57-55-6

Basic information

• Product Name: Propylene glycol
• Synonyms: 1,2-PROPANEDIOL, GR ACS 99.5%;PROPYLENEGLYCOLTECHGRADE;Propane-1,2-diol particulates;Propane-1,2-diol total (vapour and particulates);Propylene Glycol, Reagent;Propylene glycol, Propylenglycolum;1,2-Propanediol 99%, extra pure;1,2-Propanediol 99+%, for analysis
• CAS NO: 57-55-6
• Molecular Formula: C₃H₈O₂
• Molecular Weight: 76.09
• EINECS: 200-338-0
• Product Categories: Medicine grade;INORGANIC & ORGANIC CHEMICALS
• Mol File: 57-55-6.mol
• Article Data: 785

Chemical Properties

• Melting Point: -60 °C
• Boiling Point: 187 °C(lit.)
• Flash Point: 225 °F
• Appearance: APHA: ≤10/Viscous Liquid
• Density: 1.036 g/mL at 25 °C(lit.)
• Vapor Density: 2.62 (vs air)
• Vapor Pressure: 0.08 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Store at RT.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 14.49±0.20(Predicted)
• Explosive Limit: 2.4-17.4%(V)
• Water Solubility: miscible
• Sensitive: Hygroscopic
• Merck: 14,7855
• BRN: 1340498
• CAS DataBase Reference: Propylene glycol(CAS DataBase Reference)
• NIST Chemistry Reference: Propylene glycol(57-55-6)
• EPA Substance Registry System: Propylene glycol(57-55-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: TY2000000
• TSCA: Yes
• Hazardous Substances Data: 57-55-6(Hazardous Substances Data)

Usage

Physical and Chemical Properties

Propylene glycol is scientifically named as “1,2-propanediol”, and has a chemical formula of CH3CHOHCH2OH and a molecular weight of 76.10. There is a chiral carbon atom in the molecule. Its racemate is a hygroscopic viscous liquid and is slightly spicy. It has a specific gravity of 1.036 (25/4 °C), a freezing point of-59 °C, and a boiling point of 188.2 °C, respectively 83.2 °C (1,333 Pa). It is miscible with water, acetone, ethyl acetate and chloroform, and is soluble in ether. It is soluble in many essential oils, but is not miscible with petroleum ether and paraffin oil. It is relatively stable to heat and light, and is more stable at low temperatures. Its L-isomer has a boiling point of 187 to 189 °C and a specific optical rotation [α] of D20-15.0°. It can be oxidized at high temperatures to propionaldehyde, lactic acid, pyruvic acid and acetic acid. Figure 1 the molecular structure of propylene glycol. Propylene glycol is a diol having the general nature of the alcohol. It can react with inorganic and organic acids to generate mono-or di-esters. It reacts with propylene oxide to generate ether, with hydrogen halide to generate halohydrin, and with acetaldehyde to generate methyl dioxolane.

Medicinal property and application

Propylene glycol has good solubility and less toxicity and irritation, and is widely used as solvents, extraction solvents and preservatives for injections (eg. intramuscular injections, intravenous injections) and non-injectable pharmaceutical preparations (such as oral liquid, ophthalmic preparations, otic preparations, dental preparations, rectovaginal preparations, transdermal preparations, etc.). It is better than glycerol solvent and can dissolve many substances such as corticosteroids (sex hormone), chloramphenicol, sulfonamides, barbiturate, reserpine, quinidine, corticosterone acetate, tetrahydropalmatine sulfate, mechlorethamine hydrochloride, vitamin A, vitamin D, many volatile oils, most of the alkaloids and many local anesthetics. Propylene glycol is similar to ethanol when used as a bacteriostatic agent, and its efficacy to inhibit mold is similar to glycerin and is slightly lower than that of ethanol. Propylene glycol is commonly used as a plasticizer for the aqueous film coating materials. Its mixture with equal amounts of water can delay the hydrolysis of certain drugs, and increase the stability of the preparation product. It is used as an antimicrobial preservative in 15% to 30% propylene glycol solution and semi-solid formulation, as humectants in about 15% propylene glycol topical formulation, and as solvent and co-solvent in 10% to 30% propylene glycol aerosol solvent, 10% to 25 % propylene glycol oral solution, 10% to 60% injectable formulation and 5% to 80% topical formulation. [Stability and storage condition] It is very stable at room temperature, but is oxidized when left open at high temperatures (above 280 °C); has a chemical stability after mixing with 95% ethanol or water; can be sterilized by autoclaving or sterile filtration. Propylene glycol has hygroscopicity, and should be positioned at cool and dry place and stored in dark airtight container. [Incompatibility] It has incompatibility with some oxidants (such as potassium permanganate).

