Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility. For certain uses as a food additive, propylene glycol is considered as GRAS by the US Food and Drug Administration, and is approved for food manufacturing. In the European Union, it has E-number E1520 for food applications. For cosmetics and pharmacology, the number is E490. Propylene glycol is also present in propylene glycol alginate, which is known as E405. Propylene glycol is approved and used as a vehicle for topical, oral, and some intravenous pharmaceutical preparations in the US and Europe.
Structure The compound is sometimes called (alpha) α-propylene glycol to distinguish it from the isomer propane-1,3-diol, known as (beta) β-propylene glycol. Propylene glycol is chiral. Commercial processes typically use the racemate. The S-isomer is produced by biotechnological routes.
Production
Industrial Industrially, propylene glycol is mainly produced from propylene oxide (for food-grade use). According to a 2018 source, 2.16 M tonnes are produced annually. Manufacturers use either non-catalytic high-temperature process at 200 °C (392 °F) to 220 °C (428 °F), or a catalytic method, which proceeds at 150 °C (302 °F) to 180 °C (356 °F) in the presence of ion exchange resin or a small amount of sulfuric acid or alkali.
Final products contain 20% propylene glycol, 1.5% of dipropylene glycol, and small amounts of other polypropylene glycols. Further purification produces finished industrial grade or USP/JP/EP/BP grade propylene glycol that is typically 99.5% or greater. Use of USP (US Pharmacopoeia) propylene glycol can reduce the risk of Abbreviated New Drug Application (ANDA) rejection. Propylene glycol can also be obtained from glycerol, a byproduct from the production of biodiesel. This starting material is usually reserved for industrial use because of the noticeable odor and taste that accompanies the final product.
Laboratory (S)-Propanediol is synthesized via fermentation methods. Lactic acid and lactaldehyde are common intermediates. Dihydroxyacetone phosphate, one of the two products of breakdown (glycolysis) of fructose 1,6-bisphosphate, is a precursor to methylglyoxal. This conversion is the basis of a potential biotechnological route to the commodity chemical 1,2-propanediol. Three-carbon deoxysugars are also precursor to the 1,2-diol. A small-scale, nonbiological route from D-mannitol is illustrated in the following scheme:
Applications
Polymers Forty-five percent of propylene glycol produced is used as a chemical feedstock for the production of unsaturated polyester resins. In this regard, propylene glycol reacts with a mixture of unsaturated maleic anhydride and isophthalic acid to give a copolymer. This partially unsaturated polymer undergoes further crosslinking to yield thermoset plastics. Related to this application, propylene glycol reacts with propylene oxide to give oligomers and polymers that are used to produce polyurethanes. Propylene glycol is used in water-based acrylic architectural paints to extend dry time which it accomplishes by preventing the surface from drying due to its slower evaporation rate compared to water.
Food and drug In regulated amounts, propylene glycol is designated as safe for food manufacturing as an anticaking agent, emulsifier, flavor agent, humectant, texturizer, stabilizer, solvent, antioxidant, antimicrobial agent, and thickener. As regulated by the US FDA for substances deemed as GRAS, propylene glycol is "not subject to premarket review and approval by FDA because it is generally recognized, by qualified experts, to be safe under the intended conditions of use." The scientific panel evaluating propylene glycol for food manufacturing defined its conclusion as: "There is no evidence in the available information on [propylene glycol] that demonstrates, or suggests reasonable grounds to suspect, a hazard to the public when they are used at levels that are now current or might reasonably be expected in the future." The FDA law defined maximum limits for the use of propylene glycol in various food categories under good manufacturing practices:
2.0% for general food categories 2.5% for frozen dairy products 5% for alcoholic beverages 5% for nuts and nut products 24% for confections and frostings 97% for seasonings and flavorings The European Food Safety Authority authorizes propylene glycol for use in food manufacturing, establishing a safe daily intake of 25 mg per kg of body weight. Specifically for ice cream or ice milk products, Health Canada permits use of propylene glycol mono fatty acid esters as an emulsifier and stabilizer at a maximum level of use of 0.35% of the ice cream made from the ingredients mix. Propylene glycol is used in a variety of other edible items, such as baked goods, desserts, prepared meals, flavoring mixes, candy, popcorn, whipped dairy products, and soda. It is also used in beer to stabilize the foam. Vaporizers used for delivery of pharmaceuticals or personal-care products often include propylene glycol among the ingredients. In alcohol-based hand sanitizers, it is used as a humectant to prevent the skin from drying. Propylene glycol is used as a solvent in many pharmaceuticals, including oral, injectable, and topical formulations. Many pharmaceutical drugs which are insoluble in water utilize propylene glycol as a solvent and carrier; benzodiazepine tablets are one example. Propylene glycol is also used as a solvent and carrier for many pharmaceutical capsule preparations. Additionally, certain formulations of artificial tears use propylene glycol as an ingredient.
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