and cosmetics industries. In the food industry, Propylene Glycol and fatty acid reacts to produce propylene glycol ester of fatty acid, which is mainly used as food emulsifier. It is also used as solvent for spices, seasonings and food coloring. What's more, 1,2-propanediol is used as a humidifying agent of tobacco, mildew preventive, fruit ripening preservatives, film-forming coatings additives, antifreeze and heat transfer media, etc. It is often used as a substitute for ethanol and glycerol. In pharmaceutical industry, Propylene Glycol is commonly used as solvent in the manufacture of various types of ointment, softener, excipients, preservatives, vitamins, penicillin, etc. As Propylene Glycol has good solubility with various spices, it is also used as solvent of cosmetic and softeners, etc.

When you are using this chemical, please be cautious about it as the following: The Propylene Glycol is low toxicity. So the acute oral toxicity is very low, and large quantities are required to cause perceptible health damage in humans. In the human body, Propylene Glycol is metabolized into pyruvic acid (a normal part of the glucose-metabolism process, readily converted to energy), lactic acid (a normal acid generally abundant during digestion), acetic acid (handled by ethanol-metabolism), and propionaldehyde. So you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
1. Smiles:C([C@@H](C)O)O;
2. InChI:InChI=1/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intravenous 27gm/kg (27000mg/kg) VASCULAR: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 312, 1937.
child TDLo oral 79gm/kg/56W-I (79000mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pediatrics. Vol. 93, Pg. 515, 1978.
dog LD50 intravenous 26gm/kg (26000mg/kg)   National Technical Information Service. Vol. PB280-477,
dog LD50 oral 22gm/kg (22000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939.
guinea pig LD50 oral 18350mg/kg (18350mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
guinea pig LDLo subcutaneous 15500mg/kg (15500mg/kg)   National Technical Information Service. Vol. PB280-477,
infant TDLo parenteral 10gm/kg/3D-C (10000mg/kg)   Pediatrics. Vol. 72, Pg. 353, 1983.
mouse LD50 intraperitoneal 9718mg/kg (9718mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI

BLOOD: CHANGES IN SPLEEN
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 342, 1947.
mouse LD50 intravenous 6630mg/kg (6630mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1581, 1976.
mouse LD50 oral 22gm/kg (22000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 89, 1939.
mouse LD50 subcutaneous 17370mg/kg (17370mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Kriobiologiya i Kriomeditsina. Cryobiology and Cryomedicine. Vol. 8, Pg. 46, 1981.
quail LD50 oral > 2080mg/kg (2080mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rabbit LD50 intravenous 6500mg/kg (6500mg/kg)   National Technical Information Service. Vol. PB280-477,
rabbit LD50 oral 18500mg/kg (18500mg/kg)   FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 491, 1974.
rabbit LD50 skin 20800mg/kg (20800mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 101, 1974.
rabbit LDLo intramuscular 6300mg/kg (6300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: COMA
Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 109, 1932.
rat LD50 intramuscular 14gm/kg (14000mg/kg)   Interagency Collaborative Group on Environmental Carcinogenesis, National Cancer Institute, Memorandum, June 17, 1974Vol. 17JUN1974,
rat LD50 intraperitoneal 6660mg/kg (6660mg/kg)   Kriobiologiya i Kriomeditsina. Cryobiology and Cryomedicine. Vol. 9, Pg. 36, 1981.
rat LD50 intravenous 6423mg/kg (6423mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1581, 1976.
rat LD50 oral 20gm/kg (20000mg/kg)   Toxicology and Applied Pharmacology. Vol. 45, Pg. 362, 1978.
rat LD50 subcutaneous 22500mg/kg (22500mg/kg)   Interagency Collaborative Group on Environmental Carcinogenesis, National Cancer Institute, Memorandum, June 17, 1974Vol. 17JUN1974,

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