Content analysis

A 10μl sample is injected into the gas chromatograph, which has a thermal conductivity detector. The column is 1m × 6.35mm stainless steel column. The filler is polyethylene glycol 20M (Carbowax compound 20M) 4%, and the carrier is a 40/60 mesh sieved polytetrafluoroethylene (Chromosorb T) or similar material. Helium carrier gas has a flow rate of 75ml/min. Injector temperature is 240 °C; column temperature is 120 to 200 °C, temperature increment is 5 °C/min; final temperature is 250 °C. Under specified conditions, the residence time of propylene glycol is about 5.7 minutes, the residence time of three kinds of glycol isomers are respectively 8.2, 9.0 and 10.2 minutes. The area of each peak is determined using any proper method, and then the percentage of propylene glycol area is calculated and transformed into mass percentage.

Toxicity

FAO/WHO (2000): ADI is 0 to 25mg/kg. LD50 is 22 to 23.9 mg/kg (mouse, oral). GRAS (FDA, §184.1666, 2000).

Use limitation

FAO/WHO (1984): Cottage cheese, the cream mixture amount of 5g/kg (used alone or in combination with other carriers and stabilizers). Japan (1998): Raw noodles, raw stuffing and cuttlefish smoked products ≤2%; skins for dumplings, steamed dumplings, spring rolls and wonton ≤1.2%; other food ≤0.6%. GB 2760-96: pastry 3.0g/kg, chewing gum. FDA, §184.1666 (2000): Alcoholic beverages 5%; frosting and candy 24%; frozen dairy 2.5%; flavoring agents, flavor enhancers 97%; nuts and nut products 5%; other food 2.0%.

Uses

Different sources of media describe the Uses of 57-55-6 differently. You can refer to the following data:
1. Propylene glycol is used for similar applications as other glycols. Propylene glycol is an important raw material for unsaturated polyester, epoxy resin, and polyurethane resin. The use amount in this area accounts for about 45% of the total consumption of propylene glycol. Such unsaturated polyester is used extensively for reinforced plastics and surface coatings. Propylene glycol is excellent in viscosity and hygroscopicity and is non-toxic, and thus is widely used as hygroscopic agent, antifreeze, lubricants and solvents in the food, pharmaceutical and cosmetic industry. In the food industry, propylene glycol reacts with fatty acid to give propylene ester of fatty acids, and is mainly used as food emulsifier; Propylene glycol is a good solvent for flavorings and pigments. Propylene glycol is commonly used as solvents, softeners and excipients, etc. in the pharmaceutical industry for the manufacture of various types of ointments and salves. Propylene glycol is also used as a solvent and a softener for cosmetic since it has good mutual solubility with various spices. Propylene glycol is also used as tobacco moisturizing agents, antifungal agents, food processing equipment lubricants and solvents for food marking ink. Aqueous solution of propylene glycol is an effective anti-freeze agent.
2. Next to water, propylene glycol is the most common moisturecarrying vehicle used in cosmetic formulations. It has better skin permeation than glycerin, and it also gives a pleasant feel with less greasiness than glycerin. Propylene glycol is used as a humectant because it absorbs water from the air. It also serves as a solvent for anti-oxidants and preservatives. In addition, it has preservative properties against bacteria and fungi when used in concentrations of 16 percent or higher. There is a concern that propylene glycol is an irritant at high concentrations, though it appears to be quite safe at usage levels under 5 percent.
3. Propylene Glycol is a humectant and flavor solvent that is a polyhy- dric alcohol (polyol). it is a clear, viscous liquid with complete solu- bility in water at 20°c and good oil solvency. it functions as a humectant, as do glycerol and sorbitol, in maintaining the desired moisture content and texture in foods such as shredded coconut and icings. it functions as a solvent for flavors and colors that are insoluble in water. it is also used in beverages and candy.
4. Used as a solvent.

Synthesis method

It can be obtained by hydrolysis of Propylene oxide: CH3CHCH2+H2O[H+]→CH3CH(OH)CH2OH Direct hydration Propylene oxide and water are fed in a molar ratio of 1: 15, and react at 150-2000 °C, a pressure of 1.2-1.4 MPa for 30 minutes to obtain 16% aqueous solution of propylene glycol, which is subjected to evaporation to obtain the finished product. Catalyzed hydrolysis The reaction is performed under catalyzation of sulfuric acid or hydrochloric acid. 0.5% to 1.0% dilute sulfuric acid is added into 10% to 15% aqueous solution of propylene oxide, the mixture is hydrolyzed at 50 to 70 °C; the hydrolysate is neutralized and concentrated under reduced pressure, and refined to obtain the finished products. The preparation method is a method in which propylene oxide is hydrolyzed to propylene glycol, and which can be carried out in the liquid phase. There are catalytic and non-catalytic processes in industry. Catalytic method is a method in which hydrolysis is carried out in the presence of 0.5% to 1% sulfuric acid at 50 to 70 °C. Non-catalytic process is carried out under high temperature and pressure (150 to 300℃, 980 to 2940kPa), and is used for production in domestic.

Acute toxicity

Oral-rat LD50: 20000 mg/kg; Oral-Mouse LD50: 32000 mg/kg

Irritation data

Eyes-rabbit 100 mg mild

Extinguishing agent

Dry powder, foam, sand, water.

Description

Propylene glycol is used as antifreeze in breweries and diaries, in the manufacture of resins, as a solvent, and as an emulsifier in food. It was present as an occupational sensitizer in the color-film developer Flexicolor.

Chemical Properties

Different sources of media describe the Chemical Properties of 57-55-6 differently. You can refer to the following data:
1. Propylene glycol has a slight, characteristic taste. It is practically odorless. It absorbs moisture when exposed to moist air.
2. Propylene glycol is a colorless, odorless, syrupy liquid.

Occurrence

Reported found in several varieties of mushrooms, roasted sesame seed, oat groats, parmesan cheese, cocoa, pecans and truffle.

Definition

An alcohol in which the hydroxyl groups are attached to a carbon atom of a branched or straight-chain aliphatic hydrocarbon.

Preparation

Manufactured by treating propylene with chlorinated water to form the chlorohydrin, which is converted to the glycol by treatment with sodium carbonate solution. It is also prepared by heating glycerol with sodium hydroxide.

Indications

Propylene glycol solution (40% to 60%, v/vCH2CH[OH]CH2OH, propylene glycol) applied to the skin under plastic occlusion hydrates the skin and causes desquamation of scales. Propylene glycol, isotonic in 2% concentration, is a widely used vehicle in dermatologic preparations. Hydroalcoholic gels containing propylene glycol or other substances augment the keratolytic action of salicylic acid. Keralyt gel consists of 6% salicylic acid, 19.4% alcohol, hydroxypropylcellulose, propylene glycol, and water and is an extremely effective keratolytic agent. Overnight occlusion is used nightly until improvement is evident, at which time the frequency of therapy can be decreased to every third night or once weekly. This therapy is well tolerated, is usually nonirritating, and has been most successful in patients with X-linked ichthyosis vulgaris. Burning and stinging may occur when applied to damaged skin. Patients with other abnormalities of keratinization with hyperkeratosis, scaling, and dryness may also benefit.

Production Methods

Propylene glycol generally is synthesized commercially by starting with propylene, converting to the chlorohydrin, and hydrolyzing to propylene oxide, which is then hydrolyzed to propylene glycol. It can also be prepared by other methods.

Brand name

Sentry Propylene Glycol (Union Carbide); Sirlene (Dow Chemical).

Aroma threshold values

Detection: 340 ppm

General Description

Thick odorless colorless liquid. Mixes with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

1,2-Propanediol is hygroscopic. 1,2-Propanediol is sensitive to excessive heat (tends to oxidize at high temperatures). 1,2-Propanediol can react with oxidizing materials. 1,2-Propanediol is incompatible with acid chlorides, acid anhydrides, chloroformates, and reducing agents. 1,2-Propanediol dissolves many essential oils. A mixture of 1,2-Propanediol with hydrofluoric acid and silver nitrate was put in a glass bottle which burst 30 minutes later.

Hazard

Toxic.

Health Hazard

Liquid may irritate eyes.

Fire Hazard

1,2-Propanediol is combustible.

Contact allergens

Propylene glycol is used as a solvent, a vehicle for topical medicaments such as corticosteroids or aciclovir, an emulsifier and humectant in food and cosmetics, and as antifreeze in breweries, in the manufactures of resins. It was present as an occupational sensitizer in the color film developer Flexicolor?. Patch tests in aqua are sometimes irritant.

Safety Profile

Slightly toxic by ingestion, skin contact, intraperitoneal, intravenous, subcutaneous, and intramuscular routes. Human systemic effects by ingestion: general anesthesia, convulsions, changes in surface EEG. Experimental teratogenic and reproductive effects. An eye and human skin irritant. Mutation data reported. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. May react with hydrofluoric acid + nitric acid + silver nitrate to form the explosive silver fulminate. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Propylene glycol is used as a solvent; emulsifying agent; food and feed additive; flavor, in manu- facture of plastics; as a plasticizer, surface-active agent; antifreeze, solvent, disinfectant, hydroscopic agent; coolant in refrigeration systems; pharmaceutical, brake fluid; and many others.

Carcinogenicity

Dewhurst et al. and Baldwin et al. in studies on the carcinogenicity of other chemicals used propylene glycol as the solvent. As a result they tested propylene glycol alone for carcinogenic activity in rats and mice. Dewhurst et al. used a single injection of 0.2 mL, whereas Baldwin et al. gave rats and mice three to five subcutaneous injections, amount not specified. In neither case were tumors observed during a period of about a year or 2 years . Wallenious and Lecholm applied propylene glycol to the skin of rats three times a week for 14 months but found no tumor formation. Stenback and Shubik confirmed these findings when they applied propylene glycol at undiluted strength and as a 50 and 10% solution in acetone to the skin of mice during their lifetimes. No tumors have been reported in the lifetime dietary feeding studies . In fact, Gaunt et al. specifically state that no tumors were found in the rats.

Environmental Fate

Propylene glycol can be released into the environment via industrial releases or by disposal of consumer products. Propylene glycol is readily soluble in water and has a low sorption partition coefficient (KOC), so has the ability to move through soil and to leach into ground water. Because of low vapor pressure (0.1 mmHg at 25°C) and high water solubility, there is minimal volatilization to the atmosphere from surface water releases as well as substantial removal of its vapors by wet deposition. Its low octanol/water partition coefficient (KOW) indicates that bioconcentration and biomagnification should not happen. Propylene glycol is readily degraded in surface water and soil, by chemical oxidation and microbial digestion, with a short half-life (1–5 days) in aerobic or anaerobic conditions. It is also rapidly degraded in the atmosphere by photochemical oxidation, with a half-life about 1 day. Although environmental releases can and do occur (airports must monitor storm water runoff of deicing solutions), human health effects are likely to be minor, at least in comparison to effects from potential exposures in clinical scenarios.

Purification Methods

Dry the diol with Na2SO4, decant and distil it under reduced pressure. [Beilstein 1 IV 2468.]

Toxicity evaluation

Propylene glycol has a low degree of toxicity in animals as well as humans, such that very high doses are needed to elicit effects in acute toxicity studies. The toxic effects of propylene glycol appear to be similar in animals and in humans. Central nervous system (CNS) depression, hematologic toxicity, hyperosmolarity, metabolic acidosis, cardiovascular effects, and renal toxicity encompass the main acute and subacute syndromes for propylene glycol. Most of the effects of propylene glycol can be ascribed to high concentrations of the parent molecule or to the accumulation of D,L-lactate in the blood. Due to its alcohol moiety, propylene glycol at very high concentrations is the most likely reason for the CNS depression. Also, because high concentrations of propylene glycol will increase the osmolarity of the blood, the hyperosmotic effects are likely due to the parent molecule. The cardiovascular and renal effects may be a result of the hyperosmolarity in combination with the metabolic acidosis. The acidosis itself results from the accumulation of lactate (both D- and L-forms), which has been well documented in both animals and humans.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong acids (especially nitric acid), strong bases, permanganates, dichromates; may cause a violent reaction.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.All federal, state, and local environmental regulations must be observed.

InChI:InChI:1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3

Synthetic route

glycerol (56-81-5) → propylene glycol (57-55-6)

Conditions	Yield
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%

methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6)

Conditions	Yield
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%

1,2-propylene cyclic carbonate (108-32-7) → propylene glycol (57-55-6)

Conditions	Yield
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;

carbon dioxide (124-38-9) + 4-fluoroaniline (371-40-4) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-fluorophenyl)-5-methyloxazolidin-2-one

Conditions	Yield
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%

carbon dioxide (124-38-9) + 4-chloro-aniline (106-47-8) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-chlorophenyl)-5-methyloxazolidin-2-one (14423-08-6, 111609-86-0, 111609-87-1)

Conditions	Yield
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%

carbon dioxide (124-38-9) + 4-bromo-aniline (106-40-1) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-bromophenyl)-5-methyloxazolidin-2-one

Conditions	Yield
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%

carbon dioxide (124-38-9) + p-aminoiodobenzene (540-37-4) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-iodophenyl)-5-methyloxazolidin-2-one

Conditions	Yield
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%

carbon dioxide (124-38-9) + 3,5-Dichloroaniline (626-43-7) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(3,5-dichlorophenyl)-5-methyloxazolidin-2-one

Conditions	Yield
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%

hydroxy-2-propanone (116-09-6) → propylene glycol (57-55-6)

Conditions	Yield
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%

methyl lactate (547-64-8) → propylene glycol (57-55-6)

Conditions	Yield
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.

1,4-dihydroxybut-2-yne (110-65-6) + hypophosphorous acid 3-chlorine-2-hydroxypropylester → propylene glycol (57-55-6) + 1-methylolallenephosphonous acid (93295-59-1)

Conditions	Yield
In 1,4-dioxane at 50℃; for 1h;	A 7.6 g B 97%

carbon dioxide (124-38-9) + aniline (62-53-3) + methyloxirane (75-56-9, 16033-71-9) → 5-methyl-3-phenyl-oxazolidin-2-one (708-57-6) + propylene glycol (57-55-6)

Conditions	Yield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; under 3750.38 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave;	A 95% B n/a

glycerol (56-81-5) → propylene glycol (57-55-6) + ethylene glycol (107-21-1)

Conditions	Yield
In isopropyl alcohol at 180℃; under 3750.38 Torr; for 24h; Inert atmosphere; Autoclave;	A 94% B 6%
With water; hydrogen; alumina, 27%; copper, 5%; copper oxide, 64%; lanthanum oxide, 5%; mixture of In methanol at 297℃; under 37503.8 Torr; Product distribution / selectivity;	A 86.2% B 8.8%
With Ru-Cu/TMG-BEN at 230℃; under 60006 Torr; for 18h; Autoclave;	A 85% B n/a

carbon dioxide (124-38-9) + methyloxirane (75-56-9, 16033-71-9) → 1,2-propylene cyclic carbonate (108-32-7) + propylene glycol (57-55-6)

Conditions	Yield
tetra-n-butylphosphonium chloride at 180℃; under 15001.5 - 37503.8 Torr; for 4h; Product distribution / selectivity; Gas phase;	A 0.3% B 93.4%
tetraethylphosphonium bromide at 180℃; under 15001.5 - 37503.8 Torr; for 4h; Product distribution / selectivity; Gas phase;	A 0.5% B 92.7%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; cellulose at 120℃; under 15001.5 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Green chemistry;	A 90% B n/a

propene (187737-37-7) → propylene glycol (57-55-6)

Conditions	Yield
Stage #1: propene With Oxone; sodium chloride In water; acetone at 30℃; for 20h; Large scale; Stage #2: With water; sodium hydroxide at 25 - 40℃; for 7h; pH=12; Large scale;	93%
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol
With diphenylselenoxide; potassium carbonate; osmium(VIII) oxide In acetone for 24h; Ambient temperature; Phenylmethyl Selenoxide;	95 % Chromat.

pyruvic acid methyl ester (600-22-6) → propylene glycol (57-55-6)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h;	93%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); hydrogen; sodium t-butanolate In methanol at 80℃; under 37503.8 Torr; for 12h; Glovebox; Autoclave; chemoselective reaction;	93%
With (o-PPh2C6H4NH2)2RuCl2; hydrogen; sodium methylate In tetrahydrofuran at 120℃; under 37503.8 Torr; for 8h; Reagent/catalyst;	98 %Chromat.

carbon dioxide (124-38-9) + 4-Ethoxyaniline (156-43-4) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-ethoxyphenyl)-5-methyloxazolidin-2-one

Conditions	Yield
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 93%

propene (187737-37-7) → propylene glycol (57-55-6) + 1-methoxy-2-propanol (107-98-2) + 2-methoxypropanol (1589-47-5) + methyloxirane (75-56-9, 16033-71-9)

Conditions	Yield
With dihydrogen peroxide; titanium-silicate In methanol at 40℃;	A n/a B n/a C n/a D 92%
With dihydrogen peroxide; titanium-silicate In methanol at 40℃;	A n/a B n/a C n/a D 78%
With dihydrogen peroxide; titanium-silicate In water at 30 - 80℃; under 18751.9 Torr; pH=4.5;	A n/a B n/a C n/a D 61%

L-Lactic acid (79-33-4) → propylene glycol (57-55-6)

Conditions	Yield
With ruthenium-carbon composite; hydrogen In water at 119.84℃; under 7500.75 - 60006 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Autoclave; Sealed tube;	92%
With 5% active carbon-supported ruthenium; hydrogen at 130℃; under 26252.6 Torr; for 4h; Temperature; Autoclave; Inert atmosphere;	61%

1,2-propylene cyclic carbonate (108-32-7) → methanol (67-56-1) + propylene glycol (57-55-6)

Conditions	Yield
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](bromo)(carbonyl)(hydride)iron(II); potassium tert-butylate; isopropyl alcohol In tetrahydrofuran at 140℃; for 6h; Time; Inert atmosphere; Schlenk technique; Green chemistry;	A 90 %Chromat. B 91%
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 36h; Catalytic behavior; Solvent;	A 51 %Chromat. B 91%
With [Mn(HN(C2H4PiPr2)2)(CO)2Br]; hydrogen; sodium t-butanolate In tetrahydrofuran at 120℃; under 22502.3 Torr; for 26h; Schlenk technique; Glovebox; Autoclave;	A 75% B 82%

carbon dioxide (124-38-9) + 3-nitro-aniline (99-09-2) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 5-methyl-3-(3-nitrophenyl)oxazolidin-2-one

Conditions	Yield
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 91%

propene (187737-37-7) → propylene glycol (57-55-6) + methyloxirane (75-56-9, 16033-71-9)

Conditions	Yield
With phosphotungstic acid; dihydrogen peroxide at 70℃; for 4h; Reagent/catalyst; Temperature;	A 5.65% B 90.1%
With [Fe(di(o-imidazol-2-ylidenepyridine)methane)(MeCN)2](PF6)2; dihydrogen peroxide In water; acetonitrile at 25℃; under 2850.29 Torr; for 3h; Catalytic behavior; Inert atmosphere;	A 64% B 11%
With pyridine; carbon dioxide; dihydrogen peroxide; methyltrioxorhenium(VII) In water; acetonitrile at 25 - 40℃; under 36201.3 Torr; for 3h;	A n/a B 18.2%

LACTIC ACID (849585-22-4) → propylene glycol (57-55-6)

Conditions	Yield
With hydrogen In water at 150℃; under 30003 Torr;	90%
With copper(II) oxide; zinc In water at 250℃; for 2h; Reagent/catalyst; Green chemistry;	63.8%
With hydrogen at 110 - 150℃; under 60006 Torr; for 22h; Time;	23.8%

glycerol (56-81-5) → propan-1-ol (71-23-8) + propylene glycol (57-55-6)

Conditions	Yield
In ethanol at 180℃; under 3750.38 Torr; for 24h; Inert atmosphere; Autoclave;	A 6% B 90%
With hydrogen at 210℃; under 33753.4 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure;	A n/a B 51.3%
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 24h;	A 34% B 18%

propene (187737-37-7) + d,l-2-ethylhexanal (123-05-7) → propylene glycol (57-55-6) + 2-Ethylhexanoic acid (149-57-5)

Conditions	Yield
With sulfuric acid; water; oxygen In water at 60℃; under 2280.15 Torr; for 16h; pH=1;	A 36% B 90%

oxiranyl-methanol (556-52-5) → propylene glycol (57-55-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 22h; Ambient temperature;	89%
With palladium on activated charcoal; diethyl ether Hydrogenation;
With hydrogen; Pd/magnetite In ethyl acetate at 23℃; under 760.051 Torr; for 5h;
With palladium 10% on activated carbon; hydrogen In neat (no solvent) at 80℃; under 6000.6 Torr; for 24h; Reagent/catalyst; Solvent; Temperature; Pressure; Time; Autoclave;
With palladium on activated carbon; hydrogen In ethanol at 20℃; under 2068.65 Torr; for 0.283333h; Flow reactor;

carbon dioxide (124-38-9) + 1-amino-naphthalene (134-32-7) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 5-methyl-3-(naphthalen-1-yl)oxazolidin-2-one

Conditions	Yield
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 89%

1,2-propylene cyclic carbonate (108-32-7) → propylene glycol (57-55-6) + carbonic acid dimethyl ester (616-38-6)

Conditions	Yield
With potassium carbonate In methanol at 119.84℃; for 2h; Temperature; Concentration; Autoclave; Industrial scale;	A n/a B 88%

carbon dioxide (124-38-9) + 4-methoxy-aniline (104-94-9) + methyloxirane (75-56-9, 16033-71-9) → propylene glycol (57-55-6) + 3-(4-Methoxyphenyl)-5-methyl-2-oxazolidinone (121485-50-5)

Conditions	Yield
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 87%

propylene glycol (57-55-6) + 4-nitrobenzaldehdye (555-16-8) → 4-methyl-2-(4-nitro-phenyl)-[1,3]dioxolane (65513-22-6)

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃;	93%
With toluene-4-sulfonic acid; benzene Unter Entfernen des entstehenden Wassers.;

propylene glycol (57-55-6) + acetone (67-64-1) → 2,2,4-trimethyl-1,3-dioxolane (1193-11-9, 116944-25-3)

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	100%
With Amberlyst 36 at 50℃; for 2h;	75%
With 4 A molecular sieve; Amberlyst A 15 In tetrahydrofuran for 24h; Ambient temperature;	35%

propylene glycol (57-55-6) + prednisolone hemisuccinate (2920-86-7) → Prednisolone 21-(2'-hydroxypropyl)succinate (76733-56-7)

Conditions	Yield
sulfuric acid for 2h; Heating;	100%

propylene glycol (57-55-6) + N-formyl-1-bromo-narwedine (122584-14-9) → 4a,5,9,10,11,12-hexhydro-1-bromo-3-methoxy-11-formyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-propylene ketal (252869-10-6)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 14h; Heating / reflux;	100%
	89.5%

propylene glycol (57-55-6) + carbonic acid dimethyl ester (616-38-6) → 1,2-propylene cyclic carbonate (108-32-7)

Conditions	Yield
at 120℃; for 7h; Product distribution / selectivity; Molecular sieve;	100%
In neat (no solvent) at 110℃; for 24h; Temperature; Molecular sieve; Green chemistry;	99%
With 1,1,1-trioctyl-1-methylphosphonium methylcarbonate at 90℃; for 1h; Catalytic behavior; Reagent/catalyst;	96%

propylene glycol (57-55-6) + [(CH3COCHCOCH3)2Al(μ-OCH(CH3)2)2Al(OCH(CH3)2)2] → [Al2(OCH(CH3)2)2(CH3COCHCOCH3)2(OCH2CHCH3O)]2 (163462-29-1)

Conditions	Yield
In benzene byproducts: i-PrOH; moisture free; refluxing; solvent removal; elem. anal.;	100%

propylene glycol (57-55-6) → ethanol (64-17-5)

Conditions	Yield
With Raney Ni In water at 179.84℃; for 1h; Inert atmosphere; Autoclave;	100%

propylene glycol (57-55-6) + (4-nitrophenyl)ethanone (100-19-6) → C11H13NO4

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	100%

propylene glycol (57-55-6) → 2-hydroxypropanal (3913-65-3)

Conditions	Yield
With 5% CuO-5% PdO-0.5% Bi2O3-0.5% In2O3/modified γ-Al2O3 catalyst; 5% NiO-2% V2O5-0.4% Y2O3/modified γ-Al2O3 catalyst at 180℃;	99.8%
bei der elektrochemischen Oxydation;
With quinolinium monofluorochromate(VI) In dimethyl sulfoxide at 34.85℃; Kinetics; Thermodynamic data; Further Variations:; Solvents; Temperatures; Reagents; Oxidation;

propylene glycol (57-55-6) + 4-oxopentanoic acid ethyl ester (539-88-8) → 2,4-dimethyl-1,3-dioxolane-2-propionic acid ethyl ester (5413-49-0)

Conditions	Yield
sulfuric acid In water at 95 - 106℃; under 30 - 80 Torr; Product distribution / selectivity;	99.8%
With sulfuric acid at 110 - 170℃; under 10 - 15 Torr;

propylene glycol (57-55-6) + benzaldehyde (100-52-7) → 4-methyl-2-phenyl-1,3-dioxolane (2568-25-4)

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	99.7%
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;	98%
With poly(styren-co-3-(1-vinyllimidazolium-3-yl)propane-1-sulfonate)-acid at 110℃; for 1.5h; Reagent/catalyst;	96.2%

propylene glycol (57-55-6) + cyclohexanone (108-94-1) → 2-methyl-1,4-dioxa-spiro[4.5]decane (4722-68-3)

Conditions	Yield
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;	99%
With salicylic acid resin supported FeCl3 In benzene at 88 - 96℃; for 2h;	98.5%
With cyclohexane at 105℃; for 1h; Dean-Stark;	94.6%

propylene glycol (57-55-6) + butanone (78-93-3) → 2-ethyl-2,4-dimethyl-[1,3]dioxolane (2916-28-1)

Conditions	Yield
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;	99%
for 2h; Reflux;	88.6%
With formylmorpholine-dimethylsulfate-adduct In dichloromethane for 24h; Ambient temperature;	72.7%

propylene glycol (57-55-6) + tert-butylchlorodiphenylsilane (58479-61-1) → 1-((tert-butyldiphenylsilyl)oxy)propan-2-ol (125803-68-1)

Conditions	Yield
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;	99%

propylene glycol (57-55-6) + [Ti(N-phenylsalicylideneimine(-H))2(O-i-Pr)2] → [Ti(N-phenylsalicylideneimine(-H))2(OCH2CH(CH3)O)] (943433-21-4)

Conditions	Yield
In benzene byproducts: (CH3)2CHOH; under unhydrous atm., soln. of ligand added to soln. of Ti compd. (3.06:3.01), refluxed, monitored by isopropanol liberated; concd., crystd., elem. anal.;	99%

2-chloroethanal (107-20-0) + propylene glycol (57-55-6) → 4-methyl-1,3-dioxolan-2-ylmethyl chloride (16390-83-3)

Conditions	Yield
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;	99%
With C13H16NO3S(1+)*0.5Cu(2+)*O4S(2-) In cyclohexane for 0.5h; Reflux;	99 %Chromat.
With solid acidic polymeric ionic liquid from [SO3H(CH2)3VIm]HSO4 and resorcinol-formaldehyde resin In cyclohexane for 0.5h; Reflux; Dean-Stark;	99 %Chromat.

propylene glycol (57-55-6) + carbon dioxide (124-38-9) → 1,2-propylene cyclic carbonate (108-32-7)

Conditions	Yield
With 2-Cyanopyridine; cerium(IV) oxide at 139.84℃; under 37503.8 Torr; for 1h; Temperature; Autoclave;	99%
With 1,10-Phenanthroline; calcium carbide; zinc trifluoromethanesulfonate In 1-methyl-pyrrolidin-2-one at 180℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox; Sealed tube;	92%
With potassium carbonate; (S)-propyleneoxide at 120℃; under 30003 Torr; for 10h; Reagent/catalyst; Pressure; Time; Autoclave; Green chemistry;	78%

propylene glycol (57-55-6) + (((hexane-1,6-diylbis(methylazanediyl))bis(methylene))bis(2,1-phenylene))diboronic acid → C28H42B2N2O4

Conditions	Yield
With magnesium sulfate In toluene at 100℃; for 2h;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + propylene glycol (57-55-6) + zinc(II) nitrate hexahydrate + isophthalic acid (121-91-5) → 12Zn(2+)*6C8H4O4(2-)*3C6H12N2*6C3H6O2(2-)

Conditions	Yield
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; zinc(II) nitrate hexahydrate; isophthalic acid In N,N-dimethyl-formamide for 1h; Stage #2: propylene glycol In N,N-dimethyl-formamide at 130℃; for 48h;	99%

propylene glycol (57-55-6) + octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride (27668-52-6) → dimethyloctadecyl-[3-[tris(2-hydroxypropoxy)silyl]propyl]ammonium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 145℃;	99%

propylene glycol (57-55-6) + cyclopentanone (120-92-3) → 2-methyl-1,4-dioxa-spiro[4.4]nonane (4745-16-8)

Conditions	Yield
With salicylic acid resin supported FeCl3 In benzene at 88 - 92℃; for 2h;	98.9%
With 4 A molecular sieve; Amberlyst A 15 In tetrahydrofuran for 24h; Ambient temperature;	71%
With formylmorpholine-dimethylsulfate-adduct In dichloromethane for 24h; Ambient temperature;	61.8%

propylene glycol (57-55-6) + 4-chlorobenzaldehyde (104-88-1) → 2-(4-chloro-phenyl)-4-methyl-[1,3]dioxolane (5406-37-1)

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	98.6%
With toluene-4-sulfonic acid; benzene Unter Entfernen des entstehenden Wassers.;
Al-Fe pillared montmorillonite clay In dichloromethane at 25℃; for 8h;	100 % Turnov.
With 1-hexyl-3-methylimidazolium tetrafluoroborate at 130℃; for 3h;

Upstream product

• 108-32-7 Propylene carbonate 
• 67-56-1 Methanol 

Downstream Products

• 458-37-7 Curcumin 
• 479-18-5 Diprophylline 
• 1323-39-3 PROPYLENE GLYCOL MONOSTEARATE (CONTAINS CA. 35% MONOPALMITATE) 
• 60687-93-6 LACCAIC ACID 
• 470-29-1 2,4-DIHYDROXY-3,3-DIMETHYLBUTANOIC ACID 
• 108-32-7 Propylene carbonate 
• 109-64-8 1,3-Dibromopropane 
• 110-98-5 1,1'-Oxydi-2-propanol 
• 25322-69-4 Poly(propylene glycol) 
• 2628-17-3 4-Hydroxystyrene 
• 3658-77-3 4-Hydroxy-2,5-dimethyl-3(2H)furanone 
• 37318-31-3 alpha-d-Glucopyranoside, beta-d-fructofuranosyl, octadecanoate 
• 517-89-5 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione 
• 83-86-3 Phytic acid 
• 874807-57-5 MONASCUS RED 
• 104227-87-4 Famciclovir 
• 127-17-3 Pyruvic acid 
• 142-28-9 1,3-Dichloropropane 
• 29218-27-7 2-OXAZOLIDINONE, 5-(HYDROXYMETHYL)-3-(3-METHYLPHENYL)- 
• 556-52-5 Glycidol 
• 57-53-4 Meprobamate 
• 96-24-2 3-Chloro-1,2-propanediol 
• 96-33-3 Methyl acrylate 

Recommend Products

• 22788-19-8  propylene glycol monolaurate 
• 112-16-3  n-dodecanoyl chloride 
• 57-55-6  propylene glycol 
• 1192-35-4  (+/-)-2r,4t-dimethyl-[1,3]dioxolane 
• 1192-35-4  cis-2,4-Dimethyl-1,3-dioxolan 
• 13002-08-9  1,1-dipentyloxyethane 
• 849585-22-4  LACTIC ACID 
• 141-46-8  Glycolaldehyde 
• 298-12-4  Glyoxilic acid 
• 52485-53-7  (S)-2-((R)-1-methoxy-2-oxo-ethoxy)-propionaldehyde 
• 50-99-7  glucose 
• 82119-77-5  8-allyl-2-oxo-2H-chromene-3-carboxylic acid 
• 1600-27-7  mercury(II) diacetate 
• 623-84-7  1,2-diacetoxypropane